NZ734281B2

NZ734281B2 - Condensed heterocyclic compounds and pesticides

Info

Publication number: NZ734281B2
Application number: NZ734281A
Authority: NZ
Inventors: Masaki Kobayashi; Takao Kudo; Yukihiro Maizuru; Hiroto Matsui; Kenkichi Noto; Ayano Tanaka
Original assignee: Nissan Chemical Industries Ltd
Priority date: 2015-02-12
Filing date: 2016-02-12
Publication date: 2022-01-06

Abstract

Provided is a novel noxious organism control agent, particularly an insecticide or a miticide. A condensed heterocyclic compound represented by formula (1) [wherein D substituted by -S(O)nR1 represents a ring represented by D1, D2 or D3; Q represents a ring represented by Q1, Q2, Q3 or Q4; R1 represents a (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl-(C1-C6) alkyl group, a C3-C6 halocycloalkyl-(C1-C6) alkyl group or a hydroxy-(C1-C6) alkyl group each of which is optionally substituted by a C1-C6 alkyl group, a C1-C6 haloalkyl group or R1a; R1a represents a C1-C8 alkoxycarbonyl group; and n represents an integer of 0, 1 or 2], a salt of the condensed heterocyclic compound, or an N-oxide of the condensed heterocyclic compound or the salt. sents a (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl-(C1-C6) alkyl group, a C3-C6 halocycloalkyl-(C1-C6) alkyl group or a hydroxy-(C1-C6) alkyl group each of which is optionally substituted by a C1-C6 alkyl group, a C1-C6 haloalkyl group or R1a; R1a represents a C1-C8 alkoxycarbonyl group; and n represents an integer of 0, 1 or 2], a salt of the condensed heterocyclic compound, or an N-oxide of the condensed heterocyclic compound or the salt.

Description

DESCRIPTION TITLE OF INVENTION: CONDENSED HETEROCYCLIC COMPOUNDS AND PESTICIDES TECHNICAL FIELD The present invention relates to a novel condensed heterocyclic compound and its salt. A pesticide containing the compound as an active ingredient is described herein.

BACKGROUND ART For example, Patent Documents 1 to 31 disclose condensed heterocyclic compounds, however, they failed to disclose the condensed heterocyclic compounds of the present invention. Usefulness of the compounds as pesticides, especially, as insecticides, acaricides or parasiticides against internal or external parasites in or on a mammal or bird is not known at all.

In this specification where reference has been made to patent specifications, other external documents, or other sources of information, this is generally for the purpose of providing a context for discussing the features of the invention. Unless specifically stated otherwise, reference to such external documents is not to be construed as an admission that such documents, or such sources of information, in any jurisdiction, are prior art, or form part of the common general knowledge in the art.

PRIOR ART DOCUMENTS PATENT DOCUMENTS Patent Document 1: WO2016/005263 Patent Document 2: WO2015/198859 Patent Document 3: WO2015/133603 Patent Document 4: WO2015/121136 Patent Document 5: WO2015/091945 Patent Document 6: WO2015/087458 Patent Document 7: WO2015/071180 Patent Document 8: WO2015/059088 Patent Document 9: WO2015/002211 Patent Document 10: WO2015/000715 Patent Document 11: WO2014/157600 Patent Document 12: WO2014/148451 Patent Document 13: WO2014/142292 Patent Document 14: WO2014/132972 Patent Document 15: WO2014/132971 Patent Document 16: WO2014/123206 Patent Document 17: WO2014/123205 Patent Document 18: WO2014/104407 Patent Document 19: WO2013/180194 Patent Document 20: WO2013/180193 Patent Document 21: WO2013/191113 Patent Document 22: WO2013/191189 Patent Document 23: WO2013/191112 Patent Document 24: WO2013/191188 Patent Document 25: WO2013/018928 Patent Document 26: WO2012/086848 Patent Document 27: WO2012/074135 Patent Document 28: WO2011/162364 Patent Document 29: WO2011/043404 Patent Document 30: WO2010/125985 Patent Document 31: WO2009/131237 DISCLOSURE OF INVENTION TECHNICAL PROBLEM With the advance of development of pesticides targeted at various pest insects such as agricultural pest insects, forest pest insects or hygienic pest insects, various pesticides have been put into practical use.

However, recently, control of pest insects with conventional insecticides or fungicides has become difficult in more and more cases, as pest insects acquire resistance to them over many years of their use. Problems of the high toxicity of some conventional pesticides and of the disturbance of the ecosystem by some conventional pesticides which remain in the environment for a long period are becoming apparent.

Under these circumstances, development of novel pesticides with high pesticidal activity, low toxicity and low persistence is always expected.

It is an object of the present invention to provide a novel pesticide which has excellent pesticidal activities, which has low toxicity, for example, which has little harmful effect on non-target organisms such as mammals, fishes and useful insects, and which has low persistence; and/or to at least provide the public with a useful choice.

SOLUTION TO PROBLEMS The present inventors have conducted extensive studies to achieve the above object and as a result, found that a novel condensed heterocyclic compound represented by the following formulae (1) and (1-a-I1) of the present invention is a very useful compound which has excellent pesticidal activities particularly insecticidal and acaricidal activities, and which has little harmful effect on non-target organisms such as mammals, fishes and useful insects, and accomplished the present invention.

Accordingly, in a first aspect, the present invention relates to a condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with -S(O) R is a ring represented by D1: Q is a ring represented by Q1 : G1 is C(Y1), G2 is C(Y2), G is C(Y3), G4 is C(Y4), 1 1a A is N(A ), A is C(R ), A is C(R ), A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), R is C -C alkyl, R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl, 1 6 1 6 R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C6) alkylthio optionally substituted with R , C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, R is C1-C8 alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, R is C1-C8 alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, A is a hydrogen atom or C -C alkyl, each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with Y , C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C haloalkylsulfinyl, 1 6 1 6 1 6 90a 90b 90c 90b C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -C(O)R , -C(O)NHR , -C(O)N(R )R , 90e 90f 90g 90h 90g -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , -N(R )R , mercapto, - 90i 90j 90k 90j SC(O)R , -S(O)2NHR , -S(O)2N(R )R , -SF5, cyano, nitro, phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , Y is C -C alkoxycarbonyl Y is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl, Y is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, cyano or nitro, R is independently a hydrogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy 1 6 1 6 1 8 or C1-C8 haloalkoxy, 90b 90c 90i 90j 90k each of R , R , R , R and R is independently C1-C6 alkyl or C1-C6 haloalkyl, R is a hydrogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C 1 6 1 6 1 8 1 8 haloalkoxy, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-C6) alkylamino or di(C1-C6) haloalkylamino, R is C -C alkyl, C -C haloalkyl, C -C alkylamino, C -C haloalkylamino, di(C - 1 6 1 6 1 6 1 6 1 C6) alkylamino or di(C1-C6) haloalkylamino, 90g 90h each of R and R is independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C haloalkoxycarbonyl, 1 6 1 8 1 8 C -C alkylaminocarbonyl, C -C haloalkylaminocarbonyl, C -C alkylaminothiocarbonyl, 1 6 1 6 1 6 C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl or di(C1-C6) alkylaminosulfonyl, and n is an integer of 0, 1 or 2, wherein the compound represented by the formula (1) is not: In another aspect, the present invention relates to a condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with -S(O) R is a ring represented by D1: Q is a ring represented by Q2: G1 is C(Y1), G is C(Y2), G3 is C(Y3), G4 is C(Y4), A is C(R ), A is C(R ), A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), (excluding a case where both A and A are nitrogen atoms) R is C -C alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, R is C1-C8 alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, R is C1-C8 alkoxycarbonyl, each of R and R is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C -C haloalkyl, each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with Y , C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C haloalkylsulfinyl, 1 6 1 6 1 6 90a 90b 90c 90b C -C alkylsulfonyl, C -C haloalkylsulfonyl, -C(O)R , -C(O)NHR , -C(O)N(R )R , 1 6 1 6 90e 90f 90g 90h 90g -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , -N(R )R , mercapto, - 90i 90j 90k 90j SC(O)R , -S(O) NHR , -S(O) N(R )R , -SF , cyano, nitro, phenyl, phenyl optionally 2 2 5 substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , Y is C1-C8 alkoxycarbonyl Y is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl, Y is a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, 1 6 1 6 1 8 1 8 cyano or nitro, R is independently a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C1-C8 haloalkoxy, 90b 90c 90i 90j 90k each of R , R , R , R and R is independently C -C alkyl or C -C 1 6 1 6 haloalkyl, R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C -C alkylamino, C -C haloalkylamino, di(C -C ) alkylamino or di(C -C ) 1 6 1 6 1 6 1 6 haloalkylamino, R is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1- C6) alkylamino or di(C1-C6) haloalkylamino, 90g 90h each of R and R is independently C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 6 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C haloalkoxycarbonyl, 1 6 1 8 1 8 C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl, C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl or di(C1-C6) alkylaminosulfonyl, and n is an integer of 0, 1 or 2.

In another aspect, the present invention relates to a condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with -S(O)nR is a ring represented by D1: Q is a ring represented by Q4: G is C(Y1), G is C(Y2), G3 is C(Y3), G4 is C(Y4), A is a nitrogen atom or C(R ), R is C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C haloalkenyl, C -C alkynyl, 1 6 1 6 2 6 2 6 2 6 C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl, each of R and R is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C -C haloalkyl, R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1- C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with Y , C -C alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, 1 8 1 8 1 6 1 6 (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C haloalkylsulfinyl, 1 6 1 6 1 6 90a 90b 90c 90b C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -C(O)R , -C(O)NHR , -C(O)N(R )R , 90e 90f 90g 90h 90g -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , -N(R )R , mercapto, - 90i 90j 90k 90j SC(O)R , -S(O) NHR , -S(O) N(R )R , -SF , cyano, nitro, phenyl, phenyl optionally 2 2 5 substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , Y is C1-C8 alkoxycarbonyl Y is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl, Y is a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, 1 6 1 6 1 8 1 8 cyano or nitro, R is independently a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C -C haloalkoxy, 90b 90c 90i 90j 90k each of R , R , R , R and R is independently C -C alkyl or C -C 1 6 1 6 haloalkyl, R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C -C alkylamino, C -C haloalkylamino, di(C -C ) alkylamino or di(C -C ) 1 6 1 6 1 6 1 6 haloalkylamino, R is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1- C6) alkylamino or di(C1-C6) haloalkylamino, 90g 90h each of R and R is independently C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 6 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C haloalkoxycarbonyl, 1 6 1 8 1 8 C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl, C -C haloalkylaminothiocarbonyl, phenylcarbonyl, C -C alkylsulfonyl, C -C 1 6 1 6 1 6 haloalkylsulfonyl, C -C alkylaminosulfonyl or di(C -C ) alkylaminosulfonyl, and 1 6 1 6 n is an integer of 0, 1 or 2.

In another aspect, the present invention relates to a condensed heterocyclic compound represented by the formula (1-a-I1) or its salt or an N-oxide thereof: wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C -C alkylsulfinyl, C -C 1 8 1 6 1 6 1 6 1 6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, and n is an integer of 0, 1 or 2.

In another aspect, the present invention relates to a method of controlling internal or external parasites in or on mammals or birds, the method comprising administering to the mammal or bird in need thereof an effective amount of a condensed heterocyclic compound or its salt or an N-oxide thereof according to the present invention, wherein the mammal is not a human.

In another aspect, the present invention relates to a method of controlling insects, mites, or ticks, the method comprising applying an effective amount of a condensed heterocyclic compound or its salt or an N-oxide thereof according to the present invention.

In another aspect, the present invention relates to a method of controlling agricultural pests, the method comprising applying an effective amount of a condensed heterocyclic compound or its salt or an N-oxide thereof according to the present invention to seeds or to soil.

In the description in this specification reference may be made to subject matter which is not within the scope of the claims of the current application. That subject matter should be readily identifiable by a person skilled in the art and may assist in putting into practice the invention as defined in the claims of this application.

The term "comprising" as used in this specification and claims means "consisting at least in part of". When interpreting statements in this specification and claims which include the term "comprising", other features besides the features prefaced by this term in each statement can also be present. Related terms such as "comprise" and "comprised" are to be interpreted in similar manner.

Described herein are the following [1] to [167].

A condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with -S(O)nR is a ring represented by any one of D1, D2 and D3: Q is a ring represented by any one of Q1, Q2, Q3 and Q4: G1 is a nitrogen atom or C(Y1), G is a nitrogen atom or C(Y2), G3 is a nitrogen atom or C(Y3), G4 is a nitrogen atom or C(Y4), G is a nitrogen atom or C(Y5), T is N(T ), an oxygen atom or a sulfur atom, 1 1a 1 1a A is N(A ), an oxygen atom or a sulfur atom, A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), 1 1a R is C -C alkyl, C -C haloalkyl, (C -C ) alkyl optionally substituted with R , C - 1 6 1 6 1 6 2 C alkenyl, C -C haloalkenyl, C -C alkynyl, C -C haloalkynyl, C -C cycloalkyl, C -C 6 2 6 2 6 2 6 3 6 3 6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl or hydroxy (C -C ) alkyl, R is C -C alkoxy, C -C haloalkoxy, C -C alkoxycarbonyl, C -C alkylthio, C -C 1 8 1 8 1 8 1 6 1 6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl or cyano, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C cycloalkyl, C -C halocycloalkyl, C -C alkylthio, C -C 1 8 3 6 3 6 1 6 1 6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 20a 20g 20h 20g haloalkylsulfonyl, -C(O)R , -C(O)OH, hydroxy, -NH2, -NHR , -N(R )R , mercapto, cyano or nitro, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 2 6 haloalkenyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C -C alkylthio, C -C haloalkylthio, (C -C ) alkylthio optionally 1 6 1 6 1 6 substituted with R , C -C alkylsulfinyl, C -C haloalkylsulfinyl, C -C alkylsulfonyl, C - 1 6 1 6 1 6 1 30a 30e 30f C6 haloalkylsulfonyl, -C(O)R , -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, - 30g 30h 30g 30i NHR , -N(R )R , mercapto, -SC(O)R , -SF5, cyano, nitro, phenyl, phenyl optionally substituted with R , heterocyclyl or heterocyclyl optionally substituted with R , R is C1-C8 alkoxycarbonyl, R is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, cyano or nitro, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C -C haloalkynyl, C -C alkoxy, C -C haloalkoxy, C -C cycloalkyl, C -C 2 6 1 8 1 8 3 6 3 6 halocycloalkyl, C -C alkylthio, C -C haloalkylthio, (C -C ) alkylthio optionally 1 6 1 6 1 6 substituted with R , C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1- 40a 40e 40f C6 haloalkylsulfonyl, -C(O)R , -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, - 40g 40h 40g 40i NHR , -N(R )R , mercapto, -SC(O)R , -SF , cyano, nitro, phenyl, phenyl optionally substituted with R , heterocyclyl or heterocyclyl optionally substituted with R is C1-C8 alkoxycarbonyl, R is a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, 1 6 1 6 1 8 1 8 cyano or nitro, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C -C haloalkoxy, C -C cycloalkyl, C -C halocycloalkyl, C -C alkylthio, C -C 1 8 3 6 3 6 1 6 1 6 haloalkylthio, C -C alkylsulfinyl, C -C haloalkylsulfinyl, C -C alkylsulfonyl, C -C 1 6 1 6 1 6 1 6 50a 50g 50h 50g haloalkylsulfonyl, -C(O)R , -C(O)OH, hydroxy, -NH2, -NHR , -N(R )R , mercapto, cyano or nitro, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C cycloalkyl, C -C halocycloalkyl, C -C alkylthio, C -C 1 8 3 6 3 6 1 6 1 6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 60a 60g 60h 60g haloalkylsulfonyl, -C(O)R , -C(O)OH, hydroxy, -NH2, -NHR , -N(R )R , mercapto, cyano or nitro, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C -C alkylsulfonyl, C -C haloalkylsulfonyl, mercapto, -SF , cyano or 1 6 1 6 5 nitro, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy or cyano, A is a hydrogen atom, C -C alkyl, C -C haloalkyl, (C -C ) alkyl optionally 1 6 1 6 1 6 1a-a 1a-a substituted with A , (C -C ) haloalkyl optionally substituted with A , C -C alkenyl, 1 6 2 6 C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3- C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C(O)R , hydroxy or cyano, 1a-a A is C -C alkoxy, C -C haloalkoxy, C -C alkoxycarbonyl, C -C 1 8 1 8 1 8 1 8 haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, hydroxy or cyano, T is a hydrogen atom, C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C 1a 1 6 1 6 2 6 2 6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C -C ) alkyl, each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally substituted with Y , (C1-C6) haloalkyl optionally substituted with Y , C -C alkenyl, C -C haloalkenyl, (C -C ) alkenyl 2 6 2 6 2 6 optionally substituted with Y , C -C alkynyl, C -C haloalkynyl, (C -C ) alkynyl optionally 2 6 2 6 2 6 substituted with Y , C1-C8 alkoxy, C1-C8 haloalkoxy, (C1-C8) alkoxy optionally substituted with Y , C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, (C2-C6) alkenyloxy optionally substituted with Y , C -C alkynyloxy, C -C haloalkynyloxy, (C -C ) alkynyloxy 2 6 2 6 2 6 optionally substituted with Y , C -C cycloalkyl, C -C halocycloalkyl, C -C cycloalkyl 3 6 3 6 3 6 (C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1- C6) alkylthio optionally substituted with Y , C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2- C alkynylthio, C -C haloalkynylthio, C -C alkylsulfinyl, C -C haloalkylsulfinyl, (C -C ) 6 2 6 1 6 1 6 1 6 alkylsulfinyl optionally substituted with Y , C -C alkenylsulfinyl, C -C haloalkenylsulfinyl, 2 6 2 6 C2-C6 alkynylsulfinyl, C2-C6 haloalkynylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, (C -C ) alkylsulfonyl optionally substituted with Y , C -C 1 6 2 6 alkenylsulfonyl, C -C haloalkenylsulfonyl, C -C alkynylsulfonyl, C -C 2 6 2 6 2 6 90a 90b 90c 90b haloalkynylsulfonyl, -C(O)R , -C(O)NHR , -C(O)N(R )R , -C(O)OH, - 90d 90a 90e 90f 90g C(=NOR )R , -C(O)NH2, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , - 90h 90g 90i 90j 90k 90j N(R )R , mercapto, -SC(O)R , -S(O) NHR , -S(O) N(R )R , -SF , cyano, nitro, 2 2 5 phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , each of Y5 and Y6 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1- C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, mercapto, -SF , cyano or nitro, Y is C -C alkoxy, C -C haloalkoxy, C -C alkoxycarbonyl, C -C 1 8 1 8 1 8 1 8 haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, hydroxy or cyano, Y is C -C alkyl, C -C cycloalkyl, trimethylsilyl or phenyl, 1 6 3 6 Y is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, cyano or nitro, 10a 20a 30a 30e 40a 40e 50a 60a 90a each of R , R , R , R , R , R , R , R and R is independently a hydrogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy or C -C haloalkoxy, 1 6 1 6 1 8 1 8 20g 20h 30f 30g 30h 30i 40f 40g 40h 40i 50g 50h 60g 60h each of R , R , R , R , R , R , R , R , R , R , R , R , R , R , 90b 90c 90i 90j 90k R , R , R , R and R is independently C -C alkyl or C -C haloalkyl, 1 6 1 6 R is a hydrogen atom, C -C alkyl or C -C haloalkyl, 1 6 1 6 R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-C6) alkylamino or di(C1-C6) haloalkylamino, R is C -C alkyl, C -C haloalkyl, C -C alkylamino, C -C haloalkylamino, di(C - 1 6 1 6 1 6 1 6 1 C6) alkylamino or di(C1-C6) haloalkylamino, 90g 90h each of R and R is independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C haloalkoxycarbonyl, 1 6 1 8 1 8 C -C alkylaminocarbonyl, C -C haloalkylaminocarbonyl, C -C alkylaminothiocarbonyl, 1 6 1 6 1 6 C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C -C alkylaminosulfonyl or di(C -C ) alkylaminosulfonyl, and 1 6 1 6 n is an integer of 0, 1 or 2.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein D substituted with -S(O) R is a ring represented by D1, G is C(Y1), G2 is C(Y2), G3 is C(Y3), G4 is C(Y4), A is C(R ), A is C(R ), R is C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C haloalkenyl, C -C alkynyl, 1 6 1 6 2 6 2 6 2 6 C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, (C -C ) alkylthio optionally 1 8 1 6 1 6 1 6 substituted with R , C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1- C6 haloalkylsulfonyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, (C -C ) alkylthio optionally 1 8 1 6 1 6 1 6 substituted with R , C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1- C haloalkylsulfonyl, 6 8 each of R , R and R is independently a hydrogen atom, a halogen atom, C -C alkyl or C1-C6 haloalkyl, R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, 1a 1a-a A is a hydrogen atom, C -C alkyl, (C -C ) alkyl optionally substituted with A , 1 6 1 6 C -C alkenyl, C -C alkynyl, C -C alkoxy, C -C cycloalkyl or C(O)R , 2 6 2 6 1 8 3 6 1a-a A is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or cyano, R is a hydrogen atom, C -C alkyl or C -C alkoxy, 1 6 1 8 each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with Y , C -C alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, 1 8 1 8 1 6 1 6 (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C haloalkylsulfinyl, 1 6 1 6 1 6 90a 90b 90c 90b C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -C(O)R , -C(O)NHR , -C(O)N(R )R , 90e 90f 90g 90h 90g -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , -N(R )R , mercapto, - 90i 90j 90k 90j SC(O)R , -S(O) NHR , -S(O) N(R )R , -SF , cyano, nitro, phenyl, phenyl optionally 2 2 5 substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , and Y is C1-C8 alkoxycarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein D substituted with -S(O)nR is a ring represented by D2, Q is a ring represented by Q1, 1 1a A is N(A ), A is C(R ), A is C(R ), A is C(R ), A is a nitrogen atom, R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl, R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl, 1 6 1 6 R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with R , C -C alkylsulfinyl, C -C haloalkylsulfinyl, C -C alkylsulfonyl or C - 1 6 1 6 1 6 1 C haloalkylsulfonyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with R , C -C alkylsulfinyl, C -C haloalkylsulfinyl, C -C alkylsulfonyl or C - 1 6 1 6 1 6 1 C haloalkylsulfonyl, 1a 1a-a A is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A , C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R , 1a-a A is C -C alkoxy, C -C alkylthio, C -C alkylsulfinyl, C -C alkylsulfonyl or 1 8 1 6 1 6 1 6 cyano, R is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy, Y5 is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl, and 1 6 1 6 Y6 is a hydrogen atom, a halogen atom or C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein D substituted with -S(O) R is a ring represented by D3, Q is a ring represented by Q1, G1 is C(Y1), G2 is C(Y2), G3 is C(Y3), G4 is C(Y4), T is N(T ) or a sulfur atom, 1 1a 1 1a A is N(A ) A is C(R ), A is C(R ), A is C(R ), A is a nitrogen atom, R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl, R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl, 1 6 1 6 R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with R , C -C alkylsulfinyl, C -C haloalkylsulfinyl, C -C alkylsulfonyl or C - 1 6 1 6 1 6 1 C haloalkylsulfonyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with R , C -C alkylsulfinyl, C -C haloalkylsulfinyl, C -C alkylsulfonyl or C - 1 6 1 6 1 6 1 C haloalkylsulfonyl, 1a 1a-a A is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A , C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R , 1a-a A is C -C alkoxy, C -C alkylthio, C -C alkylsulfinyl, C -C alkylsulfonyl or 1 8 1 6 1 6 1 6 cyano, R is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy, T is a hydrogen atom or C -C alkyl, and 1a 1 6 each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, cyano or nitro. [5] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [2], wherein Q is a ring represented by Q1, 1 1a A is N(A ), R is C1-C6 alkyl, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, (C - 1 6 1 6 1 C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, and A is a hydrogen atom or C1-C6 alkyl. [6] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [5], wherein A is C(R ), and A is a nitrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [5] or [6], wherein A is C(R ), A is a nitrogen atom, R is a hydrogen atom, R is a hydrogen atom or C -C haloalkyl, Y1 is a hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl, Y2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, (C -C ) alkynyl optionally substituted with Y , C -C alkoxy, C -C alkylthio, C - 2 6 1 8 1 6 1 C haloalkylthio, (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C 6 1 6 1 6 1 6 90g c alkylsulfonyl, -NH2, -NHR , nitro, phenyl, phenyl optionally substituted with Y , thiophenyl, pyridinyl or pyridinyl, Y3 is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C6 alkylthio, (C1-C6) alkylthio optionally substituted with Y , C1-C6 alkylsulfinyl, C1-C6 90a 90c 90b alkylsulfonyl, -C(O)R , -C(O)N(R )R , -C(O)OH, cyano or nitro, Y4 is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 90h 90g C -C alkylthio, C -C alkylsulfonyl, -N(R )R or cyano, 1 6 1 6 Y is C1-C8 alkoxycarbonyl, Y is C3-C6 cycloalkyl or trimethylsilyl, Y is a halogen atom or C1-C6 haloalkyl, R is C1-C8 alkoxy, 90b 90c each of R and R is independently C -C alkyl, R is C -C alkyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl or 1 6 1 6 1 8 phenylcarbonyl, and R is C1-C6 alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [5], wherein A is a nitrogen atom, and A is C(R ).

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [5] or [8], wherein A is a nitrogen atom, A is C(R ), R is a hydrogen atom, R is C1-C6 haloalkyl, R is a hydrogen atom or C1-C6 alkyl, Y1 is a hydrogen atom, Y2 is a hydrogen atom, a halogen atom or C -C haloalkyl, Y3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl or cyano, and Y4 is a hydrogen atom, a halogen atom or C1-C8 alkoxy.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [2], wherein Q is a ring represented by Q2, A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), (excluding a case where both A and A are nitrogen atoms) R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, (C - 1 6 1 6 1 C6) alkylthio optionally substituted with R , C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, and R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C6) alkylthio optionally substituted with R , C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [10], wherein A is C(R ), and A is C(R ).

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [10], wherein A is C(R ), and A is a nitrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [10], wherein A is a nitrogen atom, and A is C(R ).

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [10] or [13], wherein A is a nitrogen atom, A is C(R ), R is C1-C6 haloalkyl, R is a hydrogen atom or C1-C6 alkyl, R is a hydrogen atom, a halogen atom or C -C alkyl, each of Y1 and Y4 is a hydrogen atom, Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and Y3 is a hydrogen atom or C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [2], wherein Q is a ring represented by Q3, A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), (excluding a case where both A and A are nitrogen atoms), R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C )alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, and R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C6) alkylthio optionally substituted with R , C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [15], wherein A is C(R ), and A is C(R ).

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [15], wherein A is C(R ), and A is a nitrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [15], wherein A is a nitrogen atom, and A is C(R ). id="p-19"

[19] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [15] or [18], wherein A is a nitrogen atom, A is C(R ), R is C1-C6 haloalkyl, R is a hydrogen atom, R is a hydrogen atom, Y1 is a hydrogen atom, each of Y2 and Y3 is independently a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and Y4 is a hydrogen atom or a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [2], wherein Q is a ring represented by Q4.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [20], wherein A is a nitrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [20], wherein A is C(R ).

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [20], [21] or [22], wherein R is C1-C6 alkyl, R is a hydrogen atom, R is C -C haloalkyl, R is a hydrogen atom or C -C alkyl, each of Y1 and Y4 is a hydrogen atom, Y2 is a hydrogen atom, a halogen atom or C -C haloalkyl, and Y3 is a hydrogen atom or C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [3], wherein R is C -C alkyl, R is a hydrogen atom, R is C1-C6 haloalkyl, R is a hydrogen atom, A is C -C alkyl, Y5 is a hydrogen atom, and Y6 is C1-C6 haloalkyl. id="p-25"

[25] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [4], wherein R is C1-C6 alkyl, R is a hydrogen atom, R is C -C haloalkyl, R is a hydrogen atom, A is C1-C6 alkyl, T1a is C1-C6 alkyl, each of Y1, Y3 and Y4 is a hydrogen atom, and Y2 is C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [2], wherein 1 1a A is N(A ) or an oxygen atom, R is a hydrogen atom, R is C -C haloalkyl, C -C haloalkylthio, C -C haloalkylsulfinyl or C -C 1 6 1 6 1 6 1 6 haloalkylsulfonyl, R is a hydrogen atom, R is a hydrogen atom or C1-C6 alkyl, R is a hydrogen atom, A is C -C alkyl, each of Y1 and Y4 is a hydrogen atom, and each of Y2 and Y3 is independently a hydrogen atom or C -C haloalkyl. id="p-27"

[27] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-A-A1), (1-A- B1), (1-A-C1), (1-A-D1), (1-A-E1), (1-A-F1), (1-A-G1), (1-A-H1), (1-A-I1), (1-A-J1), (1-A- K1), (1-A-L1), (1-A-M1) or (1-A-N1): The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1] or [3], wherein the formula (1) is the folloinwg formula (1-B-A1): The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1] or [4], wherein the formula (1) is the folloinwg formula (1-C-A1): The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-d-A1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C -C haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom, C -C alkyl, C -C alkenyl or C -C alkynyl, and 1 6 2 6 2 6 each of R , R , Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [30], wherein 1 1a each of R and A is independently C1-C6 alkyl, each of R and Y3 is independently C1-C6 haloalkyl, and each of R , R , Y2 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-e-A1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C -C alkylsulfinyl, C -C 1 8 1 6 1 6 1 6 1 6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and each of R , R , Y1, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [32], wherein 1 1a each of R and A is independently C -C alkyl, each of R and Y3 is independently C1-C6 haloalkyl, and each of R , R , Y1 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-f-A1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and each of R , R , Y1, Y2 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 id="p-35"

[35] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [34], wherein 1 1a each of R and A is independently C -C alkyl, R is C -C haloalkyl, each of R , R , Y1 and Y4 is a hydrogen atom, and Y2 is a hydrogen atom or a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-g-A1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C -C haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom, C -C alkyl, C -C alkenyl or C -C alkynyl, and 1 6 2 6 2 6 each of R , R , Y1, Y2 and Y3 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [36], wherein 1 1a each of R and A is independently C1-C6 alkyl, R is C1-C6 haloalkyl, each of R , R , Y1 and Y3 is a hydrogen atom, and Y2 is a halogen atom or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-a-G1): wherein R is C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C haloalkenyl, C -C alkynyl 1 6 1 6 2 6 2 6 2 6 or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C -C alkylsulfinyl, C -C 1 8 1 6 1 6 1 6 1 6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [38], wherein 1 1a each of R and A is independently C -C alkyl, each of R and Y3 is independently C -C haloalkyl, and each of R , R , Y1, Y2 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-a-I1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C -C alkylsulfinyl, C -C 1 8 1 6 1 6 1 6 1 6 haloalkylsulfinyl, C -C alkylsulfonyl or C -C haloalkylsulfonyl, 1 6 1 6 A is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [40], wherein 1 1a each of R and A is independently C1-C6 alkyl, R is C -C haloalkyl, Y2 is a hydrogen atom or C -C haloalkyl, Y3 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and each of R , R , Y1 and Y4 is a hydrogen atom. id="p-42"

[42] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-a-F1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C -C haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C -C alkylsulfonyl or C -C haloalkylsulfonyl, and 1 6 1 6 2 5 6 each of R , R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [42], wherein R is C1-C6 alkyl, R is C1-C6 haloalkyl, each of Y2 and Y3 is independently a hydrogen atom or C -C haloalkyl, and 2 5 6 each of R , R , R , Y1 and Y4 is a hydrogen atom. id="p-44"

[44] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein the formula (1) is the folloinwg formula (1-a-O1): wherein R is C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C haloalkenyl, C -C alkynyl 1 6 1 6 2 6 2 6 2 6 or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C -C alkylsulfinyl, C -C 1 8 1 6 1 6 1 6 1 6 haloalkylsulfinyl, C -C alkylsulfonyl or C -C haloalkylsulfonyl, and 1 6 1 6 3 5 6 each of R , R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [44], wherein R is C1-C6 alkyl, R is C1-C6 haloalkyl, each of R and Y2 is independently a halogen atom, and each of R , R , Y1, Y3 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-a-b1): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl, each of R and R is independently a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C - 1 6 1 8 1 8 1 6 1 6 1 C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [46], wherein R is C -C alkyl, R is C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, each of Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl, and 2 4 5 each of R , R , R , Y1 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-a-b2): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C -C haloalkynyl, each of R and R is independently a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1- C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, each of R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [48], wherein R is C -C alkyl, each of R and Y3 is independently C1-C6 haloalkyl, and each of R , R , Y1, Y2 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-a-m2): wherein R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C -C haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, and each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [50], wherein R is C -C alkyl, each of R and Y3 is independently C1-C6 haloalkyl, and each of R , R , Y1, Y2 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], [2] or [5], wherein the formula (1) is the folloinwg formula (1-a-p1): wherein R is C1-C6 alkyl, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, C - 1 6 1 6 1 C haloalkylsulfinyl or C -C haloalkylsulfonyl, 6 1 6 R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, A is a hydrogen atom or C1-C6 alkyl, and each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [52], wherein each of R and R is independently a hydrogen atom or a halogen atom, each of R and R is independently a hydrogen atom or C1-C6 haloalkyl, Y3 is C1-C6 haloalkyl, and each of Y1, Y2 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], [2] or [5], wherein the formula (1) is the folloinwg formula (1-a-q1): wherein R is C1-C6 alkyl, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, C - 1 6 1 6 1 C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, A is a hydrogen atom or C1-C6 alkyl, and each of R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [54], wherein each of R and Y2 is independently C1-C6 haloalkyl, A is C -C alkyl, and each of R , Y1, Y3 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], [2], [10] or [11], wherein the formula (1) is the folloinwg formula (1-a- E1): wherein R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, C - 1 6 1 6 1 C haloalkylsulfinyl or C -C haloalkylsulfonyl, 6 1 6 R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [56], wherein each of R , R , Y2 and Y3 is independently a hydrogen atom or C -C haloalkyl, each of R , R , Y1 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], [2], [10] or [12], wherein the formula (1) is the folloinwg formula (1-a- D1): wherein R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, C - 1 6 1 6 1 C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and each of R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [58], wherein R is C -C haloalkyl, Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, Y3 is a hydrogen atom or C1-C6 haloalkyl, and each of R , R , Y1 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], [2], [15] or [16], wherein the formula (1) is the folloinwg formula (1-a-j1): wherein R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, C1- C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, R is a hydrogen atom, a halogen atom or C -C haloalkyl, and each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [60], wherein each of R and Y3 is independently C -C haloalkyl, and 4 5 6 each of R , R , R , Y1, Y2 and Y4 is a hydrogen atom. id="p-62"

[62] The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], [2], [15] or [17], wherein the formula (1) is the folloinwg formula (1-a-j2): wherein R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, C - 1 6 1 6 1 C haloalkylsulfinyl or C -C haloalkylsulfonyl, 6 1 6 R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and each of R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [62], wherein R is C -C haloalkyl, Y2 is a hydrogen atom or a halogen atom, Y3 is a hydrogen atom or C1-C6 haloalkyl, and each of R , R , Y1 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [1], wherein D substituted with -S(O)nR is a ring represented by either D1 or D2, Q is a ring represented by either Q1 or Q2, R is C -C alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C1-C8 haloalkoxy, each of R and R is independently a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C - 1 6 1 8 1 8 1 6 1 6 1 C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, mercapto, cyano or nitro, R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl, 1 6 1 6 R is a hydrogen atom, a halogen atom or C -C alkyl, A is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C -C alkynyl, C -C haloalkynyl, C -C cycloalkyl (C -C ) alkyl or C -C 2 6 2 6 3 6 1 6 3 6 halocycloalkyl (C -C ) alkyl, and each of Y1, Y2, Y3, Y4, Y5 and Y6 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, cyano or nitro.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [2], wherein D substituted with -S(O)nR is a ring represented by D1, G1 is C(Y1), G is C(Y2), G is C(Y3), G4 is C(Y4), 1 1a A is N(A ) or an oxygen atom, A is C(R ), A is C(R ), 1 1a each of R and A is independently C1 -C6 alkyl, R is C -C haloalkyl, C -C haloalkylthio, C -C haloalkylsulfinyl or C -C 1 6 1 6 1 6 1 6 haloalkylsulfonyl, R is a hydrogen atom or C1 -C6 alkyl, each of Y2 and Y3 is independently a hydrogen atom or C1 -C6 haloalkyl, and 2 4 6 each of R , R , R , Y1 and Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to the above [3], wherein D substituted with -S(O) R is a ring represented by D2, Q is a ring represented by Q1, G5 is C(Y5), 1 1a A is N(A ), A is C(R ), A is C(R ), A is C(R ), A is a nitrogen atom, 1 1a each of R and A is independently C -C alkyl, each of R , R and Y5 is a hydrogen atom, and each of R and Y6 is independently C -C haloalkyl. id="p-67"

[67] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [66], wherein R is C1 -C6 alkyl, C1 -C6 haloalkyl, C2 -C6 alkenyl, C2 -C6 haloalkenyl, C2 -C6 alkynyl, C -C haloalkynyl, C -C cycloalkyl (C -C ) alkyl or C -C halocycloalkyl (C - 2 6 3 6 1 6 3 6 1 C ) alkyl. id="p-68"

[68] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [66], wherein R is C -C alkyl, C -C haloalkyl or C -C cycloalkyl (C -C ) alkyl. 1 6 1 6 3 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [66], wherein R is C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [66], wherein R is C1-C6 alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [66], wherein R is C1-C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [71], wherein R is C1-C8 alkoxy, C1-C8 alkoxycarbonyl or cyano.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [71], wherein R is C1 -C8 alkoxycarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [73], wherein R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [73], wherein R is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 8 alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, (C -C ) alkylthio 1 8 1 6 1 6 1 6 optionally substituted with R , C1 -C6 alkylsulfinyl, C1 -C6 haloalkylsulfinyl, C1 -C6 alkylsulfonyl or C1 -C6 haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is a hydrogen atom, a halogen atom, C1 -C6 haloalkyl, C1 -C6 alkylthio, (C1 - C6 ) alkylthio optionally substituted with R , C1 -C6 haloalkylthio, C1 -C6 haloalkylsulfinyl or C -C haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, 1 6 1 6 C -C haloalkylsulfinyl or C -C haloalkylsulfonyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is C -C haloalkylthio, C -C haloalkylsulfinyl or C -C haloalkylsulfonyl. 1 6 1 6 1 6 id="p-80"

[80] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is C1 -C6 haloalkylthio.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is C1 -C6 haloalkylsulfinyl. id="p-84"

[84] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [75], wherein R is C -C haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 8 alkoxy, C1 -C8 haloalkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio optionally substituted with R , C1 -C6 alkylsulfinyl, C1 -C6 haloalkylsulfinyl, C1 -C6 alkylsulfonyl or C -C haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is a hydrogen atom, a halogen atom, C1 -C6 haloalkyl, C1 -C6 alkylthio, (C1 - C ) alkylthio optionally substituted with R , C -C haloalkylthio, C -C 6 1 6 1 6 haloalkylsulfinyl or C -C haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is a hydrogen atom, a halogen atom, C -C haloalkyl, C -C haloalkylthio, 1 6 1 6 C1 -C6 haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is C -C haloalkylthio, C -C haloalkylsulfinyl or C -C haloalkylsulfonyl. 1 6 1 6 1 6 id="p-91"

[91] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [84], wherein R is C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [91], wherein R is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [91], wherein R is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [91], wherein R is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [91], wherein R is C -C alkyl. id="p-96"

[96] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [95], wherein R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [95], wherein R is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [95], wherein R is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [95], wherein R is C1 -C6 alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [99], wherein R is a hydrogen atom, a halogen atom or C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [99], wherein R is C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [101], wherein R is a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [101], wherein R is C -C alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [103], wherein A is a hydrogen atom, C -C alkyl, (C -C ) alkyl optionally substituted with 1 6 1 6 1a - a 1 0 a A , C -C alkenyl, C -C alkynyl, C -C alkoxy, C -C cycloalkyl or C(O)R . 2 6 2 6 1 8 3 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [103], wherein A is a hydrogen atom, C -C alkyl, C -C alkenyl, C -C alkynyl or C -C 1 6 2 6 2 6 3 6 cycloalkyl. id="p-106"

[106] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [103], wherein A is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [103], wherein A is C -C alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [107], wherein each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C alkynyl, (C -C ) alkynyl optionally 1 6 1 6 2 6 2 6 2 6 substituted with Y , C -C alkoxy, C -C haloalkoxy, C -C alkylthio, C -C 1 8 1 8 1 6 1 6 haloalkylthio, (C1 -C6 ) alkylthio optionally substituted with Y , C1 -C6 alkylsulfinyl, C1 -C6 9 0 a haloalkylsulfinyl, C1 -C6 alkylsulfonyl, C1 -C6 haloalkylsulfonyl, -C(O)R , - 90b 90c 90b 90e 9 0 f C(O)NHR , -C(O)N(R )R , -C(O)OH, hydroxy, -OC(O)R , -OS(O)2 R , - 9 0 g 9 0 h 9 0 g 9 0 i 90j NH2 , -NHR , -N(R )R , mercapto, -SC(O)R , -S(O)2 NHR , - 90k 90j c S(O) N(R )R , -SF , cyano, nitro, phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y . id="p-109"

[109] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [107], wherein each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkenyl, (C -C ) alkynyl optionally substituted with 1 6 1 6 2 6 2 6 Y , C1 -C8 alkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio optionally a 90a substituted with Y , C1 -C6 alkylsulfinyl, C1 -C6 alkylsulfonyl, -C(O)R , - 90c 9 0 b 90g 9 0 h 9 0 g C(O)N(R )R , -C(O)OH, -NH , -NHR , -N(R )R , mercapto, cyano, nitro, phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y .

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [109], wherein Y1 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [109], wherein Y1 is a hydrogen atom. id="p-112"

[112] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [109], wherein Y1 is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [109], wherein Y1 is C -C alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [109], wherein Y1 is C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [114], wherein Y2 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C2 -C6 alkenyl, (C2 -C6 ) alkynyl optionally substituted with Y , C1 -C8 alkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio optionally substituted with Y , C1 -C6 alkylsulfinyl, 90g c C1 -C6 alkylsulfonyl, -NH2 , -NHR , nitro, phenyl, phenyl optionally substituted with Y or heterocyclyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [114], wherein Y2 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [114], wherein Y2 is a hydrogen atom. id="p-118"

[118] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [114], wherein Y2 is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [114], wherein Y2 is C -C alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [114], wherein Y2 is C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [120], wherein Y3 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8 alkoxy, C -C alkylthio, (C -C ) alkylthio optionally substituted with Y , C -C 1 6 1 6 1 6 90a 90c 9 0 b alkylsulfinyl, C -C alkylsulfonyl, -C(O)R , -C(O)N(R )R , -C(O)OH, cyano or nitro. id="p-122"

[122] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [120], wherein Y3 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [120], wherein Y3 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [120], wherein Y3 is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [120], wherein Y3 is C -C alkyl. id="p-126"

[126] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [120], wherein Y3 is C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein Y4 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8 9 0 h 9 0 g alkoxy, C -C alkylthio, C -C alkylsulfonyl, -N(R )R or cyano. 1 6 1 6 The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein 90h 90g Y4 is C -C alkoxy, C -C alkylthio, C -C alkylsulfonyl, -N(R )R or cyano. 1 8 1 6 1 6 id="p-129"

[129] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein Y4 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein Y4 is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein Y4 is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein Y4 is C -C alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [126], wherein Y4 is C -C haloalkyl. id="p-134"

[134] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [133], wherein Y is C1 -C8 alkoxycarbonyl or C1 -C6 alkylcarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [133], wherein Y is C -C alkoxycarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [135], wherein Y is C1 -C6 alkyl, C3 -C6 cycloalkyl, trimethylsilyl or phenyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [135], wherein Y is C3 -C6 cycloalkyl or trimethylsilyl. id="p-138"

[138] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [135], wherein Y is C -C cycloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [135], wherein Y is trimethylsilyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [139], wherein Y is a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C 1 6 1 6 1 8 1 8 haloalkoxy, cyano or nitro. id="p-141"

[141] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [139], wherein Y is a halogen atom or C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [139], wherein Y is a halogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [139], wherein Y is C1 -C6 haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [143], wherein 10a 20a 30a 3 0 e 4 0 a 40e 50a 60a 90a each of R , R , R , R , R , R , R , R and R is independently a hydrogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8 alkoxy or C1 -C8 haloalkoxy.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [143], wherein 10a 20a 30a 3 0 e 4 0 a 40e 50a 60a 90a each of R , R , R , R , R , R , R , R and R is independently a hydrogen atom, C1 -C6 alkyl or C1 -C8 alkoxy.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [143], wherein 10a 20a 30a 3 0 e 4 0 a 40e 50a 60a 90a each of R , R , R , R , R , R , R , R and R is a hydrogen atom. id="p-147"

[147] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [143], wherein 10a 20a 30a 3 0 e 4 0 a 40e 50a 60a 90a each of R , R , R , R , R , R , R , R and R is independently C1 -C6 alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [143], wherein 10a 20a 30a 3 0 e 4 0 a 40e 50a 60a 90a each of R , R , R , R , R , R , R , R and R is independently C1 -C8 alkoxy.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [148], wherein 20g 20h 30f 3 0 g 3 0 h 30i 40f 4 0 g 4 0 h 40i 5 0 g each of R , R , R , R , R , R , R , R , R , R , R , 50h 60g 60h 9 0 b 90c 90 i 9 0 j 90k R , R , R , R , R , R , R and R is independently C1 -C6 alkyl or C -C haloalkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [148], wherein 20g 20h 30f 3 0 g 3 0 h 30i 40f 4 0 g 4 0 h 40i 5 0 g each of R , R , R , R , R , R , R , R , R , R , R , 50h 60g 60h 9 0 b 90c 90 i 9 0 j 90k R , R , R , R , R , R , R and R is independently C -C alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [150], wherein 90g 90 h each of R and R is independently C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 6 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C 1 6 1 8 1 8 haloalkoxycarbonyl, C1 -C6 alkylaminocarbonyl, C1 -C6 haloalkylaminocarbonyl, C1 -C6 alkylaminothiocarbonyl, C1 -C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1 -C6 alkylsulfonyl, C1 -C6 haloalkylsulfonyl, C1 -C6 alkylaminosulfonyl or di(C1 -C6 ) alkylaminosulfonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [151], wherein R is C1 -C6 alkyl, C1 -C6 haloalkylcarbonyl, C1 -C8 alkoxycarbonyl or phenylcarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [151], wherein R is C1 -C6 alkyl. id="p-154"

[154] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [151], wherein R is C -C haloalkylcarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [151], wherein R is C -C alkoxycarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [151], wherein R is phenylcarbonyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [156], wherein R is C1 -C6 alkyl.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [157], wherein T1 is a sulfur atom. id="p-159"

[159] The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [157], wherein T1 is N(T1a ).

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [159], wherein T is a hydrogen atom.

The condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of the above [1] to [159], wherein T1a is C1 -C6 alkyl.

A pesticide containing one or more members selected from the condensed heterocyclic compounds and their salts as defined in the above [1] to [161] as active ingredient(s). id="p-163"

[163] An agricultural chemical containing one or more members selected from the condensed heterocyclic compounds and their salts as defined in the above [1] to [161] as active ingredient(s).

A parasiticide against internal or external parasites in or on a mammal or bird, containing one or more members selected from the condensed heterocyclic compounds and their salts as defined in the above [1] to [161] as activie ingredient(s).

The parasiticide according to the above [164], wherein the external parasites are Siphonaptera or ticks.

An insecticide or acaricide containing one or more members selected from the condensed heterocyclic compounds and their salts as defined in the above [1] to [161] as active ingredient(s).

A seed treatment agent containing one or more members selected from the condensed heterocyclic compounds and their salts as defined in the above [1] to [161] as active ingredient(s).

The seed treatment agent according to the above [167], which is used to treat seeds by dipping.

A soil treatement agent containing one or more members selected from the condensed hetercyclic compounds as defined in the above [1] to [161] as active ingredient(s).

The soil treatment agent according to the above [169], which is used to treat soil by irrigation.

ADVANTAGEOUS EFFECTS OF INVENTION The compounds of the present invention have excellent insecticidal and acaricidal activities on many agricultural pest insects, spider mites, internal or external parasites in or on a mammal or bird and have sufficient controlling effect on pest insects which have acquired resistance to conventional insecticides. The compounds of the present invention have little harmful effect on mammals, fish and beneficial insects, show low persistence and are environmentally friendly. Thus, the present invention can provide useful novel pesticides.

DESCRIPTION OF EMBODIMENTS The compounds of the present invention can have geometrical isomers such as E- isomers and Z-isomers, depending on the types of substituents in them, and the present invention covers both E-isomers and Z-isomers and mixtures containing them in any ratios.

The compounds of the present invention can have optically active isomers due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and the present invention covers any optically active isomers and any racemates.

Further, the compounds of the present invention can have tautomers depending on the type of substituents in them, and the present invention covers all tautomers and mixtures containing them in any ratios.

Some of the compounds of the present invention can be converted, by ordinary methods, to salts with hydrogen halides such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, with inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloric acid, with sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid, with carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid and citric acid, with amino acids such as glutamic acid and aspartic acid, with alkali metals such as lithium, sodium and potassium, with alkaline earth metals such as calcium, barium and magnesium, with aluminum, and with quaternary ammonium such as tetramethylammonium, tetrabutylammonium and benzyltrimethylammonium.

In the present invention, the N-oxide is a compound having a nitrogen atom constituting the ring in the heterocyclic group oxidized. A heterocyclic group which may constitute an N-oxide may, for example, be a condensed ring containing a pyridine ring, a condensed ring containing a pyrazine ring, a condensed ring containing a pyridazine ring or a condensed ring containing a pyrimidine ring.

Next, specific examples of each substituent used herein will be given below. n- denotes normal, i- iso, s- secondary, and tert- tertiary.

As a "halogen atom" in the compounds of the present invention, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom may be mentioned. Herein, the expression "halo" also means such a halogen atom.

The expression "Ca-Cb alkyl" herein means a linear or branched hydrocarbon group containing from a to b carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n- butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl or n-hexyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkyl" herein means a linear or branched hydrocarbon group containing from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with halogen atom(s) which may be identical with or different from one another if two or more halogen atoms are present, such as fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2- difluoropropyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2- trifluoro(methyl)ethyl, 2,2,2-trifluoro(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro (trifluoromethyl)ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl and nonafluorobutyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkenyl" herein means a linear or branched unsaturated hydrocarbon group containing from a to b carbon atoms and having one or more double bonds in the molecule, such as vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methylpropenyl, 3-methylbutenyl or 1,1-dimethylpropenyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkenyl" herein means a linear or branched unsaturated hydrocarbon group containing from a to b carbon atoms and having one or more double bonds in the molecule, in which hydrogen atom(s) on carbon atom(s) are optionally substituted with halogen atom(s) which may be identical with or different from one another if two or more halogen atoms are present, such as 2,2-dichlorovinyl, 2- fluoropropenyl, 2-chloropropenyl, 3-chloropropenyl, 2-bromopropenyl, 3,3- difluoropropenyl, 2,3-dichloropropenyl, 3,3-dichloropropenyl, 2,3,3-trifluoro propenyl, 2,3,3-trichloropropenyl, 1-(trifluoromethyl)ethenyl, 4,4-difluorobutenyl, 3,4,4-trifluorobutenyl or 3-chloro-4,4,4-trifluorobutenyl, and those within the designated carbon number range are selected.

The expression "C -C alkynyl" herein means a linear or branched unsaturated hydrocarbon group containing from a to b carbon atoms and having one or more triple bonds in the molecule, such as ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1- hexynyl or 4,4,4-trifluorobutynyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkynyl" herein means a linear or branched unsaturated hydrocarbon group containing from a to b carbon atoms and having one or more triple bonds in the molecule, in which hydrogen atom(s) on carbon atom(s) are optionally substituted with halogen atom(s) which may be identical with or different from one another if two or more halogen atoms are present, such as 2-chloroethynyl, 2- bromoethynyl, 2-iodoethynyl, 3-chloropropynyl, 3-bromopropynyl or 3-iodo propynyl, and those within the designated carbon number range are selected.

The expression "C -C cycloalkyl" herein means a cyclic hydrocarbon group containing from a to b carbon atoms in the form of a 3- to 6-membered monocyclic or polycyclic ring which may optionally be substituted with an alkyl group as long as the number of carbon atoms does not exceed the designated carbon number range, such as cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and those within the designated carbon number range are selected.

The expression "C -C halocycloalkyl" herein means a cyclic hydrocarbon group containing from a to b carbon atoms in the form of a 3- to 6-membered monocyclic or polycyclic ring which may optionally be substituted with an alkyl group as long as the number of carbon atoms does not exceed the designated carbon number range, in which hydrogen atom(s) on carbon atom(s) in a ring moiety and/or in a side chain are optionally substituted with halogen atom(s) which may be identical with or different from one another if two or more halogen atoms are present, such as 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoromethylcyclopropyl, 2,2- dichloromethylcyclopropyl, 2,2-dibromomethylcyclopropyl or 2,2,3,3- tetrafluorocyclobutyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkoxy" herein means an alkyl-O- group in which the alkyl is a previously mentioned alkyl group containing from a to b carbon atoms, such as methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy or 2-ethylhexyloxy, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkoxy" herein means a haloalkyl-O- group in which the haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon atoms, such as difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2,-tetrafluoroethoxy, 2-chloro- 1,1,2-trifluoroethoxy or 1,1,2,3,3,3-hexafluoropropyloxy, and those within the designated carbon number range are selected.

The expression "C -C alkenyloxy" herein means an alkenyl-O- group in which the alkenyl is a previously mentioned alkenyl group containing from a to b carbon atoms, such as 2-propenyloxy, 2-butenyloxy, 2-methylpropenyloxy or 3-methylbutenyloxy, and those within the designated carbon number range are selected.

The expression "C -C haloalkenyloxy" herein means a haloalkenyl-O- group in which the haloalkenyl is a previously mentioned haloalkenyl group containing from a to b carbon atoms, such as 3,3-difluoroallyloxy or 3,3-dichloroallyloxy, and those within the designated carbon number range are selected.

The expression "C -C alkynyloxy" herein means an alkynyl-O- group in which the alkynyl is a previously mentioned alkynyl group containing from a to b carbon atoms, such as ethynyloxy, propargyloxy, 2-butynyloxy, 1-pentynyloxy or 1-hexynyloxy, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkynyloxy" herein means a haloalkynyl-O- group in which the haloalkynyl is a previously mentioned haloalkynyl group containing from a to b carbon atoms, such as 3-chloropropynyloxy, 3-bromopropynyloxy or 3-iodo propynyloxy, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkylthio" herein means an alkyl-S- group in which the alkyl is a previously mentioned alkyl group containing from a to b carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio or tert- butylthio, and those within the designated carbon number range are selected.

The expression "C -C haloalkylthio" herein means a haloalkyl-S- group in which the haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon atoms, such as difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro- 1,1,2-trifluoroethylthio, pentafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro(trifluoromethyl)ethylthio or nonafluorobutylthio, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkenylthio" herein means an alkenyl-S- group in which the alkenyl is a previously mentioned alkenyl group containing from a to b carbon atoms, such as 2-propenylthio, 2-butenylthio, 2-methylpropenylthio or 3-methylbutenylthio, and those within the designated carbon number range are selected.

The expression "C -C haloalkenylthio" herein means a haloalkenyl-S- group in which the haloalkenyl is a previously mentioned haloalkenyl group containing from a to b carbon atoms, such as 2-fluoropropenylthio, 2-chloropropenylthio, 3,3-difluoro propenylthio, 3,3-dichloropropenylthio, 2,3,3-trifluoropropenylthio, 4,4-difluoro butenylthio or 3,4,4-trifluorobutenylthio, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkynylthio" herein means an alkynyl-S- group in which the alkynyl is a previously mentioned alkynyl group containing from a to b carbon atoms, such as propynylthio, butynylthio, pentynylthio or hexynylthio, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkynylthio" herein means a haloalkynyl-S- group in which the haloalkynyl is a previously mentioned haloalkynyl group containing from a to b carbon atoms, such as 3-chloropropynylthio, 3-bromopropynylthio or 3-iodo propynylthio, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkylsulfinyl" herein means an alkyl-S(O)- group in which the alkyl is a previously mentioned alkyl group containing from a to b carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i- butylsulfinyl, s-butylsulfinyl or tert-butylsulfinyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkylsulfinyl" herein means a haloalkyl-S(O)- group in which the haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon atoms, such as difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro(trifluoromethyl)ethylsulfinyl or nonafluorobutylsulfinyl, and those within the designated carbon number range are selected.

The expression "C -C alkenylsulfinyl" herein means an alkenyl-S(O)- group in which the alkenyl is a previously mentioned alkenyl group containing from a to b carbon atoms, such as 2-propenylsulfinyl, 2-butenylsulfinyl, 2-methylpropenylsulfinyl or 3- methylbutenylsulfinyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkenylsulfinyl" herein means a haloalkenyl-S(O)- group in which the haloalkenyl is a previously mentioned haloalkenyl group containing from a to b carbon atoms, such as 2-fluoropropenylsulfinyl, 2-chloro propenylsulfinyl, 3,3-difluoropropenylsulfinyl, 3,3-dichloropropenylsulfinyl, 4,4- difluorobutenylsulfinyl or 3,4,4-trifluorobutenylsulfinyl, and those within the designated carbon number range are selected.

The expression "C -C alkynylsulfinyl" herein means an alkynyl-S(O)- group in which the alkynyl is a previously mentioned alkynyl group containing from a to b carbon atoms, such as 2-propynylsulfinyl or 2-butynylsulfinyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkynylsulfinyl" herein means a haloalkynyl-S(O)- group in which the haloalkynyl is a previously mentioned haloalkynyl group containing from a to b carbon atoms, such as 3-chloropropynylsulfinyl, 3-bromo propynylsulfinyl or 3-iodopropynylsulfinyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkylsulfonyl" herein means an alkyl-SO2- group in which the alkyl is a previously mentioned alkyl group containing from a to b carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i- butylsulfonyl, s-butylsulfonyl or tert-butylsulfonyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkylsulfonyl" herein means a haloalkyl-SO2- group in which the haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon atoms, such as difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl or 2-chloro-1,1,2-trifluoroethylsulfonyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkenylsulfonyl" herein means an alkenyl-SO2- group in which the alkenyl is a previously mentioned alkenyl group containing from a to b carbon atoms, such as 2-propenylsulfonyl, 2-butenylsulfonyl, 2-methylpropenylsulfonyl or 3- methylbutenylsulfonyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkenylsulfonyl" herein means a haloalkenyl-SO - a b 2 group in which the haloalkenyl is a previously mentioned haloalkenyl group containing from a to b carbon atoms, such as 2-fluoropropenylsulfonyl, 2-chloro propenylsulfonyl, 3,3-difluoropropenylsulfonyl, 3,3-dichloropropenylsulfonyl, 4,4- difluorobutenylsulfonyl or 3,4,4-trifluorobutenylsulfonyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkynylsulfonyl" herein means an alkynyl-SO2- group in which the alkynyl is a previously mentioned alkynyl group containing from a to b carbon atoms, such as 2-propynylsulfonyl or 2-butynylsulfonyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkynylsulfonyl" herein means a haloalkynyl-SO2- group in which the haloalkynyl is a previously mentioned haloalkynyl group containing from a to b carbon atoms, such as 3-chloropropynylsulfonyl, 3-bromo propynylsulfonyl or 3-iodopropynylsulfonyl, and those within the designated carbon number range are selected.

The expression "C -C alkylamino" herein means an amino group in which either hydrogen atom is replaced with a previously mentioned alkyl group containing from a to b carbon atoms, such as methylamino, ethylamino, n-propylamino, i-propylamino, n- butylamino, i-butylamino or tert-butylamino, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkylamino" herein means an amino group in which either hydrogen atom is replaced with a previously mentioned haloalkyl group containing from a to b carbon atoms, such as 2,2,2-trifluoroethylamino, 2-chloro-2,2- difluoroethylamino or 3,3,3-trifluoropropylamino, and those within the designated carbon number range are selected.

The expression "di(C -C ) alkylamino" herein means an amino group in which both hydrogen atoms are replaced with previously mentioned alkyl groups containing from a to b carbon atoms which may be identical with or different from each other, such as dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i- propyl(methyl)amino, di(n-propyl)amino or di(n-butyl)amino, and those within the designated carbon number range are selected.

The expression "di(Ca-Cb) haloalkylamino" herein means an amino group in which both hydrogen atoms are replaced with previously mentioned haloalkyl groups containing from a to b carbon atoms which may be identical with or different from each other, such as bis(2,2,2-trifluoroethyl)amino, and those within the designated carbon number range are selected.

The expression "C -C alkylcarbonyl" herein means an alkyl-C(O)- group in which the alkyl means a previously mentioned alkyl group containing from a to b carbon atoms, such as acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl or heptanoyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkylcarbonyl" herein means a haloalkyl-C(O)- group in which the haloalkyl means a previously mentioned haloalkyl group containing from a to b carbon atoms, such as fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, heptafluorobutanoyl or 3-chloro-2,2-dimethylpropanoyl, and those within the designated carbon number range are selected.

The expression "C -C alkoxycarbonyl" herein means an alkyl-O-C(O)- group in which the alkyl means a previously mentioned alkyl group containing from a to b carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i- propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert- butoxycarbonyl or 2-ethylhexyloxycarbonyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb haloalkoxycarbonyl" herein means a haloalkyl-O-C(O)- group in which the haloalkyl means a previously mentioned haloalkyl group containing from a to b carbon atoms, such as chloromethoxycarbonyl, 2-chloroethoxycarbonyl, 2,2- difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl or 2,2,2-trichloroethoxycarbonyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkylaminocarbonyl" herein means a carbamoyl group in which either hydrogen atom is replaced with a previously mentioned alkyl group containing from a to b carbon atoms, such as methylcarbamoyl, ethylcarbamoyl, n- propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s- butylcarbamoyl or tert-butylcarbamoyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkylaminocarbonyl" herein means a carbamoyl group in which either hydrogen atom is replaced with a previously mentioned haloalkyl group containing from a to b carbon atoms, such as 2-fluoroethylcarbamonyl, 2- chloroethylcarbamoyl, 2,2-difluoroethylcarbamoyl or 2-trifluoroethylcarbamoyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkylaminothiocarbonyl" herein means an amino-C(=S)- group in which either hydrogen atom is replaced with a previously mentioned alkyl group containing from a to b carbon atoms, such as methylthiocarbamoyl, ethylthiocarbamoyl, n-propylthiocarbamoyl, i-propylthiocarbamoyl, n-butylthiocarbamoyl, i-butylthiocarbamoyl, s-butylthiocarbamoyl or tert-butylthiocarbamoyl, and those within the designated carbon number range are selected.

The expression "C -C haloalkylaminothiocarbonyl" herein means an amino- C(=S)- group in which either hydrogen atom is replaced with a previously mentioned haloalkyl group containing from a to b carbon atoms, such as 2-fluoroethylthiocarbamoyl, 2-chloroethylthiocarbamoyl, 2,2-difluoroethylthiocarbamoyl or 2- trifluoroethylthiocarbamoyl, and those within the designated carbon number range are selected.

The expression "Ca-Cb alkylaminosulfonyl" herein means a sulfamoyl group in which either hydrogen atom is replaced with a previously mentioned alkyl group containing from a to b carbon atoms, such as methylsulfamoyl, ethylsulfamoyl, n- propylsulfamoyl, i-propylsulfamoyl, n-butylsulfamoyl, i-butylsulfamoyl, s-butylsulfamoyl or tert-butylsulfamoyl, and those within the designated carbon number range are selected.

The expression "di(Ca-Cb) alkylaminosulfonyl" herein means a sulfamoyl group in which both hydrogen atoms are replaced with previously mentioned alkyl groups containing from a to b carbon atoms which may be identical with or different from each other, such as N,N-dimethylsulfamoyl, N-ethyl-N-methylsulfamoyl, N,N-diethylsulfamoyl, N,N-di(n-propyl)sulfamoyl or N,N-di(n-butyl)sulfamoyl, and those within the designated carbon number range are selected.

The expression "heterocyclyl" herein may, for example, be specifically thiophen yl, thiophenyl, furanyl, furanyl, pyrrolyl, pyrrolyl, pyrrolyl, oxazolyl, oxazolyl, oxazolyl, isoxazolyl, isoxazolyl, isoxazolyl, isoxazolinyl, isoxazolinyl, isoxazolinyl, thiazolyl, thiazolyl, thiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, pyrazolyl, pyrazolyl, pyrazolyl, pyrazolyl, imidazolyl, imidazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,4-triazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3- thiadiazolyl, 1,2,3-triazolyl, 1,2,3-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, 1,2,3,4-tetrazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyridinyl, pyridinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4-triazinyl, 1,2,4-triazinyl, benzothiophen yl, benzothiophenyl, benzothiophenyl, benzothiophenyl, benzothiophenyl, benzothiophenyl, benzofuranyl, benzofuranyl, benzofuranyl, benzofuranyl, benzofuranyl, benzofuranyl, indolyl, indolyl, indolyl, indolyl, indolyl, indolyl, indolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzimidazolyl, benzimidazolyl, benzimidazolyl, benzimidazolyl, benzimidazolyl, benzimidazolyl, benzisoxazolyl, benzisoxazolyl, benzisoxazolyl, benzisoxazolyl, benzisoxazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, indazolyl, indazolyl, indazolyl, indazol- -yl, indazolyl, indazolyl, benzoxazolyl, benzoxazolyl, benzoxazolyl, benzoxazolyl, benzoxazolyl, quinolinyl, quinolinyl, quinolinyl, quinolinyl, quinolinyl, quinolinyl, quinolinyl, isoquinolinyl, isoquinolinyl, isoquinolinyl, isoquinolinyl, isoquinolinyl, isoquinolinyl, isoquinolinyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phthalazinyl, phthalazinyl, phthalazinyl, phthalazinyl, phthalazinyl, phthalazinyl, cinnolinyl, cinnolinyl, cinnolinyl, cinnolinyl, cinnolinyl, cinnolinyl, quinazolinyl, quinazolinyl, quinazolinyl, quinazolinyl, quinazolin- 7-yl or quinazolinyl.

The expression such as "Ca-Cb cycloalkyl (Cd-Ce) alkyl", "Ca-Cb halocycloalkyl (Cd- C ) alkyl" or "hydroxy (C -C ) alkyl" herein means a previously mentioned alkyl group e d e containing from d to e carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with an optional previously mentioned Ca-Cb cycloalkyl, Ca-Cb halocycloalkyl or hydroxy, and those within the designated carbon number range are selected.

The expression such as "(C -C ) alkyl optionally substituted with R ", "(C -C ) a b 1 6 1a-a a alkyl optionally substituted with A " or "(C1-C6) alkyl optionally substituted with Y " herein means a previously mentioned alkyl group having from a to b carbon atoms in 1a 1a-a which hydrogen atom(s) on carbon(s) are optionally substituted with optional R , A or Y , and those within the designated carbon number range are selected. When there 1a 1a-a a 1a 1a-a a are two or more R ’s, A ’s or Y ’s on (Ca-Cb) alkyl, each R , A or Y may be identical with or different from one another. 1a-a The expression such as "(C -C ) haloalkyl optionally substituted with A " or "(C - a b a Cb) haloalkyl optionally substituted with Y " herein means a previously mentioned haloalkyl group having from a to b carbon atoms in which hydrogen atom(s) or halogen 1a-a a atom(s) on carbon atom(s) are optionally substituted with optional A or Y , and those within the designated carbon number range are selected. When there are two or more 1a-a a 1a-a a A ’s or Y ’s on (Ca-Cb) haloalkyl, each A or Y may be identical with or different from one another.

The expression such as "(C -C ) alkenyl optionally substituted with Y " herein means a previously mentioned alkenyl group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (C -C ) alkenyl, each Y may be identical with or different from one another.

The expression such as "(Ca-Cb) alkynyl optionally substituted with Y " herein means a previously mentioned alkynyl group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (C -C ) alkynyl, each Y may be identical with or different from one another.

The expression such as "(Ca-Cb) alkoxy optionally substituted with Y " herein means a previously mentioned alkoxy group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (Ca-Cb) alkoxy, each Y may be identical with or different from one another.

The expression such as "(Ca-Cb) alkenyloxy optionally substituted with Y " herein means a previously mentioned alkenyloxy group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (C -C ) alkenyloxy, each Y may be identical with or different from one another.

The expression such as "(Ca-Cb) alkynyloxy optionally substituted with Y " herein means a previously mentioned alkynyloxy group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (Ca-Cb) alkynyloxy, each Y may be identical with or different from one another.

The expression "(C -C ) alkylthio optionally substituted with R ", "(C -C ) alkylthio a b a b 4a a optionally substituted with R " or "(C -C ) alkylthio optionally substituted with Y " herein means a previously mentioned alkylthio group having from a to b carbon atoms in which 3a 4a hydrogen atom(s) on carbon atom(s) are optionally substituted with optional R , R or Y , and those within the designated carbon number range are selected. When there 3a 4a a 3a 4a a are two or more R ’s, R ’s or Y ’s on (Ca-Cb) alkylthio, each R , R or Y may be identical with or different from one another.

The expression such as "(C -C ) alkylsulfinyl optionally substituted with Y " herein means a previously mentioned alkylsulfinyl group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (Ca-Cb) alkylsulfinyl, each Y may be identical with or different from one another.

The expression such as "(C -C ) alkylsulfonyl optionally substituted with Y " herein means a previously mentioned alkylsulfonyl group having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally substituted with optional Y , and those within the designated carbon number range are selected. When there are two or more Y ’s on (C -C ) alkylsulfonyl, each Y may be identical with or different from one another.

The expression "phenyl optionally substituted with R ", "phenyl optionally 4b c substituted with R " or "phenyl optionally substituted with Y " herein means a previously mentioned phenyl in which hydrogen atom(s) on carbon atom(s) are optionally 3b 4b c 3b 4b c substituted with optional R , R or Y . When there are two or more R ’s, R ’s or Y ’s 3b 4b c on phenyl, each R , R or Y may be identical with or different from one another.

The expression such as "heterocyclyl optionally substituted with R ", "heterocyclyl 4b c optionally substituted with R " or "heterocyclyl optionally substituted with Y " herein means a heterocyclic group in which hydrogen atom(s) on carbon atom(s) or nitrogen 3b 4b c atom(s) are optionally substituted with optional R , R or Y . When there are two or 3b 4b c 3b 4b c more R ’s, R ’s or Y ’s, each R , R or Y may be identical with or different from one another.

Now, a process for producing the compound described herein represented by the above formula (1) will be described below.

The compounds described herein may be produced, for example, by the following Processes 1 to 17.

Process 1 1a 2 3 4 5 A compound represented by the formula (2Q1-a) (wherein A , A , A , A and A are the same as defined above) and a compound represented by the formula (3D-a) (wherein R , D and n are the same as defined above) are reacted in a solvent or without solvent, as the case requires, in the presence of a dehydration condensation agent, and as the case requires, in the presence of a catalyst to produce a compound represented 1 1a 2 3 4 5 by the formula (4-a) (wherein R , A , A , A , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2- dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2- dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a dehydration condensation agent. The dehydration condensation agent to be used may, for example, be 1H- benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N’- dicyclohexylcarbodiimide, 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride or 2-chloromethylpyridinium iodide. The equivalent amount of the hehydration condensation agent used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (2Q1-a).

The reaction may be carried out in the presence of a catalyst. The catalyst to be used may, for example, be 1-hydroxybenzotriazole or 4-(dimethylamino)pyridine. The equivalent amount of the catalyst used is from 0.005 to 20 quivalent amount, preferably from 0.1 to 5 equivalent amount based on the compound represented by the formula (2Q1-a).

The reaction temperature may be set at an optional temperature of from -80 C to the refluxing temperature of the reaction mixture, and is preferably within a range of from 0 C to the refluxing temperature of the reaction mixture.

The reaction time varies depending upon the concentration of the reaction substrate and the reaction temperature, and is optionally set usually within a range of from 5 minutes to 100 hours, and is preferably from 1 to 48 hours.

With respect to the equivalent amount of the reaction substrate, the compound (3D-a) may be used in an amount of from 0.5 to 50 equivlant amount, preferably from 1 to 20 equivalent amount based on the compound (2Q1-a).

Further, the compound represented by the formula (4-a) may be produced by reacting the compound represented by the formula (2Q1-a) and a compound represented by the formula (3D-b) (wherein R , D and n are the same as defined above) in a solvent or without solvent, and as the case requires, in the presence of a base. In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate or cesium carbonate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (2Q1-a).

With respect to the equivalent amount of the reaction substrate, the compound (3D-b) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (2Q1-a).

Then, the compound represented by the formula (4-a) is subjected to dehydration condensation in a solvent or without solvent, as the case requires, in the presence of an acid, and as the case requires, in the presence of a dehydration agent to produce a 1 1a 2 3 4 5 compound represented by the formula (1-a) (wherein R , A , A , A , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4- dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of an acid. The acid to be used may, for example, be p-toluenesulfonic acid, polyphosphoric acid, acetic acid or propionic acid. The equivalent amount of the acid used is from 0.1 to 1,000 equivelent amount, preferably from 1 to 500 equivalent amount based on the compound represented by the formula (4-a).

The reaction may be carried out in the presence of a dehydration agent. The dehydration agent to be used may, for example, be phosphorus oxychloride or acetic anhydride. The equivalent amount of the dehydration agent used is from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (4-a).

Some of compounds represented by the formula (2Q1-a) are known compounds, and some of them are commercially available. The rest of them may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 4.

The compound represented by the formula (3D-a) may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 1 or Reaction Scheme 2.

The compound represented by the formula (3D-b) may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 1.

Process 2 1 2 3 4 5 A compound represented by the formula (1-f) (wherein R , A , A , A , A , D and n are the same as defined above) and a compound represented by the formula (16) (wherein A is C -C alkyl, and X is a leaving group such as a halogen atom, C -C 1 6 1 1 4 alkylsulfonate (such as methanesulfonyloxy), C -C haloalkylsulfonate (such as trifluoromethanesulfonyloxy) or arylsulfonate (such as benzenesulfonyloxy or p- toluenesulfonyloxy)) are reacted in a solvent or without solvent, and as the case requires, in the presence of a base, to produce a compound represented by the formula 1 1aa 2 3 4 5 (1-g) (wherein R , A , A , A , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate or cesium carbonate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (1- The reaction temperature may be set at an optional temperature of from -80 C to the refluxing temperature of the reaction mixture, and is preferably within a range of from 0 C to the refluxing temperature of the reaction mixture.

With respect to the equivalent amount of the reaction substrate, the compound (16) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (1-f).

The compound represented by the formula (1-f) may be prepared in accordance with Process 1.

Some of the compounds represented by the formula (16) are known compounds, and some of them are commercially available.

Process 3 The compound represented by the formula (2Q1-a) and a compound represented by the formula (17-a) (wherein G1, G2, G3 and G4 are the same as defined above) are reacted in accordance with the method disclosed in step [A] of Process 1 to produce a 1a 2 3 4 5 compound represented by the formula (18-a) (wherein A , A , A , A , A , G , G , G and 1 2 3 G4 are the same as defined above).

Further, the compound represented by the formula (18-a) may be produced by reacting the compound represented by the formula (2Q1-a) and a compound represented by the formula (17-b) (wherein G , G , G and G are the same as defined 1 2 3 4 above) in accordance with the method disclosed in step [A] of Process 1.

Then, the compound represented by the formula (18-a) is subjected to dehydration condensation in accordance with the method disclosed in step [B] of 1a 2 Process 1 to produce a compound represented by the formula (19-a) (wherein A , A , 3 4 5 A , A , A , G , G , G and G are the same as defined above). 1 2 3 4 Then, the compound represented by the formula (19-a) is reacted with a compound represented by the formula (9) (wherein R is the same as defined above) and a halogenating agent in a solvent or without solvent to produce a compound 1 1a 2 3 4 5 represented by the formula (1-h) (wherein R , A , A , A , A , A , G , G , G and G are 1 2 3 4 the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4- dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The halogenating agent may, for example, be chlorine, bromine, iodine, N- chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5- dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin or 1,3-diiodo-5,5- dimethylhydantoin. The equivalent amount of the halogenating agent used is from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (19-a).

With respect to the equivalent amount of the reaction substrate, the compound (9) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (19-a).

Further, the compound represented by the formula (19-a) and a halogenating agent are reacted in a solvent or without solvent to produce a compound represented by 1a 2 3 4 5 the formula (23-a) (wherein A , A , A , A , A , G1, G2, G3 and G4 are the same as defined above, and X10 is a chlorine atom, a bromine atom or an iodine atom). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

Then, the compound represented by the formula (23-a) and a compound represented by the formula (24) (wherein R is the same as defined above) are reacted in a solvent or without solvent, and as the case requires, in the presence of a base, to 1 1a 2 3 4 5 produce a compound represented by the formula (1-h) (wherein R , A , A , A , A , A , G1, G2, G3 and G4 are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N- methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate or cesium carbonate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (23-a).

With respect to the equivalent amount of the reaction substrate, the compound (24) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (23-a).

Further, the compound represented by the formula (1-h) may be produced by reacting the compound represented by the formula (23-a) and the compound represented by the formula (9) in a solvent or without solvent, as the case requires, in the presence of a base, as the case requires, in the presence of a palladium catalyst, and as the case requires, in the presence of a ligand. In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N- methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a palladium catalyst. The palladium catalyst to be used may, for example, be palladium-carbon, palladium(II) chloride, palladium(II) acetate, bis(triphenylphosphine) palladium(II) dichloride, tetrakis(triphenylphosphine) palladium(0), bis(dibenzylideneacetone) palladium(0) or tris(dibenzylideneacetone) dipalladium(0). The equivalent amount of the palladium catalyst used may be from 0.005 to 20 equivalent amount, preferably from 0.01 to 5 equivalent amount based on the compouond (23-a).

The reaction may be carried out in the presence of a ligand. The ligand to be used may, for example, be 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene or 1,10- phenanthroline. The equivalent amount of the ligand used may be from 0.005 to 20 equivalent amount, preferably from 0.01 to 5 equivalent amount based on the compound (23-a).

With respect to the equivalent amount of the reaction substrate, the compound (9) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (23-a).

Some of the compounds represented by the formula (17-a) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (17-b) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (9) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (24) are known compounds, and some of them are commercially available.

Process 4 The compound represented by the formula (2Q1-a) is reacted with a compound represented by the formula (20-a) (wherein T1, G1, G2, G3 and G4 are the same as defined above) in accordance with the method disclosed in step [A] of Process 1 to 1a 2 3 4 5 produce a compound represented by the formula (21-a) (wherein A , A , A , A , A , T , G1, G2, G3 and G4 are the same as defined above).

Further, the compound represented by the formula (21-a) may be produced by reacting the compound represented by the formula (2Q1-a) and a compound represented by the formula (20-b) (wherein T , G , G , G and G are the same as 1 1 2 3 4 defined above) in accordance with the method disclosed in step [A] of Process 1.

Then, the compound represented by the formula (21-a) is subjected to hydration condensation in accordance with the method disclosed in step [B] of Process 1 to 1a 2 3 4 5 produce a compound represented by the formula (22-a) (wherein A , A , A , A , A , T , G1, G2, G3 and G4 are the same as defined above).

Then, the compound represented by the formula (22-a) is reacted in accordance with the method disclosed in step [C] of Process 3 or the method disclosed in steps [D] and [E] of Process 3 to produce a compound represented by the formula (1-i) (wherein 1 1a 2 3 4 5 R , A , A , A , A , A , T1, G1, G2, G3 and G4 are the same as defined above).

Some of the compounds represented by the formula (20-a) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (20-b) are known compounds, and some of them are commercially available.

Process 5 2 3 4 5 A compound represented by the formula (2Q1-b) (wherein A , A , A and A are the same as defined above, and A is an oxygen atom or a sulfur atom) and a compound represented by the formula (3D-a) are reacted in accordance with the method disclosed in step [A] of Process 1 to produce a compound represented by the 1b 1 2 3 4 5 formula (4-b) (wherein A , R , A , A , A , A , D and n are the same as defined above).

Further, the compound represented by the formula (4-b) may be produced by reacting the compound represented by the formula (2Q1-b) and the compound represented by the formula (3D-b) in accordance with the method disclosed in step [A] of Process 1.

Then, the compound represented by the formula (4-b) is reacted in a solvent or without solvent, as the case requires, in the presence of an acid, and as the case requires, in the presence of a dehydration condensation agent to produce a compound 1b 1 2 3 4 5 represented by the formula (1-b) (wherein A , R , A , A , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2- dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2- dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of an acid. The acid to be used may, for example, be p-toluenesulfonic acid, polyphosphoric acid, acetic acid or propionic acid. The equivalent amount of the acid used is from 0.1 to 1,000 equivelent amount, preferably from 1 to 500 equivalent amount based on the compound represented by the formula (4-b).

The reaction may be carried out in the presence of a dehydration condensation agent. The dehydration condensation agent to be used may, for example, be a mixture of triphenylphosphine and bis(2-methoxyethyl) azodicarboxylate.

The equivalent amount of triphenylphosphine used is from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (4-b).

The equivalent amount of bis(2-methoxyethyl) azodicarboxylate used is from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (4-b).

Some of the compounds represented by the formula (2Q1-b) are known compounds, and some of them are commercially available.

Process 6 2 3 4 5 A compound represented by the formula (2Q2-a) (wherein A , A , A and A are the same as defined above) and a compound represented by the formula (3D-c) (wherein R , R , D and n are the same as defined above, and X is a chlorine atom, a bromine atom or an iodine atom) are reacted in the presence of a solvent or without solvent, and as the case requires, in the presence of a base to produce a compound 1 6 2 3 4 5 represented by the formula (1-c) (wherein R , R , A , A , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2- dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2- dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate or cesium carbonate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (2Q2-a).

