WO2007011022A1 - 3-(isoquinoline-1-yl)quinoline derivative - Google Patents

Abstract

It is intended to provide a 3-(isoquinoline-1-yl)quinoline derivative (I), a salt thereof and an agrochemical composition containing the same as an active ingredient, particularly an agricultural and horticultural bactericide that shows an excellent effect on a variety of plant pathogens (particularly for rice blast) without causing damage to a host plant. The 3-(isoquinoline-1-yl)quinoline derivative (I) represented by the formula: (I) (wherein the ring A and the ring B: a benzene ring or the like, R1 to R4: H, halogen, alkyl, OH, an alkoxy group or the like, Q: N, N-R5 (R5: H, OH, an alkyl group or the like), X: halogen, alkyl or the like, Y: halogen, an alkyl group or the like, n: 0 to 4, m: 0 to 6, a bond including a dotted line: a single bond or a double bond) or a salt thereof.

Description

 Specification

 3-(Isoquinoline-1-yl) quinoline derivatives

 Technical field

 [0001] The present invention relates to a 3- (isoquinoline-1-yl) quinoline derivative or a salt thereof, and an agrochemical composition containing them as an active ingredient.

 Background art

 [0002] In Patent Document 1 and Patent Document 2, a 6-aryl phenanthridine compound in which a cyclohexane ring is formed between the 3-position and 4-position of a dihydroisoquinoline ring is used as a PDE4 inhibitor. Patent Document 3 describes a 6-arylfuroisoquinoline compound that forms a dihydrofuran ring between positions 7 and 8 of the dihydroisoquinoline ring as an entry inhibitor. Forces There is no description of 3-dihydroisoquinoline-1-ylquinoline derivatives in which the isoquinoline ring is not condensed with another ring, and there is no description of the agricultural chemical composition (agricultural and horticultural fungicide).

 [0003] In addition, Non-Patent Documents 1 to 4 describe the synthesis of 3- (isoquinoline-1-yl) quinoline compound, but do not describe an agrochemical composition (agricultural and horticultural fungicide). .

 [0004] Thus, it has not been known so far that 3- (isoquinoline-1-yl) quinoline derivatives can be used as agricultural chemical compositions (agricultural and horticultural fungicides).

 Patent Document 1: Pamphlet of International Publication No. 00Z42019

 Patent Document 2: Pamphlet of International Publication No. 02Z06270

 Patent Document 3: JP 2003Z 171381

 Non-Patent Document 1: Indian Journal of Chemistry, 1969, 7 (10), 1010-1016

 Non-Patent Document 2: Indian Journal of Chemistry, 1970, 8 (6), 505-508

 Non-Patent Document 3: Indian Journal of Chemistry, 1985, 24B (7), 737-746

 Non-Patent Document 4: Indian Journal of Chemistry, 1986, 25B (10), 1072-1078

 Disclosure of the invention

 Problems to be solved by the invention

[0005] An object of the present invention is to have an excellent bactericidal activity against various plant diseases, An object of the present invention is to provide 3 (isoquinoline 1-yl) quinoline derivatives or salts thereof useful as active ingredients, and an agrochemical composition containing them as active ingredients.

 Means for solving the problem

 [0006] As a result of intensive research on the 3- (isoquinoline-1-yl) quinoline derivative for many years, the present inventors have shown that it has excellent bactericidal activity against various plant diseases and has an agrochemical composition. Rice blast (Pyricularia oryzae) and gray of tomato, cucumber and green beans that are useful as an active ingredient in foods, and often cause serious damage to agricultural and horticultural crops, especially among plant fungi The present invention was completed by discovering that it is possible to control mold disease (Botrytis cinerea) at a low dose.

 [0007] That is, the present invention provides 3 (isoquinoline 1-yl) quinoline derivatives or salts thereof, which are useful as active ingredients of agricultural chemical compositions, and agricultural chemical compositions containing them as active ingredients.

 [0008] The object of the present invention is to have an excellent bactericidal activity against various plant diseases and to be useful as an active ingredient of an agrochemical composition. 3 (Isoquinoline 1yl) quinoline derivative or a salt thereof, and effective It is providing the agrochemical composition contained as a component.

 The invention's effect

 [0009] The present invention can be used as an agrochemical composition, in particular, as an agricultural and horticultural fungicide, and exhibits excellent effects on various phytopathogenic fungi, particularly rice blast, which do not damage the host plant. A 3- (isoquinoline-1-yl) quinoline derivative or a salt thereof, which is excellent as an agricultural and horticultural fungicide, and an agrochemical composition containing these as active ingredients.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0010] The present invention provides a general formula

(式中、

(Where

 Ring A and ring B may be the same or different

 An optionally substituted benzene ring; an optionally substituted C 1 -C cycloalkyl ring (

 3 8

Wherein the cycloalkyl ring may be partially unsaturated); or may be substituted, the same or different 1 to 4 identical, with the group forces also comprising oxygen, nitrogen and sulfur forces selected Or a 5- to 6-membered heteroaryl ring containing different ring-constituting heteroatoms, wherein the heteroaryl ring may be partially hydrogenated,

R ³ and R ⁴ may be the same or different

 From hydrogen atom; neuron atom; neuron atom, c to c alkoxy group and phenoxy group

 1 6

A group force that may be substituted with 1 to 3 substituents of the same or different ones selected from c to c alkyl groups; hydroxyl groups; rho, rogen atoms, c to c alkoxy groups, and phenoxy groups.

1 6 1 6

The group force may also be substituted with 1 to 3 substituents of the same or different one selected from a ~ C alkoxy group; a norogen atom, a C 1 -C alkoxy group and a phenoxy group.

1 6 1 6

Group power selected by the same or different selected 1 to 3 substituents, C

 1

~ C alkylthio group; consisting of a norogen atom, a C ~ C alkoxy group and a phenoxy group

6 1 6

Group power may also be substituted with the same or different 1 to 3 substituents selected C ~

 1

C alkylsulfinyl group; whether it is a norogen atom, a C to C alkoxy group or a phenoxy group

6 1 6

May be substituted with 1 to 3 substituents which are the same or different, and may be substituted with 1 to 3 C alkylsulfol groups; a norogen atom, a C to C alkoxy group and a phenoxy group. C 1 -C cycloalkyl group which may be substituted with 1 to 3 identical or different substituents; a nonogen atom, a C 1 -C alkoxy group and a phenoxy

3 6 1 6

Group power as basic force C 1 -C cycloalkyloxy group which may be substituted with the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and a phenol

3 6 1 6

Noxy group power Group power C 1 -C cycloalkylthio group optionally substituted by the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and

 3 6 1 6

Phenoxy group force Group power C 1 -C alkenyl group optionally substituted by 1 to 3 selected or different substituents; a norogen atom, a C 1 -C alkoxy group and a phenyl group

 2 6 1 6

Noxy group strength group power is selected by the same or different 1 to 3 substituents C to c-alkoxy group; a norogen atom, c to c alkoxy group and

2 6 1 6

ヱ Noxy group force Group force C 1 -C alkenylthio group optionally substituted by the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and

 2 6 1 6 Phenoxy group force Group force C 1 -C alkyl group optionally substituted by 1 to 3 identical or different substituents selected; a nitrogen atom, a C 1 -C alkoxy group and a phenyl group

 2 6 1 6

Noxy group force Group force C 1 -C alkyloxy group optionally substituted by 1 to 3 identical or different substituents selected; a nitrogen atom, C 1 -C alkoxy group and

 2 6 1 6

ヱ Noxy group power Group force Selected C to C alkylthio group optionally substituted with 1 to 3 different substituents; Nonogen atom, same or different 1 to 3

 2 6

C to c alkyl group, c to c alkoxy group,

 1 6 1 6

May be substituted with one or different 1 to 2 C 1 -C alkyl or acyl.

 1 6

Iamino group, nitro group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group

 1 6

Group power also may be substituted with the same or different 1 to 6 substituents selected; aryl group; a norogen atom, optionally substituted with 1 to 3 different halogens C -C alkyl group, C -C alkoxy group, 1 to 2 identical or different (amino group, nitro group, cyano optionally substituted by DC -C alkyl or acyl)

1 6

Group, hydroxyl group, mercapto group and c-c alkylthio group power

 1 6

Alternatively, it may be substituted with 1 to 6 different substituents, or an aryloxy group; a nitrogen atom, C 1 to C 6 optionally substituted with 1 to 3 different halogens

 16 alkyl group, C to C alkoxy group, the same or different 1 to 2 C to C alkyl group

 1 6 1 6 or an amino group which may be substituted with an acyl, a nitro group, a cyano group, a hydroxyl group, a mercapto group and a C-C alkylthio group group power of the same or different selected 1-6

 1 6

A arylthio group; a halogen atom, a C 1 -C alkyl group which may be substituted with 1 to 3 halogen atoms, the same or different, and a C 1 -C alkoxy group Force Heteroaryl group optionally substituted with the same or different 1 to 6 substituents selected; Nonogeneous atom, optionally substituted with 1 to 3 different halogens C to C Alkyl group and C-C alkoxy group group force is also selected Hetero that may be substituted with the same or different 1 to 6 substituents Aryloxy group; a group of force consisting of a C-C alkyl group and a C-C alkoxy group optionally substituted by 1 to 3 halogen atoms, the same or different halogens selected 1 to 6 identical or different A heteroarylthio group; a norogen atom, substituted with 1-3 identical or different halogens, and a C-C alkyl group, C-C An alkoxy group, the same or different 1 to 2 C to C

1 6 1 6 1 6 Amino group, nitro group, cyano group, hydroxyl group which may be substituted with alkyl or acyl

, A mercapto group and a c to c alkylthio group force are also selected, the same or different

 1 6

Aralkyl group which may be substituted with 1 to 6 substituents; halogen atom, C to C alkyl group which may be substituted with 1 to 3 different halogens, C to C

 1 6 1 6 alkoxy group, identical or different 1 to 2 C 1 -C alkyl or acyl

 1 6

Optionally substituted amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c

 1 6 alkylthio group power group power selected Aralkyloxy group which may be substituted with 1 to 6 substituents which may be the same or different; a norogen atom, substituted with 1 to 3 halogens which may be the same or different C 1 -C alkyl group, C 1 -C alkoxy group, the same or different 1 to 2 C 1 -C alkyl or acyl may be substituted

 1 6

From amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkylthio group

 1 6

Or a group force selected from 1 to 6 substituents selected from the same or different, and may be an aralkylthio group; an acyl group; an acyloxy group; an acylthio group; or a cyano group, or

^{Two of} RR ² , R ³ and R ⁴ are taken together to form a halogen atom, c-c alkyl.

 16 groups, c to c alkoxy groups and phenoxy groups

1 6

A C 1 -C cycloalkyl ring optionally substituted with 1 to 3 substituents (wherein

 3 8

The chloroalkyl ring may contain 1 to 3 heteroatoms selected from the group forces of oxygen, nitrogen and sulfur), or R ¹ and R ² ; or R ³ and R ⁴ are , Taken together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ^{4 taken} together represent a methylene group, or R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ together represent a single bond, Q is a nitrogen atom or a formula N—R ⁵ group (wherein R ⁵ is a hydrogen atom; a hydroxyl group, the same or different 1 to An amino group optionally substituted by two C 1 -C alkyl or acyl; Halogen atoms, c-c alkoxy groups and phenoxy groups

1 6

Or a C 1 -C alkyl group optionally substituted with 1 to 3 different substituents;

 1 6

Atoms, c to c alkoxy groups, and phenoxy group forces are the same or selected

 1 6

A C 1 -C alkoxy group optionally substituted with 1 to 3 different substituents;

 1 6

The same or different group forces are also selected.

1 6

A C 1 -C alkylsulfinyl group optionally substituted with 1 to 3 substituents;

 1 6

Gen atom, c-c alkoxy group and phenoxy group power

 1 6

Is a C 1 -C alkylsulfonyl group optionally substituted with 1 to 3 different substituents;

 1 6

Halogen atoms, c-c alkoxy groups and phenoxy groups

 1 6

Or a C 1 -C alkyl sulfamo optionally substituted with 1 to 3 different substituents.