Some of the compounds represented by the formula (2Q2-a) are known compounds, and some of them are commercially available. The rest of them may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 5.

The compound represented by the formula (3D-c) may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 1.

Process 7 1 2 3 4 5 A compound represented by the formula (1-j) (wherein R , A , A , A , A , D and n are the same as defined above) and a halogenating agent are reacted in a solvent or without solvent to produce a compound represented by the formula (1-k) (wherein R , 2 3 4 5 A , A , A , A , D and n are the same as defined above, and X is a chlorine atom, a bromine atom or an iodine atom). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The halogenating agent may, for example, be chlorine, bromine, iodine, N- chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5- dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin or 1,3-diiodo-5,5- dimethylhydantoin. The equivalent amount of the halogenating agent used is from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (1-j).

The compound represented by the formula (1-j) may be prepared in accordance with the method disclosed in Process 6.

Process 8 2 3 4 5 A compound represented by the formula (2Q3-a) (wherein R , R , A and A are the same as defined above) and a compound represented by the formula (3D-d) (wherein R , D and n are the same as defined above) are reacted in a solvent or without solvent, and as the case requires, in the presence of an acid to produce a compound 1 2 3 4 5 represented by the formula (40) (wherein R , R , R , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2- dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2- dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of an acid. The acid to be used may, for example, be acetic acid, formic acid or p-toluenesulfonic acid. The equivalent amount of the acid used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (2Q3-a).

With respect to the equivalent amount of the reaction substrate, the compound (3D-d) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (2Q3-a).

Then, the compound represented by the formula (40) and a phosphite are reacted in a solvent or without solvent to produce a compound represented by the formula (1-I) 1 2 3 4 5 (wherein R , R , R , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The phosphite may, for example, be trimethyl phosphite or triethyl phosphite.

The equivalent amount of the phophite used is from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (40).

Some of the compounds represented by the formula (2Q3-a) are known compounds, and some of them are commercially available. The rest of them may be prepared from known compounds in accordance with conventional methods disclosed in literature, for example, in accordance with the reaction conditions disclosed in Journal of Medicinal Chemistry, 2008, Vol. 50, p. 2468, WO2011/075628 or the like.

Some of the compounds represented by the formula (3D-d) are known compounds, and some of them are commercially available. The rest of them may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 6.

Process 9 2 3 4 5 A compound represented by the formula (2Q3-b) (wherein R , R , A and A are the same as defined above, and X3 is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom) and sodium azide are reacted in a solvent or without solvent to 2 3 4 5 produce a compound represented by the formula (2Q3-c) (wherein R , R , A and A are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4- dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

With respect to the equivalent amount of the reaction substrate, sodium azide may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (2Q3-b).

Then, the compound represented by the formula (2Q3-c) and the compound represented by the formula (3D-d) are reacted in a solvent or without solvent, as the case requires, in the presence of a base, and as the case requires, in the presence of a 1 2 3 4 catalyst to produce a compound represented by the formula (41) (wherein R , R , R , A , A , D and n are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N- methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate or cesium carbonate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (2Q3-c).

The reaction may be carried out in the presence of a catalyst. The catalyst to be used may, for example, be titanium tetrachloride. The equivalent amount of the catalyst used is from 0.005 to 20 equivalent amount, preferably from 0.1 to 5 equivalent amount based on the compound represented by the formula (2Q3-c).

With respect to the equivalent amount of the reaction substrate, the compound (3D-d) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (2Q3-c).

Then, the compound represented by the formula (41) is cyclized in a solvent or without solvent to produce a compound represented by the formula (1-m) (wherein R , 2 3 4 5 R , R , A , A , D and n are the same as defined above).

In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2- dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2- dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

Some of the compounds represented by the formula (2Q3-b) are known compounds, and some of them are commercially available. The rest of them may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 7.

Process 10 A compound represented by the formula (2Q4-a) (wherein R and A are the same as defined above) is reacted with the compound represented by the formula (3D-c) in accordance with the method disclosed in Process 6 to produce a compound 1 6 7 8 represented by the formula (1-n) (wherein R , R , R , A , D and n are the same as defined above).

Some of the compounds represented by the formula (2Q4-a) are known compounds, and some of them are commercially available. The rest of them may be prepared from known compounds in accordance with conventional methods disclosed in literature, for example, in accordance with the reaction conditions disclosed in Journal of Fluorine Chemistry, 2012, Vol. 133, p. 115, CN101768135, CN101885708 or the like.

Process 11 A compound represented by the formula (1-d) (wherein R , Q and D are the same as defined above) and an oxidizing agent are reacted in a solvent or without solvent, and as the case requires, in the presence of a catalyst to produce a compound represented by the formula (1-e) (wherein R , Q and D are the same as defined above, and n’ is an integer of 1 or 2). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4- dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’- dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, acetic acid, or a mixture thereof may be mentioned.

The oxidizing agent may, for example, be a peracid such as m-chloroperbenzoic acid or peracetic acid, hydrogen peroxide or OXONE (registered trademark by E. I. duPont, potassium peroxymonosulfate). The equivalent amount of the oxidizing agent used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (1-d).

The reaction may be carried out in the presence of a catalyst. The catalyst used may, for example, be sodium tungstate. The equivalent amount of the catalyst used is from 0.005 to 20 equivalent amount, preferably from 0.1 to 5 equivalent amount based on the compound represented by the formula (1-d).

The compound represented by the formula (1-d) may be prepared in accordance with the methods in Processes 1 to 10 or the following Processes 14 to 17.

Process 12 1 2 3 4 1 A compound represented by the formula (1-o) (wherein R , R , R , R , A , D and n are the same as defined above) is reacted with an oxidizing agent in accordance with the method disclosed in Process 11 to produce a compound represented by the formula 1 2 3 4 1 (1-p) (wherein R , R , R , R , A and D are the same as defined above).

The compound represented by the formula (1-o) may be prepared in accordance with the method disclosed in Processes 1 to 5.

Process 13 1 1 2 4 5 A compound represented by the formula (1-q) (wherein R , A , A , A , A , D and n are the same as defined above, and X is a chlorine atom, a bromine atom or an iodine atom) is reacted with a thiolating agent such as 2-ethylhexyl 3-mercaptopropionate, sodium hydrogen sulfide or sodium sulfide, for example, in accordance with the method disclosed in Organic Lett. 2007, Vol. 9, p. 3687, Tetrahedron 1998, Vol. 44, p. 1187, WO2011/159839 or the like to produce a compound represented by the formula (1-r) 1 1 2 4 5 (wherein R , A , A , A , A , D and n are the same as defined above).

Then, the compound represented by the formula (1-r) is reacted with a trifluoromethylating agent such as Umemoto reagent (5- (trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate) or Togni reagent (1- trifluoromethyl-3,3-dimethyl-1,2-benziodoxole), for example, in accordance with the method disclosed in WO2013/043962, WO2013/040863, WO2012/082566 or the like, to 1 1 2 4 5 produce a compound represented by the formula (1-s) (wherein R , A , A , A , A , D and n are the same as defined above).

Then, the compound represented by the formula (1-s) is reacted with an oxidizing agent in accordance with the method disclosed in Process 11 to produce a compound 1 1 2 4 5 represented by the formula (1-t) (wherein R , A , A , A , A , D and n are the same as defined above, and n’’ is an integer of 1 or 2).

The compound represented by the formula (1-q) may be prepared in accordance with the method disclosed in Processes 1 to 5.

Process 14 1a 4 5 2 3 A compound represented by the formula (2Q1-c) (wherein A , A , A , R and R are the same as defined above, and X11 is a chlorine atom, a bromine atom or an iodine atom) and a compound represented by the formula (3D-e) (wherein R , D and n are the same as defined above) are reacted in a solvent or without solvent, as the case requires, in the presence of a copper catalyst, as the case requires, in the presence of a base, and as the case requires, in the presence of a ligand. In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N- methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a copper catalyst. The copper catalyst to be used may, for example, be copper(I) iodide. The equivalent amount of the copper catalyst used is from 0.005 to 20 equivalent amount, preferably from 0.01 to 5 equivalent amount based on the compound (2Q1-c).

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate or potassium phosphate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (2Q1-c).

The reaction may be carried out in the presence of a ligand. The ligand to be used may, for example, be 1,10-phenanthroline, 1,2-diaminoethane or N,N’- dimethylethylenediamine. The equivalent amount of the ligand used is from 0.005 to 20 equivalent amount, preferably from 0.01 to 5 equivalent amount based on the compound (2Q1-c).

With respect to the equivalent amount of the reaction substrate, the compound (3D-e) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (2Q1-c).

Then, the compound represented by the formula (4-c) is subjected to dehydration condensation in accordance with the method disclosed in step [B] of Process 1 to 1a 4 5 1 2 3 produce a compound represented by the formula (1-u) (wherein A , A , A , R , R , R , D and n are the same as defined above).

Some of the compounds represented by the formula (2Q1-c) are known compounds, and some of them are commercially available. The rest of them may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 4.

The compound represented by the formula (3D-e) may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 8.

Process 15 2 3 1a 4 5 A compound represented by the formula (50) (wherein R , R , A , A and A are the same as defined above, and X is a chlorine atom, a bromine atom or an iodine atom) and a compound represented by the formula (5-a) (wherein G , G , G and G are 1 2 3 4 the same as defined above) are reacted in accordance with the method disclosed in 2 3 1a Process 6 to produce a compound represented by the formula (51) (wherein R , R , A , A , A , G , G , G and G are the same as defined above). 1 2 3 4 Then, the compound represented by the formula (51) and the compound represented by the formula (9) are reacted in accordance with the method disclosed in step [C] of Process 3 to produce a compound represented by the formula (1-v) (wherein 1 2 3 1a 4 5 R , R , R , A , A , A , G , G , G and G are the same as defined above). 1 2 3 4 Further, the compound represented by the formula (51) and a halogenating agent are reacted in accordance with the method disclosed in step [D] of Process 3 to produce 2 3 1a 4 5 a compound represented by the formula (52) (wherein R , R , A , A , A , G1, G2, G3, G4 and X are the same as defined above).

Then, the compound represented by the formula (52) and a compound represented by the formula (24) are reacted in accordance with the method disclosed in step [E] of Process 3 to produce a compound represented by the formula (1-v).

Further, the compound represented by the formula (1-v) may be produced by reacting the compound represented by the formula (52) and the compound represented by the formula (9) in accordance with the method disclosed in step [E] of Process 3.

The compound represented by the formula (50) may be prepared, for example, in accordance with the after-mentioned Reaction Scheme 9.

Some of the compounds represented by the formula (5-a) are known compounds, and some of them are commercially available.

Process 16 The compound represented by the formula (50) and the compound represented by the formula (9) are reacted in a solvent or without solvent, and as the case requires, in the presence of a base to produce a compound represented by the formula (53) 1 2 3 1a 4 5 (wherein R , R , R , A , A and A are the same as defined above). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate or cesium carbonate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (50).

With respect to the equivalent amount of the reaction substrate, the compound (9) may be used in an amount of from 0.5 to 50 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound (50).

Then, the compound represented by the formula (53) and a halogenating agent are reacted in a solvent or without solvent, as the case requires, in the presence of a silylating agent, as the case requires, in the presence of a base, as the case requires, in the presence of an acid to produce a compound represented by the formula (54) 1 2 3 1a 4 5 (wherein R , R , R , A , A and A are the same as defined above, and X13 is a chlorine atom, a bromine atom or an iodine atom). In a case where a solvent is used, the solvent used may be any solvent which is inert to the reaction, and for example, water, an aliphatic acid such as acetic acid, a lower alcohol such as methanol or ethanol, an ether such as diethyl ether, tetrahydrofuran, 1,4-dioxane or 1,2-dimethoxyethane, an aromatic hydrocarbon such as benzene, chlorobenzene, bromobenzene, xylene or toluene, an aliphatic hydrocarbon such as pentane, hexane or cyclohexane, a halogenated hydrocarbon such as dichloromethane, chloroform or 1,2-dichloroethane, a nitrile such as acetonitrile or propionitrile, an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N’-dimethylimidazolidinone, a sulfoxide such as dimethyl sulfoxide, a nitrogen-containing aromatic compound such as pyridine or quinoline, or a mixture thereof may be mentioned.

The halogenating agent may, for example, be chlorine, bromine, iodine, N- chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5- dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5- dimethylhydantoin or trimethylphenylammonium tribromide. The equivalent amount of the halogenating agent used is from 0.5 to 50 equivalent amount, preferably from 1 to equivalent amount based on the compound represented by the formula (53).

The reaction may be carried out in the presence of a silylating agent. The silylating agent to be used may, for example, be trimethylsilyl trifluoromethanesulfonate.

The equivalent amount of the silylating agent used is from 0.005 to 20 equivalent amount, preferably from 0.01 to 5 equivalent amount based on the compound represented by the formula (53).

The reaction may be carried out in the presence of a base. The base to be used may, for example, be an organic base such as pyridine, 2,6-lutidine, 4- dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU) or 1,5-diazabicyclo[4.3.0]nonene (DBN), or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate or potassium phosphate. The equivalent amount of the base used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (53).

The reaction may be carried out in the presence of an acid. The acid to be used may, for example, be hydrobromic acid or an acetic acid solution of hydrogen bromide.

The equivalent amount of the acid used is from 0.1 to 100 equivalent amount, preferably from 1 to 20 equivalent amount based on the compound represented by the formula (53).

Then, the compound represented by the formula (54) and the compound represented by the formula (5-a) are reacted in accordance with the method disclosed in Process 6 to produce a compound represented by the formula (1-v).

Process 17 The compound represented by the formula (54) and a compound represented by the formula (5-b) (wherein G and Y6 are the same as defined above) are reacted in accordance with the method disclosed in Process 6 to produce a compound 1 2 3 1a 4 5 represented by the formula (1-w) (wherein R , R , R , A , A , A , G5 and Y6 are the same as defined above).

In Processes 1 to 17, the reaction mixture after the reaction can be worked up by an ordinary procedure such as direct concentration, concentration of a solution in an organic solvent after washing with water, pouring into ice-water or extraction with an organic solvent followed by concentration to obtain the desired compound described herein. Further, if necessary, the desired product may be isolated or purified by an optional purification method such as recrystallization, column chromatography, thin layer chromatography or liquid chromatography. Otherwise, the compound described herein may be subjected to the next step without isolation and purification. In some cases, the dehydration condensation reaction as the subsequent step proceeds in step [A] of Process 1, in step [A] of Process 3, in step [A] of Process 4, in step [A] of Process 5 and in step [A] of Process 14, and thus step [B] may be omitted.

Among the compounds represented by the formulae (3D-a) and (3D-b) used in Processes 1 and 5, compounds represented by the formulae (3D-a1) and (3D-b1) wherein n is an integer of 0, and among the compounds represented by the formula (3D-c) used in Processes 6 and 10, a compound represented by the formula (3D-c1) wherein n is an integer of 1 or 2 and a compound represented by the formula (3D-c2) wherein n is an integer of 0, may be produced, for example, in accordance with the following Reaction Scheme 1.

Reaction Scheme 1 The compound represented by the formula (5-a) is reacted with a compound represented by the formula (6) (wherein Ra is C1-C6 alkyl) in accordance with the method disclosed in Process 6 to produce a compound represented by the formula (7-a) (wherein G , G , G and G are the same as defined above, and Ra is C -C alkyl). 1 2 3 4 1 6 Then, the compound represented by the formula (7-a) is reacted with a halogenating agent in accordance with the method disclosed in Process 7 to produce a compound represented by the formula (8-a) (wherein G , G , G and G are the same 1 2 3 4 as defined above, Ra is C -C alkyl, and X is a chlorine atom, a bromine atom or an 1 6 5 iodine atom).

Then, the compound represented by the formula (8-a) is reacted with a compound represented by the formula (9) (wherein R is the same as defined above) in accordance with the method disclosed in step [E] of Process 3 to produce a compound represented by the formula (10-a) (wherein G1, G2, G3, G4 and R are the same as defined above, and Ra is C -C alkyl).

Then, the compound represented by the formula (10-a) is hydrolyzed in accordance with conventional methods disclosed in literature to produce a compound represented by the formula (3D-a1) (wherein G1, G2, G3, G4 and R are the same as defined above).

Then, the compound represented by the formula (3D-a1) is reacted with a chlorinating agent in accordance with conventional methods disclosed in literature to produce a compound represented by the formula (3D-b1) (wherein G1, G2, G3, G4 and R are the same as defined above).

Then, the compound represented by the formula (3D-b1) and N,O- dimethylhydroxylamine represented by the formula (11) or its hydrochloride are reacted, as the case requires, in the presence of a base to produce a compound represented by the formula (12) (wherein G , G , G , G and R are the same as defined above). 1 2 3 4 Then, the compound represented by the formula (12) and a Grignard reagent represented by the formula (13) (wherein R is the same as defined above, and X7 is a chlorine atom, a bromine atom or an iodine atom) are reacted in accordance with conventional methods disclosed in literature to produce a compound represented by the formula (14) (wherein G1, G2, G3, G4, R and R are the same as defined above).

Then, the compound represented by the formula (14) and an oxidizing agent are reacted in accordance with the method disclosed in Process 11 to produce a compound represented by the formula (15) (wherein G1, G2, G3, G4, R , R and n’ are the same as defined above).

Then, the compound represented by the formula (15) is reacted with a halogenating agent in accordance with the method disclosed in step [B] of Process 16 to produce a compound represented by the formula (3D-c1) (wherein G1, G2, G3, G4, R , R , X and n’ are the same as defined above).

Further, the compound represented by the formula (14) is reacted with a halogenating agent in accordance with the method disclosed in step [B] of Process 16 to produce a compound represented by the formula (3D-c2) (wherein G1, G2, G3, G4, R , R and X are the same as defined above).

Some of the compounds represented by the formula (6) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (13) are known compounds, and some of them are commercially available.

Among the compounds represented by the formula (3D-a) used in Process 1, a compound represented by the formula (3D-a2) wherein n is an integer of 0 may be produced, for example, in accordance with the following Reaction Scheme 2.

Reaction Scheme 2 The compound represented by the formula (5-b) is reacted with the compound represented by the formula (6) in accordance with the method disclosed in Process 6 to produce a compound represented by the formula (7-b) (wherein G5, Y6 and Ra are the same as defined above).

Then, the compound represented by the formula (7-b) is reacted with a halogenating agent in accordance with the method disclosed in Process 7 to produce a compound represented by the formula (8-b) (wherein G5, Y6 and Ra are the same as defined above, and X6 is a chlorine atom, a bromine atom or an iodine atom).

Then, the compound represented by the formula (8-b) is reacted with the compound represented by the formula (9) in accordance with the method disclosed in step [E] of Process 3 to produce a compound represented by the formula (10-b) (wherein G5, Y6, R and Ra are the same as defined above).

Then, the compound represented by the formula (10-b) is hydrolyzed in accordance with conventional methods disclosed in literature to produce a compound represented by the formula (3D-a2) (wherein G5, Y6 and R are the same as defined above).

Some of the compounds represented by the formula (5-b) are known compounds, and some of them are commercially available.

The compound represented by the formula (10-a) used in Reaction Scheme 1 may be produced, for example, in accordance with the following Reaction Scheme 3.

Reaction Scheme 3 The compound represented by the formula (7-a) is reacted with the compound represented by the formula (9) and a halogenating agent in accordance with the method disclosed in step [C] of Process 3 to produce a compound represented by the formula (10-a).

Among the compounds represented by the formula (2Q1-a) used in Process 1, a compound represented by the formula (2Q1-a-1) may be produced, for example, in accordance with the following Reaction Scheme 4.

Reaction Scheme 4 2 3 5 A compound represented by the formula (25) (wherein R , R and A are the same as defined above) is reacted with a brominating agent such as N-bromosuccinimide, for example, in accordance with the method disclosed in WO2007/093901 to produce a 2 3 5 compound represented by the formula (26) (wherein R , R and A are the same as defined above).

Then, the compound represented by the formula (26) is reacted with the compound represented by the formula (16) in accordance with the method disclosed in 2 3 1aa Process 2 to produce a compound represented by the formula (27) (wherein R , R , A and A are the same as defined above).

Then, the compound represented by the formula (27) is reacted with an aminating agent such as ammonia, aqueous ammonia or lithium amide in accordance with the method disclosed in e.g. WO2012/086848 to produce a compound represented by the 2 3 1aa 5 formula (2Q1-a-1) (wherein R , R , A and A are the same as defined above).

Some of the compounds represented by the formula (25) are known compounds, and some of them are commercially available.

Among the compounds represented by the formula (2Q2-a) used in Process 6, a compound represented by the formula (2Q2-a-1) may be produced, for example, in accordance with the following Reaction Scheme 5.

Reaction Scheme 5 A compound represented by the formula (28) (wherein R and R are the same as defined above, and Rb is C -C alkyl) is reacted with a compound represented by the formula (29) (wherein Rc is C1-C6 alkyl, and X8 is a favorable leaving group such as a halogen atom, C1-C4 alkylsulfonate (such as methanesulfonyloxy), C1-C4 haloalkylsulfonate (such as trifluoromethanesulfonyloxy) or arylsulfonate (such as benzenesulfonyloxy or p-toluenesulfonyloxy)) for example in accordance with the method disclosed in e.g. Journal of Fluorine Chemistry, 1989, Vol. 44, p. 361, Journal of Heterocyclic Chemistry, 1993, Vol. 33, p. 49, or Synthesis 2000, p. 1078 to produce a compound represented by the formula (30) (wherein R , R , Rb and Rc are the same as defined above).

Then, the compound represented by the formula (30) is reacted with a compound represented by the formula (31) (wherein R is the same as defined above) in accordance with e.g. Bioorganic & Medicinal Chemistry Letters, 2011, Vol. 21, p. 1601 2 3 5 to produce a compound represented by the formula (32) (wherein R , R and R are the same as defined above).

Then, the compound represented by the formula (32) is reacted with a chlorinating agent such as phosphorus oxychloride, thionyl chloride or oxalyl chloride for example in accordance with e.g. WO2012/061337 or WO2005/033084 to produce a compound 2 3 5 represented by the formula (33) (wherein R , R and R are the same as defined above).

Then, the compound represented by the formula (33) is reacted with aqueous ammonia for example in accordance with the method disclosed in e.g. WO2012/061337 or WO2005/033084 to produce a compound represented by the formula (2Q2-a-1).

Some of the compounds represented by the formula (28) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (29) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (31) are known compounds, and some of them are commercially available.

The compound represented by the formula (3D-d) used in Process 8 may be produced, for example, in accordance with the following Reaction Scheme 6.

The compound represented by the formula (3D-a) is reacted with diphenylphosphoryl azide (DPPA) and a compound represented by the formula (34) (wherein Rd is C -C alkyl) for example in accordance with the method disclosed in e.g.

WO2012/174312 or WO2013/018021 to produce a compound represented by the formula (3D-d-1) (wherein R , Rd, D and n are the same as defined above).

Then, the compound represented by the formula (3D-d-1) is reacted with an acid for example in accordance with the method disclosed in e.g. WO2012/174312 or WO2003/018021 to produce a compound represented by the formula (3D-d).

Among the compounds represented by the formula (2Q3-b) used in Process 9, a compound represented by the formula (2Q3-b-1) may be produced, for example, in accordance with the following Reaction Scheme 7.

Reaction Scheme 7 2 3 5 A compound represented by the formula (35) (wherein R , R and R are the same as defined above) is halogenated by using a halogenating agent for example in accordance with the method disclosed in e.g. WO2013/064460 or WO2013/064461 to 2 3 5 produce a compound represented by the formula (36) (wherein R , R , R and X are the same as defined above).

Then, the compound represented by the formula (36) is reduced for example in accordance with the method disclosed in e.g. WO2013/064460 or WO2013/064461 to 2 3 5 produce a compound represented by the formula (37) (wherein R , R , R and X are the same as defined above).

Then, the compound represented by the formula (37) is oxidized for example in accordance with the method disclosed in e.g. WO2013/064460 or WO2013/064461 to 2 3 5 produce a compound represented by the formula (2Q3-b-1) (wherein R , R , R and X3 are the same as defined above).

Some of the compounds represented by the formula (35) are known compounds, and some of them are commercially available. The rest of them may be prepared from known compounds in accordance with conventional methods disclosed in literature, for example, in accordance with the reaction conditions disclosed in e.g. WO2000/039094.

Among the compounds represented by the formula (3D-e) used in Process 14, a compound represented by the formula (3D-e1) wherein n is an integer of 0 may be produced, for example, in accordance with the following Reaction Shceme 8.

Reaction Shceme 8 The compound represented by the formula (3D-b1) is reacted with aqueous ammonia for example in accordance with the method disclosed in e.g. JP-A 108046 to produce a compound represented by the formula (3D-e1) (wherein R , G1, G2, G and G are the same as defined above).

The compound represented by the formula (50) used in Processes 15 and 16 may be produced, for example, in accordance with the following Reaction Scheme 9.

Reaction Scheme 9 A compound represented by the formula (2Q1-d) is reacted with compound represented by the formula (55) in accordance with the method disclosed in step [A] of 2 3 1a Process 1 to produce a compound represented by the formula (56) (wherein R , R , A , A and A are the same as defined above).

Then, the compound represented by the formula (56) is subjected to deacetylation for example in accordance with the method disclosed in e.g. Synthesis, 1991, p. 465 to 2 3 1a 4 5 produce a compound represented by the formula (57) (wherein R , R , A , A and A are the same as defined above).

Then, the compound represented by the formula (57) is subjected to dehydration condensation in accordance with the method disclosed in step [B] of Process 1 to 2 3 1a 4 5 produce a compound represented by the formula (58) (wherein R , R , A , A and A are the same as defined above).

Then, the compound represented by the formula (58) and an oxidizing agent are reacted for example in accordance with the method disclosed in e.g. Journal of Medicinal Chemistry, 1998, Vol. 31, p. 545 to produce a compound represented by the 2 3 1a 4 5 formula (59) (wherein R , R , A , A and A are the same as defined above).

Then, the compound represented by the formula (59) and a halogenating agent are reacted in accordance with the method disclosed in step [B] of Process 16 or in accordance with the method disclosed in e.g. Journal of Medicinal Chemistry, 1988, Vol. 31, p. 656 or Journal of Medicinal Chemistry, 2005, Vol. 48, p. 7658 to produce a compound represented by the formula (50).

The compound represented by the formula (55) is a known compound and is commercially available. Further, the compound represented by the formula (55) has optically active isomers due to the presence of an asymmetric carbon atom, and the present invention covers any optical isomers and any racemates.

In each reaction, after the reaction, an ordinary post treatment is carried out to obtain respective production intermediates to be raw material compounds in Processes 1 to 17.

Further, each production intermediate produced by the above methods may be used for the reaction in the subsequent step as it is without isolation nor purification. In some cases, the dehydration condensation reaction as the subsequent step proceeds, in step [B] of Reaction Scheme 9, and thus step [C] may be omitted.

As the condensed heterocyclic compounds represented by the formula (1) described herein, which can be produced by the above methods, compounds represented by the following Tables 1 to 5 may be mentioned. However, the compounds shown in the following Tables 1 to 5 merely exemplify the compounds described herein, and the present invention is by no means restricted thereto.

In Tables, Me represents methyl, and similarly, Et represents ethyl, Pr represents normal propyl, and Pr represents isopropyl.

Table 1 Table 1 (Continued) ［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y3 Y4 n CF Me HH HH 0 CF Me HNO HH 1 3 3 2 CF Me HH HH 1 CF Me HNO HH 2 3 3 2 CF Me HH HH 2 CF Me HCNH H 0 CF Me FH HH 0 CF Me HCNH H 1 CF Me FH HH 1 CF Me HCNH H 2 CF Me FH HH 2 CF Me HH FH 0 CF Me Cl H H H 0 CF Me HH FH 1 CF Me Cl H H H 1 CF Me HH FH 2 CF Me Cl H H H 2 CF Me HH Cl H 0 CF Me Br H H H 0 CF Me HH Cl H 1 CF Me Br H H H 1 CF Me HH Cl H 2 CF Me Br H H H 2 CF Me HH Br H 0 CF Me IH HH 0 CF Me HH Br H 1 CF Me IH HH 1 CF Me HH Br H 2 CF Me IH HH 2 CF Me HH IH 0 CF Me Me H H H 0 CF Me HH IH 1 CF Me Me H H H 1 CF Me HH IH 2 CF Me Me H H H 2 CF Me HH Me H 0 CF Me CF HH H 0 CF Me HH Me H 1 3 3 3 CF Me CF HH H 1 CF Me HH Me H 2 3 3 3 CF Me CF HH H 2 CF Me HH CF H 0 3 3 3 3 CF Me HF HH 0 CF Me HH CF H 1 3 3 3 CF Me HF HH 1 CF Me HH CF H 2 3 3 3 CF Me HF HH 2 CF Me HH CF CF H 0 3 3 2 3 CF Me HClH H 0 CF Me HH CF CF H 1 3 3 2 3 CF Me HClH H 1 CF Me HH CF CF H 2 3 3 2 3 CF Me HClH H 2 CF Me H H CF(CF ) H 0 3 3 3 2 CF Me HBrH H 0 CF Me H H CF(CF ) H 1 3 3 3 2 CF Me HBrH H 1 CF Me H H CF(CF ) H 2 3 3 3 2 CF Me HBrH H 2 CF Me HH SMe H 0 CF Me HI HH 0 CF Me HH SMe H 1 CF Me HI HH 1 CF Me HH SMe H 2 CF Me HI HH 2 CF Me H H SOMe H 0 CF Me HMeH H 0 CF Me H H SOMe H 1 CF Me HMeH H 1 CF Me H H SOMe H 2 CF Me HMeH H 2 CF Me HH SO Me H 0 3 3 2 CF Me HCF HH 0 CF Me HH SO Me H 1 3 3 3 2 CF Me HCF HH 1 CF Me HH SO Me H 2 3 3 3 2 CF Me HCF HH 2 CF Me HH OMe H 0 3 3 3 CF Me HCF CF HH 0 CF Me HH OMe H 1 3 2 3 3 CF Me HCF CF HH 1 CF Me HH OMe H 2 3 2 3 3 CF Me HCF CF HH 2 CF Me H H OCF H 0 3 2 3 3 3 CF Me H CF(CF ) HH 0 CF Me H H OCF H 1 3 3 2 3 3 CF Me H CF(CF ) HH 1 CF Me H H OCF H 2 3 3 2 3 3 CF Me H CF(CF ) HH 2 CF Me HH NO H 0 3 3 2 3 2 CF Me HSMe H H 0 CF Me HH NO H 1 3 3 2 CF Me HSMe H H 1 CF Me HH NO H 2 3 3 2 CF Me HSMe H H 2 CF Me HH CN H 0 CF Me H SOMe H H 0 CF Me HH CN H 1 CF Me H SOMe H H 1 CF Me HH CN H 2 CF Me H SOMe H H 2 CF Me HH HF 0 CF Me HSO Me H H 0 CF Me HH HF 1 3 2 3 CF Me HSO Me H H 1 CF Me HH HF 2 3 2 3 CF Me HSO Me H H 2 CF Me HH H Cl 0 3 2 3 CF Me HOMe H H 0 CF Me HH H Cl 1 CF Me HOMe H H 1 CF Me HH H Cl 2 CF Me HOMe H H 2 CF Me HH H Br 0 CF Me H OCF HH 0 CF Me HH H Br 1 3 3 3 CF Me H OCF HH 1 CF Me HH H Br 2 3 3 3 CF Me H OCF HH 2 CF Me HH HI 0 3 3 3 CF Me HNO HH 0 CF Me HH HI 1 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y3 Y4 n CF Me HH HI 2 CF Me HClH I 0 CF Me HH H Me 0 CF Me HClH I 1 CF Me HH H Me 1 CF Me HClH I 2 CF Me HH H Me 2 CF Me HBrH F 0 CF Me HH H CF 0 CF Me HBrH F 1 3 3 3 CF Me HH H CF 1 CF Me HBrH F 2 3 3 3 CF Me HH H CF 2 CF Me HBrH Cl 0 3 3 3 CF Me HH H CF CF 0 CF Me HBrH Cl 1 3 2 3 3 CF Me HH H CF CF 1 CF Me HBrH Cl 2 3 2 3 3 CF Me HH H CF CF 2 CF Me HBrH I 0 3 2 3 3 CF Me H H H CF(CF ) 0 CF Me HBrH I 1 3 3 2 3 CF Me H H H CF(CF ) 1 CF Me HBrH I 2 3 3 2 3 CF Me H H H CF(CF ) 2 CF Me HI H F 0 3 3 2 3 CF Me HH H SMe 0 CF Me HI H F 1 CF Me HH H SMe 1 CF Me HI H F 2 CF Me HH H SMe 2 CF Me HI H Cl 0 CF Me H H H SOMe 0 CF Me HI H Cl 1 CF Me H H H SOMe 1 CF Me HI H Cl 2 CF Me H H H SOMe 2 CF Me HI H Br 0 CF Me HH H SO Me 0 CF Me HI H Br 1 3 2 3 CF Me HH H SO Me 1 CF Me HI H Br 2 3 2 3 CF Me HH H SO Me 2 CF Me HF H CN 0 3 2 3 CF Me HH H OMe 0 CF Me HF H CN 1 CF Me HH H OMe 1 CF Me HF H CN 2 CF Me HH H OMe 2 CF Me HClH CN 0 CF Me H H H OCF 0 CF Me HClH CN 1 3 3 3 CF Me H H H OCF 1 CF Me HClH CN 2 3 3 3 CF Me H H H OCF 2 CF Me HBrH CN 0 3 3 3 CF Me HH H NO 0 CF Me HBrH CN 1 3 2 3 CF Me HH H NO 1 CF Me HBrH CN 2 3 2 3 CF Me HH H NO 2 CF Me HI H CN 0 3 2 3 CF Me HH H CN 0 CF Me HI H CN 1 CF Me HH H CN 1 CF Me HI H CN 2 CF Me HH H CN 2 CF Me HCF HF 0 3 3 3 CF Me HF HF 0 CF Me HCF HF 1 3 3 3 CF Me HF HF 1 CF Me HCF HF 2 3 3 3 CF Me HF HF 2 CF Me HCF HCl 0 3 3 3 CF Me HClH Cl 0 CF Me HCF HCl 1 3 3 3 CF Me HClH Cl 1 CF Me HCF HCl 2 3 3 3 CF Me HClH Cl 2 CF Me HCF HBr 0 3 3 3 CF Me HBrH Br 0 CF Me HCF HBr 1 3 3 3 CF Me HBrH Br 1 CF Me HCF HBr 2 3 3 3 CF Me HBrH Br 2 CF Me HCF HI 0 3 3 3 CF Me HI HI 0 CF Me HCF HI 1 3 3 3 CF Me HI HI 1 CF Me HCF HI 2 3 3 3 CF Me HI HI 2 CF Me HCF HCN 0 3 3 3 CF Me HF H Cl 0 CF Me HCF HCN 1 3 3 3 CF Me HF H Cl 1 CF Me HCF HCN 2 3 3 3 CF Me HF H Cl 2 CF Me HF F H 0 CF Me HF H Br 0 CF Me HF F H 1 CF Me HF H Br 1 CF Me HF F H 2 CF Me HF H Br 2 CF Me HCl ClH 0 CF Me HF HI 0 CF Me HCl ClH 1 CF Me HF HI 1 CF Me HCl ClH 2 CF Me HF HI 2 CF Me HBr BrH 0 CF Me HClH F 0 CF Me HBr BrH 1 CF Me HClH F 1 CF Me HBr BrH 2 CF Me HClH F 2 CF Me HI I H 0 CF Me HClH Br 0 CF Me HI I H 1 CF Me HClH Br 1 CF Me HI I H 2 CF Me HClH Br 2 CF Me HF Cl H 0 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Me HF Cl H 1 CF Et HHH H 0 CF Me HF Cl H 2 CF Et HHH H 1 CF Me HF Br H 0 CF Et HHH H 2 CF Me HF Br H 1 CF Et FHH H 0 CF Me HF Br H 2 CF Et FHH H 1 CF Me HFI H 0 CF Et FHH H 2 CF Me HFI H 1 CF Et Cl H H H 0 CF Me HFI H 2 CF Et Cl H H H 1 CF Me HClF H 0 CF Et Cl H H H 2 CF Me HClF H 1 CF Et Br H H H 0 CF Me HClF H 2 CF Et Br H H H 1 CF Me HCl Br H 0 CF Et Br H H H 2 CF Me HCl Br H 1 CF Et IHH H 0 CF Me HCl Br H 2 CF Et IHH H 1 CF Me HClI H 0 CF Et IHH H 2 CF Me HClI H 1 CF Et Me H H H 0 CF Me HClI H 2 CF Et Me H H H 1 CF Me HBrF H 0 CF Et Me H H H 2 CF Me HBrF H 1 CF Et CF HH H 0 3 3 3 CF Me HBrF H 2 CF Et CF HH H 1 3 3 3 CF Me HBr Cl H 0 CF Et CF HH H 2 3 3 3 CF Me HBr Cl H 1 CF Et HFH H 0 CF Me HBr Cl H 2 CF Et HFH H 1 CF Me HBrI H 0 CF Et HFH H 2 CF Me HBrI H 1 CF Et HClH H 0 CF Me HBrI H 2 CF Et HClH H 1 CF Me HIF H 0 CF Et HClH H 2 CF Me HIF H 1 CF Et HBrH H 0 CF Me HIF H 2 CF Et HBrH H 1 CF Me HI Cl H 0 CF Et HBrH H 2 CF Me HI Cl H 1 CF Et HIH H 0 CF Me HI Cl H 2 CF Et HIH H 1 CF Me HI Br H 0 CF Et HIH H 2 CF Me HI Br H 1 CF Et HMeH H 0 CF Me HI Br H 2 CF Et HMeH H 1 CF Me HF CN H 0 CF Et HMeH H 2 CF Me HF CN H 1 CF Et HCF HH 0 3 3 3 CF Me HF CN H 2 CF Et HCF HH 1 3 3 3 CF Me HCl CN H 0 CF Et HCF HH 2 3 3 3 CF Me HCl CN H 1 CF Et HCF CF HH 0 3 3 2 3 CF Me HCl CN H 2 CF Et HCF CF HH 1 3 3 2 3 CF Me HBr CN H 0 CF Et HCF CF HH 2 3 3 2 3 CF Me HBr CN H 1 CF Et H CF(CF ) HH 0 3 3 3 2 CF Me HBr CN H 2 CF Et H CF(CF ) HH 1 3 3 3 2 CF Me HI CN H 0 CF Et H CF(CF ) HH 2 3 3 3 2 CF Me HI CN H 1 CF Et H SMe H H 0 CF Me HI CN H 2 CF Et H SMe H H 1 CF Me HCF FH 0 CF Et H SMe H H 2 3 3 3 CF Me HCF FH 1 CF Et HSOMeH H 0 3 3 3 CF Me HCF FH 2 CF Et HSOMeH H 1 3 3 3 CF Me HCF Cl H 0 CF Et HSOMeH H 2 3 3 3 CF Me HCF Cl H 1 CF Et HSO Me H H 0 3 3 3 2 CF Me HCF Cl H 2 CF Et HSO Me H H 1 3 3 3 2 CF Me HCF Br H 0 CF Et HSO Me H H 2 3 3 3 2 CF Me HCF Br H 1 CF Et H OMe H H 0 3 3 3 CF Me HCF Br H 2 CF Et H OMe H H 1 3 3 3 CF Me HCF IH 0 CF Et H OMe H H 2 3 3 3 CF Me HCF IH 1 CF Et HOCF HH 0 3 3 3 3 CF Me HCF IH 2 CF Et HOCF HH 1 3 3 3 3 CF Me HCF CN H 0 CF Et HOCF HH 2 3 3 3 3 CF Me HCF CN H 1 CF Et HNO HH 0 3 3 3 2 CF Me HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Et HNO HH 1 CF Et HHH I 2 3 2 3 CF Et HNO HH 2 CF Et HHH Me 0 3 2 3 CF Et HCNH H 0 CF Et HHH Me 1 CF Et HCNH H 1 CF Et HHH Me 2 CF Et HCNH H 2 CF Et HHH CF 0 3 3 3 CF Et HHF H 0 CF Et HHH CF 1 3 3 3 CF Et HHF H 1 CF Et HHH CF 2 3 3 3 CF Et HHF H 2 CF Et HHH CF CF 0 3 3 2 3 CF Et HH Cl H 0 CF Et HHH CF CF 1 3 3 2 3 CF Et HH Cl H 1 CF Et HHH CF CF 2 3 3 2 3 CF Et HH Cl H 2 CF Et H H H CF(CF ) 0 3 3 3 2 CF Et HH Br H 0 CF Et H H H CF(CF ) 1 3 3 3 2 CF Et HH Br H 1 CF Et H H H CF(CF ) 2 3 3 3 2 CF Et HH Br H 2 CF Et HHH SMe 0 CF Et HHI H 0 CF Et HHH SMe 1 CF Et HHI H 1 CF Et HHH SMe 2 CF Et HHI H 2 CF Et HHH SOMe 0 CF Et HH Me H 0 CF Et HHH SOMe 1 CF Et HH Me H 1 CF Et HHH SOMe 2 CF Et HH Me H 2 CF Et HHH SO Me 0 3 3 2 CF Et HH CF H 0 CF Et HHH SO Me 1 3 3 3 2 CF Et HH CF H 1 CF Et HHH SO Me 2 3 3 3 2 CF Et HH CF H 2 CF Et HHH OMe 0 3 3 3 CF Et HH CF CF H 0 CF Et HHH OMe 1 3 2 3 3 CF Et HH CF CF H 1 CF Et HHH OMe 2 3 2 3 3 CF Et HH CF CF H 2 CF Et HHH OCF 0 3 2 3 3 3 CF Et H H CF(CF ) H 0 CF Et HHH OCF 1 3 3 2 3 3 CF Et H H CF(CF ) H 1 CF Et HHH OCF 2 3 3 2 3 3 CF Et H H CF(CF ) H 2 CF Et HHH NO 0 3 3 2 3 2 CF Et HH SMe H 0 CF Et HHH NO 1 3 3 2 CF Et HH SMe H 1 CF Et HHH NO 2 3 3 2 CF Et HH SMe H 2 CF Et HHH CN 0 CF Et H H SOMe H 0 CF Et HHH CN 1 CF Et H H SOMe H 1 CF Et HHH CN 2 CF Et H H SOMe H 2 CF Et HFH F 0 CF Et HH SO Me H 0 CF Et HFH F 1 3 2 3 CF Et HH SO Me H 1 CF Et HFH F 2 3 2 3 CF Et HH SO Me H 2 CF Et HClH Cl 0 3 2 3 CF Et HH OMe H 0 CF Et HClH Cl 1 CF Et HH OMe H 1 CF Et HClH Cl 2 CF Et HH OMe H 2 CF Et HBrH Br 0 CF Et H H OCF H 0 CF Et HBrH Br 1 3 3 3 CF Et H H OCF H 1 CF Et HBrH Br 2 3 3 3 CF Et H H OCF H 2 CF Et HIH I 0 3 3 3 CF Et HH NO H 0 CF Et HIH I 1 3 2 3 CF Et HH NO H 1 CF Et HIH I 2 3 2 3 CF Et HH NO H 2 CF Et HFH Cl 0 3 2 3 CF Et HH CN H 0 CF Et HFH Cl 1 CF Et HH CN H 1 CF Et HFH Cl 2 CF Et HH CN H 2 CF Et HFH Br 0 CF Et HHH F 0 CF Et HFH Br 1 CF Et HHH F 1 CF Et HFH Br 2 CF Et HHH F 2 CF Et HFH I 0 CF Et HHH Cl 0 CF Et HFH I 1 CF Et HHH Cl 1 CF Et HFH I 2 CF Et HHH Cl 2 CF Et HClH F 0 CF Et HHH Br 0 CF Et HClH F 1 CF Et HHH Br 1 CF Et HClH F 2 CF Et HHH Br 2 CF Et HClH Br 0 CF Et HHH I 0 CF Et HClH Br 1 CF Et HHH I 1 CF Et HClH Br 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Et HClH I 0 CF Et HF Cl H 1 CF Et HClH I 1 CF Et HF Cl H 2 CF Et HClH I 2 CF Et HF Br H 0 CF Et HBrH F 0 CF Et HF Br H 1 CF Et HBrH F 1 CF Et HF Br H 2 CF Et HBrH F 2 CF Et HFI H 0 CF Et HBrH Cl 0 CF Et HFI H 1 CF Et HBrH Cl 1 CF Et HFI H 2 CF Et HBrH Cl 2 CF Et HClF H 0 CF Et HBrH I 0 CF Et HClF H 1 CF Et HBrH I 1 CF Et HClF H 2 CF Et HBrH I 2 CF Et HCl Br H 0 CF Et HIH F 0 CF Et HCl Br H 1 CF Et HIH F 1 CF Et HCl Br H 2 CF Et HIH F 2 CF Et HClI H 0 CF Et HIH Cl 0 CF Et HClI H 1 CF Et HIH Cl 1 CF Et HClI H 2 CF Et HIH Cl 2 CF Et HBrF H 0 CF Et HIH Br 0 CF Et HBrF H 1 CF Et HIH Br 1 CF Et HBrF H 2 CF Et HIH Br 2 CF Et HBr Cl H 0 CF Et HFH CN 0 CF Et HBr Cl H 1 CF Et HFH CN 1 CF Et HBr Cl H 2 CF Et HFH CN 2 CF Et HBrI H 0 CF Et HClH CN 0 CF Et HBrI H 1 CF Et HClH CN 1 CF Et HBrI H 2 CF Et HClH CN 2 CF Et HIF H 0 CF Et HBrH CN 0 CF Et HIF H 1 CF Et HBrH CN 1 CF Et HIF H 2 CF Et HBrH CN 2 CF Et HI Cl H 0 CF Et HIH CN 0 CF Et HI Cl H 1 CF Et HIH CN 1 CF Et HI Cl H 2 CF Et HIH CN 2 CF Et HI Br H 0 CF Et HCF HF 0 CF Et HI Br H 1 3 3 3 CF Et HCF HF 1 CF Et HI Br H 2 3 3 3 CF Et HCF HF 2 CF Et HF CN H 0 3 3 3 CF Et HCF HCl 0 CF Et HF CN H 1 3 3 3 CF Et HCF HCl 1 CF Et HF CN H 2 3 3 3 CF Et HCF HCl 2 CF Et HCl CN H 0 3 3 3 CF Et HCF HBr 0 CF Et HCl CN H 1 3 3 3 CF Et HCF HBr 1 CF Et HCl CN H 2 3 3 3 CF Et HCF HBr 2 CF Et HBr CN H 0 3 3 3 CF Et HCF HI 0 CF Et HBr CN H 1 3 3 3 CF Et HCF HI 1 CF Et HBr CN H 2 3 3 3 CF Et HCF HI 2 CF Et HI CN H 0 3 3 3 CF Et HCF HCN 0 CF Et HI CN H 1 3 3 3 CF Et HCF HCN 1 CF Et HI CN H 2 3 3 3 CF Et HCF HCN 2 CF Et HCF FH 0 3 3 3 3 CF Et HFF H 0 CF Et HCF FH 1 3 3 3 CF Et HFF H 1 CF Et HCF FH 2 3 3 3 CF Et HFF H 2 CF Et HCF Cl H 0 3 3 3 CF Et HCl Cl H 0 CF Et HCF Cl H 1 3 3 3 CF Et HCl Cl H 1 CF Et HCF Cl H 2 3 3 3 CF Et HCl Cl H 2 CF Et HCF Br H 0 3 3 3 CF Et HBr Br H 0 CF Et HCF Br H 1 3 3 3 CF Et HBr Br H 1 CF Et HCF Br H 2 3 3 3 CF Et HBr Br H 2 CF Et HCF IH 0 3 3 3 CF Et HII H 0 CF Et HCF IH 1 3 3 3 CF Et HII H 1 CF Et HCF IH 2 3 3 3 CF Et HII H 2 CF Et HCF CN H 0 3 3 3 CF Et HF Cl H 0 CF Et HCF CN H 1 3 3 3 CF Et HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Pr HHH H 0 CF Pr HNO HH 1 3 3 2 CF HHH H 1 CF HNO HH 2 Pr Pr 3 3 2 CF Pr HHH H 2 CF Pr HCNH H 0 CF FHH H 0 CF HCNH H 1 Pr Pr CF Pr FHH H 1 CF Pr HCNH H 2 CF Pr FHH H 2 CF Pr HHF H 0 CF Pr Cl H H H 0 CF Pr HHF H 1 CF Pr Cl H H H 1 CF Pr HHF H 2 CF Cl H H H 2 CF HH Cl H 0 Pr Pr CF Pr Br H H H 0 CF Pr HH Cl H 1 CF Br H H H 1 CF HH Cl H 2 Pr Pr CF Pr Br H H H 2 CF Pr HH Br H 0 CF IHH H 0 CF HH Br H 1 Pr Pr CF Pr IHH H 1 CF Pr HH Br H 2 CF IHH H 2 CF HHI H 0 Pr Pr CF Pr Me H H H 0 CF Pr HHI H 1 CF Pr Me H H H 1 CF Pr HHI H 2 CF Me H H H 2 CF HH Me H 0 Pr Pr CF Pr CF HH H 0 CF Pr HH Me H 1 3 3 3 CF CF HH H 1 CF HH Me H 2 Pr Pr 3 3 3 CF Pr CF HH H 2 CF Pr HH CF H 0 3 3 3 3 CF HFH H 0 CF HH CF H 1 Pr Pr 3 3 3 CF Pr HFH H 1 CF Pr HH CF H 2 3 3 3 CF Pr HFH H 2 CF Pr HH CF CF H 0 3 3 2 3 CF Pr HClH H 0 CF Pr HH CF CF H 1 3 3 2 3 CF Pr HClH H 1 CF Pr HH CF CF H 2 3 3 2 3 CF HClH H 2 CF H H CF(CF ) H 0 Pr Pr 3 3 3 2 CF Pr HBrH H 0 CF Pr H H CF(CF ) H 1 3 3 3 2 CF HBrH H 1 CF H H CF(CF ) H 2 Pr Pr 3 3 3 2 CF Pr HBrH H 2 CF Pr HH SMe H 0 CF HIH H 0 CF HH SMe H 1 Pr Pr CF Pr HIH H 1 CF Pr HH SMe H 2 CF Pr HIH H 2 CF Pr H H SOMe H 0 CF Pr HMeH H 0 CF Pr H H SOMe H 1 CF Pr HMeH H 1 CF Pr H H SOMe H 2 CF HMeH H 2 CF HH SO Me H 0 Pr Pr 3 3 2 CF Pr HCF HH 0 CF Pr HH SO Me H 1 3 3 3 2 CF HCF HH 1 CF HH SO Me H 2 Pr Pr 3 3 3 2 CF Pr HCF HH 2 CF Pr HH OMe H 0 3 3 3 CF HCF CF HH 0 CF HH OMe H 1 Pr Pr 3 2 3 3 CF Pr HCF CF HH 1 CF Pr HH OMe H 2 3 2 3 3 CF HCF CF HH 2 CF H H OCF H 0 Pr Pr 3 2 3 3 3 CF Pr H CF(CF ) HH 0 CF Pr H H OCF H 1 3 3 2 3 3 CF Pr H CF(CF ) HH 1 CF Pr H H OCF H 2 3 3 2 3 3 CF H CF(CF ) HH 2 CF HH NO H 0 Pr Pr 3 3 2 3 2 CF Pr H SMe H H 0 CF Pr HH NO H 1 3 3 2 CF H SMe H H 1 CF HH NO H 2 Pr Pr 3 3 2 CF Pr H SMe H H 2 CF Pr HH CN H 0 CF HSOMeH H 0 CF HH CN H 1 Pr Pr CF Pr HSOMeH H 1 CF Pr HH CN H 2 CF Pr HSOMeH H 2 CF Pr HHH F 0 CF Pr HSO Me H H 0 CF Pr HHH F 1 3 2 3 CF Pr HSO Me H H 1 CF Pr HHH F 2 3 2 3 CF HSO Me H H 2 CF HHH Cl 0 Pr Pr 3 2 3 CF Pr H OMe H H 0 CF Pr HHH Cl 1 CF H OMe H H 1 CF HHH Cl 2 Pr Pr CF Pr H OMe H H 2 CF Pr HHH Br 0 CF HOCF HH 0 CF HHH Br 1 Pr Pr 3 3 3 CF Pr HOCF HH 1 CF Pr HHH Br 2 3 3 3 CF HOCF HH 2 CF HHH I 0 Pr Pr 3 3 3 CF Pr HNO HH 0 CF Pr HHH I 1 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Pr HHH I 2 CF Pr HClH I 0 CF HHH Me 0 CF HClH I 1 Pr Pr CF Pr HHH Me 1 CF Pr HClH I 2 CF HHH Me 2 CF HBrH F 0 Pr Pr CF Pr HHH CF 0 CF Pr HBrH F 1 3 3 3 CF Pr HHH CF 1 CF Pr HBrH F 2 3 3 3 CF Pr HHH CF 2 CF Pr HBrH Cl 0 3 3 3 CF Pr HHH CF CF 0 CF Pr HBrH Cl 1 3 2 3 3 CF HHH CF CF 1 CF HBrH Cl 2 Pr Pr 3 2 3 3 CF Pr HHH CF CF 2 CF Pr HBrH I 0 3 2 3 3 CF H H H CF(CF ) 0 CF HBrH I 1 Pr Pr 3 3 2 3 CF Pr H H H CF(CF ) 1 CF Pr HBrH I 2 3 3 2 3 CF H H H CF(CF ) 2 CF HIH F 0 Pr Pr 3 3 2 3 CF Pr HHH SMe 0 CF Pr HIH F 1 CF HHH SMe 1 CF HIH F 2 Pr Pr CF Pr HHH SMe 2 CF Pr HIH Cl 0 CF Pr HHH SOMe 0 CF Pr HIH Cl 1 CF HHH SOMe 1 CF HIH Cl 2 Pr Pr CF Pr HHH SOMe 2 CF Pr HIH Br 0 CF HHH SO Me 0 CF HIH Br 1 Pr Pr 3 2 3 CF Pr HHH SO Me 1 CF Pr HIH Br 2 3 2 3 CF HHH SO Me 2 CF HFH CN 0 Pr Pr 3 2 3 CF Pr HHH OMe 0 CF Pr HFH CN 1 CF Pr HHH OMe 1 CF Pr HFH CN 2 CF Pr HHH OMe 2 CF Pr HClH CN 0 CF Pr HHH OCF 0 CF Pr HClH CN 1 3 3 3 CF HHH OCF 1 CF HClH CN 2 Pr Pr 3 3 3 CF Pr HHH OCF 2 CF Pr HBrH CN 0 3 3 3 CF HHH NO 0 CF HBrH CN 1 Pr Pr 3 2 3 CF Pr HHH NO 1 CF Pr HBrH CN 2 3 2 3 CF HHH NO 2 CF HIH CN 0 Pr Pr 3 2 3 CF Pr HHH CN 0 CF Pr HIH CN 1 CF Pr HHH CN 1 CF Pr HIH CN 2 CF Pr HHH CN 2 CF Pr HCF HF 0 3 3 3 CF Pr HFH F 0 CF Pr HCF HF 1 3 3 3 CF HFH F 1 CF HCF HF 2 Pr Pr 3 3 3 CF Pr HFH F 2 CF Pr HCF HCl 0 3 3 3 CF HClH Cl 0 CF HCF HCl 1 Pr Pr 3 3 3 CF Pr HClH Cl 1 CF Pr HCF HCl 2 3 3 3 CF HClH Cl 2 CF HCF HBr 0 Pr Pr 3 3 3 CF Pr HBrH Br 0 CF Pr HCF HBr 1 3 3 3 CF HBrH Br 1 CF HCF HBr 2 Pr Pr 3 3 3 CF Pr HBrH Br 2 CF Pr HCF HI 0 3 3 3 CF Pr HIH I 0 CF Pr HCF HI 1 3 3 3 CF HIH I 1 CF HCF HI 2 Pr Pr 3 3 3 CF Pr HIH I 2 CF Pr HCF HCN 0 3 3 3 CF HFH Cl 0 CF HCF HCN 1 Pr Pr 3 3 3 CF Pr HFH Cl 1 CF Pr HCF HCN 2 3 3 3 CF HFH Cl 2 CF HFF H 0 Pr Pr CF Pr HFH Br 0 CF Pr HFF H 1 CF Pr HFH Br 1 CF Pr HFF H 2 CF Pr HFH Br 2 CF Pr HCl Cl H 0 CF Pr HFH I 0 CF Pr HCl Cl H 1 CF HFH I 1 CF HCl Cl H 2 Pr Pr CF Pr HFH I 2 CF Pr HBr Br H 0 CF HClH F 0 CF HBr Br H 1 Pr Pr CF Pr HClH F 1 CF Pr HBr Br H 2 CF HClH F 2 CF HII H 0 Pr Pr CF Pr HClH Br 0 CF Pr HII H 1 CF HClH Br 1 CF HII H 2 Pr Pr CF Pr HClH Br 2 CF Pr HF Cl H 0 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Pr HF Cl H 1 CF Pr HHH H 0 CF HF Cl H 2 CF HHH H 1 Pr Pr CF Pr HF Br H 0 CF Pr HHH H 2 CF HF Br H 1 CF FHH H 0 Pr Pr CF Pr HF Br H 2 CF Pr FHH H 1 CF HFI H 0 CF FHH H 2 Pr Pr CF Pr HFI H 1 CF Pr Cl H H H 0 CF Pr HFI H 2 CF Pr Cl H H H 1 CF Pr HClF H 0 CF Pr Cl H H H 2 CF Pr HClF H 1 CF Pr Br H H H 0 CF HClF H 2 CF Br H H H 1 Pr Pr CF Pr HCl Br H 0 CF Pr Br H H H 2 CF HCl Br H 1 CF IHH H 0 Pr Pr CF Pr HCl Br H 2 CF Pr IHH H 1 CF HClI H 0 CF IHH H 2 Pr Pr CF Pr HClI H 1 CF Pr Me H H H 0 CF Pr HClI H 2 CF Pr Me H H H 1 CF Pr HBrF H 0 CF Pr Me H H H 2 CF Pr HBrF H 1 CF Pr CF HH H 0 3 3 3 CF HBrF H 2 CF CF HH H 1 Pr Pr 3 3 3 CF Pr HBr Cl H 0 CF Pr CF HH H 2 3 3 3 CF HBr Cl H 1 CF HFH H 0 Pr Pr CF Pr HBr Cl H 2 CF Pr HFH H 1 CF HBrI H 0 CF HFH H 2 Pr Pr CF Pr HBrI H 1 CF Pr HClH H 0 CF HBrI H 2 CF HClH H 1 Pr Pr CF Pr HIF H 0 CF Pr HClH H 2 CF Pr HIF H 1 CF Pr HBrH H 0 CF Pr HIF H 2 CF Pr HBrH H 1 CF Pr HI Cl H 0 CF Pr HBrH H 2 CF HI Cl H 1 CF HIH H 0 Pr Pr CF Pr HI Cl H 2 CF Pr HIH H 1 CF HI Br H 0 CF HIH H 2 Pr Pr CF Pr HI Br H 1 CF Pr HMeH H 0 CF HI Br H 2 CF HMeH H 1 Pr Pr CF Pr HF CN H 0 CF Pr HMeH H 2 CF Pr HF CN H 1 CF Pr HCF HH 0 3 3 3 CF Pr HF CN H 2 CF Pr HCF HH 1 3 3 3 CF Pr HCl CN H 0 CF Pr HCF HH 2 3 3 3 CF HCl CN H 1 CF HCF CF HH 0 Pr Pr 3 3 2 3 CF Pr HCl CN H 2 CF Pr HCF CF HH 1 3 3 2 3 CF HBr CN H 0 CF HCF CF HH 2 Pr Pr 3 3 2 3 CF Pr HBr CN H 1 CF Pr H CF(CF ) HH 0 3 3 3 2 CF HBr CN H 2 CF H CF(CF ) HH 1 Pr Pr 3 3 3 2 CF Pr HI CN H 0 CF Pr H CF(CF ) HH 2 3 3 3 2 CF HI CN H 1 CF H SMe H H 0 Pr Pr CF Pr HI CN H 2 CF Pr H SMe H H 1 CF HCF FH 0 CF H SMe H H 2 Pr Pr 3 3 3 CF Pr HCF FH 1 CF Pr HSOMeH H 0 3 3 3 CF Pr HCF FH 2 CF Pr HSOMeH H 1 3 3 3 CF HCF Cl H 0 CF HSOMeH H 2 Pr Pr 3 3 3 CF Pr HCF Cl H 1 CF Pr HSO Me H H 0 3 3 3 2 CF HCF Cl H 2 CF HSO Me H H 1 Pr Pr 3 3 3 2 CF Pr HCF Br H 0 CF Pr HSO Me H H 2 3 3 3 2 CF HCF Br H 1 CF H OMe H H 0 Pr Pr 3 3 3 CF Pr HCF Br H 2 CF Pr H OMe H H 1 3 3 3 CF Pr HCF IH 0 CF Pr H OMe H H 2 3 3 3 CF Pr HCF IH 1 CF Pr HOCF HH 0 3 3 3 3 CF Pr HCF IH 2 CF Pr HOCF HH 1 3 3 3 3 CF Pr HCF CN H 0 CF Pr HOCF HH 2 3 3 3 3 CF Pr HCF CN H 1 CF Pr HNO HH 0 3 3 3 2 CF HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Pr HNO HH 1 CF Pr HHH I 2 3 2 3 CF HNO HH 2 CF HHH Me 0 Pr Pr 3 2 3 CF Pr HCNH H 0 CF Pr HHH Me 1 CF HCNH H 1 CF HHH Me 2 Pr Pr CF Pr HCNH H 2 CF Pr HHH CF 0 3 3 3 CF Pr HHF H 0 CF Pr HHH CF 1 3 3 3 CF Pr HHF H 1 CF Pr HHH CF 2 3 3 3 CF Pr HHF H 2 CF Pr HHH CF CF 0 3 3 2 3 CF HH Cl H 0 CF HHH CF CF 1 Pr Pr 3 3 2 3 CF Pr HH Cl H 1 CF Pr HHH CF CF 2 3 3 2 3 CF HH Cl H 2 CF H H H CF(CF ) 0 Pr Pr 3 3 3 2 CF Pr HH Br H 0 CF Pr H H H CF(CF ) 1 3 3 3 2 CF HH Br H 1 CF H H H CF(CF ) 2 Pr Pr 3 3 3 2 CF Pr HH Br H 2 CF Pr HHH SMe 0 CF HHI H 0 CF HHH SMe 1 Pr Pr CF Pr HHI H 1 CF Pr HHH SMe 2 CF Pr HHI H 2 CF Pr HHH SOMe 0 CF HH Me H 0 CF HHH SOMe 1 Pr Pr CF Pr HH Me H 1 CF Pr HHH SOMe 2 CF HH Me H 2 CF HHH SO Me 0 Pr Pr 3 3 2 CF Pr HH CF H 0 CF Pr HHH SO Me 1 3 3 3 2 CF HH CF H 1 CF HHH SO Me 2 Pr Pr 3 3 3 2 CF Pr HH CF H 2 CF Pr HHH OMe 0 3 3 3 CF Pr HH CF CF H 0 CF Pr HHH OMe 1 3 2 3 3 CF Pr HH CF CF H 1 CF Pr HHH OMe 2 3 2 3 3 CF Pr HH CF CF H 2 CF Pr HHH OCF 0 3 2 3 3 3 CF H H CF(CF ) H 0 CF HHH OCF 1 Pr Pr 3 3 2 3 3 CF Pr H H CF(CF ) H 1 CF Pr HHH OCF 2 3 3 2 3 3 CF H H CF(CF ) H 2 CF HHH NO 0 Pr Pr 3 3 2 3 2 CF Pr HH SMe H 0 CF Pr HHH NO 1 3 3 2 CF HH SMe H 1 CF HHH NO 2 Pr Pr 3 3 2 CF Pr HH SMe H 2 CF Pr HHH CN 0 CF Pr H H SOMe H 0 CF Pr HHH CN 1 CF Pr H H SOMe H 1 CF Pr HHH CN 2 CF Pr H H SOMe H 2 CF Pr HFH F 0 CF HH SO Me H 0 CF HFH F 1 Pr Pr 3 2 3 CF Pr HH SO Me H 1 CF Pr HFH F 2 3 2 3 CF HH SO Me H 2 CF HClH Cl 0 Pr Pr 3 2 3 CF Pr HH OMe H 0 CF Pr HClH Cl 1 CF HH OMe H 1 CF HClH Cl 2 Pr Pr CF Pr HH OMe H 2 CF Pr HBrH Br 0 CF H H OCF H 0 CF HBrH Br 1 Pr Pr 3 3 3 CF Pr H H OCF H 1 CF Pr HBrH Br 2 3 3 3 CF Pr H H OCF H 2 CF Pr HIH I 0 3 3 3 CF HH NO H 0 CF HIH I 1 Pr Pr 3 2 3 CF Pr HH NO H 1 CF Pr HIH I 2 3 2 3 CF HH NO H 2 CF HFH Cl 0 Pr Pr 3 2 3 CF Pr HH CN H 0 CF Pr HFH Cl 1 CF HH CN H 1 CF HFH Cl 2 Pr Pr CF Pr HH CN H 2 CF Pr HFH Br 0 CF Pr HHH F 0 CF Pr HFH Br 1 CF Pr HHH F 1 CF Pr HFH Br 2 CF Pr HHH F 2 CF Pr HFH I 0 CF HHH Cl 0 CF HFH I 1 Pr Pr CF Pr HHH Cl 1 CF Pr HFH I 2 CF HHH Cl 2 CF HClH F 0 Pr Pr CF Pr HHH Br 0 CF Pr HClH F 1 CF HHH Br 1 CF HClH F 2 Pr Pr CF Pr HHH Br 2 CF Pr HClH Br 0 CF HHH I 0 CF HClH Br 1 Pr Pr CF Pr HHH I 1 CF Pr HClH Br 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF Pr HClH I 0 CF Pr HF Cl H 1 CF HClH I 1 CF HF Cl H 2 Pr Pr CF Pr HClH I 2 CF Pr HF Br H 0 CF HBrH F 0 CF HF Br H 1 Pr Pr CF Pr HBrH F 1 CF Pr HF Br H 2 CF HBrH F 2 CF HFI H 0 Pr Pr CF Pr HBrH Cl 0 CF Pr HFI H 1 CF Pr HBrH Cl 1 CF Pr HFI H 2 CF Pr HBrH Cl 2 CF Pr HClF H 0 CF Pr HBrH I 0 CF Pr HClF H 1 CF HBrH I 1 CF HClF H 2 Pr Pr CF Pr HBrH I 2 CF Pr HCl Br H 0 CF HIH F 0 CF HCl Br H 1 Pr Pr CF Pr HIH F 1 CF Pr HCl Br H 2 CF HIH F 2 CF HClI H 0 Pr Pr CF Pr HIH Cl 0 CF Pr HClI H 1 CF Pr HIH Cl 1 CF Pr HClI H 2 CF Pr HIH Cl 2 CF Pr HBrF H 0 CF Pr HIH Br 0 CF Pr HBrF H 1 CF HIH Br 1 CF HBrF H 2 Pr Pr CF Pr HIH Br 2 CF Pr HBr Cl H 0 CF HFH CN 0 CF HBr Cl H 1 Pr Pr CF Pr HFH CN 1 CF Pr HBr Cl H 2 CF HFH CN 2 CF HBrI H 0 Pr Pr CF Pr HClH CN 0 CF Pr HBrI H 1 CF HClH CN 1 CF HBrI H 2 Pr Pr CF Pr HClH CN 2 CF Pr HIF H 0 CF Pr HBrH CN 0 CF Pr HIF H 1 CF Pr HBrH CN 1 CF Pr HIF H 2 CF Pr HBrH CN 2 CF Pr HI Cl H 0 CF HIH CN 0 CF HI Cl H 1 Pr Pr CF Pr HIH CN 1 CF Pr HI Cl H 2 CF HIH CN 2 CF HI Br H 0 Pr Pr CF Pr HCF HF 0 CF Pr HI Br H 1 3 3 3 CF HCF HF 1 CF HI Br H 2 Pr Pr 3 3 3 CF Pr HCF HF 2 CF Pr HF CN H 0 3 3 3 CF Pr HCF HCl 0 CF Pr HF CN H 1 3 3 3 CF Pr HCF HCl 1 CF Pr HF CN H 2 3 3 3 CF Pr HCF HCl 2 CF Pr HCl CN H 0 3 3 3 CF HCF HBr 0 CF HCl CN H 1 Pr Pr 3 3 3 CF Pr HCF HBr 1 CF Pr HCl CN H 2 3 3 3 CF HCF HBr 2 CF HBr CN H 0 Pr Pr 3 3 3 CF Pr HCF HI 0 CF Pr HBr CN H 1 3 3 3 CF HCF HI 1 CF HBr CN H 2 Pr Pr 3 3 3 CF Pr HCF HI 2 CF Pr HI CN H 0 3 3 3 CF HCF HCN 0 CF HI CN H 1 Pr Pr 3 3 3 CF Pr HCF HCN 1 CF Pr HI CN H 2 3 3 3 CF HCF HCN 2 CF HCF FH 0 Pr Pr 3 3 3 3 CF Pr HFF H 0 CF Pr HCF FH 1 3 3 3 CF Pr HFF H 1 CF Pr HCF FH 2 3 3 3 CF HFF H 2 CF HCF Cl H 0 Pr Pr 3 3 3 CF Pr HCl Cl H 0 CF Pr HCF Cl H 1 3 3 3 CF HCl Cl H 1 CF HCF Cl H 2 Pr Pr 3 3 3 CF Pr HCl Cl H 2 CF Pr HCF Br H 0 3 3 3 CF HBr Br H 0 CF HCF Br H 1 Pr Pr 3 3 3 CF Pr HBr Br H 1 CF Pr HCF Br H 2 3 3 3 CF Pr HBr Br H 2 CF Pr HCF IH 0 3 3 3 CF Pr HII H 0 CF Pr HCF IH 1 3 3 3 CF Pr HII H 1 CF Pr HCF IH 2 3 3 3 CF Pr HII H 2 CF Pr HCF CN H 0 3 3 3 CF Pr HF Cl H 0 CF Pr HCF CN H 1 3 3 3 CF HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CH CF HHH H 0 CF CH CF HNO HH 1 3 2 3 3 2 3 2 CF CH CF HHH H 1 CF CH CF HNO HH 2 3 2 3 3 2 3 2 CF CH CF HHH H 2 CF CH CF HCNH H 0 3 2 3 3 2 3 CF CH CF FHH H 0 CF CH CF HCNH H 1 3 2 3 3 2 3 CF CH CF FHH H 1 CF CH CF HCNH H 2 3 2 3 3 2 3 CF CH CF FHH H 2 CF CH CF HHF H 0 3 2 3 3 2 3 CF CH CF Cl H H H 0 CF CH CF HHF H 1 3 2 3 3 2 3 CF CH CF Cl H H H 1 CF CH CF HHF H 2 3 2 3 3 2 3 CF CH CF Cl H H H 2 CF CH CF HH Cl H 0 3 2 3 3 2 3 CF CH CF Br H H H 0 CF CH CF HH Cl H 1 3 2 3 3 2 3 CF CH CF Br H H H 1 CF CH CF HH Cl H 2 3 2 3 3 2 3 CF CH CF Br H H H 2 CF CH CF HH Br H 0 3 2 3 3 2 3 CF CH CF IHH H 0 CF CH CF HH Br H 1 3 2 3 3 2 3 CF CH CF IHH H 1 CF CH CF HH Br H 2 3 2 3 3 2 3 CF CH CF IHH H 2 CF CH CF HHI H 0 3 2 3 3 2 3 CF CH CF Me H H H 0 CF CH CF HHI H 1 3 2 3 3 2 3 CF CH CF Me H H H 1 CF CH CF HHI H 2 3 2 3 3 2 3 CF CH CF Me H H H 2 CF CH CF HH Me H 0 3 2 3 3 2 3 CF CH CF CF HH H 0 CF CH CF HH Me H 1 3 2 3 3 3 2 3 CF CH CF CF HH H 1 CF CH CF HH Me H 2 3 2 3 3 3 2 3 CF CH CF CF HH H 2 CF CH CF HH CF H 0 3 2 3 3 3 2 3 3 CF CH CF HFH H 0 CF CH CF HH CF H 1 3 2 3 3 2 3 3 CF CH CF HFH H 1 CF CH CF HH CF H 2 3 2 3 3 2 3 3 CF CH CF HFH H 2 CF CH CF HH CF CF H 0 3 2 3 3 2 3 2 3 CF CH CF HClH H 0 CF CH CF HH CF CF H 1 3 2 3 3 2 3 2 3 CF CH CF HClH H 1 CF CH CF HH CF CF H 2 3 2 3 3 2 3 2 3 CF CH CF HClH H 2 CF CH CF H H CF(CF ) H 0 3 2 3 3 2 3 3 2 CF CH CF HBrH H 0 CF CH CF H H CF(CF ) H 1 3 2 3 3 2 3 3 2 CF CH CF HBrH H 1 CF CH CF H H CF(CF ) H 2 3 2 3 3 2 3 3 2 CF CH CF HBrH H 2 CF CH CF HH SMe H 0 3 2 3 3 2 3 CF CH CF HIH H 0 CF CH CF HH SMe H 1 3 2 3 3 2 3 CF CH CF HIH H 1 CF CH CF HH SMe H 2 3 2 3 3 2 3 CF CH CF HIH H 2 CF CH CF H H SOMe H 0 3 2 3 3 2 3 CF CH CF HMeH H 0 CF CH CF H H SOMe H 1 3 2 3 3 2 3 CF CH CF HMeH H 1 CF CH CF H H SOMe H 2 3 2 3 3 2 3 CF CH CF HMeH H 2 CF CH CF HH SO Me H 0 3 2 3 3 2 3 2 CF CH CF HCF HH 0 CF CH CF HH SO Me H 1 3 2 3 3 3 2 3 2 CF CH CF HCF HH 1 CF CH CF HH SO Me H 2 3 2 3 3 3 2 3 2 CF CH CF HCF HH 2 CF CH CF HH OMe H 0 3 2 3 3 3 2 3 CF CH CF HCF CF HH 0 CF CH CF HH OMe H 1 3 2 3 2 3 3 2 3 CF CH CF HCF CF HH 1 CF CH CF HH OMe H 2 3 2 3 2 3 3 2 3 CF CH CF HCF CF HH 2 CF CH CF H H OCF H 0 3 2 3 2 3 3 2 3 3 CF CH CF H CF(CF ) HH 0 CF CH CF H H OCF H 1 3 2 3 3 2 3 2 3 3 CF CH CF H CF(CF ) HH 1 CF CH CF H H OCF H 2 3 2 3 3 2 3 2 3 3 CF CH CF H CF(CF ) HH 2 CF CH CF HH NO H 0 3 2 3 3 2 3 2 3 2 CF CH CF H SMe H H 0 CF CH CF HH NO H 1 3 2 3 3 2 3 2 CF CH CF H SMe H H 1 CF CH CF HH NO H 2 3 2 3 3 2 3 2 CF CH CF H SMe H H 2 CF CH CF HH CN H 0 3 2 3 3 2 3 CF CH CF HSOMeH H 0 CF CH CF HH CN H 1 3 2 3 3 2 3 CF CH CF HSOMeH H 1 CF CH CF HH CN H 2 3 2 3 3 2 3 CF CH CF HSOMeH H 2 CF CH CF HHH F 0 3 2 3 3 2 3 CF CH CF HSO Me H H 0 CF CH CF HHH F 1 3 2 3 2 3 2 3 CF CH CF HSO Me H H 1 CF CH CF HHH F 2 3 2 3 2 3 2 3 CF CH CF HSO Me H H 2 CF CH CF HHH Cl 0 3 2 3 2 3 2 3 CF CH CF H OMe H H 0 CF CH CF HHH Cl 1 3 2 3 3 2 3 CF CH CF H OMe H H 1 CF CH CF HHH Cl 2 3 2 3 3 2 3 CF CH CF H OMe H H 2 CF CH CF HHH Br 0 3 2 3 3 2 3 CF CH CF HOCF HH 0 CF CH CF HHH Br 1 3 2 3 3 3 2 3 CF CH CF HOCF HH 1 CF CH CF HHH Br 2 3 2 3 3 3 2 3 CF CH CF HOCF HH 2 CF CH CF HHH I 0 3 2 3 3 3 2 3 CF CH CF HNO HH 0 CF CH CF HHH I 1 3 2 3 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CH CF HHH I 2 CF CH CF HClH I 0 3 2 3 3 2 3 CF CH CF HHH Me 0 CF CH CF HClH I 1 3 2 3 3 2 3 CF CH CF HHH Me 1 CF CH CF HClH I 2 3 2 3 3 2 3 CF CH CF HHH Me 2 CF CH CF HBrH F 0 3 2 3 3 2 3 CF CH CF HHH CF 0 CF CH CF HBrH F 1 3 2 3 3 3 2 3 CF CH CF HHH CF 1 CF CH CF HBrH F 2 3 2 3 3 3 2 3 CF CH CF HHH CF 2 CF CH CF HBrH Cl 0 3 2 3 3 3 2 3 CF CH CF HHH CF CF 0 CF CH CF HBrH Cl 1 3 2 3 2 3 3 2 3 CF CH CF HHH CF CF 1 CF CH CF HBrH Cl 2 3 2 3 2 3 3 2 3 CF CH CF HHH CF CF 2 CF CH CF HBrH I 0 3 2 3 2 3 3 2 3 CF CH CF H H H CF(CF ) 0 CF CH CF HBrH I 1 3 2 3 3 2 3 2 3 CF CH CF H H H CF(CF ) 1 CF CH CF HBrH I 2 3 2 3 3 2 3 2 3 CF CH CF H H H CF(CF ) 2 CF CH CF HIH F 0 3 2 3 3 2 3 2 3 CF CH CF HHH SMe 0 CF CH CF HIH F 1 3 2 3 3 2 3 CF CH CF HHH SMe 1 CF CH CF HIH F 2 3 2 3 3 2 3 CF CH CF HHH SMe 2 CF CH CF HIH Cl 0 3 2 3 3 2 3 CF CH CF HHH SOMe 0 CF CH CF HIH Cl 1 3 2 3 3 2 3 CF CH CF HHH SOMe 1 CF CH CF HIH Cl 2 3 2 3 3 2 3 CF CH CF HHH SOMe 2 CF CH CF HIH Br 0 3 2 3 3 2 3 CF CH CF HHH SO Me 0 CF CH CF HIH Br 1 3 2 3 2 3 2 3 CF CH CF HHH SO Me 1 CF CH CF HIH Br 2 3 2 3 2 3 2 3 CF CH CF HHH SO Me 2 CF CH CF HFH CN 0 3 2 3 2 3 2 3 CF CH CF HHH OMe 0 CF CH CF HFH CN 1 3 2 3 3 2 3 CF CH CF HHH OMe 1 CF CH CF HFH CN 2 3 2 3 3 2 3 CF CH CF HHH OMe 2 CF CH CF HClH CN 0 3 2 3 3 2 3 CF CH CF HHH OCF 0 CF CH CF HClH CN 1 3 2 3 3 3 2 3 CF CH CF HHH OCF 1 CF CH CF HClH CN 2 3 2 3 3 3 2 3 CF CH CF HHH OCF 2 CF CH CF HBrH CN 0 3 2 3 3 3 2 3 CF CH CF HHH NO 0 CF CH CF HBrH CN 1 3 2 3 2 3 2 3 CF CH CF HHH NO 1 CF CH CF HBrH CN 2 3 2 3 2 3 2 3 CF CH CF HHH NO 2 CF CH CF HIH CN 0 3 2 3 2 3 2 3 CF CH CF HHH CN 0 CF CH CF HIH CN 1 3 2 3 3 2 3 CF CH CF HHH CN 1 CF CH CF HIH CN 2 3 2 3 3 2 3 CF CH CF HHH CN 2 CF CH CF HCF HF 0 3 2 3 3 2 3 3 CF CH CF HFH F 0 CF CH CF HCF HF 1 3 2 3 3 2 3 3 CF CH CF HFH F 1 CF CH CF HCF HF 2 3 2 3 3 2 3 3 CF CH CF HFH F 2 CF CH CF HCF HCl 0 3 2 3 3 2 3 3 CF CH CF HClH Cl 0 CF CH CF HCF HCl 1 3 2 3 3 2 3 3 CF CH CF HClH Cl 1 CF CH CF HCF HCl 2 3 2 3 3 2 3 3 CF CH CF HClH Cl 2 CF CH CF HCF HBr 0 3 2 3 3 2 3 3 CF CH CF HBrH Br 0 CF CH CF HCF HBr 1 3 2 3 3 2 3 3 CF CH CF HBrH Br 1 CF CH CF HCF HBr 2 3 2 3 3 2 3 3 CF CH CF HBrH Br 2 CF CH CF HCF HI 0 3 2 3 3 2 3 3 CF CH CF HIH I 0 CF CH CF HCF HI 1 3 2 3 3 2 3 3 CF CH CF HIH I 1 CF CH CF HCF HI 2 3 2 3 3 2 3 3 CF CH CF HIH I 2 CF CH CF HCF HCN 0 3 2 3 3 2 3 3 CF CH CF HFH Cl 0 CF CH CF HCF HCN 1 3 2 3 3 2 3 3 CF CH CF HFH Cl 1 CF CH CF HCF HCN 2 3 2 3 3 2 3 3 CF CH CF HFH Cl 2 CF CH CF HFF H 0 3 2 3 3 2 3 CF CH CF HFH Br 0 CF CH CF HFF H 1 3 2 3 3 2 3 CF CH CF HFH Br 1 CF CH CF HFF H 2 3 2 3 3 2 3 CF CH CF HFH Br 2 CF CH CF HCl Cl H 0 3 2 3 3 2 3 CF CH CF HFH I 0 CF CH CF HCl Cl H 1 3 2 3 3 2 3 CF CH CF HFH I 1 CF CH CF HCl Cl H 2 3 2 3 3 2 3 CF CH CF HFH I 2 CF CH CF HBr Br H 0 3 2 3 3 2 3 CF CH CF HClH F 0 CF CH CF HBr Br H 1 3 2 3 3 2 3 CF CH CF HClH F 1 CF CH CF HBr Br H 2 3 2 3 3 2 3 CF CH CF HClH F 2 CF CH CF HII H 0 3 2 3 3 2 3 CF CH CF HClH Br 0 CF CH CF HII H 1 3 2 3 3 2 3 CF CH CF HClH Br 1 CF CH CF HII H 2 3 2 3 3 2 3 CF CH CF HClH Br 2 CF CH CF HF Cl H 0 3 2 3 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CH CF HF Cl H 1 CF CF Me HHH H 0 3 2 3 2 3 CF CH CF HF Cl H 2 CF CF Me HHH H 1 3 2 3 2 3 CF CH CF HF Br H 0 CF CF Me HHH H 2 3 2 3 2 3 CF CH CF HF Br H 1 CF CF Me FHH H 0 3 2 3 2 3 CF CH CF HF Br H 2 CF CF Me FHH H 1 3 2 3 2 3 CF CH CF HFI H 0 CF CF Me FHH H 2 3 2 3 2 3 CF CH CF HFI H 1 CF CF Me Cl H H H 0 3 2 3 2 3 CF CH CF HFI H 2 CF CF Me Cl H H H 1 3 2 3 2 3 CF CH CF HClF H 0 CF CF Me Cl H H H 2 3 2 3 2 3 CF CH CF HClF H 1 CF CF Me Br H H H 0 3 2 3 2 3 CF CH CF HClF H 2 CF CF Me Br H H H 1 3 2 3 2 3 CF CH CF HCl Br H 0 CF CF Me Br H H H 2 3 2 3 2 3 CF CH CF HCl Br H 1 CF CF Me IHH H 0 3 2 3 2 3 CF CH CF HCl Br H 2 CF CF Me IHH H 1 3 2 3 2 3 CF CH CF HClI H 0 CF CF Me IHH H 2 3 2 3 2 3 CF CH CF HClI H 1 CF CF Me Me H H H 0 3 2 3 2 3 CF CH CF HClI H 2 CF CF Me Me H H H 1 3 2 3 2 3 CF CH CF HBrF H 0 CF CF Me Me H H H 2 3 2 3 2 3 CF CH CF HBrF H 1 CF CF Me CF HH H 0 3 2 3 2 3 3 CF CH CF HBrF H 2 CF CF Me CF HH H 1 3 2 3 2 3 3 CF CH CF HBr Cl H 0 CF CF Me CF HH H 2 3 2 3 2 3 3 CF CH CF HBr Cl H 1 CF CF Me HFH H 0 3 2 3 2 3 CF CH CF HBr Cl H 2 CF CF Me HFH H 1 3 2 3 2 3 CF CH CF HBrI H 0 CF CF Me HFH H 2 3 2 3 2 3 CF CH CF HBrI H 1 CF CF Me HClH H 0 3 2 3 2 3 CF CH CF HBrI H 2 CF CF Me HClH H 1 3 2 3 2 3 CF CH CF HIF H 0 CF CF Me HClH H 2 3 2 3 2 3 CF CH CF HIF H 1 CF CF Me HBrH H 0 3 2 3 2 3 CF CH CF HIF H 2 CF CF Me HBrH H 1 3 2 3 2 3 CF CH CF HI Cl H 0 CF CF Me HBrH H 2 3 2 3 2 3 CF CH CF HI Cl H 1 CF CF Me HIH H 0 3 2 3 2 3 CF CH CF HI Cl H 2 CF CF Me HIH H 1 3 2 3 2 3 CF CH CF HI Br H 0 CF CF Me HIH H 2 3 2 3 2 3 CF CH CF HI Br H 1 CF CF Me HMeH H 0 3 2 3 2 3 CF CH CF HI Br H 2 CF CF Me HMeH H 1 3 2 3 2 3 CF CH CF HF CN H 0 CF CF Me HMeH H 2 3 2 3 2 3 CF CH CF HF CN H 1 CF CF Me HCF HH 0 3 2 3 2 3 3 CF CH CF HF CN H 2 CF CF Me HCF HH 1 3 2 3 2 3 3 CF CH CF HCl CN H 0 CF CF Me HCF HH 2 3 2 3 2 3 3 CF CH CF HCl CN H 1 CF CF Me HCF CF HH 0 3 2 3 2 3 2 3 CF CH CF HCl CN H 2 CF CF Me HCF CF HH 1 3 2 3 2 3 2 3 CF CH CF HBr CN H 0 CF CF Me HCF CF HH 2 3 2 3 2 3 2 3 CF CH CF HBr CN H 1 CF CF Me H CF(CF ) HH 0 3 2 3 2 3 3 2 CF CH CF HBr CN H 2 CF CF Me H CF(CF ) HH 1 3 2 3 2 3 3 2 CF CH CF HI CN H 0 CF CF Me H CF(CF ) HH 2 3 2 3 2 3 3 2 CF CH CF HI CN H 1 CF CF Me H SMe H H 0 3 2 3 2 3 CF CH CF HI CN H 2 CF CF Me H SMe H H 1 3 2 3 2 3 CF CH CF HCF FH 0 CF CF Me H SMe H H 2 3 2 3 3 2 3 CF CH CF HCF FH 1 CF CF Me HSOMeH H 0 3 2 3 3 2 3 CF CH CF HCF FH 2 CF CF Me HSOMeH H 1 3 2 3 3 2 3 CF CH CF HCF Cl H 0 CF CF Me HSOMeH H 2 3 2 3 3 2 3 CF CH CF HCF Cl H 1 CF CF Me HSO Me H H 0 3 2 3 3 2 3 2 CF CH CF HCF Cl H 2 CF CF Me HSO Me H H 1 3 2 3 3 2 3 2 CF CH CF HCF Br H 0 CF CF Me HSO Me H H 2 3 2 3 3 2 3 2 CF CH CF HCF Br H 1 CF CF Me H OMe H H 0 3 2 3 3 2 3 CF CH CF HCF Br H 2 CF CF Me H OMe H H 1 3 2 3 3 2 3 CF CH CF HCF IH 0 CF CF Me H OMe H H 2 3 2 3 3 2 3 CF CH CF HCF IH 1 CF CF Me HOCF HH 0 3 2 3 3 2 3 3 CF CH CF HCF IH 2 CF CF Me HOCF HH 1 3 2 3 3 2 3 3 CF CH CF HCF CN H 0 CF CF Me HOCF HH 2 3 2 3 3 2 3 3 CF CH CF HCF CN H 1 CF CF Me HNO HH 0 3 2 3 3 2 3 2 CF CH CF HCF CN H 2 3 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Me HNO HH 1 CF CF Me HHH I 2 2 3 2 2 3 CF CF Me HNO HH 2 CF CF Me HHH Me 0 2 3 2 2 3 CF CF Me HCNH H 0 CF CF Me HHH Me 1 2 3 2 3 CF CF Me HCNH H 1 CF CF Me HHH Me 2 2 3 2 3 CF CF Me HCNH H 2 CF CF Me HHH CF 0 2 3 2 3 3 CF CF Me HHF H 0 CF CF Me HHH CF 1 2 3 2 3 3 CF CF Me HHF H 1 CF CF Me HHH CF 2 2 3 2 3 3 CF CF Me HHF H 2 CF CF Me HHH CF CF 0 2 3 2 3 2 3 CF CF Me HH Cl H 0 CF CF Me HHH CF CF 1 2 3 2 3 2 3 CF CF Me HH Cl H 1 CF CF Me HHH CF CF 2 2 3 2 3 2 3 CF CF Me HH Cl H 2 CF CF Me H H H CF(CF ) 0 2 3 2 3 3 2 CF CF Me HH Br H 0 CF CF Me H H H CF(CF ) 1 2 3 2 3 3 2 CF CF Me HH Br H 1 CF CF Me H H H CF(CF ) 2 2 3 2 3 3 2 CF CF Me HH Br H 2 CF CF Me HHH SMe 0 2 3 2 3 CF CF Me HHI H 0 CF CF Me HHH SMe 1 2 3 2 3 CF CF Me HHI H 1 CF CF Me HHH SMe 2 2 3 2 3 CF CF Me HHI H 2 CF CF Me HHH SOMe 0 2 3 2 3 CF CF Me HH Me H 0 CF CF Me HHH SOMe 1 2 3 2 3 CF CF Me HH Me H 1 CF CF Me HHH SOMe 2 2 3 2 3 CF CF Me HH Me H 2 CF CF Me HHH SO Me 0 2 3 2 3 2 CF CF Me HH CF H 0 CF CF Me HHH SO Me 1 2 3 3 2 3 2 CF CF Me HH CF H 1 CF CF Me HHH SO Me 2 2 3 3 2 3 2 CF CF Me HH CF H 2 CF CF Me HHH OMe 0 2 3 3 2 3 CF CF Me HH CF CF H 0 CF CF Me HHH OMe 1 2 3 2 3 2 3 CF CF Me HH CF CF H 1 CF CF Me HHH OMe 2 2 3 2 3 2 3 CF CF Me HH CF CF H 2 CF CF Me HHH OCF 0 2 3 2 3 2 3 3 CF CF Me H H CF(CF ) H 0 CF CF Me HHH OCF 1 2 3 3 2 2 3 3 CF CF Me H H CF(CF ) H 1 CF CF Me HHH OCF 2 2 3 3 2 2 3 3 CF CF Me H H CF(CF ) H 2 CF CF Me HHH NO 0 2 3 3 2 2 3 2 CF CF Me HH SMe H 0 CF CF Me HHH NO 1 2 3 2 3 2 CF CF Me HH SMe H 1 CF CF Me HHH NO 2 2 3 2 3 2 CF CF Me HH SMe H 2 CF CF Me HHH CN 0 2 3 2 3 CF CF Me H H SOMe H 0 CF CF Me HHH CN 1 2 3 2 3 CF CF Me H H SOMe H 1 CF CF Me HHH CN 2 2 3 2 3 CF CF Me H H SOMe H 2 CF CF Me HFH F 0 2 3 2 3 CF CF Me HH SO Me H 0 CF CF Me HFH F 1 2 3 2 2 3 CF CF Me HH SO Me H 1 CF CF Me HFH F 2 2 3 2 2 3 CF CF Me HH SO Me H 2 CF CF Me HClH Cl 0 2 3 2 2 3 CF CF Me HH OMe H 0 CF CF Me HClH Cl 1 2 3 2 3 CF CF Me HH OMe H 1 CF CF Me HClH Cl 2 2 3 2 3 CF CF Me HH OMe H 2 CF CF Me HBrH Br 0 2 3 2 3 CF CF Me H H OCF H 0 CF CF Me HBrH Br 1 2 3 3 2 3 CF CF Me H H OCF H 1 CF CF Me HBrH Br 2 2 3 3 2 3 CF CF Me H H OCF H 2 CF CF Me HIH I 0 2 3 3 2 3 CF CF Me HH NO H 0 CF CF Me HIH I 1 2 3 2 2 3 CF CF Me HH NO H 1 CF CF Me HIH I 2 2 3 2 2 3 CF CF Me HH NO H 2 CF CF Me HFH Cl 0 2 3 2 2 3 CF CF Me HH CN H 0 CF CF Me HFH Cl 1 2 3 2 3 CF CF Me HH CN H 1 CF CF Me HFH Cl 2 2 3 2 3 CF CF Me HH CN H 2 CF CF Me HFH Br 0 2 3 2 3 CF CF Me HHH F 0 CF CF Me HFH Br 1 2 3 2 3 CF CF Me HHH F 1 CF CF Me HFH Br 2 2 3 2 3 CF CF Me HHH F 2 CF CF Me HFH I 0 2 3 2 3 CF CF Me HHH Cl 0 CF CF Me HFH I 1 2 3 2 3 CF CF Me HHH Cl 1 CF CF Me HFH I 2 2 3 2 3 CF CF Me HHH Cl 2 CF CF Me HClH F 0 2 3 2 3 CF CF Me HHH Br 0 CF CF Me HClH F 1 2 3 2 3 CF CF Me HHH Br 1 CF CF Me HClH F 2 2 3 2 3 CF CF Me HHH Br 2 CF CF Me HClH Br 0 2 3 2 3 CF CF Me HHH I 0 CF CF Me HClH Br 1 2 3 2 3 CF CF Me HHH I 1 CF CF Me HClH Br 2 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Me HClH I 0 CF CF Me HF Cl H 1 2 3 2 3 CF CF Me HClH I 1 CF CF Me HF Cl H 2 2 3 2 3 CF CF Me HClH I 2 CF CF Me HF Br H 0 2 3 2 3 CF CF Me HBrH F 0 CF CF Me HF Br H 1 2 3 2 3 CF CF Me HBrH F 1 CF CF Me HF Br H 2 2 3 2 3 CF CF Me HBrH F 2 CF CF Me HFI H 0 2 3 2 3 CF CF Me HBrH Cl 0 CF CF Me HFI H 1 2 3 2 3 CF CF Me HBrH Cl 1 CF CF Me HFI H 2 2 3 2 3 CF CF Me HBrH Cl 2 CF CF Me HClF H 0 2 3 2 3 CF CF Me HBrH I 0 CF CF Me HClF H 1 2 3 2 3 CF CF Me HBrH I 1 CF CF Me HClF H 2 2 3 2 3 CF CF Me HBrH I 2 CF CF Me HCl Br H 0 2 3 2 3 CF CF Me HIH F 0 CF CF Me HCl Br H 1 2 3 2 3 CF CF Me HIH F 1 CF CF Me HCl Br H 2 2 3 2 3 CF CF Me HIH F 2 CF CF Me HClI H 0 2 3 2 3 CF CF Me HIH Cl 0 CF CF Me HClI H 1 2 3 2 3 CF CF Me HIH Cl 1 CF CF Me HClI H 2 2 3 2 3 CF CF Me HIH Cl 2 CF CF Me HBrF H 0 2 3 2 3 CF CF Me HIH Br 0 CF CF Me HBrF H 1 2 3 2 3 CF CF Me HIH Br 1 CF CF Me HBrF H 2 2 3 2 3 CF CF Me HIH Br 2 CF CF Me HBr Cl H 0 2 3 2 3 CF CF Me HFH CN 0 CF CF Me HBr Cl H 1 2 3 2 3 CF CF Me HFH CN 1 CF CF Me HBr Cl H 2 2 3 2 3 CF CF Me HFH CN 2 CF CF Me HBrI H 0 2 3 2 3 CF CF Me HClH CN 0 CF CF Me HBrI H 1 2 3 2 3 CF CF Me HClH CN 1 CF CF Me HBrI H 2 2 3 2 3 CF CF Me HClH CN 2 CF CF Me HIF H 0 2 3 2 3 CF CF Me HBrH CN 0 CF CF Me HIF H 1 2 3 2 3 CF CF Me HBrH CN 1 CF CF Me HIF H 2 2 3 2 3 CF CF Me HBrH CN 2 CF CF Me HI Cl H 0 2 3 2 3 CF CF Me HIH CN 0 CF CF Me HI Cl H 1 2 3 2 3 CF CF Me HIH CN 1 CF CF Me HI Cl H 2 2 3 2 3 CF CF Me HIH CN 2 CF CF Me HI Br H 0 2 3 2 3 CF CF Me HCF HF 0 CF CF Me HI Br H 1 2 3 3 2 3 CF CF Me HCF HF 1 CF CF Me HI Br H 2 2 3 3 2 3 CF CF Me HCF HF 2 CF CF Me HF CN H 0 2 3 3 2 3 CF CF Me HCF HCl 0 CF CF Me HF CN H 1 2 3 3 2 3 CF CF Me HCF HCl 1 CF CF Me HF CN H 2 2 3 3 2 3 CF CF Me HCF HCl 2 CF CF Me HCl CN H 0 2 3 3 2 3 CF CF Me HCF HBr 0 CF CF Me HCl CN H 1 2 3 3 2 3 CF CF Me HCF HBr 1 CF CF Me HCl CN H 2 2 3 3 2 3 CF CF Me HCF HBr 2 CF CF Me HBr CN H 0 2 3 3 2 3 CF CF Me HCF HI 0 CF CF Me HBr CN H 1 2 3 3 2 3 CF CF Me HCF HI 1 CF CF Me HBr CN H 2 2 3 3 2 3 CF CF Me HCF HI 2 CF CF Me HI CN H 0 2 3 3 2 3 CF CF Me HCF HCN 0 CF CF Me HI CN H 1 2 3 3 2 3 CF CF Me HCF HCN 1 CF CF Me HI CN H 2 2 3 3 2 3 CF CF Me HCF HCN 2 CF CF Me HCF FH 0 2 3 3 2 3 3 CF CF Me HFF H 0 CF CF Me HCF FH 1 2 3 2 3 3 CF CF Me HFF H 1 CF CF Me HCF FH 2 2 3 2 3 3 CF CF Me HFF H 2 CF CF Me HCF Cl H 0 2 3 2 3 3 CF CF Me HCl Cl H 0 CF CF Me HCF Cl H 1 2 3 2 3 3 CF CF Me HCl Cl H 1 CF CF Me HCF Cl H 2 2 3 2 3 3 CF CF Me HCl Cl H 2 CF CF Me HCF Br H 0 2 3 2 3 3 CF CF Me HBr Br H 0 CF CF Me HCF Br H 1 2 3 2 3 3 CF CF Me HBr Br H 1 CF CF Me HCF Br H 2 2 3 2 3 3 CF CF Me HBr Br H 2 CF CF Me HCF IH 0 2 3 2 3 3 CF CF Me HII H 0 CF CF Me HCF IH 1 2 3 2 3 3 CF CF Me HII H 1 CF CF Me HCF IH 2 2 3 2 3 3 CF CF Me HII H 2 CF CF Me HCF CN H 0 2 3 2 3 3 CF CF Me HF Cl H 0 CF CF Me HCF CN H 1 2 3 2 3 3 CF CF Me HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Et HHH H 0 CF CF Et HNO HH 1 2 3 2 3 2 CF CF Et HHH H 1 CF CF Et HNO HH 2 2 3 2 3 2 CF CF Et HHH H 2 CF CF Et HCNH H 0 2 3 2 3 CF CF Et FHH H 0 CF CF Et HCNH H 1 2 3 2 3 CF CF Et FHH H 1 CF CF Et HCNH H 2 2 3 2 3 CF CF Et FHH H 2 CF CF Et HHF H 0 2 3 2 3 CF CF Et Cl H H H 0 CF CF Et HHF H 1 2 3 2 3 CF CF Et Cl H H H 1 CF CF Et HHF H 2 2 3 2 3 CF CF Et Cl H H H 2 CF CF Et HH Cl H 0 2 3 2 3 CF CF Et Br H H H 0 CF CF Et HH Cl H 1 2 3 2 3 CF CF Et Br H H H 1 CF CF Et HH Cl H 2 2 3 2 3 CF CF Et Br H H H 2 CF CF Et HH Br H 0 2 3 2 3 CF CF Et IHH H 0 CF CF Et HH Br H 1 2 3 2 3 CF CF Et IHH H 1 CF CF Et HH Br H 2 2 3 2 3 CF CF Et IHH H 2 CF CF Et HHI H 0 2 3 2 3 CF CF Et Me H H H 0 CF CF Et HHI H 1 2 3 2 3 CF CF Et Me H H H 1 CF CF Et HHI H 2 2 3 2 3 CF CF Et Me H H H 2 CF CF Et HH Me H 0 2 3 2 3 CF CF Et CF HH H 0 CF CF Et HH Me H 1 2 3 3 2 3 CF CF Et CF HH H 1 CF CF Et HH Me H 2 2 3 3 2 3 CF CF Et CF HH H 2 CF CF Et HH CF H 0 2 3 3 2 3 3 CF CF Et HFH H 0 CF CF Et HH CF H 1 2 3 2 3 3 CF CF Et HFH H 1 CF CF Et HH CF H 2 2 3 2 3 3 CF CF Et HFH H 2 CF CF Et HH CF CF H 0 2 3 2 3 2 3 CF CF Et HClH H 0 CF CF Et HH CF CF H 1 2 3 2 3 2 3 CF CF Et HClH H 1 CF CF Et HH CF CF H 2 2 3 2 3 2 3 CF CF Et HClH H 2 CF CF Et H H CF(CF ) H 0 2 3 2 3 3 2 CF CF Et HBrH H 0 CF CF Et H H CF(CF ) H 1 2 3 2 3 3 2 CF CF Et HBrH H 1 CF CF Et H H CF(CF ) H 2 2 3 2 3 3 2 CF CF Et HBrH H 2 CF CF Et HH SMe H 0 2 3 2 3 CF CF Et HIH H 0 CF CF Et HH SMe H 1 2 3 2 3 CF CF Et HIH H 1 CF CF Et HH SMe H 2 2 3 2 3 CF CF Et HIH H 2 CF CF Et H H SOMe H 0 2 3 2 3 CF CF Et HMeH H 0 CF CF Et H H SOMe H 1 2 3 2 3 CF CF Et HMeH H 1 CF CF Et H H SOMe H 2 2 3 2 3 CF CF Et HMeH H 2 CF CF Et HH SO Me H 0 2 3 2 3 2 CF CF Et HCF HH 0 CF CF Et HH SO Me H 1 2 3 3 2 3 2 CF CF Et HCF HH 1 CF CF Et HH SO Me H 2 2 3 3 2 3 2 CF CF Et HCF HH 2 CF CF Et HH OMe H 0 2 3 3 2 3 CF CF Et HCF CF HH 0 CF CF Et HH OMe H 1 2 3 2 3 2 3 CF CF Et HCF CF HH 1 CF CF Et HH OMe H 2 2 3 2 3 2 3 CF CF Et HCF CF HH 2 CF CF Et H H OCF H 0 2 3 2 3 2 3 3 CF CF Et H CF(CF ) HH 0 CF CF Et H H OCF H 1 2 3 3 2 2 3 3 CF CF Et H CF(CF ) HH 1 CF CF Et H H OCF H 2 2 3 3 2 2 3 3 CF CF Et H CF(CF ) HH 2 CF CF Et HH NO H 0 2 3 3 2 2 3 2 CF CF Et H SMe H H 0 CF CF Et HH NO H 1 2 3 2 3 2 CF CF Et H SMe H H 1 CF CF Et HH NO H 2 2 3 2 3 2 CF CF Et H SMe H H 2 CF CF Et HH CN H 0 2 3 2 3 CF CF Et HSOMeH H 0 CF CF Et HH CN H 1 2 3 2 3 CF CF Et HSOMeH H 1 CF CF Et HH CN H 2 2 3 2 3 CF CF Et HSOMeH H 2 CF CF Et HHH F 0 2 3 2 3 CF CF Et HSO Me H H 0 CF CF Et HHH F 1 2 3 2 2 3 CF CF Et HSO Me H H 1 CF CF Et HHH F 2 2 3 2 2 3 CF CF Et HSO Me H H 2 CF CF Et HHH Cl 0 2 3 2 2 3 CF CF Et H OMe H H 0 CF CF Et HHH Cl 1 2 3 2 3 CF CF Et H OMe H H 1 CF CF Et HHH Cl 2 2 3 2 3 CF CF Et H OMe H H 2 CF CF Et HHH Br 0 2 3 2 3 CF CF Et HOCF HH 0 CF CF Et HHH Br 1 2 3 3 2 3 CF CF Et HOCF HH 1 CF CF Et HHH Br 2 2 3 3 2 3 CF CF Et HOCF HH 2 CF CF Et HHH I 0 2 3 3 2 3 CF CF Et HNO HH 0 CF CF Et HHH I 1 2 3 2 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Et HHH I 2 CF CF Et HClH I 0 2 3 2 3 CF CF Et HHH Me 0 CF CF Et HClH I 1 2 3 2 3 CF CF Et HHH Me 1 CF CF Et HClH I 2 2 3 2 3 CF CF Et HHH Me 2 CF CF Et HBrH F 0 2 3 2 3 CF CF Et HHH CF 0 CF CF Et HBrH F 1 2 3 3 2 3 CF CF Et HHH CF 1 CF CF Et HBrH F 2 2 3 3 2 3 CF CF Et HHH CF 2 CF CF Et HBrH Cl 0 2 3 3 2 3 CF CF Et HHH CF CF 0 CF CF Et HBrH Cl 1 2 3 2 3 2 3 CF CF Et HHH CF CF 1 CF CF Et HBrH Cl 2 2 3 2 3 2 3 CF CF Et HHH CF CF 2 CF CF Et HBrH I 0 2 3 2 3 2 3 CF CF Et H H H CF(CF ) 0 CF CF Et HBrH I 1 2 3 3 2 2 3 CF CF Et H H H CF(CF ) 1 CF CF Et HBrH I 2 2 3 3 2 2 3 CF CF Et H H H CF(CF ) 2 CF CF Et HIH F 0 2 3 3 2 2 3 CF CF Et HHH SMe 0 CF CF Et HIH F 1 2 3 2 3 CF CF Et HHH SMe 1 CF CF Et HIH F 2 2 3 2 3 CF CF Et HHH SMe 2 CF CF Et HIH Cl 0 2 3 2 3 CF CF Et HHH SOMe 0 CF CF Et HIH Cl 1 2 3 2 3 CF CF Et HHH SOMe 1 CF CF Et HIH Cl 2 2 3 2 3 CF CF Et HHH SOMe 2 CF CF Et HIH Br 0 2 3 2 3 CF CF Et HHH SO Me 0 CF CF Et HIH Br 1 2 3 2 2 3 CF CF Et HHH SO Me 1 CF CF Et HIH Br 2 2 3 2 2 3 CF CF Et HHH SO Me 2 CF CF Et HFH CN 0 2 3 2 2 3 CF CF Et HHH OMe 0 CF CF Et HFH CN 1 2 3 2 3 CF CF Et HHH OMe 1 CF CF Et HFH CN 2 2 3 2 3 CF CF Et HHH OMe 2 CF CF Et HClH CN 0 2 3 2 3 CF CF Et HHH OCF 0 CF CF Et HClH CN 1 2 3 3 2 3 CF CF Et HHH OCF 1 CF CF Et HClH CN 2 2 3 3 2 3 CF CF Et HHH OCF 2 CF CF Et HBrH CN 0 2 3 3 2 3 CF CF Et HHH NO 0 CF CF Et HBrH CN 1 2 3 2 2 3 CF CF Et HHH NO 1 CF CF Et HBrH CN 2 2 3 2 2 3 CF CF Et HHH NO 2 CF CF Et HIH CN 0 2 3 2 2 3 CF CF Et HHH CN 0 CF CF Et HIH CN 1 2 3 2 3 CF CF Et HHH CN 1 CF CF Et HIH CN 2 2 3 2 3 CF CF Et HHH CN 2 CF CF Et HCF HF 0 2 3 2 3 3 CF CF Et HFH F 0 CF CF Et HCF HF 1 2 3 2 3 3 CF CF Et HFH F 1 CF CF Et HCF HF 2 2 3 2 3 3 CF CF Et HFH F 2 CF CF Et HCF HCl 0 2 3 2 3 3 CF CF Et HClH Cl 0 CF CF Et HCF HCl 1 2 3 2 3 3 CF CF Et HClH Cl 1 CF CF Et HCF HCl 2 2 3 2 3 3 CF CF Et HClH Cl 2 CF CF Et HCF HBr 0 2 3 2 3 3 CF CF Et HBrH Br 0 CF CF Et HCF HBr 1 2 3 2 3 3 CF CF Et HBrH Br 1 CF CF Et HCF HBr 2 2 3 2 3 3 CF CF Et HBrH Br 2 CF CF Et HCF HI 0 2 3 2 3 3 CF CF Et HIH I 0 CF CF Et HCF HI 1 2 3 2 3 3 CF CF Et HIH I 1 CF CF Et HCF HI 2 2 3 2 3 3 CF CF Et HIH I 2 CF CF Et HCF HCN 0 2 3 2 3 3 CF CF Et HFH Cl 0 CF CF Et HCF HCN 1 2 3 2 3 3 CF CF Et HFH Cl 1 CF CF Et HCF HCN 2 2 3 2 3 3 CF CF Et HFH Cl 2 CF CF Et HFF H 0 2 3 2 3 CF CF Et HFH Br 0 CF CF Et HFF H 1 2 3 2 3 CF CF Et HFH Br 1 CF CF Et HFF H 2 2 3 2 3 CF CF Et HFH Br 2 CF CF Et HCl Cl H 0 2 3 2 3 CF CF Et HFH I 0 CF CF Et HCl Cl H 1 2 3 2 3 CF CF Et HFH I 1 CF CF Et HCl Cl H 2 2 3 2 3 CF CF Et HFH I 2 CF CF Et HBr Br H 0 2 3 2 3 CF CF Et HClH F 0 CF CF Et HBr Br H 1 2 3 2 3 CF CF Et HClH F 1 CF CF Et HBr Br H 2 2 3 2 3 CF CF Et HClH F 2 CF CF Et HII H 0 2 3 2 3 CF CF Et HClH Br 0 CF CF Et HII H 1 2 3 2 3 CF CF Et HClH Br 1 CF CF Et HII H 2 2 3 2 3 CF CF Et HClH Br 2 CF CF Et HF Cl H 0 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Et HF Cl H 1 CF CF Pr HHH H 0 2 3 2 3 CF CF Et HF Cl H 2 CF CF HHH H 1 2 3 2 3 CF CF Et HF Br H 0 CF CF Pr HHH H 2 2 3 2 3 CF CF Et HF Br H 1 CF CF FHH H 0 2 3 2 3 CF CF Et HF Br H 2 CF CF Pr FHH H 1 2 3 2 3 CF CF Et HFI H 0 CF CF FHH H 2 2 3 2 3 CF CF Et HFI H 1 CF CF Pr Cl H H H 0 2 3 2 3 CF CF Et HFI H 2 CF CF Pr Cl H H H 1 2 3 2 3 CF CF Et HClF H 0 CF CF Pr Cl H H H 2 2 3 2 3 CF CF Et HClF H 1 CF CF Pr Br H H H 0 2 3 2 3 CF CF Et HClF H 2 CF CF Br H H H 1 2 3 2 3 CF CF Et HCl Br H 0 CF CF Pr Br H H H 2 2 3 2 3 CF CF Et HCl Br H 1 CF CF IHH H 0 2 3 2 3 CF CF Et HCl Br H 2 CF CF Pr IHH H 1 2 3 2 3 CF CF Et HClI H 0 CF CF IHH H 2 2 3 2 3 CF CF Et HClI H 1 CF CF Pr Me H H H 0 2 3 2 3 CF CF Et HClI H 2 CF CF Pr Me H H H 1 2 3 2 3 CF CF Et HBrF H 0 CF CF Pr Me H H H 2 2 3 2 3 CF CF Et HBrF H 1 CF CF Pr CF HH H 0 2 3 2 3 3 CF CF Et HBrF H 2 CF CF CF HH H 1 2 3 2 3 3 CF CF Et HBr Cl H 0 CF CF Pr CF HH H 2 2 3 2 3 3 CF CF Et HBr Cl H 1 CF CF HFH H 0 2 3 2 3 CF CF Et HBr Cl H 2 CF CF Pr HFH H 1 2 3 2 3 CF CF Et HBrI H 0 CF CF HFH H 2 2 3 2 3 CF CF Et HBrI H 1 CF CF Pr HClH H 0 2 3 2 3 CF CF Et HBrI H 2 CF CF HClH H 1 2 3 2 3 CF CF Et HIF H 0 CF CF Pr HClH H 2 2 3 2 3 CF CF Et HIF H 1 CF CF Pr HBrH H 0 2 3 2 3 CF CF Et HIF H 2 CF CF Pr HBrH H 1 2 3 2 3 CF CF Et HI Cl H 0 CF CF Pr HBrH H 2 2 3 2 3 CF CF Et HI Cl H 1 CF CF HIH H 0 2 3 2 3 CF CF Et HI Cl H 2 CF CF Pr HIH H 1 2 3 2 3 CF CF Et HI Br H 0 CF CF HIH H 2 2 3 2 3 CF CF Et HI Br H 1 CF CF Pr HMeH H 0 2 3 2 3 CF CF Et HI Br H 2 CF CF HMeH H 1 2 3 2 3 CF CF Et HF CN H 0 CF CF Pr HMeH H 2 2 3 2 3 CF CF Et HF CN H 1 CF CF Pr HCF HH 0 2 3 2 3 3 CF CF Et HF CN H 2 CF CF Pr HCF HH 1 2 3 2 3 3 CF CF Et HCl CN H 0 CF CF Pr HCF HH 2 2 3 2 3 3 CF CF Et HCl CN H 1 CF CF HCF CF HH 0 2 3 2 3 2 3 CF CF Et HCl CN H 2 CF CF Pr HCF CF HH 1 2 3 2 3 2 3 CF CF Et HBr CN H 0 CF CF HCF CF HH 2 2 3 2 3 2 3 CF CF Et HBr CN H 1 CF CF Pr H CF(CF ) HH 0 2 3 2 3 3 2 CF CF Et HBr CN H 2 CF CF H CF(CF ) HH 1 2 3 2 3 3 2 CF CF Et HI CN H 0 CF CF Pr H CF(CF ) HH 2 2 3 2 3 3 2 CF CF Et HI CN H 1 CF CF H SMe H H 0 2 3 2 3 CF CF Et HI CN H 2 CF CF Pr H SMe H H 1 2 3 2 3 CF CF Et HCF FH 0 CF CF H SMe H H 2 2 3 3 2 3 CF CF Et HCF FH 1 CF CF Pr HSOMeH H 0 2 3 3 2 3 CF CF Et HCF FH 2 CF CF Pr HSOMeH H 1 2 3 3 2 3 CF CF Et HCF Cl H 0 CF CF HSOMeH H 2 2 3 3 2 3 CF CF Et HCF Cl H 1 CF CF Pr HSO Me H H 0 2 3 3 2 3 2 CF CF Et HCF Cl H 2 CF CF HSO Me H H 1 2 3 3 2 3 2 CF CF Et HCF Br H 0 CF CF Pr HSO Me H H 2 2 3 3 2 3 2 CF CF Et HCF Br H 1 CF CF H OMe H H 0 2 3 3 2 3 CF CF Et HCF Br H 2 CF CF Pr H OMe H H 1 2 3 3 2 3 CF CF Et HCF IH 0 CF CF Pr H OMe H H 2 2 3 3 2 3 CF CF Et HCF IH 1 CF CF Pr HOCF HH 0 2 3 3 2 3 3 CF CF Et HCF IH 2 CF CF Pr HOCF HH 1 2 3 3 2 3 3 CF CF Et HCF CN H 0 CF CF Pr HOCF HH 2 2 3 3 2 3 3 CF CF Et HCF CN H 1 CF CF Pr HNO HH 0 2 3 3 2 3 2 CF CF Et HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Pr HNO HH 1 CF CF Pr HHH I 2 2 3 2 2 3 CF CF HNO HH 2 CF CF HHH Me 0 Pr Pr 2 3 2 2 3 CF CF Pr HCNH H 0 CF CF Pr HHH Me 1 2 3 2 3 CF CF HCNH H 1 CF CF HHH Me 2 Pr Pr 2 3 2 3 CF CF Pr HCNH H 2 CF CF Pr HHH CF 0 2 3 2 3 3 CF CF Pr HHF H 0 CF CF Pr HHH CF 1 2 3 2 3 3 CF CF Pr HHF H 1 CF CF Pr HHH CF 2 2 3 2 3 3 CF CF Pr HHF H 2 CF CF Pr HHH CF CF 0 2 3 2 3 2 3 CF CF HH Cl H 0 CF CF HHH CF CF 1 Pr Pr 2 3 2 3 2 3 CF CF Pr HH Cl H 1 CF CF Pr HHH CF CF 2 2 3 2 3 2 3 CF CF HH Cl H 2 CF CF H H H CF(CF ) 0 Pr Pr 2 3 2 3 3 2 CF CF Pr HH Br H 0 CF CF Pr H H H CF(CF ) 1 2 3 2 3 3 2 CF CF HH Br H 1 CF CF H H H CF(CF ) 2 Pr Pr 2 3 2 3 3 2 CF CF Pr HH Br H 2 CF CF Pr HHH SMe 0 2 3 2 3 CF CF HHI H 0 CF CF HHH SMe 1 Pr Pr 2 3 2 3 CF CF Pr HHI H 1 CF CF Pr HHH SMe 2 2 3 2 3 CF CF Pr HHI H 2 CF CF Pr HHH SOMe 0 2 3 2 3 CF CF HH Me H 0 CF CF HHH SOMe 1 Pr Pr 2 3 2 3 CF CF Pr HH Me H 1 CF CF Pr HHH SOMe 2 2 3 2 3 CF CF HH Me H 2 CF CF HHH SO Me 0 Pr Pr 2 3 2 3 2 CF CF Pr HH CF H 0 CF CF Pr HHH SO Me 1 2 3 3 2 3 2 CF CF HH CF H 1 CF CF HHH SO Me 2 Pr Pr 2 3 3 2 3 2 CF CF Pr HH CF H 2 CF CF Pr HHH OMe 0 2 3 3 2 3 CF CF Pr HH CF CF H 0 CF CF Pr HHH OMe 1 2 3 2 3 2 3 CF CF Pr HH CF CF H 1 CF CF Pr HHH OMe 2 2 3 2 3 2 3 CF CF Pr HH CF CF H 2 CF CF Pr HHH OCF 0 2 3 2 3 2 3 3 CF CF H H CF(CF ) H 0 CF CF HHH OCF 1 Pr Pr 2 3 3 2 2 3 3 CF CF Pr H H CF(CF ) H 1 CF CF Pr HHH OCF 2 2 3 3 2 2 3 3 CF CF H H CF(CF ) H 2 CF CF HHH NO 0 Pr Pr 2 3 3 2 2 3 2 CF CF Pr HH SMe H 0 CF CF Pr HHH NO 1 2 3 2 3 2 CF CF HH SMe H 1 CF CF HHH NO 2 Pr Pr 2 3 2 3 2 CF CF Pr HH SMe H 2 CF CF Pr HHH CN 0 2 3 2 3 CF CF Pr H H SOMe H 0 CF CF Pr HHH CN 1 2 3 2 3 CF CF Pr H H SOMe H 1 CF CF Pr HHH CN 2 2 3 2 3 CF CF Pr H H SOMe H 2 CF CF Pr HFH F 0 2 3 2 3 CF CF HH SO Me H 0 CF CF HFH F 1 Pr Pr 2 3 2 2 3 CF CF Pr HH SO Me H 1 CF CF Pr HFH F 2 2 3 2 2 3 CF CF HH SO Me H 2 CF CF HClH Cl 0 Pr Pr 2 3 2 2 3 CF CF Pr HH OMe H 0 CF CF Pr HClH Cl 1 2 3 2 3 CF CF HH OMe H 1 CF CF HClH Cl 2 Pr Pr 2 3 2 3 CF CF Pr HH OMe H 2 CF CF Pr HBrH Br 0 2 3 2 3 CF CF H H OCF H 0 CF CF HBrH Br 1 Pr Pr 2 3 3 2 3 CF CF Pr H H OCF H 1 CF CF Pr HBrH Br 2 2 3 3 2 3 CF CF Pr H H OCF H 2 CF CF Pr HIH I 0 2 3 3 2 3 CF CF HH NO H 0 CF CF HIH I 1 Pr Pr 2 3 2 2 3 CF CF Pr HH NO H 1 CF CF Pr HIH I 2 2 3 2 2 3 CF CF HH NO H 2 CF CF HFH Cl 0 Pr Pr 2 3 2 2 3 CF CF Pr HH CN H 0 CF CF Pr HFH Cl 1 2 3 2 3 CF CF HH CN H 1 CF CF HFH Cl 2 Pr Pr 2 3 2 3 CF CF Pr HH CN H 2 CF CF Pr HFH Br 0 2 3 2 3 CF CF Pr HHH F 0 CF CF Pr HFH Br 1 2 3 2 3 CF CF Pr HHH F 1 CF CF Pr HFH Br 2 2 3 2 3 CF CF Pr HHH F 2 CF CF Pr HFH I 0 2 3 2 3 CF CF HHH Cl 0 CF CF HFH I 1 Pr Pr 2 3 2 3 CF CF Pr HHH Cl 1 CF CF Pr HFH I 2 2 3 2 3 CF CF HHH Cl 2 CF CF HClH F 0 Pr Pr 2 3 2 3 CF CF Pr HHH Br 0 CF CF Pr HClH F 1 2 3 2 3 CF CF HHH Br 1 CF CF HClH F 2 Pr Pr 2 3 2 3 CF CF Pr HHH Br 2 CF CF Pr HClH Br 0 2 3 2 3 CF CF HHH I 0 CF CF HClH Br 1 Pr Pr 2 3 2 3 CF CF Pr HHH I 1 CF CF Pr HClH Br 2 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Pr HClH I 0 CF CF Pr HF Cl H 1 2 3 2 3 CF CF HClH I 1 CF CF HF Cl H 2 Pr Pr 2 3 2 3 CF CF Pr HClH I 2 CF CF Pr HF Br H 0 2 3 2 3 CF CF HBrH F 0 CF CF HF Br H 1 Pr Pr 2 3 2 3 CF CF Pr HBrH F 1 CF CF Pr HF Br H 2 2 3 2 3 CF CF HBrH F 2 CF CF HFI H 0 Pr Pr 2 3 2 3 CF CF Pr HBrH Cl 0 CF CF Pr HFI H 1 2 3 2 3 CF CF Pr HBrH Cl 1 CF CF Pr HFI H 2 2 3 2 3 CF CF Pr HBrH Cl 2 CF CF Pr HClF H 0 2 3 2 3 CF CF Pr HBrH I 0 CF CF Pr HClF H 1 2 3 2 3 CF CF HBrH I 1 CF CF HClF H 2 Pr Pr 2 3 2 3 CF CF Pr HBrH I 2 CF CF Pr HCl Br H 0 2 3 2 3 CF CF HIH F 0 CF CF HCl Br H 1 Pr Pr 2 3 2 3 CF CF Pr HIH F 1 CF CF Pr HCl Br H 2 2 3 2 3 CF CF HIH F 2 CF CF HClI H 0 Pr Pr 2 3 2 3 CF CF Pr HIH Cl 0 CF CF Pr HClI H 1 2 3 2 3 CF CF Pr HIH Cl 1 CF CF Pr HClI H 2 2 3 2 3 CF CF Pr HIH Cl 2 CF CF Pr HBrF H 0 2 3 2 3 CF CF Pr HIH Br 0 CF CF Pr HBrF H 1 2 3 2 3 CF CF HIH Br 1 CF CF HBrF H 2 Pr Pr 2 3 2 3 CF CF Pr HIH Br 2 CF CF Pr HBr Cl H 0 2 3 2 3 CF CF HFH CN 0 CF CF HBr Cl H 1 Pr Pr 2 3 2 3 CF CF Pr HFH CN 1 CF CF Pr HBr Cl H 2 2 3 2 3 CF CF HFH CN 2 CF CF HBrI H 0 Pr Pr 2 3 2 3 CF CF Pr HClH CN 0 CF CF Pr HBrI H 1 2 3 2 3 CF CF HClH CN 1 CF CF HBrI H 2 Pr Pr 2 3 2 3 CF CF Pr HClH CN 2 CF CF Pr HIF H 0 2 3 2 3 CF CF Pr HBrH CN 0 CF CF Pr HIF H 1 2 3 2 3 CF CF Pr HBrH CN 1 CF CF Pr HIF H 2 2 3 2 3 CF CF Pr HBrH CN 2 CF CF Pr HI Cl H 0 2 3 2 3 CF CF HIH CN 0 CF CF HI Cl H 1 Pr Pr 2 3 2 3 CF CF Pr HIH CN 1 CF CF Pr HI Cl H 2 2 3 2 3 CF CF HIH CN 2 CF CF HI Br H 0 Pr Pr 2 3 2 3 CF CF Pr HCF HF 0 CF CF Pr HI Br H 1 2 3 3 2 3 CF CF HCF HF 1 CF CF HI Br H 2 Pr Pr 2 3 3 2 3 CF CF Pr HCF HF 2 CF CF Pr HF CN H 0 2 3 3 2 3 CF CF Pr HCF HCl 0 CF CF Pr HF CN H 1 2 3 3 2 3 CF CF Pr HCF HCl 1 CF CF Pr HF CN H 2 2 3 3 2 3 CF CF Pr HCF HCl 2 CF CF Pr HCl CN H 0 2 3 3 2 3 CF CF HCF HBr 0 CF CF HCl CN H 1 Pr Pr 2 3 3 2 3 CF CF Pr HCF HBr 1 CF CF Pr HCl CN H 2 2 3 3 2 3 CF CF HCF HBr 2 CF CF HBr CN H 0 Pr Pr 2 3 3 2 3 CF CF Pr HCF HI 0 CF CF Pr HBr CN H 1 2 3 3 2 3 CF CF HCF HI 1 CF CF HBr CN H 2 Pr Pr 2 3 3 2 3 CF CF Pr HCF HI 2 CF CF Pr HI CN H 0 2 3 3 2 3 CF CF HCF HCN 0 CF CF HI CN H 1 Pr Pr 2 3 3 2 3 CF CF Pr HCF HCN 1 CF CF Pr HI CN H 2 2 3 3 2 3 CF CF HCF HCN 2 CF CF HCF FH 0 Pr Pr 2 3 3 2 3 3 CF CF Pr HFF H 0 CF CF Pr HCF FH 1 2 3 2 3 3 CF CF Pr HFF H 1 CF CF Pr HCF FH 2 2 3 2 3 3 CF CF HFF H 2 CF CF HCF Cl H 0 Pr Pr 2 3 2 3 3 CF CF Pr HCl Cl H 0 CF CF Pr HCF Cl H 1 2 3 2 3 3 CF CF HCl Cl H 1 CF CF HCF Cl H 2 Pr Pr 2 3 2 3 3 CF CF Pr HCl Cl H 2 CF CF Pr HCF Br H 0 2 3 2 3 3 CF CF HBr Br H 0 CF CF HCF Br H 1 Pr Pr 2 3 2 3 3 CF CF Pr HBr Br H 1 CF CF Pr HCF Br H 2 2 3 2 3 3 CF CF Pr HBr Br H 2 CF CF Pr HCF IH 0 2 3 2 3 3 CF CF Pr HII H 0 CF CF Pr HCF IH 1 2 3 2 3 3 CF CF Pr HII H 1 CF CF Pr HCF IH 2 2 3 2 3 3 CF CF Pr HII H 2 CF CF Pr HCF CN H 0 2 3 2 3 3 CF CF Pr HF Cl H 0 CF CF Pr HCF CN H 1 2 3 2 3 3 CF CF HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Pr HHH H 0 CF CF Pr HNO HH 1 2 3 2 3 2 CF CF HHH H 1 CF CF HNO HH 2 Pr Pr 2 3 2 3 2 CF CF Pr HHH H 2 CF CF Pr HCNH H 0 2 3 2 3 CF CF FHH H 0 CF CF HCNH H 1 Pr Pr 2 3 2 3 CF CF Pr FHH H 1 CF CF Pr HCNH H 2 2 3 2 3 CF CF Pr FHH H 2 CF CF Pr HHF H 0 2 3 2 3 CF CF Pr Cl H H H 0 CF CF Pr HHF H 1 2 3 2 3 CF CF Pr Cl H H H 1 CF CF Pr HHF H 2 2 3 2 3 CF CF Cl H H H 2 CF CF HH Cl H 0 Pr Pr 2 3 2 3 CF CF Pr Br H H H 0 CF CF Pr HH Cl H 1 2 3 2 3 CF CF Br H H H 1 CF CF HH Cl H 2 Pr Pr 2 3 2 3 CF CF Pr Br H H H 2 CF CF Pr HH Br H 0 2 3 2 3 CF CF IHH H 0 CF CF HH Br H 1 Pr Pr 2 3 2 3 CF CF Pr IHH H 1 CF CF Pr HH Br H 2 2 3 2 3 CF CF IHH H 2 CF CF HHI H 0 Pr Pr 2 3 2 3 CF CF Pr Me H H H 0 CF CF Pr HHI H 1 2 3 2 3 CF CF Pr Me H H H 1 CF CF Pr HHI H 2 2 3 2 3 CF CF Me H H H 2 CF CF HH Me H 0 Pr Pr 2 3 2 3 CF CF Pr CF HH H 0 CF CF Pr HH Me H 1 2 3 3 2 3 CF CF CF HH H 1 CF CF HH Me H 2 Pr Pr 2 3 3 2 3 CF CF Pr CF HH H 2 CF CF Pr HH CF H 0 2 3 3 2 3 3 CF CF HFH H 0 CF CF HH CF H 1 Pr Pr 2 3 2 3 3 CF CF Pr HFH H 1 CF CF Pr HH CF H 2 2 3 2 3 3 CF CF Pr HFH H 2 CF CF Pr HH CF CF H 0 2 3 2 3 2 3 CF CF Pr HClH H 0 CF CF Pr HH CF CF H 1 2 3 2 3 2 3 CF CF Pr HClH H 1 CF CF Pr HH CF CF H 2 2 3 2 3 2 3 CF CF HClH H 2 CF CF H H CF(CF ) H 0 Pr Pr 2 3 2 3 3 2 CF CF Pr HBrH H 0 CF CF Pr H H CF(CF ) H 1 2 3 2 3 3 2 CF CF HBrH H 1 CF CF H H CF(CF ) H 2 Pr Pr 2 3 2 3 3 2 CF CF Pr HBrH H 2 CF CF Pr HH SMe H 0 2 3 2 3 CF CF HIH H 0 CF CF HH SMe H 1 Pr Pr 2 3 2 3 CF CF Pr HIH H 1 CF CF Pr HH SMe H 2 2 3 2 3 CF CF Pr HIH H 2 CF CF Pr H H SOMe H 0 2 3 2 3 CF CF Pr HMeH H 0 CF CF Pr H H SOMe H 1 2 3 2 3 CF CF Pr HMeH H 1 CF CF Pr H H SOMe H 2 2 3 2 3 CF CF HMeH H 2 CF CF HH SO Me H 0 Pr Pr 2 3 2 3 2 CF CF Pr HCF HH 0 CF CF Pr HH SO Me H 1 2 3 3 2 3 2 CF CF HCF HH 1 CF CF HH SO Me H 2 Pr Pr 2 3 3 2 3 2 CF CF Pr HCF HH 2 CF CF Pr HH OMe H 0 2 3 3 2 3 CF CF HCF CF HH 0 CF CF HH OMe H 1 Pr Pr 2 3 2 3 2 3 CF CF Pr HCF CF HH 1 CF CF Pr HH OMe H 2 2 3 2 3 2 3 CF CF HCF CF HH 2 CF CF H H OCF H 0 Pr Pr 2 3 2 3 2 3 3 CF CF Pr H CF(CF ) HH 0 CF CF Pr H H OCF H 1 2 3 3 2 2 3 3 CF CF Pr H CF(CF ) HH 1 CF CF Pr H H OCF H 2 2 3 3 2 2 3 3 CF CF H CF(CF ) HH 2 CF CF HH NO H 0 Pr Pr 2 3 3 2 2 3 2 CF CF Pr H SMe H H 0 CF CF Pr HH NO H 1 2 3 2 3 2 CF CF H SMe H H 1 CF CF HH NO H 2 Pr Pr 2 3 2 3 2 CF CF Pr H SMe H H 2 CF CF Pr HH CN H 0 2 3 2 3 CF CF HSOMeH H 0 CF CF HH CN H 1 Pr Pr 2 3 2 3 CF CF Pr HSOMeH H 1 CF CF Pr HH CN H 2 2 3 2 3 CF CF Pr HSOMeH H 2 CF CF Pr HHH F 0 2 3 2 3 CF CF Pr HSO Me H H 0 CF CF Pr HHH F 1 2 3 2 2 3 CF CF Pr HSO Me H H 1 CF CF Pr HHH F 2 2 3 2 2 3 CF CF HSO Me H H 2 CF CF HHH Cl 0 Pr Pr 2 3 2 2 3 CF CF Pr H OMe H H 0 CF CF Pr HHH Cl 1 2 3 2 3 CF CF H OMe H H 1 CF CF HHH Cl 2 Pr Pr 2 3 2 3 CF CF Pr H OMe H H 2 CF CF Pr HHH Br 0 2 3 2 3 CF CF HOCF HH 0 CF CF HHH Br 1 Pr Pr 2 3 3 2 3 CF CF Pr HOCF HH 1 CF CF Pr HHH Br 2 2 3 3 2 3 CF CF HOCF HH 2 CF CF HHH I 0 Pr Pr 2 3 3 2 3 CF CF Pr HNO HH 0 CF CF Pr HHH I 1 2 3 2 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Pr HHH I 2 CF CF Pr HClH I 0 2 3 2 3 CF CF HHH Me 0 CF CF HClH I 1 Pr Pr 2 3 2 3 CF CF Pr HHH Me 1 CF CF Pr HClH I 2 2 3 2 3 CF CF HHH Me 2 CF CF HBrH F 0 Pr Pr 2 3 2 3 CF CF Pr HHH CF 0 CF CF Pr HBrH F 1 2 3 3 2 3 CF CF Pr HHH CF 1 CF CF Pr HBrH F 2 2 3 3 2 3 CF CF Pr HHH CF 2 CF CF Pr HBrH Cl 0 2 3 3 2 3 CF CF Pr HHH CF CF 0 CF CF Pr HBrH Cl 1 2 3 2 3 2 3 CF CF HHH CF CF 1 CF CF HBrH Cl 2 Pr Pr 2 3 2 3 2 3 CF CF Pr HHH CF CF 2 CF CF Pr HBrH I 0 2 3 2 3 2 3 CF CF H H H CF(CF ) 0 CF CF HBrH I 1 Pr Pr 2 3 3 2 2 3 CF CF Pr H H H CF(CF ) 1 CF CF Pr HBrH I 2 2 3 3 2 2 3 CF CF H H H CF(CF ) 2 CF CF HIH F 0 Pr Pr 2 3 3 2 2 3 CF CF Pr HHH SMe 0 CF CF Pr HIH F 1 2 3 2 3 CF CF HHH SMe 1 CF CF HIH F 2 Pr Pr 2 3 2 3 CF CF Pr HHH SMe 2 CF CF Pr HIH Cl 0 2 3 2 3 CF CF Pr HHH SOMe 0 CF CF Pr HIH Cl 1 2 3 2 3 CF CF HHH SOMe 1 CF CF HIH Cl 2 Pr Pr 2 3 2 3 CF CF Pr HHH SOMe 2 CF CF Pr HIH Br 0 2 3 2 3 CF CF HHH SO Me 0 CF CF HIH Br 1 Pr Pr 2 3 2 2 3 CF CF Pr HHH SO Me 1 CF CF Pr HIH Br 2 2 3 2 2 3 CF CF HHH SO Me 2 CF CF HFH CN 0 Pr Pr 2 3 2 2 3 CF CF Pr HHH OMe 0 CF CF Pr HFH CN 1 2 3 2 3 CF CF Pr HHH OMe 1 CF CF Pr HFH CN 2 2 3 2 3 CF CF Pr HHH OMe 2 CF CF Pr HClH CN 0 2 3 2 3 CF CF Pr HHH OCF 0 CF CF Pr HClH CN 1 2 3 3 2 3 CF CF HHH OCF 1 CF CF HClH CN 2 Pr Pr 2 3 3 2 3 CF CF Pr HHH OCF 2 CF CF Pr HBrH CN 0 2 3 3 2 3 CF CF HHH NO 0 CF CF HBrH CN 1 Pr Pr 2 3 2 2 3 CF CF Pr HHH NO 1 CF CF Pr HBrH CN 2 2 3 2 2 3 CF CF HHH NO 2 CF CF HIH CN 0 Pr Pr 2 3 2 2 3 CF CF Pr HHH CN 0 CF CF Pr HIH CN 1 2 3 2 3 CF CF Pr HHH CN 1 CF CF Pr HIH CN 2 2 3 2 3 CF CF Pr HHH CN 2 CF CF Pr HCF HF 0 2 3 2 3 3 CF CF Pr HFH F 0 CF CF Pr HCF HF 1 2 3 2 3 3 CF CF HFH F 1 CF CF HCF HF 2 Pr Pr 2 3 2 3 3 CF CF Pr HFH F 2 CF CF Pr HCF HCl 0 2 3 2 3 3 CF CF HClH Cl 0 CF CF HCF HCl 1 Pr Pr 2 3 2 3 3 CF CF Pr HClH Cl 1 CF CF Pr HCF HCl 2 2 3 2 3 3 CF CF HClH Cl 2 CF CF HCF HBr 0 Pr Pr 2 3 2 3 3 CF CF Pr HBrH Br 0 CF CF Pr HCF HBr 1 2 3 2 3 3 CF CF HBrH Br 1 CF CF HCF HBr 2 Pr Pr 2 3 2 3 3 CF CF Pr HBrH Br 2 CF CF Pr HCF HI 0 2 3 2 3 3 CF CF Pr HIH I 0 CF CF Pr HCF HI 1 2 3 2 3 3 CF CF HIH I 1 CF CF HCF HI 2 Pr Pr 2 3 2 3 3 CF CF Pr HIH I 2 CF CF Pr HCF HCN 0 2 3 2 3 3 CF CF HFH Cl 0 CF CF HCF HCN 1 Pr Pr 2 3 2 3 3 CF CF Pr HFH Cl 1 CF CF Pr HCF HCN 2 2 3 2 3 3 CF CF HFH Cl 2 CF CF HFF H 0 Pr Pr 2 3 2 3 CF CF Pr HFH Br 0 CF CF Pr HFF H 1 2 3 2 3 CF CF Pr HFH Br 1 CF CF Pr HFF H 2 2 3 2 3 CF CF Pr HFH Br 2 CF CF Pr HCl Cl H 0 2 3 2 3 CF CF Pr HFH I 0 CF CF Pr HCl Cl H 1 2 3 2 3 CF CF HFH I 1 CF CF HCl Cl H 2 Pr Pr 2 3 2 3 CF CF Pr HFH I 2 CF CF Pr HBr Br H 0 2 3 2 3 CF CF HClH F 0 CF CF HBr Br H 1 Pr Pr 2 3 2 3 CF CF Pr HClH F 1 CF CF Pr HBr Br H 2 2 3 2 3 CF CF HClH F 2 CF CF HII H 0 Pr Pr 2 3 2 3 CF CF Pr HClH Br 0 CF CF Pr HII H 1 2 3 2 3 CF CF HClH Br 1 CF CF HII H 2 Pr Pr 2 3 2 3 CF CF Pr HClH Br 2 CF CF Pr HF Cl H 0 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF Pr HF Cl H 1 CF CF CH CF HHH H 0 2 3 2 3 2 3 CF CF HF Cl H 2 CF CF CH CF HHH H 1 2 3 2 3 2 3 CF CF Pr HF Br H 0 CF CF CH CF HHH H 2 2 3 2 3 2 3 CF CF HF Br H 1 CF CF CH CF FHH H 0 2 3 2 3 2 3 CF CF Pr HF Br H 2 CF CF CH CF FHH H 1 2 3 2 3 2 3 CF CF HFI H 0 CF CF CH CF FHH H 2 2 3 2 3 2 3 CF CF Pr HFI H 1 CF CF CH CF Cl H H H 0 2 3 2 3 2 3 CF CF Pr HFI H 2 CF CF CH CF Cl H H H 1 2 3 2 3 2 3 CF CF Pr HClF H 0 CF CF CH CF Cl H H H 2 2 3 2 3 2 3 CF CF Pr HClF H 1 CF CF CH CF Br H H H 0 2 3 2 3 2 3 CF CF HClF H 2 CF CF CH CF Br H H H 1 2 3 2 3 2 3 CF CF Pr HCl Br H 0 CF CF CH CF Br H H H 2 2 3 2 3 2 3 CF CF HCl Br H 1 CF CF CH CF IHH H 0 2 3 2 3 2 3 CF CF Pr HCl Br H 2 CF CF CH CF IHH H 1 2 3 2 3 2 3 CF CF HClI H 0 CF CF CH CF IHH H 2 2 3 2 3 2 3 CF CF Pr HClI H 1 CF CF CH CF Me H H H 0 2 3 2 3 2 3 CF CF Pr HClI H 2 CF CF CH CF Me H H H 1 2 3 2 3 2 3 CF CF Pr HBrF H 0 CF CF CH CF Me H H H 2 2 3 2 3 2 3 CF CF Pr HBrF H 1 CF CF CH CF CF HH H 0 2 3 2 3 2 3 3 CF CF HBrF H 2 CF CF CH CF CF HH H 1 2 3 2 3 2 3 3 CF CF Pr HBr Cl H 0 CF CF CH CF CF HH H 2 2 3 2 3 2 3 3 CF CF HBr Cl H 1 CF CF CH CF HFH H 0 2 3 2 3 2 3 CF CF Pr HBr Cl H 2 CF CF CH CF HFH H 1 2 3 2 3 2 3 CF CF HBrI H 0 CF CF CH CF HFH H 2 2 3 2 3 2 3 CF CF Pr HBrI H 1 CF CF CH CF HClH H 0 2 3 2 3 2 3 CF CF HBrI H 2 CF CF CH CF HClH H 1 2 3 2 3 2 3 CF CF Pr HIF H 0 CF CF CH CF HClH H 2 2 3 2 3 2 3 CF CF Pr HIF H 1 CF CF CH CF HBrH H 0 2 3 2 3 2 3 CF CF Pr HIF H 2 CF CF CH CF HBrH H 1 2 3 2 3 2 3 CF CF Pr HI Cl H 0 CF CF CH CF HBrH H 2 2 3 2 3 2 3 CF CF HI Cl H 1 CF CF CH CF HIH H 0 2 3 2 3 2 3 CF CF Pr HI Cl H 2 CF CF CH CF HIH H 1 2 3 2 3 2 3 CF CF HI Br H 0 CF CF CH CF HIH H 2 2 3 2 3 2 3 CF CF Pr HI Br H 1 CF CF CH CF HMeH H 0 2 3 2 3 2 3 CF CF HI Br H 2 CF CF CH CF HMeH H 1 2 3 2 3 2 3 CF CF Pr HF CN H 0 CF CF CH CF HMeH H 2 2 3 2 3 2 3 CF CF Pr HF CN H 1 CF CF CH CF HCF HH 0 2 3 2 3 2 3 3 CF CF Pr HF CN H 2 CF CF CH CF HCF HH 1 2 3 2 3 2 3 3 CF CF Pr HCl CN H 0 CF CF CH CF HCF HH 2 2 3 2 3 2 3 3 CF CF HCl CN H 1 CF CF CH CF HCF CF HH 0 2 3 2 3 2 3 2 3 CF CF Pr HCl CN H 2 CF CF CH CF HCF CF HH 1 2 3 2 3 2 3 2 3 CF CF HBr CN H 0 CF CF CH CF HCF CF HH 2 2 3 2 3 2 3 2 3 CF CF Pr HBr CN H 1 CF CF CH CF H CF(CF ) HH 0 2 3 2 3 2 3 3 2 CF CF HBr CN H 2 CF CF CH CF H CF(CF ) HH 1 2 3 2 3 2 3 3 2 CF CF Pr HI CN H 0 CF CF CH CF H CF(CF ) HH 2 2 3 2 3 2 3 3 2 CF CF HI CN H 1 CF CF CH CF H SMe H H 0 2 3 2 3 2 3 CF CF Pr HI CN H 2 CF CF CH CF H SMe H H 1 2 3 2 3 2 3 CF CF HCF FH 0 CF CF CH CF H SMe H H 2 2 3 3 2 3 2 3 CF CF Pr HCF FH 1 CF CF CH CF HSOMeH H 0 2 3 3 2 3 2 3 CF CF Pr HCF FH 2 CF CF CH CF HSOMeH H 1 2 3 3 2 3 2 3 CF CF HCF Cl H 0 CF CF CH CF HSOMeH H 2 2 3 3 2 3 2 3 CF CF Pr HCF Cl H 1 CF CF CH CF HSO Me H H 0 2 3 3 2 3 2 3 2 CF CF HCF Cl H 2 CF CF CH CF HSO Me H H 1 2 3 3 2 3 2 3 2 CF CF Pr HCF Br H 0 CF CF CH CF HSO Me H H 2 2 3 3 2 3 2 3 2 CF CF HCF Br H 1 CF CF CH CF H OMe H H 0 2 3 3 2 3 2 3 CF CF Pr HCF Br H 2 CF CF CH CF H OMe H H 1 2 3 3 2 3 2 3 CF CF Pr HCF IH 0 CF CF CH CF H OMe H H 2 2 3 3 2 3 2 3 CF CF Pr HCF IH 1 CF CF CH CF HOCF HH 0 2 3 3 2 3 2 3 3 CF CF Pr HCF IH 2 CF CF CH CF HOCF HH 1 2 3 3 2 3 2 3 3 CF CF Pr HCF CN H 0 CF CF CH CF HOCF HH 2 2 3 3 2 3 2 3 3 CF CF Pr HCF CN H 1 CF CF CH CF HNO HH 0 2 3 3 2 3 2 3 2 CF CF HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF CH CF HNO HH 1 CF CF CH CF HHH I 2 2 3 2 3 2 2 3 2 3 CF CF CH CF HNO HH 2 CF CF CH CF HHH Me 0 2 3 2 3 2 2 3 2 3 CF CF CH CF HCNH H 0 CF CF CH CF HHH Me 1 2 3 2 3 2 3 2 3 CF CF CH CF HCNH H 1 CF CF CH CF HHH Me 2 2 3 2 3 2 3 2 3 CF CF CH CF HCNH H 2 CF CF CH CF HHH CF 0 2 3 2 3 2 3 2 3 3 CF CF CH CF HHF H 0 CF CF CH CF HHH CF 1 2 3 2 3 2 3 2 3 3 CF CF CH CF HHF H 1 CF CF CH CF HHH CF 2 2 3 2 3 2 3 2 3 3 CF CF CH CF HHF H 2 CF CF CH CF HHH CF CF 0 2 3 2 3 2 3 2 3 2 3 CF CF CH CF HH Cl H 0 CF CF CH CF HHH CF CF 1 2 3 2 3 2 3 2 3 2 3 CF CF CH CF HH Cl H 1 CF CF CH CF HHH CF CF 2 2 3 2 3 2 3 2 3 2 3 CF CF CH CF HH Cl H 2 CF CF CH CF H H H CF(CF ) 0 2 3 2 3 2 3 2 3 3 2 CF CF CH CF HH Br H 0 CF CF CH CF H H H CF(CF ) 1 2 3 2 3 2 3 2 3 3 2 CF CF CH CF HH Br H 1 CF CF CH CF H H H CF(CF ) 2 2 3 2 3 2 3 2 3 3 2 CF CF CH CF HH Br H 2 CF CF CH CF HHH SMe 0 2 3 2 3 2 3 2 3 CF CF CH CF HHI H 0 CF CF CH CF HHH SMe 1 2 3 2 3 2 3 2 3 CF CF CH CF HHI H 1 CF CF CH CF HHH SMe 2 2 3 2 3 2 3 2 3 CF CF CH CF HHI H 2 CF CF CH CF HHH SOMe 0 2 3 2 3 2 3 2 3 CF CF CH CF HH Me H 0 CF CF CH CF HHH SOMe 1 2 3 2 3 2 3 2 3 CF CF CH CF HH Me H 1 CF CF CH CF HHH SOMe 2 2 3 2 3 2 3 2 3 CF CF CH CF HH Me H 2 CF CF CH CF HHH SO Me 0 2 3 2 3 2 3 2 3 2 CF CF CH CF HH CF H 0 CF CF CH CF HHH SO Me 1 2 3 2 3 3 2 3 2 3 2 CF CF CH CF HH CF H 1 CF CF CH CF HHH SO Me 2 2 3 2 3 3 2 3 2 3 2 CF CF CH CF HH CF H 2 CF CF CH CF HHH OMe 0 2 3 2 3 3 2 3 2 3 CF CF CH CF HH CF CF H 0 CF CF CH CF HHH OMe 1 2 3 2 3 2 3 2 3 2 3 CF CF CH CF HH CF CF H 1 CF CF CH CF HHH OMe 2 2 3 2 3 2 3 2 3 2 3 CF CF CH CF HH CF CF H 2 CF CF CH CF HHH OCF 0 2 3 2 3 2 3 2 3 2 3 3 CF CF CH CF H H CF(CF ) H 0 CF CF CH CF HHH OCF 1 2 3 2 3 3 2 2 3 2 3 3 CF CF CH CF H H CF(CF ) H 1 CF CF CH CF HHH OCF 2 2 3 2 3 3 2 2 3 2 3 3 CF CF CH CF H H CF(CF ) H 2 CF CF CH CF HHH NO 0 2 3 2 3 3 2 2 3 2 3 2 CF CF CH CF HH SMe H 0 CF CF CH CF HHH NO 1 2 3 2 3 2 3 2 3 2 CF CF CH CF HH SMe H 1 CF CF CH CF HHH NO 2 2 3 2 3 2 3 2 3 2 CF CF CH CF HH SMe H 2 CF CF CH CF HHH CN 0 2 3 2 3 2 3 2 3 CF CF CH CF H H SOMe H 0 CF CF CH CF HHH CN 1 2 3 2 3 2 3 2 3 CF CF CH CF H H SOMe H 1 CF CF CH CF HHH CN 2 2 3 2 3 2 3 2 3 CF CF CH CF H H SOMe H 2 CF CF CH CF HFH F 0 2 3 2 3 2 3 2 3 CF CF CH CF HH SO Me H 0 CF CF CH CF HFH F 1 2 3 2 3 2 2 3 2 3 CF CF CH CF HH SO Me H 1 CF CF CH CF HFH F 2 2 3 2 3 2 2 3 2 3 CF CF CH CF HH SO Me H 2 CF CF CH CF HClH Cl 0 2 3 2 3 2 2 3 2 3 CF CF CH CF HH OMe H 0 CF CF CH CF HClH Cl 1 2 3 2 3 2 3 2 3 CF CF CH CF HH OMe H 1 CF CF CH CF HClH Cl 2 2 3 2 3 2 3 2 3 CF CF CH CF HH OMe H 2 CF CF CH CF HBrH Br 0 2 3 2 3 2 3 2 3 CF CF CH CF H H OCF H 0 CF CF CH CF HBrH Br 1 2 3 2 3 3 2 3 2 3 CF CF