 1 6

Selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

C 1 -C alkenyl optionally substituted with 1 to 3 identical or different substituents

 2 6 oxy group; selected from the group forces of a norogen atom, c to c alkoxy group and phenoxy group

 1 6

C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents

26 Roxy group; a C atom-alkyl group, a C-C alkoxy group, a C-C alkoxy group, which may be substituted with the same or different 1 to 3 halogen atoms, the same or different 1 to 2 c to c An amino group optionally substituted by alkyl or acyl, a nitro group, a cyan group,

1 6

Hydroxyl group, mercapto group and C-C alkylthio group

 1 6

Is an aralkyl group optionally substituted with 1 to 6 different substituents; a norogen atom, a C 1 to C alkyl group optionally substituted with 1 to 3 identical or different halogens

 1 6

 A C to C alkoxy group, the same or different 1 to 2 C to C alkyl or

1 6 1 6

An amino group optionally substituted by a sil, a nitro group, a cyano group, a hydroxyl group, a mercapto group, and

C-C alkylthio group power group power chosen 1-6 identical or different substitutions

1 6

Substituted with a group may be an aralkyloxy group; an acyl group; an acyloxy group; tri- (C

 1

-C alkyl) silyl group; or zi (c-c alkoxy) phosphoryl group. Represents

X may be the same or different when n is an integer from 2 to 4

A halogen atom; from the group consisting of a norogen atom, a C to C alkoxy group and a phenoxy group C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents selected

 1 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

C 1 to C cycloalkyl optionally substituted with 1 to 3 identical or different substituents

 3 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

C 1 -C alkenyl optionally substituted with 1 to 3 identical or different substituents

 2 6 groups; the same selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

A C 1 -C alkyl group optionally substituted with one or different 1 to 3 substituents;

 2 6

Substituted with 1 to 3 halogen atoms, the same or different! /, C

 1

~ C alkyl group, C ~ C alkoxy group, same or different 1-2 C ~ C al

6 1 6 1 6 Amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkylthio group which may be substituted with a kill or acyl group group power of the same or different selected

 1 6

An aryl group which may be substituted with 1 to 6 substituents; a halogen atom, a C to C alkyl group and a C to C alkoxy group which may be substituted with the same or different 1 to 3 halogens Group force selected heteroaryl group optionally substituted with 1 to 6 substituents of the same or different selected; a nonogen atom, a C to C alkoxy group and a phenoxy group

 1 6

C group power is selected C-C alkoxy group which may be substituted with the same or different 1 to 3 substituents selected; group atom consisting of a nonogen atom, C-C alkoxy group and phenoxy group selected C 1 -C alkylthio group which may be substituted with the same or different 1 to 3 substituents; the same or different 1 to 3 group forces consisting of a nonogen atom, a C 1 -C alkoxy group and a phenoxy group are also selected It may be substituted with 1 substituent group, ie, a C alkyl sulfier group; a nitrogen atom, a C 1 to C alkoxy group, and a phenoxy group group power of the same or different selected 1 to 3 substituent groups Optionally substituted C 1 -C alkyl sulfol group; one or two C 2 -C alkyls which are the same or different

 1 6 1 6 substituted with a kill group or an acyl group may be an amino group; an acyl group; a cyan group; or C

 1

C alkyl group, c to c alkyl group, c to c alkyl group, aryl group and hetero

6 2 6 2 6

Represents the N-hydroxy (C to C alkane) imidoyl group in which the hydrogen atom of the hydroxyl group may be substituted with the selected substituent.

 1 6

Y may be the same or different when m is an integer of 2 to 6, A halogen atom; from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents selected

 1 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

C 1 to C cycloalkyl optionally substituted with 1 to 3 identical or different substituents

 3 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

C 1 -C alkenyl optionally substituted with 1 to 3 identical or different substituents

 2 6 groups; the same selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group

 1 6

A C 1 -C alkyl group optionally substituted with one or different 1 to 3 substituents;

 2 6

Substituted with 1 to 3 halogen atoms, the same or different! /, C

 1

~ C alkyl group, C ~ C alkoxy group, same or different 1-2 C ~ C al

6 1 6 1 6 Amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkylthio group which may be substituted with a kill or acyl group group power of the same or different selected

 1 6

An aryl group which may be substituted with 1 to 6 substituents; a halogen atom, a C to C alkyl group and a C to C alkoxy group which may be substituted with the same or different 1 to 3 halogens Group force selected heteroaryl group optionally substituted with 1 to 6 substituents of the same or different selected; a nonogen atom, a C to C alkoxy group and a phenoxy group

 1 6

C group power is selected C-C alkoxy group which may be substituted with the same or different 1 to 3 substituents selected; group atom consisting of a nonogen atom, C-C alkoxy group and phenoxy group selected C 1 -C alkylthio group which may be substituted with the same or different 1 to 3 substituents; the same or different 1 to 3 group forces consisting of a nonogen atom, a C 1 -C alkoxy group and a phenoxy group are also selected It may be substituted with 1 substituent group, ie, a C alkyl sulfier group; a nitrogen atom, a C 1 to C alkoxy group, and a phenoxy group group power of the same or different selected 1 to 3 substituent groups Optionally substituted C 1 -C alkyl sulfol group; one or two C 2 -C alkyls which are the same or different

 1 6 16 substituted with a kill group or an acyl group may represent an amino group; an acyl group; a cyan group; or a hydroxyl group;

 n represents an integer of 0 to 4,

m represents an integer of 0 to 6, A bond containing a dotted line represents a single bond or a double bond,

 In the case where the bond including Q and the dotted line is a single bond, the bond including the other dotted line represents a single bond. ]

 Or a salt thereof.

R²、 R³及び R⁴である力、

R²、 R³及び R⁴のうちの二つは、一緒になつて、置換され ていてもよい C In the above compound (I), when R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ force together represent a single bond, R ¹ and R ² are bonded. The bond between the carbon atom to which R ³ and R are bonded is a double bond, and the substituents on the monocycle containing Q are R ′ (or R ² ) and R ³ (or R ⁴ ), and, R ¹ and R ³ or R ^4; or R ² and R ³ or R ⁴ together, if not represent a single bond, the carbon atom to which R ¹ and R ² are attached The carbon atom bond between R ³ and R ⁴ is a single bond, and the substituent on the monocycle containing Q is

Forces that are R ² , R ³ and R ⁴ ,

^{Two of} R ² , R ³ and R ⁴ are taken together and optionally substituted C

The force to form a 3-C cycloalkyl ring or R ¹ and R ² ; or R ³ and R ⁴ together represent 8 an oxo group or R ¹ and R ² ; or R ³ and R 4 ⁴ together represent a methylene group.

 [0012] In the present invention !, the "C to C cycloalkyl ring" of ring A and ring B (wherein the cycloalkyl

 3 8

 For example, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclopentene ring, cyclohexane ring, cyclohexene ring, cycloheptane ring or cyclooctane. Preferably a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclopentene ring, a cyclohexane ring or a cyclohexene ring, and particularly preferably a cyclopentane ring or a cyclohexane ring. It is.

In the present invention, the “5- to 6-membered heteroaryl ring” of ring A and ring B (wherein the heteroaryl ring may be partially hydrogenated) is, for example, a furan ring, a dihydrofuran ring, Thiophene ring, dihydrothiophene ring, pyrrole ring, oxazole ring, isoxazole ring, dihydroisoxazole ring, thiazole ring, isothiazole ring, imidazole ring, virazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring , A pyridine ring, a pyrazine ring, a pyridazine ring, an oxazine ring or a dihydrooxazine ring, preferably a furan ring, a thiophene ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a pyrazole ring, a pyridine Ring, pyrazine ring, oxazine ring or Is a dihydrooxazine ring, more preferably a thiophene ring, an oxazole ring, a thiazole ring, a pyridine ring, a pyrazine ring or a dihydrooxazine ring, and particularly preferably for ring A, a pyridine ring And ring B is a pyridine ring or a dihydroxazine ring.

In the present invention, a “C to C alkyl group” (an alkyl group having 1 to 6 carbon atoms) such as R ¹ or the like

 1 6

 "C-c alkyl moiety" such as "c-c alkoxy group" means either a straight or branched chain

1 6 1 6

 For example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sbutyl group, tbutyl group, pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3, 3 dimethylbutyl group, 2,2 dimethylbutyl group, 1,1-dimethylbutyl group 1, 2-dimethylbutyl group, 1,3 dimethylbutyl group, 2,3 dimethylbutyl group, and 2-ethylbutyl group, and preferably a linear or branched alkyl group having 1 to 5 carbon atoms ( A C 1 -C alkyl group), and more preferably a linear or branched alkyl group having 1 to 4 carbon atoms.

1 5

 A kill group (C-C alkyl group), and even more preferably a straight chain or straight chain having 1 to 3 carbon atoms.

 14

 Is a branched chain alkyl group (c to c alkyl group), particularly preferably a methyl group,

 13

 Group or propyl group, and most preferably a methyl group or an ethyl group.

In the present invention, a “C to C alk group” such as R ¹ (alkal having 2 to 6 carbon atoms).

 2 6

 Group) or “c to c alkyl moiety” such as “c to c alkyloxy”

 2 6 2 6

It can contain any number of double bonds, which can be either branched. For example, bur group, proper 1-l-yl group, aryl group, iso-propyl group, but-1-ene-1-yl group, but-2-ene-1-yl group, but- yl 3—1—yl group, 2—methylpropylene 2—ene 1—yl group, 1 methylproper 2—ene 1—yl group, penter 1—ene 1—yl group, penter 2—one 1-yl group, penter 3-ene 1-yl group, penta-4-ene 1-yl group, 3-methylbuta-2-ene 1-yl group, 3-methylbutane 3-ene 1 Hexyl group, hexene 1-yl group, hexene 2-eneyl group, hexase-3 ene-1-yl group, hexene 4-ene-1-yl group, hexene-5-eneyl group, 4-methylpenter-3 1-yl group Preferably, it is a bur group, a propylene group, a propyl group, a aralkyl group or an isoprobe group.

Group, particularly preferably a vinyl group or an aryl group.

In the present invention, a “C to C alkyl group” such as R ¹ (an alkyl having 2 to 6 carbon atoms).

 2 6

 Group) or `` c-c alkynyl moiety '' such as `` c-c alkynyloxy group '' is linear or

 2 6 2 6

 It can contain any number of triple bonds, whether branched or branched. For example, Etul, Proper 1 in 1 group, Proper 2-in 1 group, Butter 1 in 1 group, Butter 3 in 1 group, 1 Methyl prop 2-in 1 1-yl Group, penta-1-1-in-1-yl group, penta-1-in-1-yl group, hex-1-in-1-yl group, hexer-5-in-1-yl group, and preferably Etul group or proper 2-in-1yl group (propargyl group), particularly preferably an ethur group.

In the present invention, the “aryl moiety” such as “aryl group” or “aryloxy group” such as R ¹ is an aromatic hydrocarbon group having 6 to 14 carbon atoms, such as phenyl group, 1 naphthyl group. It may be a thiol group, a 2-naphthyl group, an anthracyl group, a phenanthryl group, or a acenaphthyl group, preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and particularly preferably. Is a phenol group.

In the present invention, a “heteroaryl moiety” such as a “heteroaryl group” or “heteroaryloxy group” such as R ¹ is partially hydrogenated by condensation with a benzene ring or the like. Oxygen atoms, nitrogen atoms and sulfur nuclear power groups that may be converted to 5- to 7-membered heteroaryl groups containing 1 to 4 identical or different ring heteroatoms, such as furyl Group, phenyl, pyrrolyl, oxazolyl, isoxazolyl, dihydroisoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, birazyl Group, an azepinyl group or an oxazepine group, preferably a furyl group, a chenyl group, an oxazolyl group, an isoxazolyl group. A thiazolyl group, an isothiazolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a bilazyl group or a pyridazyl group, and more preferably a furyl group, a enyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, or a pyrazolyl group. , Pyridyl group or virazyl group, particularly preferably furyl group, -Group or pyridyl group.