CH CF H H OCF H 1 CF CF CH CF HBrH Br 2 2 3 2 3 3 2 3 2 3 CF CF CH CF H H OCF H 2 CF CF CH CF HIH I 0 2 3 2 3 3 2 3 2 3 CF CF CH CF HH NO H 0 CF CF CH CF HIH I 1 2 3 2 3 2 2 3 2 3 CF CF CH CF HH NO H 1 CF CF CH CF HIH I 2 2 3 2 3 2 2 3 2 3 CF CF CH CF HH NO H 2 CF CF CH CF HFH Cl 0 2 3 2 3 2 2 3 2 3 CF CF CH CF HH CN H 0 CF CF CH CF HFH Cl 1 2 3 2 3 2 3 2 3 CF CF CH CF HH CN H 1 CF CF CH CF HFH Cl 2 2 3 2 3 2 3 2 3 CF CF CH CF HH CN H 2 CF CF CH CF HFH Br 0 2 3 2 3 2 3 2 3 CF CF CH CF HHH F 0 CF CF CH CF HFH Br 1 2 3 2 3 2 3 2 3 CF CF CH CF HHH F 1 CF CF CH CF HFH Br 2 2 3 2 3 2 3 2 3 CF CF CH CF HHH F 2 CF CF CH CF HFH I 0 2 3 2 3 2 3 2 3 CF CF CH CF HHH Cl 0 CF CF CH CF HFH I 1 2 3 2 3 2 3 2 3 CF CF CH CF HHH Cl 1 CF CF CH CF HFH I 2 2 3 2 3 2 3 2 3 CF CF CH CF HHH Cl 2 CF CF CH CF HClH F 0 2 3 2 3 2 3 2 3 CF CF CH CF HHH Br 0 CF CF CH CF HClH F 1 2 3 2 3 2 3 2 3 CF CF CH CF HHH Br 1 CF CF CH CF HClH F 2 2 3 2 3 2 3 2 3 CF CF CH CF HHH Br 2 CF CF CH CF HClH Br 0 2 3 2 3 2 3 2 3 CF CF CH CF HHH I 0 CF CF CH CF HClH Br 1 2 3 2 3 2 3 2 3 CF CF CH CF HHH I 1 CF CF CH CF HClH Br 2 2 3 2 3 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n CF CF CH CF HClH I 0 CF CF CH CF HF Cl H 1 2 3 2 3 2 3 2 3 CF CF CH CF HClH I 1 CF CF CH CF HF Cl H 2 2 3 2 3 2 3 2 3 CF CF CH CF HClH I 2 CF CF CH CF HF Br H 0 2 3 2 3 2 3 2 3 CF CF CH CF HBrH F 0 CF CF CH CF HF Br H 1 2 3 2 3 2 3 2 3 CF CF CH CF HBrH F 1 CF CF CH CF HF Br H 2 2 3 2 3 2 3 2 3 CF CF CH CF HBrH F 2 CF CF CH CF HFI H 0 2 3 2 3 2 3 2 3 CF CF CH CF HBrH Cl 0 CF CF CH CF HFI H 1 2 3 2 3 2 3 2 3 CF CF CH CF HBrH Cl 1 CF CF CH CF HFI H 2 2 3 2 3 2 3 2 3 CF CF CH CF HBrH Cl 2 CF CF CH CF HClF H 0 2 3 2 3 2 3 2 3 CF CF CH CF HBrH I 0 CF CF CH CF HClF H 1 2 3 2 3 2 3 2 3 CF CF CH CF HBrH I 1 CF CF CH CF HClF H 2 2 3 2 3 2 3 2 3 CF CF CH CF HBrH I 2 CF CF CH CF HCl Br H 0 2 3 2 3 2 3 2 3 CF CF CH CF HIH F 0 CF CF CH CF HCl Br H 1 2 3 2 3 2 3 2 3 CF CF CH CF HIH F 1 CF CF CH CF HCl Br H 2 2 3 2 3 2 3 2 3 CF CF CH CF HIH F 2 CF CF CH CF HClI H 0 2 3 2 3 2 3 2 3 CF CF CH CF HIH Cl 0 CF CF CH CF HClI H 1 2 3 2 3 2 3 2 3 CF CF CH CF HIH Cl 1 CF CF CH CF HClI H 2 2 3 2 3 2 3 2 3 CF CF CH CF HIH Cl 2 CF CF CH CF HBrF H 0 2 3 2 3 2 3 2 3 CF CF CH CF HIH Br 0 CF CF CH CF HBrF H 1 2 3 2 3 2 3 2 3 CF CF CH CF HIH Br 1 CF CF CH CF HBrF H 2 2 3 2 3 2 3 2 3 CF CF CH CF HIH Br 2 CF CF CH CF HBr Cl H 0 2 3 2 3 2 3 2 3 CF CF CH CF HFH CN 0 CF CF CH CF HBr Cl H 1 2 3 2 3 2 3 2 3 CF CF CH CF HFH CN 1 CF CF CH CF HBr Cl H 2 2 3 2 3 2 3 2 3 CF CF CH CF HFH CN 2 CF CF CH CF HBrI H 0 2 3 2 3 2 3 2 3 CF CF CH CF HClH CN 0 CF CF CH CF HBrI H 1 2 3 2 3 2 3 2 3 CF CF CH CF HClH CN 1 CF CF CH CF HBrI H 2 2 3 2 3 2 3 2 3 CF CF CH CF HClH CN 2 CF CF CH CF HIF H 0 2 3 2 3 2 3 2 3 CF CF CH CF HBrH CN 0 CF CF CH CF HIF H 1 2 3 2 3 2 3 2 3 CF CF CH CF HBrH CN 1 CF CF CH CF HIF H 2 2 3 2 3 2 3 2 3 CF CF CH CF HBrH CN 2 CF CF CH CF HI Cl H 0 2 3 2 3 2 3 2 3 CF CF CH CF HIH CN 0 CF CF CH CF HI Cl H 1 2 3 2 3 2 3 2 3 CF CF CH CF HIH CN 1 CF CF CH CF HI Cl H 2 2 3 2 3 2 3 2 3 CF CF CH CF HIH CN 2 CF CF CH CF HI Br H 0 2 3 2 3 2 3 2 3 CF CF CH CF HCF HF 0 CF CF CH CF HI Br H 1 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HF 1 CF CF CH CF HI Br H 2 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HF 2 CF CF CH CF HF CN H 0 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HCl 0 CF CF CH CF HF CN H 1 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HCl 1 CF CF CH CF HF CN H 2 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HCl 2 CF CF CH CF HCl CN H 0 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HBr 0 CF CF CH CF HCl CN H 1 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HBr 1 CF CF CH CF HCl CN H 2 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HBr 2 CF CF CH CF HBr CN H 0 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HI 0 CF CF CH CF HBr CN H 1 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HI 1 CF CF CH CF HBr CN H 2 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HI 2 CF CF CH CF HI CN H 0 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HCN 0 CF CF CH CF HI CN H 1 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HCN 1 CF CF CH CF HI CN H 2 2 3 2 3 3 2 3 2 3 CF CF CH CF HCF HCN 2 CF CF CH CF HCF FH 0 2 3 2 3 3 2 3 2 3 3 CF CF CH CF HFF H 0 CF CF CH CF HCF FH 1 2 3 2 3 2 3 2 3 3 CF CF CH CF HFF H 1 CF CF CH CF HCF FH 2 2 3 2 3 2 3 2 3 3 CF CF CH CF HFF H 2 CF CF CH CF HCF Cl H 0 2 3 2 3 2 3 2 3 3 CF CF CH CF HCl Cl H 0 CF CF CH CF HCF Cl H 1 2 3 2 3 2 3 2 3 3 CF CF CH CF HCl Cl H 1 CF CF CH CF HCF Cl H 2 2 3 2 3 2 3 2 3 3 CF CF CH CF HCl Cl H 2 CF CF CH CF HCF Br H 0 2 3 2 3 2 3 2 3 3 CF CF CH CF HBr Br H 0 CF CF CH CF HCF Br H 1 2 3 2 3 2 3 2 3 3 CF CF CH CF HBr Br H 1 CF CF CH CF HCF Br H 2 2 3 2 3 2 3 2 3 3 CF CF CH CF HBr Br H 2 CF CF CH CF HCF IH 0 2 3 2 3 2 3 2 3 3 CF CF CH CF HII H 0 CF CF CH CF HCF IH 1 2 3 2 3 2 3 2 3 3 CF CF CH CF HII H 1 CF CF CH CF HCF IH 2 2 3 2 3 2 3 2 3 3 CF CF CH CF HII H 2 CF CF CH CF HCF CN H 0 2 3 2 3 2 3 2 3 3 CF CF CH CF HF Cl H 0 CF CF CH CF HCF CN H 1 2 3 2 3 2 3 2 3 3 CF CF CH CF HCF CN H 2 2 3 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Me HHH H 0 SCF Me HNO HH 1 3 3 2 SCF Me HHH H 1 SCF Me HNO HH 2 3 3 2 SCF Me HHH H 2 SCF Me HCNH H 0 SCF Me FHH H 0 SCF Me HCNH H 1 SCF Me FHH H 1 SCF Me HCNH H 2 SCF Me FHH H 2 SCF Me HHF H 0 SCF Me Cl H H H 0 SCF Me HHF H 1 SCF Me Cl H H H 1 SCF Me HHF H 2 SCF Me Cl H H H 2 SCF Me HH Cl H 0 SCF Me Br H H H 0 SCF Me HH Cl H 1 SCF Me Br H H H 1 SCF Me HH Cl H 2 SCF Me Br H H H 2 SCF Me HH Br H 0 SCF Me IHH H 0 SCF Me HH Br H 1 SCF Me IHH H 1 SCF Me HH Br H 2 SCF Me IHH H 2 SCF Me HHI H 0 SCF Me Me H H H 0 SCF Me HHI H 1 SCF Me Me H H H 1 SCF Me HHI H 2 SCF Me Me H H H 2 SCF Me HH Me H 0 SCF Me CF HH H 0 SCF Me HH Me H 1 3 3 3 SCF Me CF HH H 1 SCF Me HH Me H 2 3 3 3 SCF Me CF HH H 2 SCF Me HH CF H 0 3 3 3 3 SCF Me HFH H 0 SCF Me HH CF H 1 3 3 3 SCF Me HFH H 1 SCF Me HH CF H 2 3 3 3 SCF Me HFH H 2 SCF Me HH CF CF H 0 3 3 2 3 SCF Me HClH H 0 SCF Me HH CF CF H 1 3 3 2 3 SCF Me HClH H 1 SCF Me HH CF CF H 2 3 3 2 3 SCF Me HClH H 2 SCF Me H H CF(CF ) H 0 3 3 3 2 SCF Me HBrH H 0 SCF Me H H CF(CF ) H 1 3 3 3 2 SCF Me HBrH H 1 SCF Me H H CF(CF ) H 2 3 3 3 2 SCF Me HBrH H 2 SCF Me HH SMe H 0 SCF Me HIH H 0 SCF Me HH SMe H 1 SCF Me HIH H 1 SCF Me HH SMe H 2 SCF Me HIH H 2 SCF Me H H SOMe H 0 SCF Me HMeH H 0 SCF Me H H SOMe H 1 SCF Me HMeH H 1 SCF Me H H SOMe H 2 SCF Me HMeH H 2 SCF Me HH SO Me H 0 3 3 2 SCF Me HCF HH 0 SCF Me HH SO Me H 1 3 3 3 2 SCF Me HCF HH 1 SCF Me HH SO Me H 2 3 3 3 2 SCF Me HCF HH 2 SCF Me HH OMe H 0 3 3 3 SCF Me HCF CF HH 0 SCF Me HH OMe H 1 3 2 3 3 SCF Me HCF CF HH 1 SCF Me HH OMe H 2 3 2 3 3 SCF Me HCF CF HH 2 SCF Me H H OCF H 0 3 2 3 3 3 SCF Me H CF(CF ) HH 0 SCF Me H H OCF H 1 3 3 2 3 3 SCF Me H CF(CF ) HH 1 SCF Me H H OCF H 2 3 3 2 3 3 SCF Me H CF(CF ) HH 2 SCF Me HH NO H 0 3 3 2 3 2 SCF Me H SMe H H 0 SCF Me HH NO H 1 3 3 2 SCF Me H SMe H H 1 SCF Me HH NO H 2 3 3 2 SCF Me H SMe H H 2 SCF Me HH CN H 0 SCF Me HSOMeH H 0 SCF Me HH CN H 1 SCF Me HSOMeH H 1 SCF Me HH CN H 2 SCF Me HSOMeH H 2 SCF Me HHH F 0 SCF Me HSO Me H H 0 SCF Me HHH F 1 3 2 3 SCF Me HSO Me H H 1 SCF Me HHH F 2 3 2 3 SCF Me HSO Me H H 2 SCF Me HHH Cl 0 3 2 3 SCF Me H OMe H H 0 SCF Me HHH Cl 1 SCF Me H OMe H H 1 SCF Me HHH Cl 2 SCF Me H OMe H H 2 SCF Me HHH Br 0 SCF Me HOCF HH 0 SCF Me HHH Br 1 3 3 3 SCF Me HOCF HH 1 SCF Me HHH Br 2 3 3 3 SCF Me HOCF HH 2 SCF Me HHH I 0 3 3 3 SCF Me HNO HH 0 SCF Me HHH I 1 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Me HHH I 2 SCF Me HClH I 0 SCF Me HHH Me 0 SCF Me HClH I 1 SCF Me HHH Me 1 SCF Me HClH I 2 SCF Me HHH Me 2 SCF Me HBrH F 0 SCF Me HHH CF 0 SCF Me HBrH F 1 3 3 3 SCF Me HHH CF 1 SCF Me HBrH F 2 3 3 3 SCF Me HHH CF 2 SCF Me HBrH Cl 0 3 3 3 SCF Me HHH CF CF 0 SCF Me HBrH Cl 1 3 2 3 3 SCF Me HHH CF CF 1 SCF Me HBrH Cl 2 3 2 3 3 SCF Me HHH CF CF 2 SCF Me HBrH I 0 3 2 3 3 SCF Me H H H CF(CF ) 0 SCF Me HBrH I 1 3 3 2 3 SCF Me H H H CF(CF ) 1 SCF Me HBrH I 2 3 3 2 3 SCF Me H H H CF(CF ) 2 SCF Me HIH F 0 3 3 2 3 SCF Me HHH SMe 0 SCF Me HIH F 1 SCF Me HHH SMe 1 SCF Me HIH F 2 SCF Me HHH SMe 2 SCF Me HIH Cl 0 SCF Me HHH SOMe 0 SCF Me HIH Cl 1 SCF Me HHH SOMe 1 SCF Me HIH Cl 2 SCF Me HHH SOMe 2 SCF Me HIH Br 0 SCF Me HHH SO Me 0 SCF Me HIH Br 1 3 2 3 SCF Me HHH SO Me 1 SCF Me HIH Br 2 3 2 3 SCF Me HHH SO Me 2 SCF Me HFH CN 0 3 2 3 SCF Me HHH OMe 0 SCF Me HFH CN 1 SCF Me HHH OMe 1 SCF Me HFH CN 2 SCF Me HHH OMe 2 SCF Me HClH CN 0 SCF Me HHH OCF 0 SCF Me HClH CN 1 3 3 3 SCF Me HHH OCF 1 SCF Me HClH CN 2 3 3 3 SCF Me HHH OCF 2 SCF Me HBrH CN 0 3 3 3 SCF Me HHH NO 0 SCF Me HBrH CN 1 3 2 3 SCF Me HHH NO 1 SCF Me HBrH CN 2 3 2 3 SCF Me HHH NO 2 SCF Me HIH CN 0 3 2 3 SCF Me HHH CN 0 SCF Me HIH CN 1 SCF Me HHH CN 1 SCF Me HIH CN 2 SCF Me HHH CN 2 SCF Me HCF HF 0 3 3 3 SCF Me HFH F 0 SCF Me HCF HF 1 3 3 3 SCF Me HFH F 1 SCF Me HCF HF 2 3 3 3 SCF Me HFH F 2 SCF Me HCF HCl 0 3 3 3 SCF Me HClH Cl 0 SCF Me HCF HCl 1 3 3 3 SCF Me HClH Cl 1 SCF Me HCF HCl 2 3 3 3 SCF Me HClH Cl 2 SCF Me HCF HBr 0 3 3 3 SCF Me HBrH Br 0 SCF Me HCF HBr 1 3 3 3 SCF Me HBrH Br 1 SCF Me HCF HBr 2 3 3 3 SCF Me HBrH Br 2 SCF Me HCF HI 0 3 3 3 SCF Me HIH I 0 SCF Me HCF HI 1 3 3 3 SCF Me HIH I 1 SCF Me HCF HI 2 3 3 3 SCF Me HIH I 2 SCF Me HCF HCN 0 3 3 3 SCF Me HFH Cl 0 SCF Me HCF HCN 1 3 3 3 SCF Me HFH Cl 1 SCF Me HCF HCN 2 3 3 3 SCF Me HFH Cl 2 SCF Me HFF H 0 SCF Me HFH Br 0 SCF Me HFF H 1 SCF Me HFH Br 1 SCF Me HFF H 2 SCF Me HFH Br 2 SCF Me HCl Cl H 0 SCF Me HFH I 0 SCF Me HCl Cl H 1 SCF Me HFH I 1 SCF Me HCl Cl H 2 SCF Me HFH I 2 SCF Me HBr Br H 0 SCF Me HClH F 0 SCF Me HBr Br H 1 SCF Me HClH F 1 SCF Me HBr Br H 2 SCF Me HClH F 2 SCF Me HII H 0 SCF Me HClH Br 0 SCF Me HII H 1 SCF Me HClH Br 1 SCF Me HII H 2 SCF Me HClH Br 2 SCF Me HF Cl H 0 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Me HF Cl H 1 SCF Et HHH H 0 SCF Me HF Cl H 2 SCF Et HHH H 1 SCF Me HF Br H 0 SCF Et HHH H 2 SCF Me HF Br H 1 SCF Et FHH H 0 SCF Me HF Br H 2 SCF Et FHH H 1 SCF Me HFI H 0 SCF Et FHH H 2 SCF Me HFI H 1 SCF Et Cl H H H 0 SCF Me HFI H 2 SCF Et Cl H H H 1 SCF Me HClF H 0 SCF Et Cl H H H 2 SCF Me HClF H 1 SCF Et Br H H H 0 SCF Me HClF H 2 SCF Et Br H H H 1 SCF Me HCl Br H 0 SCF Et Br H H H 2 SCF Me HCl Br H 1 SCF Et IHH H 0 SCF Me HCl Br H 2 SCF Et IHH H 1 SCF Me HClI H 0 SCF Et IHH H 2 SCF Me HClI H 1 SCF Et Me H H H 0 SCF Me HClI H 2 SCF Et Me H H H 1 SCF Me HBrF H 0 SCF Et Me H H H 2 SCF Me HBrF H 1 SCF Et CF HH H 0 3 3 3 SCF Me HBrF H 2 SCF Et CF HH H 1 3 3 3 SCF Me HBr Cl H 0 SCF Et CF HH H 2 3 3 3 SCF Me HBr Cl H 1 SCF Et HFH H 0 SCF Me HBr Cl H 2 SCF Et HFH H 1 SCF Me HBrI H 0 SCF Et HFH H 2 SCF Me HBrI H 1 SCF Et HClH H 0 SCF Me HBrI H 2 SCF Et HClH H 1 SCF Me HIF H 0 SCF Et HClH H 2 SCF Me HIF H 1 SCF Et HBrH H 0 SCF Me HIF H 2 SCF Et HBrH H 1 SCF Me HI Cl H 0 SCF Et HBrH H 2 SCF Me HI Cl H 1 SCF Et HIH H 0 SCF Me HI Cl H 2 SCF Et HIH H 1 SCF Me HI Br H 0 SCF Et HIH H 2 SCF Me HI Br H 1 SCF Et HMeH H 0 SCF Me HI Br H 2 SCF Et HMeH H 1 SCF Me HF CN H 0 SCF Et HMeH H 2 SCF Me HF CN H 1 SCF Et HCF HH 0 3 3 3 SCF Me HF CN H 2 SCF Et HCF HH 1 3 3 3 SCF Me HCl CN H 0 SCF Et HCF HH 2 3 3 3 SCF Me HCl CN H 1 SCF Et HCF CF HH 0 3 3 2 3 SCF Me HCl CN H 2 SCF Et HCF CF HH 1 3 3 2 3 SCF Me HBr CN H 0 SCF Et HCF CF HH 2 3 3 2 3 SCF Me HBr CN H 1 SCF Et H CF(CF ) HH 0 3 3 3 2 SCF Me HBr CN H 2 SCF Et H CF(CF ) HH 1 3 3 3 2 SCF Me HI CN H 0 SCF Et H CF(CF ) HH 2 3 3 3 2 SCF Me HI CN H 1 SCF Et H SMe H H 0 SCF Me HI CN H 2 SCF Et H SMe H H 1 SCF Me HCF FH 0 SCF Et H SMe H H 2 3 3 3 SCF Me HCF FH 1 SCF Et HSOMeH H 0 3 3 3 SCF Me HCF FH 2 SCF Et HSOMeH H 1 3 3 3 SCF Me HCF Cl H 0 SCF Et HSOMeH H 2 3 3 3 SCF Me HCF Cl H 1 SCF Et HSO Me H H 0 3 3 3 2 SCF Me HCF Cl H 2 SCF Et HSO Me H H 1 3 3 3 2 SCF Me HCF Br H 0 SCF Et HSO Me H H 2 3 3 3 2 SCF Me HCF Br H 1 SCF Et H OMe H H 0 3 3 3 SCF Me HCF Br H 2 SCF Et H OMe H H 1 3 3 3 SCF Me HCF IH 0 SCF Et H OMe H H 2 3 3 3 SCF Me HCF IH 1 SCF Et HOCF HH 0 3 3 3 3 SCF Me HCF IH 2 SCF Et HOCF HH 1 3 3 3 3 SCF Me HCF CN H 0 SCF Et HOCF HH 2 3 3 3 3 SCF Me HCF CN H 1 SCF Et HNO HH 0 3 3 3 2 SCF Me HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Et HNO HH 1 SCF Et HHH I 2 3 2 3 SCF Et HNO HH 2 SCF Et HHH Me 0 3 2 3 SCF Et HCNH H 0 SCF Et HHH Me 1 SCF Et HCNH H 1 SCF Et HHH Me 2 SCF Et HCNH H 2 SCF Et HHH CF 0 3 3 3 SCF Et HHF H 0 SCF Et HHH CF 1 3 3 3 SCF Et HHF H 1 SCF Et HHH CF 2 3 3 3 SCF Et HHF H 2 SCF Et HHH CF CF 0 3 3 2 3 SCF Et HH Cl H 0 SCF Et HHH CF CF 1 3 3 2 3 SCF Et HH Cl H 1 SCF Et HHH CF CF 2 3 3 2 3 SCF Et HH Cl H 2 SCF Et H H H CF(CF ) 0 3 3 3 2 SCF Et HH Br H 0 SCF Et H H H CF(CF ) 1 3 3 3 2 SCF Et HH Br H 1 SCF Et H H H CF(CF ) 2 3 3 3 2 SCF Et HH Br H 2 SCF Et HHH SMe 0 SCF Et HHI H 0 SCF Et HHH SMe 1 SCF Et HHI H 1 SCF Et HHH SMe 2 SCF Et HHI H 2 SCF Et HHH SOMe 0 SCF Et HH Me H 0 SCF Et HHH SOMe 1 SCF Et HH Me H 1 SCF Et HHH SOMe 2 SCF Et HH Me H 2 SCF Et HHH SO Me 0 3 3 2 SCF Et HH CF H 0 SCF Et HHH SO Me 1 3 3 3 2 SCF Et HH CF H 1 SCF Et HHH SO Me 2 3 3 3 2 SCF Et HH CF H 2 SCF Et HHH OMe 0 3 3 3 SCF Et HH CF CF H 0 SCF Et HHH OMe 1 3 2 3 3 SCF Et HH CF CF H 1 SCF Et HHH OMe 2 3 2 3 3 SCF Et HH CF CF H 2 SCF Et HHH OCF 0 3 2 3 3 3 SCF Et H H CF(CF ) H 0 SCF Et HHH OCF 1 3 3 2 3 3 SCF Et H H CF(CF ) H 1 SCF Et HHH OCF 2 3 3 2 3 3 SCF Et H H CF(CF ) H 2 SCF Et HHH NO 0 3 3 2 3 2 SCF Et HH SMe H 0 SCF Et HHH NO 1 3 3 2 SCF Et HH SMe H 1 SCF Et HHH NO 2 3 3 2 SCF Et HH SMe H 2 SCF Et HHH CN 0 SCF Et H H SOMe H 0 SCF Et HHH CN 1 SCF Et H H SOMe H 1 SCF Et HHH CN 2 SCF Et H H SOMe H 2 SCF Et HFH F 0 SCF Et HH SO Me H 0 SCF Et HFH F 1 3 2 3 SCF Et HH SO Me H 1 SCF Et HFH F 2 3 2 3 SCF Et HH SO Me H 2 SCF Et HClH Cl 0 3 2 3 SCF Et HH OMe H 0 SCF Et HClH Cl 1 SCF Et HH OMe H 1 SCF Et HClH Cl 2 SCF Et HH OMe H 2 SCF Et HBrH Br 0 SCF Et H H OCF H 0 SCF Et HBrH Br 1 3 3 3 SCF Et H H OCF H 1 SCF Et HBrH Br 2 3 3 3 SCF Et H H OCF H 2 SCF Et HIH I 0 3 3 3 SCF Et HH NO H 0 SCF Et HIH I 1 3 2 3 SCF Et HH NO H 1 SCF Et HIH I 2 3 2 3 SCF Et HH NO H 2 SCF Et HFH Cl 0 3 2 3 SCF Et HH CN H 0 SCF Et HFH Cl 1 SCF Et HH CN H 1 SCF Et HFH Cl 2 SCF Et HH CN H 2 SCF Et HFH Br 0 SCF Et HHH F 0 SCF Et HFH Br 1 SCF Et HHH F 1 SCF Et HFH Br 2 SCF Et HHH F 2 SCF Et HFH I 0 SCF Et HHH Cl 0 SCF Et HFH I 1 SCF Et HHH Cl 1 SCF Et HFH I 2 SCF Et HHH Cl 2 SCF Et HClH F 0 SCF Et HHH Br 0 SCF Et HClH F 1 SCF Et HHH Br 1 SCF Et HClH F 2 SCF Et HHH Br 2 SCF Et HClH Br 0 SCF Et HHH I 0 SCF Et HClH Br 1 SCF Et HHH I 1 SCF Et HClH Br 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Et HClH I 0 SCF Et HF Cl H 1 SCF Et HClH I 1 SCF Et HF Cl H 2 SCF Et HClH I 2 SCF Et HF Br H 0 SCF Et HBrH F 0 SCF Et HF Br H 1 SCF Et HBrH F 1 SCF Et HF Br H 2 SCF Et HBrH F 2 SCF Et HFI H 0 SCF Et HBrH Cl 0 SCF Et HFI H 1 SCF Et HBrH Cl 1 SCF Et HFI H 2 SCF Et HBrH Cl 2 SCF Et HClF H 0 SCF Et HBrH I 0 SCF Et HClF H 1 SCF Et HBrH I 1 SCF Et HClF H 2 SCF Et HBrH I 2 SCF Et HCl Br H 0 SCF Et HIH F 0 SCF Et HCl Br H 1 SCF Et HIH F 1 SCF Et HCl Br H 2 SCF Et HIH F 2 SCF Et HClI H 0 SCF Et HIH Cl 0 SCF Et HClI H 1 SCF Et HIH Cl 1 SCF Et HClI H 2 SCF Et HIH Cl 2 SCF Et HBrF H 0 SCF Et HIH Br 0 SCF Et HBrF H 1 SCF Et HIH Br 1 SCF Et HBrF H 2 SCF Et HIH Br 2 SCF Et HBr Cl H 0 SCF Et HFH CN 0 SCF Et HBr Cl H 1 SCF Et HFH CN 1 SCF Et HBr Cl H 2 SCF Et HFH CN 2 SCF Et HBrI H 0 SCF Et HClH CN 0 SCF Et HBrI H 1 SCF Et HClH CN 1 SCF Et HBrI H 2 SCF Et HClH CN 2 SCF Et HIF H 0 SCF Et HBrH CN 0 SCF Et HIF H 1 SCF Et HBrH CN 1 SCF Et HIF H 2 SCF Et HBrH CN 2 SCF Et HI Cl H 0 SCF Et HIH CN 0 SCF Et HI Cl H 1 SCF Et HIH CN 1 SCF Et HI Cl H 2 SCF Et HIH CN 2 SCF Et HI Br H 0 SCF Et HCF HF 0 SCF Et HI Br H 1 3 3 3 SCF Et HCF HF 1 SCF Et HI Br H 2 3 3 3 SCF Et HCF HF 2 SCF Et HF CN H 0 3 3 3 SCF Et HCF HCl 0 SCF Et HF CN H 1 3 3 3 SCF Et HCF HCl 1 SCF Et HF CN H 2 3 3 3 SCF Et HCF HCl 2 SCF Et HCl CN H 0 3 3 3 SCF Et HCF HBr 0 SCF Et HCl CN H 1 3 3 3 SCF Et HCF HBr 1 SCF Et HCl CN H 2 3 3 3 SCF Et HCF HBr 2 SCF Et HBr CN H 0 3 3 3 SCF Et HCF HI 0 SCF Et HBr CN H 1 3 3 3 SCF Et HCF HI 1 SCF Et HBr CN H 2 3 3 3 SCF Et HCF HI 2 SCF Et HI CN H 0 3 3 3 SCF Et HCF HCN 0 SCF Et HI CN H 1 3 3 3 SCF Et HCF HCN 1 SCF Et HI CN H 2 3 3 3 SCF Et HCF HCN 2 SCF Et HCF FH 0 3 3 3 3 SCF Et HFF H 0 SCF Et HCF FH 1 3 3 3 SCF Et HFF H 1 SCF Et HCF FH 2 3 3 3 SCF Et HFF H 2 SCF Et HCF Cl H 0 3 3 3 SCF Et HCl Cl H 0 SCF Et HCF Cl H 1 3 3 3 SCF Et HCl Cl H 1 SCF Et HCF Cl H 2 3 3 3 SCF Et HCl Cl H 2 SCF Et HCF Br H 0 3 3 3 SCF Et HBr Br H 0 SCF Et HCF Br H 1 3 3 3 SCF Et HBr Br H 1 SCF Et HCF Br H 2 3 3 3 SCF Et HBr Br H 2 SCF Et HCF IH 0 3 3 3 SCF Et HII H 0 SCF Et HCF IH 1 3 3 3 SCF Et HII H 1 SCF Et HCF IH 2 3 3 3 SCF Et HII H 2 SCF Et HCF CN H 0 3 3 3 SCF Et HF Cl H 0 SCF Et HCF CN H 1 3 3 3 SCF Et HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Pr HHH H 0 SCF Pr HNO HH 1 3 3 2 SCF HHH H 1 SCF HNO HH 2 Pr Pr 3 3 2 SCF Pr HHH H 2 SCF Pr HCNH H 0 SCF FHH H 0 SCF HCNH H 1 Pr Pr SCF Pr FHH H 1 SCF Pr HCNH H 2 SCF Pr FHH H 2 SCF Pr HHF H 0 SCF Pr Cl H H H 0 SCF Pr HHF H 1 SCF Pr Cl H H H 1 SCF Pr HHF H 2 SCF Cl H H H 2 SCF HH Cl H 0 Pr Pr SCF Pr Br H H H 0 SCF Pr HH Cl H 1 SCF Br H H H 1 SCF HH Cl H 2 Pr Pr SCF Pr Br H H H 2 SCF Pr HH Br H 0 SCF IHH H 0 SCF HH Br H 1 Pr Pr SCF Pr IHH H 1 SCF Pr HH Br H 2 SCF IHH H 2 SCF HHI H 0 Pr Pr SCF Pr Me H H H 0 SCF Pr HHI H 1 SCF Pr Me H H H 1 SCF Pr HHI H 2 SCF Me H H H 2 SCF HH Me H 0 Pr Pr SCF Pr CF HH H 0 SCF Pr HH Me H 1 3 3 3 SCF CF HH H 1 SCF HH Me H 2 Pr Pr 3 3 3 SCF Pr CF HH H 2 SCF Pr HH CF H 0 3 3 3 3 SCF HFH H 0 SCF HH CF H 1 Pr Pr 3 3 3 SCF Pr HFH H 1 SCF Pr HH CF H 2 3 3 3 SCF Pr HFH H 2 SCF Pr HH CF CF H 0 3 3 2 3 SCF Pr HClH H 0 SCF Pr HH CF CF H 1 3 3 2 3 SCF Pr HClH H 1 SCF Pr HH CF CF H 2 3 3 2 3 SCF HClH H 2 SCF H H CF(CF ) H 0 Pr Pr 3 3 3 2 SCF Pr HBrH H 0 SCF Pr H H CF(CF ) H 1 3 3 3 2 SCF HBrH H 1 SCF H H CF(CF ) H 2 Pr Pr 3 3 3 2 SCF Pr HBrH H 2 SCF Pr HH SMe H 0 SCF HIH H 0 SCF HH SMe H 1 Pr Pr SCF Pr HIH H 1 SCF Pr HH SMe H 2 SCF Pr HIH H 2 SCF Pr H H SOMe H 0 SCF Pr HMeH H 0 SCF Pr H H SOMe H 1 SCF Pr HMeH H 1 SCF Pr H H SOMe H 2 SCF HMeH H 2 SCF HH SO Me H 0 Pr Pr 3 3 2 SCF Pr HCF HH 0 SCF Pr HH SO Me H 1 3 3 3 2 SCF HCF HH 1 SCF HH SO Me H 2 Pr Pr 3 3 3 2 SCF Pr HCF HH 2 SCF Pr HH OMe H 0 3 3 3 SCF HCF CF HH 0 SCF HH OMe H 1 Pr Pr 3 2 3 3 SCF Pr HCF CF HH 1 SCF Pr HH OMe H 2 3 2 3 3 SCF HCF CF HH 2 SCF H H OCF H 0 Pr Pr 3 2 3 3 3 SCF Pr H CF(CF ) HH 0 SCF Pr H H OCF H 1 3 3 2 3 3 SCF Pr H CF(CF ) HH 1 SCF Pr H H OCF H 2 3 3 2 3 3 SCF H CF(CF ) HH 2 SCF HH NO H 0 Pr Pr 3 3 2 3 2 SCF Pr H SMe H H 0 SCF Pr HH NO H 1 3 3 2 SCF H SMe H H 1 SCF HH NO H 2 Pr Pr 3 3 2 SCF Pr H SMe H H 2 SCF Pr HH CN H 0 SCF HSOMeH H 0 SCF HH CN H 1 Pr Pr SCF Pr HSOMeH H 1 SCF Pr HH CN H 2 SCF Pr HSOMeH H 2 SCF Pr HHH F 0 SCF Pr HSO Me H H 0 SCF Pr HHH F 1 3 2 3 SCF Pr HSO Me H H 1 SCF Pr HHH F 2 3 2 3 SCF HSO Me H H 2 SCF HHH Cl 0 Pr Pr 3 2 3 SCF Pr H OMe H H 0 SCF Pr HHH Cl 1 SCF H OMe H H 1 SCF HHH Cl 2 Pr Pr SCF Pr H OMe H H 2 SCF Pr HHH Br 0 SCF HOCF HH 0 SCF HHH Br 1 Pr Pr 3 3 3 SCF Pr HOCF HH 1 SCF Pr HHH Br 2 3 3 3 SCF HOCF HH 2 SCF HHH I 0 Pr Pr 3 3 3 SCF Pr HNO HH 0 SCF Pr HHH I 1 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Pr HHH I 2 SCF Pr HClH I 0 SCF HHH Me 0 SCF HClH I 1 Pr Pr SCF Pr HHH Me 1 SCF Pr HClH I 2 SCF HHH Me 2 SCF HBrH F 0 Pr Pr SCF Pr HHH CF 0 SCF Pr HBrH F 1 3 3 3 SCF Pr HHH CF 1 SCF Pr HBrH F 2 3 3 3 SCF Pr HHH CF 2 SCF Pr HBrH Cl 0 3 3 3 SCF Pr HHH CF CF 0 SCF Pr HBrH Cl 1 3 2 3 3 SCF HHH CF CF 1 SCF HBrH Cl 2 Pr Pr 3 2 3 3 SCF Pr HHH CF CF 2 SCF Pr HBrH I 0 3 2 3 3 SCF H H H CF(CF ) 0 SCF HBrH I 1 Pr Pr 3 3 2 3 SCF Pr H H H CF(CF ) 1 SCF Pr HBrH I 2 3 3 2 3 SCF H H H CF(CF ) 2 SCF HIH F 0 Pr Pr 3 3 2 3 SCF Pr HHH SMe 0 SCF Pr HIH F 1 SCF HHH SMe 1 SCF HIH F 2 Pr Pr SCF Pr HHH SMe 2 SCF Pr HIH Cl 0 SCF Pr HHH SOMe 0 SCF Pr HIH Cl 1 SCF HHH SOMe 1 SCF HIH Cl 2 Pr Pr SCF Pr HHH SOMe 2 SCF Pr HIH Br 0 SCF HHH SO Me 0 SCF HIH Br 1 Pr Pr 3 2 3 SCF Pr HHH SO Me 1 SCF Pr HIH Br 2 3 2 3 SCF HHH SO Me 2 SCF HFH CN 0 Pr Pr 3 2 3 SCF Pr HHH OMe 0 SCF Pr HFH CN 1 SCF Pr HHH OMe 1 SCF Pr HFH CN 2 SCF Pr HHH OMe 2 SCF Pr HClH CN 0 SCF Pr HHH OCF 0 SCF Pr HClH CN 1 3 3 3 SCF HHH OCF 1 SCF HClH CN 2 Pr Pr 3 3 3 SCF Pr HHH OCF 2 SCF Pr HBrH CN 0 3 3 3 SCF HHH NO 0 SCF HBrH CN 1 Pr Pr 3 2 3 SCF Pr HHH NO 1 SCF Pr HBrH CN 2 3 2 3 SCF HHH NO 2 SCF HIH CN 0 Pr Pr 3 2 3 SCF Pr HHH CN 0 SCF Pr HIH CN 1 SCF Pr HHH CN 1 SCF Pr HIH CN 2 SCF Pr HHH CN 2 SCF Pr HCF HF 0 3 3 3 SCF Pr HFH F 0 SCF Pr HCF HF 1 3 3 3 SCF HFH F 1 SCF HCF HF 2 Pr Pr 3 3 3 SCF Pr HFH F 2 SCF Pr HCF HCl 0 3 3 3 SCF HClH Cl 0 SCF HCF HCl 1 Pr Pr 3 3 3 SCF Pr HClH Cl 1 SCF Pr HCF HCl 2 3 3 3 SCF HClH Cl 2 SCF HCF HBr 0 Pr Pr 3 3 3 SCF Pr HBrH Br 0 SCF Pr HCF HBr 1 3 3 3 SCF HBrH Br 1 SCF HCF HBr 2 Pr Pr 3 3 3 SCF Pr HBrH Br 2 SCF Pr HCF HI 0 3 3 3 SCF Pr HIH I 0 SCF Pr HCF HI 1 3 3 3 SCF HIH I 1 SCF HCF HI 2 Pr Pr 3 3 3 SCF Pr HIH I 2 SCF Pr HCF HCN 0 3 3 3 SCF HFH Cl 0 SCF HCF HCN 1 Pr Pr 3 3 3 SCF Pr HFH Cl 1 SCF Pr HCF HCN 2 3 3 3 SCF HFH Cl 2 SCF HFF H 0 Pr Pr SCF Pr HFH Br 0 SCF Pr HFF H 1 SCF Pr HFH Br 1 SCF Pr HFF H 2 SCF Pr HFH Br 2 SCF Pr HCl Cl H 0 SCF Pr HFH I 0 SCF Pr HCl Cl H 1 SCF HFH I 1 SCF HCl Cl H 2 Pr Pr SCF Pr HFH I 2 SCF Pr HBr Br H 0 SCF HClH F 0 SCF HBr Br H 1 Pr Pr SCF Pr HClH F 1 SCF Pr HBr Br H 2 SCF HClH F 2 SCF HII H 0 Pr Pr SCF Pr HClH Br 0 SCF Pr HII H 1 SCF HClH Br 1 SCF HII H 2 Pr Pr SCF Pr HClH Br 2 SCF Pr HF Cl H 0 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Pr HF Cl H 1 SCF Pr HHH H 0 SCF HF Cl H 2 SCF HHH H 1 Pr Pr SCF Pr HF Br H 0 SCF Pr HHH H 2 SCF HF Br H 1 SCF FHH H 0 Pr Pr SCF Pr HF Br H 2 SCF Pr FHH H 1 SCF HFI H 0 SCF FHH H 2 Pr Pr SCF Pr HFI H 1 SCF Pr Cl H H H 0 SCF Pr HFI H 2 SCF Pr Cl H H H 1 SCF Pr HClF H 0 SCF Pr Cl H H H 2 SCF Pr HClF H 1 SCF Pr Br H H H 0 SCF HClF H 2 SCF Br H H H 1 Pr Pr SCF Pr HCl Br H 0 SCF Pr Br H H H 2 SCF HCl Br H 1 SCF IHH H 0 Pr Pr SCF Pr HCl Br H 2 SCF Pr IHH H 1 SCF HClI H 0 SCF IHH H 2 Pr Pr SCF Pr HClI H 1 SCF Pr Me H H H 0 SCF Pr HClI H 2 SCF Pr Me H H H 1 SCF Pr HBrF H 0 SCF Pr Me H H H 2 SCF Pr HBrF H 1 SCF Pr CF HH H 0 3 3 3 SCF HBrF H 2 SCF CF HH H 1 Pr Pr 3 3 3 SCF Pr HBr Cl H 0 SCF Pr CF HH H 2 3 3 3 SCF HBr Cl H 1 SCF HFH H 0 Pr Pr SCF Pr HBr Cl H 2 SCF Pr HFH H 1 SCF HBrI H 0 SCF HFH H 2 Pr Pr SCF Pr HBrI H 1 SCF Pr HClH H 0 SCF HBrI H 2 SCF HClH H 1 Pr Pr SCF Pr HIF H 0 SCF Pr HClH H 2 SCF Pr HIF H 1 SCF Pr HBrH H 0 SCF Pr HIF H 2 SCF Pr HBrH H 1 SCF Pr HI Cl H 0 SCF Pr HBrH H 2 SCF HI Cl H 1 SCF HIH H 0 Pr Pr SCF Pr HI Cl H 2 SCF Pr HIH H 1 SCF HI Br H 0 SCF HIH H 2 Pr Pr SCF Pr HI Br H 1 SCF Pr HMeH H 0 SCF HI Br H 2 SCF HMeH H 1 Pr Pr SCF Pr HF CN H 0 SCF Pr HMeH H 2 SCF Pr HF CN H 1 SCF Pr HCF HH 0 3 3 3 SCF Pr HF CN H 2 SCF Pr HCF HH 1 3 3 3 SCF Pr HCl CN H 0 SCF Pr HCF HH 2 3 3 3 SCF HCl CN H 1 SCF HCF CF HH 0 Pr Pr 3 3 2 3 SCF Pr HCl CN H 2 SCF Pr HCF CF HH 1 3 3 2 3 SCF HBr CN H 0 SCF HCF CF HH 2 Pr Pr 3 3 2 3 SCF Pr HBr CN H 1 SCF Pr H CF(CF ) HH 0 3 3 3 2 SCF HBr CN H 2 SCF H CF(CF ) HH 1 Pr Pr 3 3 3 2 SCF Pr HI CN H 0 SCF Pr H CF(CF ) HH 2 3 3 3 2 SCF HI CN H 1 SCF H SMe H H 0 Pr Pr SCF Pr HI CN H 2 SCF Pr H SMe H H 1 SCF HCF FH 0 SCF H SMe H H 2 Pr Pr 3 3 3 SCF Pr HCF FH 1 SCF Pr HSOMeH H 0 3 3 3 SCF Pr HCF FH 2 SCF Pr HSOMeH H 1 3 3 3 SCF HCF Cl H 0 SCF HSOMeH H 2 Pr Pr 3 3 3 SCF Pr HCF Cl H 1 SCF Pr HSO Me H H 0 3 3 3 2 SCF HCF Cl H 2 SCF HSO Me H H 1 Pr Pr 3 3 3 2 SCF Pr HCF Br H 0 SCF Pr HSO Me H H 2 3 3 3 2 SCF HCF Br H 1 SCF H OMe H H 0 Pr Pr 3 3 3 SCF Pr HCF Br H 2 SCF Pr H OMe H H 1 3 3 3 SCF Pr HCF IH 0 SCF Pr H OMe H H 2 3 3 3 SCF Pr HCF IH 1 SCF Pr HOCF HH 0 3 3 3 3 SCF Pr HCF IH 2 SCF Pr HOCF HH 1 3 3 3 3 SCF Pr HCF CN H 0 SCF Pr HOCF HH 2 3 3 3 3 SCF Pr HCF CN H 1 SCF Pr HNO HH 0 3 3 3 2 SCF HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Pr HNO HH 1 SCF Pr HHH I 2 3 2 3 SCF HNO HH 2 SCF HHH Me 0 Pr Pr 3 2 3 SCF Pr HCNH H 0 SCF Pr HHH Me 1 SCF HCNH H 1 SCF HHH Me 2 Pr Pr SCF Pr HCNH H 2 SCF Pr HHH CF 0 3 3 3 SCF Pr HHF H 0 SCF Pr HHH CF 1 3 3 3 SCF Pr HHF H 1 SCF Pr HHH CF 2 3 3 3 SCF Pr HHF H 2 SCF Pr HHH CF CF 0 3 3 2 3 SCF HH Cl H 0 SCF HHH CF CF 1 Pr Pr 3 3 2 3 SCF Pr HH Cl H 1 SCF Pr HHH CF CF 2 3 3 2 3 SCF HH Cl H 2 SCF H H H CF(CF ) 0 Pr Pr 3 3 3 2 SCF Pr HH Br H 0 SCF Pr H H H CF(CF ) 1 3 3 3 2 SCF HH Br H 1 SCF H H H CF(CF ) 2 Pr Pr 3 3 3 2 SCF Pr HH Br H 2 SCF Pr HHH SMe 0 SCF HHI H 0 SCF HHH SMe 1 Pr Pr SCF Pr HHI H 1 SCF Pr HHH SMe 2 SCF Pr HHI H 2 SCF Pr HHH SOMe 0 SCF HH Me H 0 SCF HHH SOMe 1 Pr Pr SCF Pr HH Me H 1 SCF Pr HHH SOMe 2 SCF HH Me H 2 SCF HHH SO Me 0 Pr Pr 3 3 2 SCF Pr HH CF H 0 SCF Pr HHH SO Me 1 3 3 3 2 SCF HH CF H 1 SCF HHH SO Me 2 Pr Pr 3 3 3 2 SCF Pr HH CF H 2 SCF Pr HHH OMe 0 3 3 3 SCF Pr HH CF CF H 0 SCF Pr HHH OMe 1 3 2 3 3 SCF Pr HH CF CF H 1 SCF Pr HHH OMe 2 3 2 3 3 SCF Pr HH CF CF H 2 SCF Pr HHH OCF 0 3 2 3 3 3 SCF H H CF(CF ) H 0 SCF HHH OCF 1 Pr Pr 3 3 2 3 3 SCF Pr H H CF(CF ) H 1 SCF Pr HHH OCF 2 3 3 2 3 3 SCF H H CF(CF ) H 2 SCF HHH NO 0 Pr Pr 3 3 2 3 2 SCF Pr HH SMe H 0 SCF Pr HHH NO 1 3 3 2 SCF HH SMe H 1 SCF HHH NO 2 Pr Pr 3 3 2 SCF Pr HH SMe H 2 SCF Pr HHH CN 0 SCF Pr H H SOMe H 0 SCF Pr HHH CN 1 SCF Pr H H SOMe H 1 SCF Pr HHH CN 2 SCF Pr H H SOMe H 2 SCF Pr HFH F 0 SCF HH SO Me H 0 SCF HFH F 1 Pr Pr 3 2 3 SCF Pr HH SO Me H 1 SCF Pr HFH F 2 3 2 3 SCF HH SO Me H 2 SCF HClH Cl 0 Pr Pr 3 2 3 SCF Pr HH OMe H 0 SCF Pr HClH Cl 1 SCF HH OMe H 1 SCF HClH Cl 2 Pr Pr SCF Pr HH OMe H 2 SCF Pr HBrH Br 0 SCF H H OCF H 0 SCF HBrH Br 1 Pr Pr 3 3 3 SCF Pr H H OCF H 1 SCF Pr HBrH Br 2 3 3 3 SCF Pr H H OCF H 2 SCF Pr HIH I 0 3 3 3 SCF HH NO H 0 SCF HIH I 1 Pr Pr 3 2 3 SCF Pr HH NO H 1 SCF Pr HIH I 2 3 2 3 SCF HH NO H 2 SCF HFH Cl 0 Pr Pr 3 2 3 SCF Pr HH CN H 0 SCF Pr HFH Cl 1 SCF HH CN H 1 SCF HFH Cl 2 Pr Pr SCF Pr HH CN H 2 SCF Pr HFH Br 0 SCF Pr HHH F 0 SCF Pr HFH Br 1 SCF Pr HHH F 1 SCF Pr HFH Br 2 SCF Pr HHH F 2 SCF Pr HFH I 0 SCF HHH Cl 0 SCF HFH I 1 Pr Pr SCF Pr HHH Cl 1 SCF Pr HFH I 2 SCF HHH Cl 2 SCF HClH F 0 Pr Pr SCF Pr HHH Br 0 SCF Pr HClH F 1 SCF HHH Br 1 SCF HClH F 2 Pr Pr SCF Pr HHH Br 2 SCF Pr HClH Br 0 SCF HHH I 0 SCF HClH Br 1 Pr Pr SCF Pr HHH I 1 SCF Pr HClH Br 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF Pr HClH I 0 SCF Pr HF Cl H 1 SCF HClH I 1 SCF HF Cl H 2 Pr Pr SCF Pr HClH I 2 SCF Pr HF Br H 0 SCF HBrH F 0 SCF HF Br H 1 Pr Pr SCF Pr HBrH F 1 SCF Pr HF Br H 2 SCF HBrH F 2 SCF HFI H 0 Pr Pr SCF Pr HBrH Cl 0 SCF Pr HFI H 1 SCF Pr HBrH Cl 1 SCF Pr HFI H 2 SCF Pr HBrH Cl 2 SCF Pr HClF H 0 SCF Pr HBrH I 0 SCF Pr HClF H 1 SCF HBrH I 1 SCF HClF H 2 Pr Pr SCF Pr HBrH I 2 SCF Pr HCl Br H 0 SCF HIH F 0 SCF HCl Br H 1 Pr Pr SCF Pr HIH F 1 SCF Pr HCl Br H 2 SCF HIH F 2 SCF HClI H 0 Pr Pr SCF Pr HIH Cl 0 SCF Pr HClI H 1 SCF Pr HIH Cl 1 SCF Pr HClI H 2 SCF Pr HIH Cl 2 SCF Pr HBrF H 0 SCF Pr HIH Br 0 SCF Pr HBrF H 1 SCF HIH Br 1 SCF HBrF H 2 Pr Pr SCF Pr HIH Br 2 SCF Pr HBr Cl H 0 SCF HFH CN 0 SCF HBr Cl H 1 Pr Pr SCF Pr HFH CN 1 SCF Pr HBr Cl H 2 SCF HFH CN 2 SCF HBrI H 0 Pr Pr SCF Pr HClH CN 0 SCF Pr HBrI H 1 SCF HClH CN 1 SCF HBrI H 2 Pr Pr SCF Pr HClH CN 2 SCF Pr HIF H 0 SCF Pr HBrH CN 0 SCF Pr HIF H 1 SCF Pr HBrH CN 1 SCF Pr HIF H 2 SCF Pr HBrH CN 2 SCF Pr HI Cl H 0 SCF HIH CN 0 SCF HI Cl H 1 Pr Pr SCF Pr HIH CN 1 SCF Pr HI Cl H 2 SCF HIH CN 2 SCF HI Br H 0 Pr Pr SCF Pr HCF HF 0 SCF Pr HI Br H 1 3 3 3 SCF HCF HF 1 SCF HI Br H 2 Pr Pr 3 3 3 SCF Pr HCF HF 2 SCF Pr HF CN H 0 3 3 3 SCF Pr HCF HCl 0 SCF Pr HF CN H 1 3 3 3 SCF Pr HCF HCl 1 SCF Pr HF CN H 2 3 3 3 SCF Pr HCF HCl 2 SCF Pr HCl CN H 0 3 3 3 SCF HCF HBr 0 SCF HCl CN H 1 Pr Pr 3 3 3 SCF Pr HCF HBr 1 SCF Pr HCl CN H 2 3 3 3 SCF HCF HBr 2 SCF HBr CN H 0 Pr Pr 3 3 3 SCF Pr HCF HI 0 SCF Pr HBr CN H 1 3 3 3 SCF HCF HI 1 SCF HBr CN H 2 Pr Pr 3 3 3 SCF Pr HCF HI 2 SCF Pr HI CN H 0 3 3 3 SCF HCF HCN 0 SCF HI CN H 1 Pr Pr 3 3 3 SCF Pr HCF HCN 1 SCF Pr HI CN H 2 3 3 3 SCF HCF HCN 2 SCF HCF FH 0 Pr Pr 3 3 3 3 SCF Pr HFF H 0 SCF Pr HCF FH 1 3 3 3 SCF Pr HFF H 1 SCF Pr HCF FH 2 3 3 3 SCF HFF H 2 SCF HCF Cl H 0 Pr Pr 3 3 3 SCF Pr HCl Cl H 0 SCF Pr HCF Cl H 1 3 3 3 SCF HCl Cl H 1 SCF HCF Cl H 2 Pr Pr 3 3 3 SCF Pr HCl Cl H 2 SCF Pr HCF Br H 0 3 3 3 SCF HBr Br H 0 SCF HCF Br H 1 Pr Pr 3 3 3 SCF Pr HBr Br H 1 SCF Pr HCF Br H 2 3 3 3 SCF Pr HBr Br H 2 SCF Pr HCF IH 0 3 3 3 SCF Pr HII H 0 SCF Pr HCF IH 1 3 3 3 SCF Pr HII H 1 SCF Pr HCF IH 2 3 3 3 SCF Pr HII H 2 SCF Pr HCF CN H 0 3 3 3 SCF Pr HF Cl H 0 SCF Pr HCF CN H 1 3 3 3 SCF HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF CH CF HHH H 0 SCF CH CF HNO HH 1 3 2 3 3 2 3 2 SCF CH CF HHH H 1 SCF CH CF HNO HH 2 3 2 3 3 2 3 2 SCF CH CF HHH H 2 SCF CH CF HCNH H 0 3 2 3 3 2 3 SCF CH CF FHH H 0 SCF CH CF HCNH H 1 3 2 3 3 2 3 SCF CH CF FHH H 1 SCF CH CF HCNH H 2 3 2 3 3 2 3 SCF CH CF FHH H 2 SCF CH CF HHF H 0 3 2 3 3 2 3 SCF CH CF Cl H H H 0 SCF CH CF HHF H 1 3 2 3 3 2 3 SCF CH CF Cl H H H 1 SCF CH CF HHF H 2 3 2 3 3 2 3 SCF CH CF Cl H H H 2 SCF CH CF HH Cl H 0 3 2 3 3 2 3 SCF CH CF Br H H H 0 SCF CH CF HH Cl H 1 3 2 3 3 2 3 SCF CH CF Br H H H 1 SCF CH CF HH Cl H 2 3 2 3 3 2 3 SCF CH CF Br H H H 2 SCF CH CF HH Br H 0 3 2 3 3 2 3 SCF CH CF IHH H 0 SCF CH CF HH Br H 1 3 2 3 3 2 3 SCF CH CF IHH H 1 SCF CH CF HH Br H 2 3 2 3 3 2 3 SCF CH CF IHH H 2 SCF CH CF HHI H 0 3 2 3 3 2 3 SCF CH CF Me H H H 0 SCF CH CF HHI H 1 3 2 3 3 2 3 SCF CH CF Me H H H 1 SCF CH CF HHI H 2 3 2 3 3 2 3 SCF CH CF Me H H H 2 SCF CH CF HH Me H 0 3 2 3 3 2 3 SCF CH CF CF HH H 0 SCF CH CF HH Me H 1 3 2 3 3 3 2 3 SCF CH CF CF HH H 1 SCF CH CF HH Me H 2 3 2 3 3 3 2 3 SCF CH CF CF HH H 2 SCF CH CF HH CF H 0 3 2 3 3 3 2 3 3 SCF CH CF HFH H 0 SCF CH CF HH CF H 1 3 2 3 3 2 3 3 SCF CH CF HFH H 1 SCF CH CF HH CF H 2 3 2 3 3 2 3 3 SCF CH CF HFH H 2 SCF CH CF HH CF CF H 0 3 2 3 3 2 3 2 3 SCF CH CF HClH H 0 SCF CH CF HH CF CF H 1 3 2 3 3 2 3 2 3 SCF CH CF HClH H 1 SCF CH CF HH CF CF H 2 3 2 3 3 2 3 2 3 SCF CH CF HClH H 2 SCF CH CF H H CF(CF ) H 0 3 2 3 3 2 3 3 2 SCF CH CF HBrH H 0 SCF CH CF H H CF(CF ) H 1 3 2 3 3 2 3 3 2 SCF CH CF HBrH H 1 SCF CH CF H H CF(CF ) H 2 3 2 3 3 2 3 3 2 SCF CH CF HBrH H 2 SCF CH CF HH SMe H 0 3 2 3 3 2 3 SCF CH CF HIH H 0 SCF CH CF HH SMe H 1 3 2 3 3 2 3 SCF CH CF HIH H 1 SCF CH CF HH SMe H 2 3 2 3 3 2 3 SCF CH CF HIH H 2 SCF CH CF H H SOMe H 0 3 2 3 3 2 3 SCF CH CF HMeH H 0 SCF CH CF H H SOMe H 1 3 2 3 3 2 3 SCF CH CF HMeH H 1 SCF CH CF H H SOMe H 2 3 2 3 3 2 3 SCF CH CF HMeH H 2 SCF CH CF HH SO Me H 0 3 2 3 3 2 3 2 SCF CH CF HCF HH 0 SCF CH CF HH SO Me H 1 3 2 3 3 3 2 3 2 SCF CH CF HCF HH 1 SCF CH CF HH SO Me H 2 3 2 3 3 3 2 3 2 SCF CH CF HCF HH 2 SCF CH CF HH OMe H 0 3 2 3 3 3 2 3 SCF CH CF HCF CF HH 0 SCF CH CF HH OMe H 1 3 2 3 2 3 3 2 3 SCF CH CF HCF CF HH 1 SCF CH CF HH OMe H 2 3 2 3 2 3 3 2 3 SCF CH CF HCF CF HH 2 SCF CH CF H H OCF H 0 3 2 3 2 3 3 2 3 3 SCF CH CF H CF(CF ) HH 0 SCF CH CF H H OCF H 1 3 2 3 3 2 3 2 3 3 SCF CH CF H CF(CF ) HH 1 SCF CH CF H H OCF H 2 3 2 3 3 2 3 2 3 3 SCF CH CF H CF(CF ) HH 2 SCF CH CF HH NO H 0 3 2 3 3 2 3 2 3 2 SCF CH CF H SMe H H 0 SCF CH CF HH NO H 1 3 2 3 3 2 3 2 SCF CH CF H SMe H H 1 SCF CH CF HH NO H 2 3 2 3 3 2 3 2 SCF CH CF H SMe H H 2 SCF CH CF HH CN H 0 3 2 3 3 2 3 SCF CH CF HSOMeH H 0 SCF CH CF HH CN H 1 3 2 3 3 2 3 SCF CH CF HSOMeH H 1 SCF CH CF HH CN H 2 3 2 3 3 2 3 SCF CH CF HSOMeH H 2 SCF CH CF HHH F 0 3 2 3 3 2 3 SCF CH CF HSO Me H H 0 SCF CH CF HHH F 1 3 2 3 2 3 2 3 SCF CH CF HSO Me H H 1 SCF CH CF HHH F 2 3 2 3 2 3 2 3 SCF CH CF HSO Me H H 2 SCF CH CF HHH Cl 0 3 2 3 2 3 2 3 SCF CH CF H OMe H H 0 SCF CH CF HHH Cl 1 3 2 3 3 2 3 SCF CH CF H OMe H H 1 SCF CH CF HHH Cl 2 3 2 3 3 2 3 SCF CH CF H OMe H H 2 SCF CH CF HHH Br 0 3 2 3 3 2 3 SCF CH CF HOCF HH 0 SCF CH CF HHH Br 1 3 2 3 3 3 2 3 SCF CH CF HOCF HH 1 SCF CH CF HHH Br 2 3 2 3 3 3 2 3 SCF CH CF HOCF HH 2 SCF CH CF HHH I 0 3 2 3 3 3 2 3 SCF CH CF HNO HH 0 SCF CH CF HHH I 1 3 2 3 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF CH CF HHH I 2 SCF CH CF HClH I 0 3 2 3 3 2 3 SCF CH CF HHH Me 0 SCF CH CF HClH I 1 3 2 3 3 2 3 SCF CH CF HHH Me 1 SCF CH CF HClH I 2 3 2 3 3 2 3 SCF CH CF HHH Me 2 SCF CH CF HBrH F 0 3 2 3 3 2 3 SCF CH CF HHH CF 0 SCF CH CF HBrH F 1 3 2 3 3 3 2 3 SCF CH CF HHH CF 1 SCF CH CF HBrH F 2 3 2 3 3 3 2 3 SCF CH CF HHH CF 2 SCF CH CF HBrH Cl 0 3 2 3 3 3 2 3 SCF CH CF HHH CF CF 0 SCF CH CF HBrH Cl 1 3 2 3 2 3 3 2 3 SCF CH CF HHH CF CF 1 SCF CH CF HBrH Cl 2 3 2 3 2 3 3 2 3 SCF CH CF HHH CF CF 2 SCF CH CF HBrH I 0 3 2 3 2 3 3 2 3 SCF CH CF H H H CF(CF ) 0 SCF CH CF HBrH I 1 3 2 3 3 2 3 2 3 SCF CH CF H H H CF(CF ) 1 SCF CH CF HBrH I 2 3 2 3 3 2 3 2 3 SCF CH CF H H H CF(CF ) 2 SCF CH CF HIH F 0 3 2 3 3 2 3 2 3 SCF CH CF HHH SMe 0 SCF CH CF HIH F 1 3 2 3 3 2 3 SCF CH CF HHH SMe 1 SCF CH CF HIH F 2 3 2 3 3 2 3 SCF CH CF HHH SMe 2 SCF CH CF HIH Cl 0 3 2 3 3 2 3 SCF CH CF HHH SOMe 0 SCF CH CF HIH Cl 1 3 2 3 3 2 3 SCF CH CF HHH SOMe 1 SCF CH CF HIH Cl 2 3 2 3 3 2 3 SCF CH CF HHH SOMe 2 SCF CH CF HIH Br 0 3 2 3 3 2 3 SCF CH CF HHH SO Me 0 SCF CH CF HIH Br 1 3 2 3 2 3 2 3 SCF CH CF HHH SO Me 1 SCF CH CF HIH Br 2 3 2 3 2 3 2 3 SCF CH CF HHH SO Me 2 SCF CH CF HFH CN 0 3 2 3 2 3 2 3 SCF CH CF HHH OMe 0 SCF CH CF HFH CN 1 3 2 3 3 2 3 SCF CH CF HHH OMe 1 SCF CH CF HFH CN 2 3 2 3 3 2 3 SCF CH CF HHH OMe 2 SCF CH CF HClH CN 0 3 2 3 3 2 3 SCF CH CF HHH OCF 0 SCF CH CF HClH CN 1 3 2 3 3 3 2 3 SCF CH CF HHH OCF 1 SCF CH CF HClH CN 2 3 2 3 3 3 2 3 SCF CH CF HHH OCF 2 SCF CH CF HBrH CN 0 3 2 3 3 3 2 3 SCF CH CF HHH NO 0 SCF CH CF HBrH CN 1 3 2 3 2 3 2 3 SCF CH CF HHH NO 1 SCF CH CF HBrH CN 2 3 2 3 2 3 2 3 SCF CH CF HHH NO 2 SCF CH CF HIH CN 0 3 2 3 2 3 2 3 SCF CH CF HHH CN 0 SCF CH CF HIH CN 1 3 2 3 3 2 3 SCF CH CF HHH CN 1 SCF CH CF HIH CN 2 3 2 3 3 2 3 SCF CH CF HHH CN 2 SCF CH CF HCF HF 0 3 2 3 3 2 3 3 SCF CH CF HFH F 0 SCF CH CF HCF HF 1 3 2 3 3 2 3 3 SCF CH CF HFH F 1 SCF CH CF HCF HF 2 3 2 3 3 2 3 3 SCF CH CF HFH F 2 SCF CH CF HCF HCl 0 3 2 3 3 2 3 3 SCF CH CF HClH Cl 0 SCF CH CF HCF HCl 1 3 2 3 3 2 3 3 SCF CH CF HClH Cl 1 SCF CH CF HCF HCl 2 3 2 3 3 2 3 3 SCF CH CF HClH Cl 2 SCF CH CF HCF HBr 0 3 2 3 3 2 3 3 SCF CH CF HBrH Br 0 SCF CH CF HCF HBr 1 3 2 3 3 2 3 3 SCF CH CF HBrH Br 1 SCF CH CF HCF HBr 2 3 2 3 3 2 3 3 SCF CH CF HBrH Br 2 SCF CH CF HCF HI 0 3 2 3 3 2 3 3 SCF CH CF HIH I 0 SCF CH CF HCF HI 1 3 2 3 3 2 3 3 SCF CH CF HIH I 1 SCF CH CF HCF HI 2 3 2 3 3 2 3 3 SCF CH CF HIH I 2 SCF CH CF HCF HCN 0 3 2 3 3 2 3 3 SCF CH CF HFH Cl 0 SCF CH CF HCF HCN 1 3 2 3 3 2 3 3 SCF CH CF HFH Cl 1 SCF CH CF HCF HCN 2 3 2 3 3 2 3 3 SCF CH CF HFH Cl 2 SCF CH CF HFF H 0 3 2 3 3 2 3 SCF CH CF HFH Br 0 SCF CH CF HFF H 1 3 2 3 3 2 3 SCF CH CF HFH Br 1 SCF CH CF HFF H 2 3 2 3 3 2 3 SCF CH CF HFH Br 2 SCF CH CF HCl Cl H 0 3 2 3 3 2 3 SCF CH CF HFH I 0 SCF CH CF HCl Cl H 1 3 2 3 3 2 3 SCF CH CF HFH I 1 SCF CH CF HCl Cl H 2 3 2 3 3 2 3 SCF CH CF HFH I 2 SCF CH CF HBr Br H 0 3 2 3 3 2 3 SCF CH CF HClH F 0 SCF CH CF HBr Br H 1 3 2 3 3 2 3 SCF CH CF HClH F 1 SCF CH CF HBr Br H 2 3 2 3 3 2 3 SCF CH CF HClH F 2 SCF CH CF HII H 0 3 2 3 3 2 3 SCF CH CF HClH Br 0 SCF CH CF HII H 1 3 2 3 3 2 3 SCF CH CF HClH Br 1 SCF CH CF HII H 2 3 2 3 3 2 3 SCF CH CF HClH Br 2 SCF CH CF HF Cl H 0 3 2 3 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SCF CH CF HF Cl H 1 SOCF Me HHH H 0 3 2 3 3 SCF CH CF HF Cl H 2 SOCF Me HHH H 1 3 2 3 3 SCF CH CF HF Br H 0 SOCF Me HHH H 2 3 2 3 3 SCF CH CF HF Br H 1 SOCF Me FHH H 0 3 2 3 3 SCF CH CF HF Br H 2 SOCF Me FHH H 1 3 2 3 3 SCF CH CF HFI H 0 SOCF Me FHH H 2 3 2 3 3 SCF CH CF HFI H 1 SOCF Me Cl H H H 0 3 2 3 3 SCF CH CF HFI H 2 SOCF Me Cl H H H 1 3 2 3 3 SCF CH CF HClF H 0 SOCF Me Cl H H H 2 3 2 3 3 SCF CH CF HClF H 1 SOCF Me Br H H H 0 3 2 3 3 SCF CH CF HClF H 2 SOCF Me Br H H H 1 3 2 3 3 SCF CH CF HCl Br H 0 SOCF Me Br H H H 2 3 2 3 3 SCF CH CF HCl Br H 1 SOCF Me IHH H 0 3 2 3 3 SCF CH CF HCl Br H 2 SOCF Me IHH H 1 3 2 3 3 SCF CH CF HClI H 0 SOCF Me IHH H 2 3 2 3 3 SCF CH CF HClI H 1 SOCF Me Me H H H 0 3 2 3 3 SCF CH CF HClI H 2 SOCF Me Me H H H 1 3 2 3 3 SCF CH CF HBrF H 0 SOCF Me Me H H H 2 3 2 3 3 SCF CH CF HBrF H 1 SOCF Me CF HH H 0 3 2 3 3 3 SCF CH CF HBrF H 2 SOCF Me CF HH H 1 3 2 3 3 3 SCF CH CF HBr Cl H 0 SOCF Me CF HH H 2 3 2 3 3 3 SCF CH CF HBr Cl H 1 SOCF Me HFH H 0 3 2 3 3 SCF CH CF HBr Cl H 2 SOCF Me HFH H 1 3 2 3 3 SCF CH CF HBrI H 0 SOCF Me HFH H 2 3 2 3 3 SCF CH CF HBrI H 1 SOCF Me HClH H 0 3 2 3 3 SCF CH CF HBrI H 2 SOCF Me HClH H 1 3 2 3 3 SCF CH CF HIF H 0 SOCF Me HClH H 2 3 2 3 3 SCF CH CF HIF H 1 SOCF Me HBrH H 0 3 2 3 3 SCF CH CF HIF H 2 SOCF Me HBrH H 1 3 2 3 3 SCF CH CF HI Cl H 0 SOCF Me HBrH H 2 3 2 3 3 SCF CH CF HI Cl H 1 SOCF Me HIH H 0 3 2 3 3 SCF CH CF HI Cl H 2 SOCF Me HIH H 1 3 2 3 3 SCF CH CF HI Br H 0 SOCF Me HIH H 2 3 2 3 3 SCF CH CF HI Br H 1 SOCF Me HMeH H 0 3 2 3 3 SCF CH CF HI Br H 2 SOCF Me HMeH H 1 3 2 3 3 SCF CH CF HF CN H 0 SOCF Me HMeH H 2 3 2 3 3 SCF CH CF HF CN H 1 SOCF Me HCF HH 0 3 2 3 3 3 SCF CH CF HF CN H 2 SOCF Me HCF HH 1 3 2 3 3 3 SCF CH CF HCl CN H 0 SOCF Me HCF HH 2 3 2 3 3 3 SCF CH CF HCl CN H 1 SOCF Me HCF CF HH 0 3 2 3 3 2 3 SCF CH CF HCl CN H 2 SOCF Me HCF CF HH 1 3 2 3 3 2 3 SCF CH CF HBr CN H 0 SOCF Me HCF CF HH 2 3 2 3 3 2 3 SCF CH CF HBr CN H 1 SOCF Me H CF(CF ) HH 0 3 2 3 3 3 2 SCF CH CF HBr CN H 2 SOCF Me H CF(CF ) HH 1 3 2 3 3 3 2 SCF CH CF HI CN H 0 SOCF Me H CF(CF ) HH 2 3 2 3 3 3 2 SCF CH CF HI CN H 1 SOCF Me H SMe H H 0 3 2 3 3 SCF CH CF HI CN H 2 SOCF Me H SMe H H 1 3 2 3 3 SCF CH CF HCF FH 0 SOCF Me H SMe H H 2 3 2 3 3 3 SCF CH CF HCF FH 1 SOCF Me HSOMeH H 0 3 2 3 3 3 SCF CH CF HCF FH 2 SOCF Me HSOMeH H 1 3 2 3 3 3 SCF CH CF HCF Cl H 0 SOCF Me HSOMeH H 2 3 2 3 3 3 SCF CH CF HCF Cl H 1 SOCF Me HSO Me H H 0 3 2 3 3 3 2 SCF CH CF HCF Cl H 2 SOCF Me HSO Me H H 1 3 2 3 3 3 2 SCF CH CF HCF Br H 0 SOCF Me HSO Me H H 2 3 2 3 3 3 2 SCF CH CF HCF Br H 1 SOCF Me H OMe H H 0 3 2 3 3 3 SCF CH CF HCF Br H 2 SOCF Me H OMe H H 1 3 2 3 3 3 SCF CH CF HCF IH 0 SOCF Me H OMe H H 2 3 2 3 3 3 SCF CH CF HCF IH 1 SOCF Me HOCF HH 0 3 2 3 3 3 3 SCF CH CF HCF IH 2 SOCF Me HOCF HH 1 3 2 3 3 3 3 SCF CH CF HCF CN H 0 SOCF Me HOCF HH 2 3 2 3 3 3 3 SCF CH CF HCF CN H 1 SOCF Me HNO HH 0 3 2 3 3 3 2 SCF CH CF HCF CN H 2 3 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Me HNO HH 1 SOCF Me HHH I 2 3 2 3 SOCF Me HNO HH 2 SOCF Me HHH Me 0 3 2 3 SOCF Me HCNH H 0 SOCF Me HHH Me 1 SOCF Me HCNH H 1 SOCF Me HHH Me 2 SOCF Me HCNH H 2 SOCF Me HHH CF 0 3 3 3 SOCF Me HHF H 0 SOCF Me HHH CF 1 3 3 3 SOCF Me HHF H 1 SOCF Me HHH CF 2 3 3 3 SOCF Me HHF H 2 SOCF Me HHH CF CF 0 3 3 2 3 SOCF Me HH Cl H 0 SOCF Me HHH CF CF 1 3 3 2 3 SOCF Me HH Cl H 1 SOCF Me HHH CF CF 2 3 3 2 3 SOCF Me HH Cl H 2 SOCF Me H H H CF(CF ) 0 3 3 3 2 SOCF Me HH Br H 0 SOCF Me H H H CF(CF ) 1 3 3 3 2 SOCF Me HH Br H 1 SOCF Me H H H CF(CF ) 2 3 3 3 2 SOCF Me HH Br H 2 SOCF Me HHH SMe 0 SOCF Me HHI H 0 SOCF Me HHH SMe 1 SOCF Me HHI H 1 SOCF Me HHH SMe 2 SOCF Me HHI H 2 SOCF Me HHH SOMe 0 SOCF Me HH Me H 0 SOCF Me HHH SOMe 1 SOCF Me HH Me H 1 SOCF Me HHH SOMe 2 SOCF Me HH Me H 2 SOCF Me HHH SO Me 0 3 3 2 SOCF Me HH CF H 0 SOCF Me HHH SO Me 1 3 3 3 2 SOCF Me HH CF H 1 SOCF Me HHH SO Me 2 3 3 3 2 SOCF Me HH CF H 2 SOCF Me HHH OMe 0 3 3 3 SOCF Me HH CF CF H 0 SOCF Me HHH OMe 1 3 2 3 3 SOCF Me HH CF CF H 1 SOCF Me HHH OMe 2 3 2 3 3 SOCF Me HH CF CF H 2 SOCF Me HHH OCF 0 3 2 3 3 3 SOCF Me H H CF(CF ) H 0 SOCF Me HHH OCF 1 3 3 2 3 3 SOCF Me H H CF(CF ) H 1 SOCF Me HHH OCF 2 3 3 2 3 3 SOCF Me H H CF(CF ) H 2 SOCF Me HHH NO 0 3 3 2 3 2 SOCF Me HH SMe H 0 SOCF Me HHH NO 1 3 3 2 SOCF Me HH SMe H 1 SOCF Me HHH NO 2 3 3 2 SOCF Me HH SMe H 2 SOCF Me HHH CN 0 SOCF Me H H SOMe H 0 SOCF Me HHH CN 1 SOCF Me H H SOMe H 1 SOCF Me HHH CN 2 SOCF Me H H SOMe H 2 SOCF Me HFH F 0 SOCF Me HH SO Me H 0 SOCF Me HFH F 1 3 2 3 SOCF Me HH SO Me H 1 SOCF Me HFH F 2 3 2 3 SOCF Me HH SO Me H 2 SOCF Me HClH Cl 0 3 2 3 SOCF Me HH OMe H 0 SOCF Me HClH Cl 1 SOCF Me HH OMe H 1 SOCF Me HClH Cl 2 SOCF Me HH OMe H 2 SOCF Me HBrH Br 0 SOCF Me H H OCF H 0 SOCF Me HBrH Br 1 3 3 3 SOCF Me H H OCF H 1 SOCF Me HBrH Br 2 3 3 3 SOCF Me H H OCF H 2 SOCF Me HIH I 0 3 3 3 SOCF Me HH NO H 0 SOCF Me HIH I 1 3 2 3 SOCF Me HH NO H 1 SOCF Me HIH I 2 3 2 3 SOCF Me HH NO H 2 SOCF Me HFH Cl 0 3 2 3 SOCF Me HH CN H 0 SOCF Me HFH Cl 1 SOCF Me HH CN H 1 SOCF Me HFH Cl 2 SOCF Me HH CN H 2 SOCF Me HFH Br 0 SOCF Me HHH F 0 SOCF Me HFH Br 1 SOCF Me HHH F 1 SOCF Me HFH Br 2 SOCF Me HHH F 2 SOCF Me HFH I 0 SOCF Me HHH Cl 0 SOCF Me HFH I 1 SOCF Me HHH Cl 1 SOCF Me HFH I 2 SOCF Me HHH Cl 2 SOCF Me HClH F 0 SOCF Me HHH Br 0 SOCF Me HClH F 1 SOCF Me HHH Br 1 SOCF Me HClH F 2 SOCF Me HHH Br 2 SOCF Me HClH Br 0 SOCF Me HHH I 0 SOCF Me HClH Br 1 SOCF Me HHH I 1 SOCF Me HClH Br 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Me HClH I 0 SOCF Me HF Cl H 1 SOCF Me HClH I 1 SOCF Me HF Cl H 2 SOCF Me HClH I 2 SOCF Me HF Br H 0 SOCF Me HBrH F 0 SOCF Me HF Br H 1 SOCF Me HBrH F 1 SOCF Me HF Br H 2 SOCF Me HBrH F 2 SOCF Me HFI H 0 SOCF Me HBrH Cl 0 SOCF Me HFI H 1 SOCF Me HBrH Cl 1 SOCF Me HFI H 2 SOCF Me HBrH Cl 2 SOCF Me HClF H 0 SOCF Me HBrH I 0 SOCF Me HClF H 1 SOCF Me HBrH I 1 SOCF Me HClF H 2 SOCF Me HBrH I 2 SOCF Me HCl Br H 0 SOCF Me HIH F 0 SOCF Me HCl Br H 1 SOCF Me HIH F 1 SOCF Me HCl Br H 2 SOCF Me HIH F 2 SOCF Me HClI H 0 SOCF Me HIH Cl 0 SOCF Me HClI H 1 SOCF Me HIH Cl 1 SOCF Me HClI H 2 SOCF Me HIH Cl 2 SOCF Me HBrF H 0 SOCF Me HIH Br 0 SOCF Me HBrF H 1 SOCF Me HIH Br 1 SOCF Me HBrF H 2 SOCF Me HIH Br 2 SOCF Me HBr Cl H 0 SOCF Me HFH CN 0 SOCF Me HBr Cl H 1 SOCF Me HFH CN 1 SOCF Me HBr Cl H 2 SOCF Me HFH CN 2 SOCF Me HBrI H 0 SOCF Me HClH CN 0 SOCF Me HBrI H 1 SOCF Me HClH CN 1 SOCF Me HBrI H 2 SOCF Me HClH CN 2 SOCF Me HIF H 0 SOCF Me HBrH CN 0 SOCF Me HIF H 1 SOCF Me HBrH CN 1 SOCF Me HIF H 2 SOCF Me HBrH CN 2 SOCF Me HI Cl H 0 SOCF Me HIH CN 0 SOCF Me HI Cl H 1 SOCF Me HIH CN 1 SOCF Me HI Cl H 2 SOCF Me HIH CN 2 SOCF Me HI Br H 0 SOCF Me HCF HF 0 SOCF Me HI Br H 1 3 3 3 SOCF Me HCF HF 1 SOCF Me HI Br H 2 3 3 3 SOCF Me HCF HF 2 SOCF Me HF CN H 0 3 3 3 SOCF Me HCF HCl 0 SOCF Me HF CN H 1 3 3 3 SOCF Me HCF HCl 1 SOCF Me HF CN H 2 3 3 3 SOCF Me HCF HCl 2 SOCF Me HCl CN H 0 3 3 3 SOCF Me HCF HBr 0 SOCF Me HCl CN H 1 3 3 3 SOCF Me HCF HBr 1 SOCF Me HCl CN H 2 3 3 3 SOCF Me HCF HBr 2 SOCF Me HBr CN H 0 3 3 3 SOCF Me HCF HI 0 SOCF Me HBr CN H 1 3 3 3 SOCF Me HCF HI 1 SOCF Me HBr CN H 2 3 3 3 SOCF Me HCF HI 2 SOCF Me HI CN H 0 3 3 3 SOCF Me HCF HCN 0 SOCF Me HI CN H 1 3 3 3 SOCF Me HCF HCN 1 SOCF Me HI CN H 2 3 3 3 SOCF Me HCF HCN 2 SOCF Me HCF FH 0 3 3 3 3 SOCF Me HFF H 0 SOCF Me HCF FH 1 3 3 3 SOCF Me HFF H 1 SOCF Me HCF FH 2 3 3 3 SOCF Me HFF H 2 SOCF Me HCF Cl H 0 3 3 3 SOCF Me HCl Cl H 0 SOCF Me HCF Cl H 1 3 3 3 SOCF Me HCl Cl H 1 SOCF Me HCF Cl H 2 3 3 3 SOCF Me HCl Cl H 2 SOCF Me HCF Br H 0 3 3 3 SOCF Me HBr Br H 0 SOCF Me HCF Br H 1 3 3 3 SOCF Me HBr Br H 1 SOCF Me HCF Br H 2 3 3 3 SOCF Me HBr Br H 2 SOCF Me HCF IH 0 3 3 3 SOCF Me HII H 0 SOCF Me HCF IH 1 3 3 3 SOCF Me HII H 1 SOCF Me HCF IH 2 3 3 3 SOCF Me HII H 2 SOCF Me HCF CN H 0 3 3 3 SOCF Me HF Cl H 0 SOCF Me HCF CN H 1 3 3 3 SOCF Me HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Et HHH H 0 SOCF Et HNO HH 1 3 3 2 SOCF Et HHH H 1 SOCF Et HNO HH 2 3 3 2 SOCF Et HHH H 2 SOCF Et HCNH H 0 SOCF Et FHH H 0 SOCF Et HCNH H 1 SOCF Et FHH H 1 SOCF Et HCNH H 2 SOCF Et FHH H 2 SOCF Et HHF H 0 SOCF Et Cl H H H 0 SOCF Et HHF H 1 SOCF Et Cl H H H 1 SOCF Et HHF H 2 SOCF Et Cl H H H 2 SOCF Et HH Cl H 0 SOCF Et Br H H H 0 SOCF Et HH Cl H 1 SOCF Et Br H H H 1 SOCF Et HH Cl H 2 SOCF Et Br H H H 2 SOCF Et HH Br H 0 SOCF Et IHH H 0 SOCF Et HH Br H 1 SOCF Et IHH H 1 SOCF Et HH Br H 2 SOCF Et IHH H 2 SOCF Et HHI H 0 SOCF Et Me H H H 0 SOCF Et HHI H 1 SOCF Et Me H H H 1 SOCF Et HHI H 2 SOCF Et Me H H H 2 SOCF Et HH Me H 0 SOCF Et CF HH H 0 SOCF Et HH Me H 1 3 3 3 SOCF Et CF HH H 1 SOCF Et HH Me H 2 3 3 3 SOCF Et CF HH H 2 SOCF Et HH CF H 0 3 3 3 3 SOCF Et HFH H 0 SOCF Et HH CF H 1 3 3 3 SOCF Et HFH H 1 SOCF Et HH CF H 2 3 3 3 SOCF Et HFH H 2 SOCF Et HH CF CF H 0 3 3 2 3 SOCF Et HClH H 0 SOCF Et HH CF CF H 1 3 3 2 3 SOCF Et HClH H 1 SOCF Et HH CF CF H 2 3 3 2 3 SOCF Et HClH H 2 SOCF Et H H CF(CF ) H 0 3 3 3 2 SOCF Et HBrH H 0 SOCF Et H H CF(CF ) H 1 3 3 3 2 SOCF Et HBrH H 1 SOCF Et H H CF(CF ) H 2 3 3 3 2 SOCF Et HBrH H 2 SOCF Et HH SMe H 0 SOCF Et HIH H 0 SOCF Et HH SMe H 1 SOCF Et HIH H 1 SOCF Et HH SMe H 2 SOCF Et HIH H 2 SOCF Et H H SOMe H 0 SOCF Et HMeH H 0 SOCF Et H H SOMe H 1 SOCF Et HMeH H 1 SOCF Et H H SOMe H 2 SOCF Et HMeH H 2 SOCF Et HH SO Me H 0 3 3 2 SOCF Et HCF HH 0 SOCF Et HH SO Me H 1 3 3 3 2 SOCF Et HCF HH 1 SOCF Et HH SO Me H 2 3 3 3 2 SOCF Et HCF HH 2 SOCF Et HH OMe H 0 3 3 3 SOCF Et HCF CF HH 0 SOCF Et HH OMe H 1 3 2 3 3 SOCF Et HCF CF HH 1 SOCF Et HH OMe H 2 3 2 3 3 SOCF Et HCF CF HH 2 SOCF Et H H OCF H 0 3 2 3 3 3 SOCF Et H CF(CF ) HH 0 SOCF Et H H OCF H 1 3 3 2 3 3 SOCF Et H CF(CF ) HH 1 SOCF Et H H OCF H 2 3 3 2 3 3 SOCF Et H CF(CF ) HH 2 SOCF Et HH NO H 0 3 3 2 3 2 SOCF Et H SMe H H 0 SOCF Et HH NO H 1 3 3 2 SOCF Et H SMe H H 1 SOCF Et HH NO H 2 3 3 2 SOCF Et H SMe H H 2 SOCF Et HH CN H 0 SOCF Et HSOMeH H 0 SOCF Et HH CN H 1 SOCF Et HSOMeH H 1 SOCF Et HH CN H 2 SOCF Et HSOMeH H 2 SOCF Et HHH F 0 SOCF Et HSO Me H H 0 SOCF Et HHH F 1 3 2 3 SOCF Et HSO Me H H 1 SOCF Et HHH F 2 3 2 3 SOCF Et HSO Me H H 2 SOCF Et HHH Cl 0 3 2 3 SOCF Et H OMe H H 0 SOCF Et HHH Cl 1 SOCF Et H OMe H H 1 SOCF Et HHH Cl 2 SOCF Et H OMe H H 2 SOCF Et HHH Br 0 SOCF Et HOCF HH 0 SOCF Et HHH Br 1 3 3 3 SOCF Et HOCF HH 1 SOCF Et HHH Br 2 3 3 3 SOCF Et HOCF HH 2 SOCF Et HHH I 0 3 3 3 SOCF Et HNO HH 0 SOCF Et HHH I 1 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Et HHH I 2 SOCF Et HClH I 0 SOCF Et HHH Me 0 SOCF Et HClH I 1 SOCF Et HHH Me 1 SOCF Et HClH I 2 SOCF Et HHH Me 2 SOCF Et HBrH F 0 SOCF Et HHH CF 0 SOCF Et HBrH F 1 3 3 3 SOCF Et HHH CF 1 SOCF Et HBrH F 2 3 3 3 SOCF Et HHH CF 2 SOCF Et HBrH Cl 0 3 3 3 SOCF Et HHH CF CF 0 SOCF Et HBrH Cl 1 3 2 3 3 SOCF Et HHH CF CF 1 SOCF Et HBrH Cl 2 3 2 3 3 SOCF Et HHH CF CF 2 SOCF Et HBrH I 0 3 2 3 3 SOCF Et H H H CF(CF ) 0 SOCF Et HBrH I 1 3 3 2 3 SOCF Et H H H CF(CF ) 1 SOCF Et HBrH I 2 3 3 2 3 SOCF Et H H H CF(CF ) 2 SOCF Et HIH F 0 3 3 2 3 SOCF Et HHH SMe 0 SOCF Et HIH F 1 SOCF Et HHH SMe 1 SOCF Et HIH F 2 SOCF Et HHH SMe 2 SOCF Et HIH Cl 0 SOCF Et HHH SOMe 0 SOCF Et HIH Cl 1 SOCF Et HHH SOMe 1 SOCF Et HIH Cl 2 SOCF Et HHH SOMe 2 SOCF Et HIH Br 0 SOCF Et HHH SO Me 0 SOCF Et HIH Br 1 3 2 3 SOCF Et HHH SO Me 1 SOCF Et HIH Br 2 3 2 3 SOCF Et HHH SO Me 2 SOCF Et HFH CN 0 3 2 3 SOCF Et HHH OMe 0 SOCF Et HFH CN 1 SOCF Et HHH OMe 1 SOCF Et HFH CN 2 SOCF Et HHH OMe 2 SOCF Et HClH CN 0 SOCF Et HHH OCF 0 SOCF Et HClH CN 1 3 3 3 SOCF Et HHH OCF 1 SOCF Et HClH CN 2 3 3 3 SOCF Et HHH OCF 2 SOCF Et HBrH CN 0 3 3 3 SOCF Et HHH NO 0 SOCF Et HBrH CN 1 3 2 3 SOCF Et HHH NO 1 SOCF Et HBrH CN 2 3 2 3 SOCF Et HHH NO 2 SOCF Et HIH CN 0 3 2 3 SOCF Et HHH CN 0 SOCF Et HIH CN 1 SOCF Et HHH CN 1 SOCF Et HIH CN 2 SOCF Et HHH CN 2 SOCF Et HCF HF 0 3 3 3 SOCF Et HFH F 0 SOCF Et HCF HF 1 3 3 3 SOCF Et HFH F 1 SOCF Et HCF HF 2 3 3 3 SOCF Et HFH F 2 SOCF Et HCF HCl 0 3 3 3 SOCF Et HClH Cl 0 SOCF Et HCF HCl 1 3 3 3 SOCF Et HClH Cl 1 SOCF Et HCF HCl 2 3 3 3 SOCF Et HClH Cl 2 SOCF Et HCF HBr 0 3 3 3 SOCF Et HBrH Br 0 SOCF Et HCF HBr 1 3 3 3 SOCF Et HBrH Br 1 SOCF Et HCF HBr 2 3 3 3 SOCF Et HBrH Br 2 SOCF Et HCF HI 0 3 3 3 SOCF Et HIH I 0 SOCF Et HCF HI 1 3 3 3 SOCF Et HIH I 1 SOCF Et HCF HI 2 3 3 3 SOCF Et HIH I 2 SOCF Et HCF HCN 0 3 3 3 SOCF Et HFH Cl 0 SOCF Et HCF HCN 1 3 3 3 SOCF Et HFH Cl 1 SOCF Et HCF HCN 2 3 3 3 SOCF Et HFH Cl 2 SOCF Et HFF H 0 SOCF Et HFH Br 0 SOCF Et HFF H 1 SOCF Et HFH Br 1 SOCF Et HFF H 2 SOCF Et HFH Br 2 SOCF Et HCl Cl H 0 SOCF Et HFH I 0 SOCF Et HCl Cl H 1 SOCF Et HFH I 1 SOCF Et HCl Cl H 2 SOCF Et HFH I 2 SOCF Et HBr Br H 0 SOCF Et HClH F 0 SOCF Et HBr Br H 1 SOCF Et HClH F 1 SOCF Et HBr Br H 2 SOCF Et HClH F 2 SOCF Et HII H 0 SOCF Et HClH Br 0 SOCF Et HII H 1 SOCF Et HClH Br 1 SOCF Et HII H 2 SOCF Et HClH Br 2 SOCF Et HF Cl H 0 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Et HF Cl H 1 SOCF Pr HHH H 0 SOCF Et HF Cl H 2 SOCF HHH H 1 SOCF Et HF Br H 0 SOCF Pr HHH H 2 SOCF Et HF Br H 1 SOCF FHH H 0 SOCF Et HF Br H 2 SOCF Pr FHH H 1 SOCF Et HFI H 0 SOCF FHH H 2 SOCF Et HFI H 1 SOCF Pr Cl H H H 0 SOCF Et HFI H 2 SOCF Pr Cl H H H 1 SOCF Et HClF H 0 SOCF Pr Cl H H H 2 SOCF Et HClF H 1 SOCF Pr Br H H H 0 SOCF Et HClF H 2 SOCF Br H H H 1 SOCF Et HCl Br H 0 SOCF Pr Br H H H 2 SOCF Et HCl Br H 1 SOCF IHH H 0 SOCF Et HCl Br H 2 SOCF Pr IHH H 1 SOCF Et HClI H 0 SOCF IHH H 2 SOCF Et HClI H 1 SOCF Pr Me H H H 0 SOCF Et HClI H 2 SOCF Pr Me H H H 1 SOCF Et HBrF H 0 SOCF Pr Me H H H 2 SOCF Et HBrF H 1 SOCF Pr CF HH H 0 3 3 3 SOCF Et HBrF H 2 SOCF CF HH H 1 3 3 3 SOCF Et HBr Cl H 0 SOCF Pr CF HH H 2 3 3 3 SOCF Et HBr Cl H 1 SOCF HFH H 0 SOCF Et HBr Cl H 2 SOCF Pr HFH H 1 SOCF Et HBrI H 0 SOCF HFH H 2 SOCF Et HBrI H 1 SOCF Pr HClH H 0 SOCF Et HBrI H 2 SOCF HClH H 1 SOCF Et HIF H 0 SOCF Pr HClH H 2 SOCF Et HIF H 1 SOCF Pr HBrH H 0 SOCF Et HIF H 2 SOCF Pr HBrH H 1 SOCF Et HI Cl H 0 SOCF Pr HBrH H 2 SOCF Et HI Cl H 1 SOCF HIH H 0 SOCF Et HI Cl H 2 SOCF Pr HIH H 1 SOCF Et HI Br H 0 SOCF HIH H 2 SOCF Et HI Br H 1 SOCF Pr HMeH H 0 SOCF Et HI Br H 2 SOCF HMeH H 1 SOCF Et HF CN H 0 SOCF Pr HMeH H 2 SOCF Et HF CN H 1 SOCF Pr HCF HH 0 3 3 3 SOCF Et HF CN H 2 SOCF Pr HCF HH 1 3 3 3 SOCF Et HCl CN H 0 SOCF Pr HCF HH 2 3 3 3 SOCF Et HCl CN H 1 SOCF HCF CF HH 0 3 3 2 3 SOCF Et HCl CN H 2 SOCF Pr HCF CF HH 1 3 3 2 3 SOCF Et HBr CN H 0 SOCF HCF CF HH 2 3 3 2 3 SOCF Et HBr CN H 1 SOCF Pr H CF(CF ) HH 0 3 3 3 2 SOCF Et HBr CN H 2 SOCF H CF(CF ) HH 1 3 3 3 2 SOCF Et HI CN H 0 SOCF Pr H CF(CF ) HH 2 3 3 3 2 SOCF Et HI CN H 1 SOCF H SMe H H 0 SOCF Et HI CN H 2 SOCF Pr H SMe H H 1 SOCF Et HCF FH 0 SOCF H SMe H H 2 3 3 3 SOCF Et HCF FH 1 SOCF Pr HSOMeH H 0 3 3 3 SOCF Et HCF FH 2 SOCF Pr HSOMeH H 1 3 3 3 SOCF Et HCF Cl H 0 SOCF HSOMeH H 2 3 3 3 SOCF Et HCF Cl H 1 SOCF Pr HSO Me H H 0 3 3 3 2 SOCF Et HCF Cl H 2 SOCF HSO Me H H 1 3 3 3 2 SOCF Et HCF Br H 0 SOCF Pr HSO Me H H 2 3 3 3 2 SOCF Et HCF Br H 1 SOCF H OMe H H 0 3 3 3 SOCF Et HCF Br H 2 SOCF Pr H OMe H H 1 3 3 3 SOCF Et HCF IH 0 SOCF Pr H OMe H H 2 3 3 3 SOCF Et HCF IH 1 SOCF Pr HOCF HH 0 3 3 3 3 SOCF Et HCF IH 2 SOCF Pr HOCF HH 1 3 3 3 3 SOCF Et HCF CN H 0 SOCF Pr HOCF HH 2 3 3 3 3 SOCF Et HCF CN H 1 SOCF Pr HNO HH 0 3 3 3 2 SOCF Et HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Pr HNO HH 1 SOCF Pr HHH I 2 3 2 3 SOCF HNO HH 2 SOCF HHH Me 0 Pr Pr 3 2 3 SOCF Pr HCNH H 0 SOCF Pr HHH Me 1 SOCF HCNH H 1 SOCF HHH Me 2 Pr Pr SOCF Pr HCNH H 2 SOCF Pr HHH CF 0 3 3 3 SOCF Pr HHF H 0 SOCF Pr HHH CF 1 3 3 3 SOCF Pr HHF H 1 SOCF Pr HHH CF 2 3 3 3 SOCF Pr HHF H 2 SOCF Pr HHH CF CF 0 3 3 2 3 SOCF HH Cl H 0 SOCF HHH CF CF 1 Pr Pr 3 3 2 3 SOCF Pr HH Cl H 1 SOCF Pr HHH CF CF 2 3 3 2 3 SOCF HH Cl H 2 SOCF H H H CF(CF ) 0 Pr Pr 3 3 3 2 SOCF Pr HH Br H 0 SOCF Pr H H H CF(CF ) 1 3 3 3 2 SOCF HH Br H 1 SOCF H H H CF(CF ) 2 Pr Pr 3 3 3 2 SOCF Pr HH Br H 2 SOCF Pr HHH SMe 0 SOCF HHI H 0 SOCF HHH SMe 1 Pr Pr SOCF Pr HHI H 1 SOCF Pr HHH SMe 2 SOCF Pr HHI H 2 SOCF Pr HHH SOMe 0 SOCF HH Me H 0 SOCF HHH SOMe 1 Pr Pr SOCF Pr HH Me H 1 SOCF Pr HHH SOMe 2 SOCF HH Me H 2 SOCF HHH SO Me 0 Pr Pr 3 3 2 SOCF Pr HH CF H 0 SOCF Pr HHH SO Me 1 3 3 3 2 SOCF HH CF H 1 SOCF HHH SO Me 2 Pr Pr 3 3 3 2 SOCF Pr HH CF H 2 SOCF Pr HHH OMe 0 3 3 3 SOCF Pr HH CF CF H 0 SOCF Pr HHH OMe 1 3 2 3 3 SOCF Pr HH CF CF H 1 SOCF Pr HHH OMe 2 3 2 3 3 SOCF Pr HH CF CF H 2 SOCF Pr HHH OCF 0 3 2 3 3 3 SOCF H H CF(CF ) H 0 SOCF HHH OCF 1 Pr Pr 3 3 2 3 3 SOCF Pr H H CF(CF ) H 1 SOCF Pr HHH OCF 2 3 3 2 3 3 SOCF H H CF(CF ) H 2 SOCF HHH NO 0 Pr Pr 3 3 2 3 2 SOCF Pr HH SMe H 0 SOCF Pr HHH NO 1 3 3 2 SOCF HH SMe H 1 SOCF HHH NO 2 Pr Pr 3 3 2 SOCF Pr HH SMe H 2 SOCF Pr HHH CN 0 SOCF Pr H H SOMe H 0 SOCF Pr HHH CN 1 SOCF Pr H H SOMe H 1 SOCF Pr HHH CN 2 SOCF Pr H H SOMe H 2 SOCF Pr HFH F 0 SOCF HH SO Me H 0 SOCF HFH F 1 Pr Pr 3 2 3 SOCF Pr HH SO Me H 1 SOCF Pr HFH F 2 3 2 3 SOCF HH SO Me H 2 SOCF HClH Cl 0 Pr Pr 3 2 3 SOCF Pr HH OMe H 0 SOCF Pr HClH Cl 1 SOCF HH OMe H 1 SOCF HClH Cl 2 Pr Pr SOCF Pr HH OMe H 2 SOCF Pr HBrH Br 0 SOCF H H OCF H 0 SOCF HBrH Br 1 Pr Pr 3 3 3 SOCF Pr H H OCF H 1 SOCF Pr HBrH Br 2 3 3 3 SOCF Pr H H OCF H 2 SOCF Pr HIH I 0 3 3 3 SOCF HH NO H 0 SOCF HIH I 1 Pr Pr 3 2 3 SOCF Pr HH NO H 1 SOCF Pr HIH I 2 3 2 3 SOCF HH NO H 2 SOCF HFH Cl 0 Pr Pr 3 2 3 SOCF Pr HH CN H 0 SOCF Pr HFH Cl 1 SOCF HH CN H 1 SOCF HFH Cl 2 Pr Pr SOCF Pr HH CN H 2 SOCF Pr HFH Br 0 SOCF Pr HHH F 0 SOCF Pr HFH Br 1 SOCF Pr HHH F 1 SOCF Pr HFH Br 2 SOCF Pr HHH F 2 SOCF Pr HFH I 0 SOCF HHH Cl 0 SOCF HFH I 1 Pr Pr SOCF Pr HHH Cl 1 SOCF Pr HFH I 2 SOCF HHH Cl 2 SOCF HClH F 0 Pr Pr SOCF Pr HHH Br 0 SOCF Pr HClH F 1 SOCF HHH Br 1 SOCF HClH F 2 Pr Pr SOCF Pr HHH Br 2 SOCF Pr HClH Br 0 SOCF HHH I 0 SOCF HClH Br 1 Pr Pr SOCF Pr HHH I 1 SOCF Pr HClH Br 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Pr HClH I 0 SOCF Pr HF Cl H 1 SOCF HClH I 1 SOCF HF Cl H 2 Pr Pr SOCF Pr HClH I 2 SOCF Pr HF Br H 0 SOCF HBrH F 0 SOCF HF Br H 1 Pr Pr SOCF Pr HBrH F 1 SOCF Pr HF Br H 2 SOCF HBrH F 2 SOCF HFI H 0 Pr Pr SOCF Pr HBrH Cl 0 SOCF Pr HFI H 1 SOCF Pr HBrH Cl 1 SOCF Pr HFI H 2 SOCF Pr HBrH Cl 2 SOCF Pr HClF H 0 SOCF Pr HBrH I 0 SOCF Pr HClF H 1 SOCF HBrH I 1 SOCF HClF H 2 Pr Pr SOCF Pr HBrH I 2 SOCF Pr HCl Br H 0 SOCF HIH F 0 SOCF HCl Br H 1 Pr Pr SOCF Pr HIH F 1 SOCF Pr HCl Br H 2 SOCF HIH F 2 SOCF HClI H 0 Pr Pr SOCF Pr HIH Cl 0 SOCF Pr HClI H 1 SOCF Pr HIH Cl 1 SOCF Pr HClI H 2 SOCF Pr HIH Cl 2 SOCF Pr HBrF H 0 SOCF Pr HIH Br 0 SOCF Pr HBrF H 1 SOCF HIH Br 1 SOCF HBrF H 2 Pr Pr SOCF Pr HIH Br 2 SOCF Pr HBr Cl H 0 SOCF HFH CN 0 SOCF HBr Cl H 1 Pr Pr SOCF Pr HFH CN 1 SOCF Pr HBr Cl H 2 SOCF HFH CN 2 SOCF HBrI H 0 Pr Pr SOCF Pr HClH CN 0 SOCF Pr HBrI H 1 SOCF HClH CN 1 SOCF HBrI H 2 Pr Pr SOCF Pr HClH CN 2 SOCF Pr HIF H 0 SOCF Pr HBrH CN 0 SOCF Pr HIF H 1 SOCF Pr HBrH CN 1 SOCF Pr HIF H 2 SOCF Pr HBrH CN 2 SOCF Pr HI Cl H 0 SOCF HIH CN 0 SOCF HI Cl H 1 Pr Pr SOCF Pr HIH CN 1 SOCF Pr HI Cl H 2 SOCF HIH CN 2 SOCF HI Br H 0 Pr Pr SOCF Pr HCF HF 0 SOCF Pr HI Br H 1 3 3 3 SOCF HCF HF 1 SOCF HI Br H 2 Pr Pr 3 3 3 SOCF Pr HCF HF 2 SOCF Pr HF CN H 0 3 3 3 SOCF Pr HCF HCl 0 SOCF Pr HF CN H 1 3 3 3 SOCF Pr HCF HCl 1 SOCF Pr HF CN H 2 3 3 3 SOCF Pr HCF HCl 2 SOCF Pr HCl CN H 0 3 3 3 SOCF HCF HBr 0 SOCF HCl CN H 1 Pr Pr 3 3 3 SOCF Pr HCF HBr 1 SOCF Pr HCl CN H 2 3 3 3 SOCF HCF HBr 2 SOCF HBr CN H 0 Pr Pr 3 3 3 SOCF Pr HCF HI 0 SOCF Pr HBr CN H 1 3 3 3 SOCF HCF HI 1 SOCF HBr CN H 2 Pr Pr 3 3 3 SOCF Pr HCF HI 2 SOCF Pr HI CN H 0 3 3 3 SOCF HCF HCN 0 SOCF HI CN H 1 Pr Pr 3 3 3 SOCF Pr HCF HCN 1 SOCF Pr HI CN H 2 3 3 3 SOCF HCF HCN 2 SOCF HCF FH 0 Pr Pr 3 3 3 3 SOCF Pr HFF H 0 SOCF Pr HCF FH 1 3 3 3 SOCF Pr HFF H 1 SOCF Pr HCF FH 2 3 3 3 SOCF HFF H 2 SOCF HCF Cl H 0 Pr Pr 3 3 3 SOCF Pr HCl Cl H 0 SOCF Pr HCF Cl H 1 3 3 3 SOCF HCl Cl H 1 SOCF HCF Cl H 2 Pr Pr 3 3 3 SOCF Pr HCl Cl H 2 SOCF Pr HCF Br H 0 3 3 3 SOCF HBr Br H 0 SOCF HCF Br H 1 Pr Pr 3 3 3 SOCF Pr HBr Br H 1 SOCF Pr HCF Br H 2 3 3 3 SOCF Pr HBr Br H 2 SOCF Pr HCF IH 0 3 3 3 SOCF Pr HII H 0 SOCF Pr HCF IH 1 3 3 3 SOCF Pr HII H 1 SOCF Pr HCF IH 2 3 3 3 SOCF Pr HII H 2 SOCF Pr HCF CN H 0 3 3 3 SOCF Pr HF Cl H 0 SOCF Pr HCF CN H 1 3 3 3 SOCF HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Pr HHH H 0 SOCF Pr HNO HH 1 3 3 2 SOCF HHH H 1 SOCF HNO HH 2 Pr Pr 3 3 2 SOCF Pr HHH H 2 SOCF Pr HCNH H 0 SOCF FHH H 0 SOCF HCNH H 1 Pr Pr SOCF Pr FHH H 1 SOCF Pr HCNH H 2 SOCF Pr FHH H 2 SOCF Pr HHF H 0 SOCF Pr Cl H H H 0 SOCF Pr HHF H 1 SOCF Pr Cl H H H 1 SOCF Pr HHF H 2 SOCF Cl H H H 2 SOCF HH Cl H 0 Pr Pr SOCF Pr Br H H H 0 SOCF Pr HH Cl H 1 SOCF Br H H H 1 SOCF HH Cl H 2 Pr Pr SOCF Pr Br H H H 2 SOCF Pr HH Br H 0 SOCF IHH H 0 SOCF HH Br H 1 Pr Pr SOCF Pr IHH H 1 SOCF Pr HH Br H 2 SOCF IHH H 2 SOCF HHI H 0 Pr Pr SOCF Pr Me H H H 0 SOCF Pr HHI H 1 SOCF Pr Me H H H 1 SOCF Pr HHI H 2 SOCF Me H H H 2 SOCF HH Me H 0 Pr Pr SOCF Pr CF HH H 0 SOCF Pr HH Me H 1 3 3 3 SOCF CF HH H 1 SOCF HH Me H 2 Pr Pr 3 3 3 SOCF Pr CF HH H 2 SOCF Pr HH CF H 0 3 3 3 3 SOCF HFH H 0 SOCF HH CF H 1 Pr Pr 3 3 3 SOCF Pr HFH H 1 SOCF Pr HH CF H 2 3 3 3 SOCF Pr HFH H 2 SOCF Pr HH CF CF H 0 3 3 2 3 SOCF Pr HClH H 0 SOCF Pr HH CF CF H 1 3 3 2 3 SOCF Pr HClH H 1 SOCF Pr HH CF CF H 2 3 3 2 3 SOCF HClH H 2 SOCF H H CF(CF ) H 0 Pr Pr 3 3 3 2 SOCF Pr HBrH H 0 SOCF Pr H H CF(CF ) H 1 3 3 3 2 SOCF HBrH H 1 SOCF H H CF(CF ) H 2 Pr Pr 3 3 3 2 SOCF Pr HBrH H 2 SOCF Pr HH SMe H 0 SOCF HIH H 0 SOCF HH SMe H 1 Pr Pr SOCF Pr HIH H 1 SOCF Pr HH SMe H 2 SOCF Pr HIH H 2 SOCF Pr H H SOMe H 0 SOCF Pr HMeH H 0 SOCF Pr H H SOMe H 1 SOCF Pr HMeH H 1 SOCF Pr H H SOMe H 2 SOCF HMeH H 2 SOCF HH SO Me H 0 Pr Pr 3 3 2 SOCF Pr HCF HH 0 SOCF Pr HH SO Me H 1 3 3 3 2 SOCF HCF HH 1 SOCF HH SO Me H 2 Pr Pr 3 3 3 2 SOCF Pr HCF HH 2 SOCF Pr HH OMe H 0 3 3 3 SOCF HCF CF HH 0 SOCF HH OMe H 1 Pr Pr 3 2 3 3 SOCF Pr HCF CF HH 1 SOCF Pr HH OMe H 2 3 2 3 3 SOCF HCF CF HH 2 SOCF H H OCF H 0 Pr Pr 3 2 3 3 3 SOCF Pr H CF(CF ) HH 0 SOCF Pr H H OCF H 1 3 3 2 3 3 SOCF Pr H CF(CF ) HH 1 SOCF Pr H H OCF H 2 3 3 2 3 3 SOCF H CF(CF ) HH 2 SOCF HH NO H 0 Pr Pr 3 3 2 3 2 SOCF Pr H SMe H H 0 SOCF Pr HH NO H 1 3 3 2 SOCF H SMe H H 1 SOCF HH NO H 2 Pr Pr 3 3 2 SOCF Pr H SMe H H 2 SOCF Pr HH CN H 0 SOCF HSOMeH H 0 SOCF HH CN H 1 Pr Pr SOCF Pr HSOMeH H 1 SOCF Pr HH CN H 2 SOCF Pr HSOMeH H 2 SOCF Pr HHH F 0 SOCF Pr HSO Me H H 0 SOCF Pr HHH F 1 3 2 3 SOCF Pr HSO Me H H 1 SOCF Pr HHH F 2 3 2 3 SOCF HSO Me H H 2 SOCF HHH Cl 0 Pr Pr 3 2 3 SOCF Pr H OMe H H 0 SOCF Pr HHH Cl 1 SOCF H OMe H H 1 SOCF HHH Cl 2 Pr Pr SOCF Pr H OMe H H 2 SOCF Pr HHH Br 0 SOCF HOCF HH 0 SOCF HHH Br 1 Pr Pr 3 3 3 SOCF Pr HOCF HH 1 SOCF Pr HHH Br 2 3 3 3 SOCF HOCF HH 2 SOCF HHH I 0 Pr Pr 3 3 3 SOCF Pr HNO HH 0 SOCF Pr HHH I 1 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Pr HHH I 2 SOCF Pr HClH I 0 SOCF HHH Me 0 SOCF HClH I 1 Pr Pr SOCF Pr HHH Me 1 SOCF Pr HClH I 2 SOCF HHH Me 2 SOCF HBrH F 0 Pr Pr SOCF Pr HHH CF 0 SOCF Pr HBrH F 1 3 3 3 SOCF Pr HHH CF 1 SOCF Pr HBrH F 2 3 3 3 SOCF Pr HHH CF 2 SOCF Pr HBrH Cl 0 3 3 3 SOCF Pr HHH CF CF 0 SOCF Pr HBrH Cl 1 3 2 3 3 SOCF HHH CF CF 1 SOCF HBrH Cl 2 Pr Pr 3 2 3 3 SOCF Pr HHH CF CF 2 SOCF Pr HBrH I 0 3 2 3 3 SOCF H H H CF(CF ) 0 SOCF HBrH I 1 Pr Pr 3 3 2 3 SOCF Pr H H H CF(CF ) 1 SOCF Pr HBrH I 2 3 3 2 3 SOCF H H H CF(CF ) 2 SOCF HIH F 0 Pr Pr 3 3 2 3 SOCF Pr HHH SMe 0 SOCF Pr HIH F 1 SOCF HHH SMe 1 SOCF HIH F 2 Pr Pr SOCF Pr HHH SMe 2 SOCF Pr HIH Cl 0 SOCF Pr HHH SOMe 0 SOCF Pr HIH Cl 1 SOCF HHH SOMe 1 SOCF HIH Cl 2 Pr Pr SOCF Pr HHH SOMe 2 SOCF Pr HIH Br 0 SOCF HHH SO Me 0 SOCF HIH Br 1 Pr Pr 3 2 3 SOCF Pr HHH SO Me 1 SOCF Pr HIH Br 2 3 2 3 SOCF HHH SO Me 2 SOCF HFH CN 0 Pr Pr 3 2 3 SOCF Pr HHH OMe 0 SOCF Pr HFH CN 1 SOCF Pr HHH OMe 1 SOCF Pr HFH CN 2 SOCF Pr HHH OMe 2 SOCF Pr HClH CN 0 SOCF Pr HHH OCF 0 SOCF Pr HClH CN 1 3 3 3 SOCF HHH OCF 1 SOCF HClH CN 2 Pr Pr 3 3 3 SOCF Pr HHH OCF 2 SOCF Pr HBrH CN 0 3 3 3 SOCF HHH NO 0 SOCF HBrH CN 1 Pr Pr 3 2 3 SOCF Pr HHH NO 1 SOCF Pr HBrH CN 2 3 2 3 SOCF HHH NO 2 SOCF HIH CN 0 Pr Pr 3 2 3 SOCF Pr HHH CN 0 SOCF Pr HIH CN 1 SOCF Pr HHH CN 1 SOCF Pr HIH CN 2 SOCF Pr HHH CN 2 SOCF Pr HCF HF 0 3 3 3 SOCF Pr HFH F 0 SOCF Pr HCF HF 1 3 3 3 SOCF HFH F 1 SOCF HCF HF 2 Pr Pr 3 3 3 SOCF Pr HFH F 2 SOCF Pr HCF HCl 0 3 3 3 SOCF HClH Cl 0 SOCF HCF HCl 1 Pr Pr 3 3 3 SOCF Pr HClH Cl 1 SOCF Pr HCF HCl 2 3 3 3 SOCF HClH Cl 2 SOCF HCF HBr 0 Pr Pr 3 3 3 SOCF Pr HBrH Br 0 SOCF Pr HCF HBr 1 3 3 3 SOCF HBrH Br 1 SOCF HCF HBr 2 Pr Pr 3 3 3 SOCF Pr HBrH Br 2 SOCF Pr HCF HI 0 3 3 3 SOCF Pr HIH I 0 SOCF Pr HCF HI 1 3 3 3 SOCF HIH I 1 SOCF HCF HI 2 Pr Pr 3 3 3 SOCF Pr HIH I 2 SOCF Pr HCF HCN 0 3 3 3 SOCF HFH Cl 0 SOCF HCF HCN 1 Pr Pr 3 3 3 SOCF Pr HFH Cl 1 SOCF Pr HCF HCN 2 3 3 3 SOCF HFH Cl 2 SOCF HFF H 0 Pr Pr SOCF Pr HFH Br 0 SOCF Pr HFF H 1 SOCF Pr HFH Br 1 SOCF Pr HFF H 2 SOCF Pr HFH Br 2 SOCF Pr HCl Cl H 0 SOCF Pr HFH I 0 SOCF Pr HCl Cl H 1 SOCF HFH I 1 SOCF HCl Cl H 2 Pr Pr SOCF Pr HFH I 2 SOCF Pr HBr Br H 0 SOCF HClH F 0 SOCF HBr Br H 1 Pr Pr SOCF Pr HClH F 1 SOCF Pr HBr Br H 2 SOCF HClH F 2 SOCF HII H 0 Pr Pr SOCF Pr HClH Br 0 SOCF Pr HII H 1 SOCF HClH Br 1 SOCF HII H 2 Pr Pr SOCF Pr HClH Br 2 SOCF Pr HF Cl H 0 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF Pr HF Cl H 1 SOCF CH CF HHH H 0 3 3 2 3 SOCF HF Cl H 2 SOCF CH CF HHH H 1 3 3 2 3 SOCF Pr HF Br H 0 SOCF CH CF HHH H 2 3 3 2 3 SOCF HF Br H 1 SOCF CH CF FHH H 0 3 3 2 3 SOCF Pr HF Br H 2 SOCF CH CF FHH H 1 3 3 2 3 SOCF HFI H 0 SOCF CH CF FHH H 2 3 3 2 3 SOCF Pr HFI H 1 SOCF CH CF Cl H H H 0 3 3 2 3 SOCF Pr HFI H 2 SOCF CH CF Cl H H H 1 3 3 2 3 SOCF Pr HClF H 0 SOCF CH CF Cl H H H 2 3 3 2 3 SOCF Pr HClF H 1 SOCF CH CF Br H H H 0 3 3 2 3 SOCF HClF H 2 SOCF CH CF Br H H H 1 3 3 2 3 SOCF Pr HCl Br H 0 SOCF CH CF Br H H H 2 3 3 2 3 SOCF HCl Br H 1 SOCF CH CF IHH H 0 3 3 2 3 SOCF Pr HCl Br H 2 SOCF CH CF IHH H 1 3 3 2 3 SOCF HClI H 0 SOCF CH CF IHH H 2 3 3 2 3 SOCF Pr HClI H 1 SOCF CH CF Me H H H 0 3 3 2 3 SOCF Pr HClI H 2 SOCF CH CF Me H H H 1 3 3 2 3 SOCF Pr HBrF H 0 SOCF CH CF Me H H H 2 3 3 2 3 SOCF Pr HBrF H 1 SOCF CH CF CF HH H 0 3 3 2 3 3 SOCF HBrF H 2 SOCF CH CF CF HH H 1 3 3 2 3 3 SOCF Pr HBr Cl H 0 SOCF CH CF CF HH H 2 3 3 2 3 3 SOCF HBr Cl H 1 SOCF CH CF HFH H 0 3 3 2 3 SOCF Pr HBr Cl H 2 SOCF CH CF HFH H 1 3 3 2 3 SOCF HBrI H 0 SOCF CH CF HFH H 2 3 3 2 3 SOCF Pr HBrI H 1 SOCF CH CF HClH H 0 3 3 2 3 SOCF HBrI H 2 SOCF CH CF HClH H 1 3 3 2 3 SOCF Pr HIF H 0 SOCF CH CF HClH H 2 3 3 2 3 SOCF Pr HIF H 1 SOCF CH CF HBrH H 0 3 3 2 3 SOCF Pr HIF H 2 SOCF CH CF HBrH H 1 3 3 2 3 SOCF Pr HI Cl H 0 SOCF CH CF HBrH H 2 3 3 2 3 SOCF HI Cl H 1 SOCF CH CF HIH H 0 3 3 2 3 SOCF Pr HI Cl H 2 SOCF CH CF HIH H 1 3 3 2 3 SOCF HI Br H 0 SOCF CH CF HIH H 2 3 3 2 3 SOCF Pr HI Br H 1 SOCF CH CF HMeH H 0 3 3 2 3 SOCF HI Br H 2 SOCF CH CF HMeH H 1 3 3 2 3 SOCF Pr HF CN H 0 SOCF CH CF HMeH H 2 3 3 2 3 SOCF Pr HF CN H 1 SOCF CH CF HCF HH 0 3 3 2 3 3 SOCF Pr HF CN H 2 SOCF CH CF HCF HH 1 3 3 2 3 3 SOCF Pr HCl CN H 0 SOCF CH CF HCF HH 2 3 3 2 3 3 SOCF HCl CN H 1 SOCF CH CF HCF CF HH 0 3 3 2 3 2 3 SOCF Pr HCl CN H 2 SOCF CH CF HCF CF HH 1 3 3 2 3 2 3 SOCF HBr CN H 0 SOCF CH CF HCF CF HH 2 3 3 2 3 2 3 SOCF Pr HBr CN H 1 SOCF CH CF H CF(CF ) HH 0 3 3 2 3 3 2 SOCF HBr CN H 2 SOCF CH CF H CF(CF ) HH 1 3 3 2 3 3 2 SOCF Pr HI CN H 0 SOCF CH CF H CF(CF ) HH 2 3 3 2 3 3 2 SOCF HI CN H 1 SOCF CH CF H SMe H H 0 3 3 2 3 SOCF Pr HI CN H 2 SOCF CH CF H SMe H H 1 3 3 2 3 SOCF HCF FH 0 SOCF CH CF H SMe H H 2 3 3 3 2 3 SOCF Pr HCF FH 1 SOCF CH CF HSOMeH H 0 3 3 3 2 3 SOCF Pr HCF FH 2 SOCF CH CF HSOMeH H 1 3 3 3 2 3 SOCF HCF Cl H 0 SOCF CH CF HSOMeH H 2 3 3 3 2 3 SOCF Pr HCF Cl H 1 SOCF CH CF HSO Me H H 0 3 3 3 2 3 2 SOCF HCF Cl H 2 SOCF CH CF HSO Me H H 1 3 3 3 2 3 2 SOCF Pr HCF Br H 0 SOCF CH CF HSO Me H H 2 3 3 3 2 3 2 SOCF HCF Br H 1 SOCF CH CF H OMe H H 0 3 3 3 2 3 SOCF Pr HCF Br H 2 SOCF CH CF H OMe H H 1 3 3 3 2 3 SOCF Pr HCF IH 0 SOCF CH CF H OMe H H 2 3 3 3 2 3 SOCF Pr HCF IH 1 SOCF CH CF HOCF HH 0 3 3 3 2 3 3 SOCF Pr HCF IH 2 SOCF CH CF HOCF HH 1 3 3 3 2 3 3 SOCF Pr HCF CN H 0 SOCF CH CF HOCF HH 2 3 3 3 2 3 3 SOCF Pr HCF CN H 1 SOCF CH CF HNO HH 0 3 3 3 2 3 2 SOCF HCF CN H 2 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF CH CF HNO HH 1 SOCF CH CF HHH I 2 3 2 3 2 3 2 3 SOCF CH CF HNO HH 2 SOCF CH CF HHH Me 0 3 2 3 2 3 2 3 SOCF CH CF HCNH H 0 SOCF CH CF HHH Me 1 3 2 3 3 2 3 SOCF CH CF HCNH H 1 SOCF CH CF HHH Me 2 3 2 3 3 2 3 SOCF CH CF HCNH H 2 SOCF CH CF HHH CF 0 3 2 3 3 2 3 3 SOCF CH CF HHF H 0 SOCF CH CF HHH CF 1 3 2 3 3 2 3 3 SOCF CH CF HHF H 1 SOCF CH CF HHH CF 2 3 2 3 3 2 3 3 SOCF CH CF HHF H 2 SOCF CH CF HHH CF CF 0 3 2 3 3 2 3 2 3 SOCF CH CF HH Cl H 0 SOCF CH CF HHH CF CF 1 3 2 3 3 2 3 2 3 SOCF CH CF HH Cl H 1 SOCF CH CF HHH CF CF 2 3 2 3 3 2 3 2 3 SOCF CH CF HH Cl H 2 SOCF CH CF H H H CF(CF ) 0 3 2 3 3 2 3 3 2 SOCF CH CF HH Br H 0 SOCF CH CF H H H CF(CF ) 1 3 2 3 3 2 3 3 2 SOCF CH CF HH Br H 1 SOCF CH CF H H H CF(CF ) 2 3 2 3 3 2 3 3 2 SOCF CH CF HH Br H 2 SOCF CH CF HHH SMe 0 3 2 3 3 2 3 SOCF CH CF HHI H 0 SOCF CH CF HHH SMe 1 3 2 3 3 2 3 SOCF CH CF HHI H 1 SOCF CH CF HHH SMe 2 3 2 3 3 2 3 SOCF CH CF HHI H 2 SOCF CH CF HHH SOMe 0 3 2 3 3 2 3 SOCF CH CF HH Me H 0 SOCF CH CF HHH SOMe 1 3 2 3 3 2 3 SOCF CH CF HH Me H 1 SOCF CH CF HHH SOMe 2 3 2 3 3 2 3 SOCF CH CF HH Me H 2 SOCF CH CF HHH SO Me 0 3 2 3 3 2 3 2 SOCF CH CF HH CF H 0 SOCF CH CF HHH SO Me 1 3 2 3 3 3 2 3 2 SOCF CH CF HH CF H 1 SOCF CH CF HHH SO Me 2 3 2 3 3 3 2 3 2 SOCF CH CF HH CF H 2 SOCF CH CF HHH OMe 0 3 2 3 3 3 2 3 SOCF CH CF HH CF CF H 0 SOCF CH CF HHH OMe 1 3 2 3 2 3 3 2 3 SOCF CH CF HH CF CF H 1 SOCF CH CF HHH OMe 2 3 2 3 2 3 3 2 3 SOCF CH CF HH CF CF H 2 SOCF CH CF HHH OCF 0 3 2 3 2 3 3 2 3 3 SOCF CH CF H H CF(CF ) H 0 SOCF CH CF HHH OCF 1 3 2 3 3 2 3 2 3 3 SOCF CH CF H H CF(CF ) H 1 SOCF CH CF HHH OCF 2 3 2 3 3 2 3 2 3 3 SOCF CH CF H H CF(CF ) H 2 SOCF CH CF HHH NO 0 3 2 3 3 2 3 2 3 2 SOCF CH CF HH SMe H 0 SOCF CH CF HHH NO 1 3 2 3 3 2 3 2 SOCF CH CF HH SMe H 1 SOCF CH CF HHH NO 2 3 2 3 3 2 3 2 SOCF CH CF HH SMe H 2 SOCF CH CF HHH CN 0 3 2 3 3 2 3 SOCF CH CF H H SOMe H 0 SOCF CH CF HHH CN 1 3 2 3 3 2 3 SOCF CH CF H H SOMe H 1 SOCF CH CF HHH CN 2 3 2 3 3 2 3 SOCF CH CF H H SOMe H 2 SOCF CH CF HFH F 0 3 2 3 3 2 3 SOCF CH CF HH SO Me H 0 SOCF CH CF HFH F 1 3 2 3 2 3 2 3 SOCF CH CF HH SO Me H 1 SOCF CH CF HFH F 2 3 2 3 2 3 2 3 SOCF CH CF HH SO Me H 2 SOCF CH CF HClH Cl 0 3 2 3 2 3 2 3 SOCF CH CF HH OMe H 0 SOCF CH CF HClH Cl 1 3 2 3 3 2 3 SOCF CH CF HH OMe H 1 SOCF CH CF HClH Cl 2 3 2 3 3 2 3 SOCF CH CF HH OMe H 2 SOCF CH CF HBrH Br 0 3 2 3 3 2 3 SOCF CH CF H H OCF H 0 SOCF CH CF HBrH Br 1 3 2 3 3 3 2 3 SOCF CH CF H H OCF H 1 SOCF CH CF HBrH Br 2 3 2 3 3 3 2 3 SOCF CH CF H H OCF H 2 SOCF CH CF HIH I 0 3 2 3 3 3 2 3 SOCF CH CF HH NO H 0 SOCF CH CF HIH I 1 3 2 3 2 3 2 3 SOCF CH CF HH NO H 1 SOCF CH CF HIH I 2 3 2 3 2 3 2 3 SOCF CH CF HH NO H 2 SOCF CH CF HFH Cl 0 3 2 3 2 3 2 3 SOCF CH CF HH CN H 0 SOCF CH CF HFH Cl 1 3 2 3 3 2 3 SOCF CH CF HH CN H 1 SOCF CH CF HFH Cl 2 3 2 3 3 2 3 SOCF CH CF HH CN H 2 SOCF CH CF HFH Br 0 3 2 3 3 2 3 SOCF CH CF HHH F 0 SOCF CH CF HFH Br 1 3 2 3 3 2 3 SOCF CH CF HHH F 1 SOCF CH CF HFH Br 2 3 2 3 3 2 3 SOCF CH CF HHH F 2 SOCF CH CF HFH I 0 3 2 3 3 2 3 SOCF CH CF HHH Cl 0 SOCF CH CF HFH I 1 3 2 3 3 2 3 SOCF CH CF HHH Cl 1 SOCF CH CF HFH I 2 3 2 3 3 2 3 SOCF CH CF HHH Cl 2 SOCF CH CF HClH F 0 3 2 3 3 2 3 SOCF CH CF HHH Br 0 SOCF CH CF HClH F 1 3 2 3 3 2 3 SOCF CH CF HHH Br 1 SOCF CH CF HClH F 2 3 2 3 3 2 3 SOCF CH CF HHH Br 2 SOCF CH CF HClH Br 0 3 2 3 3 2 3 SOCF CH CF HHH I 0 SOCF CH CF HClH Br 1 3 2 3 3 2 3 SOCF CH CF HHH I 1 SOCF CH CF HClH Br 2 3 2 3 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y 3 Y 4 n W 1 R Y1 Y2 Y 3 Y 4 n SOCF CH CF HClH I 0 SOCF CH CF HF Cl H 1 3 2 3 3 2 3 SOCF CH CF HClH I 1 SOCF CH CF HF Cl H 2 3 2 3 3 2 3 SOCF CH CF HClH I 2 SOCF CH CF HF Br H 0 3 2 3 3 2 3 SOCF CH CF HBrH F 0 SOCF CH CF HF Br H 1 3 2 3 3 2 3 SOCF CH CF HBrH F 1 SOCF CH CF HF Br H 2 3 2 3 3 2 3 SOCF CH CF HBrH F 2 SOCF CH CF HFI H 0 3 2 3 3 2 3 SOCF CH CF HBrH Cl 0 SOCF CH CF HFI H 1 3 2 3 3 2 3 SOCF CH CF HBrH Cl 1 SOCF CH CF HFI H 2 3 2 3 3 2 3 SOCF CH CF HBrH Cl 2 SOCF CH CF HClF H 0 3 2 3 3 2 3 SOCF CH CF HBrH I 0 SOCF CH CF HClF H 1 3 2 3 3 2 3 SOCF CH CF HBrH I 1 SOCF CH CF HClF H 2 3 2 3 3 2 3 SOCF CH CF HBrH I 2 SOCF CH CF HCl Br H 0 3 2 3 3 2 3 SOCF CH CF HIH F 0 SOCF CH CF HCl Br H 1 3 2 3 3 2 3 SOCF CH CF HIH F 1 SOCF CH CF HCl Br H 2 3 2 3 3 2 3 SOCF CH CF HIH F 2 SOCF CH CF HClI H 0 3 2 3 3 2 3 SOCF CH CF HIH Cl 0 SOCF CH CF HClI H 1 3 2 3 3 2 3 SOCF CH CF HIH Cl 1 SOCF CH CF HClI H 2 3 2 3 3 2 3 SOCF CH CF HIH Cl 2 SOCF CH CF HBrF H 0 3 2 3 3 2 3 SOCF CH CF HIH Br 0 SOCF CH CF HBrF H 1 3 2 3 3 2 3 SOCF CH CF HIH Br 1 SOCF CH CF HBrF H 2 3 2 3 3 2 3 SOCF CH CF HIH Br 2 SOCF CH CF HBr Cl H 0 3 2 3 3 2 3 SOCF CH CF HFH CN 0 SOCF CH CF HBr Cl H 1 3 2 3 3 2 3 SOCF CH CF HFH CN 1 SOCF CH CF HBr Cl H 2 3 2 3 3 2 3 SOCF CH CF HFH CN 2 SOCF CH CF HBrI H 0 3 2 3 3 2 3 SOCF CH CF HClH CN 0 SOCF CH CF HBrI H 1 3 2 3 3 2 3 SOCF CH CF HClH CN 1 SOCF CH CF HBrI H 2 3 2 3 3 2 3 SOCF CH CF HClH CN 2 SOCF CH CF HIF H 0 3 2 3 3 2 3 SOCF CH CF HBrH CN 0 SOCF CH CF HIF H 1 3 2 3 3 2 3 SOCF CH CF HBrH CN 1 SOCF CH CF HIF H 2 3 2 3 3 2 3 SOCF CH CF HBrH CN 2 SOCF CH CF HI Cl H 0 3 2 3 3 2 3 SOCF CH CF HIH CN 0 SOCF CH CF HI Cl H 1 3 2 3 3 2 3 SOCF CH CF HIH CN 1 SOCF CH CF HI Cl H 2 3 2 3 3 2 3 SOCF CH CF HIH CN 2 SOCF CH CF HI Br H 0 3 2 3 3 2 3 SOCF CH CF HCF HF 0 SOCF CH CF HI Br H 1 3 2 3 3 3 2 3 SOCF CH CF HCF HF 1 SOCF CH CF HI Br H 2 3 2 3 3 3 2 3 SOCF CH CF HCF HF 2 SOCF CH CF HF CN H 0 3 2 3 3 3 2 3 SOCF CH CF HCF HCl 0 SOCF CH CF HF CN H 1 3 2 3 3 3 2 3 SOCF CH CF HCF HCl 1 SOCF CH CF HF CN H 2 3 2 3 3 3 2 3 SOCF CH CF HCF HCl 2 SOCF CH CF HCl CN H 0 3 2 3 3 3 2 3 SOCF CH CF HCF HBr 0 SOCF CH CF HCl CN H 1 3 2 3 3 3 2 3 SOCF CH CF HCF HBr 1 SOCF CH CF HCl CN H 2 3 2 3 3 3 2 3 SOCF CH CF HCF HBr 2 SOCF CH CF HBr CN H 0 3 2 3 3 3 2 3 SOCF CH CF HCF HI 0 SOCF CH CF HBr CN H 1 3 2 3 3 3 2 3 SOCF CH CF HCF HI 1 SOCF CH CF HBr CN H 2 3 2 3 3 3 2 3 SOCF CH CF HCF HI 2 SOCF CH CF HI CN H 0 3 2 3 3 3 2 3 SOCF CH CF HCF HCN 0 SOCF CH CF HI CN H 1 3 2 3 3 3 2 3 SOCF CH CF HCF HCN 1 SOCF CH CF HI CN H 2 3 2 3 3 3 2 3 SOCF CH CF HCF HCN 2 SOCF CH CF HCF FH 0 3 2 3 3 3 2 3 3 SOCF CH CF HFF H 0 SOCF CH CF HCF FH 1 3 2 3 3 2 3 3 SOCF CH CF HFF H 1 SOCF CH CF HCF FH 2 3 2 3 3 2 3 3 SOCF CH CF HFF H 2 SOCF CH CF HCF Cl H 0 3 2 3 3 2 3 3 SOCF CH CF HCl Cl H 0 SOCF CH CF HCF Cl H 1 3 2 3 3 2 3 3 SOCF CH CF HCl Cl H 1 SOCF CH CF HCF Cl H 2 3 2 3 3 2 3 3 SOCF CH CF HCl Cl H 2 SOCF CH CF HCF Br H 0 3 2 3 3 2 3 3 SOCF CH CF HBr Br H 0 SOCF CH CF HCF Br H 1 3 2 3 3 2 3 3 SOCF CH CF HBr Br H 1 SOCF CH CF HCF Br H 2 3 2 3 3 2 3 3 SOCF CH CF HBr Br H 2 SOCF CH CF HCF IH 0 3 2 3 3 2 3 3 SOCF CH CF HII H 0 SOCF CH CF HCF IH 1 3 2 3 3 2 3 3 SOCF CH CF HII H 1 SOCF CH CF HCF IH 2 3 2 3 3 2 3 3 SOCF CH CF HII H 2 SOCF CH CF HCF CN H 0 3 2 3 3 2 3 3 SOCF CH CF HF Cl H 0 SOCF CH CF HCF CN H 1 3 2 3 3 2 3 3 SOCF CH CF HCF CN H 2 3 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Me HHHH 0 SO CF Me HNO HH 1 2 3 2 3 2 SO CF Me HHHH 1 SO CF Me HNO HH 2 2 3 2 3 2 SO CF Me HHHH 2 SO CF Me HCNH H 0 2 3 2 3 SO CF Me FHHH 0 SO CF Me HCNH H 1 2 3 2 3 SO CF Me FHHH 1 SO CF Me HCNH H 2 2 3 2 3 SO CF Me FHHH 2 SO CF Me HHFH 0 2 3 2 3 SO CF Me Cl H H H 0 SO CF Me HHFH 1 2 3 2 3 SO CF Me Cl H H H 1 SO CF Me HHFH 2 2 3 2 3 SO CF Me Cl H H H 2 SO CF Me HH Cl H 0 2 3 2 3 SO CF Me Br H H H 0 SO CF Me HH Cl H 1 2 3 2 3 SO CF Me Br H H H 1 SO CF Me HH Cl H 2 2 3 2 3 SO CF Me Br H H H 2 SO CF Me HH Br H 0 2 3 2 3 SO CF Me IHHH 0 SO CF Me HH Br H 1 2 3 2 3 SO CF Me IHHH 1 SO CF Me HH Br H 2 2 3 2 3 SO CF Me IHHH 2 SO CF Me HHIH 0 2 3 2 3 SO CF Me Me H H H 0 SO CF Me HHIH 1 2 3 2 3 SO CF Me Me H H H 1 SO CF Me HHIH 2 2 3 2 3 SO CF Me Me H H H 2 SO CF Me HH Me H 0 2 3 2 3 SO CF Me CF HHH 0 SO CF Me HH Me H 1 2 3 3 2 3 SO CF Me CF HHH 1 SO CF Me HH Me H 2 2 3 3 2 3 SO CF Me CF HHH 2 SO CF Me HH CF H 0 2 3 3 2 3 3 SO CF Me HFHH 0 SO CF Me HH CF H 1 2 3 2 3 3 SO CF Me HFHH 1 SO CF Me HH CF H 2 2 3 2 3 3 SO CF Me HFHH 2 SO CF Me HH CF CF H 0 2 3 2 3 2 3 SO CF Me HCl H H 0 SO CF Me HH CF CF H 1 2 3 2 3 2 3 SO CF Me HCl H H 1 SO CF Me HH CF CF H 2 2 3 2 3 2 3 SO CF Me HCl H H 2 SO CF Me H H CF(CF ) H 0 2 3 2 3 3 2 SO CF Me HBr H H 0 SO CF Me H H CF(CF ) H 1 2 3 2 3 3 2 SO CF Me HBr H H 1 SO CF Me H H CF(CF ) H 2 2 3 2 3 3 2 SO CF Me HBr H H 2 SO CF Me H H SMe H 0 2 3 2 3 SO CF Me HIHH 0 SO CF Me H H SMe H 1 2 3 2 3 SO CF Me HIHH 1 SO CF Me H H SMe H 2 2 3 2 3 SO CF Me HIHH 2 SO CF Me H H SOMe H 0 2 3 2 3 SO CF Me HMe H H 0 SO CF Me H H SOMe H 1 2 3 2 3 SO CF Me HMe H H 1 SO CF Me H H SOMe H 2 2 3 2 3 SO CF Me HMe H H 2 SO CF Me HH SO Me H 0 2 3 2 3 2 SO CF Me HCF HH 0 SO CF Me HH SO Me H 1 2 3 3 2 3 2 SO CF Me HCF HH 1 SO CF Me HH SO Me H 2 2 3 3 2 3 2 SO CF Me HCF HH 2 SO CF Me H H OMe H 0 2 3 3 2 3 SO CF Me HCF CF HH 0 SO CF Me H H OMe H 1 2 3 2 3 2 3 SO CF Me HCF CF HH 1 SO CF Me H H OMe H 2 2 3 2 3 2 3 SO CF Me HCF CF HH 2 SO CF Me HH OCF H 0 2 3 2 3 2 3 3 SO CF Me H CF(CF ) HH 0 SO CF Me HH OCF H 1 2 3 3 2 2 3 3 SO CF Me H CF(CF ) HH 1 SO CF Me HH OCF H 2 2 3 3 2 2 3 3 SO CF Me H CF(CF ) HH 2 SO CF Me HH NO H 0 2 3 3 2 2 3 2 SO CF Me HSMe H H 0 SO CF Me HH NO H 1 2 3 2 3 2 SO CF Me HSMe H H 1 SO CF Me HH NO H 2 2 3 2 3 2 SO CF Me HSMe H H 2 SO CF Me HH CN H 0 2 3 2 3 SO CF Me H SOMe H H 0 SO CF Me HH CN H 1 2 3 2 3 SO CF Me H SOMe H H 1 SO CF Me HH CN H 2 2 3 2 3 SO CF Me H SOMe H H 2 SO CF Me HHHF 0 2 3 2 3 SO CF Me HSO Me H H 0 SO CF Me HHHF 1 2 3 2 2 3 SO CF Me HSO Me H H 1 SO CF Me HHHF 2 2 3 2 2 3 SO CF Me HSO Me H H 2 SO CF Me HHH Cl 0 2 3 2 2 3 SO CF Me HOMe H H 0 SO CF Me HHH Cl 1 2 3 2 3 SO CF Me HOMe H H 1 SO CF Me HHH Cl 2 2 3 2 3 SO CF Me HOMe H H 2 SO CF Me HHH Br 0 2 3 2 3 SO CF Me H OCF HH 0 SO CF Me HHH Br 1 2 3 3 2 3 SO CF Me H OCF HH 1 SO CF Me HHH Br 2 2 3 3 2 3 SO CF Me H OCF HH 2 SO CF Me HHHI 0 2 3 3 2 3 SO CF Me HNO HH 0 SO CF Me HHHI 1 2 3 2 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Me HHH I 2 SO CF Me HClH I 0 2 3 2 3 SO CF Me HHH Me 0 SO CF Me HClH I 1 2 3 2 3 SO CF Me HHH Me 1 SO CF Me HClH I 2 2 3 2 3 SO CF Me HHH Me 2 SO CF Me HBrH F 0 2 3 2 3 SO CF Me HHH CF 0 SO CF Me HBrH F 1 2 3 3 2 3 SO CF Me HHH CF 1 SO CF Me HBrH F 2 2 3 3 2 3 SO CF Me HHH CF 2 SO CF Me HBrH Cl 0 2 3 3 2 3 SO CF Me HHH CF CF 0 SO CF Me HBrH Cl 1 2 3 2 3 2 3 SO CF Me HHH CF CF 1 SO CF Me HBrH Cl 2 2 3 2 3 2 3 SO CF Me HHH CF CF 2 SO CF Me HBrH I 0 2 3 2 3 2 3 SO CF Me H H H CF(CF ) 0 SO CF Me HBrH I 1 2 3 3 2 2 3 SO CF Me H H H CF(CF ) 1 SO CF Me HBrH I 2 2 3 3 2 2 3 SO CF Me H H H CF(CF ) 2 SO CF Me HIH F 0 2 3 3 2 2 3 SO CF Me HHH SMe 0 SO CF Me HIH F 1 2 3 2 3 SO CF Me HHH SMe 1 SO CF Me HIH F 2 2 3 2 3 SO CF Me HHH SMe 2 SO CF Me HIH Cl 0 2 3 2 3 SO CF Me HHH SOMe 0 SO CF Me HIH Cl 1 2 3 2 3 SO CF Me HHH SOMe 1 SO CF Me HIH Cl 2 2 3 2 3 SO CF Me HHH SOMe 2 SO CF Me HIH Br 0 2 3 2 3 SO CF Me HHH SO Me 0 SO CF Me HIH Br 1 2 3 2 2 3 SO CF Me HHH SO Me 1 SO CF Me HIH Br 2 2 3 2 2 3 SO CF Me HHH SO Me 2 SO CF Me HFH CN 0 2 3 2 2 3 SO CF Me HHH OMe 0 SO CF Me HFH CN 1 2 3 2 3 SO CF Me HHH OMe 1 SO CF Me HFH CN 2 2 3 2 3 SO CF Me HHH OMe 2 SO CF Me HClH CN 0 2 3 2 3 SO CF Me HHH OCF 0 SO CF Me HClH CN 1 2 3 3 2 3 SO CF Me HHH OCF 1 SO CF Me HClH CN 2 2 3 3 2 3 SO CF Me HHH OCF 2 SO CF Me HBrH CN 0 2 3 3 2 3 SO CF Me HHH NO 0 SO CF Me HBrH CN 1 2 3 2 2 3 SO CF Me HHH NO 1 SO CF Me HBrH CN 2 2 3 2 2 3 SO CF Me HHH NO 2 SO CF Me HIH CN 0 2 3 2 2 3 SO CF Me HHH CN 0 SO CF Me HIH CN 1 2 3 2 3 SO CF Me HHH CN 1 SO CF Me HIH CN 2 2 3 2 3 SO CF Me HHH CN 2 SO CF Me HCF HF 0 2 3 2 3 3 SO CF Me HFH F 0 SO CF Me HCF HF 1 2 3 2 3 3 SO CF Me HFH F 1 SO CF Me HCF HF 2 2 3 2 3 3 SO CF Me HFH F 2 SO CF Me HCF HCl 0 2 3 2 3 3 SO CF Me HClH Cl 0 SO CF Me HCF HCl 1 2 3 2 3 3 SO CF Me HClH Cl 1 SO CF Me HCF HCl 2 2 3 2 3 3 SO CF Me HClH Cl 2 SO CF Me HCF HBr 0 2 3 2 3 3 SO CF Me HBrH Br 0 SO CF Me HCF HBr 1 2 3 2 3 3 SO CF Me HBrH Br 1 SO CF Me HCF HBr 2 2 3 2 3 3 SO CF Me HBrH Br 2 SO CF Me HCF HI 0 2 3 2 3 3 SO CF Me HIH I 0 SO CF Me HCF HI 1 2 3 2 3 3 SO CF Me HIH I 1 SO CF Me HCF HI 2 2 3 2 3 3 SO CF Me HIH I 2 SO CF Me HCF HCN 0 2 3 2 3 3 SO CF Me HFH Cl 0 SO CF Me HCF HCN 1 2 3 2 3 3 SO CF Me HFH Cl 1 SO CF Me HCF HCN 2 2 3 2 3 3 SO CF Me HFH Cl 2 SO CF Me HFF H 0 2 3 2 3 SO CF Me HFH Br 0 SO CF Me HFF H 1 2 3 2 3 SO CF Me HFH Br 1 SO CF Me HFF H 2 2 3 2 3 SO CF Me HFH Br 2 SO CF Me HCl Cl H 0 2 3 2 3 SO CF Me HFH I 0 SO CF Me HCl Cl H 1 2 3 2 3 SO CF Me HFH I 1 SO CF Me HCl Cl H 2 2 3 2 3 SO CF Me HFH I 2 SO CF Me HBr Br H 0 2 3 2 3 SO CF Me HClH F 0 SO CF Me HBr Br H 1 2 3 2 3 SO CF Me HClH F 1 SO CF Me HBr Br H 2 2 3 2 3 SO CF Me HClH F 2 SO CF Me HII H 0 2 3 2 3 SO CF Me HClH Br 0 SO CF Me HII H 1 2 3 2 3 SO CF Me HClH Br 1 SO CF Me HII H 2 2 3 2 3 SO CF Me HClH Br 2 SO CF Me HF Cl H 0 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Me HF Cl H 1 SO CF Et HHH H 0 2 3 2 3 SO CF Me HF Cl H 2 SO CF Et HHH H 1 2 3 2 3 SO CF Me HF Br H 0 SO CF Et HHH H 2 2 3 2 3 SO CF Me HF Br H 1 SO CF Et FHH H 0 2 3 2 3 SO CF Me HF Br H 2 SO CF Et FHH H 1 2 3 2 3 SO CF Me HFI H 0 SO CF Et FHH H 2 2 3 2 3 SO CF Me HFI H 1 SO CF Et Cl H H H 0 2 3 2 3 SO CF Me HFI H 2 SO CF Et Cl H H H 1 2 3 2 3 SO CF Me HClF H 0 SO CF Et Cl H H H 2 2 3 2 3 SO CF Me HClF H 1 SO CF Et Br H H H 0 2 3 2 3 SO CF Me HClF H 2 SO CF Et Br H H H 1 2 3 2 3 SO CF Me HCl Br H 0 SO CF Et Br H H H 2 2 3 2 3 SO CF Me HCl Br H 1 SO CF Et IHH H 0 2 3 2 3 SO CF Me HCl Br H 2 SO CF Et IHH H 1 2 3 2 3 SO CF Me HClI H 0 SO CF Et IHH H 2 2 3 2 3 SO CF Me HClI H 1 SO CF Et Me H H H 0 2 3 2 3 SO CF Me HClI H 2 SO CF Et Me H H H 1 2 3 2 3 SO CF Me HBrF H 0 SO CF Et Me H H H 2 2 3 2 3 SO CF Me HBrF H 1 SO CF Et CF HH H 0 2 3 2 3 3 SO CF Me HBrF H 2 SO CF Et CF HH H 1 2 3 2 3 3 SO CF Me HBr Cl H 0 SO CF Et CF HH H 2 2 3 2 3 3 SO CF Me HBr Cl H 1 SO CF Et HFH H 0 2 3 2 3 SO CF Me HBr Cl H 2 SO CF Et HFH H 1 2 3 2 3 SO CF Me HBrI H 0 SO CF Et HFH H 2 2 3 2 3 SO CF Me HBrI H 1 SO CF Et HClH H 0 2 3 2 3 SO CF Me HBrI H 2 SO CF Et HClH H 1 2 3 2 3 SO CF Me HIF H 0 SO CF Et HClH H 2 2 3 2 3 SO CF Me HIF H 1 SO CF Et HBrH H 0 2 3 2 3 SO CF Me HIF H 2 SO CF Et HBrH H 1 2 3 2 3 SO CF Me HI Cl H 0 SO CF Et HBrH H 2 2 3 2 3 SO CF Me HI Cl H 1 SO CF Et HIH H 0 2 3 2 3 SO CF Me HI Cl H 2 SO CF Et HIH H 1 2 3 2 3 SO CF Me HI Br H 0 SO CF Et HIH H 2 2 3 2 3 SO CF Me HI Br H 1 SO CF Et HMeH H 0 2 3 2 3 SO CF Me HI Br H 2 SO CF Et HMeH H 1 2 3 2 3 SO CF Me HF CN H 0 SO CF Et HMeH H 2 2 3 2 3 SO CF Me HF CN H 1 SO CF Et HCF HH 0 2 3 2 3 3 SO CF Me HF CN H 2 SO CF Et HCF HH 1 2 3 2 3 3 SO CF Me HCl CN H 0 SO CF Et HCF HH 2 2 3 2 3 3 SO CF Me HCl CN H 1 SO CF Et HCF CF HH 0 2 3 2 3 2 3 SO CF Me HCl CN H 2 SO CF Et HCF CF HH 1 2 3 2 3 2 3 SO CF Me HBr CN H 0 SO CF Et HCF CF HH 2 2 3 2 3 2 3 SO CF Me HBr CN H 1 SO CF Et H CF(CF ) HH 0 2 3 2 3 3 2 SO CF Me HBr CN H 2 SO CF Et H CF(CF ) HH 1 2 3 2 3 3 2 SO CF Me HI CN H 0 SO CF Et H CF(CF ) HH 2 2 3 2 3 3 2 SO CF Me HI CN H 1 SO CF Et HSMe H H 0 2 3 2 3 SO CF Me HI CN H 2 SO CF Et HSMe H H 1 2 3 2 3 SO CF Me HCF FH 0 SO CF Et HSMe H H 2 2 3 3 2 3 SO CF Me HCF FH 1 SO CF Et HSOMeH H 0 2 3 3 2 3 SO CF Me HCF FH 2 SO CF Et HSOMeH H 1 2 3 3 2 3 SO CF Me HCF Cl H 0 SO CF Et HSOMeH H 2 2 3 3 2 3 SO CF Me HCF Cl H 1 SO CF Et HSO Me H H 0 2 3 3 2 3 2 SO CF Me HCF Cl H 2 SO CF Et HSO Me H H 1 2 3 3 2 3 2 SO CF Me HCF Br H 0 SO CF Et HSO Me H H 2 2 3 3 2 3 2 SO CF Me HCF Br H 1 SO CF Et HOMe H H 0 2 3 3 2 3 SO CF Me HCF Br H 2 SO CF Et HOMe H H 1 2 3 3 2 3 SO CF Me HCF IH 0 SO CF Et HOMe H H 2 2 3 3 2 3 SO CF Me HCF IH 1 SO CF Et HOCF HH 0 2 3 3 2 3 3 SO CF Me HCF IH 2 SO CF Et HOCF HH 1 2 3 3 2 3 3 SO CF Me HCF CN H 0 SO CF Et HOCF HH 2 2 3 3 2 3 3 SO CF Me HCF CN H 1 SO CF Et HNO HH 0 2 3 3 2 3 2 SO CF Me HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Et HNO HH 1 SO CF Et HHH I 2 2 3 2 2 3 SO CF Et HNO HH 2 SO CF Et HHH Me 0 2 3 2 2 3 SO CF Et HCNH H 0 SO CF Et HHH Me 1 2 3 2 3 SO CF Et HCNH H 1 SO CF Et HHH Me 2 2 3 2 3 SO CF Et HCNH H 2 SO CF Et HHH CF 0 2 3 2 3 3 SO CF Et HHF H 0 SO CF Et HHH CF 1 2 3 2 3 3 SO CF Et HHF H 1 SO CF Et HHH CF 2 2 3 2 3 3 SO CF Et HHF H 2 SO CF Et HHH CF CF 0 2 3 2 3 2 3 SO CF Et HH Cl H 0 SO CF Et HHH CF CF 1 2 3 2 3 2 3 SO CF Et HH Cl H 1 SO CF Et HHH CF CF 2 2 3 2 3 2 3 SO CF Et HH Cl H 2 SO CF Et HHH CF(CF ) 0 2 3 2 3 3 2 SO CF Et HH Br H 0 SO CF Et HHH CF(CF ) 1 2 3 2 3 3 2 SO CF Et HH Br H 1 SO CF Et HHH CF(CF ) 2 2 3 2 3 3 2 SO CF Et HH Br H 2 SO CF Et HHH SMe 0 2 3 2 3 SO CF Et HHI H 0 SO CF Et HHH SMe 1 2 3 2 3 SO CF Et HHI H 1 SO CF Et HHH SMe 2 2 3 2 3 SO CF Et HHI H 2 SO CF Et H H H SOMe 0 2 3 2 3 SO CF Et HH Me H 0 SO CF Et H H H SOMe 1 2 3 2 3 SO CF Et HH Me H 1 SO CF Et H H H SOMe 2 2 3 2 3 SO CF Et HH Me H 2 SO CF Et HHH SO Me 0 2 3 2 3 2 SO CF Et HH CF H 0 SO CF Et HHH SO Me 1 2 3 3 2 3 2 SO CF Et HH CF H 1 SO CF Et HHH SO Me 2 2 3 3 2 3 2 SO CF Et HH CF H 2 SO CF Et HHH OMe 0 2 3 3 2 3 SO CF Et HH CF CF H 0 SO CF Et HHH OMe 1 2 3 2 3 2 3 SO CF Et HH CF CF H 1 SO CF Et HHH OMe 2 2 3 2 3 2 3 SO CF Et HH CF CF H 2 SO CF Et HHH OCF 0 2 3 2 3 2 3 3 SO CF Et H H CF(CF ) H 0 SO CF Et HHH OCF 1 2 3 3 2 2 3 3 SO CF Et H H CF(CF ) H 1 SO CF Et HHH OCF 2 2 3 3 2 2 3 3 SO CF Et H H CF(CF ) H 2 SO CF Et HHH NO 0 2 3 3 2 2 3 2 SO CF Et HH SMe H 0 SO CF Et HHH NO 1 2 3 2 3 2 SO CF Et HH SMe H 1 SO CF Et HHH NO 2 2 3 2 3 2 SO CF Et HH SMe H 2 SO CF Et HHH CN 0 2 3 2 3 SO CF Et H H SOMe H 0 SO CF Et HHH CN 1 2 3 2 3 SO CF Et H H SOMe H 1 SO CF Et HHH CN 2 2 3 2 3 SO CF Et H H SOMe H 2 SO CF Et HFH F 0 2 3 2 3 SO CF Et HH SO Me H 0 SO CF Et HFH F 1 2 3 2 2 3 SO CF Et HH SO Me H 1 SO CF Et HFH F 2 2 3 2 2 3 SO CF Et HH SO Me H 2 SO CF Et HClH Cl 0 2 3 2 2 3 SO CF Et HH OMe H 0 SO CF Et HClH Cl 1 2 3 2 3 SO CF Et HH OMe H 1 SO CF Et HClH Cl 2 2 3 2 3 SO CF Et HH OMe H 2 SO CF Et HBrH Br 0 2 3 2 3 SO CF Et H H OCF H 0 SO CF Et HBrH Br 1 2 3 3 2 3 SO CF Et H H OCF H 1 SO CF Et HBrH Br 2 2 3 3 2 3 SO CF Et H H OCF H 2 SO CF Et HIH I 0 2 3 3 2 3 SO CF Et HH NO H 0 SO CF Et HIH I 1 2 3 2 2 3 SO CF Et HH NO H 1 SO CF Et HIH I 2 2 3 2 2 3 SO CF Et HH NO H 2 SO CF Et HFH Cl 0 2 3 2 2 3 SO CF Et HH CN H 0 SO CF Et HFH Cl 1 2 3 2 3 SO CF Et HH CN H 1 SO CF Et HFH Cl 2 2 3 2 3 SO CF Et HH CN H 2 SO CF Et HFH Br 0 2 3 2 3 SO CF Et HHH F 0 SO CF Et HFH Br 1 2 3 2 3 SO CF Et HHH F 1 SO CF Et HFH Br 2 2 3 2 3 SO CF Et HHH F 2 SO CF Et HFH I 0 2 3 2 3 SO CF Et HHH Cl 0 SO CF Et HFH I 1 2 3 2 3 SO CF Et HHH Cl 1 SO CF Et HFH I 2 2 3 2 3 SO CF Et HHH Cl 2 SO CF Et HClH F 0 2 3 2 3 SO CF Et HHH Br 0 SO CF Et HClH F 1 2 3 2 3 SO CF Et HHH Br 1 SO CF Et HClH F 2 2 3 2 3 SO CF Et HHH Br 2 SO CF Et HClH Br 0 2 3 2 3 SO CF Et HHH I 0 SO CF Et HClH Br 1 2 3 2 3 SO CF Et HHH I 1 SO CF Et HClH Br 2 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Et HClH I 0 SO CF Et HF Cl H 1 2 3 2 3 SO CF Et HClH I 1 SO CF Et HF Cl H 2 2 3 2 3 SO CF Et HClH I 2 SO CF Et HF Br H 0 2 3 2 3 SO CF Et HBrH F 0 SO CF Et HF Br H 1 2 3 2 3 SO CF Et HBrH F 1 SO CF Et HF Br H 2 2 3 2 3 SO CF Et HBrH F 2 SO CF Et HFI H 0 2 3 2 3 SO CF Et HBrH Cl 0 SO CF Et HFI H 1 2 3 2 3 SO CF Et HBrH Cl 1 SO CF Et HFI H 2 2 3 2 3 SO CF Et HBrH Cl 2 SO CF Et HClF H 0 2 3 2 3 SO CF Et HBrH I 0 SO CF Et HClF H 1 2 3 2 3 SO CF Et HBrH I 1 SO CF Et HClF H 2 2 3 2 3 SO CF Et HBrH I 2 SO CF Et HCl Br H 0 2 3 2 3 SO CF Et HIH F 0 SO CF Et HCl Br H 1 2 3 2 3 SO CF Et HIH F 1 SO CF Et HCl Br H 2 2 3 2 3 SO CF Et HIH F 2 SO CF Et HClI H 0 2 3 2 3 SO CF Et HIH Cl 0 SO CF Et HClI H 1 2 3 2 3 SO CF Et HIH Cl 1 SO CF Et HClI H 2 2 3 2 3 SO CF Et HIH Cl 2 SO CF Et HBrF H 0 2 3 2 3 SO CF Et HIH Br 0 SO CF Et HBrF H 1 2 3 2 3 SO CF Et HIH Br 1 SO CF Et HBrF H 2 2 3 2 3 SO CF Et HIH Br 2 SO CF Et HBr Cl H 0 2 3 2 3 SO CF Et HFH CN 0 SO CF Et HBr Cl H 1 2 3 2 3 SO CF Et HFH CN 1 SO CF Et HBr Cl H 2 2 3 2 3 SO CF Et HFH CN 2 SO CF Et HBrI H 0 2 3 2 3 SO CF Et HClH CN 0 SO CF Et HBrI H 1 2 3 2 3 SO CF Et HClH CN 1 SO CF Et HBrI H 2 2 3 2 3 SO CF Et HClH CN 2 SO CF Et HIF H 0 2 3 2 3 SO CF Et HBrH CN 0 SO CF Et HIF H 1 2 3 2 3 SO CF Et HBrH CN 1 SO CF Et HIF H 2 2 3 2 3 SO CF Et HBrH CN 2 SO CF Et HI Cl H 0 2 3 2 3 SO CF Et HIH CN 0 SO CF Et HI Cl H 1 2 3 2 3 SO CF Et HIH CN 1 SO CF Et HI Cl H 2 2 3 2 3 SO CF Et HIH CN 2 SO CF Et HI Br H 0 2 3 2 3 SO CF Et HCF HF 0 SO CF Et HI Br H 1 2 3 3 2 3 SO CF Et HCF HF 1 SO CF Et HI Br H 2 2 3 3 2 3 SO CF Et HCF HF 2 SO CF Et HF CN H 0 2 3 3 2 3 SO CF Et HCF HCl 0 SO CF Et HF CN H 1 2 3 3 2 3 SO CF Et HCF HCl 1 SO CF Et HF CN H 2 2 3 3 2 3 SO CF Et HCF HCl 2 SO CF Et HCl CN H 0 2 3 3 2 3 SO CF Et HCF HBr 0 SO CF Et HCl CN H 1 2 3 3 2 3 SO CF Et HCF HBr 1 SO CF Et HCl CN H 2 2 3 3 2 3 SO CF Et HCF HBr 2 SO CF Et HBr CN H 0 2 3 3 2 3 SO CF Et HCF HI 0 SO CF Et HBr CN H 1 2 3 3 2 3 SO CF Et HCF HI 1 SO CF Et HBr CN H 2 2 3 3 2 3 SO CF Et HCF HI 2 SO CF Et HI CN H 0 2 3 3 2 3 SO CF Et HCF HCN 0 SO CF Et HI CN H 1 2 3 3 2 3 SO CF Et HCF HCN 1 SO CF Et HI CN H 2 2 3 3 2 3 SO CF Et HCF HCN 2 SO CF Et HCF FH 0 2 3 3 2 3 3 SO CF Et HFF H 0 SO CF Et HCF FH 1 2 3 2 3 3 SO CF Et HFF H 1 SO CF Et HCF FH 2 2 3 2 3 3 SO CF Et HFF H 2 SO CF Et HCF Cl H 0 2 3 2 3 3 SO CF Et HCl Cl H 0 SO CF Et HCF Cl H 1 2 3 2 3 3 SO CF Et HCl Cl H 1 SO CF Et HCF Cl H 2 2 3 2 3 3 SO CF Et HCl Cl H 2 SO CF Et HCF Br H 0 2 3 2 3 3 SO CF Et HBr Br H 0 SO CF Et HCF Br H 1 2 3 2 3 3 SO CF Et HBr Br H 1 SO CF Et HCF Br H 2 2 3 2 3 3 SO CF Et HBr Br H 2 SO CF Et HCF IH 0 2 3 2 3 3 SO CF Et HII H 0 SO CF Et HCF IH 1 2 3 2 3 3 SO CF Et HII H 1 SO CF Et HCF IH 2 2 3 2 3 3 SO CF Et HII H 2 SO CF Et HCF CN H 0 2 3 2 3 3 SO CF Et HF Cl H 0 SO CF Et HCF CN H 1 2 3 2 3 3 SO CF Et HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Pr HHH H 0 SO CF Pr HNO HH 1 2 3 2 3 2 SO CF HHH H 1 SO CF HNO HH 2 Pr Pr 2 3 2 3 2 SO CF Pr HHH H 2 SO CF Pr HCNH H 0 2 3 2 3 SO CF FHH H 0 SO CF HCNH H 1 Pr Pr 2 3 2 3 SO CF Pr FHH H 1 SO CF Pr HCNH H 2 2 3 2 3 SO CF Pr FHH H 2 SO CF Pr HHF H 0 2 3 2 3 SO CF Pr Cl H H H 0 SO CF Pr HHF H 1 2 3 2 3 SO CF Pr Cl H H H 1 SO CF Pr HHF H 2 2 3 2 3 SO CF Cl H H H 2 SO CF HH Cl H 0 Pr Pr 2 3 2 3 SO CF Pr Br H H H 0 SO CF Pr HH Cl H 1 2 3 2 3 SO CF Br H H H 1 SO CF HH Cl H 2 Pr Pr 2 3 2 3 SO CF Pr Br H H H 2 SO CF Pr HH Br H 0 2 3 2 3 SO CF IHH H 0 SO CF HH Br H 1 Pr Pr 2 3 2 3 SO CF Pr IHH H 1 SO CF Pr HH Br H 2 2 3 2 3 SO CF IHH H 2 SO CF HHI H 0 Pr Pr 2 3 2 3 SO CF Pr Me H H H 0 SO CF Pr HHI H 1 2 3 2 3 SO CF Pr Me H H H 1 SO CF Pr HHI H 2 2 3 2 3 SO CF Me H H H 2 SO CF HH Me H 0 Pr Pr 2 3 2 3 SO CF Pr CF HH H 0 SO CF Pr HH Me H 1 2 3 3 2 3 SO CF CF HH H 1 SO CF HH Me H 2 Pr Pr 2 3 3 2 3 SO CF Pr CF HH H 2 SO CF Pr HH CF H 0 2 3 3 2 3 3 SO CF HFH H 0 SO CF HH CF H 1 Pr Pr 2 3 2 3 3 SO CF Pr HFH H 1 SO CF Pr HH CF H 2 2 3 2 3 3 SO CF Pr HFH H 2 SO CF Pr HH CF CF H 0 2 3 2 3 2 3 SO CF Pr HClH H 0 SO CF Pr HH CF CF H 1 2 3 2 3 2 3 SO CF Pr HClH H 1 SO CF Pr HH CF CF H 2 2 3 2 3 2 3 SO CF HClH H 2 SO CF HH CF(CF ) H 0 Pr Pr 2 3 2 3 3 2 SO CF Pr HBrH H 0 SO CF Pr HH CF(CF ) H 1 2 3 2 3 3 2 SO CF HBrH H 1 SO CF HH CF(CF ) H 2 Pr Pr 2 3 2 3 3 2 SO CF Pr HBrH H 2 SO CF Pr HH SMe H 0 2 3 2 3 SO CF HIH H 0 SO CF HH SMe H 1 Pr Pr 2 3 2 3 SO CF Pr HIH H 1 SO CF Pr HH SMe H 2 2 3 2 3 SO CF Pr HIH H 2 SO CF Pr HH SOMe H 0 2 3 2 3 SO CF Pr HMeH H 0 SO CF Pr HH SOMe H 1 2 3 2 3 SO CF Pr HMeH H 1 SO CF Pr HH SOMe H 2 2 3 2 3 SO CF HMeH H 2 SO CF HH SO Me H 0 Pr Pr 2 3 2 3 2 SO CF Pr HCF HH 0 SO CF Pr HH SO Me H 1 2 3 3 2 3 2 SO CF HCF HH 1 SO CF HH SO Me H 2 Pr Pr 2 3 3 2 3 2 SO CF Pr HCF HH 2 SO CF Pr HH OMe H 0 2 3 3 2 3 SO CF HCF CF HH 0 SO CF HH OMe H 1 Pr Pr 2 3 2 3 2 3 SO CF Pr HCF CF HH 1 SO CF Pr HH OMe H 2 2 3 2 3 2 3 SO CF HCF CF HH 2 SO CF HH OCF H 0 Pr Pr 2 3 2 3 2 3 3 SO CF Pr H CF(CF ) HH 0 SO CF Pr HH OCF H 1 2 3 3 2 2 3 3 SO CF Pr H CF(CF ) HH 1 SO CF Pr HH OCF H 2 2 3 3 2 2 3 3 SO CF H CF(CF ) HH 2 SO CF HH NO H 0 Pr Pr 2 3 3 2 2 3 2 SO CF Pr H SMe H H 0 SO CF Pr HH NO H 1 2 3 2 3 2 SO CF H SMe H H 1 SO CF HH NO H 2 Pr Pr 2 3 2 3 2 SO CF Pr H SMe H H 2 SO CF Pr HH CN H 0 2 3 2 3 SO CF HSOMeH H 0 SO CF HH CN H 1 Pr Pr 2 3 2 3 SO CF Pr HSOMeH H 1 SO CF Pr HH CN H 2 2 3 2 3 SO CF Pr HSOMeH H 2 SO CF Pr HHH F 0 2 3 2 3 SO CF Pr HSO Me H H 0 SO CF Pr HHH F 1 2 3 2 2 3 SO CF Pr HSO Me H H 1 SO CF Pr HHH F 2 2 3 2 2 3 SO CF HSO Me H H 2 SO CF HHH Cl 0 Pr Pr 2 3 2 2 3 SO CF Pr H OMe H H 0 SO CF Pr HHH Cl 1 2 3 2 3 SO CF H OMe H H 1 SO CF HHH Cl 2 Pr Pr 2 3 2 3 SO CF Pr H OMe H H 2 SO CF Pr HHH Br 0 2 3 2 3 SO CF HOCF HH 0 SO CF HHH Br 1 Pr Pr 2 3 3 2 3 SO CF Pr HOCF HH 1 SO CF Pr HHH Br 2 2 3 3 2 3 SO CF HOCF HH 2 SO CF HHH I 0 Pr Pr 2 3 3 2 3 SO CF Pr HNO HH 0 SO CF Pr HHH I 1 2 3 2 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Pr HHH I 2 SO CF Pr HClH I 0 2 3 2 3 SO CF HHH Me 0 SO CF HClH I 1 Pr Pr 2 3 2 3 SO CF Pr HHH Me 1 SO CF Pr HClH I 2 2 3 2 3 SO CF HHH Me 2 SO CF HBrH F 0 Pr Pr 2 3 2 3 SO CF Pr HHH CF 0 SO CF Pr HBrH F 1 2 3 3 2 3 SO CF Pr HHH CF 1 SO CF Pr HBrH F 2 2 3 3 2 3 SO CF Pr HHH CF 2 SO CF Pr HBrH Cl 0 2 3 3 2 3 SO CF Pr HHH CF CF 0 SO CF Pr HBrH Cl 1 2 3 2 3 2 3 SO CF HHH CF CF 1 SO CF HBrH Cl 2 Pr Pr 2 3 2 3 2 3 SO CF Pr HHH CF CF 2 SO CF Pr HBrH I 0 2 3 2 3 2 3 SO CF H H H CF(CF ) 0 SO CF HBrH I 1 Pr Pr 2 3 3 2 2 3 SO CF Pr H H H CF(CF ) 1 SO CF Pr HBrH I 2 2 3 3 2 2 3 SO CF H H H CF(CF ) 2 SO CF HIH F 0 Pr Pr 2 3 3 2 2 3 SO CF Pr HHH SMe 0 SO CF Pr HIH F 1 2 3 2 3 SO CF HHH SMe 1 SO CF HIH F 2 Pr Pr 2 3 2 3 SO CF Pr HHH SMe 2 SO CF Pr HIH Cl 0 2 3 2 3 SO CF Pr HHH SOMe 0 SO CF Pr HIH Cl 1 2 3 2 3 SO CF HHH SOMe 1 SO CF HIH Cl 2 Pr Pr 2 3 2 3 SO CF Pr HHH SOMe 2 SO CF Pr HIH Br 0 2 3 2 3 SO CF HHH SO Me 0 SO CF HIH Br 1 Pr Pr 2 3 2 2 3 SO CF Pr HHH SO Me 1 SO CF Pr HIH Br 2 2 3 2 2 3 SO CF HHH SO Me 2 SO CF HFH CN 0 Pr Pr 2 3 2 2 3 SO CF Pr HHH OMe 0 SO CF Pr HFH CN 1 2 3 2 3 SO CF Pr HHH OMe 1 SO CF Pr HFH CN 2 2 3 2 3 SO CF Pr HHH OMe 2 SO CF Pr HClH CN 0 2 3 2 3 SO CF Pr HHH OCF 0 SO CF Pr HClH CN 1 2 3 3 2 3 SO CF HHH OCF 1 SO CF HClH CN 2 Pr Pr 2 3 3 2 3 SO CF Pr HHH OCF 2 SO CF Pr HBrH CN 0 2 3 3 2 3 SO CF HHH NO 0 SO CF HBrH CN 1 Pr Pr 2 3 2 2 3 SO CF Pr HHH NO 1 SO CF Pr HBrH CN 2 2 3 2 2 3 SO CF HHH NO 2 SO CF HIH CN 0 Pr Pr 2 3 2 2 3 SO CF Pr HHH CN 0 SO CF Pr HIH CN 1 2 3 2 3 SO CF Pr HHH CN 1 SO CF Pr HIH CN 2 2 3 2 3 SO CF Pr HHH CN 2 SO CF Pr HCF HF 0 2 3 2 3 3 SO CF Pr HFH F 0 SO CF Pr HCF HF 1 2 3 2 3 3 SO CF HFH F 1 SO CF HCF HF 2 Pr Pr 2 3 2 3 3 SO CF Pr HFH F 2 SO CF Pr HCF HCl 0 2 3 2 3 3 SO CF HClH Cl 0 SO CF HCF HCl 1 Pr Pr 2 3 2 3 3 SO CF Pr HClH Cl 1 SO CF Pr HCF HCl 2 2 3 2 3 3 SO CF HClH Cl 2 SO CF HCF HBr 0 Pr Pr 2 3 2 3 3 SO CF Pr HBrH Br 0 SO CF Pr HCF HBr 1 2 3 2 3 3 SO CF HBrH Br 1 SO CF HCF HBr 2 Pr Pr 2 3 2 3 3 SO CF Pr HBrH Br 2 SO CF Pr HCF HI 0 2 3 2 3 3 SO CF Pr HIH I 0 SO CF Pr HCF HI 1 2 3 2 3 3 SO CF HIH I 1 SO CF HCF HI 2 Pr Pr 2 3 2 3 3 SO CF Pr HIH I 2 SO CF Pr HCF HCN 0 2 3 2 3 3 SO CF HFH Cl 0 SO CF HCF HCN 1 Pr Pr 2 3 2 3 3 SO CF Pr HFH Cl 1 SO CF Pr HCF HCN 2 2 3 2 3 3 SO CF HFH Cl 2 SO CF HFF H 0 Pr Pr 2 3 2 3 SO CF Pr HFH Br 0 SO CF Pr HFF H 1 2 3 2 3 SO CF Pr HFH Br 1 SO CF Pr HFF H 2 2 3 2 3 SO CF Pr HFH Br 2 SO CF Pr HCl Cl H 0 2 3 2 3 SO CF Pr HFH I 0 SO CF Pr HCl Cl H 1 2 3 2 3 SO CF HFH I 1 SO CF HCl Cl H 2 Pr Pr 2 3 2 3 SO CF Pr HFH I 2 SO CF Pr HBr Br H 0 2 3 2 3 SO CF HClH F 0 SO CF HBr Br H 1 Pr Pr 2 3 2 3 SO CF Pr HClH F 1 SO CF Pr HBr Br H 2 2 3 2 3 SO CF HClH F 2 SO CF HII H 0 Pr Pr 2 3 2 3 SO CF Pr HClH Br 0 SO CF Pr HII H 1 2 3 2 3 SO CF HClH Br 1 SO CF HII H 2 Pr Pr 2 3 2 3 SO CF Pr HClH Br 2 SO CF Pr HF Cl H 0 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Pr HF Cl H 1 SO CF Pr HHH H 0 2 3 2 3 SO CF HF Cl H 2 SO CF HHH H 1 Pr Pr 2 3 2 3 SO CF Pr HF Br H 0 SO CF Pr HHH H 2 2 3 2 3 SO CF HF Br H 1 SO CF FHH H 0 Pr Pr 2 3 2 3 SO CF Pr HF Br H 2 SO CF Pr FHH H 1 2 3 2 3 SO CF HFI H 0 SO CF FHH H 2 Pr Pr 2 3 2 3 SO CF Pr HFI H 1 SO CF Pr Cl H H H 0 2 3 2 3 SO CF Pr HFI H 2 SO CF Pr Cl H H H 1 2 3 2 3 SO CF Pr HClF H 0 SO CF Pr Cl H H H 2 2 3 2 3 SO CF Pr HClF H 1 SO CF Pr Br H H H 0 2 3 2 3 SO CF HClF H 2 SO CF Br H H H 1 Pr Pr 2 3 2 3 SO CF Pr HCl Br H 0 SO CF Pr Br H H H 2 2 3 2 3 SO CF HCl Br H 1 SO CF IHH H 0 Pr Pr 2 3 2 3 SO CF Pr HCl Br H 2 SO CF Pr IHH H 1 2 3 2 3 SO CF HClI H 0 SO CF IHH H 2 Pr Pr 2 3 2 3 SO CF Pr HClI H 1 SO CF Pr Me H H H 0 2 3 2 3 SO CF Pr HClI H 2 SO CF Pr Me H H H 1 2 3 2 3 SO CF Pr HBrF H 0 SO CF Pr Me H H H 2 2 3 2 3 SO CF Pr HBrF H 1 SO CF Pr CF HH H 0 2 3 2 3 3 SO CF HBrF H 2 SO CF CF HH H 1 Pr Pr 2 3 2 3 3 SO CF Pr HBr Cl H 0 SO CF Pr CF HH H 2 2 3 2 3 3 SO CF HBr Cl H 1 SO CF HFH H 0 Pr Pr 2 3 2 3 SO CF Pr HBr Cl H 2 SO CF Pr HFH H 1 2 3 2 3 SO CF HBrI H 0 SO CF HFH H 2 Pr Pr 2 3 2 3 SO CF Pr HBrI H 1 SO CF Pr HClH H 0 2 3 2 3 SO CF HBrI H 2 SO CF HClH H 1 Pr Pr 2 3 2 3 SO CF Pr HIF H 0 SO CF Pr HClH H 2 2 3 2 3 SO CF Pr HIF H 1 SO CF Pr HBrH H 0 2 3 2 3 SO CF Pr HIF H 2 SO CF Pr HBrH H 1 2 3 2 3 SO CF Pr HI Cl H 0 SO CF Pr HBrH H 2 2 3 2 3 SO CF HI Cl H 1 SO CF HIH H 0 Pr Pr 2 3 2 3 SO CF Pr HI Cl H 2 SO CF Pr HIH H 1 2 3 2 3 SO CF HI Br H 0 SO CF HIH H 2 Pr Pr 2 3 2 3 SO CF Pr HI Br H 1 SO CF Pr HMeH H 0 2 3 2 3 SO CF HI Br H 2 SO CF HMeH H 1 Pr Pr 2 3 2 3 SO CF Pr HF CN H 0 SO CF Pr HMeH H 2 2 3 2 3 SO CF Pr HF CN H 1 SO CF Pr HCF HH 0 2 3 2 3 3 SO CF Pr HF CN H 2 SO CF Pr HCF HH 1 2 3 2 3 3 SO CF Pr HCl CN H 0 SO CF Pr HCF HH 2 2 3 2 3 3 SO CF HCl CN H 1 SO CF HCF CF HH 0 Pr Pr 2 3 2 3 2 3 SO CF Pr HCl CN H 2 SO CF Pr HCF CF HH 1 2 3 2 3 2 3 SO CF HBr CN H 0 SO CF HCF CF HH 2 Pr Pr 2 3 2 3 2 3 SO CF Pr HBr CN H 1 SO CF Pr H CF(CF ) HH 0 2 3 2 3 3 2 SO CF HBr CN H 2 SO CF H CF(CF ) HH 1 Pr Pr 2 3 2 3 3 2 SO CF Pr HI CN H 0 SO CF Pr H CF(CF ) HH 2 2 3 2 3 3 2 SO CF HI CN H 1 SO CF HSMe H H 0 Pr Pr 2 3 2 3 SO CF Pr HI CN H 2 SO CF Pr HSMe H H 1 2 3 2 3 SO CF HCF FH 0 SO CF HSMe H H 2 Pr Pr 2 3 3 2 3 SO CF Pr HCF FH 1 SO CF Pr HSOMeH H 0 2 3 3 2 3 SO CF Pr HCF FH 2 SO CF Pr HSOMeH H 1 2 3 3 2 3 SO CF HCF Cl H 0 SO CF HSOMeH H 2 Pr Pr 2 3 3 2 3 SO CF Pr HCF Cl H 1 SO CF Pr HSO Me H H 0 2 3 3 2 3 2 SO CF HCF Cl H 2 SO CF HSO Me H H 1 Pr Pr 2 3 3 2 3 2 SO CF Pr HCF Br H 0 SO CF Pr HSO Me H H 2 2 3 3 2 3 2 SO CF HCF Br H 1 SO CF HOMe H H 0 Pr Pr 2 3 3 2 3 SO CF Pr HCF Br H 2 SO CF Pr HOMe H H 1 2 3 3 2 3 SO CF Pr HCF IH 0 SO CF Pr HOMe H H 2 2 3 3 2 3 SO CF Pr HCF IH 1 SO CF Pr HOCF HH 0 2 3 3 2 3 3 SO CF Pr HCF IH 2 SO CF Pr HOCF HH 1 2 3 3 2 3 3 SO CF Pr HCF CN H 0 SO CF Pr HOCF HH 2 2 3 3 2 3 3 SO CF Pr HCF CN H 1 SO CF Pr HNO HH 0 2 3 3 2 3 2 SO CF HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Pr HNO HH 1 SO CF Pr HHH I 2 2 3 2 2 3 SO CF HNO HH 2 SO CF HHH Me 0 Pr Pr 2 3 2 2 3 SO CF Pr HCNH H 0 SO CF Pr HHH Me 1 2 3 2 3 SO CF HCNH H 1 SO CF HHH Me 2 Pr Pr 2 3 2 3 SO CF Pr HCNH H 2 SO CF Pr HHH CF 0 2 3 2 3 3 SO CF Pr HHF H 0 SO CF Pr HHH CF 1 2 3 2 3 3 SO CF Pr HHF H 1 SO CF Pr HHH CF 2 2 3 2 3 3 SO CF Pr HHF H 2 SO CF Pr HHH CF CF 0 2 3 2 3 2 3 SO CF HH Cl H 0 SO CF HHH CF CF 1 Pr Pr 2 3 2 3 2 3 SO CF Pr HH Cl H 1 SO CF Pr HHH CF CF 2 2 3 2 3 2 3 SO CF HH Cl H 2 SO CF HHH CF(CF ) 0 Pr Pr 2 3 2 3 3 2 SO CF Pr HH Br H 0 SO CF Pr HHH CF(CF ) 1 2 3 2 3 3 2 SO CF HH Br H 1 SO CF HHH CF(CF ) 2 Pr Pr 2 3 2 3 3 2 SO CF Pr HH Br H 2 SO CF Pr HHH SMe 0 2 3 2 3 SO CF HHI H 0 SO CF HHH SMe 1 Pr Pr 2 3 2 3 SO CF Pr HHI H 1 SO CF Pr HHH SMe 2 2 3 2 3 SO CF Pr HHI H 2 SO CF Pr H H H SOMe 0 2 3 2 3 SO CF HH Me H 0 SO CF H H H SOMe 1 Pr Pr 2 3 2 3 SO CF Pr HH Me H 1 SO CF Pr H H H SOMe 2 2 3 2 3 SO CF HH Me H 2 SO CF HHH SO Me 0 Pr Pr 2 3 2 3 2 SO CF Pr HH CF H 0 SO CF Pr HHH SO Me 1 2 3 3 2 3 2 SO CF HH CF H 1 SO CF HHH SO Me 2 Pr Pr 2 3 3 2 3 2 SO CF Pr HH CF H 2 SO CF Pr HHH OMe 0 2 3 3 2 3 SO CF Pr HH CF CF H 0 SO CF Pr HHH OMe 1 2 3 2 3 2 3 SO CF Pr HH CF CF H 1 SO CF Pr HHH OMe 2 2 3 2 3 2 3 SO CF Pr HH CF CF H 2 SO CF Pr HHH OCF 0 2 3 2 3 2 3 3 SO CF H H CF(CF ) H 0 SO CF HHH OCF 1 Pr Pr 2 3 3 2 2 3 3 SO CF Pr H H CF(CF ) H 1 SO CF Pr HHH OCF 2 2 3 3 2 2 3 3 SO CF H H CF(CF ) H 2 SO CF HHH NO 0 Pr Pr 2 3 3 2 2 3 2 SO CF Pr HH SMe H 0 SO CF Pr HHH NO 1 2 3 2 3 2 SO CF HH SMe H 1 SO CF HHH NO 2 Pr Pr 2 3 2 3 2 SO CF Pr HH SMe H 2 SO CF Pr HHH CN 0 2 3 2 3 SO CF Pr H H SOMe H 0 SO CF Pr HHH CN 1 2 3 2 3 SO CF Pr H H SOMe H 1 SO CF Pr HHH CN 2 2 3 2 3 SO CF Pr H H SOMe H 2 SO CF Pr HFH F 0 2 3 2 3 SO CF HH SO Me H 0 SO CF HFH F 1 Pr Pr 2 3 2 2 3 SO CF Pr HH SO Me H 1 SO CF Pr HFH F 2 2 3 2 2 3 SO CF HH SO Me H 2 SO CF HClH Cl 0 Pr Pr 2 3 2 2 3 SO CF Pr HH OMe H 0 SO CF Pr HClH Cl 1 2 3 2 3 SO CF HH OMe H 1 SO CF HClH Cl 2 Pr Pr 2 3 2 3 SO CF Pr HH OMe H 2 SO CF Pr HBrH Br 0 2 3 2 3 SO CF H H OCF H 0 SO CF HBrH Br 1 Pr Pr 2 3 3 2 3 SO CF Pr H H OCF H 1 SO CF Pr HBrH Br 2 2 3 3 2 3 SO CF Pr H H OCF H 2 SO CF Pr HIH I 0 2 3 3 2 3 SO CF HH NO H 0 SO CF HIH I 1 Pr Pr 2 3 2 2 3 SO CF Pr HH NO H 1 SO CF Pr HIH I 2 2 3 2 2 3 SO CF HH NO H 2 SO CF HFH Cl 0 Pr Pr 2 3 2 2 3 SO CF Pr HH CN H 0 SO CF Pr HFH Cl 1 2 3 2 3 SO CF HH CN H 1 SO CF HFH Cl 2 Pr Pr 2 3 2 3 SO CF Pr HH CN H 2 SO CF Pr HFH Br 0 2 3 2 3 SO CF Pr HHH F 0 SO CF Pr HFH Br 1 2 3 2 3 SO CF Pr HHH F 1 SO CF Pr HFH Br 2 2 3 2 3 SO CF Pr HHH F 2 SO CF Pr HFH I 0 2 3 2 3 SO CF HHH Cl 0 SO CF HFH I 1 Pr Pr 2 3 2 3 SO CF Pr HHH Cl 1 SO CF Pr HFH I 2 2 3 2 3 SO CF HHH Cl 2 SO CF HClH F 0 Pr Pr 2 3 2 3 SO CF Pr HHH Br 0 SO CF Pr HClH F 1 2 3 2 3 SO CF HHH Br 1 SO CF HClH F 2 Pr Pr 2 3 2 3 SO CF Pr HHH Br 2 SO CF Pr HClH Br 0 2 3 2 3 SO CF HHH I 0 SO CF HClH Br 1 Pr Pr 2 3 2 3 SO CF Pr HHH I 1 SO CF Pr HClH Br 2 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF Pr HClH I 0 SO CF Pr HF Cl H 1 2 3 2 3 SO CF HClH I 1 SO CF HF Cl H 2 Pr Pr 2 3 2 3 SO CF Pr HClH I 2 SO CF Pr HF Br H 0 2 3 2 3 SO CF HBrH F 0 SO CF HF Br H 1 Pr Pr 2 3 2 3 SO CF Pr HBrH F 1 SO CF Pr HF Br H 2 2 3 2 3 SO CF HBrH F 2 SO CF HFI H 0 Pr Pr 2 3 2 3 SO CF Pr HBrH Cl 0 SO CF Pr HFI H 1 2 3 2 3 SO CF Pr HBrH Cl 1 SO CF Pr HFI H 2 2 3 2 3 SO CF Pr HBrH Cl 2 SO CF Pr HClF H 0 2 3 2 3 SO CF Pr HBrH I 0 SO CF Pr HClF H 1 2 3 2 3 SO CF HBrH I 1 SO CF HClF H 2 Pr Pr 2 3 2 3 SO CF Pr HBrH I 2 SO CF Pr HCl Br H 0 2 3 2 3 SO CF HIH F 0 SO CF HCl Br H 1 Pr Pr 2 3 2 3 SO CF Pr HIH F 1 SO CF Pr HCl Br H 2 2 3 2 3 SO CF HIH F 2 SO CF HClI H 0 Pr Pr 2 3 2 3 SO CF Pr HIH Cl 0 SO CF Pr HClI H 1 2 3 2 3 SO CF Pr HIH Cl 1 SO CF Pr HClI H 2 2 3 2 3 SO CF Pr HIH Cl 2 SO CF Pr HBrF H 0 2 3 2 3 SO CF Pr HIH Br 0 SO CF Pr HBrF H 1 2 3 2 3 SO CF HIH Br 1 SO CF HBrF H 2 Pr Pr 2 3 2 3 SO CF Pr HIH Br 2 SO CF Pr HBr Cl H 0 2 3 2 3 SO CF HFH CN 0 SO CF HBr Cl H 1 Pr Pr 2 3 2 3 SO CF Pr HFH CN 1 SO CF Pr HBr Cl H 2 2 3 2 3 SO CF HFH CN 2 SO CF HBrI H 0 Pr Pr 2 3 2 3 SO CF Pr HClH CN 0 SO CF Pr HBrI H 1 2 3 2 3 SO CF HClH CN 1 SO CF HBrI H 2 Pr Pr 2 3 2 3 SO CF Pr HClH CN 2 SO CF Pr HIF H 0 2 3 2 3 SO CF Pr HBrH CN 0 SO CF Pr HIF H 1 2 3 2 3 SO CF Pr HBrH CN 1 SO CF Pr HIF H 2 2 3 2 3 SO CF Pr HBrH CN 2 SO CF Pr HI Cl H 0 2 3 2 3 SO CF HIH CN 0 SO CF HI Cl H 1 Pr Pr 2 3 2 3 SO CF Pr HIH CN 1 SO CF Pr HI Cl H 2 2 3 2 3 SO CF HIH CN 2 SO CF HI Br H 0 Pr Pr 2 3 2 3 SO CF Pr HCF HF 0 SO CF Pr HI Br H 1 2 3 3 2 3 SO CF HCF HF 1 SO CF HI Br H 2 Pr Pr 2 3 3 2 3 SO CF Pr HCF HF 2 SO CF Pr HF CN H 0 2 3 3 2 3 SO CF Pr HCF HCl 0 SO CF Pr HF CN H 1 2 3 3 2 3 SO CF Pr HCF HCl 1 SO CF Pr HF CN H 2 2 3 3 2 3 SO CF Pr HCF HCl 2 SO CF Pr HCl CN H 0 2 3 3 2 3 SO CF HCF HBr 0 SO CF HCl CN H 1 Pr Pr 2 3 3 2 3 SO CF Pr HCF HBr 1 SO CF Pr HCl CN H 2 2 3 3 2 3 SO CF HCF HBr 2 SO CF HBr CN H 0 Pr Pr 2 3 3 2 3 SO CF Pr HCF HI 0 SO CF Pr HBr CN H 1 2 3 3 2 3 SO CF HCF HI 1 SO CF HBr CN H 2 Pr Pr 2 3 3 2 3 SO CF Pr HCF HI 2 SO CF Pr HI CN H 0 2 3 3 2 3 SO CF HCF HCN 0 SO CF HI CN H 1 Pr Pr 2 3 3 2 3 SO CF Pr HCF HCN 1 SO CF Pr HI CN H 2 2 3 3 2 3 SO CF HCF HCN 2 SO CF HCF FH 0 Pr Pr 2 3 3 2 3 3 SO CF Pr HFF H 0 SO CF Pr HCF FH 1 2 3 2 3 3 SO CF Pr HFF H 1 SO CF Pr HCF FH 2 2 3 2 3 3 SO CF HFF H 2 SO CF HCF Cl H 0 Pr Pr 2 3 2 3 3 SO CF Pr HCl Cl H 0 SO CF Pr HCF Cl H 1 2 3 2 3 3 SO CF HCl Cl H 1 SO CF HCF Cl H 2 Pr Pr 2 3 2 3 3 SO CF Pr HCl Cl H 2 SO CF Pr HCF Br H 0 2 3 2 3 3 SO CF HBr Br H 0 SO CF HCF Br H 1 Pr Pr 2 3 2 3 3 SO CF Pr HBr Br H 1 SO CF Pr HCF Br H 2 2 3 2 3 3 SO CF Pr HBr Br H 2 SO CF Pr HCF IH 0 2 3 2 3 3 SO CF Pr HII H 0 SO CF Pr HCF IH 1 2 3 2 3 3 SO CF Pr HII H 1 SO CF Pr HCF IH 2 2 3 2 3 3 SO CF Pr HII H 2 SO CF Pr HCF CN H 0 2 3 2 3 3 SO CF Pr HF Cl H 0 SO CF Pr HCF CN H 1 2 3 2 3 3 SO CF HCF CN H 2 2 3 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF CH CF HHH H 0 SO CF CH CF HNO HH 1 2 3 2 3 2 3 2 3 2 SO CF CH CF HHH H 1 SO CF CH CF HNO HH 2 2 3 2 3 2 3 2 3 2 SO CF CH CF HHH H 2 SO CF CH CF HCNH H 0 2 3 2 3 2 3 2 3 SO CF CH CF FHH H 0 SO CF CH CF HCNH H 1 2 3 2 3 2 3 2 3 SO CF CH CF FHH H 1 SO CF CH CF HCNH H 2 2 3 2 3 2 3 2 3 SO CF CH CF FHH H 2 SO CF CH CF HHF H 0 2 3 2 3 2 3 2 3 SO CF CH CF Cl H H H 0 SO CF CH CF HHF H 1 2 3 2 3 2 3 2 3 SO CF CH CF Cl H H H 1 SO CF CH CF HHF H 2 2 3 2 3 2 3 2 3 SO CF CH CF Cl H H H 2 SO CF CH CF HH Cl H 0 2 3 2 3 2 3 2 3 SO CF CH CF Br H H H 0 SO CF CH CF HH Cl H 1 2 3 2 3 2 3 2 3 SO CF CH CF Br H H H 1 SO CF CH CF HH Cl H 2 2 3 2 3 2 3 2 3 SO CF CH CF Br H H H 2 SO CF CH CF HH Br H 0 2 3 2 3 2 3 2 3 SO CF CH CF IHH H 0 SO CF CH CF HH Br H 1 2 3 2 3 2 3 2 3 SO CF CH CF IHH H 1 SO CF CH CF HH Br H 2 2 3 2 3 2 3 2 3 SO CF CH CF IHH H 2 SO CF CH CF HHI H 0 2 3 2 3 2 3 2 3 SO CF CH CF Me H H H 0 SO CF CH CF HHI H 1 2 3 2 3 2 3 2 3 SO CF CH CF Me H H H 1 SO CF CH CF HHI H 2 2 3 2 3 2 3 2 3 SO CF CH CF Me H H H 2 SO CF CH CF HH Me H 0 2 3 2 3 2 3 2 3 SO CF CH CF CF HH H 0 SO CF CH CF HH Me H 1 2 3 2 3 3 2 3 2 3 SO CF CH CF CF HH H 1 SO CF CH CF HH Me H 2 2 3 2 3 3 2 3 2 3 SO CF CH CF CF HH H 2 SO CF CH CF HH CF H 0 2 3 2 3 3 2 3 2 3 3 SO CF CH CF HFH H 0 SO CF CH CF HH CF H 1 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH H 1 SO CF CH CF HH CF H 2 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH H 2 SO CF CH CF HH CF CF H 0 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HClH H 0 SO CF CH CF HH CF CF H 1 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HClH H 1 SO CF CH CF HH CF CF H 2 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HClH H 2 SO CF CH CF HH CF(CF ) H 0 2 3 2 3 2 3 2 3 3 2 SO CF CH CF HBrH H 0 SO CF CH CF HH CF(CF ) H 1 2 3 2 3 2 3 2 3 3 2 SO CF CH CF HBrH H 1 SO CF CH CF HH CF(CF ) H 2 2 3 2 3 2 3 2 3 3 2 SO CF CH CF HBrH H 2 SO CF CH CF HH SMe H 0 2 3 2 3 2 3 2 3 SO CF CH CF HIH H 0 SO CF CH CF HH SMe H 1 2 3 2 3 2 3 2 3 SO CF CH CF HIH H 1 SO CF CH CF HH SMe H 2 2 3 2 3 2 3 2 3 SO CF CH CF HIH H 2 SO CF CH CF HH SOMe H 0 2 3 2 3 2 3 2 3 SO CF CH CF HMeH H 0 SO CF CH CF HH SOMe H 1 2 3 2 3 2 3 2 3 SO CF CH CF HMeH H 1 SO CF CH CF HH SOMe H 2 2 3 2 3 2 3 2 3 SO CF CH CF HMeH H 2 SO CF CH CF HH SO Me H 0 2 3 2 3 2 3 2 3 2 SO CF CH CF HCF HH 0 SO CF CH CF HH SO Me H 1 2 3 2 3 3 2 3 2 3 2 SO CF CH CF HCF HH 1 SO CF CH CF HH SO Me H 2 2 3 2 3 3 2 3 2 3 2 SO CF CH CF HCF HH 2 SO CF CH CF HH OMe H 0 2 3 2 3 3 2 3 2 3 SO CF CH CF HCF CF HH 0 SO CF CH CF HH OMe H 1 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HCF CF HH 1 SO CF CH CF HH OMe H 2 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HCF CF HH 2 SO CF CH CF HH OCF H 0 2 3 2 3 2 3 2 3 2 3 3 SO CF CH CF H CF(CF ) HH 0 SO CF CH CF HH OCF H 1 2 3 2 3 3 2 2 3 2 3 3 SO CF CH CF H CF(CF ) HH 1 SO CF CH CF HH OCF H 2 2 3 2 3 3 2 2 3 2 3 3 SO CF CH CF H CF(CF ) HH 2 SO CF CH CF HH NO H 0 2 3 2 3 3 2 2 3 2 3 2 SO CF CH CF H SMe H H 0 SO CF CH CF HH NO H 1 2 3 2 3 2 3 2 3 2 SO CF CH CF H SMe H H 1 SO CF CH CF HH NO H 2 2 3 2 3 2 3 2 3 2 SO CF CH CF H SMe H H 2 SO CF CH CF HH CN H 0 2 3 2 3 2 3 2 3 SO CF CH CF HSOMeH H 0 SO CF CH CF HH CN H 1 2 3 2 3 2 3 2 3 SO CF CH CF HSOMeH H 1 SO CF CH CF HH CN H 2 2 3 2 3 2 3 2 3 SO CF CH CF HSOMeH H 2 SO CF CH CF HHH F 0 2 3 2 3 2 3 2 3 SO CF CH CF HSO Me H H 0 SO CF CH CF HHH F 1 2 3 2 3 2 2 3 2 3 SO CF CH CF HSO Me H H 1 SO CF CH CF HHH F 2 2 3 2 3 2 2 3 2 3 SO CF CH CF HSO Me H H 2 SO CF CH CF HHH Cl 0 2 3 2 3 2 2 3 2 3 SO CF CH CF H OMe H H 0 SO CF CH CF HHH Cl 1 2 3 2 3 2 3 2 3 SO CF CH CF H OMe H H 1 SO CF CH CF HHH Cl 2 2 3 2 3 2 3 2 3 SO CF CH CF H OMe H H 2 SO CF CH CF HHH Br 0 2 3 2 3 2 3 2 3 SO CF CH CF HOCF HH 0 SO CF CH CF HHH Br 1 2 3 2 3 3 2 3 2 3 SO CF CH CF HOCF HH 1 SO CF CH CF HHH Br 2 2 3 2 3 3 2 3 2 3 SO CF CH CF HOCF HH 2 SO CF CH CF HHH I 0 2 3 2 3 3 2 3 2 3 SO CF CH CF HNO HH 0 SO CF CH CF HHH I 1 2 3 2 3 2 2 3 2 3 Table 1 (Continued) Table 1 (Continued) ［第１表］の続き［第１表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n SO CF CH CF HHH I 2 SO CF CH CF HClH I 0 2 3 2 3 2 3 2 3 SO CF CH CF HHH Me 0 SO CF CH CF HClH I 1 2 3 2 3 2 3 2 3 SO CF CH CF HHH Me 1 SO CF CH CF HClH I 2 2 3 2 3 2 3 2 3 SO CF CH CF HHH Me 2 SO CF CH CF HBrH F 0 2 3 2 3 2 3 2 3 SO CF CH CF HHH CF 0 SO CF CH CF HBrH F 1 2 3 2 3 3 2 3 2 3 SO CF CH CF HHH CF 1 SO CF CH CF HBrH F 2 2 3 2 3 3 2 3 2 3 SO CF CH CF HHH CF 2 SO CF CH CF HBrH Cl 0 2 3 2 3 3 2 3 2 3 SO CF CH CF HHH CF CF 0 SO CF CH CF HBrH Cl 1 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HHH CF CF 1 SO CF CH CF HBrH Cl 2 2 3 2 3 2 3 2 3 2 3 SO CF CH CF HHH CF CF 2 SO CF CH CF HBrH I 0 2 3 2 3 2 3 2 3 2 3 SO CF CH CF H H H CF(CF ) 0 SO CF CH CF HBrH I 1 2 3 2 3 3 2 2 3 2 3 SO CF CH CF H H H CF(CF ) 1 SO CF CH CF HBrH I 2 2 3 2 3 3 2 2 3 2 3 SO CF CH CF H H H CF(CF ) 2 SO CF CH CF HIH F 0 2 3 2 3 3 2 2 3 2 3 SO CF CH CF HHH SMe 0 SO CF CH CF HIH F 1 2 3 2 3 2 3 2 3 SO CF CH CF HHH SMe 1 SO CF CH CF HIH F 2 2 3 2 3 2 3 2 3 SO CF CH CF HHH SMe 2 SO CF CH CF HIH Cl 0 2 3 2 3 2 3 2 3 SO CF CH CF HHH SOMe 0 SO CF CH CF HIH Cl 1 2 3 2 3 2 3 2 3 SO CF CH CF HHH SOMe 1 SO CF CH CF HIH Cl 2 2 3 2 3 2 3 2 3 SO CF CH CF HHH SOMe 2 SO CF CH CF HIH Br 0 2 3 2 3 2 3 2 3 SO CF CH CF HHH SO Me 0 SO CF CH CF HIH Br 1 2 3 2 3 2 2 3 2 3 SO CF CH CF HHH SO Me 1 SO CF CH CF HIH Br 2 2 3 2 3 2 2 3 2 3 SO CF CH CF HHH SO Me 2 SO CF CH CF HFH CN 0 2 3 2 3 2 2 3 2 3 SO CF CH CF HHH OMe 0 SO CF CH CF HFH CN 1 2 3 2 3 2 3 2 3 SO CF CH CF HHH OMe 1 SO CF CH CF HFH CN 2 2 3 2 3 2 3 2 3 SO CF CH CF HHH OMe 2 SO CF CH CF HClH CN 0 2 3 2 3 2 3 2 3 SO CF CH CF HHH OCF 0 SO CF CH CF HClH CN 1 2 3 2 3 3 2 3 2 3 SO CF CH CF HHH OCF 1 SO CF CH CF HClH CN 2 2 3 2 3 3 2 3 2 3 SO CF CH CF HHH OCF 2 SO CF CH CF HBrH CN 0 2 3 2 3 3 2 3 2 3 SO CF CH CF HHH NO 0 SO CF CH CF HBrH CN 1 2 3 2 3 2 2 3 2 3 SO CF CH CF HHH NO 1 SO CF CH CF HBrH CN 2 2 3 2 3 2 2 3 2 3 SO CF CH CF HHH NO 2 SO CF CH CF HIH CN 0 2 3 2 3 2 2 3 2 3 SO CF CH CF HHH CN 0 SO CF CH CF HIH CN 1 2 3 2 3 2 3 2 3 SO CF CH CF HHH CN 1 SO CF CH CF HIH CN 2 2 3 2 3 2 3 2 3 SO CF CH CF HHH CN 2 SO CF CH CF HCF HF 0 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH F 0 SO CF CH CF HCF HF 1 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH F 1 SO CF CH CF HCF HF 2 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH F 2 SO CF CH CF HCF HCl 0 2 3 2 3 2 3 2 3 3 SO CF CH CF HClH Cl 0 SO CF CH CF HCF HCl 1 2 3 2 3 2 3 2 3 3 SO CF CH CF HClH Cl 1 SO CF CH CF HCF HCl 2 2 3 2 3 2 3 2 3 3 SO CF CH CF HClH Cl 2 SO CF CH CF HCF HBr 0 2 3 2 3 2 3 2 3 3 SO CF CH CF HBrH Br 0 SO CF CH CF HCF HBr 1 2 3 2 3 2 3 2 3 3 SO CF CH CF HBrH Br 1 SO CF CH CF HCF HBr 2 2 3 2 3 2 3 2 3 3 SO CF CH CF HBrH Br 2 SO CF CH CF HCF HI 0 2 3 2 3 2 3 2 3 3 SO CF CH CF HIH I 0 SO CF CH CF HCF HI 1 2 3 2 3 2 3 2 3 3 SO CF CH CF HIH I 1 SO CF CH CF HCF HI 2 2 3 2 3 2 3 2 3 3 SO CF CH CF HIH I 2 SO CF CH CF HCF HCN 0 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH Cl 0 SO CF CH CF HCF HCN 1 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH Cl 1 SO CF CH CF HCF HCN 2 2 3 2 3 2 3 2 3 3 SO CF CH CF HFH Cl 2 SO CF CH CF HFF H 0 2 3 2 3 2 3 2 3 SO CF CH CF HFH Br 0 SO CF CH CF HFF H 1 2 3 2 3 2 3 2 3 SO CF CH CF HFH Br 1 SO CF CH CF HFF H 2 2 3 2 3 2 3 2 3 SO CF CH CF HFH Br 2 SO CF CH CF HCl Cl H 0 2 3 2 3 2 3 2 3 SO CF CH CF HFH I 0 SO CF CH CF HCl Cl H 1 2 3 2 3 2 3 2 3 SO CF CH CF HFH I 1 SO CF CH CF HCl Cl H 2 2 3 2 3 2 3 2 3 SO CF CH CF HFH I 2 SO CF CH CF HBr Br H 0 2 3 2 3 2 3 2 3 SO CF CH CF HClH F 0 SO CF CH CF HBr Br H 1 2 3 2 3 2 3 2 3 SO CF CH CF HClH F 1 SO CF CH CF HBr Br H 2 2 3 2 3 2 3 2 3 SO CF CH CF HClH F 2 SO CF CH CF HII H 0 2 3 2 3 2 3 2 3 SO CF CH CF HClH Br 0 SO CF CH CF HII H 1 2 3 2 3 2 3 2 3 SO CF CH CF HClH Br 1 SO CF CH CF HII H 2 2 3 2 3 2 3 2 3 SO CF CH CF HClH Br 2 SO CF CH CF HF Cl H 0 2 3 2 3 2 3 2 3 Table 1 (Continued) ［第１表］の続き W1 R Y1 Y2 Y3 Y4 n SO CF CH CF HF Cl H 1 2 3 2 3 SO CF CH CF HF Cl H 2 2 3 2 3 SO CF CH CF HF Br H 0 2 3 2 3 SO CF CH CF HF Br H 1 2 3 2 3 SO CF CH CF HF Br H 2 2 3 2 3 SO CF CH CF H FIH 0 2 3 2 3 SO CF CH CF H FIH 1 2 3 2 3 SO CF CH CF H FIH 2 2 3 2 3 SO CF CH CF HClF H 0 2 3 2 3 SO CF CH CF HClF H 1 2 3 2 3 SO CF CH CF HClF H 2 2 3 2 3 SO CF CH CF HCl Br H 0 2 3 2 3 SO CF CH CF HCl Br H 1 2 3 2 3 SO CF CH CF HCl Br H 2 2 3 2 3 SO CF CH CF HClI H 0 2 3 2 3 SO CF CH CF HClI H 1 2 3 2 3 SO CF CH CF HClI H 2 2 3 2 3 SO CF CH CF HBrF H 0 2 3 2 3 SO CF CH CF HBrF H 1 2 3 2 3 SO CF CH CF HBrF H 2 2 3 2 3 SO CF CH CF HBr Cl H 0 2 3 2 3 SO CF CH CF HBr Cl H 1 2 3 2 3 SO CF CH CF HBr Cl H 2 2 3 2 3 SO CF CH CF HBrI H 0 2 3 2 3 SO CF CH CF HBrI H 1 2 3 2 3 SO CF CH CF HBrI H 2 2 3 2 3 SO CF CH CF H IFH 0 2 3 2 3 SO CF CH CF H IFH 1 2 3 2 3 SO CF CH CF H IFH 2 2 3 2 3 SO CF CH CF HI Cl H 0 2 3 2 3 SO CF CH CF HI Cl H 1 2 3 2 3 SO CF CH CF HI Cl H 2 2 3 2 3 SO CF CH CF HI Br H 0 2 3 2 3 SO CF CH CF HI Br H 1 2 3 2 3 SO CF CH CF HI Br H 2 2 3 2 3 SO CF CH CF HF CN H 0 2 3 2 3 SO CF CH CF HF CN H 1 2 3 2 3 SO CF CH CF HF CN H 2 2 3 2 3 SO CF CH CF HCl CN H 0 2 3 2 3 SO CF CH CF HCl CN H 1 2 3 2 3 SO CF CH CF HCl CN H 2 2 3 2 3 SO CF CH CF HBr CN H 0 2 3 2 3 SO CF CH CF HBr CN H 1 2 3 2 3 SO CF CH CF HBr CN H 2 2 3 2 3 SO CF CH CF HI CN H 0 2 3 2 3 SO CF CH CF HI CN H 1 2 3 2 3 SO CF CH CF HI CN H 2 2 3 2 3 SO CF CH CF HCF FH 0 2 3 2 3 3 SO CF CH CF HCF FH 1 2 3 2 3 3 SO CF CH CF HCF FH 2 2 3 2 3 3 SO CF CH CF HCF Cl H 0 2 3 2 3 3 SO CF CH CF HCF Cl H 1 2 3 2 3 3 SO CF CH CF HCF Cl H 2 2 3 2 3 3 SO CF CH CF HCF Br H 0 2 3 2 3 3 SO CF CH CF HCF Br H 1 2 3 2 3 3 SO CF CH CF HCF Br H 2 2 3 2 3 3 SO CF CH CF HCF IH 0 2 3 2 3 3 SO CF CH CF HCF IH 1 2 3 2 3 3 SO CF CH CF HCF IH 2 2 3 2 3 3 SO CF CH CF HCF CN H 0 2 3 2 3 3 SO CF CH CF HCF CN H 1 2 3 2 3 3 SO CF CH CF HCF CN H 2 2 3 2 3 3 Table 2 R R R O O O W2 W2 W2 n W1 n W1 n N N N N N N N N N N W3 W3 W3 I Me W4 W4 W2 W2 W2 S W1 n n W1 n N N N N N N N W3 N W3 N W3 F Cl R R O W2 W2 S W1 n W1 n W1 n N N N N N N W3 N W3 N W3 Br W4 O W2 W1 n N W1 N n N N NN N S W2 W1 n W1 n N W1 n W3 N W2 W2 N N N N N N N N N W1 W3 W1 W3 W1 W3 F Cl W4 W4 W2 W2 N N N N N N N N N W1 W3 W1 W3 W1 W3 Br I W4 W4 R R O W2 W2 n N n N N N W1 W3 W1 W3 W1 W3 F W4 W2 S N N n N n N N N N W1 W3 N W1 W3 W1 W3 W4 I W4 W1 n W1 n W1 N n N N N N N N W3 W4 W4 W2 W2 W1 n W1 n N W1 n N N N N W3 N Br I Table 2 (Continued) ［第2 表］の続き W1 R W2 W3 W4 n W 1 R W2 W3 W4 n CF Eｔ HHH 0 CF Eｔ HBr H 0 CF Et HHH 1 CF Et HBr H 1 CF Eｔ HHH 2 CF Eｔ HBr H 2 CF Et FHH 0 CF Et HIH 0 CF Eｔ FHH 1 CF Eｔ HIH 1 CF Et FHH 2 CF Et HIH 2 CF Eｔ Cl H H 0 CF Eｔ HMe H 0 CF Et Cl H H 1 CF Et HMe H 1 CF Eｔ Cl H H 2 CF Eｔ HMe H 2 CF Et Br H H 0 CF Et HCF H 0 3 3 3 CF Eｔ Br H H 1 CF Eｔ HCF H 1 3 3 3 CF Et Br H H 2 CF Et HCF H 2 3 3 3 CF Eｔ IHH 0 CF Eｔ HCF CF H 0 3 3 2 3 CF Et IHH 1 CF Et HCF CF H 1 3 3 2 3 CF Eｔ IHH 2 CF Eｔ HCF CF H 2 3 3 2 3 CF Et Me H H 0 CF Et H CF(CF ) H 0 3 3 3 2 CF Eｔ Me H H 1 CF Eｔ H CF(CF ) H 1 3 3 3 2 CF Et Me H H 2 CF Et H CF(CF ) H 2 3 3 3 2 CF Eｔ CF HH 0 CF Eｔ HSMe H 0 3 3 3 CF Et CF HH 1 CF Et HSMe H 1 3 3 3 CF Eｔ CF HH 2 CF Eｔ HSMe H 2 3 3 3 CF Et CF CF HH 0 CF Et HSOMe H 0 3 2 3 3 CF Eｔ CF CF HH 1 CF Eｔ HSOMe H 1 3 2 3 3 CF Et CF CF HH 2 CF Et HSOMe H 2 3 2 3 3 CF Eｔ CF(CF ) HH 0 CF Eｔ HSO Me H 0 3 3 2 3 2 CF Et CF(CF ) HH 1 CF Et HSO Me H 1 3 3 2 3 2 CF Eｔ CF(CF ) HH 2 CF Eｔ HSO Me H 2 3 3 2 3 2 CF Et SMe H H 0 CF Et HOMe H 0 CF Eｔ SMe H H 1 CF Eｔ HOMe H 1 CF Et SMe H H 2 CF Et HOMe H 2 CF Eｔ SOMe H H 0 CF Eｔ HOCF H 0 3 3 3 CF Et SOMe H H 1 CF Et HOCF H 1 3 3 3 CF Eｔ SOMe H H 2 CF Eｔ HOCF H 2 3 3 3 CF Et SO Me H H 0 CF Et HNO H 0 3 2 3 2 CF Eｔ SO Me H H 1 CF Eｔ HNO H 1 3 2 3 2 CF Et SO Me H H 2 CF Et HNO H 2 3 2 3 2 CF Eｔ OMe H H 0 CF Eｔ HCN H 0 CF Et OMe H H 1 CF Et HCN H 1 CF Eｔ OMe H H 2 CF Eｔ HCN H 2 CF Et OCF HH 0 CF Et HHF 0 3 3 3 CF Eｔ OCF HH 1 CF Eｔ HHF 1 3 3 3 CF Et OCF HH 2 CF Et HHF 2 3 3 3 CF Eｔ NO HH 0 CF Eｔ HH Cl 0 3 2 3 CF Et NO HH 1 CF Et HH Cl 1 3 2 3 CF Eｔ NO HH 2 CF Eｔ HH Cl 2 3 2 3 CF Et CN H H 0 CF Et HH Br 0 CF Eｔ CN H H 1 CF Eｔ HH Br 1 CF Et CN H H 2 CF Et HH Br 2 CF Eｔ HFH 0 CF Eｔ HHI 0 CF Et HFH 1 CF Et HHI 1 CF Eｔ HFH 2 CF Eｔ HHI 2 CF Et HCl H 0 CF Et HH Me 0 CF Eｔ HCl H 1 CF Eｔ HH Me 1 CF Et HCl H 2 CF Et HH Me 2 Table 2 (Continued) Table 2 (Continued) ［第 2 表］の続き［第2表］の続き W1 R W2 W3 W4 n W 1 R W2 W3 W4 n CF Eｔ HH CF 0 CF CF Eｔ HHH 0 3 3 2 3 CF Et HH CF 1 CF CF Et HHH 1 3 3 2 3 CF Eｔ HH CF 2 CF CF Eｔ HHH 2 3 3 2 3 CF Et HH CF CF 0 CF CF Et FHH 0 3 2 3 2 3 CF Eｔ HH CF CF 1 CF CF Eｔ FHH 1 3 2 3 2 3 CF Et HH CF CF 2 CF CF Et FHH 2 3 2 3 2 3 CF Eｔ H H CF(CF ) 0 CF CF Eｔ Cl H H 0 3 3 2 2 3 CF Et H H CF(CF ) 1 CF CF Et Cl H H 1 3 3 2 2 3 CF Eｔ H H CF(CF ) 2 CF CF Eｔ Cl H H 2 3 3 2 2 3 CF Et HH SMe 0 CF CF Et Br H H 0 3 2 3 CF Eｔ HH SMe 1 CF CF Eｔ Br H H 1 3 2 3 CF Et HH SMe 2 CF CF Et Br H H 2 3 2 3 CF Eｔ H H SOMe 0 CF CF Eｔ IHH 0 3 2 3 CF Et H H SOMe 1 CF CF Et IHH 1 3 2 3 CF Eｔ H H SOMe 2 CF CF Eｔ IHH 2 3 2 3 CF Et HH SO Me 0 CF CF Et Me H H 0 3 2 2 3 CF Eｔ HH SO Me 1 CF CF Eｔ Me H H 1 3 2 2 3 CF Et HH SO Me 2 CF CF Et Me H H 2 3 2 2 3 CF Eｔ HH OMe 0 CF CF Eｔ CF HH 0 3 2 3 3 CF Et HH OMe 1 CF CF Et CF HH 1 3 2 3 3 CF Eｔ HH OMe 2 CF CF Eｔ CF HH 2 3 2 3 3 CF Et H H OCF 0 CF CF Et CF CF HH 0 3 3 2 3 2 3 CF Eｔ H H OCF 1 CF CF Eｔ CF CF HH 1 3 3 2 3 2 3 CF Et H H OCF 2 CF CF Et CF CF HH 2 3 3 2 3 2 3 CF Eｔ HH NO 0 CF CF Eｔ CF(CF ) HH 0 3 2 2 3 3 2 CF Et HH NO 1 CF CF Et CF(CF ) HH 1 3 2 2 3 3 2 CF Eｔ HH NO 2 CF CF Eｔ CF(CF ) HH 2 3 2 2 3 3 2 CF Et HH CN 0 CF CF Et SMe H H 0 3 2 3 CF Eｔ HH CN 1 CF CF Eｔ SMe H H 1 3 2 3 CF Et HH CN 2 CF CF Et SMe H H 2 3 2 3 CF CF Eｔ SOMe H H 0 CF CF Et SOMe H H 1 CF CF Eｔ SOMe H H 2 CF CF Et SO Me H H 0 2 3 2 CF CF Eｔ SO Me H H 1 2 3 2 CF CF Et SO Me H H 2 2 3 2 CF CF Eｔ OMe H H 0 CF CF Et OMe H H 1 CF CF Eｔ OMe H H 2 CF CF Et OCF HH 0 2 3 3 CF CF Eｔ OCF HH 1 2 3 3 CF CF Et OCF HH 2 2 3 3 CF CF Eｔ NO HH 0 2 3 2 CF CF Et NO HH 1 2 3 2 CF CF Eｔ NO HH 2 2 3 2 CF CF Et CN H H 0 CF CF Eｔ CN H H 1 CF CF Et CN H H 2 CF CF Eｔ HFH 0 CF CF Et HFH 1 CF CF Eｔ HFH 2 CF CF Et HClH 0 CF CF Eｔ HClH 1 CF CF Et HClH 2 Table 2 (Continued) Table 2 (Continued) ［第 2表］の続き［第 2表］の続き W1 R W2 W 3 W4 n W 1 R W2 W3 W4 n CF CF Eｔ HBrH 0 CF CF Eｔ HH CF 0 2 3 2 3 3 CF CF Et HBrH 1 CF CF Et HH CF 1 2 3 2 3 3 CF CF Eｔ HBrH 2 CF CF Eｔ HH CF 2 2 3 2 3 3 CF CF Et HIH 0 CF CF Et HH CF CF 0 2 3 2 3 2 3 CF CF Eｔ HIH 1 CF CF Eｔ HH CF CF 1 2 3 2 3 2 3 CF CF Et HIH 2 CF CF Et HH CF CF 2 2 3 2 3 2 3 CF CF Eｔ HMeH 0 CF CF Eｔ HH CF(CF ) 0 2 3 2 3 3 2 CF CF Et HMeH 1 CF CF Et HH CF(CF ) 1 2 3 2 3 3 2 CF CF Eｔ HMeH 2 CF CF Eｔ HH CF(CF ) 2 2 3 2 3 3 2 CF CF Et HCF H 0 CF CF Et HH SMe 0 2 3 3 2 3 CF CF Eｔ HCF H 1 CF CF Eｔ HH SMe 1 2 3 3 2 3 CF CF Et HCF H 2 CF CF Et HH SMe 2 2 3 3 2 3 CF CF Eｔ HCF CF H 0 CF CF Eｔ H H SOMe 0 2 3 2 3 2 3 CF CF Et HCF CF H 1 CF CF Et H H SOMe 1 2 3 2 3 2 3 CF CF Eｔ HCF CF H 2 CF CF Eｔ H H SOMe 2 2 3 2 3 2 3 CF CF Et HCF(CF ) H 0 CF CF Et HH SO Me 0 2 3 3 2 2 3 2 CF CF Eｔ HCF(CF ) H 1 CF CF Eｔ HH SO Me 1 2 3 3 2 2 3 2 CF CF Et HCF(CF ) H 2 CF CF Et HH SO Me 2 2 3 3 2 2 3 2 CF CF Eｔ HSMe H 0 CF CF Eｔ HH OMe 0 2 3 2 3 CF CF Et HSMe H 1 CF CF Et HH OMe 1 2 3 2 3 CF CF Eｔ HSMe H 2 CF CF Eｔ HH OMe 2 2 3 2 3 CF CF Et HSOMeH 0 CF CF Et HH OCF 0 2 3 2 3 3 CF CF Eｔ HSOMeH 1 CF CF Eｔ HH OCF 1 2 3 2 3 3 CF CF Et HSOMeH 2 CF CF Et HH OCF 2 2 3 2 3 3 CF CF Eｔ HSO Me H 0 CF CF Eｔ HH NO 0 2 3 2 2 3 2 CF CF Et HSO Me H 1 CF CF Et HH NO 1 2 3 2 2 3 2 CF CF Eｔ HSO Me H 2 CF CF Eｔ HH NO 2 2 3 2 2 3 2 CF CF Et HOMe H 0 CF CF Et HH CN 0 2 3 2 3 CF CF Eｔ HOMe H 1 CF CF Eｔ HH CN 1 2 3 2 3 CF CF Et HOMe H 2 CF CF Et HH CN 2 2 3 2 3 CF CF Eｔ HOCF H 0 2 3 3 CF CF Et HOCF H 1 2 3 3 CF CF Eｔ HOCF H 2 2 3 3 CF CF Et HNO H 0 2 3 2 CF CF Eｔ HNO H 1 2 3 2 CF CF Et HNO H 2 2 3 2 CF CF Eｔ HCNH 0 CF CF Et HCNH 1 CF CF Eｔ HCNH 2 CF CF Et HHF 0 CF CF Eｔ HHF 1 CF CF Et HHF 2 CF CF Eｔ HH Cl 0 CF CF Et HH Cl 1 CF CF Eｔ HH Cl 2 CF CF Et HH Br 0 CF CF Eｔ HH Br 1 CF CF Et HH Br 2 CF CF Eｔ HHI 0 CF CF Et HHI 1 CF CF Eｔ HHI 2 CF CF Et HH Me 0 CF CF Eｔ HH Me 1 CF CF Et HH Me 2 Table 3 Table 3 (Continued) ［第3表］の続き W1 R Y5 Y 6 n W 1 R Y5 Y 6 n CF Eｔ HH 0 CF CF Eｔ HH 0 3 2 3 CF Et HH 1 CF CF Et HH 1 3 2 3 CF Eｔ HH 2 CF CF Eｔ HH 2 3 2 3 CF Et HF 0 CF CF Et HF 0 3 2 3 CF Eｔ HF 1 CF CF Eｔ HF 1 3 2 3 CF Et HF 2 CF CF Et HF 2 3 2 3 CF Eｔ HCl 0 CF CF Eｔ HCl 0 3 2 3 CF Et HCl 1 CF CF Et HCl 1 3 2 3 CF Eｔ HCl 2 CF CF Eｔ HCl 2 3 2 3 CF Et HBr 0 CF CF Et HBr 0 3 2 3 CF Eｔ HBr 1 CF CF Eｔ HBr 1 3 2 3 CF Et HBr 2 CF CF Et HBr 2 3 2 3 CF Eｔ HI 0 CF CF Eｔ HI 0 3 2 3 CF Et HI 1 CF CF Et HI 1 3 2 3 CF Eｔ HI 2 CF CF Eｔ HI 2 3 2 3 CF Et HMe 0 CF CF Et HMe 0 3 2 3 CF Eｔ HMe 1 CF CF Eｔ HMe 1 3 2 3 CF Et HMe 2 CF CF Et HMe 2 3 2 3 CF Eｔ HCF 0 CF CF Eｔ HCF 0 3 3 2 3 3 CF Et HCF 1 CF CF Et HCF 1 3 3 2 3 3 CF Eｔ HCF 2 CF CF Eｔ HCF 2 3 3 2 3 3 CF Et HCF CF 0 CF CF Et HCF CF 0 3 2 3 2 3 2 3 CF Eｔ HCF CF 1 CF CF Eｔ HCF CF 1 3 2 3 2 3 2 3 CF Et HCF CF 2 CF CF Et HCF CF 2 3 2 3 2 3 2 3 CF Eｔ H CF(CF ) 0 CF CF Eｔ H CF(CF ) 0 3 3 2 2 3 3 2 CF Et H CF(CF ) 1 CF CF Et H CF(CF ) 1 3 3 2 2 3 3 2 CF Eｔ H CF(CF ) 2 CF CF Eｔ H CF(CF ) 2 3 3 2 2 3 3 2 CF Et HSMe 0 CF CF Et HSMe 0 3 2 3 CF Eｔ HSMe 1 CF CF Eｔ HSMe 1 3 2 3 CF Et HSMe 2 CF CF Et HSMe 2 3 2 3 CF Eｔ H SOMe 0 CF CF Eｔ H SOMe 0 3 2 3 CF Et H SOMe 1 CF CF Et H SOMe 1 3 2 3 CF Eｔ H SOMe 2 CF CF Eｔ H SOMe 2 3 2 3 CF Et HSO Me 0 CF CF Et HSO Me 0 3 2 2 3 2 CF Eｔ HSO Me 1 CF CF Eｔ HSO Me 1 3 2 2 3 2 CF Et HSO Me 2 CF CF Et HSO Me 2 3 2 2 3 2 CF Eｔ HOMe 0 CF CF Eｔ HOMe 0 3 2 3 CF Et HOMe 1 CF CF Et HOMe 1 3 2 3 CF Eｔ HOMe 2 CF CF Eｔ HOMe 2 3 2 3 CF Et H OCF 0 CF CF Et H OCF 0 3 3 2 3 3 CF Eｔ H OCF 1 CF CF Eｔ H OCF 1 3 3 2 3 3 CF Et H OCF 2 CF CF Et H OCF 2 3 3 2 3 3 CF Eｔ HNO 0 CF CF Eｔ HNO 0 3 2 2 3 2 CF Et HNO 1 CF CF Et HNO 1 3 2 2 3 2 CF Eｔ HNO 2 CF CF Eｔ HNO 2 3 2 2 3 2 CF Et HCN 0 CF CF Et HCN 0 3 2 3 CF Eｔ HCN 1 CF CF Eｔ HCN 1 3 2 3 CF Et HCN 2 CF CF Et HCN 2 3 2 3 Table 4 S S S W1 n W1 n W1 n N N N N N N N Y6 Y6 Y6 NN NN NN N S N S N S Br Me R R R S S S N N N N N N N N Y6 Y6 N S N S N S W1 W1 F Cl N N N N N N N N Y6 Y6 N S N S W1 W1 Br Me R R R S S S n N n n N N N N Y6 Y6 Y6 N N N N S N S N S W1 W1 W1 N n N N N n N N N N W1 N S I Me W1 n W1 n W1 n N N N N N Y6 N Y6 N Y6 N S N S W1 W1 n W1 n n N N N N N Y6 N Y6 N Y6 N S N S I Me W1 n W1 n N N W1 n N N N N Y6 N Y6 N Y6 N S N N N S O O R W1 n W1 n N N N N W1 n N Y6 N Y6 N Y6 N N N S Br I S S S W1 n n W1 n N N N N N Y6 N Y6 N Y6 N N N N S N S N S 1 1 1 S S S W1 n W1 n W1 n N N N N N N N N N N Y6 N Y6 N Y6 N N N N S N S N S Br I Table 4 (Continued) ［第4 表］の続き W1 R Y6 n W1 R Y6 n CF Eｔ H 0 CF CF Eｔ H 0 3 2 3 CF Et H 1 CF CF Et H 1 3 2 3 CF Eｔ H 2 CF CF Eｔ H 2 3 2 3 CF Et F 0 CF CF Et F 0 3 2 3 CF Eｔ F 1 CF CF Eｔ F 1 3 2 3 CF Et F 2 CF CF Et F 2 3 2 3 CF Eｔ Cl 0 CF CF Eｔ Cl 0 3 2 3 CF Et Cl 1 CF CF Et Cl 1 3 2 3 CF Eｔ Cl 2 CF CF Eｔ Cl 2 3 2 3 CF Et Br 0 CF CF Et Br 0 3 2 3 CF Eｔ Br 1 CF CF Eｔ Br 1 3 2 3 CF Et Br 2 CF CF Et Br 2 3 2 3 CF Eｔ I 0 CF CF Eｔ I 0 3 2 3 CF Et I 1 CF CF Et I 1 3 2 3 CF Eｔ I 2 CF CF Eｔ I 2 3 2 3 CF Et Me 0 CF CF Et Me 0 3 2 3 CF Eｔ Me 1 CF CF Eｔ Me 1 3 2 3 CF Et Me 2 CF CF Et Me 2 3 2 3 CF Eｔ CF 0 CF CF Eｔ CF 0 3 3 2 3 3 CF Et CF 1 CF CF Et CF 1 3 3 2 3 3 CF Eｔ CF 2 CF CF Eｔ CF 2 3 3 2 3 3 CF Et CF CF 0 CF CF Et CF CF 0 3 2 3 2 3 2 3 CF Eｔ CF CF 1 CF CF Eｔ CF CF 1 3 2 3 2 3 2 3 CF Et CF CF 2 CF CF Et CF CF 2 3 2 3 2 3 2 3 CF Eｔ CF(CF ) 0 CF CF Eｔ CF(CF ) 0 3 3 2 2 3 3 2 CF Et CF(CF ) 1 CF CF Et CF(CF ) 1 3 3 2 2 3 3 2 CF Eｔ CF(CF ) 2 CF CF Eｔ CF(CF ) 2 3 3 2 2 3 3 2 CF Et SMe 0 CF CF Et SMe 0 3 2 3 CF Eｔ SMe 1 CF CF Eｔ SMe 1 3 2 3 CF Et SMe 2 CF CF Et SMe 2 3 2 3 CF Eｔ SOMe 0 CF CF Eｔ SOMe 0 3 2 3 CF Et SOMe 1 CF CF Et SOMe 1 3 2 3 CF Eｔ SOMe 2 CF CF Eｔ SOMe 2 3 2 3 CF Et SO Me 0 CF CF Et SO Me 0 3 2 2 3 2 CF Eｔ SO Me 1 CF CF Eｔ SO Me 1 3 2 2 3 2 CF Et SO Me 2 CF CF Et SO Me 2 3 2 2 3 2 CF Eｔ OMe 0 CF CF Eｔ OMe 0 3 2 3 CF Et OMe 1 CF CF Et OMe 1 3 2 3 CF Eｔ OMe 2 CF CF Eｔ OMe 2 3 2 3 CF Et OCF 0 CF CF Et OCF 0 3 3 2 3 3 CF Eｔ OCF 1 CF CF Eｔ OCF 1 3 3 2 3 3 CF Et OCF 2 CF CF Et OCF 2 3 3 2 3 3 CF Eｔ NO 0 CF CF Eｔ NO 0 3 2 2 3 2 CF Et NO 1 CF CF Et NO 1 3 2 2 3 2 CF Eｔ NO 2 CF CF Eｔ NO 2 3 2 2 3 2 CF Et CN 0 CF CF Et CN 0 3 2 3 CF Eｔ CN 1 CF CF Eｔ CN 1 3 2 3 CF Et CN 2 CF CF Et CN 2 3 2 3 Table 5 R R R O O O Y1 Y1 Y1 W1 Y2 W1 n Y2 n W1 n Y2 N N O N S N Y3 Y3 Y3 Me Me Me Y4 Y4 R R R O O O Y1 Y1 Y1 S S S W1 n Y2 W1 n Y2 W1 n Y2 N N O N S N N Y3 N Y3 N Y3 Me Me Me Me Y4 Y4 Y1 S W1 n Y2 W1 n Y2 W1 Y2 N O N Y3 Me Y4 Me Y4 Y1 S n Y2 n Y2 n Y2 N N W1 Y3 W1 Y3 W1 Y3 Me Me Y4 Y4 Y1 Y1 N n Y2 N N n Y2 n Y2 O N S N W1 Y3 W1 Y3 W1 Y3 Me Y4 Y4 1 1 1 Y1 Y1 S S S W1 n Y2 W1 Y2 W1 n Y2 N N N N N O N N Y3 N Y3 N Y3 Me Me Me Y4 Y4 Y4 R R R Y1 Y1 W1 n Y2 W1 n Y2 W1 n Y2 N N Y3 Y3 Y3 Cl Me Me F Me Y4 Y4 Y1 Y1 W1 n Y2 W1 n Y2 W1 n Y2 Y3 Y3 Br Me I Me Me Y4 Y4 Y1 S W1 n Y2 W1 n Y2 W1 n Y2 N N Y3 N Y3 N Y3 Cl Me F Me Y4 Y4 Y1 S W1 n Y2 W1 n Y2 W1 n Y2 N N Y3 N Y3 N Y3 I Me Me Br Me Y4 Y4 Y1 S W1 n Y2 W1 n Y2 W1 n Y2 N Y3 F Me Me Me Y 4 Y4 Y1 S W1 n Y2 W1 n Y2 N W1 n Y2 S N Y3 N Y3 N Y3 Y1 S W1 n Y2 W1 n Y2 W1 n Y2 N S N Y3 N Y3 N Y3 Br Y4 Y1 Y1 W1 n Y2 W1 Y2 W1 n Y2 NN NN Y3 Y3 Y4 Y4 Y1 Y1 W1 Y2 W1 n Y2 n W1 n Y2 N NN NN Y3 Y3 Br Me Y4 Y4 1 1 R R R O Y1 Y1 n Y2 n Y2 n Y2 N S S W1 Y3 W1 Y3 W1 Y3 Y4 Y4 1 1 R R R O Y1 Y1 S n Y2 n Y2 n Y2 N S S W1 Y3 W1 Y3 W1 Y3 Br I Y4 Y4 Y1 Y1 N Y2 N Y2 N n Y2 n n N W1 Y3 W1 Y3 W1 Y3 Y4 Y4 Y1 Y1 N Y2 N Y2 n Y2 n n N W1 Y3 W1 Y3 W1 Y3 Br I Y4 Y4 O O O Y1 Y1 W1 n Y2 W1 n Y2 W1 n Y2 Y3 Y3 Y4 Y4 Y1 Y1 W1 Y2 W1 n Y2 W1 n Y2 n Y3 Y3 Br I Y4 Y4 Y1 Y1 W1 n Y2 W1 n Y2 W1 n Y2 N N Y3 N Y3 N Y3 Y 4 Y 4 Table 4 (Continued) ［第 4表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y3 Y4 n CF Et HHHH 0 CF Et HNO HH 1 3 3 2 CF Et HHHH 1 CF Et HNO HH 2 3 3 2 CF Et HHHH 2 CF Et HCN H H 0 CF Et FHHH 0 CF Et HCN H H 1 CF Et FHHH 1 CF Et HCN H H 2 CF Et FHHH 2 CF Et HHFH 0 CF Et Cl HHH 0 CF Et HHFH 1 CF Et Cl HHH 1 CF Et HHFH 2 CF Et Cl HHH 2 CF Et HH Cl H 0 CF Et Br HHH 0 CF Et HH Cl H 1 CF Et Br HHH 1 CF Et HH Cl H 2 CF Et Br HHH 2 CF Et HH Br H 0 CF Et IHHH 0 CF Et HH Br H 1 CF Et IHHH 1 CF Et HH Br H 2 CF Et IHHH 2 CF Et HHIH 0 CF Et Me HHH 0 CF Et HHIH 1 CF Et Me HHH 1 CF Et HHIH 2 CF Et Me HHH 2 CF Et HH Me H 0 CF Et CF HHH 0 CF Et HH Me H 1 3 3 3 CF Et CF HHH 1 CF Et HH Me H 2 3 3 3 CF Et CF HHH 2 CF Et HH CF H 0 3 3 3 3 CF Et HFHH 0 CF Et HH CF H 1 3 3 3 CF Et HFHH 1 CF Et HH CF H 2 3 3 3 CF Et HFHH 2 CF Et HH CF CF H 0 3 3 2 3 CF Et HCl H H 0 CF Et HH CF CF H 1 3 3 2 3 CF Et HCl H H 1 CF Et HH CF CF H 2 3 3 2 3 CF Et HCl H H 2 CF Et HH CF(CF ) H 0 3 3 3 2 CF Et HBr H H 0 CF Et HH CF(CF ) H 1 3 3 3 2 CF Et HBr H H 1 CF Et HH CF(CF ) H 2 3 3 3 2 CF Et HBr H H 2 CF Et H H SMe H 0 CF Et HIHH 0 CF Et H H SMe H 1 CF Et HIHH 1 CF Et H H SMe H 2 CF Et HIHH 2 CF Et H H SOMe H 0 CF Et HMe H H 0 CF Et H H SOMe H 1 CF Et HMe H H 1 CF Et H H SOMe H 2 CF Et HMe H H 2 CF Et HH SO Me H 0 3 3 2 CF Et HCF HH 0 CF Et HH SO Me H 1 3 3 3 2 CF Et HCF HH 1 CF Et HH SO Me H 2 3 3 3 2 CF Et HCF HH 2 CF Et H H OMe H 0 3 3 3 CF Et HCF CF HH 0 CF Et H H OMe H 1 3 2 3 3 CF Et HCF CF HH 1 CF Et H H OMe H 2 3 2 3 3 CF Et HCF CF HH 2 CF Et H H OCF H 0 3 2 3 3 3 CF Et H CF(CF ) HH 0 CF Et H H OCF H 1 3 3 2 3 3 CF Et H CF(CF ) HH 1 CF Et H H OCF H 2 3 3 2 3 3 CF Et H CF(CF ) HH 2 CF Et HH NO H 0 3 3 2 3 2 CF Et H SMe H H 0 CF Et HH NO H 1 3 3 2 CF Et H SMe H H 1 CF Et HH NO H 2 3 3 2 CF Et H SMe H H 2 CF Et HH CN H 0 CF Et H SOMe H H 0 CF Et HH CN H 1 CF Et H SOMe H H 1 CF Et HH CN H 2 CF Et H SOMe H H 2 CF Et HHHF 0 CF Et HSO Me H H 0 CF Et HHHF 1 3 2 3 CF Et HSO Me H H 1 CF Et HHHF 2 3 2 3 CF Et HSO Me H H 2 CF Et HHH Cl 0 3 2 3 CF Et H OMe H H 0 CF Et HHH Cl 1 CF Et H OMe H H 1 CF Et HHH Cl 2 CF Et H OMe H H 2 CF Et HHH Br 0 CF Et HOCF HH 0 CF Et HHH Br 1 3 3 3 CF Et HOCF HH 1 CF Et HHH Br 2 3 3 3 CF Et HOCF HH 2 CF Et HHHI 0 3 3 3 CF Et HNO HH 0 CF Et HHHI 1 3 2 3 Table 5 (Continued) Table 5 (Continued) ［第 5 表］の続き［第 5表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n CF Et HHH I 2 CF CF Et HHH H 0 3 2 3 CF Et HHH Me 0 CF CF Et HHH H 1 3 2 3 CF Et HHH Me 1 CF CF Et HHH H 2 3 2 3 CF Et HHH Me 2 CF CF Et FHH H 0 3 2 3 CF Et HHH CF 0 CF CF Et FHH H 1 3 3 2 3 CF Et HHH CF 1 CF CF Et FHH H 2 3 3 2 3 CF Et HHH CF 2 CF CF Et Cl H H H 0 3 3 2 3 CF Et HHH CF CF 0 CF CF Et Cl H H H 1 3 2 3 2 3 CF Et HHH CF CF 1 CF CF Et Cl H H H 2 3 2 3 2 3 CF Et HHH CF CF 2 CF CF Et Br H H H 0 3 2 3 2 3 CF Et H H H CF(CF ) 0 CF CF Et Br H H H 1 3 3 2 2 3 CF Et H H H CF(CF ) 1 CF CF Et Br H H H 2 3 3 2 2 3 CF Et H H H CF(CF ) 2 CF CF Et IHH H 0 3 3 2 2 3 CF Et HHH SMe 0 CF CF Et IHH H 1 3 2 3 CF Et HHH SMe 1 CF CF Et IHH H 2 3 2 3 CF Et HHH SMe 2 CF CF Et Me H H H 0 3 2 3 CF Et HHH SOMe 0 CF CF Et Me H H H 1 3 2 3 CF Et HHH SOMe 1 CF CF Et Me H H H 2 3 2 3 CF Et HHH SOMe 2 CF CF Et CF HH H 0 3 2 3 3 CF Et HHH SO Me 0 CF CF Et CF HH H 1 3 2 2 3 3 CF Et HHH SO Me 1 CF CF Et CF HH H 2 3 2 2 3 3 CF Et HHH SO Me 2 CF CF Et HFH H 0 3 2 2 3 CF Et HHH OMe 0 CF CF Et HFH H 1 3 2 3 CF Et HHH OMe 1 CF CF Et HFH H 2 3 2 3 CF Et HHH OMe 2 CF CF Et HClH H 0 3 2 3 CF Et HHH OCF 0 CF CF Et HClH H 1 3 3 2 3 CF Et HHH OCF 1 CF CF Et HClH H 2 3 3 2 3 CF Et HHH OCF 2 CF CF Et HBrH H 0 3 3 2 3 CF Et HHH NO 0 CF CF Et HBrH H 1 3 2 2 3 CF Et HHH NO 1 CF CF Et HBrH H 2 3 2 2 3 CF Et HHH NO 2 CF CF Et HIH H 0 3 2 2 3 CF Et HHH CN 0 CF CF Et HIH H 1 3 2 3 CF Et HHH CN 1 CF CF Et HIH H 2 3 2 3 CF Et HHH CN 2 CF CF Et HMeH H 0 3 2 3 CF CF Et HMeH H 1 CF CF Et HMeH H 2 CF CF Et HCF HH 0 2 3 3 CF CF Et HCF HH 1 2 3 3 CF CF Et HCF HH 2 2 3 3 CF CF Et HCF CF HH 0 2 3 2 3 CF CF Et HCF CF HH 1 2 3 2 3 CF CF Et HCF CF HH 2 2 3 2 3 CF CF Et H CF(CF ) HH 0 2 3 3 2 CF CF Et H CF(CF ) HH 1 2 3 3 2 CF CF Et H CF(CF ) HH 2 2 3 3 2 CF CF Et HSMe H H 0 CF CF Et HSMe H H 1 CF CF Et HSMe H H 2 CF CF Et HSOMeH H 0 CF CF Et HSOMeH H 1 CF CF Et HSOMeH H 2 CF CF Et HSO Me H H 0 2 3 2 CF CF Et HSO Me H H 1 2 3 2 CF CF Et HSO Me H H 2 2 3 2 CF CF Et HOMe H H 0 CF CF Et HOMe H H 1 CF CF Et HOMe H H 2 CF CF Et HOCF HH 0 2 3 3 CF CF Et HOCF HH 1 2 3 3 CF CF Et HOCF HH 2 2 3 3 CF CF Et HNO HH 0 2 3 2 Table 5 (Continued) Table 5 (Continued) ［第 5 表］の続き［第 5表］の続き W1 R Y1 Y2 Y3 Y4 n W1 R Y1 Y2 Y 3 Y 4 n CF CF Et HNO HH 1 CF CF Et HHH I 2 2 3 2 2 3 CF CF Et HNO HH 2 CF CF Et HHH Me 0 2 3 2 2 3 CF CF Et HCNH H 0 CF CF Et HHH Me 1 2 3 2 3 CF CF Et HCNH H 1 CF CF Et HHH Me 2 2 3 2 3 CF CF Et HCNH H 2 CF CF Et HHH CF 0 2 3 2 3 3 CF CF Et HHF H 0 CF CF Et HHH CF 1 2 3 2 3 3 CF CF Et HHF H 1 CF CF Et HHH CF 2 2 3 2 3 3 CF CF Et HHF H 2 CF CF Et HHH CF CF 0 2 3 2 3 2 3 CF CF Et HH Cl H 0 CF CF Et HHH CF CF 1 2 3 2 3 2 3 CF CF Et HH Cl H 1 CF CF Et HHH CF CF 2 2 3 2 3 2 3 CF CF Et HH Cl H 2 CF CF Et HHH CF(CF ) 0 2 3 2 3 3 2 CF CF Et HH Br H 0 CF CF Et HHH CF(CF ) 1 2 3 2 3 3 2 CF CF Et HH Br H 1 CF CF Et HHH CF(CF ) 2 2 3 2 3 3 2 CF CF Et HH Br H 2 CF CF Et HHH SMe 0 2 3 2 3 CF CF Et HHI H 0 CF CF Et HHH SMe 1 2 3 2 3 CF CF Et HHI H 1 CF CF Et HHH SMe 2 2 3 2 3 CF CF Et HHI H 2 CF CF Et H H H SOMe 0 2 3 2 3 CF CF Et HH Me H 0 CF CF Et H H H SOMe 1 2 3 2 3 CF CF Et HH Me H 1 CF CF Et H H H SOMe 2 2 3 2 3 CF CF Et HH Me H 2 CF CF Et HHH SO Me 0 2 3 2 3 2 CF CF Et HH CF H 0 CF CF Et HHH SO Me 1 2 3 3 2 3 2 CF CF Et HH CF H 1 CF CF Et HHH SO Me 2 2 3 3 2 3 2 CF CF Et HH CF H 2 CF CF Et HHH OMe 0 2 3 3 2 3 CF CF Et HH CF CF H 0 CF CF Et HHH OMe 1 2 3 2 3 2 3 CF CF Et HH CF CF H 1 CF CF Et HHH OMe 2 2 3 2 3 2 3 CF CF Et HH CF CF H 2 CF CF Et HHH OCF 0 2 3 2 3 2 3 3 CF CF Et H H CF(CF ) H 0 CF CF Et HHH OCF 1 2 3 3 2 2 3 3 CF CF Et H H CF(CF ) H 1 CF CF Et HHH OCF 2 2 3 3 2 2 3 3 CF CF Et H H CF(CF ) H 2 CF CF Et HHH NO 0 2 3 3 2 2 3 2 CF CF Et HH SMe H 0 CF CF Et HHH NO 1 2 3 2 3 2 CF CF Et HH SMe H 1 CF CF Et HHH NO 2 2 3 2 3 2 CF CF Et HH SMe H 2 CF CF Et HHH CN 0 2 3 2 3 CF CF Et H H SOMe H 0 CF CF Et HHH CN 1 2 3 2 3 CF CF Et H H SOMe H 1 CF CF Et HHH CN 2 2 3 2 3 CF CF Et H H SOMe H 2 CF CF Et HH SO Me H 0 2 3 2 CF CF Et HH SO Me H 1 2 3 2 CF CF Et HH SO Me H 2 2 3 2 CF CF Et HH OMe H 0 CF CF Et HH OMe H 1 CF CF Et HH OMe H 2 CF CF Et H H OCF H 0 2 3 3 CF CF Et H H OCF H 1 2 3 3 CF CF Et H H OCF H 2 2 3 3 CF CF Et HH NO H 0 2 3 2 CF CF Et HH NO H 1 2 3 2 CF CF Et HH NO H 2 2 3 2 CF CF Et HH CN H 0 CF CF Et HH CN H 1 CF CF Et HH CN H 2 CF CF Et HHH F 0 CF CF Et HHH F 1 CF CF Et HHH F 2 CF CF Et HHH Cl 0 CF CF Et HHH Cl 1 CF CF Et HHH Cl 2 CF CF Et HHH Br 0 CF CF Et HHH Br 1 CF CF Et HHH Br 2 CF CF Et HHH I 0 CF CF Et HHH I 1 The pesticides herein mean pesticides for controlling harmful arthropods in agricultural fields or in zootechnical/hygienic fields (internal/external parasites in or on mammals and birds as livestock and pets, and domestic or industrial hygienic insects/nuisance insects). Further, the agricultural chemicals herein mean insecticides/acaricides, nematicides, herbicides and fungicides in agricultural fields.