 In addition, benzene ring and condensed heteroaryl groups include, for example, benzofuranyl group, isobenzofuranyl group, benzochelyl group, indolyl group, isoindolyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group. Group, benzothiazolyl group, benzothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, benzotriazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, naphthyridinyl group Group, prill group, pteridyl group, carbazolyl group, carbolyl group, ataridyl group, 2-ataridyl, 3-ataridyl, 4-ataridyl, 9-attaridyl, phenoxazyl group, phenothiazyl group or phenazyl group, preferably , Benzofuryl group, benzothia There Le group - Lil group, quinolyl group, quinazolinyl group, or Nafuchiriji

Particularly preferred is a quinazolyl group or a naphthylyl group.

In the present invention, “aralkyl moiety” such as “aralkyl group” or “aralkyloxy group” such as R ¹ is one or more hydrogen atoms of the “C 1 -C alkyl group”. The atom is

 1 6

 For example, a benzyl group, a 1 naphthylmethyl group, a 2-naphthylmethyl group, an anthracenylmethyl group, a phenanthrylmethyl group, an acenaphthylmethyl group, a diphenylmethyl group, a 1 phenethyl group. Group, 2-phenethyl group, 1 (1-naphthyl) ethyl group, 1- (2-naphthyl) ethyl group, 2- (1naphthyl) ethyl group, 2- (2naphthyl) ethyl group, 3-phenylpropyl group , 3— (1 naphthyl) propyl group, 3— (2 naphthyl) propyl group, 4 1-phenol butyl group, 4 1 (1 naphthyl) butyl group, 4— (2 naphthyl) butyl group, 5 phenol pentyl group , 5- (1-naphthyl) pentyl group, 5- (2 naphthyl) pentyl group, 6-phenylhexyl group or 6- (1-naphthyl) hexyl group, 6- (2naphthyl) hexyl group Preferably, a benzyl group 1 phenethyl, 2 phenethyl or 3 Hue - a Rupuropiru group, particularly preferably a benzyl group or a 2-phenethyl group. Also preferred are benzyl, phenethyl, diphenylmethyl or naphthylmethyl! /.

[0018] Te you, the present invention, R ¹ and R ² or the like to form "C -C cycloalkyl ring" means a monocyclic also

 3 8

Is a double ring and may contain 1 to 3 heteroatoms selected from the group forces of oxygen, nitrogen and sulfur, for example, cyclopropyl ring, cyclobutyl ring, cyclopentyl ring, It can be a chlorohexyl ring, cycloheptyl ring, cyclooctyl ring, norbornyl ring, tetrahydrofuryl ring, tetrahydrochenyl ring, morpholine ring or thiomorpholine ring, preferably a cyclopropyl ring, a cyclobutyl ring, a cyclopentyl ring, a cyclo A hexyl ring or a cycloheptyl ring, more preferably a cyclobutyl ring, a cyclopentyl ring or a cyclohexyl ring, and particularly preferably a cyclopentyl ring.

In addition, “C to C cycloalkyl group” or “C to C cycloalkyloxy group” such as R ^{1 and the} like

 3 6 3 6

 The `` C to C cycloalkyl moiety '' of, for example, cyclopropyl group, cyclobutyl group,

3 6

 It may be an oral pentyl group or a cyclohexyl group, preferably a cyclopropyl group, a cyclobenzoyl group or a cyclohexyl group, and particularly preferably a cyclopentyl group or a cyclohexyl group.

 In the present invention, “C to C alkyl group, C to C alkyl group, C to C alkyl group” of

 1 6 1 6 1 6

-Group, aryl group and heteroaryl group force N-hydroxy (C-C alkane) imidoyl group in which the hydrogen atom of the hydroxyl group may be substituted with a selected substituent

 1 6

 The above-mentioned “C” is added to the hydroxyl group of an N hydroxy (C to C alkane) imidoyl group having 1 to 6 carbon atoms.

 1 6 1

-C alkyl group ", the" c-c alkenyl group ", the" c-c alkynyl group ", the above

6 1 6 1 6

 “Aryl group” and the above-mentioned “heteroaryl group” group power which is a group which may be substituted with a selected substituent, for example, hydroxyiminomethyl group, N hydroxyethaneimido group, N hydroxypropane Imidoyl group, N hydroxybutaneimidoyl group, methoxyiminomethyl group, N-methoxyethaneimidoyl group, N ethoxyethaneimidoyl group, N butoxyalkaneimidoyl group, N allyloxettanimidoyl group, N-phenoxyethanimidoyl group, N-methoxypropaneimidoyl group, N-methoxybutanimidoyl group or N-methoxyhexanimidyl group, preferably hydroxyiminomethyl group, methoxyiminomethyl group, N-methoxyethaneimidoyl group, N-ethoxyethaneimidoyl group, N-aryloxy A Tan'imidoiru group or N full enoki Chez Tan imidoyl group, particularly preferably a N- methoxy E Tan imide yl group or N- ethoxy E Tan imidoyl group.

In the present invention, the “halogen atom” such as R ¹ is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably Is a fluorine atom or a chlorine atom, most preferably a fluorine atom.

In the present invention, “an optionally substituted C to C alkyl group optionally substituted with 1 to 3 halogen atoms” such as R ^1, or “an optionally substituted C to C C

 The “optionally substituted c to c alkyl moiety” of the “1 6 1 6 alkoxy group” is, for example, the above “c

 1 6 1

~ C alkyl group ", trifluoromethyl group, trichloromethyl group, difluoromethyl group, di

6

 Chloromethyl group, dibromomethyl group, fluoromethyl group, chloromethyl group, bromomethyl group, chloromethyl group, 2, 2, 2-trichloroethyl group, 2, 2, 2-trifluoroethyl group, 2 bromoethyl group, 2 chloroethyl, 2 fluoroethyl, 3 chloropropyl, 3, 3, 3 trifluoropropyl, 4 chlorobutyl, 3 fluoro-2 methyl propyl P pinole, 3, 3, 3 卜!; P 2 -Methylolep P pinole group or 6, 6, 6 卜 hexyl group, preferably the above-mentioned “C to C” which may be substituted by the same or different 1 to 3 “halogen atoms” Alkyl group ”, and more preferably the same or young

 14

 May be substituted by 1 to 3 different “fluorine or chlorine atoms”,

 1

˜c alkyl group ”, and even more preferably, methyl group, ethyl group, propyl group,

Three

 It is a romethyl group or a trifluoromethyl group, particularly preferably a methyl group, an ethyl group or a trifluoromethyl group.

[0023] In the present invention! /, "Norogen atom, C-C alkoxy group and phenoxy group such as R ¹ ?"

 1 6

 The group force may also be selected from the same or different 1 to 3 substituents which may be substituted with a C to C alkyl group, or “optionally substituted C to C alkoxy.

The “optionally substituted c to c alkyl moiety” such as “1 6 1 6 group” is, for example, the above “c to c alkyl group”.

 1 6 1 6 kill group ”, the above-mentioned“ C-C alkyl group which may be substituted with 1 to 3 identical or different halogen atoms ”, methoxymethyl group, ethoxymethyl group, ethoxyethyl group, pro

1 6

Poxymethyl group, phenoxymethyl group, phenoxychetyl group, 2-methoxy-1-chloromethyl group, 3-phenoxy-2 bromo-2-methoxypropyl group, preferably methyl group, chloromethyl group, dichloromethyl group, trifluoromethyl group Group, methoxymethyl group, ethoxymethyl group, phenoxymethyl group, ethyl group or trifluoroethyl group, particularly preferably methyl group, chloromethyl group, dichloromethyl group, trifluoromethyl group or methoxymethyl group. It is. [0024] In the present invention! /, A R ¹ or the like "a nonogen atom, a C to C alkoxy group and a phenoxy group?"

 1 6

 May be substituted with the same or different 1 to 3 substituents selected, or a C 1 to C alkenyl group or a C 1 to C alkenyl optionally substituted with the substituent.

The “optionally substituted c to c alkenyl moiety” such as “2 6 2 6 ruoxy group” is, for example, the above “

 2 6

 C to C alkenyl group ”, 3 chloroallyl group, 4 bromo-2 butyr group, 3-methoxy group

2 6

 It can be a 2-propyl group, 4 ethoxy 3 butur group, 3 phenoxy 2 butur group or 4 methoxy 3 chloro 2 butenyl group, preferably vinyl group, aryl group, 3 chloroallyl group Or a 3-methoxy-2-probe group, particularly preferably a bur group or an aryl group.

[0025] In the present invention! /, "N ^1, such as R ¹ atom, C 1 -C alkoxy group and phenoxy group?"

 1 6

 The group force may also be substituted with the same or different 1 to 3 selected substituents, or a C 1 -C alkyl group ”or“ optionally substituted C 1 -C alkyl group ”.

The “optionally substituted c to c alkenyl moiety” such as “2 6 2 6 ruoxy group” is, for example, the above “

 2 6

 C to C alkyl group ”, 3 black mouth 2 propyl group, 4 bromo-2-propyl group

2 6

 , 3-methoxy-2-propyl group, 4-ethoxy-3-buturyl group, 3-phenoxy-2-buturyl group or 4-methoxy-4-chloro-2-buturyl group, preferably ethyl group, proper 2-in-1-yl Group, 3-chloro 2-propyl group or 4-bromo 2-butyl group, particularly preferably ethul group, proper 2-in-1-yl group or 3-chloro 2-propyl group.

[0026] In the present invention, R ¹ or the like may be substituted with the same or different 1-2 C 1 -C alkyl groups.

 1 6

 The “amino group that may be substituted” is preferably the same or different one of the above-mentioned “C 1 -C 4”.

 An amino group which may be substituted with “16 alkyl group”, and more preferably an amino group which may be substituted with one or two of the above-mentioned “C 1 -C alkyl group”. Yes, special

 14

 Preferable is a dimethylamino group or a jetylamino group.

In the present invention, an “acyl moiety” such as “acyl group” or “acyloxy group” such as R ¹ is a formyl group, a carbocycle group to which the “c to c alkyl group” is bonded ( c to c alkyl force

 1 6 2 7 carbonyl group) and a carbo group (C 1 -C alkenyl group) to which the above “C 1 -C alkenyl group” is bonded.

2 6 3 7 dicarbol group), a carbol group to which the aforementioned “aryl group” is bonded (“aryl group”) Ru group "), the above-mentioned" c ~

 A carbo group to which a 1 c alkoxy group is bonded (

 6 c ~

 2c alkoxy force 7

 A carbonyl group (to which a “c to c alkylthio group” is bonded)

 1 6 c ~

 2 c-ar 7 -kilothiocarbol group) or the above-mentioned “same or different 1-2 C-C alkyl”

 A carbo group to which an amino group optionally substituted with 1 6 groups "is bonded (c ~

 2c alkylamino 7

 Carbon group), preferably formyl group, c to alkylcarbonyl group (carbon).

 2 c 5

 It is a linear or branched group of several 2-5. The following groups are the same), C to C al

 3 5 Kenylcarbonyl group, benzoyl group, naphthoyl group, c to c alkoxycarbonyl group

 twenty five

 C to c alkylthiocarbonyl group or c to c alkylaminocarbonyl group

2 5 2 5

 More preferably, a formyl group, a C-C alkylcarbonyl group, a benzoyl group, a C-

 2 5 2

C alkoxycarbonyl group or c-c alkylaminocarbonyl group, particularly preferred

5 2 5

 Acetyl, methylaminocarbol, dimethylaminocarboro, methoxycarbonyl, ethoxycarboro or benzoyl are preferred, and acetyl or methyl is most preferred. It is an aminocarbo group. C ~ group,

 2c alkylcarboni

 Five

 Also preferred are c to c alkoxycarbo groups and c to c alkylaminocarbo groups.

2 5 2 5

 A group of acyl groups.

[0028] In the present invention, the same or different 1-2 C-C alkyl groups such as R ¹ or the like

 1 6

 The “amino group optionally substituted with an acyl group” is, for example, the above-mentioned “amino group optionally substituted with 1 to 2 identical C to C alkyl groups” or the same or different.