The insects, mites, crustaceans, mollusks and nematodes that the compounds of the present invention can control specifically include the following organisms, but the present invention is not restricted thereto.

Insects of the order Lepidoptera such as Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Archips fuscocupreanus, Grapholita molesta, Homona magnanima, Leguminivora glycinivorella, Matsumuraeses phaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Lyonetia prunifoliella malinella, Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda masinissa, Helcystogramma triannulella, Pectinophora gossypiella, Carposina sasakii, Cydla pomonella, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diaphania indica, Etiella zinckenella, Glyphodes pyloalis, Hellula undalis, Ostrinia furnacalis, Ostrinia scapulalis, Ostrinia nubilalis, Parapediasia teterrella, Parnara guttata, Pieris brassicae, Pieris rapae crucivora, Ascotis selenaria, Pseudoplusia includens, Euproctis pseudoconspersa, Lymantria dispar, Orgyia thyellina, Hyphantria cunea, Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Mamestra brassicae, Mythimna separata, Naranga aenescens, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera depravata, Trichoplusia ni, Endopiza viteana, Manduca quinquemaculata and Manduca sexta.

Insects of the order Thysanoptera such as Frankliniella intonsa, Frankliniella occidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci and Ponticulothrips diospyrosi.

Insects of the order Hemiptera such as Dolycoris baccarum, Eurydema rugosum, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glaucias subpunctatus, Halyomorpha halys, Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia crossota, Scotinophora lurida, Cletus punctiger, Leptocorisa chinensis, Riptortus clavatus, Rhopalus msculatus, Cavelerius saccharivorus, Togo hemipterus, Dysdercus cingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium, Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Macrosteles striifrons, Nephotettix cinctinceps, Psuedatomoscelis seriatus, Laodelphax striatella, Nilaparvata lugens, Sogatella furcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, Viteus vitifolii, Aphis gossypii, Aphis spiraecola, Myzus persicae, Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Planococcus citri, Planococcus kuraunhiae, Pseudococcus comstocki, Ceroplastes ceriferus, Ceroplastes rubens, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis euonymi, Unaspis yanonensis and Cimex lectularius.

Insects of the order Coleoptera such as Anomala cuprea, Anomala rufocuprea, Gametis jucunda, Heptophylla picea, Popillia japonica, Lepinotarsa decemlineata, Melanotus fortnumi, Melanotus tamsuyensis, Lasioderma serricorne, Epuraea domina, Epilachna varivestis, Epilachna vigintioctopunctata, Tenebrio molitor, Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchus chinensis, Aulacophora femoralis, Chaetocnema concinna, Diabrotica undecimpunctata, Diabrotica virgifera, Diabrotica barberi, Oulema oryzae, Phyllotreta striolata, Psylliodes angusticollis, Rhynchites heros, Cylas formicarius, Anthonomus grandis, Echinocnemus squameus, Euscepes postfasciatus, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus vestitus and Paederus fuscipes.

Insects of the order Diptera such as Asphondylia yushimai, Sitodiplosis mosellana, Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis capitata, Hydrellia griseola, Drosophila suzukii, Agromyza oryzae, Chromatomyia horticola, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii, Delia platura, Pegomya cunicularia, Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans, Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanus trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens, Aedes aegypti, Aedes albopicutus and Anopheles hyracanus sinesis.

Insects of the order Hymenoptera such as Apethymus kuri, Athalia rosae, Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti, Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp. and Monomorium pharaonis.

Insects of the order Orthoptera such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis and Schistocerca gregaria.

Insects of the order Collembola such as Onychiurus folsomi, Onychiurus sibiricus and Bourletiella hortensis.

Insects of the order Dictyoptera such as Periplaneta fuliginosa, Periplaneta japonica and Blattella germanica.

Insects of the order Isoptera such as Coptotermes formosanus, Reticulitermes speratus and Odontotermes formosanus.

Insects of the order Siphonaptera such as Ctenocephalidae felis, Ctenocephalides canis, Echidnophaga gallinacea, Pulex irritans and Xenopsylla cheopis.

Insects of the order Mallophaga such as Menacanthus stramineus and Bovicola bovis.

Insects of the order Anoplura such as Haematopinus eurysternus, Haematopinus suis, Linognathus vituli and Solenopotes capillatus.

Tarsonemidae mites such as Phytonemus pallidus, Polyphagotarsonemus latus and Tarsonemus bilobatus.

Eupodidae mites such as Penthaleus erythrocephalus and Penthaleus major.

Tetranychidae mites such as Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai and Tetranychus urticae.

Eriophyidae mites such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis and Phyllocoptruta oleivora.

Acaridae mites such as Rhizoglyphus robini, Tyrophagus putrescentiae and Tyrophagus similis.

Bee mites such as Varroa jacobsoni.

Ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemophysalis flava, Haemophysalis campanulata, Ixodes ovatus, Ixodes persulcatus, Amblyomma spp.and Dermacentor spp.

Mites of the suborder Mesostigmata such as red mite (Dermanyssus gallinae), tropical rat mite (Ornithonyssus bacoti) and northern fowl mite (Ornithonyssus sylviarum).

Cheyletidae mites such as Cheyletiella yasguri and Cheyletiella blakei.

Demodicidae mites such as Demodex canis and Demodex cati.

Psoroptidae mites such as Psoroptes ovis.

Sarcoptidae mites such as Sarcoptes scabiei, Notoedres cati and Knemidocoptes spp.

Crustaceans such as Armadillidium vulgare.

Gastropods such as Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Limax Valentiana, Acusta despecta sieboldiana and Euhadra peliomphala.

Nematodes such as Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi and Bursaphelenchus xylophilus.

Adult flies such as horn fly (Haematobia irritans), horse fly (Tabanus spp.), Stomoxys calcitrans, blackfly (Simulium spp.), deer fly (Chrysops spp.), louse fly (Melophagus ovinus) and tsetse fly (Glossina spp.).

Parasitic worms such as sheep bot fly (Oestrus ovis, Cuterebra spp.), blowfly (Phaenicia spp.), screwworm (Cochliomyia hominivorax), warble fly (Hypoderma spp.), fleeceworm and Gastrophilus.

Mosquitos such as Culex spp., Anopheles spp. and Aedes spp.

The internal, livestock, poultry or pet parasites that the compounds of the present invention can control specifically include the following internal pests, but the present invention is not restricted thereto.

Nematodes of the genera Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, and the like.

Nematodes of the family Filariidae such as the genera Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa, and the like.

Nematodes of the family Dracunculidae such as the genus Dracunculus.

Cestodes such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus and Echinococcus multilocularis.

Trematodes such as Fasciola hepatica, F.gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E.coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium and Schistosoma mansoni.

Eimeria spp. such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis and Eimeria ovinoidalis.

Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica and Theileria spp.

The compounds of the present invention are effective against pests that have acquired resistance to conventional insecticides such as organic phosphorus compounds, carbamate compounds or pyrethroid compounds.

That is, the compounds of the present invention can effectively control pests such as insects of the order Collembola, the order Dictyoptera, the order Orthoptera, the order Isoptera, the order Thysanoptera, the order Hemiptera, the order Lepidoptera, the order Coleoptera, the order Hymenoptera, the order Diptera, the order Aphaniptera, the order Anoplura, Acari, gastropods and nematodes at low doses. On the other hand, the compounds of the present invention have a quite advantageous feature that they are almost harmless to mammals, fishes, crustaceans and beneficial insects (useful insects such as honey bees and bumblebees and natural enemies such as aphelinids, Aphidiinae, tachina flies, Orius spp., Phytoseiidae spp. etc.).

The compounds of the present invention may be used in any dosage form such as a soluble concentrate, an emulsifiable concentrate, a wettable powder, a water soluble powder, a water dispersible granule, a water soluble granule, a suspension concentrate, a concentrated emulsion, a suspoemulsion, a microemulsion, a dustable powder, a granule, a tablet or an emulsifiable gel usually after mixed with an appropriate solid carrier or liquid carrier, and if necessary, with a surfactant, a penetrant, a spreader, a thickener, an anti-freezing agent, a binder, an anti-caking agent, a disintegrant, an antifoaming agent, a preservative, a stabilizer or the like. A formulation in an arbitrary dosage form may be sealed in water-soluble packaging such as a water-soluble capsule or a water-soluble film, for labor saving or improved safety.

As solid carriers, natural minerals such as quartz, calcite, meerschaum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite, methahalloysite, kibushi clay, gairome clay, pottery stone, zeeklite, allophane, Shirasu, mica, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth; calcined natural minerals such as calcined clay, pearlite, Shirasu-balloons, vermiculite, attapulgus clay and calcined diatomaceous earth; inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, saccharides such as glucose, fructose, sucrose and lactose; polysaccharides such as starch, cellulose powder and dextrin; organic substances such as urea, urea derivatives, benzoic acid and benzoic acid salts; plants such as wood flour, powdered cork, corncob, walnut shell and tobacco stems, fly ash, white carbon (such as hydrated synthetic silica, anhydrous synthetic silica and hydrous synthetic silicate), fertilizers and the like may be mentioned.

As liquid carriers, aromatic hydrocarbons such as xylene, alkyl (C or C etc.) 9 10 benzene, phenylxylylethane and alkyl (C1 or C3 etc.) naphthalene; aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin and naphthene; mixtures of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol; polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol; ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone and γ-butyrolactone; esters such as fatty acid methyl esters, dialkyl succinates, dialkyl glutamate, dialkyl adipates and dialkyl phthalates; acid amides such as N- alkyl (C1, C8 or C12 etc.) pyrrolidone; fats and oils such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil; dimethyl sulfoxide; water and the like may be mentioned.

These solid and liquid carriers may be used alone or in combinations of two or more.

As surfactants, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene(mono, di or tri)styrylphenyl ether, polyoxyethylenepolyoxypropylene block copolymers, polyoxyethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, ethylene oxide adducts of castor oil, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol and alkyl glycosides; anionic surfactants such as alkyl sulfate salts, alkylbenzenesulfonic acid salts, lignin sulfonate, alkylsulfosuccinic acid salts, naphthalenesulfonic acid salts, alkylnaphthalenesulfonic acid salts, salts of naphthalenesulfonic acid-formalin condensates, salts of alkylnaphthalenesulfonic acid- formalin condensates, polyoxyethylene alkyl ether sulfate or phosphate salts, polyoxyethylene (mono or di) alkylphenyl ether sulfate or phosphate salts, polyoxyethylene (mono, di or tri) styrylphenyl ether sulfate or phosphate salts, polycarboxylic acid salts (such as polyacrylates, polymaleates and copolymers of maleic acid and an olefin) and polystyrenesulfonic acid salts; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid types and betaine types, silicone surfactants; and fluorine surfactants may be mentioned.

The amount of these surfactants is usually preferably from 0.05 to 20 parts by weight per 100 parts by weight of the agent of the present invention, though there is no particular restrictions. These surfactants may be used alone or in combination of two or more.

The suitable application dose of the compounds of the present invention is generally about from 0.005 to 50 kg per hectare (ha) in terms of the active ingredient, though it varies depending on the application situation, the application season, the application method and the cultivated crop.

When the compounds of the present invention are used to control external or internal parasites in or on mammals and birds as farm animals/poultry and pet animals, the compounds of the present invention may be administered in an effective amount together with pharmaceutically acceptable additives orally, parenterally by injection (intramuscular, subcutaneously, intravenously or intraperitoneally); percutaneously by dipping, spraying, bathing, washing, pouring-on and spotting-on and dusting, or intranasally. The compounds of the present invention may be administered through molded articles such as chips, plates, bands, collars, ear marks, limb bands and ID tags.

The compounds of the present invention are administered in an arbitrary dosage form suitable for the administration route.

In a case where the compounds of the present invention are used to control external or internal parasites, the suitable application dose of the compound of the present invention as an active ingredient is generally from 0.01 to 100 mg/kg body weight, preferably from 0.01 to 50 mg/kg body weight of a target animal, though it varies depending on e.g. the type of pests to be controlled, the type of the target animal, or the application method. Particularly with respect to application to a dog, the suitable application dose is generally from 1 to 5,000 mg/kg body weight, preferably from 1 to 100 mg/g body weight of a target dog, though it varies depending on the type or the age of the target dog, or the external parasites to be controlled.

In a case where the compounds of the present invention are used to control external or internal parasites, the application interval may be optionally set usually within a range of from daily to annually, though it varies dependeing on e.g. the type of pests to be controlled, the type of the target animal, or the application method. The application interval is preferably from once a week to every six months, more preferably daily (every 24 hours), monthly, once a month, every two months, or every three months.

In a case where the compounds of the present invention are used to control external paracites on a dog, with respect to the timing of application of the compound of the present invention to the dog, the compound of the present invention may be orally administered to the dog 30 minutes before start of feeding or 120 minutes after completion of feeding. "30 minutes before start of feeding or 120 minutes after completion of feeding" here is based on an action of the dog to take nutritious food.

For example, in a case where the dog feeding time is 20 minutes, the time specified is 30 minutes before start of feeding to 120 minutes after completion of feeding, that is, 170 minutes in total. A case where feeding is suspended, the compound of the present invention is orally administered and feeding is restarted, is included. In this specification, feeding means an action of an animal to take food.

The number of feeding of a dug is usually three to four times a day in the case of a dog of less than six months old, twice to three times a day in the case of a dog of six months to less than one year old, twice a day in the case of an adult dog of about one to five years old, and twice to three times a day in the case of an old dog of 6 years old or older, though it varies depending on the type or the age of the dog or the habit. In the present invention, feeding means an action of an animal to take nutritious food, and does not include an action to give food and the like to a dog for training or breeding.

The dosage form may be a solid preparation such as dusts, granules, wettable powders, pellets, tablets, boluses, capsules and a molded article containing an active ingredient; a liquid preparation such as an injection fluid, an oral liquid, a liquid preparation applied to the skin or coelom; a solution preparation such as a pour-on preparation, a spot-on preparation, flowables and emulsions; and a semisolid preparation such as an ointment and gels.

In a case where the compounds of the present invention are orally administered, the dosage form may, for example, be a solid preparation such as tablets, chewables, capsules, pills, boluses, granules and powders; a semisolid preparation such as pastes and gels; and a liquid preparation such as drinks.

In the case of percutaneous administeration, the dosage form may, for example, be a solid preparation such as powders; a semisolid preparation such as a cream, a salve and ointment, pastes and gels; and a liquid preparation such as a spary, aerosols, solutions and emulsions, suspensions, and lotions.

Further, in the case of administration by injection, the dosage form may, for example, be a liquid preparation such as solutions and emulsions, and suspensions, and in the case of intranasal administration, the dosage form may, for example, be a liquid preparation such as aerosols. In the case of spraying over an environment where animals are bred, such as a stable, the dosage form may, for example, be a solid preparation such as wettale powders, dusts or granules; and a liquid preparation such as emulsions and suspension concentrates.

The formulation to be used for parasiticides of the present invention is not limited to such dosage forms.

The solid preparation may be orally administered as it is, or may be percutaneously administered or sprayed over an environment where animals are bred, such as a stable, after dilution with water.

The solid preparation to be orally administered, may be prepared by mixing the compound represented by the formula (1) or its salt and one or more vehicles or binders suitable for oral administration, and as the case requires, physiologically acceptable additives such as a lubricant, a disintegrant, a dye and a pigment, and forming the mixture into a desired shape.

The vehicle and the binder may, for example, be a saccharide or saccharide derivative such as lactose, sucrose, mannitol or sorbitol; a starch such as corn starch, wheat startch, rice starch or potato starch; a cellulse or cellulose derivative such as methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose or hydroxypropylmethyl cellulose; a protein or protein derivative such as zein or gelatin; honey, gum arabic glue, or a synthetic polymer compound such as polyvinyl alcohol or polyvinyl pyrolidone.

The lubricant may, for example, be magnesium stearate, and the disintegrant may, for example, be cellulose, agar, alginic acid, crosslinked polyvinyl pyrrolidone or a carbonate.

Among solid preparations to be orally administered, in the case of a solid formulation such as chewables, additives which impart a taste, texture or flavor desired by amimals to which the preparation is to be administered, may be used. The carriers and addtives to be used for the solid preparation of the parasiticidal composition of the present invention are not limited thereto.

The liquid preparation may be administered percutaneously or by injection as it is, or may be administered orally by being mixed with food, percutaneously administered after being diluted with water, or sprayed to an enviorment where animals are bred, such as a stable.

An injection fluid may be administered intravenously, intramuscularly or subcutaneously. An injection fluid can be prepared by dissolving an active ingredient in an appropriate solvent and, if necessary, adding additives such as a solubilizer, an acid, a base, a buffering salt, an antioxidant and a protectant.

As appropriate solvents, water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, and synthetic oils suitable for injection may be mentioned.

As solubilizers, polyvinylpyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester and the like may be mentioned.

As protectants, benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, n- butanol and the like may be mentioned.

An oral liquid may be administered directly or after dilution and can be prepared in the same manner as an injection fluid.

A flowable, an emulsion or the like may be administered directly or after dilution percutaneously or by environmental application.

A liquid preparation applied to the skin is administered by dripping, spreading, rubbing, spraying, sprinkling or dipping (soaking, bathing or washing) and can be prepared in the same manner as an injection fluid.

A pour-on preparation and a spot-on preparation are dripped or sprayed to a limited area of the skin so that they permeate through the skin and act systemically. A pour-on preparation and a spot-on preparation can be prepared by dissolving, suspending or emulsifying an active ingredient in an appropriate skin-friendly solvent or solvent mixture. If necessary, additives such as a surfactant, a colorant, an absorbefacient, an antioxidant, a light stabilizer and an adhesive may be added.

As appropriate solvents, water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF (N,N-dimethylformamide), liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyloxy- methylene-1,3-dioxolane may be mentioned.

As absorbefacients, DMSO (dimethyl sulfoxide), isopropyl myristate, pelargonic acid dipropylene glycol, silicone oil, fatty acid esters, triglycerides and aliphatic alcohols may be mentioned.

As antioxidants, sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol may be mentioned.

An emulsion may be administered orally, percutaneously or by injection. An emulsion can be prepared by dissolving an active ingredient in a hydrophobic phase or a hydrophilic phase and homogenizing the resulting solution with another liquid phase together with an appropriate emulsifier, and further if necessary with additives such as a colorant, an absorbefacient, a protectant, an antioxidant, a light screen and a thickner.

As hydrophobic phases (oils), paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglycerides, ethyl stearate, di-n-butyryl adipate, hexyl laurate, pelargonic acid dipropylene glycol, esters of branched short-chain fatty acids with C - C saturated fatty acids, isopropyl myristate, isopropyl palmitate, esters of C -C 18 12 18 saturated alcohols with caprylic/capric acid, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, fatty acid ester waxes, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol and oleyl alcohol may be mentioned.

As hydrophilic phases, water, propylene glycol, glycerin and sorbitol may be mentioned.

As emulsifiers, nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinic acid, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate and alkyl phenol polyglycol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium lauryl sulfate, aliphatic alcohol sulfate ether and mono/dialkylpolyglycol orthophosphate monoethanolamine salt; and cationic surfactants such as cetyltrimethylammonium chloride may, for example, be mentioned.

As other additives, carboxymethylcellulose, methylcellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, maleic anhydride copolymers, polyethylene glycol, waxes and colloidal silica may be mentioned.

A semisolid preparation is administered by applying or spreading onto the skin or introducing into the coelom. A gel can be prepared by adding a thickener to a solution prepared in the same manner as an injection fluid sufficiently to give a transparent viscous substance like an ointment.

Next, Formulation Examples of preparations using the compounds of the present disclosure are given below. However, formulations of the present invention are by no means restricted thereto. In the following Formulation Examples, "parts" means parts by weight.

[Wettable powder] Compound of the present disclosure 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts As the others, an anti-caking agent, a stabilizer and the like may be mentioned.

[Emulsifiable concentrate] Compound of the present disclosure 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts As the others, a spreader, a stabilizer and the like may be mentioned.

[Suspension concentrate] Compound of the present disclosure 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts As the others, an anti-freezing agent, a thickener and the like may be mentioned.

[Water dispersible granule] Compound of the present disclosure 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts As the others, a binder, a stabilizer and the like may be mentioned.

[Soluble concentrate] Compound of the present disclosure 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts As the others, an anti-freezing agent, a spreader and the like may be mentioned.

[Granule] Compound of the present disclosure 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts As the others, a binder, a stabilizer and the like may be mentioned.

[Dustable powder] Compound of the present disclosure 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts As the others, an anti-drift agent, a stabilizer and the like may be mentioned.

Next, more specific Formulation Examples of preparations containing the compounds of the present disclosure as an active ingredient are given below.

However, the present invention is by no means restricted thereto.

In the following Formulation Examples, "parts" means parts by weight.

[Formulation Example 1] Wettable powder Compound No.1001a of the present disclosure 20 parts Pyrophyllite 74 parts Sorpol 5039 4 parts (tradename for a mixture of a nonionic surfactant and an anionic surfactant: manufactured by TOHO Chemical Industry Co., Ltd.) CARPLEX #80D 2 parts (tradename for hydrous synthetic silicic acid: manufactured by Shionogi & Co., Ltd.) The above ingredients are mixed and pulverized homogenously to obtain a wettable powder.

[Formulation Example 2] Emulsifiable concentrate Compound No.1001a of the present disclosure 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Sorpol 2680 5 parts (tradename for a mixture of a nonionic surfactant and an anionic surfactant: manufactured by TOHO Chemical Industry Co., Ltd.) The above ingredients are mixed homogenously to obtain an emulsifiable concentrate.

[Formulation Example 3] Suspension concentrate Compound No.1001a 25 parts AGRISOL S-710 10 parts (tradename for a nonionic surfactant: manufactured by Kao Corporation) Runox 1000C 0.5 part (tradename for an anionic surfactant: manufactured by TOHO Chemical Industry Co., Ltd.) Xanthan gum 0.2 part Water 64.3 parts The above ingredients are mixed homogenously and wet-pulverized to obtain a suspension concentration.

[Formulation Example 4] Water dispersible granule Compound No. 1001a of the present disclosure 75 parts HITENOL NE-15 5 parts (tradename for an anionic surfactant: manufactured by DKS Co., Ltd.) VANILLEX N 10 parts (tradename for an anionic surfactant: manufactured by Nippon Paper Industries Co., Ltd.) CARPLEX #80D 10 parts (tradename for hydrous synthetic silicic acid: manufactured by Shionogi & Co., Ltd.) The above ingredients are mixed and pulverized homogenously, then kneaded with a small amount of water, granulated through an extrusion granulator and dried to obtain a water dispersible granule.

[Formulation Example 5] Granule Compound No. 1001a of the present disclosure 5 parts Bentonite 50 parts Talc 45 parts The above ingredients are mixed and pulverized homogenously, then kneaded with a small amount of water, granulated through an extrusion granulator and dried to obtain a granule.

[Formulation Example 6] Dustable powder Compound No. 1001a of the present disclosure 3 parts CARPLEX #80D 0.5 part (tradename for a hydrous synthetic silicic acid: manufactured by Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are mixed and pulverized homogeneously to obtain a dustable powder.

It is applied after diluted with water by a factor of from 1 to 10000 or directly without dilution.

[Formulation Example 7] Wettable powder preparation Compound No. 1001a of the present disclosure 25 parts Sodium diisobutylnaphthalenesulfonate 1 part Calcium n-dodecylbenzenesulfonate 10 parts Alkyl aryl polyglycol ether 12 parts Naphthalenesulfonic acid-formalin condensate sodium salt 3 parts Silicone emulsion 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation Example 8] Water-soluble concentrate preparation Compound No. 1001a of the present disclosure 20 parts Polyoxyethylenelauryl ether 3 parts Sodium dioctylsulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-Propanol 36.5 parts [Formulation Example 9] Liquid preparation for spraying Compound No. 1001a of the present disclosure 2 parts Dimethyl sulfoxide 10 parts 2-Propanol 35 parts Acetone 53 parts [Formulation Example 10] Liquid preparation for percutaneous administration Compound No. 1001a of the present disclosure 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation Example 11] Liquid preparation for percutaneous administration Compound No. 1001a of the present disclosure 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation Example 12] Liquid preparation for percutaneous administration (by dripping) Compound No. 1001a of the present disclosure 2 parts Light liquid paraffin 98 parts [Formulation Example 13] Liquid preparation for percutaneous administration (by dripping) Compound No. 1001a of the present disclosure 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-etsu silicone 1 part For use as agricultural chemicals, the compounds of the present invention may be mixed with other herbicides, insecticides, acaricides, nematocides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners and the like at the time of formulation or application.

Particularly, the combined use with other agricultural chemicals or plant hormone is expected to reduce the cost by enabling control at lower doses, to broaden the insecticidal spectrum by the synergistic effect of the other agrochemicals, and to achieve a higher pesticidal effect. In such cases, they may be combined with a plurality of known agricultural chemicals.

The agricultural chemicals to be used in combination with the compounds of the present invention include, for example, the compounds disclosed in e.g. The Pesticide Manual, 15th edition, 2009, having the generic names listed below, but are not necessarily restricted thereto.

Fungicides: acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, ametoctradin, amisulbrom, amobam, ampropyfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, bethoxazine, binapacryl, biphenyl, bitertanol, blasticidin-S, bixafen, bordeaux mixture, boscalid, bromuconazole, bupirimate, buthiobate, calcium polysulfide, calcium polysulfide, captafol, captan, carpropamid, carbamorph, carbendazim, carboxin, carvone, cheshunt mixture, chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazol, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, clotrimazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate, cufraneb, coumoxystrobin, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazol, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, dichlofluanid, dichlone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomedine, dicloran, etc.

Fungicides (continued): diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbon, diphenylamine, dipymetitrone, dipyrithione, ditalimfos, dithianon, dodemorph-acetate, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, etaconazole, ethaboxam, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenarimol, fenbuconazole, fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fendazosulam, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpyrazamine, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, flufenoxystrobin, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fosetyl- aluminium, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, furconazole-cis, furmecyclox, furphanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb, isofetamid, isoprothiolane, isopyrazam, isotianil, isovaledione, etc.

Fungicides (continued): kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mepanipyrim, meptyldinocap, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, methyl isothiocyanate, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, natamycin, nickel bis(dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, OCH, octhilinone, ofurace, orysastrobin, oxathiapiprolin, oxadixyl, oxine copper, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, penflufen, pencycuron, penthiopyrad, o-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, proquinazid, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyraziflumid, pyrazophos, pyribencarb- methyl, pyridinitril, pyrifenox, pyrimethanil, pyriminostrobin, pyrimorph, pyriofenone, pyrisoxazole, pyroquilon, pyroxychlor, pyroxyfur, quinomethionate, quinoxyfen, quintozene, quinacetol-sulfate, quinazamid, quinconazole, rabenzazole, Bacillus subtilis (Strain:D747, FZB24, GBO3, HAI0404, MBI600, QST713, Y1336, etc.), etc.

Fungicides (continued): sedaxane, sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salycylanilide, silthiofam, simeconazole, tebuconazole, tebufloquin, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, tiadinil, tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, toriadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triclopyricarb, triticonazole, validamycin, valifenalate, vinclozolin, zarilamide, zinc sulfate, zineb, ziram, zoxamide, shiitake mushroom mycelium extracts, shiitake mushroom fruiting body extracts, ZF- 9646 (test name), NF-180 (test name), MIF-1002 (test name), S-2399 (test name), AKD- 5195 (test name), NNF-0721 (test name), etc.

Bactericides: benzalkonium chloride, bithionol, bronopol, cresol, formaldehyde, nitrapyrin, oxolinic acid, oxyterracycline, streptomycin, tecloftalam, etc.

Nematicides: aldoxycarb, benclothiaz, cadusafos, DBCP, dichlofenthion, DSP, ethoprophos, fenamiphos, fensulfothion, fluazaindolizine, fluensulfone, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos, oxamyl, thiaxazafen, thionazin, tioxazafen, BYI-1921 (test name), MAI-08015 (test name), etc.

Acaricides: acequinocyl, acrinathrin, amidoflumet, amitraz, azocyclotin, BCI-033 (test name), benzoximate, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyenopyrafen, cyflumetofen, cyhexatine, dicofol, dienochlor, diflovidazin, DNOC, etoxazole, fenazaquin, fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, halfenprox, hexythiazox, milbemectin, propargite, pyflubumide, pyridaben, pyrimidifen, S-1870 (test name), spirodiclofen, spyromesifen, CL900167 (test name), tebufenpyrad, NA-89 (test name), etc.

Insecticides: abamectin, acephate, acetamipirid, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, azamethiphos, azinphos-ethyl, azinphos-methyl, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, broflanilide, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorantraniliprole, chlorethxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, cyphenothrin, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dicloromezotiaz, dichlorvos, diflubenzuron, dimefluthrin, dimethylvinphos, dinotefuran, diofenolan, disulfoton, dimethoate, emamectin-benzoate, empenthrin, endosulfan, alpha-endosulfan, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenthion, fenvalerate, fipronil, flonicamid, fluazuron, flubendiamide, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flumethrin, fluralaner, fluvalinate, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, flufiprole, fluhexafon, flupyradifurone, flometoquin, etc.

Insecticides (continued): gamma-cyhalothrin, halofenozide, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, imiprothrin, isofenphos, indoxacarb, indoxacarb-MP, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, epsilon-metofluthrin, metofluthrin, momfluorothrin, epsilon-momfluorothrin, monocrotophos, muscalure, nitenpyram, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol (PCP), permethrin, phenothrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, profluthrin, prothiofos, propaphos, protrifenbute, pymetrozine, pyraclofos, pyrethrins, pyridalyl, pyrifluquinazon, pyriprole, pyrafluprole, pyriproxyfen, resmethrin, rotenone, SI-0405 (test name), sulprofos, silafluofen, spinetoram, spinosad, spiromesifen, spirotetramat, sulfoxaflor, sulfotep, SYJ-159 (test name), tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, tetramethrin, d-tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, trichlorfon, triazuron, triflumezopyrim, triflumuron, vamidothion, fluxametamide, MIE-1209 (test name), ME5382 (test name), etc.

EXAMPLES Now, the present invention will be described in further detail with reference to Examples of synthesis of and tests on the compounds of the present invention.

However, the present invention is by no means restricted thereto.

For the preparative medium pressure liquid chromatography described in Synthetic Examples and Reference Examples, a preparative medium pressure chromatograph YFLC-Wprep manufactured by Yamazen Science, Inc. (flow rate: 18 ml/min, 40-µm silica gel column) was used.

Chemical shift values of proton nuclear magnetic resonance (NMR) in Synthetic Examples and Reference Examples were measured by using Me4Si (tetramethylsilane) as a standard substance at 300 MHz (ECX300 or ECP300 manufactured by JEOL Ltd.).

Reference symbols in proton nuclear magnetic resonance chemical shift values have the following meanings. s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, and m: multiplet.

Solvents used for NMR measurement are represented in brackets in the chemical shift value data.

Synthetic Example 1: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)imidazo[1,2-c]pyrimidine (compound No. 1001a of the present disclosure) 82 mg of 6-(trifluoromethyl)pyrimidinamine was dissolved in 5 ml of chlorobenzene, and 200 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

After the addition, the reaction mixture was stirred under reflux with heating for 9 hours.

After the reaction, the reaction mixture was mixed with 10 ml of a 1M sodium hydroxide aqueous solution and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate [with a gradient of from 100:0 to 0:100 (volume ratio, the same applies hereinafter)] as the eluent to obtain 163.5 mg of the desired product as a flesh-colored solid.

Melting point: 235-237 C H-NMR(CDCl ) : δ9.38(d, J=7.5Hz, 1H), 9.19(s, 1H), 8.63(s, 1H), 8.12-8.09(m, 1H), 8.02-8.00(m, 1H), 7.28-7.23(m, 1H), 3.73(q, J=7.4Hz, 2H), 1.34(t, J=7.4Hz, 3H).

Synthetic Example 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1- 1-002b of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1- 1-002a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridin yl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 856 mg of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 20 ml of pyridine, and 1.00 g of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid, 1.32 g of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 42 mg of 4-(dimethylamino)pyridine were added at room temperature. After the addition, the reaction mixture was stirred for 6 hours at room temperature. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was washed with a 1M hydrochloric acid aqueous solution, and dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.40 g of the desired crude product. The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1002b of the present disclosure) 1.40 g of the crude 3-(ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridinyl]- 7-(trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 15 ml of acetic acid, and the solution was stirred under reflux with heating for 2 hours. After the stirring, the reaction mixture was stirred at room temperature overnight. After the stirring, the solid precipitated in the reaction mixture was collected by filtration. The obtained solid was washed with diisopropyl ether to obtain 645 mg of the desired product as a white solid.

Melting point: 199-202 C H-NMR(CDCl ) : δ8.78(d, J=7.2Hz, 1H), 8.73(d, J=1.5Hz, 1H), 8.40(d, J=2.0Hz, 1H), 8.06-8.04(m, 1H), 7.21(dd, J=7.2, 1.5Hz, 1H), 4.33(s, 3H), 3.15(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1002a of the present disclosure) To a solution of 645 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 15 ml of chloroform, 961 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2.5 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatograph using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 660 mg of the desired product as a white solid.

Melting point: 203-205 C H-NMR(CDCl ) : δ9.42(d, J=7.5Hz, 1H), 8.77(s, 1H), 8.36(d, J=1.7Hz, 1H), 8.16(s, 1H), 7.32(dd, J=7.5, 1.7Hz, 1H), 4.18(s, 3H), 4.11(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).

Synthetic Example 3: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl][(trifluoromethyl)thio]benz[d]oxazole (compound No. 1003b of the present disclosure), 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridinyl] [(trifluoromethyl)sulfinyl]benz[d]oxazole (compound No. 1002a of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridinyl] [(trifluoromethyl)sulfonyl]benz[d]oxazole (compound No. 1001a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-{2-hydroxy[(trifluoromethyl)thio]phenyl} (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 466 mg of 2-amino[(trifluoromethyl)thio]phenol was dissolved in 10 ml of pyridine, and 356 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid, 471 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 75 mg of 4-(dimethylamino)pyridine were added. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the solvent was evapoarated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 100 mg of the desired product as a reddish brown solid.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] [(trifluoromethyl)thio]benz[d]oxazole (compound No. 1003b of the present disclosure) A solution of 89 mg of 3-(ethylthio)-N-{2-hydroxy[(trifluoromethyl)thio]phenyl} (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide in 5 ml of tetrahydrofuran was warmed to 50 C, and 65 mg of bis(2-methoxyethyl) azodicarboxylate and 73 mg of triphenylphosphine were added.

After the addition, the reaction mixture was stirred at 50 C for 3 hours. After the stirring, the reaction mixture was stirred at room temperature overnight. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 85:15 to 0:100) as the eluent to obtain 21 mg of the desired product as a pale brown solid.

H-NMR(CDCl3) : δ8.96(s, 1H), 8.23(s, 1H), 8.00-7.45(m, 4H), 3.11(q, J=7.4Hz, 2H), 1.26(t, J=7.4Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl][(trifluoromethyl)sulfinyl]benz[d]oxazole (compound No. 1002a of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridinyl] [(trifluoromethyl)sulfonyl]benz[d]oxazole (compound No. 1001a of the present disclosure) To a solution of 21 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl][(trifluoromethyl)thio]benz[d]oxazole in 5 ml of chloroform, 67 mg of 65 weight% m- chloroperbenzoic acid (containing about 30 weight% of water) was added. After the addition, the reaction mixture was stirred at room temperature overnight. After the stirring, the reaction mixture was stirred under reflux with heating for another 2 hours.

After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml). The resulting organic layer was washed with a satrated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 5 mg of the desired 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl][(trifluoromethyl)sulfinyl]benz[d]oxazole as a desired product and 13 mg of the desired 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl][(trifluoromethyl)sulfonyl]benz[d]oxazole respectively as a pale brown solid.

H-NMR (CDCl3) of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl][(trifluoromethyl)sulfinyl]benz[d]oxazole: δ9.75(s, 1H), 8.37(s, 1H), 8.05-7.35(m, 4H), 4.09(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).

H-NMR (CDCl3) of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl][(trifluoromethyl)sulfonyl]benz[d]oxazole: δ9.74(s, 1H), 8.62(s, 1H), 8.25-7.40(m, 4H), 4.07(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H).

Synthetic Example 4: Synthesis of 5-(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl][(trifluoromethyl)imidazo[2,1-b]thiazole (compound No. 2 001b of the present disclosure) and 5-(ethylsulfonyl)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1-b]thiazole (compound No. 2 001a of the present disclosure) Step 1: Synthesis of 5-(ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridin yl](trifluoromethyl)imidazo[2,1-b]thiazolecarboxamide 242 mg of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 250 mg of 5-(ethylthio)(trifluoromethyl)imidazo[2,1-b]thiazole carboxylic acid, 322 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 10 mg of 4-(dimethylamino)pyridine were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnignt. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was washed with a 1M hydrochloric acid aqueous solution, and dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain crude 5- (ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[2,1-b]thiazolecarboxamide as the desired product. The crude product was used in the next step without further purification.

Step 2: Synthesis of 5-(ethylhio)[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl](trifluoromethyl)imidazo[2,1-b]thiazole (compound No. 2001b of the present disclosure) The crude 5-(ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[2,1-b]thiazolecarboxamide obtained in Step 1 was dissolved in 10 ml of acetic acid, and the solution was stirred under reflux with heating for 4.5 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of a 1M hydrochloric acid aqueous solution and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration. The obtained solid was washed with diisopropyl ether to obtain 332 mg of the desired product as a white solid.

Melting point: 200-203 C H-NMR(CDCl3) : δ8.72-8.67(m, 1H), 8.37-8.33(m, 1H), 8.12-8.08(m, 1H), 4.25(s, 3H), 3.14(q, J=7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H).

Step 3: Synthesis of 5-(ethylsulfonyl)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1-b]thiazole (compound No. 2 001a of the present disclosure) To a solution of 132 mg of 5-(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1-b]thiazole in 3 ml of chloroform, 155 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 110 mg of the desired product as a white solid.

Melting point: 249-251 C H-NMR(CDCl3) : δ8.76-8.71(m, 1H), 8.71-8.66(m, 1H), 8.36-8.32(m, 1H), 4.23(s, 3H), 4.19(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).

Synthetic Example 5: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)imidazo[1,2-b]pyridazine (compound No. 1001a of the present disclosure) 82 mg of 5-(trifluoromethyl)pyridazinamine was dissolved in 5 ml of chlorobenzene, and 200 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

After the addition, the reaction mixture was stirred under reflux with heating for 3 hours.

After the reaction, the reaction mixture was mixed with 10 ml of a 1M sodium hydroxide aqueous solution and extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 142 mg of the desired product as a brown solid.

Melting point: 214-218 C H-NMR(CDCl3) : δ9.40(d, J=7.5Hz, 1H), 8.94(s, 1H), 8.58(d, J=2.0Hz, 1H), 8.34- 8.30(m, 1H), 8.11-8.09(m, 1H), 7.24(dd, J=7.5, 2.0Hz, 1H), 3.79(q, J=7.4Hz, 2H), 1.36(t, J=7.4Hz, 3H).

Synthetic Example 6: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyrazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1- 1-029b of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyrazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1- 1-029a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridin yl](trifluoromethyl)imidazo[1,2-a]pyrazinecarboxamide 271 mg of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 270 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyrazine carboxylic acid and 357 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydroxhloride were added. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduce pressure to obtain crude 3-(ethylthio)-N-[2-(methylamino) (trifluoromethyl)pyridinyl](trifluoromethyl)imidazo[1,2-a]pyrazinecarboxamide.

The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyrazinyl]- 3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1029b of the present disclosure) The crude 3-(ethylthio)-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyrazinecarboxamide obtained in Step 1 was dissolved in 10 ml of acetic acid, and the solution was stirred under reflux with heating for 17 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chlromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 80:20) as the eluent to obtain 257 mg of the desired product as a white solid.

Melting point: 220-222 C H-NMR(CDCl3) : δ9.24(s, 1H), 8.99(s, 1H), 8.76(d, J=1.5Hz, 1H), 8.42(d, J=1.5Hz, 1H), 4.37(s, 3H), 3.26(q, J=7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyrazin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1029a of the present disclosure) To a solution of 232 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyrazin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 5 ml of chloroform, 326 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml).

The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was mixed with 10 ml of diisopropyl ether, followed by filtration to obtain 203 mg of the desired product as a white solid.

Melting point: 234-236 C H-NMR(CDCl ) : δ9.63(s, 1H), 9.39(s, 1H), 8.81-8.77(m, 1H), 8.39-8.36(m, 1H), 4.25(s, 3H), 4.23(q, J=7.5Hz, 2H), 1.49(t, J=7.5Hz, 3H).

Synthetic Example 7: Synthesis of 2-[6-bromo(ethylthio) (trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridine (compound No. 1023b of the present disclosure) and 2-[6-bromo (ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl(trifluoromethyl)- 3H-imidazo[4,5-b]pyridine (compound No. 1023a of the present disclosure) Step 1: Synthesis of 6-bromo-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 1.51 g of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 20 ml of pyridine, and 2.04 g of 6-bromo(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid and 2.53 g of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride were added. After the addition, the reaction mixture was stirred at room temperature for 3 hours. After the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 2.98 g of desired product as a flesh-colored solid.

Melting point: 200-205 C H-NMR(CDCl ) : δ8.77(brs, 1H), 8.54(s, 1H), 8.40-8.36(m, 1H), 8.28(s, 1H), 8.04(s, 1H), 7.85(d, J=2.0Hz, 1H), 5.20(brs, 1H), 3.10(d, J=4.8Hz, 3H).

Step 2: Synthesis of 2-[6-bromo(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine 2.93 g of 6-bromo-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide was dissolved in 15 ml of acetic acid, and the solution was stirred under reflux with heating for 2 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodim sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 2.82 g of the desired product as a pale brown solid.

Melting point: 220-225 C H-NMR(CDCl ) : δ8.71(d, J=1.4Hz, 1H), 8.55(s, 1H), 8.51(s, 1H), 8.27(d, J=1.4Hz, 1H), 8.14(s, 1H), 4.47(s, 3H).

Step 3: Synthesis of 2-[6-bromo(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1- 1-023b of the present disclosure) 518 mg of N-chlorosuccinimide was dissolved in 5 ml of 1,2-dichloroethane, and 321 mg of ethanethiol was added at -40 C. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the stirring, to the reaction mixture, a solution of 300 mg of 2-[6-bromo(trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 2 ml of 1,2-dichloroethane was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 3 hours. After the stirring, to the reaction mixture, a solution of 1.04 g of N- chlorosuccinimide and 642 mg of ethanethiol in 5 ml of 1,2-dichloroethane prepared in a separate container was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 3 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×2).

The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 212 mg of the desired product as a white solid.

Melting point: 214-215 C H-NMR(CDCl ) : δ8.93(s, 1H), 8.74(d, J=1.4Hz, 1H), 8.40(d, J=1.4Hz, 1H), 8.13(s, 1H), 4.33(s, 3H), 3.18(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).

Step 4: Synthesis of 2-[6-bromo(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1- 1-023a of the present disclosure) To a solution of 150 mg of 2-[6-bromo(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 5 ml of chloroform, 175 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 142 mg of the desired product as a white solid.

Melting point: 226-228 C H-NMR(CDCl ) : δ9.60(s, 1H), 8.77(d, J=1.4Hz, 1H), 8.36(d, J=1.4Hz, 1H), 8.23(s, 1H), 4.19(s, 3H), 4.15(q, J=7.5Hz, 2H), 1.49(t, J=7.5Hz, 3H).

Synthetic Example 8: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1031b of the present disclosure), 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-1H-imidazo[4,5-b]pyridine (compound No. 1001b of the present disclosure) and 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1030b of the present disclosure) Step 1: Synthesis of N-[2-amino(trifluoromethyl)pyridinyl]ethylthio (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 712 mg of 6-(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 972 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid and 1.32 g of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 1.20 g of the desired crude product as a reddish brown solid. The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] (trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1031b of the present disclosure) 1.2 g of the crude N-[2-amino(trifluoromethyl)pyridinyl]ethylthio (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 10 ml of propionic acid, and the solution was stirred under reflux with heating for 3 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.0 g of the desired product as a brown solid. The product was used in the next step without further purification.

H-NMR(CDCl ) : δ8.59(d, J=7.2Hz, 1H), 8.03(d, J=7.8Hz, 1H), 7.83(s, 1H), 7.36(d, J=7.8Hz, 1H), 7.04-6.98(m, 1H), 3.02(q, J=7.4Hz, 2H), 1.05(t, J=7.4Hz, 3H) (no peak of proton of NH was observed).

Step 3: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-1H-imidazo[4,5-b]pyridine (compound No. 1001b of the present disclosure) and 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1030b of the present disclosure) To a solution of 66 mg of 63 weight% sodium hydride (dispersed in mineral oil) in 3 ml of N,N-dimethylformamide, a solution of 500 mg of 2-[3-(ethylthio) (trifluoromethyl)imidazo[1,2-a]pyridinyl](trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 7 ml of N,N-dimethylformamide was added under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the stirring, to the reaction mixture, 286 mg of methyl trifluoromethanesulfonate was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n- hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 150 mg of the desired 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl- -(trifluoromethyl)-1H-imidazo[4,5-b]pyridine and 218 mg of the desired 2-[3-(ethylthio)- 7-(trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridine respectively as a brown solid and as a white solid.

Melting point of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-1H-imidazo[4,5-b]pyridine: 164-166 C H-NMR(CDCl3) : δ8.81(d, J=7.5Hz, 1H), 8.03(s, 1H), 7.91(d, J=8.2Hz, 1H), 7.70(d, J=8.2Hz, 1H), 7.20(dd, J=7.5, 1.7Hz, 1H), 4.31(s, 3H), 3.35(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).

Melting point of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine: 163-165 C H-NMR(CDCl ) : δ8.77(d, J=7.2Hz, 1H), 8.26(d, J=8.2Hz, 1H), 8.06(s, 1H), 7.68(d, J=8.2Hz, 1H), 7.21(dd, J=7.2, 1.5Hz, 1H), 4.33(s, 3H), 3.12(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).

Synthetic Example 9: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1- 8-005b of the present disclosure) and synthesis of 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5- c]pyridine (compound No. 1005a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[5-(methylamino)(trifluoromethyl)pyridin yl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 303 mg of N -methyl(trifluoromethyl)pyridine-3,4-diamine was dissolved in 15 ml of pyridine, and 552 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid and 732 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the solvent was evaporated under reduced pressure. The obtained residue was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 986 mg of the desired crude product. The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1005b of the present disclosure) 986 mg of the crude 3-(ethylthio)-N-[5-(methylamino)(trifluoromethyl)pyridin yl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 15 ml of acetic acid, and the solution was stirred under reflux with heating for 22 hours. After the stirring, the reaction mixture was stirred at room temperature overnight. After the reaction, the solvent was evaporated under reduced pressure.

The resulting residue was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 70:30) as the eluent to obtain 358 mg of the desired product as a yellow solid.

Melting point: 217-219 C H-NMR(CDCl3) : δ8.97(s, 1H), 8.78(d, J=7.2Hz, 1H), 8.20(s, 1H), 8.05(s, 1H), 7.22(d, J=7.2Hz, 1H), 4.37(s, 3H), 3.15(q, J=7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1005a of the present disclosure) To a solution of 258 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine in 8 ml of chloroform, 323 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for one hour. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml).

The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent. 10 ml of diisopropyl ether was added to the obtained solid, follwed by filtration to obtain 200 mg of the desired product as a yellow solid.

Melting point: 245-247 C H-NMR(CDCl ) : δ9.39(d, J=7.2Hz, 1H), 9.00(s, 1H), 8.14(s, 2H), 7.33(d, J=7.2Hz, 1H), 4.20(s, 3H), 4.07(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).

Synthetic Example 10: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]-3,4-dimethyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1003b of the present disclosure) and 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]-3,4-dimethyl(trifluoromethyl)-3H- imidazo[4,5-c]pyridine (compound No. 1003a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[2-methyl(methylamino) (trifluoromethyl)pyridinyl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 212 mg of N ,2-dimethyl(trifluoromethyl)pyridine-3,4-diamine was dissolved in ml of pyridine, and 200 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine- 2-carboxylic acid, 264 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 9 mg of 4-(dimethylamino)pyridine were added at room temperature.

After the addition, the reaction mixture was stirred at room temperature overnight.

After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain crude 3-(ethylthio)-N-[2-methyl (methylamino)(trifluoromethyl)pyridinyl](trifluoromethyl)imidazo[1,2-a]pyridine carboxamide. The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl]- 3,4-dimethyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1003b of the present disclosure) The crude 3-(ethylthio)-N-[2-methyl(methylamino)(trifluoromethyl)pyridin yl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 10 ml of acetic acid, and the solution was stirred under reflux with heating for 3 hours. After the reaction, the solvent was evaporated under reduced pressure.

The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 70:30) as the eluent to obtain 85 mg of the desired product as a white solid.

Melting point: 169-171 C H-NMR(CDCl3) : δ9.01(s, 1H), 8.03(s, 1H), 7.83(d, J=9.3Hz, 1H), 7.54(dd, J=9.3, 1.8Hz, 1H), 4.41(s, 3H), 3.10(q, J=7.5Hz, 2H), 3.08(s, 3H), 1.22(t, J=7.5Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl]-3,4-dimethyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1003a of the present disclosure) To a solution of 49 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl]-3,4-dimethyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine in 3 ml of chloroform, 57 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml).

The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 37 mg of the desired product as a white solid.

Melting point: 200-205 C H-NMR(CDCl ) : δ9.59(s, 1H), 7.97(s, 1H), 7.96(d, J=9.6Hz, 1H), 7.74(dd, J=9.6, 1.5Hz, 1H), 4.25(s, 3H), 3.96(q, J=7.5Hz, 2H), 3.08(s, 3H), 1.45(t, J=7.5Hz, 3H).

Synthetic Example 11: Synthesis of 3-(ethylsulfonyl)-6,7’-bis(trifluoromethyl)-2,2’- biimidazo[1,2-a]pyridine (compound No. 1002a of the present disclosure) 102 mg of 4-(trifluoromethyl)pyridinamine was dissolved in 4 ml of bromobenzene, and 300 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

After the addition, the reaction mixture was stirred under reflux with heating for 5 hours.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 168 mg of the desired product as a white solid.

Melting point: 245-248 C H-NMR(CDCl ) : δ9.65(s, 1H), 8.57(s, 1H), 8.30(d, J=7.2Hz, 1H), 8.01(s, 1H), 7.90(d, J=9.6Hz, 1H), 7.63(dd, J=9.6, 1.8Hz, 1H), 7.03(dd, J=7.2, 1.8Hz, 1H), 3.73(q, J=7.5Hz, 2H), 1.33(t, J=7.5Hz, 3H).

Synthetic Example 12: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](perfluoroethyl)imidazo[1,2-c]pyridine (compound No. 1008a of the present disclosure) and 3-bromo[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](perfluoroethyl)imidazo[1,2-c]pyrimidine (compound No. 1010a of the present disclosure) Step 1: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl](perfluoroethyl)imidazo[1,2-c]pyrimidine (compound No. 1008a of the present disclosure) 800 mg of 6-(perfluoroethyl)pyrimidinamine was dissolved in 10 ml of chlorobenzene, and 1,780 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 926 mg of the desired product as a pale solid.

Melting point: 233-239 C H-NMR(CDCl ) : δ9.63(s, 1H), 9.19(s, 1H), 8.64(s, 1H), 8.05(s, 1H), 7.92(d, J=9.6Hz, 1H), 7.66(dd, J=9.6, 1.5Hz, 1H), 3.72(q, J=7.5Hz, 2H), 1.35(t, J=7.5Hz, 3H).

Step 2: Synthesis of 3-bromo[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](perfluoroethyl)imidazo[1,2-c]pyrimidine (compound No. 1010a of the present disclosure) To a solution of 150 mg of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](perfluoroethyl)imidazo[1,2-c]pyrimidine in 2 ml of N,N- dimethylformamide, 57 mg of N-bromosuccinimide was added under cooling with ice.

After the addition, the reaction mixture was stirred at room temperature for 2 hours.

After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with diethyl ether (10 ml×2). The resulting organic layer was washed with a saturated sodium thiosulfate aqueous solution and then with saturated sodium hydrogen carbonate, dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 127 mg of the desired product as a white solid.

Melting point: 200-205 C H-NMR(CDCl3) : δ9.61(s, 1H), 9.20(s, 1H), 7.99(s, 1H), 7.96(d, J=9.6Hz, 1H), 7.68(d, J=9.6Hz, 1H), 4.00(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).

Synthetic Example 13: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(perfluoroethyl)imidazo[1,2-c]pyrimidine (compound No. 1 007a of the present disclosure) 143 mg of 2-methyl(perfluoroethyl)pyrimidinamine was dissolved in 4 ml of bromobenzene, and 300 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 82 mg of the desired product as a pale yellow solid.

Melting point: 224-226 C H-NMR(CDCl3) : δ9.66(s, 1H), 8.46(s, 1H), 7.94(s, 1H), 7.90(d, J=9.6Hz, 1H), 7.66(dd, J=9.6, 1.8Hz, 1H), 3.85(q, J=7.5Hz, 2H), 2.97(s, 3H), 1.37(t, J=7.5Hz, 3H).

Synthetic Example 14: Synthesis of 6-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)imidazo[2,1-b]thiazole (compound No. 1001a of the present disclosure) 106 mg of 5-(trifluoromethyl)thiazolamine was dissolved in 4 ml of bromobenzene, and 300 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 153 mg of the desired product as a white solid.

Melting point:219-220 C H-NMR(CDCl3) : δ9.60(s, 1H), 8.44(s, 1H), 7.97-7.94(m, 1H), 7.87(d, J=9.6Hz, 1H), 7.62(dd, J=9.6, 1.5Hz, 1H), 3.59(q, J=7.5Hz, 2H), 1.30(t, J=7.5Hz, 3H).

Synthetic Example 15: Synthesis of 2-[3-(ethylthio)methyl(trifluoromethyl)-1H- indolyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3 001b of the present disclosure) and 2-[3-(ethylsulfonyl)methyl(trifluoromethyl)-1H- indolyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3 001a of the present disclosure) Step 1: Synthesis of 1-methyl-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)-1H-indolecarboxamide 573 mg of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 608 mg of 1-methyl(trifluoromethyl)-1H-indolecarboxylic acid, 959 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 31 mg of 4- (dimethylamino)pyridine were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 1.02 g of the desired crude product as a gray solid. The crude product was used in the next step without further purification.

Step 2: Synthesis of 3-methyl[1-methyl(trifluoromethyl)-1H-indolyl] (trifluoromethyl)-3H-imidazo[4,5-b]pyridine 968 mg of the crude 1-methyl-N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)-1H-indolecarboxamide obtained in Step 1 was dissolved in 10 ml of acetic acid, and the solution was stirred under reflux with heating for 3 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 638mg of the desired product as a flesh-colored solid.

Melting point: 200-202 C H-NMR(DMSO-d6) : δ8.84(d, J=1.4Hz, 1H), 8.64(d, J=1.4Hz, 1H), 8.15(s, 1H), 7.86(d, J=8.9Hz, 1H), 7.63(dd, J=8.9, 1.4Hz, 1H), 7.46(s, 1H), 4.12(s, 3H), 4.06(s, 3H).

Step 3: Synthesis of 2-[3-iodomethyl(trifluoromethyl)-1H-indolyl]methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine To a solution of 478 mg of 3-methyl[1-methyl(trifluoromethyl)-1H-indolyl]- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 8 ml of N,N-dimethylformamide, 405 mg of N-iodosuccinimide was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 7 hours. After the reaction, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 675 mg of the desired product as a white solid.

Melting point: 165-167 C H-NMR(CDCl ) : δ8.82(d, J=1.4Hz, 1H), 8.43(d, J=1.4Hz, 1H), 7.90-7.87(m, 1H), 7.66(dd, J=8.7, 1.4Hz, 1H), 7.52(d, J=8.7Hz, 1H), 3.97(s, 3H), 3.85(s, 3H).

Step 4: Synthesis of 2-[3-(ethylthio)methyl(trifluoromethyl)-1H-indolyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3001b of the present disclosure) To a solution of 626 mg of 2-[3-iodomethyl(trifluoromethyl)-1H-indolyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 10 ml of 1,4-dioxane, 154 mg of diisopropylethylamine, 69 mg of 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene, 54 mg of tris(dibenzylideneacetone)dipalladium(0) and 111 mg of ethanethiol were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 1.5 hours. After the reaction, the reaction mixture was subjected to filtration through Celite, and the Celite was washed with chloroform. The resulting filtrate and washing solution were put together, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 545 mg of the desired product as a pale yellow solid.

Melting point: 153-155 C H-NMR(CDCl ) : δ8.80(s, 1H), 8.40(s, 1H), 8.19(s, 1H), 7.65(d, J=8.5Hz, 1H), 7.55(d, J=8.5Hz, 1H), 3.95(s, 3H), 3.85(s, 3H), 2.59(q, J=7.4Hz, 2H), 1.00(t, J=7.4Hz, 3H).

Step 5: Synthesis of 2-[3-(ethylsulfonyl)methyl(trifluoromethyl)-1H-indolyl]- 3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3001a of the present disclosure) To a solution of 250 mg of 2-[3-(ethylthio)methyl(trifluoromethyl)-1H-indol yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 5 ml of chloroform, 333 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml).

The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 245 mg of the desired product as a white solid.

Melting point: 143-146 C H-NMR(CDCl3) : δ8.83(s, 1H), 8.50(s, 1H), 8.40(d, =1.7Hz, 1H), 7.75(dd, J=8.5, 1.7Hz, 1H), 7.63(d, J=8.5Hz, 1H), 3.88(s, 3H), 3.73(s, 3H), 3.30-3.11(m, 2H), 1.27(t, J=7.2Hz, 3H).

Synthetic Example 16: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)benzo[b]thiophen- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3002b of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)benzo[b]thiophenyl]- 3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3002a of the present disclosure) Step 1: Synthesis of N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)benzo[b]thiophenecarboxamide 573 mg of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 615 mg of 5-(trifluoromethyl)benzo[b]thiophenecarboxylic acid, 959 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 31 mg of 4- (dimethylamino)pyridine were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 939 mg of the desired crude product as a gray solid. The crude product was used in the next step without further purification.

Step 2: Synthesis of 3-methyl(trifluoromethyl)[5- (trifluoromethyl)benzo[b]thiophenyl]-3H-imidazo[4,5-b]pyridine 877 mg of the crude N-[2-(methylamino)(trifluoromethyl)pyridinyl] (trifluoromethyl)benzo[b]thiophenecarboxamide obtained in Step 1 was dissolved in ml of acetic acid, and the solution was stirred under reflux with heating for 3 hours.

After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 683 mg of the desired product as a flesh-colored solid.

Melting point: 191-193 C H-NMR(DMSO-d6) : δ8.83-8.79(m, 1H), 8.62-8.59(m, 1H), 8.53(s, 1H), 8.44(s, 1H), 8.36(d, J=8.5Hz, 1H), 7.80(d, J=8.5Hz, 1H), 4.24(s, 3H).

Step 3: Synthesis of 2-[3-chloro(trifluoromethyl)benzo[b]thiophenyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine To a solution of 400 mg of 3-methyl(trifluoromethyl)[5- (trifluoromethyl)benzo[b]thiophenyl]-3H-imidazo[4,5-b]pyridine in 5 ml of N,N- dimethylformamide, 590 mg of 1,3-dichloro-5,5-dimethylhydantoin was added at 80 C.

After the addition, the reaction mixture was stirred at 80 C for 1.5 hours. After the reaction, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 390 mg of the desired product as a white solid.

Melting point: 158-160 C H-NMR(CDCl3) : δ8.81-8.77(m, 1H), 8.41-8.38(m, 1H), 8.29-8.26(m, 1H), 8.06(d, J=8.5Hz, 1H), 7.80(d, J=8.5Hz, 1H), 4.04(s, 3H).

Step 4: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)benzo[b]thiophenyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3002b of the present disclosure) To a solution of 370 mg of 2-[3-chloro(trifluoromethyl)benzo[b]thiophenyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 5 ml of N,N-dimethylformamide, 119 mg of sodium ethanethiolate was added at 80 C. After the addition, the reaction mixture was stirred at 80 C for 1.5 hours. After the stirring, 159 mg of sodium ethanethiolate was added to the reaction mixture at 80 C. After the reaction, the reaction mixture was mixed with 20 ml of water and extracted with ethyl acetate (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 186 mg of the desired product as a yellow solid.

Melting point: 120-122 C H-NMR(CDCl ) : δ8.78(s, 1H), 8.41(s, 1H), 8.38(d, J=1.8Hz, 1H), 8.06(d, J=8.6Hz, 1H), 7.77-7.74(m, 1H), 3.96(s, 3H), 2.69(q, J=7.4Hz, 2H), 1.05(t, J=7.4Hz, 3H).

Step 5: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)benzo[b]thiophenyl]- 3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 3002a of the present disclosure) To a solution of 147 mg of 2-[3-(ethylthio)(trifluoromethyl)benzo[b]thiophen yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 3 ml of chloroform, 195 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addtion, the reaction mixture was stirred at room temperature for 4 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml).

The resulting organic layer was washed with a 1M sodium hydorxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 104 mg of the desired product as a white solid.

Melting point: 70-75 C H-NMR(CDCl ) : δ8.85(s, 1H), 8.79(d, J=1.5Hz, 1H), 8.35(d, J=1.8Hz, 1H), 8.13(d, J=8.6Hz, 1H), 7.85(dd, J=8.6, 1.8Hz, 1H), 3.89(s, 3H), 3.38(q, J=7.5Hz, 2H), 1.32(t, J=7.5Hz, 3H).

Synthetic Example 17: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine (compound No. 1002b of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine (compound No. 1002a of the present disclosure) Step 1: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] (trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine (compound No. 1002b) A solution of 400 mg of 3-nitro(trifluoromethyl)picolinaldehyde and 522 mg of 3- (ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinamine in 5 ml of xylene was stirred under reflux with heating for one hour. After the stirring, 1.50 g of triethyl phosphite was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for one hour. After the reaction, the solvent was evaporated from the reaction mixture. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 613 mg of the desired product as a pale yellow solid.

Melting point: 161-163 C H-NMR(CDCl3) : δ9.43-9.41(m, 1H), 8.85(d, J=2.1Hz, 1H), 8.76(d, J=7.4Hz, 1H), 8.53-8.49(m, 1H), 8.05-8.00(m, 1H), 7.30-7.20(m, 1H), 2.99(q, J=7.5Hz, 2H), 1.21(t, J=7.5Hz, 3H).

Step 2: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl](trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine (compound No. 1002a of the present disclosure) To a solution of 150 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl](trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine in 5 ml of chloroform, 204 mg of m- chloroperbenzoic acid (containing 35 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours.

After the stirring, 40 mg of m-chloroperbenzoic acid (containing 35 weight% of water) was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred at room temeprature for 2 hours. After the reaction, the reaction mixture was mixed with 3 ml of a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 61 mg of the desired product as a white solid.

Melting point: 245-247 C H-NMR(CDCl3) : δ9.44(d, J=7.2Hz, 1H), 9.17-9.15(m, 1H), 8.86(d, J=1.8Hz, 1H), 8.48-8.43(m, 1H), 8.13-8.09(m, 1H), 7.35-7.30(m, 1H), 4.04(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).

Synthetic Example 18: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine (compound No. 1001b of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine (compound No. 1001a of the present disclosure) Step 1: Synthesis of 4-azido(trifluoromethyl)nicotinaldehyde To a solution of 1.50 g of 4-chloro(trifluoromethyl)nicotinaldehyde in 10 ml of N,N-dimethylformamide, 511 mg of sodium azide was added under cooling with ice.

After the addition, the reaction mixture was stirred at room temperature for 3 hours.

After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with diethyl ether (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 80:20) as the eluent to obtain 2.13 g of the desired product as a white solid.

Melting point: 54-56 C H-NMR(CDCl ) : δ10.39(s, 1H), 9.06(s, 1H), 7.54(s, 1H).

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] (trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine (compound No. 1001b of the present disclosure) To a solution of 200 mg of 4-azido(trifluoromethyl)nicotinaldehyde and 266 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinamine in 5 ml of dichloromethane, 282 mg of triethylamine and 1 ml of 0.56 ml of about 1M titanium(IV) chloride in dichloromethane were successively added. After the addition, the reaction mixture was stirred at room temperature for one hour. After the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was subjected to filtration through Celite, and the Celite was washed with 20 ml of xylene. The resulting washing solution was stirred under reflux with heating for 2 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (20 ml×2). The resulting organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 250 mg of the desired product as a pale yellow solid.

Melting point: 183-185 C H-NMR(CDCl ) : δ9.40-9.37(m, 1H), 9.29(d, J=0.9Hz, 1H), 8.77(d, J=7.4Hz, 1H), 8.14(s, 1H), 8.04-7.99(m, 1H), 7.30-7.25(m, 1H), 3.02(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl](trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine (compound No. 1001a of the present disclosure) To a solution of 120 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl](trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine in 5 ml of chloroform, 164 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2).

The resulting organic layer was washed with the saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 63 mg of the desired product as a white solid.

Melting point: 230-233 C H-NMR(CDCl3) : δ9.43(d, J=7.4Hz, 1H), 9.41-9.37(m, 1H), 9.07(s, 1H), 8.12- 8.06(m, 2H), 7.36(dd, J=7.4, 1.8Hz, 1H), 4.03(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).

Synthetic Example 19: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)thiazolo[5,4-b]pyridine (compound No. 1001b of the present disclosure) and 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridinyl]- 6-(trifluoromethyl)thiazolo[5,4-b]pyridine (compound No. 1001a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[2-mercapto(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 500 mg of 3-amino(trifluoromethyl)pyridinethiol was dissolved in 5 ml of pyridine, and 621 mg of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid, 820 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride and 10 mg of 1-hydroxybenzotriazole were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. Afte the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 234 mg of the desired crude product as a brown solid.

The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] (trifluoromethyl)thiazolo[5,4-b]pyridine (compound No. 1001b of the present disclosure) 214 mg of the crude 3-(ethylthio)-N-[2-mercapto(trifluoromethyl)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 5 ml of propionic acid, and the solution was stirred under reflux with heating for 4 hours. After the stirring, the reaction mixture was stirred at room temeprature overnignt. After the reaction, water was added to the reaction mixture and extracted with ethyl acetate (10 ml×2). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 20 mg of the desired product as a white solid.

Melting point: 150-160 C H-NMR(CDCl3) : δ8.91-8.87(m, 1H), 8.71(d, J=7.5Hz, 1H), 8.65-8.61(m, 1H), 8.06(s, 1H), 7.20(dd, J=7.5, 1.5Hz, 1H), 3.08(q, J=7.4Hz, 2H), 1.27(t, J=7.4Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl](trifluoromethyl)thiazolo[5,4-b]pyridine (compound No. 1001a of the present disclosure) To a solution of 20 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl](trifluoromethyl)thiazolo[5,4-b]pyridine in 3 ml of chloroform, 27 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2).

The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 15 mg of the desired product as a white solid.

Melting point: 243-245 C H-NMR(CDCl3) : δ9.53(d, J=7.5Hz, 1H), 8.95-8.93(m, 1H), 8.63-8.61(m, 1H), 8.17-8.14(m, 1H), 7.30(dd, J=7.5, 1.9Hz, 1H), 4.10(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).

Synthetic Example 20: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]iodomethyl-3H-imidazo[4,5-b]pyridine (compound No. 1026b of the present disclosure), 2-ethylhexyl((2-(3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl)methyl-3H-imidazo[4,5-b]pyridinyl)thio)propanoate (compound No. 1- 1-028b of the present disclosure), 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine (compound No. 1027b of the present disclosure) and 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl((trifluoromethyl)thio)-3H- imidazo[4,5-b]pyridine (compound No. 1027a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[5-iodo(methylamino)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 1.59 g of 5-iodo-N -methylpyridine-2,3-diamine was dissolved in 15 ml of pyridine, and 1.54 g of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid and 2.45 g of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 2.49 g of the desired crude product as a gray solid. The crude product was used in the next step without further purification.

H-NMR(CDCl3) : δ8.97(brs, 1H), 8.71(d, J=7.2Hz, 1H), 8.27(d, J=2.0Hz, 1H), 8.07(d, J=2.0Hz, 1H), 7.96(s, 1H), 7.19(dd, J=7.2, 2.0Hz, 1H), 4.78(brs, 1H), 3.08(q, J=7.4Hz, 2H), 3.03(d, J=4.8Hz, 3H), 1.22(t, J=7.4Hz, 3H).

Step 2: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] iodomethyl-3H-imidazo[4,5-b]pyridine (compound No. 1026b of the present disclosure) 2.49 g of the crude 3-(ethylthio)-N-[5-iodo(methylamino)pyridinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 15 ml of acetic acid, and the solution was stirred under reflux with heating for 3.5 hours. After the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was washed with n- hexane to obtain 2.02 g of the desired product as a brown solid.

Melting point: 230-233 C H-NMR(CDCl ) : δ8.76(d, J=7.2Hz, 1H), 8.62(d, J=1.7Hz, 1H), 8.47(d, J=1.7Hz, 1H), 8.03(s, 1H), 7.19(dd, J=7.2, 1.7Hz, 1H), 4.25(s, 3H), 3.11(q, J=7.5Hz, 2H), 1.20(t, J=7.5Hz, 3H).

Step 3: Synthesis of 2-ethylhexyl 3-((2-(3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl)methyl-3H-imidazo[4,5-b]pyridinyl)thio)propanoate (compound No. 1- 1-028b of the present disclosure) To a solution of 503 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl]iodomethyl-3H-imidazo[4,5-b]pyridine in 10 ml of 1,4-dioxane, 387 mg of diisopropylethylamine, 58 mg of 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene, 92 mg of tris(dibenzylideneacetone)dipalladium(0) and 262 mg of 2-ethylhexyl 3- mercaptopropionate were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 4 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with diethyl ether (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 80:20) as the eluent to obtain 599 mg of the desired product as a yellow solid.

Melting point: 94-96 C H-NMR(CDCl ) : δ8.76(d, J=7.2Hz, 1H), 8.53(d, J=2.0Hz, 1H), 8.27(d, J=2.0Hz, 1H), 8.03(s, 1H), 7.18(dd, J=7.2, 1.9Hz, 1H), 4.27(s, 3H), 4.01(dd, J=5.8, 1.7Hz, 2H), 3.20-3.05(m, 4H), 2.62(t, J=7.3Hz, 2H), 1.45-1.20(m, 12H), 0.89(t, J=7.5Hz, 6H).

Step 4: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine (compound No. 1027b of the present disclosure) Under a nitrogen atmosphere, to a solution of 560 mg of 2-ethylhexyl 3-((2-(3- (ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl)methyl-3H-imidazo[4,5- b]pyridinyl)thio)propanoate in 5 ml of tetrahydrofuran, 159 mg of potassium tert- butoxide was added under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the stirring, to the reaction mixture, 756 mg of S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the reaction mixture was mixed with water and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The resulting residue was purified by thin layer chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 80:20) as the eluent to obtain 69 mg of the desired product as a pale yellow solid.

Melting point: 209-210 C H-NMR(CDCl3) : δ8.77(d, J=7.2Hz, 1H), 8.66(d, J=2.0Hz, 1H), 8.46(d, J=2.0Hz, 1H), 8.05-8.02(m, 1H), 7.20(dd, J=7.2, 1.9Hz, 1H), 4.31(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).

Step 5: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl]methyl((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine (compound No. 1027a of the present disclosure) To a solution of 31 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl]methyl((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine in 3 ml of chloroform, 38 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 34 mg of the desired product as a white solid.

Melting point: 220-223 C H-NMR(CDCl ) : δ9.41(d, J=7.4Hz, 1H), 8.70(d, J=2.0Hz, 1H), 8.41(d.J=2.0Hz, 1H), 8.14(s, 1H), 7.31(dd, J=7.4, 1.6Hz, 1H), 4.16(s, 3H), 4.11(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).

Synthetic Example 21: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine 4-oxide (compound No. 1001a of the present disclosure) To a solution of 500 mg of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 15 ml of acetonitrile, 834 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at 50 C for 20 hours. After the stirring, 279 mg of 65 weight% m- chloroperbenzoic acid (containing about 30 weight% of water) was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred at 50 C for 20 hours. After the stirring, 418 mg of 65 weight% m- chloroperbenzoic acid (containing about 30 weight% of water) was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred to 50 C for 20 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (20 ml×2).

The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate with a gradient of from 100:0 to 0:100) as the eluent to obtain 67 mg of the desired product as a white solid.

H-NMR(CDCl3) : δ9.35(d, J=7.2Hz, 1H), 8.48-8.46(m, 1H), 8.19-8.16(m, 1H), 7.96(s, 1H), 7.35(dd, J=7.2, 1.7Hz, 1H), 4.58(s, 3H), 3.94(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).

Synthetic Example 22: Synthesis of 8-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]methyl-(trifluoromethyl)-9H-imidazo[4,5-c]pyridazine (compound No. 1- 16-001b of the present disclosure) and 8-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl-(trifluoromethyl)-9H-imidazo[4,5- c]pyridazine (compound No. 1001a of the present disclosure) Step 1: Synthesis of 3-(ethylthio)-N-[3-(methylamino)(trifluoromethyl)pyridazin- 4-yl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide 300 mg of 4-bromo-N-methyl(trifluoromethyl)pyridazinamine, 509 mg of 3- (ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine-carboxamide, 497 mg of potassium phosphate and 52 mg of N,N’-dimethylethylenediamine were dissolved in 4 ml of N,N- dimethylformamide, and 56 mg of copper(I) iodide was added at room temperature.

After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred at 90 C for 9 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain crude 3-(ethylthio)-N-[3-(methylamino)(trifluoromethyl)pyridazin yl](trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide as the desired product.

The crude product was used in the next step without further purification.

Step 2: Synthesis of 8-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinyl] methyl-(trifluoromethyl)-9H-imidazo[4,5-c]pyridazine (compound No. 1001b of the present disclosure) The crude 3-(ethylthio)-N-[3-(methylamino)(trifluoromethyl)pyridazinyl] (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 10 ml of acetic acid, and the solution was stirred under reflux with heating for 7 hours.

After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and then with 28 weight% aqueous ammonia, dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n- hexane/ethyl acetate (with a gradient of from 100:0 to 25:75) as the eluent to obtain 72 mg of the desired product as a pale yellow solid.

Melting point: 240-242 C H-NMR(CDCl3) : δ9.05-9.00(m, 1H), 8.23(s, 1H), 7.85(d, J=9.8Hz, 1H), 7.56(dd, J=9.4, 1.6Hz, 1H), 4.55(s, 3H), 3.16(q, J=7.4Hz, 2H), 1.25(t, J=7.4Hz, 3H).

Step 3: Synthesis of 8-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl]methyl-(trifluoromethyl)-9H-imidazo[4,5-c]pyridazine (compound No. 1001a of the present disclosure) To a solution of 62 mg of 8-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl]methyl-(trifluoromethyl)-9H-imidazo[4,5-c]pyridazine in 5 ml of chloroform, 81 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for one hour. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml).

The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 25:75) as the eluent to obtain 66 mg of the desired product as a pale yellow solid.

Melting point: 274-276 C H-NMR(CDCl3) : δ9.70-9.60(m, 1H), 8.22(s, 1H), 7.99(d, J=9.4Hz, 1H), 7.75(dd, J=9.4, 1.6Hz, 1H), 4.38(s, 3H), 4.05(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).

Synthetic Example 23: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyrimidinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1054b of the present disclosure) and 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyrimidinyl]methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridine (compound No. 1054a of the present disclosure) Step 1: Synthesis of 3-methyl(trifluoromethyl)[6-(trifluoromethyl)imidazo[1,2- a]pyrimidinyl]-3H-imidazo[4,5-b]pyridine 250 mg of 5-(trifluoromethyl)pyrimidinamine was dissolved in 10 ml of acetonitrile, and 550 mg of 2-bromo[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 7.5 hours. After the reaction, ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 445 mg of the desired product as a yellow solid.

Melting point: 283-285 C H-NMR(CDCl ) : δ8.92-8.89(m, 1H), 8.84(d, J=2.4Hz, 1H), 8.73(s, 1H), 8.57(s, 1H), 8.29(s, 1H), 4.53(s, 3H).

Step 2: Synthesis of 2-[3-iodo(trifluoromethyl)imidazo[1,2-a]pyrimidinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine To a solution of 415 mg of 3-methyl(trifluoromethyl)[6- (trifluoromethyl)imidazo[1,2-a]pyrimidinyl]-3H-imidazo[4,5-b]pyridine in 4 ml of N,N- dimethylformamide, 408 mg of 1,3-diiodo-5,5-dimethylhydantoin was added at 80 C.

After the addition, the reaction mixture was stirred at 80 C for 3 hours. After the reaction, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 468 mg of the desired product as a yellow solid.

Melting point: 260-265 C H-NMR(CDCl3) : δ9.00-8.86(m, 1H), 8.81(d, J=2.4Hz, 1H), 8.74(d, J=1.5Hz, 1H), 8.42(d, J=1.5Hz, 1H), 4.43(s, 3H).

Step 3: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyrimidin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1054b of the present disclosure) To a solution of 438 mg of 2-[3-iodo(trifluoromethyl)imidazo[1,2-a]pyrimidin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 10 ml of 1,4-dioxane, 334 mg of diisopropylethylamine, 50 mg of 4,5’-bis(diphenylphosphino)-9,9’-dimethylxathene, 39 mg of tris(dibenzylideneacetone)dipalladium(0) and 106 mg of ethanethiol were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 3 hours. After the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was washed with diisopropyl ether to obtain 337 mg of the desired product as a yellow solid.

Melting point: 220-222 C H-NMR(CDCl3) : δ9.27-9.23(m, 1H), 8.88(d, J=2.1Hz, 1H), 8.75(s, 1H), 8.42(s, 1H), 4.42(s, 3H), 3.25(q, J=7.5Hz, 2H), 1.26(t, J=7.5Hz, 3H).

Step 4: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyrimidin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1054a of the present disclosure) To a solution of 297 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyrimidinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 7 ml of chloroform, 371 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 3.5 hours. After the stirring, m- chloroperbenzoic acid (containing 35 weight% of water) was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred at room temperature for one hour. After the stirring, 50 mg of m-chloroperbenzoic acid (containing 35 weight% of water) was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred at room temperature for one hour. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 150 mg of the desired product as a white solid.

Melting point: 244-248 C H-NMR(CDCl3) : δ10.00-9.95(m, 1H), 9.04(d, J=2.4Hz, 1H), 8.80(s, 1H), 8.41- 8.37(m, 1H), 4.30(s, 3H), 4.27(q, J=7.5Hz, 2H), 1.49(t, J=7.5Hz, 3H).

Synthetic Example 24: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- c]pyrimidinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1055b of the present disclosure) and 2-[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-c]pyrimidinyl]methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridine (compound No. 1055a of the present disclosure) Step 1: Synthesis of 3-methyl(trifluoromethyl)[7-(trifluoromethyl)imidazo[1,2- c]pyrimidinyl]-3H-imidazo[4,5-b]pyridine 251 mg of 6-(trifluoromethyl)pyrimidinamine was dissolved in 10 ml of acetonitrile, and 550 mg of 2-bromo[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 7.5 hours. After the reaction, 10 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 335 mg of the desired product as a yellow solid.

Melting point: 257-260 C H-NMR(CDCl ) : δ9.22(s, 1H), 8.73(d, J=1.2Hz, 1H), 8.64(s, 1H), 8.29(d, J=1.8Hz, 1H), 8.05(s, 1H), 4.47(s, 3H).

Step 2: Synthesis of 2-[3-bromo(trifluoromethyl)imidazo[1,2-c]pyrimidinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine To a solution of 300 mg of 3-methyl(trifluoromethyl)[7- (trifluoromethyl)imidazo[1,2-c]pyrimidinyl]-3H-imidazo[4,5-b]pyridine in 5 ml of N,N- dimethylformamide, 244 mg of 1,3-dibromo-5,5-dimethylhydantoin was added at 80 C.

After the addition, the reaction mixture was stirred at 80 C for 30 minutes. After the reaction, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 468 mg of the desired crude product as a yellow solid. The crude product was used in the next step without further purification.

H-NMR(CDCl ) : δ9.27(s, 1H), 8.75(d, J=0.9Hz, 1H), 8.43(d, J=1.5Hz, 1H), 8.02(s, 1H), 4.37(s, 3H).

Step 3: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-c]pyrimidin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1055b of the present disclosure) To a solution of 452 mg of the crude 2-[3-bromo(trifluoromethyl)imidazo[1,2- c]pyrimidinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine obtained in Step 2 in 10 ml of 1,4-dioxane, 377 mg of diisopropylethylamine, 56 mg of 4,5’- bis(diphenylphosphino)-9,9’-dimethylxanthene, 44 mg of tris(dibenzylideneacetone)dipalladium(0) and 121 mg of ethanethiol were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 6.5 hours. After the stirring, to the reaction mixture, 754 mg of diisopropylethylamine, 112 mg of 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene, 88 mg of tris(dibenzylideneacetone)dipalladium(0) and 242 mg of ethanethiol were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 5 hours. After the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was washed with diisopropyl ether to obtain 371 mg of the desired product as a brown solid.

Melting point: 198-200 C H-NMR(CDCl ) : δ9.54(s, 1H), 8.77-8.73(m, 1H), 8.41(s, 1H), 8.01(s, 1H), 4.32(s, 3H), 3.24(q, J=7.5Hz, 2H), 1.26(t, J=7.5Hz, 3H).

Step 4: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-c]pyrimidin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1055a of the present disclosure) To a solution of 315 mg of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- c]pyrimidinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine obtained in Step 3 in 10 ml of chloroform, 412 mg of 65 weight% m-chloroperbenzoic acid (containin about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 3 hours. After the stirring, 206 mg of m-chloroperbenzoic acid (containing 35 weight% of water) was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 139 mg of the desired product as a white solid.

Melting point: 238-240 C H-NMR(CDCl ) : δ10.15(s, 1H), 8.80(s, 1H), 8.39(s, 1H), 8.15(s, 1H), 4.22(s, 3H), 4.22(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H).

Synthetic Example 25: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl](trifluoromethyl)imidazo[1,2-a]pyrazine (compound No. 1002a of the present disclosure) 103 mg of 5-(trifluoromethyl)pyrazinamine was dissolved in 4 ml of bromobenzene, and 300 mg of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone was added at room temperature.

The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 38 mg of the desired product as a white solid.

Melting point: 266-270 C H-NMR(CDCl ) : δ9.63(s, 1H), 9.24(s, 1H), 8.68(s, 1H), 8.62(s, 1H), 7.93(d, J=9.3Hz, 1H), 7.66(dd, J=9.3, 1.8Hz, 1H), 3.70(q, J=7.5Hz, 2H), 1.35(t, J=7.5Hz, 3H).

Synthetic Example 26: Synthesis of 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]- 6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1012b of the present disclosure), 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1006b of the present disclosure) and 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-1H-imidazo[4,5-c]pyridine (compound No. 1003b of the present disclosure) Step 1: Synthesis of N-[5-amino(trifluoromethyl)pyridinyl]chloro (ethylthio)imidazo[1,2-a]pyridinecarboxamide 470 mg of 6-(trifluoromethyl)pyridine-3,4-diamine was dissolved in 7 ml of pyridine, and 486 mg of 7-chloro(ethylthio)imidazo[1,2-a]pyridinecarboxylic acid and 752 mg of 1-ethyl(3-dimethylaminopropyl)carbodiimide hydrochloride were added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 749 mg of the desired crude product as a pale solid. The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl] (trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1012b of the present disclosure) 749 mg of the crude N-[5-amino(trifluoromethyl)pyridinyl]chloro (ethylthio)imidazo[1,2-a]pyridinecarboxamide obtained in Step 1 was dissolved in 7 ml of propionic acid, and the solution was stirred under reflux with heating for 20 hours.

After the stirring, the solid precipitated in the reaction mixture was collected by filtration.

The resulting solid was washed with water to obtain 761 mg of the desired product as a brown solid. The product was used in the next step without futher purification.

Step 3: Synthesis of 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1006b of the present disclosure) and 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-1H-imidazo[4,5-c]pyridine (compound No. 1003b of the present disclosure) To a solution of 219 mg of 63 weight% sodium hydroxide (dispersed in mineral oil) in 10 ml of N,N-dimethylformamide, a solution of 761 mg of 2-[7-chloro (ethylthio)imidazo[1,2-a]pyridinyl](trifluoromethyl)-3H-imidazo[4,5-c]pyridine in 10 ml of N,N-dimethylformamide was added under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the stirring, 940 mg of methyl trifluoromethanesulfonate was added to the reaction mixture under cooling with ice. After the addition, the reaction mixture was stirred to room temperature for one hour. After the reaction, the reaction mixture was mixed with 20 ml of water and extracted with diethyl ether (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n- hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 65 mg of the desired 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-3H-imidazo[4,5-c]pyridine and 247 mg of the desired 2-[7-chloro (ethylthio)imidazo[1,2-a]pyridinyl]methyl(trifluoromethyl)-1H-imidazo[4,5- c]pyridine respectively as a white solid.

Melting point of 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-3H-imidazo[4,5-c]pyridine: 215-217 ℃ H-NMR(CDCl ) : δ8.95(s, 1H), 8.59(d, J=7.5Hz, 1H), 8.19(s, 1H), 7.74-7.71(m, 1H), 7.03(dd, J=7.5, 2.1Hz, 1H), 4.33(s, 3H), 3.09(q, J=7.5Hz, 2H), 1.19(t, J=7.5Hz, 3H).

Melting point of 2-[7-chloro(ethylthio)imidazo[1,2-a]pyridinyl]methyl (trifluoromethyl)-1H-imidazo[4,5-c]pyridine: 187-188 ℃ H-NMR(CDCl3) : δ9.24(s, 1H), 8.59(dd, J=7.2, 0.6Hz, 1H), 7.81(s, 1H), 7.73- 7.69(m, 1H), 7.03(dd, J=7.2, 1.8Hz, 1H), 4.26(s, 3H), 3.10(q, J=7.5Hz, 2H), 1.20(t, J=7.5Hz, 3H).

Synthetic Example 27: Synthesis of 2-[3-(ethylthio)iodo (trifluoromethyl)imidazo[1,2-a]pyridinyl]methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridine (compound No. 1066b of the present disclosure) Step 1: Synthesis of 2-(ethylthio)[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl]ethanone To a solution of 20 g of 2-bromo[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl]ethanone in 80 ml of N,N-dimethylformamide, 4.2 g of ethanethiol and 9.4 g of potassium carbonate were successively added under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the stirring, the reaction mixture was stirred at room temperature for one hour. After the reaction, the reaction mixture was mixed with 100 ml of water and extracted with ethyl acetate (100 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hecane/ethyl acetate (with a gradient of from 100:0 to 80:20) as the eluent to obtain 13.8 g of the desired product as a pale yellow solid.