 1 6

 In addition, 1 to 2 of the “acyl groups” may be substituted amino groups, and preferably, the same or different 1 to 2 of the “acyl groups” may be substituted. And an amino group, more preferably an acetylamino group, a benzoylamino group, a methoxycarboamino group, or a mono- or dimethylaminocarbonyl group, and particularly preferably an acetylamino group.

[0029] In the present invention, a "norogen atom such as R ¹ , a C to C alkyl group which may be substituted with the same or different 1 to 3 halogen atoms, a C to C alkoxy group, the same or different 1

 1 6 1 6

 Amino group, nitro group, optionally substituted with 2 C-C alkyl or asil

 1 6

 Cyan group, hydroxyl group, mercapto group and c ~

 1 c selected from the group consisting of alkylthio groups 6

Substituted with the same or different 1 to 6 substituents may be an aryl group "or The “aryl moiety” such as “substituted and optionally aryloxy” is, for example, a phenyl group, 2-, 3 or 4 methylphenol group, 2-, 3 or 4-methoxy group. Phenyl group, 2-, 3-, or 4-chlorophenyl group, 2-, 3-, or 4-fluorine group, 3-methylthiophenyl group, 3-cyanophenol group, 4-acetylaminophenyl Or a naphthyl group, preferably a phenyl group, a 2-, 3-, or 4-chlorophenol group, a 2-, 3-, or 4-fluorophenol group, or a 3-cyanophenol group, particularly preferably Is a phenyl group or a 3- or 4-fluorophenol group.

[0030] In the present invention, a group force consisting of a "norogen atom, a C-C alkyl group, a C-C alkoxy group, and a hydroxyl group force" such as R ¹ is selected with the same or different 1 to 6 substituents selected. “Heteroaryl moiety” such as “substituted, heteroaryl group” or “substituted, heteroaryloxy group” includes, for example, 2 pyridyl group, 3 pyridyl group, 4 pyridyl group Group, 5-methyl-2-pyridyl group, 3-isoxazolyl group, 5-isoxazolyl group, 5-methyl-3-isoxazolyl group, 4 pyrazolyl group, 5-pyrazolyl group, 2 furyl group, 3 furyl group, 3 thiazolyl group, 1 triazolyl group, 3 chael group, 3 isothiazolyl group, 2-oxazolyl group or 2-virazyl group, preferably 2 pyridyl group, 3 pyridyl group, 3 isoxazolyl group, 5 An isoxazolyl group, 5-methyl-3isoxazolyl group, 4 pyrazolyl group, 5 pyrazolyl group, 2 furyl group, 3 furyl group, 3 thiazolyl group, 3 cenyl group, 2-oxazolyl group or 2 birazyl group, particularly preferably 2 pyridyl group, 3 pyridyl group, 2 furyl group, 3 furyl group, 3-thiazolyl group or 3-chael group.

[0031] In the present invention, a "norogen atom such as R ¹ , a C to C alkyl group which may be substituted with the same or different 1 to 3 halogen atoms, a C to C alkoxy group, the same or different 1

 1 6 1 6

 Amino group, nitro group, optionally substituted with 2 C-C alkyl or asil

 1 6

 Selected from the group consisting of cyano group, hydroxyl group, mercapto group and c alkylthio group

 1 to c

 6

An “aralkyl moiety” such as an aralkyl group ”substituted with the same or different 1 to 6 substituents, or an“ aralkyl moiety ”such as an“ aralkyloxy group ”may be an aralkyl group. In the case where has a substituent, the substituent may be substituted on either or both of the aryl ring and the alkyl group constituting the aralkyl group. Nyl group, 1 phenethyl group, 2 phenethyl group, 3 phenylpropyl group, 2-, 3- or 4-methylbenzyl group, 2-, 3- or 4-methoxybenzyl group, 2-, 3- or 4 It can be a benzyl group, a 2-, 3-, or 4-fluorinated benzyl group, a 3 cyanobenzyl group, a 4 dimethylaminobenzyl group, or a 4 acetylaminobenzyl group, preferably a benzyl group, 2 phenethyl group, or 2 —, 3 or 4 Fluorobenzyl group.

 [0032] One to four X can be substituted at any substitutable position on the A ring.

[0033] Y may be substituted at 1 to 6 substitutable positions on the pyridine ring condensed with the B ring.

[0034] In the compound (I) of the present invention,

 (1) Ring A is preferably an optionally substituted benzene ring, C-C cycloalkyl

 5 6

 A ring or a pyridine ring,

 (2) Ring A is more preferably an optionally substituted benzene ring or pyridine ring,

 (3) Ring A is more preferably an optionally substituted benzene ring,

 [0036] (4) Ring B is preferably an optionally substituted benzene ring, thiophene ring, oxazole ring, thiazole ring, pyridine ring, pyrazine ring, oxazine ring, dihydrooxazine ring.

, A cyclopentane ring or a cyclohexane ring,

 [0037] (5) Ring B is more preferably an optionally substituted benzene ring, pyridine ring or dihydroxazine ring.

 On the other hand, ring B is more preferably a benzene ring or a pyridine ring which may be substituted,

[0038] (6) R \ R ² , R ³ and R ⁴ are preferably a hydrogen atom; a halogen atom; optionally substituted by 1 to 3 halogen atoms, which are the same or different, C to C Alkyl group; hydroxyl group; C to

 1 6 1

C alkoxy group; c-c alkylthio group; c-c alkylsulfier group; c-c

6 1 4 1 4 1 4 Alkylsulfonyl group; C to C cycloalkyl group; C to C cycloalkyloxy group; C

 3 6 5 6

 -C cycloalkylthio group; C-C alkenyl group; C-C alkoxy group; C

5 6 2 6 2 6 2

-C alkylthio group; c-c alkyl group; c-c alkyloxy group; c-c An alkylthio group; a C 1 -C alkyl group, a C 1 -C alkoxy group, the same or different, optionally substituted by a halogen atom, the same or different 1 to 3 halogen atoms

 1 4 1 4

An amino group optionally substituted with 1 to 2 C 1 -C alkyl or acetyl,

 1 2

Selected from the group consisting of a tro group, a cyano group, a hydroxyl group, a mercapto group, and a c to c alkylthio group.

 14

A phenyl group or a naphthyl group, which may be substituted with the same or different 1 to 3 substituents; a nitrogen atom, a C to C alkyl group, a C to C alkoxy group and a C to

 1 4 1 4 1

C alkylthio group force can also be selected with the same or different 1 to 3 substituents

Four

Optionally substituted phenoxy group; neurogen atom, c-c alkyl group, c-c al

 1 4 1 4 Coxy group and c to C alkylthio group power Group power chosen Same or different 1

 14

 A phenylthio group optionally substituted by 3 substituents; a neurogenic atom, a C-C al

 1 4 Kill group and C to C alkoxy group force Group force Selected Same or different 1 to 3

 14

Furyl group, cenyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, pyridyl group, viridyl group or pyridazyl group, which may be substituted with one substituent; c to c alkyl group and c to c

 1 4 1 4 Lucoxy group power Group power chosen Furyloxy group, ceroxy group or pyridyloxy group optionally substituted by 1 to 3 identical or different substituents; C alkyl group and C to C alkoxy group power Group power

1 4 1 4

Or substituted with 1 to 3 different substituents, furylthio, chertthio or pyridylthio; substituted with a norogen atom, 1 to 3 different halogen atoms C-C alkyl group, C-C alkoxy group, same or different

 1 4 1 4

1 to 2 C 1 -C alkyl or acetyl substituted amino groups,

 1 2

Selected from the group consisting of a tro group, a cyano group, a hydroxyl group, a mercapto group, and a c to c alkylthio group.

 14

A benzyl group, a phenethyl group, a diphenylmethyl group or a naphthylmethyl group, which may be substituted with the same or different 1 to 3 substituents;

 14 Alkyl group, c-c alkoxy group and c-c alkylthio group

 1 4 1 4

A benzyloxy group or a phenethyloxy group which may be substituted with the same or different 1 to 3 substituents; a nitrogen atom, a C 1 -C alkyl group, a C 1 -C alkoxy

 1 4 1 4

Group and C-C alkylthio group forces are also selected the same or different 1-3 Benzylthio group or phenethylthio group; formyl group, c-c alkyl carbonyl group, c-c alkenyl carboxyl group, benzoyl

2 7 3 7

Group, naphthoyl group, c to c alkoxycarbo group, c to c alkylthiocarbole

 2 7 2 5

Group or C 1 -C alkylaminocarbol group; C 1 -C alkylcarboloxy group, C

 2 7 2 5

 ~ C alkoxycarboxoxy group or c ~ c alkylaminocarboxoxy group

2 7 2 7

 C to C alkylcarbothio group, C to C alkoxycarbothio group or C to

2 5 2 5 2

A C alkylaminocarbothio group; or a force that is a cyano group, or

 Five

Rukill

Group, c to c alkoxy group and phenoxy group power is the same or different selected

14

Or form a C 1 -C cycloalkyl ring optionally substituted with 1 to 3 substituents

 3 6

Or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent a methylene group Or R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ forces together to represent a single bond,

(7) R ² , R ³ and R ⁴ are more preferably a hydrogen atom; a halogen atom; a C 1 -C alkyl group optionally substituted with 1 to 3 identical or different halogen atoms; a hydroxyl group C

 1 6

 -C alkoxy group; C -C alkylthio group; C -C alkylsulfier group; C-

1 4 1 2 1 2 1

C alkylsulfol group; C to C cycloalkyl group; C to C alkyl group; C to C

2 3 6 2 4 2 4 Alkyl group; group consisting of a norogen atom, a C to C alkyl group and a C to C alkoxy group optionally substituted by the same or different 1 to 3 halogen atoms To be elected

 1 2 1 2

Substituted with 1 to 3 substituents which may be the same or different, a phenyl group or a naphthyl group; a group consisting of a norogen atom, a C to C alkyl group and a C to C alkoxy group

 1 2 1 2

Substituted with the same or different 1 to 3 substituents selected from: a phenoxy group; selected from the group consisting of a nonogen atom, a C to C alkyl group and a C to C alkoxy;

 1 2 1 2

May be substituted with 1 to 3 substituents of the same or different, and may be a phenol group; a halogen atom, a C to C alkyl group, and a C to C alkoxy group.

 1 2 1 2

A furyl group, a cetyl group, or a pyridyl group, which may be substituted with one or different 1 to 3 substituents; a furyloxy group, a ceroxy group, or a pyridyloxy group; a frynylthio group, a benzylthio group, or a pyridylthio group. ; Halogen atom, same or different 1 C 3 -C alkyl group optionally substituted with 3 halogen atoms and C 3 -C alcohol

 1 2 1 2 Xy group power Group power chosen Benzyl group or phenethyl group, optionally substituted with the same or different 1 to 3 substituents selected; a nitrogen atom, a C to C alkyl group and C

 1 2

 ~ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents

1 2

Optionally substituted benzyloxy group; neurogen atom, c-C alkyl group and C

 1 2 1

~ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents

2

Optionally substituted benzylthio group; formyl group, C 1 -C alkylcarbonyl group,

 twenty five

c to c alkoxycarbonyl group or c to c alkylaminocarbonyl group; c to c

2 5 2 5 2 3 alkylcarbonyloxy group, c-c alkoxycarbonyloxy group or c-c al

 2 3 2 3 Killaminocarbonyloxy group; c to c alkylcarbonylthio group, c to c alkoxy

 2 3 2 3 is a cyclohexylthio group or a c to c alkylamino carbonylthio group; or a cyano group.

 twenty three

Or

Alkyl

Group force that can also be a group and C to C alkoxy group force same or different one to three selected

 1 2

A cage forming a C 1 -C cycloalkyl ring optionally substituted with a substituent, or R ¹ and R ² ;

 3 6

Or R ³ and R ⁴ forces together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent a methylene group, or R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ forces together to represent a single bond,

R ² , R ³ and R ⁴ are even more preferably substituted with 1 to 3 substituents of the same or different selected from a group consisting of a hydrogen atom; a halogen atom; a fluorine atom, a chlorine atom and a bromine atomic energy. An optionally substituted C to C alkyl group; a hydroxyl group; a methoxy group; a methylthio group;

 14

Methanesulfinyl group; methanesulfonyl group; c to c cycloalkyl group; c to c alkke

 3 6 2 3

C-c alkynyl group; fluorine atom, chlorine atom, methyl group and methoxy group

 twenty three

The group force may also be selected from the same or different substituents optionally substituted with 1 to 3 substituents.

-Group; phenoxy group; phenol thio group; furyl group, chael group or pyridyl group; fluorine atom, chlorine atom, methyl group and methoxy group power group force selected same or different

Substituted with 1 to 3 substituents !, may! /, Benzyl group; benzyloxy group; benzylthio group; formyl group, C 1 -C alkyl carbo yl group, C 1 -C alkoxy carbo yl Group or c to c alkylaminocarbol group; acetyloxy group, c to c alkoxy force

2 3 2 3

 A l-loxy group or a c-c alkylaminocarbo-loxy group; an acetyl group;

 twenty three

 Or a force that is a cyano group or

Form cycloalkyl ring

Or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ⁴ forces together, to form a methylene group. R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ forces together to represent a single bond,

[0041] Le Siku

 Forming a mouth alkyl ring,

On the other hand, Archi

 And

R ² , R ³ and R ⁴ are most preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group or an ethyl group, or ^{two of} R ¹ R ² , R ³ and R ⁴ Together, they form a cyclobutyl ring, a cyclopentyl ring or a cyclohexyl ring,

[0042] (11) Q is preferably a nitrogen atom (—N =) or a formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom; a hydroxyl group; the same or different one or two Of C to C alkyl or acetyl

 1 2

 An optionally substituted amino group, halogen atom, c to c alkoxy group and phenoxy group;

 1 2

 Group power also may be substituted with the same or different 1 to 3 selected substituents, consisting of a C 1 to C alkyl group; a nitrogen atom, a C 1 to C alkoxy group and a phenoxy group

1 4 1 2

 Group power may also be substituted with the same or different 1 to 3 substituents selected C ~

 1

C alkoxy group; fluorine atom, chlorine atom and c to c alkoxy group force

4 1 2

 C 1 -C alkyls optionally substituted with 1 to 3 identical or different substituents

 1 2 Rufyl group; fluorine atom, chlorine atom, and c to c alkoxy group force is selected

 1 2

 C 1 -C alkyl group which may be substituted with 1 to 3 identical or different substituents

 1 2

 Phonyl group; fluorine atom, chlorine atom and c to c alkoxy group force

 1 2

 Or a C 1 -C alkyl sulfa optionally substituted with 1 to 3 different substituents

 1 2

Moyl group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group C to C alkaryl optionally substituted with 1 to 3 identical or different substituents

 twenty four

Xyl group; group power that is also composed of a norogen atom, a C to C alkoxy group and a phenoxy group

 1 2

C 1 -C 3 alkyloxy may be substituted with one or different 1 to 3 substituents

 twenty four

A group; a norogen atom, substituted with 1-3 identical or different halogens, C-C alkyl groups, C-C alkoxy groups, identical or different 1-2 C-C

1 2 1 2 1 2 Amino group optionally substituted with alkyl or acetyl group, nitro group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group

 1 2

A benzyl group or a phenethyl group optionally substituted with 1 to 3 substituents; a nitrogen atom, optionally substituted with 1 to 3 different halogens C 1 to C

 1 2 alkyl group, C to C alkoxy group, same or different 1 to 2 C to C alkyl

 1 2 1 2 or an amino group optionally substituted with acetyl, amino group, nitro group, cyano group, hydroxyl group, mercapto group, and c-C alkylthio group group power is the same or different 1

 1 2

 Substituted with ~ 3 substituents! /, May! /, Benzyloxy group or phenethyloxy group

Formyl group, c-c alkylcarbonyl group, c-c alkenylcarbonyl group, ben

 2 5 3 5

Zoyl group, naphthoyl group, c-c alkoxycarbonyl group, c-c alkylthiocar

 2 5 2 5

Bonyl group or c to c alkylaminocarbonyl group; formyloxy group, c to c alkyl

 2 5 2 5 rucarbonyloxy group, c to c alkenylcarbonyloxy group, benzoyloxy

 3 5

Group, naphthoyloxy group, c-c alkoxycarbonyloxy group, c-c alkylthio group

 2 5 2 5 -carbonyloxy group or c -c alkylaminocarbonyloxy group; tree (c -c

 2 5 1 alkyl) silyl group; or di- (c-calkoxy) phosphoryl group),

4 1 2

(12) Q is more preferably a nitrogen atom (one N =) or a formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom; a hydroxyl group; a halogen atom and a C to C alkoxy group force) Power chosen

 1 2

A C 1 -C alkyl group optionally substituted with 1 to 3 identical or different substituents;

 14

Halogen atom and c to c alkoxy group force Group force Selected Same or different

 1 2

A C 1 -C alkoxy group optionally substituted with 1 to 3 substituents;

 14

 C-C alkoxy group power also has the same or different 1 to 3 substituents selected

1 2

Optionally substituted c to c alkenyloxy group; a norogen atom and c to c alcohol

2 4 1 2 Key Force Group Force Substituted with the same or different 1 to 3 selected substituents C to C alkyloxy group; a norogen atom, 1 to 3 identical or different

twenty four

Consisting of a c to c alkyl group and a c to c alkoxy group optionally substituted with a rogen

 1 2 1 2

Benzyl group which may be substituted with the same or different 1 to 3 substituents which are also selected as a group force; Norogen atom, optionally substituted with 1 to 3 different halogens C to C Group power consisting of alkyl group and C to C alkoxy group

1 2 1 2

May be substituted with 1 to 3 different substituents, and may be a benzyloxy group; a formyl group, a c to c alkyl carbo group, a benzoyl group, a c to c alkoxy carbo group or

2 5 2 5

c to c alkylaminocarbo group; or formyloxy group, c to c alkylcarbo group

2 5 2 5

 -Luoxy group, Benzyloxy group, C to C alkoxycarboxoxy group or C

 2 5 2

~ C alkylaminocarbo-loxy group),

 Five

(13) Q is still more preferably a nitrogen atom (one N =) or a formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom; a hydroxyl group; a fluorine atom, a chlorine atom and a bromine nuclear atom) Force C 1 -C alkyl group optionally substituted with 1 to 3 identical or different substituents selected;

 14

Elementary force, chlorine atom and bromine atomic energy are selected C 1 -C alkoxy group optionally substituted by 1 to 3 identical or different substituents; C 1 -C alkoxyloxy

 1 4 2 4

A group c to c alkyloxy group; a group consisting of a fluorine atom, a chlorine atom, fluorine and chlorine;

twenty four

C to C may be substituted with the same or different 1 to 3 substituents selected from

 1 2 Alkyl group and c to C alkoxy group force Group force selected Same or different 1

 1 2

 Benzyl group optionally substituted by 3 substituents; group power consisting of fluorine atom, chlorine atom, fluorine and chlorine, optionally substituted by 1 to 3 identical or different substituents The same selected from the group consisting of a good C to C alkyl group and a C to C alkoxy group

 1 2 1 2

Or substituted with 1 to 3 different substituents, which may be a benzyloxy group;

 2

C alkylcarbonyl group, c-c alkoxycarbonyl group or c-c alkylamino

5 2 5 2 5

No-carbonyl group; or c-c alkylcarbonyloxy group, c-c alkoxycal

 2 5 2 5

A bonyloxy group or a c to c alkylaminocarbonyloxy group),

 twenty five

(14) Q is still more preferably a nitrogen atom (one N =) or a formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom; a hydroxyl group; a fluorine atom and a chlorine atom group force). A C 1 -C alkyl group which may be substituted with the same or different 1 to 3 selected substituents; a fluorine atom And a group power of chlorine nuclear power, which may be substituted with 1 to 3 identical or different substituents selected from C to C alkoxy groups; aryloxy groups; propargyloxy groups;

 1 2

 Elementary force, chlorine atom, methyl group, and methoxy group power group force selected benzyl group optionally substituted by 1 to 3 identical or different substituents; fluorine atom, chlorine atom, methyl group, and methoxy group Basic power Group power Benzyloxy group optionally substituted by the same or different 1 to 3 substituents selected; acetyl group, methoxycarbol group, ethoxycarboro group or methylaminocarbole A group; or an acetyloxy group, a methoxycarboxoxy group, an ethoxycarboxoxy group, or a methylaminocarboxoxy group),

On the other hand, Q is still more preferably represented by the formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom, a c to c alkyl carbo group, a c to c alkoxy carbo group, c to c alkyl

2 5 2 5 2 5 is an aminocarbonyl group or a c to c alkyl group),

 14

(15) Q is particularly preferably a nitrogen atom (one N =) or a formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom, a hydroxyl group, a methyl group, an ethyl group, a methoxy group, A group, an ethoxy group, an aryloxy group, a propargyloxy group, a benzyl group, a benzyloxy group, an acetyl group, a methoxy carbo yl group, an ethoxy carbo ol group, an acetyl oxy group, a methoxy carbo oxy oxy group or an ethoxy carbo oxy oxy group). And

On the other hand, Q is particularly preferably a formula = N—R ⁵ group (wherein R ⁵ is a hydrogen atom, a acetyl group, a C to C alkoxycarbo group or a methyl group),

 twenty three

[0045] (16) Q is Most preferably, the nitrogen atom (- N =) or formula = N-R ⁵ group (wherein, R ⁵ is water atom, a hydroxyl group, a methyl group, Echiru group, methoxy A group, an ethoxy group, a acetyl group, a methoxy carbo group, an ethoxy carbo group, an acetyl group, a methoxy carboxy group or an ethoxy carbo oxy group).

 (17) X is preferably an X force halogen atom; a C to C alkyl group which may be substituted with the same or different 1 to 3 substituents which are also selected as a group force consisting of a halogen nuclear atom;

 14

 Elementary atom and chlorine nuclear power Group power C-C cycloalkyl group optionally substituted with 1 to 3 identical or different substituents selected;

 3 6

Group power selected by the same or different selected 1 to 3 substituents, C ~ Calkell group; fluorine atom and chlorine nuclear power group power selected same or different

Four

A C to C alkyl group optionally substituted with 1 to 3 substituents; a fluorine atom, a salt

 twenty four

Elementary force, bromine atom, fluorine and chlorine force Group force C-C alkyl group, C-C alkoxy group, same group which may be substituted with the same or different 1 to 3 substituents selected

 1 4 1 4

May be substituted with one or different 1-2 C-C alkyl or acetyl

 1 2

Good amino group, nitro group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group

 1 2

Force group power Force group that is optionally substituted with 1 to 3 substituents that may be substituted, such as a phenyl group or naphthyl group; fluorine atom, chlorine atom, bromine atom, fluorine, and chlorine force Group power consisting of C to C alkyl group and C to C alkoxy group which may be substituted with 1 to 3 identical or different substituents.

1 4 1 4

May be substituted with 1 to 3 different substituents, such as furyl, chenyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyridyl, birazyl, or Pyridazyl group; a group power that is also a halogen nuclear energy. C-C alkoxy optionally substituted with 1 to 3 identical or different substituents.