Melting point: 67-69 C H-NMR(CDCl ) : δ8.85-8.80(m, 1H), 8.45-8.40(m, 1H), 4.24(s, 3H), 4.07(s, 2H), 2.66(q, J=7.4Hz, 2H), 1.31(t, J=7.4Hz, 3H).

Step 2: Synthesis of 2-bromo(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl]ethanone To a solution of 11.4 g of 2-(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl]ethanone in 100 ml of dichloromethane, 4.2 g of triethylamine was added at room temperature. After the addition, the reaction mixture was cooled to -20 C, and 8.8 g of trimethylsilyl trifluoromethanesulfonate was added. After the addition, the reaction mixture was stirred under cooling with ice for 20 minutes. After the stirring, the reaction mixture was cooled to -20 C, and 14.1 g of trimethylphenylammonium tribromide was added. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the reaction, the reaction mixture was added dropwise to 100 ml of water under cooling with ice, and the mixture was extracted with chloroform (100 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 13.4 g of the desired product as a reddish brown oil.

H-NMR(CDCl ) : δ8.90-8.80(m, 1H), 8.50-8.40(m, 1H), 7.14(s, 1H), 4.27(s, 3H), 3.05-2.80(m, 2H), 1.39(t, J=7.6Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylthio)iodo(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1066b of the present disclosure) 300 mg of 5-iodo(trifluoromethyl)pyridinamine was dissolved in 8 ml of propionitrile, and 345 mg of 2-bromo(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 1.5 hours. After the reaction, the reaction mixture was mixed with 20 ml of water and extracted with chloroform (20 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. 10 ml of diisopropyl ether was added to the precipitated solid, followed by filtration to obtain 294 mg of the desired product as an orange solid.

Melting point: 222-225 C H-NMR(CDCl3) : δ9.10-9.00(m, 1H), 8.75-8.70(m, 1H), 8.40-8.35(m, 1H), 7.90- 7.85(m, 1H), 4.35(s, 3H), 3.18(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).

Synthetic Example 28: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- b]pyridazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1057b of the present disclosure), 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- b]pyridazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1057a of the present disclosure) and 2-[3-(ethylsulfinyl) (trifluoromethyl)imidazo[1,2-b]pyridazinyl]methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridine (compound No. 1057c of the present disclosure) Step 1: Synthesis of 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-b]pyridazin yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1057b of the present disclosure) 42 mg of 5-(trifluoromethyl)pyridazinamine was dissolved in 3 ml of acetonitrile, and 100 mg of 2-bromo(ethylthio)[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 2 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 130 mg of the desired crude product. The crude product was used in the next step without further purification.

Step 2: Synthesis of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-b]pyridazin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1057a of the present disclosure) and 2-[3-(ethylsulfinyl)(trifluoromethyl)imidazo[1,2- b]pyridazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound No. 1057c of the present disclosure) To a solution of 120 mg of the crude 2-[3-(ethylthio)(trifluoromethyl)imidazo[1,2- b]pyridazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine obtained in Step 1 in 10 ml of chloroform, 99 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulding residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 70 mg of the desired 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- b]pyridazinyl]methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine and 41 mg of the desired 2-[3-(ethylsulfinyl)(trifluoromethyl)imidazo[1,2-b]pyridazinyl]methyl (trifluoromethyl)-3H-imidazo[4,5-b]pyridine respectively as a pale yellow oil.

H-NMR of 2-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-b]pyridazinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine: δ8.90(d, J=1.8Hz, 1H), 8.79(d, J=1.5Hz, 1H), 8.55-8.50(m, 1H), 8.42(d, J=2.1Hz, 1H), 4.02(s, 3H), 3.75(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).

H-NMR of 2-[3-(ethylsulfinyl)(trifluoromethyl)imidazo[1,2-b]pyridazinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridine: δ8.82(d, J=2.1Hz, 1H), 8.78- 8.74(m, 1H), 8.49-8.45(m, 1H), 8.42-8.38(m, 1H), 4.36(s, 3H), 4.18-4.00(m, 1H), 3.85- 3.70(m, 1H), 1.55(t, J=7.5Hz, 3H).

Synthetic Example 29: Synthesis of 5-(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole (compound No. 2002b of the present disclosure) and 5-(ethylsulfonyl)[3-methyl (trifluoromethyl)-3H-imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1- b][1,3,4]thiadiazole (compound No. 2002a of the present disclosure) Step 1: Synthesis of 5-(ethylthio)[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl](trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole (compound No. 2 002b of the present disclosure) 195 mg of 5-(trifluoromethyl)-1,3,4-thiadiazolamine was dissolved in 5 ml of propionitrile, and 400 mg of 2-bromo(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 3 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n- hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 130 mg of the desired product as a white solid.

H-NMR(CDCl ) : δ8.82(d, J=1.2Hz, 1H), 8.43(d, J=1.2Hz, 1H), 4.24(s, 3H), 2.66(q, J=7.5Hz, 2H), 1.31(t, J=7.5Hz, 3H).

Step 2: Synthesis of 5-(ethylsulfonyl)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole (compound No. 2002a of the present disclosure) To a solution of 130 mg of 5-(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl](trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole in 10 ml of chloroform, 191 mg of 65 weight% m-chloroperbenzoic acid (containing about 30 weight% of water) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the reaction mixture was mixed with a saturated sodium thiosulfate aqueous solution and extracted with chloroform (10 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 52 mg of the desired product as a white solid.

Melting point: 231-234 C H-NMR(CDCl ) : δ8.76(s, 1H), 8.35(s, 1H), 4.11(s, 3H), 3.92(q, J=7.5Hz, 2H), 1.51(t, J=7.5Hz, 3H).

Synthetic Example 30: Synthesis of 2-[3-(ethylthio)fluoroiodoimidazo[1,2-a]pyridin- 2-yl]methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1008b of the present disclosure) Step 1: Synthesis of 2-(ethylthio)[3-methyl(trifluoromethyl)-3H-imidazo[4,5- c]pyridinyl]ethanone To 2.36 g of 2-bromo[3-methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridin yl]ethanone in 25 ml of N,N-dimethylformamide, 546 mg of ethanethiol and 1.21 g of potassium carbonate were successively added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for one hour. After the reaction, the reaction mixture was mixed with 50 ml of water and extracted with ethyl acetate (50 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 80:20) as the eluent to obtain 1.70 g of the desired product as a white solid.

Melting point: 90-93 C H-NMR(CDCl3) : 9.03(s, 1H), 8.19(d, J=1.0Hz, 1H), 4.29(s, 3H), 4.08(s, 2H), 2.65(q, J=7.4Hz, 2H), 1.32(t, J=7.4Hz, 3H).

Step 2: Synthesis of 2-bromo(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-c]pyridinyl]ethanone To a solution of 1.63 g of 2-(ethylthio)[3-methyl(trifluoromethyl)-3H- imidazo[4,5-c]pyridinyl]ethanone in 15 ml of dichloromethane, 600 mg of triethylamine was added at room temperature. After the addition, 1.25 g of trimethylsilyl trifluoromethanesulfonate was added to the reaction mixture under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for minutes. After the stirring, 2.02 g of trimethylphenylammonium tribromide was added to the reaction mixture under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for one hour. After the reaction, the reaction mixture was added dropwise to 20 ml of water under cooling with ice, and the mixture was extracted with chloroform (20 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.09 g of the desired product as a yellow oil.

H-NMR(CDCl ) : δ9.06(s, 1H), 8.19(s, 1H), 7.12(s, 1H), 4.31(s, 3H), 3.01-2.77(m, 2H), 1.39(t, J=7.5Hz, 3H).

Step 3: Synthesis of 2-[3-(ethylthio)fluoroiodoimidazo[1,2-a]pyridinyl] methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (compound No. 1008b of the present disclosure) 250 mg of 3-fluoroiodopyridinamine was dissolved in 5 ml of acetonitrile, and 400 mg of 2-bromo(ethylthio)[3-methyl(trifluoromethyl)-3H-imidazo[4,5- c]pyridinyl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred unde reflux with heating for one hour. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to obtain 338 mg of the desired product as a brown solid.

H-NMR(CDCl3) : δ8.96(s, 1H), 8.73(d, J=1.5Hz, 1H), 8.19(d, J=0.9Hz, 1H), 7.33(dd, J=9.0, 1.5Hz, 1H), 4.36(s, 3H), 3.15(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).

Reference Example 1: Synthesis of 2-bromo[3-(ethylsulfonyl) (trifluoromethyl)imidazo[1,2-a]pyridinyl]ethanone Step 1: Synthesis of ethyl 7-(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylate 5.0 g of 4-(trifluoromethyl)pyridinamine was dissolved in 50 ml of chlorobenzene, and 6.67 g of ethyl 3-bromooxopropanoate was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 6.5 hours. After the reaction, the reaction mixture was mixed with 20 ml of a 1M sodium hydroxide aqueous solution and extracted with ethyl acetate (20 ml×2).

The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was mixed with a 3M hydrochloric acid aqueous solution and washed with 10 ml of ethyl acetate. The aqueous layer was adjusted to have a pH of from 2 to 3 with a 10M sodium hydroxide aqueous solution and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3.94 g of the desired product as a yellow solid.

Melting point: 170-175 C H-NMR(CDCl ) : δ8.29(s, 1H), 8.27(d, J=7.2Hz, 1H), 8.01(s, 1H), 7.07(dd, J=7.2, 1.7Hz, 1H), 4.49(q, J=7.2Hz, 2H), 1.46(t, J=7.2Hz, 3H).

Step 2: Synthesis of ethyl 3-iodo(trifluoromethyl)imidazo[1,2-a]pyridine carboxylate To a solution of 3.73 g of ethyl 7-(trifluoromethyl)imidazo[1,2-a]pyridine carboxylate in 20 ml of N,N-dimethylformamide, 6.5 g N-iodosuccinimide was added at room temperature. After the addition, the reaction mixture was stirred at 80 C for 5 hours. After the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in 20 ml of chloroform, and washed with a saturated sodium thiosulfate aqueous solution and then with saturated sodium hydrogen carbonate. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 5.08 g of the desired product as a flesh-colored solid.

Melting point: 183-185 C H-NMR(CDCl ) : δ8.40(d, J=7.2Hz, 1H), 7.99(s, 1H), 7.17(dd, J=7.2, 1.7Hz, 1H), 4.53(q, J=7.2Hz, 2H), 1.50(t, J=7.2Hz, 3H).

Step 3: Synthesis of ethyl 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylate To a solution of 5.73 g of ethyl 3-iodo(trifluoromethyl)imidazo[1,2-a]pyridine carboxylate in 40 ml of 1,4-dioxane, 5.79 g of diisopropylethylamine, 862 mg of 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene, 682 mg of tris(dibenzylideneacetone)dipalladium(0) and 1.85 g of ethanethiol were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 2 hours. After the reaction, the reaction mixture was subjected to filtration through Celite, and the Celite was washed with 30 ml of chloroform. The resulting filtrate and washing solution were put together, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 5.58 g of the desired product as a brown solid.

Melting point: 50-52 C H-NMR(CDCl ) : δ8.67(d, J=7.4Hz, 1H), 8.02-8.00(m, 1H), 7.15(dd, J=7.4, 1.8Hz, 1H), 4.52(q, J=7.0Hz, 2H), 2.98(q, J=7.5Hz, 2H), 1.48(t, J=7.0Hz, 3H), 1.20(t, J=7.5Hz, 3H).

Step 4: Synthesis of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid To a solution of 5.58 g of ethyl 3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinecarboxylate in 60 ml of ethanol and 30 ml of tetrahydrofuran, 10 ml of a 3M sodium hydroxide aqueous solution was added at room temperature. After the addition, the reaction mixture was stirred at room temperature for 5 hours. After the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was mixed with a 1M hydrochloric acid aqueous solution to adjust the aqueous layer to have a pH of 2, and extracted with ethyl acetate (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3.40 g of the desired product as a yellow solid.

Melting point: 163-171 C H-NMR(CDCl3) : δ8.69(d, J=7.2Hz, 1H), 8.19(s, 1H), 7.22(dd, J=7.2, 1.4Hz, 1H), 3.06(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H) (no peak of proton of CO H was observed).

Step 5: Synthesis of 3-(ethylthio)-N-methoxy-N-methyl (trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide To a solution of 2.52 g of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid in 30 ml of dichloromethane, 3.31 g of oxalyl chloride and 30 mg of N,N- dimethylformamide were added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 3 hours. After the stirring, the solvent was evaporated from the reaction mixture under reduced pressure to obtain crude 3- (ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid chloride. The obtained crude 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid chloride was dissolved in 5 ml of dichloromethane, and the solution was added to a solution of 931 mg of N,O-dimethylhydroxylamine hydrochloride and 1.93 g of triethylamine in 15 ml of dichloromethane prepared in a separate container, under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was washed with dilute hydrochloric acid and then with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.50 g of the desired product as a flesh-colored solid.

Melting point:82-84 C H-NMR(CDCl ) : δ8.62(d, J=7.2Hz, 1H), 7.98-7.95(m, 1H), 7.14(dd, J=7.2, 1.7Hz, 1H), 3.80(s, 3H), 3.44(s, 3H), 2.91(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).

Step 6: Synthesis of 1-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl]ethanone Under a nitrogen atmosphere, to a solution of 2.45 g of 3-(ethylthio)-N-methoxy-N- methyl(trifluoromethyl)imidazo[1,2-a]pyridinecarboxamide in 25 ml of tetrahydrofuran, 2.7 ml of a solution of about 3M methylmagnesium bromide in diethyl ether was added under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for one hour. After the reaction, the reaction mixture was added dropwise to 10 ml of a 4M hydrochloric acid aqueous solution under cooling with ice and extracted with ethyl acetate (20 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.08 g of the desired product as a brown solid.

Melting point: 60-64 C H-NMR(CDCl ) : δ8.67(d, J=7.2Hz, 1H), 8.03-7.99(m, 1H), 7.15(dd, J=7.2, 1.7Hz, 1H), 3.01(q, J=7.4Hz, 2H), 2.80(s, 3H), 1.18(t, J=7.4Hz, 3H).

Step 7: Synthesis of 1-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin yl]ethanone To a solution of 2.08 g of 1-[3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridin yl]ethanone in 40 ml of methanol and 20 ml of water, 13.3 g of Oxone (registered trademark by DuPont) was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, to the reaction mixture, a solution of 2.28 g of sodium thiosulfate in 25 ml of water was added, and then a 10M sodium hydroxide aqueous solution was added to adjust the aqueous layer to be alkaline, and methanol was evaporated under reduced pressure. The resulting residue was extracted with ethyl acetate (40 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.11 g of the desired product as a yellow solid.

Melting point: 135-138 C H-NMR(CDCl ) : δ9.44(d, J=7.5Hz, 1H), 8.12-8.09(m, 1H), 7.27-7.24(m, 1H), 3.80(q, J=7.5Hz, 2H), 2.80(s, 3H), 1.35(t, J=7.5Hz, 3H).

Step 8: Synthesis of 2-bromo[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2- a]pyridinyl]ethanone To a solution of 2.05 g 1-[3-(ethylsulfonyl)(trifluoromethyl)imidazo[1,2-a]pyridin- 2-yl]ethanone in 15 ml of toluene, 10.2 g of a solution of about 5.1M hydrogen bromide in acetic acid and 1.13 g of bromine were successively added at 10 C. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the stirring, the reaction mixture was mixed with 205 mg of bromine and stirred at room temperature overnight. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (20 ml×2). The resulting organic layer was washed with a 5 weight% sodium hydrogen sulfite aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.48 g of the desired product as a yellow solid.

Melting point: 122-123 C H-NMR(CDCl ) : δ9.45(d, J=7.5Hz, 1H), 8.14-8.11(m, 1H), 7.33-7.27(m, 1H), 4.78(s, 2H), 3.78(q, J=7.4Hz, 2H), 1.37(t, J=7.4Hz, 3H).

Reference Example 2: Synthesis of 5-(ethylthio)(trifluoromethyl)imidazo[2,1- b]thiazolecarboxylic acid Step 1: Synthesis of ethyl 2-(trifluoromethyl)imidazo[2,1-b]thiazolecarboxylate 4.0 g of 5-(trifluoromethyl)thiazolamine was dissolved in 80 ml of chlorobenzene, and 7.2 g of ethyl 3-bromooxopropanoate was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 3 hours. After the stirring, 3.09 g of ethyl 3-bromooxopropanoate was added to the reaction mixture. After the addition, the reaction mixture was stirred under reflux with heating for one hour. After the stirring, 2.4 g of ethyl 3-bromo oxopropanoate was added to the reaction mixture. After the addition, the reaction mixture was stirred under reflux with heating for 2 hours. After the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was mixed with a 1M sodium hydroxide aqueous solution to adjust the aqueous layer to have a pH of 8, and extracted with ethyl acetate (20 ml×3). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The precipitated solid was collected by filtration. The resulting solid was washed with diisopropyl ether to obtain 2.12 g of the desired product as a white solid.

H-NMR(CDCl3) : δ8.14(s, 1H), 7.92(s, 1H), 4.42(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).

Step 2: Synthesis of ethyl 5-iodo(trifluoromethyl)imidazo[2,1-b]thiazole carboxylate To a solution of 7.97 g of ethyl 2-(trifluoromethyl)imidazo[2,1-b]thiazole carboxylate in 10 ml of N,N-dimethylformamide, 3.58 g of N-iodosuccinimide was added at room temperature. After the addition, the reaction mixture was stirred at 80 C for 4 hours. After the reaction, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 3.09 g of the desired product as a white solid.

H-NMR(CDCl3) : δ7.90-7.86(m, 1H), 4.44(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).

Step 3: Synthesis of ethyl 3-(ethylthio)(trifluoromethyl)imidazo[2,1-b]thiazole carboxylate To a solution of 2.00 g of ethyl 5-iodo(trifluoromethyl)imidazo[2,1-b]thiazole carboxylate in 20 ml of 1,4-dioxane, 1.98 g of diisopropylethylamine, 296 mg of 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene, 234 mg of tris(dibenzylideneacetone)dipalladium(0) and 636 mg of ethanethiol were successively added at room temperature. After the addition, the atmosphere in the reaction vessel was replaced by nitrogen gas, and the mixture was stirred under reflux with heating for 4 hours. After the reaction, the reaction mixture was subjected to filtration through Celite, and the Celite was washed with 30 ml of chloroform. The resulting filtrate and washing solution were put together, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 1.11 g of the desired product as a yellow solid.

H-NMR(CDCl3) : δ8.04-7.98(m, 1H), 4.44(q, J=7.5Hz, 2H), 2.99(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H), 1.23(t, J=7.5Hz, 3H).

Step 4: Synthesis of 5-(ethylthio)(trifluoromethyl)imidazo[2,1-b]thiazole carboxylic acid To a solution of 1.09 g of ethyl 3-(ethylthio)(trifluoromethyl)imidazo[2,1- b]thiazolecarboxylate in 10 ml of ethanol and 10 ml of tetrahydrofuran, 6.8 ml of a 1M sodium hydroxide aqueous solution was added at room temperature. After the addition, the reaction mixture was stirred at room temperature overnight. After the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was mixed with a 1M hydrochloric acid aqueous solution to adjust the aqueous layer to have a pH of from 2 to 3, and extracted with chloroform (20 ml×2).

The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 896 mg of the desired product as a yellow solid.

H-NMR(CDCl3) : 8.06-8.02(m, 1H), 3.04(q, J=7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H) (no peak of proton of CO H was observed).

Reference Example 3: The following compounds were synthesized in the same manner as in Steps 1 to 4 in Reference Example 1. 3-(Ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid Melting point: 200-201 C H-NMR(CDCl ) : δ8.93(s, 1H), 8.20(d, J=9.6Hz, 1H), 7.56(dd, J=9.6, 1.8Hz, 1H), 3.06(q.J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H) (no peak of proton of CO2H was observed). 3-(Ethylthio)(trifluoromethyl)imidazo[1,2-a]pyrazinecarboxylic acid Melting point: 175-178 C H-NMR(CDCl ) : δ9.21(s, 1H), 8.84(s, 1H), 3.08(q, J=7.2Hz, 2H), 1.22(t, J=7.2Hz, 3H) (no peak of proton of CO2H was observed).

Reference Example 4: Synthesis of N ,2-dimethyl(trifluoromethyl)pyridine-3,4- diamine Step 1: Synthesis of 4-bromomethyl(trifluoromethyl)pyridinamine To a solution of 3.0 g of 2-methyl(trifluoromethyl)pyridinamine in 30 ml of acetonitrile, 3.03 g of N-bromosuccinimide was added at room temperature. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n- hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 4.0 g of the desired product as a brown solid.

Melting point: 40-41 C H-NMR(CDCl ) : δ7.61(s, 1H), 4.40(brs, 2H), 2.52(s, 3H).

Step 2: Synthesis of 4-bromo-N,2-dimethyl(trifluoromethyl)pyridinamine To a solution of 537 mg of 63 weight% sodium hydride (dispersed in mineral oil) in ml of N,N-dimethylformamide, a solution of 3.0 g of 4-bromomethyl (trifluoromethyl)pyridinamine in 12 ml of N,N-dimethylformamide was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for one hour. After the stirring, 2.0 g of methyl iodide was added to the reaction mixture under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent to obtain 2.82 g of the desired product as a yellow oil.

H-NMR(CDCl ) : δ7.62(s, 1H), 3.01(s, 3H), 2.65(s, 3H) (no peak of proton of NH was observed).

Step 3: Synthesis of N ,2-dimethyl(trifluoromethyl)pyridine-3,4-diamine To a solution of 1.0 g of 4-bromo-N,2-dimethyl(trifluoromethyl)pyridinamine, 186 mg of acetylacetone, 243 mg of copper(II) acetylacetonate and 1.81 g of cesium carbonate in 30 ml of N-methylpyrrolidone was added to an autoclave reactor. After the addition, 20 ml of 28 weight% aqueous ammonia was added to the reaction mixture at room temperature. After the addition, the reactor was closely sealed, and the reaction mixture was heated to 140 C and stirred for one hour. After the reaction, the reaction mixture was mixed with 20 ml of water and extracted with ethyl acetate (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 0:100) as the eluent to obtain 189 mg of the desired product as a white solid.

H-NMR(CDCl3) : 6.84(s, 1H), 4.53(brs, 2H), 2.69(s, 3H), 2.50(s, 3H) (no peak of proton of NH was observed).

Reference Example 5: Synthesis of 2-methyl(perfluoroethyl)pyrimidinamine Step 1: Synthesis of (Z)-ethyl 3-ethoxy-4,4,5,5,5-pentafluoropentenoate To a solution of 20.7 g of ethyl 4,4,5,5,5-pentafluorooxovalerate in 150 ml of acetone, 24.4 g of potassium carbonate and 15.7 g of ethyl trifluoromethanesulfonate were successively added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the reaction, the reaction mixture was subjected to filtration through Celite, and the Celite was washed with 50 ml of acetone. The resulting filtrate and washing solution were put together, and the solvent was evaporated under reduced pressure. The resulting residue was mixed with 30 ml of water and extracted with hexane (30 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 20.53 g of the desired crude product as a colorless and transparent oil.

H-NMR(CDCl3) : δ5.80(s, 1H), 4.33(q, J=7.0Hz, 2H), 4.22(q, J=7.0Hz, 2H), 1.36(t, J=7.0Hz, 3H), 1.32(t, J=7.0Hz, 3H).

Step 2: Synthesis of 2-methyl(perfluoroethyl)pyrimidinol To a solution of 6.49 g of acetamidine hydrochloride in 75 ml of dimethyl sulfoxide, 23.3 g of a solution of about 20 weight% sodium ethoxide in ethanol, and 15.0 g of (Z)- ethyl 3-ethoxy-4,4,5,5,5-pentafluoropentenoate were successively added at 50 C.

After the addition, the reaction mixture was stiired at 50 C for 2 hours. After the stirring, .84 g of a solution of about 20 weight% sodium ethoxide in ethanol was added to the reaction mixture at 50 C. After the addition, the reaction mixture was stirred at 50 C for 2.5 hours. After the stirring, the reaction mixture was stirred at room temperature overnignt. After the reaction, the reaction mixture was mixed with 50 ml of water and extracted with diethyl ether (50 ml×2). The resulting aqueous layer was mixed with concentrated hydrochloric acid to adjust the aqueous layer to have a pH of from 1 to 2, and extracted with chloroform (20 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 7.0 g of the desired crude product as a white solid.

Melting point: 135-138 C H-NMR(CDCl3) : δ6.77(s, 1H), 2.57(s, 3H) (no peak of proton of OH was observed).

Step 3: Synthesis of 4-chloromethyl(perfluoroethyl)pyrimidine To a solution of 8.7 g of 2-methyl(perfluoroethyl)pyrimidinol in 20 ml of thionyl chloride, 30 mg of N,N-dimethylformamide was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for one hour. After the reaction, the reaction mixture was allowed to cool to room temperature, added dropwise to ice water and extracted with diethyl ether (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 9.33 g of the desired crude product as a reddish brown oil.

H-NMR(CDCl3) : δ7.54(s, 1H), 2.82(s, 3H).

Step 4: Synthesis of 2-methyl(perfluoroethyl)pyrimidinamine To a solution of 9.33 g of the crude 4-chloromethyl(perfluoroethyl)pyrimidine in 20 ml of acetonitrile, 20 ml of 28 weight% aqueous ammonia was added at room temperature. After the addition, the reaction mixture was stirred at room temperature for 3 days. After the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was mixed with 20 ml of water and extracted with ethyl acetate (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous salt soluton and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 6.75 g of the desired product as a reddish brown solid.

Melting point: 95-105 C H-NMR(CDCl ) : δ6.61(s, 1H), 5.12(brs, 2H), 2.59(s, 3H).

Reference Example 6: The following compound was synthesized in the same manner as in Steps 1 to 4 in Reference Example 5. 6-(Perfluoroethyl)pyrimidinamine H-NMR(CDCl ) : δ8.70(s, 1H), 6.79(s, 1H), 5.22(brs, 2H).

Reference Example 7: Synthesis of 4-chloro(perfluoroethyl)nicotinaldehyde Step 1: Synthesis of 4-chloro(perfluoroethyl)nicotinic acid Under a nitrogen atmosphere, to a solution of 4.04 g of 2,2,6,6- tetramethylpiperidine in 20 ml of tetrahydrofuran, 17.9 ml of a solution of about 1.6M n- butyllithium in n-hexane was added at -78 C. After the addition, the temperature of the reaction mixture was raised to 0 C, and the reaction mixture was stirred for 10 minutes.

After the stirring, the reaction mixture was cooled to -78 C, and a solution of 2.3 g of 6- (perfluoroethyl)nicotinic acid in 20 ml of tetrahydrofuran was added. After the addition, the temperature of the reaction mixture was raised to -40 C, and the reaction mixture was stirred for 1.5 hours. After the stirring, the reaction mixture was cooled to -78 C, and 4.5 g of hexachloroethane was added. After the addition, the reaction mixture was stirred at -78 C for 1.5 hours. After the reaction, 25 ml of a saturated ammonium chloride aqueous solution was added at -78 C. After the addition, the reaction mixture was warmed to room temperature, mixed with an about 1.0M sodium hydroxide aqueous solution to adjust to have a pH of 9, and washed with diethyl ether (20 ml).

The resulting aqueous layer was mixed with concentrated hydrochlorid acid to adjust the aqueous solution to have a pH of 2, and extracted with ethyl acetate (20 ml×2).

The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.08 g of the desired 4-chloro(perfluoroethyl)nicotinic acid as a brown oil.

H-NMR(CDCl ) : δ9.25(s, 1H), 7.84(s, 1H) (no peak of proton of CO H was observed).

Step 2: Synthesis of [4-chloro(perfluoroethyl)pyridinyl]methanol To a solution of 1.0 g of 4-chloro(perfluoroethyl)nicotinic acid in 10 ml of tetrahydrofuran, 8.5 ml of a solution of 0.85M borane-tetrahydrofuran complex in tetrahydrofuran was added at -50 C. After the addition, the reaction mixture was warmed to room temperature and stirred overnight. After the reaction, the reaction mixture was added dropwise to a 1M hydrochloric acid aqueous solution under cooling with ice and extracted with ethyl acetate (20 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 950 mg of the desired [4-chloro(perfluoroethyl)pyridinyl]methanol as an orange oil.

H-NMR(CDCl3) : δ8.87(s, 1H), 7.71(s, 1H), 4.92(s, 2H) (no peak of proton of OH was observed).

Step 3: Synthesis of 4-chloro(perfluoroethyl)nicotinaldehyde To a solution of 930 mg of [4-chloro(perfluoroethyl)pyridinyl]methanol in 10 ml of dichloromethane, 3 g of silicon dioxide and 1.53 g of pyridinium chlorochromate were successively added at room temperature. After the addition, the reaction mixture was stirred at room temperature for one hour. After the stirring, 500 mg of pyridinium chlorochromate was added to the reaction mixture. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the reaction, the reaction mixture was subjected to filtration through Celite, and the Celite was washed with 100 ml of n-hexane/ethyl acetate [2:1 (volume ratio)]. The resulting filtrate and washing solution were put together, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 30:70) as the eluent to obtain 154 mg of the desired product as a yellow oil.

H-NMR(CDCl ) : δ10.54(s, 1H), 9.14(s, 1H), 7.84(s, 1H).

Reference Example 8: The following compound was synthesized in the same manner as in Steps 1 to 3 in Reference Example 7. 4-Chloro(trifluoromethyl)nicotinaldehyde H-NMR(CDCl ) : δ10.54(s, 1H), 9.12(s, 1H), 7.81(s, 1H).

Reference Example 9: Synthesis of 3-nitro(trifluoromethyl)picolinaldehyde A solution of 930 mg of selenium dioxide and 1.46 g of 2-methylnitro (trifluoromethyl)pyridine in 10 ml of 1,4-dioxane was stirred under reflux with heating for 8 hours. After the stirring, the reaction mixture was subjected to filtration through Celite, and the Celite was washed with 10 ml of 1,4-dioxane. The resulting filtrate and washing solution were put together, and the solvent was evaporated under reduced pressure, and the resulting residue was mixed with 5 ml of saturated aqueous sodium bicarbonate and extracted with ethyl acetate (10 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 100:0 to 50:50) as the eluent. To the residue obtained by concentration, 10 ml of toluene was added, and the solvent was evaporated under reduced pressure. Then, 10 ml of toluene was added, and the solvent was evaporated under reduced pressure to obtain 1.07 g of the desired product as a brown liquid.

H-NMR(CDCl ) : δ10.32(s, 1H), 9.25-9.20(m, 1H), 8.53-8.49(m, 1H).

Reference Example 10: Synthesis of 3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinamine Step 1: Synthesis of tert-butyl [3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]carbamate To a solution of 3.0 g of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid in 30 ml of 2-methylpropanol, 3.14 g of triethylamine and 3.40 g of diphenylphosphoryl azide were added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 2 hours. After the reaction, the solvent was evaporated from the reaction mixture. The resulting residue was mixed with 20 ml of water and extracted with ethyl acetate (20 ml×2). The resulting organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (50:50) as the eluent to obtain 2.12 g of the desired product as a pale yellow solid.

H-NMR(CDCl ) : δ8.42(d, J=7.0Hz, 1H), 7.93-7.88(m, 1H), 7.13-7.01(m, 2H), 2.68(q, J=7.4Hz, 2H), 1.56(s, 9H), 1.21(t, J=7.4Hz, 3H).

Step 2: Synthesis of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinamine To a solution of 2.0 g of tert-butyl [3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinyl]carbamate in 10 ml of dichloromethane, 2.1 ml of trifluoroacetic acid was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the stirring, 10 ml of trifluoroacetic acid was added to the reaction mixture. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the reaction, the solvent was evaporated from the reaction mixture. The resulting resiude was mixed with 20 ml of water and extracted with chloroform (20 ml×2). The resulting organic layer was washed with a 1M sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.69 g of the desired product as a yellow oil.

H-NMR(CDCl3) : δ8.31(d, J=7.0Hz, 1H), 7.63-7.58(m, 1H), 6.98(dd, J=7.0, 1.6Hz, 1H), 4.41(brs, 2H), 2.63(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).

Reference Example 11: Synthesis of 3-(ethylthio)(trifluoromethyl)imidazo[1,2- a]pyridinecarboxamide To a solution of 1.34 g of 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridine carboxylic acid in 20 ml of dichloromethane, 882 mg of oxalyl chloride and 10 mg N,N- dimethylformamide were added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2.5 hours. After the stirring, the solvent was evaporated from the reaction mixture under reduced pressure to obtain crude 3- (ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid chloride. The obtained crude 3-(ethylthio)(trifluoromethyl)imidazo[1,2-a]pyridinecarboxylic acid chloride was dissolved in 2 ml of tetrahydrofuran and added to 20 ml of 28 weight% aqueous ammonia prepared in a separate container, under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the addition, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.8 g of the desired product as a pale yellow solid.

H-NMR(CDCl ) : δ8.90(s, 1H), 7.71(d, J=9.4Hz 1H), 7.47(dd, J=9.4, 2.0Hz, 1H), 7.38(brs, 1H), 5.66(brs, 1H), 3.03(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).

Reference Example 12: Synthesis of 2-bromo[3-methyl(trifluoromethyl)-3H- imidazo[4,5-b]pyridinyl]ethanone Step 1: Synthesis of (S)[3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridin yl]ethanol 37.7 g of N -methyl(trifluoromethyl)pyridine-2,3-diamine was dissolved in 150 ml of pyridine, and 32.8 g of (S)-(-)acetoxypropionyl chloride was added at -20 C.

After the addition, the reaction mixture was stirred at room temperature for 30 minutes.

After the stirring, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was dissolved in 150 ml of ethanol, and 39.4 ml of a 10M sodium hydroxide aqueous solution was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 2 hours. After the stirring, 20 ml of a 10M sodium hydroxide aqueous solution was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 4.5 hours. After the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was mixed with concentrated hydrochloric acid to adjust the aqueous solution to have a pH of 4, and extracted with ethyl acetate (100 ml×2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 59.8 g of the desired (S)[3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridinyl]ethanol as a black solid.

H-NMR(CDCl3) : δ8.65(s, 1H), 8.23(s, 1H), 5.20(brs, 1H), 3.97(s, 3H), 2.99(brs, 1H), 1.75(d, J=6.3Hz, 3H).

Step 2: Synthesis of 1-[3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridin yl]ethanone A solution of 48.3 g of (S)[3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl]ethanol in 200 ml of acetic acid was heated to 90 C, and a solution of 14.8 g of chromium(VI) oxide in 50 ml of water was added. After the addition, the reaction mixture was stirred under reflux with heating for 1.5 hours. After the stirring, a solution of 5 g of chromium(VI) oxide in 10 ml of water was added to the reaction mixture at 90 C. After the addition, the reaction mixture was stirred under reflux with heating for 1.5 hours. After the reaction, the reaction mixture was added dropwise to 800 ml of water at room temperature. The precipitated solid was collected by filtration. The resulting solid was washed with water to obtain 35.6 g of the desired 1-[3-methyl (trifluoromethyl)-3H-imidazo[4,5-b]pyridinyl]ethanone as a brown solid.

Melting point: 106-108 C H-NMR(CDCl ) : δ8.82(d, J=1.5Hz, 1H), 8.43(d, J=1.5Hz, 1H), 4.23(s, 3H), 2.86(s, 3H).

Step 3: Synthesis of 2-bromo[3-methyl(trifluoromethyl)-3H-imidazo[4,5- b]pyridinyl]ethanone .6 g of 1-[3-methyl(trifluoromethyl)-3H-imidazo[4,5-b]pyridinyl]ethanone was dissolved in 300 ml of toluene and a solution of about 5.1M hydrogen bromide in 150 ml of acetic acid, and 25.8 g of bromine was added under cooling with ice. After the addition, the reaction mixture was stirred at room temperature for 2 hours. After the stirring, 3.12 g of bromine was added to the reaction mixture at room temperature.

After the addition, the reaction mixture was stirred at room temperature for one hour.

After the stirring, 2.58 g of bromine was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred at room temperature for 30 minutes. After the reaction, the reaction mixture was mixed with a 10M sodium hydroxide aqueous solution to have a pH of 3, and extracted with toluene (200 ml×2).

The resulting organic layer was washed with a saturated sodium hydrogen sulfite aqueous solution, dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The precipitated solid was collected by filtration. The resulting solid was washed with diisopropyl ether to obtain 36.6 g of the desired 2-bromo[3-methyl(trifluoromethyl)- 3H-imidazo[4,5-b]pyridinyl]ethanone as a white solid.

Melting point: 90-91 C H-NMR(CDCl ) : δ8.86(d, J=1.8Hz, 1H), 8.47(d, J=1.8Hz, 1H), 4.85(s, 2H), 4.26(s, 3H).

Reference Example 13: Synthesis of 2-bromo[3-methyl(trifluoromethyl)-3H- imidazo[4,5-c]pyridinyl]ethanone Step 1: Synthesis of (S)[3-methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridin yl]ethanol 3.34 g of N -methyl(trifluoromethyl)pyridine-3,4-diamine was dissolved in 20 ml of pyridine, and 2.89 g of (S)-(-)acetoxypropionyl chloride was added at -20 C. After the addition, the reaction mixture was stirred at room temperature for 20 minutes. After the stirring, the solvent was evaporated from the reaction mixture under reduced pressure. The resulting residue was dissolved in 20 ml of ethanol, and 3.5 ml of a 10M sodium hydroxide aqueous solution was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for one hour. After the stirring, 1.8 ml of a 10M sodium hydroxide aquous solution was added to the reaction mixture at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 2 hours. After the reaction, the reaction mixture was mixed with 50 ml of water and extracted with ethyl acetate (50 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of 100:0 to 50:50) as the eluent to obtain 3.0 g of the desired product as a pale pink solid.

Melting point: 97-100 C H-NMR(CDCl ) : δ8.84(s, 1H), 8.04(d, J=0.7Hz, 1H), 5.31-5.14(m, 1H), 4.02(s, 3H), 3.03(d, J=7.2Hz, 1H), 1.78(d, J=6.5Hz, 3H).

Step 2: Synthesis of 1-[3-methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridin yl]ethanone A solution of 3.0 g of (S)[3-methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridin- 2-yl]ethanol in 30 ml of acetic acid was heated to 90 C, and a solution of 1.22 g of chromium(VI) oxide in 10 ml of water was added. After the addition, the reaction mixture was stirred under reflux with heating for one hour. After the reaction, the reaction mixture was mixed with 50 ml of water and extracted with ethyl acetate (50 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.59 g of the desired 1-[3- methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridinyl]ethanone as a pale yellow solid.

Melting point: 136-140 C H-NMR(CDCl3) : δ9.03(s, 1H), 8.19(d, J=0.9Hz, 1H), 4.28(s, 3H), 2.89(s, 3H).

Step 3: Synthesis of 2-bromo[3-methyl(trifluoromethyl)-3H-imidazo[4,5- c]pyridinyl]ethanone To a solution of 2.55 g of 1-[3-methyl(trifluoromethyl)-3H-imidazo[4,5-c]pyridin- 2-yl]ethanone in 30 ml of dichloromethane, 1.16 g of triethylamine was added at room temperature. After the addition, 2.44 g of trimethylsilyl trifluoromethanesulfonate was added to the reaction mixture under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for 30 minutes. After the stirring, 3.95 g of trimethylphenylammonium tribromide was added to the reaction mixture under cooling with ice. After the addition, the reaction mixture was stirred under cooling with ice for minutes. After the reaction, the reaction mixture was mixed with 50 ml of water and extracted with chloroform (30 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.

The precipitated solid was collected by filtration. The resulting solid was washed with n-hexane to obtain 2.66 g of the desired 2-bromo[3-methyl(trifluoromethyl)-3H- imidazo[4,5-c]pyridinyl]ethanone as a white solid.

Melting point: 127-131 C H-NMR(CDCl3) : δ9.07(s, 1H), 8.21(d, J=1.0Hz, 1H), 4.87(s, 2H), 4.31(s, 3H).

The compounds of the present invention may be synthesized in accordance with the above Processes and Synthetic Examples. Examples of condensed heterocyclic compounds produced in the same manner as in Synthetic Examples 1 to 30 are shown in Tables 6 to 24, and examples of intermediates thereof are shown in Tables 25 to 32, however, the condensed heterocyclic compounds of the present invention and the intermediates thereof are not limited thereto.

In Tables, "Me" represents a methyl group, "Et" an ethyl group, and "Ph" a phenyl group. Substituents represented by Z1 to Z16 in Tables have the following structures.

Further, in Tables, "*1" represents that the compound is a solid, "*2" represents that the compound is an oil, "*5" represents that the compound was decomposed when its melting point was measured, and "m.p." represents the melting point (unit: C). Further, with respect to the description of the melting point in Tables, ">" represents that the melting point of the compound is higher than the described temperature, for example, ">250" means that the compound did not melt at 250 C.

Table 6 Table 6 (Continued) Table 6 (Continued) Table 6 (Continued) Table 6 (Continued) Table 7 Table 8 Table 9 Table 10 Table 11 Table 12 Table 13 Table 14 Table 15 Table 16 Table 17 Table 18 Table 19 Table 20 Table 21 Table 22 Table 23 Table 24 Table 25 Table 26 Table 27 Table 28 Table 29 Table 30 Table 31 Table 32 H-NMR data of the compounds of the present disclosure and intermediates thereof are shown in Table 33. The proton nuclear magnetic resonance chemical shift values were measured by using Me Si (tetramethylsilane) as a standard substance in deuterated chloroform solvent at 300 MHz (ECX300 or ECP300, manufactured by JEOL Ltd.).

Reference symbols in the proton nuclear magnetic resonance chemical shift values have the following meanings. s: Singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet.

Table 33 Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Table 33 (Continued) Now, usefulness of the compounds of the present invention as pesticides will be described in detail by referring to the following Test Examples, but the present invention is by no means restricted thereto.

TEST EXAMPLE 1: Insecticidal Test on Nilaparvata lugens 10% emulsifiable concentrates (or 10% wettable powders) of compounds of the present disclosure were diluted with water containing a spreader to obtain 500 ppm solutions. Rice sheaths were soaked in the solutions for about 10 seconds. After the soaking, the rice sheaths were dried in air and put in test tubes. In each tube, five 3rd- instar larvae of Nilaparvata lugens were released, and the tubes were capped with sponge and placed in an incubator at 25 C. 6 Days after, dead insects in the test tubes were counted, and the mortality (%) (the number of dead insects ÷ the number of released insects × 100) was calculated. The test was carried out in duplicate.

Among the compounds tested, the following compounds showed a mortality of at least 90%.

Compounds Nos. 1001a, 1002a, 1005a, 1006a, 1009a, 1015a, 1 020a, 1023a, 1024a, 1035a, 1036a, 1038a, 1039a, 1040a, 1042a, 1043a, 1044a, 1049a, 1052a, 1057a, 1057c, 1058a, 1064a, 1 072a, 1074a, 1095a, 1096a, 1097a, 1099a, 1100a, 1105a, 1106a, 1116a, 1117a, 1122a, 1123a, 1001a, 1002a, 1001a, 1003a, 1 005a, 1007a, 1002a, 1002a, 1002a, 1005a, 1010a, 1002a, 1 001a, 1001b, 1002a, 1003a, 1004a, 1004b, 1003a, 1004a, 1006a, 1007a, 1008a, 1009a, 1001a, 1001a, 1001b, 2 001a and 3002a of the present disclosure.

TEST EXAMPLE 2: Insecticidal Test on Plutella xylostella 10% emulsifiable concentrates (or 10% wettable powders) of compounds of the present disclosure were diluted with water containing a spreader to obtain 500 ppm solutions. Leaves of cabbage were soaked in the solutions for about 10 seconds.

After the soaking, the leaves were dried in air and placed in dishes. In each dish, five 3rd-instar larvae of Plutella xylostella were released, and the dishes were covered with lids and placed in an incubator at 25°C. 6 Days after, dead insects in the dishes were counted, and the mortality was calculated by using the same equation as in Test Example 1. The test was carried out in duplicate.

Compounds Nos. 1001a, 1001b, 1001c, 1002a, 1002b, 1003a, 1 003c, 1004a, 1005a, 1005c, 1006a, 1007a, 1008a, 1009a, 1011a, 1012a, 1012b, 1013a, 1013b, 1013c, 1014a, 1014b, 1014c, 1 015a, 1015b, 1016a, 1016b, 1016c, 1017a, 1018a, 1019a, 1020a, 1020b, 1021b, 1022a, 1023a, 1023b, 1023c, 1024a, 1026a, 1 027a, 1027b, 1029a, 1030a, 1030b, 1030c, 1032a, 1033a, 1034a, 1035a, 1036a, 1037a, 1038a, 1039a, 1040a, 1040c, 1041a, 1 042a, 1043a, 1044a, 1045a, 1045b, 1046a, 1047a, 1048a, 1049a, 1049b, 1050a, 1050b, 1051a, 1051b, 1052a, 1052b, 1053a, 1 054a, 1055a, 1056a, 1057a, 1057c, 1058a, 1058b, 1059a, 1060a, 1060b, 1061a, 1062a, 1063a, 1063b, 1064a, 1065a, 1066a, 1 067a, 1068a, 1069a, 1069b, 1070a, 1070b, 1071a, 1072a, 1072b, 1072c, 1073b, 1074a, 1076a, 1077a, 1077b, 1080a, 1081a, 1 082a, 1083a, 1084a, 1085a, 1086a, 1087a, 1088a, 1089a, 1090a, 1091a, 1092a, 1093a, 1093b, 1094a, 1094b, 1094c, 1095a, 1 096a, 1097a, 1099a, 1100a, 1101a, 1101b, 1103a, 1103b, 1104a, 1105a, 1105b, 1105c, 1106a, 1106b, 1106c, 1107a, 1108a, 1 109a, 1109b, 1110a, 1110c, 1111a, 1112a, 1112b, 1113a, 1113b, 1114a, 1114b, 1115a, 1115b, 1116a, 1117a, 1118a, 1118c, 1 120c, 1121a, 1122a, 1123a, 1001a, 1002a, 1004a, 1004b, 1004c, 1005a, 1006a, 1001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1 007a, 1008a, 1009a, 1010a, 1011a, 1012a, 1013a, 1014a, 1001a, 1002a, 1003a, 1003b, 1001a, 1002a, 1003a, 1004a, 1001a, 1 002a, 1001a, 1001b, 1002a, 1002b, 1003a, 1003b, 1004b, 1005a, 1005b, 1006a, 1006b, 1007a, 1008a, 1009a, 1010a, 1011a, 1 013a, 1013b, 1014a, 1014b, 1015a, 1015b, 1002a, 1002b, 1003a, 1003b, 1001a, 1001b, 1001c, 1002a, 1002b, 1002c, 1 003a, 1001a, 1001b, 1001c, 1002a, 1003a, 1003b, 1004a, 1- 11-004b, 1004c, 1005a, 1005b, 1006a, 1006b, 1007a, 1007b, 1007c, 1001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1 007a, 1008a, 1009a, 1001a, 1001a, 1002a, 1003a, 1001a, 1001b, 2001a, 2001b, 2002a, 3001a, 3001b, 3001c, 3002a, 3 002b and 3002c of the present disclosure.

TEST EXAMPLE 3: Insecticidal Test on Spodoptera litura 10% emulsifiable concentrates (or 10% wettable powders) of compounds of the present disclosure were diluted with water containing a spreader to obtain 500 ppm solutions. Leaves of cabbage were soaked in the solutions for about 10 seconds.

After the soaking, the leaves were dried in air and placed in dishes. In each dish, five 3rd-instar larvae of Spodoptera litura were released, and the dishes were covered with lids and placed in an incubator at 25°C. 6 Days after, dead insects in the dishes were counted, and the mortality was calculated by using the same equation as in Test Example 1. The test was carried out in duplicate.

Compounds Nos. 1001a, 1001b, 1001c, 1002a, 1002b, 1003a, 1 004a, 1005a, 1005c, 1006a, 1007a, 1009a, 1011a, 1012a, 1013a, 1013b, 1013c, 1014a, 1014c, 1015a, 1015b, 1016a, 1016b, 1 016c, 1017a, 1018a, 1019a, 1020a, 1020b, 1023a, 1023b, 1023c, 1024a, 1026a, 1027a, 1027b, 1029a, 1030a, 1030b, 1030c, 1 032a, 1033a, 1034a, 1036a, 1037a, 1038a, 1039a, 1040a, 1040c, 1041a, 1042a, 1043a, 1044a, 1045a, 1045b, 1046a, 1047a, 1 048a, 1049a, 1049b, 1050a, 1051a, 1051b, 1052a, 1053a, 1056a, 1057a, 1057c, 1058a, 1059a, 1060a, 1061a, 1062a, 1063a, 1 064a, 1065a, 1066a, 1067a, 1068a, 1069a, 1070a, 1070b, 1071a, 1072a, 1072b, 1072c, 1074a, 1076a, 1077a, 1077b, 1080a, 1 081a, 1082a, 1083a, 1084a, 1085a, 1087a, 1089a, 1090a, 1091a, 1092a, 1093a, 1093b, 1094a, 1094b, 1094c, 1095a, 1096a, 1 097a, 1099a, 1100a, 1101a, 1103a, 1103b, 1104a, 1105a, 1105b, 1106a, 1109a, 1110a, 1110c, 1111a, 1112a, 1113a, 1114a, 1 114b, 1115a, 1115b, 1118a, 1122a, 1123a, 1001a, 1002a, 1004a, 1004b, 1004c, 1005a, 1006a, 1001a, 1002a, 1003a, 1004a, 1 005a, 1006a, 1007a, 1008a, 1009a, 1010a, 1011a, 1012a, 1013a, 1014a, 1001a, 1002a, 1003a, 1003b, 1001a, 1002a, 1003a, 1 004a, 1001a, 1002a, 1001a, 1002a, 1002b, 1003a, 1003b, 1005a, 1005b, 1006a, 1006b, 1007a, 1008a, 1009a, 1010a, 1011a, 1 013a, 1013b, 1014a, 1015a, 1002a, 1002b, 1003a, 1001a, 1 001b, 1001c, 1002a, 1002b, 1002c, 1003a, 1001a, 1001b, 1001c, 1002a, 1003a, 1004a, 1004b, 1004c, 1005a, 1 005b, 1006a, 1007a, 1007b, 1007c, 1001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1007a, 1008a, 1009a, 1001a, 1 001a, 1003a, 1001a, 2001a, 2001b, 3001a, 3001c, 3002a, 3 002b and 3002c of the present disclosure.

TEST EXAMPLE 4: Insecticidal Activity on Frankliniella occidentalis In styrol cups having an inner diameter of 7 cm, wet filter paper was laid, kidney bean leaves cut into a 3 cm square were laid on the paper, and each leaf was inoculated with 20 larvae of Frankliniella occidentalis. 10% emulsifiable concentrates (or 10% wettable powders) of compounds of the present disclosure were diluted with water containing a spreader to obtain 500 ppm solutions. 2.5 ml of the solutions were sprayed from a rotary spray tower into the styrol cups (2.5 mg/cm ). 2 Days after, dead insects were counted, and insect damage on kidney bean leaves was examined. The mortality was calculated by using the same equation as in Test Example 1.

The insect damage degree was evaluated as follows. 1: 0 to 20% insect damage, 2: 20 to 50% insect damage, 3: 50 to 70% insect damage, and 4: 70% or higher insect damge. The test was carried out in duplicate.

Among the compounds tested, the following compounds showed a mortality of at least 50% and an insect damage degree of 2 or higher.

Compounds Nos. 1001a, 1002b, 1003a, 1005a, 1006a, 1023c, 1 035a, 1036a, 1038a, 1039a, 1042a, 1043a, 1049a, 1050a, 1051a, 1052a, 1052b, 1053a, 1054b, 1055b, 1056a, 1057a, 1057c, 1 061a, 1062a, 1063a, 1064a, 1067a, 1068a, 1069b, 1070a, 1071a, 1072a, 1074a, 1076a, 1080a, 1081a, 1082a, 1087a, 1089a, 1 090a, 1093a, 1095a, 1096a, 1097a, 1099a, 1105a, 1106b, 1109a, 1110a, 1112a, 1114a, 1115a, 1117a, 1120c, 1122a, 1123a, 1 006a, 1012a, 1003a, 1007a, 1008a, 1011a, 1013a, 1014a, 1015a, 1002a, 1003a, 1003a, 1003a, 1004a, 1006a, 1007a, 1007c, 1009a, 2002a, 3001a, 3001b, 3001c and 3002a of the present disclosure.

TEST EXAMPLE 5: Insecticidal Test on Myzus persicae Wet absorbent cotton was laid on glass dishes having an inner diameter of 3 cm, and covered with leaves of cabbage cut into circles of the same diameter, and 4 apterous adults of Myzus persicae were released. After a day, 10% emulsifiable concentrates (or 10%wettable powders) of compounds of the present disclosure were diluted with water containing a spreader to obtain 500 ppm solutions. The solutions were sprayed from a rotary spray tower (2.5 mg/cm ), and the dishes were covered with lids and placed in an incubator at 25 C. 6 Days after, dead insects were counted, and the mortality was calculated by using the same equation as in Test Example 1. The test was carried out in duplicate.

Compounds Nos. 1001a, 1002a, 1002b, 1003a, 1004a, 1004b, 1 004c, 1005a, 1006a, 1007a, 1009a, 1011a, 1012a, 1012b, 1013a, 1013c, 1014a, 1014c, 1015a, 1015b, 1016c, 1017a, 1018a, 1 019a, 1020a, 1023a, 1024a, 1025c, 1026a, 1027a, 1032a, 1033a, 1034a, 1035a, 1036a, 1037a, 1038a, 1039a, 1040b, 1040c, 1 041a, 1042a, 1043a, 1044a, 1045b, 1046a, 1047a, 1048a, 1049a, 1049b, 1050a, 1051a, 1052a, 1053a, 1056a, 1057a, 1057c, 1 058a, 1059a, 1060a, 1061a, 1062a, 1063a, 1064a, 1065a, 1066a, 1067a, 1068a, 1071a, 1072a, 1073b, 1074a, 1077a, 1077b, 1 080a, 1082a, 1086a, 1087a, 1090a, 1091a, 1093a, 1093b, 1095a, 1096a, 1097a, 1099a, 1100a, 1101a, 1102a, 1105a, 1106a, 1 106b, 1106c, 1107a, 1108a, 1109a, 1110a, 1112a, 1113a, 1115a, 1116a, 1117a, 1118a, 1120c, 1121a, 1122a, 1123a, 1001a, 1 002a, 1001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1007a, 1009a, 1010a, 1011a, 1012a, 1001a, 1002a, 1003a, 1001a, 1002a, 1 003a, 1004a, 1001a, 1002a, 1002a, 1002b, 1003a, 1003b, 1004b, 1005a, 1006a, 1008a, 1010a, 1013a, 1014a, 1015b, 1002a, 1 003a, 1001a, 1001b, 1002a, 1002b, 1002c, 1003a, 1001a, 1001b, 1002a, 1003a, 1004a, 1007a, 1007b, 1007c, 1 001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1007a, 1008a, 1001a, 1003a, 1001a, 1001a, 2001a, 2002a, 3001a, 3001c and 3002a of the present disclosure.

TEST EXAMPLE 6: Insecticidal Test on Bemisia argentifolii In styrol cups having an inner diameter of 7 cm, wet filter paper was laid, and kidney bean leaves cut to 3 cm were laid on the paper. 10% emulsifiable concentrates (or 10% wettable powders) of compounds of the present disclosure were diluted with water containing a spreader to obtain 500 ppm solutions, and 2.5 ml of the solutions were sprayed from a rotary spray tower into the styrol cups (2.5 mg/cm ). The leaves were dried in air, and adults of Bemisia argentifolii were released in the cups, and the cups were covered with lids and placed in an incubator at 25 C. 5 Days after, dead insects were counted, and the mortality was calculated by using the same equation as in Test Example 1. The test was carried out in duplicate.

Compounds Nos. 1035a, 1036a, 1043a, 1049a, 1047a, 1094a, 1 095a, 1096a, 1099a, 1001a, 1001a and 3002a of the present disclosure.

TEST EXAMPLE 7: Soil Irrigation Test on Myzus persicae % emulsifiable concentrates of compounds of the present disclosure were diluted with tap water to obtain 500 ppm solutions.

The soil around the bases of cabbage seedlings (at the 2.5-leaf stage) planted in plastic cups was irrigated with 10 ml of the solutions. After the irrigation, the cabbage seedlings were placed in a greenhouse. One day after the irrigation, adults of Myzus persicae were released at a ratio of 20 insects per seedling, and the seedlings were left in the greenhouse. 6 Days after the release of the insects, living insects were counted, and the control value was calculated from the following equation.

Control value (%) = {1-(Cb×Tai)/(Cai×Tb)}×100 Cb: the number of insects in a non-treated plot before treatment Cai: the final number of living insects in a non-treated plot Tb: the number of insects in a treated plot before treatment Tai: the final number of living insects in a treated plot Among the compounds tested, the following compounds showed a control value of at least 90%.

Compounds Nos. 1001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1 012a, 1013a, 1014a, 1016a, 1017a, 1018a, 1029a, 1032a, 1035a, 1039a, 1042a, 1043a, 1049a, 1057a, 1058a, 1060a, 1074a, 1 093a, 1097a, 1106a, 1112a, 1113a, 1122a, 1002a, 1003a, 1005a, 1006a, 1010a, 1013a, 1002a, 1008a, 1001a, 1001a and 2 002a of the present disclosure.

TEST EXAMPLE 8: Systemic Insecticidal Test on Nilaparvata lugens % emulsifiable concentrates of compounds of the present disclosurewere diluted with tap water to obtain 20 ppm solutions, and root of rice plug seedlings (at the 2-leaf stage) were dipped in the solutions. 7 Days after, the rice seedlings were picked and put in test tubes, and in each tube, five 3rd-instar larvae of Nilaparvata lugens were released, and the tubes were capped with sponge and placed in an incubator at 25°C. 6 Days after the release of the insects, dead insects were counted, and the mortality (%) (the number of dead insects ÷ the number of released insects × 100) was calculated. The test was carried out in duplicate.

Compounds Nos. 1001a, 1001b, 1002a, 1005a, 1006a, 1013a, 1 014a, 1017a, 1018a, 1020a, 1030a, 1032a, 1035a, 1036a, 1038a, 1039a, 1042a, 1043a, 1044a, 1049a, 1052a, 1057a, 1057c, 1 058a, 1067a, 1070a, 1072a, 1074a, 1076a, 1077a, 1092a, 1093a, 1095a, 1096a, 1097a, 1099a, 1105a, 1106a, 1107a, 1109a, 1 111a, 1113a, 1117a, 1122a, 1002a, 1001a, 1005a, 1007a, 1002a, 1005a, 1006a, 1008a, 1010a, 1013a, 1002a, 1001a, 1002a, 1- 11-003a, 1004a, 1007a, 1006a, 1008a, 1009a, 1001a, 1 001a, 2002a and 3002b of the present disclosure.

TEST EXAMPLE 9: Soil Irrigation Test on Plutella xylostella % emulsifiable concentrates of compounds of the present disclosurewere diluted with tap water to obtain 500 ppm solutions.

The soil around the bases of cabbage seedlings (at the 2.5-leaf stage) planted in plastic cups was irrigated with 10 ml of the solutions. After the irrigation, the cabbage seedlings were placed in a greenhouse. 5 Days after the irrigation, leaves of cabbage were picked and placed in dishes. In each dish, five 3rd-instar larvae of Plutella xylostella were released, and the dishes were covered with lids and placed in an incubator at 25°C. 6 Days after, dead insects in the dishes were counted, and the mortality was calculated by using the same equation as in Test Example 1. The test was carried out in duplicate.

Among the compounds tested, the following compounds showed a control value of at least 90%.

Compounds Nos. 1001a, 1001c, 1002a, 1003a, 1004a, 1005a, 1 006a, 1013a, 1014a, 1015a, 1016a, 1018a, 1029a, 1030a, 1039a, 1042a, 1043a, 1049a, 1050a, 1052a, 1056a, 1057a, 1058a, 1 059a, 1060a, 1063a, 1069a, 1070a, 1074a, 1076a, 1077a, 1080a, 1082a, 1090a, 1093a, 1096a, 1097a, 1099a, 1103a, 1103b, 1 105a, 1106a, 1107a, 1109a, 1111a, 1112a, 1113a, 1117a, 1122a, 1001a, 1004a, 1013a, 1014a, 1001a, 1002a, 1003a, 1005a, 1 006a, 1007a, 1008a, 1010a, 1013a, 1002a, 1002a, 1001a, 1 002a, 1003a, 1004a, 1007a, 1008a, 1009a, 1001a, 1001a and 2002a of the present disclosure.

TEST EXAMPLE 10: Test on the effect of seed treatment on Aphis glycines 2.4 mg of compounds of the present disclosurewere diluted with 97.6 μl of acetone. Four soybean seeds were put in each 50 ml plastic tube, and the solutions of compounds of the present disclosurewere poured onto the seeds and stirred until the acetone evaporated completely so that the seeds were evenly coated with the compounds. The treated seeds were sown in pots, 4 seeds per pot, and placed in a greenhouse. After the primary leaf folded out, two adults of Aphis glycines were released per seedling. 7 Days after the release of the insects, living insects were counted, and the control value was calculated from the following equation.

Control value (%)={1-(Cb×Tai)/(Cai×Tb)}×100 wherein Cb: the number of insects in a non-treated plot before treatment Cai: the final number of living insects in a non-treated plot Tb: the number of insects in a treated plot before treatment Tai: the final number of living insects in a treated plot Among the compounds tested, the following compounds showed a control value of at least 90%.

Compounds Nos. 1001a, 1002a, 1003a, 1004a, 1005a, 1006a, 1 012a, 1013a, 1014a, 1016a, 1017a, 1018a, 1029a, 1032a, 1035a, 1039a, 1042a, 1043a, 1049a, 1057a, 1058a, 1060a, 1074a, 1 093a, 1097a, 1106a, 1112a, 1113a, 1122a, 1001a, 1002a, 1003a, 1005a, 1006a, 1010a, 1013a, 1002a, 1008a, 1001a and 1 001a of the present disclosure.

TEST EXAMPLE 11: Test on the effect on Rhipicephalus sanguineus 3.5 mg of compounds of the present disclosurewere diluted with 3.5 ml of acetone to obtain 1,000 ppm solutions. 350 μl of the solutions were applied to the bottoms and the side walls of glass containers with an inner wall surface area of 35 cm , and acetone was volatilized to prepare thin films of the compounds on the inner walls of the glass containers. Since the inner wall surface area of each glass container was 35 cm , the application dose was 10 μg/cm .

To each glass container, five protonymphs (male and female) of Rhipicephalus sanguineus were released, and the containers were covered with lids and placed in an incubator at 25 C. 4 Days after the release of the ticks, dead ticks were counted, and the mortality was calculated by using the same equation as in Test Example 1.

Among the compounds tested, the following compounds showed a mortality of at least 50%.

Compounds Nos. 1001a, 1001b, 1002a, 1003a, 1003b, 1003c, 1 004a, 1004b, 1004c, 1005a, 1005b, 1006a, 1006b, 1010a, 1011a, 1012a, 1013a, 1014a, 1014b, 1016a, 1016c, 1017a, 1018a, 1 020a, 1022a, 1023c, 1026a, 1023c, 1027b, 1035a, 1039a, 1040a, 1042a, 1043a, 1045a, 1046a, 1047a, 1049a, 1051a, 1052b, 1 053a, 1055a, 1057a, 1057c, 1059b, 1060a, 1062a, 1063a, 1065a, 1067a, 1068a, 1071a, 1072a, 1072b, 1075a, 1080a, 1083a, 1 088a, 1093a, 1093b, 1094a, 1094b, 1095a, 1096a, 1099a, 1103a, 1105a, 1105b, 1105c, 1106a, 1106b, 1106c, 1107a, 1108a, 1 109a, 1110a, 1110c, 1111a, 1111b, 1112a, 1113a, 1114a, 1114b, 1115a, 1115b, 1116a, 1118b, 1118c, 1120c, 1004a, 1005a, 1 011a, 1013a, 1014a, 1001a, 1001a, 1002a, 1005a, 1006a, 1006b, 1008a, 1010a, 1011a, 1013a, 1014a, 1014b, 1015b, 1002a, 1 002b, 1003a, 1002c, 1004a, 1004c, 1005a, 1006a, 1007c, 1- 12-004a, 1007a, 1003a, 1001a, 3002a, 3002b and 3002c of the present disclosure.

TEST EXAMPLE 12: Test on the effect on Ctenocephalides felis 3.5 mg of compounds of the present disclosurewere diluted with 3.5 ml of acetone to obtain 1,000 ppm solutions. 350 μl of the solutions were applied to the bottoms and the side walls of glass containers with an inner wall surface area of 35 cm , and acetone was volatilized to prepare thin films of the compounds on the inner walls of the glass containers. Since the inner wall surface area of each glass container was 35 cm , the application dose was 10 μg/cm .

To each glass container, five adults (male and female) of Ctenocephalides felis were released, and the containers were covered with lids and placed in an incubator at C. 4 Days after the release of the fleas, dead fleas were counted, and the mortality was calculated by using the same equation as in Test Example 1.

Compounds Nos. 1001a, 1001b, 1001c, 1002a, 1002b, 1003a, 1 003b, 1003c, 1004a, 1004b, 1004c, 1005a, 1005b, 1005c, 1006a, 1007a, 1009a, 1012a, 1013a, 1013b, 1013c, 1014a, 1014c, 1 015a, 1015b, 1016a, 1016b, 1016c, 1017a, 1018a, 1019a, 1020a, 1023a, 1023b, 1023c, 1024a, 1025c, 1026a, 1027a, 1027b, 1 029a, 1030a, 1032a, 1033a, 1034a, 1035a, 1036a, 1037a, 1039a, 1040c, 1041a, 1042a, 1043a, 1044a, 1045a, 1046a, 1047a, 1 047b, 1048a, 1048b, 1049a, 1050a, 1050b, 1051a, 1051b, 1052a, 1052b, 1053a, 1054b, 1055a, 1056a, 1057a, 1057c, 1058a, 1 058b, 1059b, 1060a, 1060b, 1061a, 1062a, 1062b, 1063a, 1063b, 1064a, 1065a, 1066a, 1066b, 1067a, 1067b, 1068a, 1069a, 1 070a, 1071a, 1072a, 1072b, 1072c, 1073b, 1074a, 1074b, 1075a, 1076a, 1077a, 1077b, 1080a, 1081a, 1082a, 1084a, 1085a, 1 086a, 1087a, 1088a, 1089a, 1090a, 1091a, 1092a, 1093a, 1093b, 1094a, 1094b, 1094c, 1095a, 1096a, 1097a, 1099a, 1101a, 1 102a, 1103a, 1103b, 1104a, 1105a, 1105b, 1105c, 1106a, 1106b, 1106c, 1107a, 1108a, 1109a, 1110a, 1110c, 1111a, 1111b, 1 112a, 1113a, 1114a, 1114b, 1115a, 1115b, 1116a, 1117a, 1118a, 1118b, 1119c, 1122a, 1123a, 1001a, 1001a, 1002a, 1003a, 1 004a, 1005a, 1006a, 1007a, 1008a, 1009a, 1010a, 1011a, 1012a, 1013a, 1014a, 1001a, 1002a, 1003a, 1003b, 1001a, 1002a, 1 003a, 1004a, 1002a, 1002b, 1003a, 1004b, 1005a, 1006a, 1006b, 1007a, 1007b, 1008a, 1009a, 1010a, 1011a, 1013a, 1013c, 1 014a, 1014b, 1002a, 1002b, 1003a, 1003b, 1001b, 1002a, 1 002b, 1002c, 1003a, 1001a, 1001b, 1001c, 1003a, 1004a, 1004c, 1005b, 1006a, 1007b, 1007c, 1001a, 1002a, 1 003a, 1006a, 1007a, 1008a, 1009a, 1001a, 1003a, 1001a, 1001b, 1001a, 2001a, 3001a, 3001b, 3001c, 3002a, 3002b and 3002c of the present disclosure.

TEST EXAMPLE 13: Test on the parasiticidal effect by rat oral administration on Rhipicephalus sanguineus mg of compounds of the present disclosurewere dissolved in 5 ml of olive oil to prepare administration solutions. The solutions were orally administered to rats in a dose of 10 ml/kg body weight by a feeding tube. The oral administration was repeated twice in each group. 1 Hour after the administration, 50 protonymphs (male and female) of Rhipicephalus sanguineus were released for each rat. 3 Days after the release of the ticks, the number of ticks parasitic on the rats were counted, and the parasiticidal degree was calculated from the following equation.

Parasiticidal degree (%) = 100×(1 - the number of parasitic ticks on administered group/the number of parasitic ticks on non-administered group) Among the compounds tested, the following compounds showed a parasiticidal deree of at least 70%.

Compounds Nos. 1001a, 1002a, 1003a, 1006a, 1016a, 1096a, 1 103a, 1011a and 1002a of the present disclosure.

INDUSTRIAL APPLICABILITY The compounds of the present invention are very useful compounds which are excellent in pesticidal activities and have little harmful effect on non-target organisms such as mammals, fishes and beneficial insects.

The entire disclosures of Japanese Patent Application No. 2015-025604 filed on February 12, 2015 and Japanese Patent Application No. 2015-133816 filed on July 2, 2015 including specifications, claims and summaries are incorporated herein by reference in their entireties.

Claims

1. A condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: 5 wherein D substituted with -S(O)nR is a ring represented by D1: Q is a ring represented by Q1 : 10 G is C(Y1), G2 is C(Y2), G is C(Y3), G is C(Y4), 1 1a A is N(A ), 15 A is C(R ), A is C(R ), A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), R is C -C alkyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 5 haloalkylsulfonyl, R is C1-C8 alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C ) alkylthio optionally substituted with R , C -C haloalkylsulfinyl or C -C 6 1 6 1 6 haloalkylsulfonyl, 10 R is C1-C8 alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, A is a hydrogen atom or C -C alkyl, each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1- C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally 15 substituted with Y , C -C alkoxy, C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, 1 8 1 8 1 6 1 6 (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C 1 6 1 6 1 6 90a 90b haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -C(O)R , -C(O)NHR , - 90c 90b 90e 90f 90g C(O)N(R )R , -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , - 90h 90g 90i 90j 90k 90j N(R )R , mercapto, -SC(O)R , -S(O) NHR , -S(O) N(R )R , -SF , cyano, nitro, 2 2 5 20 phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , Y is C1-C8 alkoxycarbonyl Y is C -C alkyl, C -C cycloalkyl, trimethylsilyl or phenyl, 1 6 3 6 Y is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, 25 cyano or nitro, R is a hydrogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy or C -C 1 6 1 6 1 8 1 8 haloalkoxy, 90b 90c 90i 90j 90k each of R , R , R , R and R is independently C1-C6 alkyl or C1-C6 haloalkyl, 30 R is a hydrogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C 1 6 1 6 1 8 1 8 haloalkoxy, C -C alkylamino, C -C haloalkylamino, di(C -C ) alkylamino or di(C -C ) 1 6 1 6 1 6 1 6 haloalkylamino, R is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1- C ) alkylamino or di(C -C ) haloalkylamino, 6 1 6 90g 90h 5 each of R and R is independently C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 haloalkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl, C -C haloalkylaminothiocarbonyl, phenylcarbonyl, C -C alkylsulfonyl, C -C 1 6 1 6 1 6 haloalkylsulfonyl, C -C alkylaminosulfonyl or di(C -C ) alkylaminosulfonyl, and 1 6 1 6 10 n is an integer of 0, 1 or 2, wherein the compound represented by the formula (1) is not:

2. The condensed heterocyclic compound or its salt or an N-oxide thereof according to Claim 1, wherein 15 A is C(R ), A is a nitrogen atom, R is a hydrogen atom, R is a hydrogen atom or C -C haloalkyl, Y1 is a hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl, 20 Y2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, (C -C ) alkynyl optionally substituted with Y , C -C alkoxy, C -C alkylthio, C - 2 6 1 8 1 6 1 C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with Y , C1-C6 alkylsulfinyl, C1-C6 90g c alkylsulfonyl, -NH2, -NHR , nitro, phenyl, phenyl optionally substituted with Y , thiophenyl, pyridinyl or pyridinyl, 25 Y3 is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C1-C6 alkylthio, (C1-C6) alkylthio optionally substituted with Y , C1-C6 alkylsulfinyl, C1-C6 90a 90c 90b alkylsulfonyl, -C(O)R , -C(O)N(R )R , -C(O)OH, cyano or nitro, Y4 is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 90h 90g C -C alkylthio, C -C alkylsulfonyl, -N(R )R or cyano, 1 6 1 6 Y is C1-C8 alkoxycarbonyl, Y is C3-C6 cycloalkyl or trimethylsilyl, Y is a halogen atom or C -C haloalkyl, 5 R is C -C alkoxy, 90b 90c each of R and R is independently C1-C6 alkyl, R is C1-C6 alkyl, C1-C6 haloalkylcarbonyl, C1-C8 alkoxycarbonyl or phenylcarbonyl, and R is C -C alkyl. 10

3. The condensed heterocyclic compound or its salt or an N-oxide thereof according to Claim 1, wherein A is a nitrogen atom, A is C(R ), R is a hydrogen atom, 15 R is C -C haloalkyl, R is a hydrogen atom or C -C alkyl, Y1 is a hydrogen atom, Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, Y3 is a hydrogen atom, a halogen atom, C -C haloalkyl or cyano, and 20 Y4 is a hydrogen atom, a halogen atom or C -C alkoxy.

4. The condensed heterocyclic compound or its salt or an N-oxide thereof according to Claim 1, wherein R is a hydrogen atom, R is C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6 25 haloalkylsulfonyl, R is a hydrogen atom, R is a hydrogen atom or C -C alkyl, A is C1-C6 alkyl, each of Y1 and Y4 is a hydrogen atom, and 30 each of Y2 and Y3 is independently a hydrogen atom or C -C haloalkyl.

5. A condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with -S(O)nR is a ring represented by D1: Q is a ring represented by Q2: G is C(Y1), 10 G is C(Y2), G3 is C(Y3), G is C(Y4), A is C(R ), A is C(R ), 15 A is a nitrogen atom or C(R ), A is a nitrogen atom or C(R ), (excluding a case where both A and A are nitrogen atoms) R is C1-C6 alkyl, R is a hydrogen atom, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C6) alkylthio optionally substituted with R , C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, 5 R is C -C alkoxycarbonyl, R is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1- C6) alkylthio optionally substituted with R , C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl, R is C -C alkoxycarbonyl, 10 each of R and R is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with Y , C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, 15 (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C 1 6 1 6 1 6 90a 90b haloalkylsulfinyl, C -C alkylsulfonyl, C -C haloalkylsulfonyl, -C(O)R , -C(O)NHR , - 1 6 1 6 90c 90b 90e 90f 90g C(O)N(R )R , -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , - 90h 90g 90i 90j 90k 90j N(R )R , mercapto, -SC(O)R , -S(O)2NHR , -S(O)2N(R )R , -SF5, cyano, nitro, phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally 20 substituted with Y , Y is C1-C8 alkoxycarbonyl Y is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl, Y is a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, 1 6 1 6 1 8 1 8 cyano or nitro, 25 R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C1-C8 haloalkoxy, 90b 90c 90i 90j 90k each of R , R , R , R and R is independently C -C alkyl or C -C 1 6 1 6 haloalkyl, R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 30 haloalkoxy, C -C alkylamino, C -C haloalkylamino, di(C -C ) alkylamino or di(C -C ) 1 6 1 6 1 6 1 6 haloalkylamino, R is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1- C6) alkylamino or di(C1-C6) haloalkylamino, 90g 90h each of R and R is independently C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 6 5 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C haloalkoxycarbonyl, 1 6 1 8 1 8 C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl, C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C -C alkylaminosulfonyl or di(C -C ) alkylaminosulfonyl, and 1 6 1 6 n is an integer of 0, 1 or 2. 10

6. The condensed heterocyclic compound or its salt or an N-oxide thereof according to Claim 5, wherein A is a nitrogen atom, A is C(R ), R is C1-C6 haloalkyl, 15 R is a hydrogen atom or C -C alkyl, R is a hydrogen atom, a halogen atom or C -C alkyl, each of Y1 and Y4 is a hydrogen atom, Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and Y3 is a hydrogen atom or C -C haloalkyl. 20

7. A condensed heterocyclic compound represented by the formula (1) or its salt or an N-oxide thereof: wherein D substituted with -S(O)nR is a ring represented by D1: Q is a ring represented by Q4: 5 G1 is C(Y1), G2 is C(Y2), G is C(Y3), G is C(Y4), A is a nitrogen atom or C(R ), 10 R is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C -C haloalkynyl, C -C cycloalkyl (C -C ) alkyl or C -C halocycloalkyl (C -C ) alkyl, 2 6 3 6 1 6 3 6 1 6 each of R and R is independently a hydrogen atom, a halogen atom, C -C alkyl or C1-C6 haloalkyl, R is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, 15 each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C - C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with Y , C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C -C ) alkylthio optionally substituted with Y , C -C alkylsulfinyl, C -C 1 6 1 6 1 6 90a 90b haloalkylsulfinyl, C -C alkylsulfonyl, C -C haloalkylsulfonyl, -C(O)R , -C(O)NHR , - 1 6 1 6 90c 90b 90e 90f 90g 20 C(O)N(R )R , -C(O)OH, hydroxy, -OC(O)R , -OS(O)2R , -NH2, -NHR , - 90h 90g 90i 90j 90k 90j N(R )R , mercapto, -SC(O)R , -S(O)2NHR , -S(O)2N(R )R , -SF5, cyano, nitro, phenyl, phenyl optionally substituted with Y , heterocyclyl or heterocyclyl optionally substituted with Y , Y is C1-C8 alkoxycarbonyl Y is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl, Y is a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, C -C haloalkoxy, 1 6 1 6 1 8 1 8 5 cyano or nitro, R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C1-C8 haloalkoxy, 90b 90c 90i 90j 90k each of R , R , R , R and R is independently C -C alkyl or C -C 1 6 1 6 haloalkyl, 10 R is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-C6) alkylamino or di(C1-C6) haloalkylamino, R is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1- C6) alkylamino or di(C1-C6) haloalkylamino, 90g 90h 15 each of R and R is independently C -C alkyl, C -C haloalkyl, C -C 1 6 1 6 1 6 alkylcarbonyl, C -C haloalkylcarbonyl, C -C alkoxycarbonyl, C -C haloalkoxycarbonyl, 1 6 1 8 1 8 C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl, C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C -C alkylaminosulfonyl or di(C -C ) alkylaminosulfonyl, and 1 6 1 6 20 n is an integer of 0, 1 or 2.

8. The condensed heterocyclic compound or its salt or an N-oxide thereof according to Claim 7, wherein R is C -C alkyl, R is a hydrogen atom, 25 R is C1-C6 haloalkyl, R is a hydrogen atom or C -C alkyl, each of Y1 and Y4 is a hydrogen atom, Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and Y3 is a hydrogen atom or C1-C6 haloalkyl. 30 9. A condensed heterocyclic compound represented by the formula (1-a-I1) or its salt or an N-oxide thereof: wherein R is C -C alkyl, C -C haloalkyl, C -C alkenyl, C -C haloalkenyl, C -C alkynyl 1 6 1 6 2 6 2 6 2 6 5 or C2-C6 haloalkynyl, R is a hydrogen atom, a halogen atom, C -C alkyl, C -C haloalkyl, C -C alkoxy, 1 6 1 6 1 8 C -C haloalkoxy, C -C alkylthio, C -C haloalkylthio, C -C alkylsulfinyl, C -C 1 8 1 6 1 6 1 6 1 6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,

9. A is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, 10 each of R , R , Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C -C alkyl or C -C haloalkyl, and 1 6 1 6 n is an integer of 0, 1 or 2.

10. The condensed heterocyclic compound or its salt or an N-oxide thereof according to Claim 9, wherein 1 1a 15 each of R and A is independently C1-C6 alkyl, R is C1-C6 haloalkyl, Y2 is a hydrogen atom or C -C haloalkyl, Y3 is a hydrogen atom, a halogen atom or C -C haloalkyl, each of R , R , Y1 and Y4 is a hydrogen atom, and 20 n is an integer of 0, 1 or 2.

11. A method of controlling internal or external parasites in or on mammals or birds, the method comprising administering to the mammal or bird in need thereof an effective amount of a condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of Claims 1 to 10, wherein the mammal is not a human. 25

12. The method of Claim 11, wherein the external parasites are Siphonaptera or ticks.

13. A method of controlling insects, mites, or ticks, the method comprising applying an effective amount of a condensed heterocyclic compound or its salt or an N-oxide thereof according to any one of Claims 1 to 10.

14. A method of controlling agricultural pests, the method comprising applying an effective amount of a condensed heterocyclic compound or its salt or an N-oxide thereof 5 according to any one of Claims 1 to 10 to seeds or to soil.

15. The method of Claim 14, wherein the condensed heterocyclic compound or its salt or an N-oxide thereof is applied to seeds by dipping.

16. The method of Claim 14, wherein the condensed heterocyclic compound or its salt or an N-oxide thereof is applied to soil by irrigation. 10

17. The condensed heterocyclic compound or its salt or an N-oxide thereof of any one of Claims 1, 5, 7, and 9, substantially as herein described with reference to any example thereof.

18. The method of any one of Claims 11, 13, or 14, substantially as herein described with reference to any example thereof.