 1 4 Si group; halogen atoms may be substituted with the same or different 1 to 3 substituents selected from C to C alkylthio groups; fluorine atom and chlorine atom group

 14

Optionally substituted with 1 to 3 identical or different substituents selected

 1 2 ruylsulfier group; group power of fluorine atom and chlorine nuclear power, a C to C alkylsulfonyl group which may be substituted with the same or different 1 to 3 selected substituents;

 1 2

Substituted with one or different 1-2 C-C alkyl or acetyl groups

 1 2

Moyamino group; formyl group, c-c alkyl carbo group, benzoyl group, c-c a

 2 5 2 5 alkoxy group or C to C alkylaminocarbol group; cyan group; or C to C

 2 5 1

C alkyl group, c-c alkyl group, c-c alkyl group, phenol group, naphthyl

4 2 4 2 4

Group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, pyridyl group, virazyl group or pyridazyl group N-Hydroxy (C to C alkane) imidoyl group, n force 0 to 3,

 14

On the other hand, X is preferably an X force halogen atom; C to C alkyl optionally substituted with 1 to 3 identical or different substituents

 1 4 group; c to c cycloalkyl group; c to c alkenyl group; c to c alkynyl group; fluorine atom

3 6 2 4 2 4

 , Chlorine atom, bromine atom, C-C alkyl group, C-C alkoxy group, 1-2 C-C

 1 2 1 2 1 Amino group, acetylamino group, nitro group, cyano group, water optionally substituted with alkyl

2

 Acid group, mercapto group, and c-c alkylthio group group forces that are the same or selected

 1 2

 Substituted with 1 to 3 different substituents may be a phenol group; a fluorine atom, a chlorine atom, a methyl group, and a methoxy group force. The same or different 1 to 2 positions selected Furyl, chael or pyridyl, optionally substituted by a substituent; C to C alcohol

 1 2 C-C alkoxy group optionally substituted with a xy group; C-C alkylthio group; C-

 1 2 1 2 1

C alkyl sulfier group; C to C alkyl sulfol group; 1 to 2 C to C alkyls

2 1 2 1 2 Amino group or acetylamino group optionally substituted with a group; formyl group, c to

 2 c Al 7 Kill carbo yl group, c to alkoxy carbo ol group or al

 2 c 7 c ~

 2 c Killaminocal 7

 A ball group; a cyan group; or a c to c alkyl group,

 1 4 c ~

 3 carbonyl group,

 4 c ~

 3c alk 4

A hydrogen atom of a hydroxyl group may be substituted with a substituent selected from the group consisting of a-group, a phenyl group, a naphthyl group, a furyl group, a chael group, and a pyridyl group; C

 1

~ C) alkaneimidoyl group, n force 0-3,

 Four

 [0046] (18) X is more preferably X is a halogen atom; a fluorine atom, a chlorine atom, and a bromine atomic force, or a group force that is the same or different and selected from 1 to 3 substituents. C to C alkyl group; C to C cycloalkyl group; fluorine atom, chlorine atom, bromine atom

1 4 5 6

 Or the same or a group selected from the group consisting of a c-c alkyl group and a c-c alkoxy group

1 2 1 2

 May be substituted with 1 to 3 different substituents, including a phenyl group; a furyl group, a chael group or a pyridyl group; a C to C alkoxy group; and 1 to 2 C to C alkyl groups. Replaced

 1 2 1 2

 An amino group or an acetylamino group which may be present;

 2 c

 3 c ~

 2 c 3 alkoxy group or C to C alkylaminocarbol group; cyan group; or C to C

 2 3 1

A hydrogen atom of a hydroxyl group with a substituent selected from the group consisting of a C alkyl group and a phenyl group

2

 Is an optionally substituted N-hydroxy- (C-C) alkaneimidoyl group, and n is

 1 2

 0-2

[0047] (19) X is even more preferably composed of X force halogen atom; fluorine atom and chlorine atom. Group power selected by the same or different selected 1 to 3 substituents, C

 1

~ C alkyl group; selected from the group consisting of fluorine atom, chlorine atom, methyl group and methoxy group

Four

Substituted with 1 to 3 identical or different substituents, which may be a phenyl group; C

 1

~ C alkoxy group; or group power that also has methyl group and ethyl group power

2

N-hydroxy- (C to C) alkaneimido, in which the hydrogen atom of the acid group may be substituted

 1 2

N is 0 to 2,

 (20) X is particularly preferably an X force halogen atom or a C to C alkyl group, and n is n 14

 0-2

 (21) X is most preferably X force is a fluorine atom, a chlorine atom or a methyl group, n is 0 to 2,

(22) Y is preferably a repulsive halogen atom; a C to C alkyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of no and rogen atoms; Fluor

 14

Elementary atom and chlorine nuclear power Group power C-C cycloalkyl group optionally substituted with 1 to 3 identical or different substituents selected;

 3 6

Group power selected by the same or different selected 1 to 3 substituents, C

 2

~ C alkell group; fluorine atom and chlorine nuclear power group selected same or different

Four

A C to C alkyl group optionally substituted with 1 to 3 substituents; a fluorine atom, a salt

 twenty four

Elementary force, bromine atom, fluorine and chlorine force Group force C-C alkyl group, C-C alkoxy group, same group which may be substituted with the same or different 1 to 3 substituents selected

 1 4 1 4

May be substituted with one or different 1-2 C-C alkyl or acetyl

 1 2

Good amino group, nitro group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group

 1 2

Force group power Force group that is optionally substituted with 1 to 3 substituents that may be substituted, such as a phenyl group or naphthyl group; fluorine atom, chlorine atom, bromine atom, fluorine, and chlorine force Group power consisting of C to C alkyl group and C to C alkoxy group which may be substituted with 1 to 3 identical or different substituents.

1 4 1 4

Is optionally substituted with 1 to 3 different substituents, such as furyl, chenyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyridyl, birazyl, or Pyridazyl group; halogen nuclear power also selected C to C alkoxy optionally substituted with 1 to 3 identical or different substituents

 14 Si group; halogen power may be selected by the same or different 1 to 3 substituents that may be selected. C to C alkylthio group; fluorine atom and chlorine atom

 14

C to C may be substituted with the same or different 1 to 3 substituents that are also selected

 1 2 alkylsulfinyl group; fluorine atom and chlorine nuclear power group power selected C 1 to C alkylsulfol group optionally substituted with 1 to 3 different substituents selected;

 1 2

Substituted with the same or different 1 to 2 C-C alkyl group or acetyl group.

 1 2

Molyamino group; formyl group, c-c alkyl carbonyl group, benzoyl group, c-c

 2 5 2 5 Alkoxycarbon group or c to c alkylaminocarbol group; Cyan group; or water

 twenty five

An acid group, m force 0-5,

On the other hand, Y is preferably a Y-force halogen atom; a C-C alkyl which may be substituted with the same or different 1 to 3 substituents which are also selected as a group force consisting of a halogen nuclear power.

 1 4 group; c to c cycloalkyl group; c to c alkenyl group; c to c alkynyl group; fluorine atom

3 6 2 4 2 4

 , Chlorine atom, bromine atom, C-C alkyl group, C-C alkoxy group, 1-2 C-C

 1 2 1 2 1 Amino group, acetylamino group, nitro group, cyano group, water optionally substituted with alkyl

2

Acid group, mercapto group, and c-c alkylthio group group forces that are the same or selected

 1 2

Substituted with 1 to 3 different substituents may be a phenol group; a fluorine atom, a chlorine atom, a methyl group, and a methoxy group force. The same or different 1 to 2 positions selected Furyl, chael or pyridyl, optionally substituted by a substituent; C to C alcohol

 1 2 C-C alkoxy group optionally substituted with a xy group; C-C alkylthio group; C-

 1 2 1 2 1

C alkyl sulfier group; C to C alkyl sulfol group; 1 to 2 C to C alkyls

2 1 2 1 2 amino group or acetylamino group optionally substituted with a group; formyl group, c to c al

 2 7 Kill carbo group, c-c alkoxy carbo group or c-c alkylamino carbo group

 2 7 2 7 Bonyl group; Cyan group; or Hydroxyl group, m force 0-5,

(23) In Y, more preferably, Υ may be substituted with 1 to 3 substituents, which are the same or different, selected from a halogen atom, a fluorine atom, a chlorine atom, and a bromine atomic force. C to C alkyl group; C to C cycloalkyl group; fluorine atom, chlorine atom, bromine atom

1 4 5 6

Or the same or a group selected from the group consisting of a c-c alkyl group and a c-c alkoxy group May be substituted with 1 to 3 different substituents, including a phenyl group; a furyl group, a chael group or a pyridyl group; a C to C alkoxy group; and 1 to 2 C to C alkyl groups. Replaced

 1 2 1 2

 Optionally an amino group or an acetylamino group; a c to c alkyl carbo group,

 2 3 c ~

 2 c 3 Lucoxycarbo group or c ~

 2c alkylaminocarbol group; cyano group; or hydroxy acid 3

 A group, m is 0-2,

[0050] (24) Y is even more preferably substituted with 1 to 3 substituents selected from the same or different Y force halogen atom; a group force consisting of a fluorine atom and a chlorine atom. Yo, C

 1

~ C4 alkyl group; substituted with 1 to 3 identical or different substituents selected from the group consisting of fluorine atom, chlorine atom, methyl group and methoxy group; Or a C to C alkoxy group, n force 0 to 2,

 1 2

 (25) Y is particularly preferably a Y force halogen atom or a C to C alkyl group, and m is m 14.

 0-2

 (26) Y is most preferably a repulsive fluorine atom, a chlorine atom or a methyl group, and an m force of 0 to 2.

 [0051] The compound (I) of the present invention can be converted to a salt such as sulfate, hydrochloride, nitrate or phosphate. These salts are included in the present invention as long as they can be used as agrochemical compositions (agricultural and horticultural fungicides).

[0052] The compound (I) of the present invention can be solvated, and these solvates are also encompassed in the present invention. Such solvates are preferably hydrates.

[0053] The compound (I) of the present invention includes a compound having an asymmetric carbon. In this case, the present invention contains one kind of optically active substance and several kinds of optically active substances in an arbitrary ratio. Also included is a mixture.

 [0054] Representative compounds of the present invention are exemplified in the following table, but the present invention is not limited to these compounds.

[0055] Hereinafter, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Vinyl” represents a bur group, “Allyl” represents an aryl group, and “Ethynyl” represents an ethul group. `` Ph '' is a phenyl group, `` Ac '' is a acetyl group, `` MeMeIMD '' is an N-methoxymethanimidyl group, `` Pyr '' is a pyridyl group, `` Bn '' is a benzyl group, `` CPr '' is cyclopropyl group, `` cBu '' is cyclo A butyl group, “cPen” represents a cyclopentyl group, “cHex” represents a cyclohexyl group, and in “Xn” and “Ym”, Xn represents “5-PYR”, “6-PYR”. ”,“ 5-T ΗΙ ”and“ 6—ΤΗΙ ”, the rings で are 5-pyridyl ring, 6-pyridyl ring, 5-chael ring and 6-chael ring, respectively. , All of the substituents (Xn) are hydrogen atoms, and Xn force indicates a group other than the above, ring A is a benzene ring, the substituent is Xn itself, and Ym is `` 6 — PYR ”,“ 7—PYR ”,“ 8—PYR ”,“ 5, 8—PRA ”,“ 5, 7—OXZO ”,“ 5, 7—THA ”,“ 3H—5, 8—OXZN ”, When “c—Pen” and “c Hex” are indicated, ring B is 6-pyridyl ring, 7-pyridyl ring, 8-pyridyl ring, 5 (nitrogen), 8 (nitrogen) -pyrazine ring, 5 (Oxygen), 7 (Nitrogen) Oxazol Ring, 5 (sulfur), 7- (nitrogen) thiazole ring, 6, 7-dihydro-8H-5 (oxygen), 8- (nitrogen) monooxazine ring, cyclopentane ring and cyclohexane ring, substitution All the groups (Ym) are hydrogen atoms, and when Ym represents a group other than the above, ring B is a benzene ring and the substituent is Ym itself.

Compound number R3, R4 R1, R2 Xn Ym

1-1 H, H H, H H H

1-2 H, H H, H H 4-F

1-3 H, H H, H H 8-F

1-4 H, H H, H H 4-CI

1-5 H, H H, H H 6- CI

1-6 H, H H, H H 4-MeO

1-7 H, H H, H H 8-Me

1-8 H, H H, H H 8-MeO

1-9 H, H H, H H 8-OH

1-10 H, H H, H 5-F H

1-11 H, H H, H 5-F 4-F

1-12 H, H H, H 5-F 8-F

1-13 H, H H, H 5-F 4-CI

1-14 H, H H, H 5-F 6-CI

1-15 H, H H, H 5-F 4-MeO

1-16 H, H H, H 5-F 8-Me

1-17 H, H H, H 5-F 8-MeO

1-18 H, H H, H 5-F 8-OH

1-19 H, H H, H 5-F 8-cPr

1-20 H, H H, H 5-F 8-CF3

1-21 H, H H, H 5-F 8-Vinyl

1-22 H, H H, H 5-F 8-Etynyl

1-23 H, H H, H 5-F 4-P

1-24 H, H H, H 5-F 4-Pyr

1-25 H, H H, H 5-F 4-MeS

1-26 H, H H, H 5-F 4- MeSO

1-27 H, H H, H 5-F 4-MeS02

1-28 H, H H, H 5-F 4-MeNH

1-29 H, H H, H 5-F 8- Ac

1-30 H, H H, H 5-F 8-CN

1-31 H, H H, H 6-F H

1-32 H, H H, H 7-F H

1-33 H, H H, H 8-F H

1-34 H, H H, H 5,7- F2 H

1-35 H, H H, H 5-CI H

1-36 H, H H, H 6-Gl H

1-37 H, H H, H 7-CI H

1-38 H, HH _s H 5-Br H

1-39 H, H H, H 5-Me H

1-40 H, HH, H 6— Me H -41 H, HH, H 7- Me H-42 H, HH, H 5-cHex H-43 H, HH, H 5- Ally I H-44 H, HH, H 5-Etynyl H-45 H, HH , H 5- Ph H-46 H, HH, H 5- Pyr H-47 H, HH, H 6- MeO H-48 H, HH, H 6,7-(MeO) 2 H-49 H, HH, H 5-MeS H-50 H, HH, H 5-MeSO H-51 H, HH, H 5-MeS02 H-52 H, HH, H 5-MeNH H-53 H, HH, H 5-Ac H- 54 H, HH, H 5-CN H-55 HHH, H 5-MeMeIMD H-56 H, HH, Me H H-57 H, HH, Et H H-58 H, HH, Pr H H-59 H, HH, cPen H H-60 H, HH, cHex H H-61 H, HH, OH HH-62 H, HH, MeO H H-63 H, HH, MeS H H-64 H, HH, MeSO H H- 65 H, HH, MeS02 HH-66 H, HH, Vinyl H H-67 H, HH, Ph H H-68 H, HH, Pyr H H-69 H, HH, PhO HH-70 H, HH, OPyr H H-71 H, HH, Ac H H-72 H, HH, AcO HH-73 H, HH, AcS H H-74 H, HH, CN H H-75 H, HH, FH H-76 H, HH, CI HH-77 H, HH, Me 5-FH-78 H, HH, Et 5-F H-79 H, HH _s Bn 5-F H-80 H, HH, Pr 5-FH -81 H, HH, OH 5-F H-82 H, HH, MeO 5-F H-83 H, H H.Ac 5-F H-84 H, HH, AcO 5-F H-85 H, HH , AcS 5-F H-86 H, HH, CN 5-F H-87 H, HH, F 5-F H-88 H, HH, CI H H-89 H, H Me, Me H H-90 H , H Me.Et HH-91 H, H Me, OH H H-92 H, H Me, OMe H H-93 H, H Me, FH H-94 H, H Me, CI H H-95 H, HF , FH H-96 H, H 0 = H H-97 H, H CH2 = H H-98 H, H cPen H H-99 H, H cHex H H-100 H, Me H, HH H-101 H, Et H, HH H-102 H, Pr H, HH H-103 H, Bn H, HH H-104 H, cPen H, HH H-105 H, cHex H, HH H-106 H, OH H, HH H -107 H, MeO H, HH H-108 H, MeS H, HH H-109 H, MeSO H, HH H-110 H, MeS02 H, HH H-111 H, Vinyl H, HH H-112 H, Ph H, HH H-113 H, Pyr H, HH H-114 H, PhO H, HH H-115 H, OPyr H, HH H-116 H, Ac H, HH H-117 H, AcO H, HH H- 118 H, AcS H, HH H-119 H, CN H, HH H-120 H, FH, HHH -121 H, CIH, HH H-122 Me, Me H, HH H-123 H, Me H, H 5-CI H-124 Me, Me H, H 5-F H-125 Me, OH H, H 5-F H-126 Me, OMe H, H 5-F H-127 Me, FH, H 5-F H-128 Me, CI H, H 5-F H-129 H, Me H, H 5- F H-130 H, Me H, Me 5-F H-131 H, Me H, Et 5-F H-132 H, Me H, Pr 5-F H-133 H, Me H, Me 5-CI H -134 Me, Me H, Me 5-F H-135 H, Et H, Me 5-F H-136 H, Pr H, Me 5-F H-137 H, Ph H, Me 5-F H-138 Me, Me H, Et 5-F H-139 Me, Me H, Pr 5-F H-140 Me, Me H, cPen 5-F H-141 Me, Me H, cHex 5-F H-142 Me, Me H, OH 5-F H-143 Me, Me H, MeO 5-F H-144 Me, Me H, MeS 5-F H-145 Me, Me H, MeSO 5-F H-146 Me, Me H , MeS02 5-F H-147 Me, Me H, Vinyl 5-F H-148 Me, Me H, Ph 5-F H-149 Me, Me H, Pyr 5-F H-150 Me, Me H, PhO 5-F H-151 Me, Me H, OPyr 5-F H-152 Me, Me H, Ac 5-F H-153 Me, Me H, AcO 5-F H-154 Me, Me H, AcS 5- F H-155 Me, Me H, CN 5-F H-156 Me, Me H, F 5-F H-157 Me, Me H, CI 5-F H-158 Me, Et H HH H-159 Me, Pr H, HH H-160 e, cPen H, HH H-161 Me Bn H, HH H-162 Me, Ph H, HH H-163 Me, Pyr H, HH H-164 Me, CF3 H, HH H-165 H, H Me, Me HH -166 H, H cPr H H-167 H, H cBu H H-168 H, H cPen H H-169 H, H cHex H H-170 H, H Me, Me 5-F H-171 H, H cPr 5-F H-172 H, H cBu 5-F H-173 H, H cPen 5-F H-174 H, H cHex 5-F H-175 H, Me Me, Me 5-F H-176 H, Me Me, Me H H-177 H, Et Me, Me 5-F H-178 H, OMe Me, Me 5-F H-179 Me, Et Me, Me 5-F H-180 Me, Pr Me, Me H H-181 Me, cPen Me, Me H H-182 Me, Bn Me, Me H H-183 Me, Ph Me, Me H H-184 Me, Pyr Me, Me H H-185 H, H Et, Et 5-F H-186 Me, Et F, FH H-187 Me, Pr F, FH H-188 Me cPen F, FH H-189 Me, Bn F, FH H-190 Me, Ph F, FH H-191 Me, Pyr F, FH H-192 Me, CF3 F, FH H-193 cPen H, HH H-194 cHex H, HH H-195 cPen H, H 5-F H-196 cHex H, H 5-F H -197 Me, Me Me, Me 5-F H-198 Me, Me Me, Me 5-F 2- CI-199 Me, Me Me, Me 5-F 2-OH-200 Me, Me Me, Me 5- F 2-CIJ-! \

--201 Me, Me Me, Me 5-PYR H- -202 Me, Me Me, Me 6-PYR H- -203 Me, Me Me, Me 5-THI H. -204 Me, Me Me, Me 6- THI H

-205 Me, Me Me, Me H 8-PYR.- 206 Me, Me Me, Me 5-F 7-PYR

-207 Me, Me Me, Me H 6-PYR.-208 Me, Me Me, Me H 5,8-PRA

-209 Me, Me Me, Me H 5,7-OXZO. -21 0 Me, Me Me, Me H 5,7-THA- -21 1 Me, Me Me, Me 5-F 3H- 5,8- OXZN -212 Me, Me Me, Me 5-F 8- Me- 3H- 5,8- 0: -213 Me, Me Me, Me 5-F cPen

-214 Me. Me Me, Me 5-F cHex

-21 5 Me, Me Me, Me H 3H- 5,8- OXZN

-21 6 Me, Me F, F H 3H-5,8-OXZN- -21 7 Me.Me F, F 5-F 3H-5,8-OXZN · -21 8 Me, Me F, F H H

-21 9 Me, Me F, F 5-F H

(lb)

Compound number R3 R1 Xn Ym

2-1 H H H H

2-2 H H H 4-F

2-3 H H H 8-F

2-4 H H H 4-CI

2-5 H H H 6- CI

2-6 H H H 4-MeO

2-7 H H H 8-Me

2-8 H H H 8-MeO

2-9 H H H 8-0 H

2-10 H H 5-F H

2-1 1 H H 5-F 4-F

2-12 H H 5-F 8-F

2-13 H H 5-F 4-CI

2-14 H H 5-F 6-CI

2-15 H H 5-F 4-MeO

2-16 H H 5-F 8-Me

2-17 H H 5-F 8-MeO

2-18 H H 5-F 8- OH

2-19 H H 5-F 8-cPr

2-20 H H 5-F 8-CF3

2-21 H H 5-F 8- Vinyl

2-22 H H 5-F 8-Etynyl

2-23 H H 5-F 4-Ph

2-24 H H 5-F 4-Pyr

2-25 HH 5-F 4-MeS

-26 HH 5-F 4- MeSO-27 HH 5-F 4- MeS02-28 HH 5-F 4-MeNH-29 HH 5-F 8-Ac-30 HH 5-F 8-CN-31 HH 6- FH-32 HH 7-F H-33 HH 8-F H-34 HH 5,7-F2 H-35 HH 5-CI H-36 HH 6-CI H-37 HH 7-GI H-38 HH 5- Br H-39 HH 5- Me H

 5 £ p p

-40 HH 6-Me H-41 HH 7-Me H-42 HH 5-cHex H-43 HH 5-Allyl H-44 HH 5-Etynyl H-45 HH 5-Ph H-46 HH 5-Pyr H- 47 HH 6-MeO H-48 HH 6,7-(MeO) 2 H-49 HH 5-MeS H-50 HH 5-MeSO H-51 HH 5-MeS02 H-52 HH 5-MeNH H-53 HH 5 -Ac H-54 HH 5-CN H-55 HH 5-MeMelMD H-56 HH, Me H H-57 H Et HH-58 H Pr H H-59 H cPen H H-60 H cHex H H-61 H OH H H-62 H MeO H H-63 H MeS H H-64 H MeSO H H-65 H MeS02 H H-66 HH H-67 HH H-68 HH H-69 HHH i /: / O 8 / -02Tl £ sonoz-oozAV

[99001

ェ ェ ェ ェ ェ ェ ェ ェ ェ ェ ェ

U. u_ ϋ_ U- L. LL. U_ U- ye ye ye III IT ye ye ye ye ye ye ir ^ i:

H 0 dried 2

 H

H 2 dried ε dried 2 [0067]

 2-1 14 Me Et 5-F H

2-1 15 Me Pr 5-F H

2-1 16 Me Me 5-CI H

2-1 17 Et Me 5-F H

2-1 18 Pr Me 5-F H

2-1 19 Ph Me 5-F H

2-120 Me, Me Me, Me 5-PYR H

2-121 Me, Me Me, Me 6-PYR H

2-122 Me, Me Me, Me 5-THI H

2-123 Me, Me Me, Me 6-THI H

2-124 Me, Me Me, Me H 8-PYR

 2-125 Me, Me Me, Me H 7-PYR

 2-126 Me, Me Me, Me H 6-PYR

 2-127 Me, Me Me, Me H 5,8-PRA

 2-128 Me, Me Me, Me H 5J-OXZO

 2-129 Me, Me Me, Me H 5,7-THA

 [0069]

 Compound number R3 R4 R1, R2 R5 Xn Ym

3-1 H, H H, H H H H

3-2 H, H H, H H H 4-F

3-3 H, H H, H H H 8-F

3-4 H, H H, H H H 4-CI

3-5 H, H H, H H H 6-CI

3-6 H, H H, H H H 4-MeO

3-7 H, H H, H H H 8-Me

3-8 H, H H, H H H 8-MeO

3-9 H, H H, H H H 8-OH

3-10 H, H H, H H 5-F H

3-1 1 H, H H, H H 5-F 4-F

3-12 H, H H, H H 5-F 8-F

3-13 H, H H, H H 5-F 4-CI

3-14 H, H H, H H 5-F 6-CI

3-15 H, HH, HH 5-F 4-MeO -16 H, HH, HH 5-F 8-Me-17 H, HH, HH 5-F 8-MeO-18 H, HH, HH 5-F 8- OH-19 H, HH, HH 5-F 8 -cPr-20 HHH, HH 5-F 8-CF3-21 H, HH, HH 5-F 8- Vinyl-22 H, HH, HH 5-F 8-Etynyl-23 H, HH, HH 5-F 4 -Ph-24 H, HH, HH 5-F 4-Pyr-25 H, HH, HH 5-F 4-MeS-26 H, H H. HH 5-F 4-MeSO-27 H, HH, HH 5 -F 4-MeS02-28 H, HH, HH 5-F 4-MeNH-29 H, HH, HH 5-F 8-Ac-30 H, HH, HH 5-F 8-CN-31 H, HH, HH 6-F H-32 H, HH, HH 7-F H-33 H, HH, HH 8-F H-34 H, HH, HH 5.7-F2 H-35 H, HH, HH 5-CI H- 36 H, HH, HH 6-CI H-37 H, HH, HH 7-CI H-38 H, HH, HH 5-Br H-39 H. HH, HH 5-Me H-40 H, HH, HH 6 Me H-41 H, HH, HH 7- Me H-42 H, HH, HH 5-cHex H-43 H, HH, HH 5-Allyl H-44 H, HH, HH 5-Etynyl H-45 H , HH, HH 5-Ph H-46 H, HH, HH 5-Pyr H-47 H, HH, HH 6-MeO H-48 H, HH, HH 6J- (MeO) 2 H-49 H, HH, HH 5-MeS H-50 H, HH, HH 5-MeSO H-51 H, HH, HH 5-MeS02 H-52 H, HH, HH 5-MeNH H-53 H, HH, HH 5-Ac H- 54 H, HH, HH 5-CN H-55 H, HH, HH 5-MeMeIMD H-56 H, HH, Me HH H-57 H, HH, Et HH H-58 H, HH, Pr HH H-59 H, HH, cPen HHH H, HH, cHex HH H-61 H, HH, OH HHH-62 H, HH, MeO HH H-63 H, HH, MeS HH H-64 H, HH, MeSO HH H-65 h HH, MeS02 HH H-66 H, HH, Vinyl HH H-67 H, HH, Ph HH H-68 H, HH, Pyr HH H-69 H, HH, PhO HH H-70 H, HH, OPyr HHH-71 H, HH , Ac HH H-72 H, HH, AcO HH H-73 H, HH, AcS HH H-74 H, HH, CN HHH-75 H, HH, FHH H-76 H, HH, CI HH H-77 H , HH, Me H 5-F H-78 H, HH, Et H 5-F H-79 H, H H. Bn H 5-F H-80 H, HH, Pr H 5-F H-81 H, HH, OH H 5-F H-82 H, HH, MeO H 5-FH-83 H, H H. Ac H 5-F H-84 H, HH, AcO H 5-F H-85 H, HH, AcS H 5-F H-86 H, HH, CN H 5-F H-87 H, HH, FH 5-F H-88 H, HH, CI HH H-89 H, H Me, Me HH H-90 H, H Me, Et HH H-91 H, H Me, OH HH H-92 H, H Me, OMe HH H-93 H, H Me, FHH H-94 H, H Me, CI HH H-95 H , HF, FHH H-96 H, H 0 = HH H-97 H, H CH2 = HH H-98 H, H cPen HH H-99 H, H cHex HH H-100 H, Me H, HHHH-101 H , Et H, HHH H-102 H, Pr H, HHH H-103 H, Bn H, HHHH -104 H, cPen H, HHH H-105 H, cHex H, HHH H-106 H, OH H, HHH H-107 H, MeO H, HHH H-108 H, MeS H, HHH H-109 H, MeSO H, HHH H-1 10 H, MeS02 H, HHH H-1 1 1 H, Vinyl H, HHH H-1 12 H, Ph H, HHH H-1 13 H, Pyr H, HHH H-1 14 H, P ohO H, HHH H-1 15 H, OPyr H, HHH H-1 16 H, Ac H, HHH H-1 17 H, AcO H, HHH H-1 18 H, AcS H, HHH H-1 19 H, CN H, HHH H-120 H, FH, HHH H-121 H, CI H, HHH H-122 Me, Me H, HHH H-123 H, Me H, HH 5-CI H-124 Me, Me H, HH 5-F H-125 H, HH 5-F H-126 Me, OMe H, HH 5-F H-127 Me, FH, HH 5-F H-128 Me. CI H, HH 5- F H-129 H, Me H, HH 5-F H-130 H, Me H, Me H 5-F H-131 H, Me H, Et H 5-F H-132 H, Me H, Pr H 5 -F H-133 H, Me H, Me H 5-CI H-134 Me, Me H, Me H 5-F H-135 H, Et H, Me H 5-F H-136 H, Pr H, Me H 5-F H-137 H, Ph H, Me H 5-F H-138 Me, Me H, Et H 5-F H-139 Me, Me H, Pr H 5-F H-140 Me, Me H , CPen H 5-F H-141 Me, Me H, cHex H 5-F H-142 Me, Me H, OH H 5-F H-143 Me, Me H, MeO H 5-F H-144 Me, Me H, MeS H 5-F H-145 Me, Me H, MeSO H 5-F H-146 Me, Me H, MeS02 H 5-F H-147 Me, Me H, Vinyl H 5-FH _ _{1 48} Me, Me H, Ph H 5-F H-149 Me, Me H, Pyr H 5-F H-150 Me, Me H, PhO H 5-F H-151 Me, Me H, OPyr H 5 -F H-152 Me, Me H. Ac H 5-F H-153 Me, Me H, AcO H 5-F H-154 Me, Me H, AcS H 5-F H-155 Me, Me H, CN H 5-F H-156 Me, Me H, FH 5-F H-157 Me, Me H, CI H 5-F H-158 Me, Et H, HHH H-159 Me, Pr H, HHH H-160 Me, cPen H, HHH H-161 Me _% Bn H, HHHH-162 Me, Ph H, HHH H-163 Me, Pyr H, HHH H-164 Me, CF3 H, HHH H-165 H, H Me, Me HH H-166 H, H cPr HH H-167 H, H cBu HH H-168 H, H cPen HH H-169 H, H cHex HH H-170 H, H Me, Me H 5-F H-171 H , H cPr H 5-F H-172 H, H cBu H 5-F H-173 H, H cPen H 5-F H-174 H, H cHex H 5-F H-175 H, Me Me, Me H 5-F H-176 H, Me Me, Me HH H-177 H, Et Me, Me HH H-178 H, OMe Me, Me H 5-F H-179 Me, Et Me, Me H 5-F H -180 Me, Pr Me, Me HH H-181 Me, cPen Me, Me HH H-182 Me, Bn Me, Me HH H-183 Me, Ph Me, Me HH H-184 Me, Pyr Me, Me HH H -185 H, H Et, Et H 5-F H-186 Me, Me Me, Me Me 5-F H-187 Me, Me Me, Me Et 5-F H-188 Me, Me Me, Me CICH2 5-F H-189 Me, Me Me, Me MeOCH2 5-F H-190 Me, Me Me, Me OH H H-191 Me, Me Me, Me OMe HH [0074]

 3-192 Me, Me Me, Me OH 5- CI H

3-193 Me, Me Me, Me MeSO 5-F H

3-194 Me, Me Me, Me MeS02 5-F H

3-195 Me, Me Me, Me e2NS02 5-F H

3-196 Me, Me Me, Me Ac 5-F H

3-197 Me, Me Me, Me AcO 5- CI H

3-198 Me, Me Me, Me OMe 5-CI H

3-199 Me, Me Me, Me Me3Si 5-F H

3-200 Me, Me Me, Me (MeO) 2PO 5-F H

3-201 Me, Me Me, Me H 5-PYR H

3-202 Me, Me Me, Me H 6-PYR H

3-203 Me, Me Me, Me H 5-THI H

3-204 Me, Me Me, Me H 6-THI H

3-205 Me, Me Me, Me H H 8-PYR

3-206 Me, Me Me, Me H H 7-PYR

3-207 Me, Me Me, Me H H 6-PYR

3-208 Me, Me Me, Me H H 5,8-PRA

3-209 Me, Me Me, Me H H 5,7-OXZO

3-210 Me, Me Me, Me H H 5,7-THA

[0075] 3-21 1 Me, Me F, F OH H H

 3-212 Me, Me F, F OH H 2-OMe

3-213 Me, Me F, F OMe H H

3-214 Me, Me F, F OEt H H

3-215 Me, Me F, F OPr H H

3-216 Me, Me F, F OAIIyl H H

3-217 Me, Me F, F OBn H H

3-218 Me, Me F, F OAc H H

3-219 Me, Me Me, Me OH 5-F H

3-220 Me, Me Me, Me OMe 5-F H

3-221 Me, Me Me, Me OEt 5-F H

3-222 Me, Me Me, Me OPr 5-F H

3-223 Me, Me Me, Me OAIIyl 5-F H

3-224 Me, Me Me, Me OBn 5-F H

3-225 Me, Me Me, Me OAc 5-F H

3-226 Me, Me F, F Me H H

3-227 Me, Me F, F H H H

3-228 Me, Me F, F H 5-F H

3-229 Me, Me F, F Me 5-F H

3-230 Me, Me F, F Et H H

[0076] Among the above exemplified compounds, suitable compounds are compound numbers 1 10, 1 35, 1 56, 1 — 77, 1 — 78, 1 — 100, 1 — 123, 1 — 129, 1 — 130, 1 — 131, 1—132, 1—133

— 135, 1—165, 1—166, 1—167, 1—170, 1—172, 1—173, 1—177 — 178, 1—185, 1—206, 1—211, 1—212, 2—89, 2—112, 3—100, 3—12 3, 3—133, 3—167, 3—170, 3— Compounds 211, 3-219 and 3-226, and more suitable compounds are compound numbers 1-77, 1 123, 1 129, 1 130, 1-13, 1-133, 1— 135, 1—165, 1—167, 1—170, 1—172, 1—173, 1—185, 1—206, 1—211, 1—212, 3—133, 3—170, 3—211, 3-219 and 3-226 compounds,

 Particularly preferred compounds are compound numbers

1— Compound No. 123: 3— (5—Black mouth 3—Methyl 3, 4 Dihydroisoquinoline 1—yl) quinoline,

 Compound 1-130: 3— (5 fluoro-3,4 dimethyl-3,4 dihydroisoquinoline 1 yl) quinoline,

 1— Compound No. 133: 3— (5 black mouth 3, 4 dimethyl 3, 4 dihydroisoquinoline 1 yl) quinoline,

 1—No. 167 compounds: 1, —quinoline— 3—yl— 3, H—spiro [cyclobutane—1, 4, —isoquinoline],

 1—No. 170 compound: 3— (5 fluoro-4,4 dimethyl-3,4 dihydroisoquinoline 1 yl) quinoline,

 Compounds 1-172: 5, Fluoro 1, Quinoline-3 yl-3, H Spiro [cyclobutane 1, 4, monoisoquinoline],

 Compounds 1-173: 5, Fluoro 1, Quinoline—3 yl— 3, H Spiro [cyclopentane 1, 4 'isoquinoline],

 1—No. 206 compound: 3— (5 fluoro-3,3,4,4-tetramethyl-3,4 dihydroisoquinoline 1-yl) 1,7 naphthyridine,

1— Compounds No. 211: 7— (5 Fluoro 3, 3, 4, 4—Tetramethyl— 3, 4 Dihydroisoquinoline 1—yl) 3, 4 Dihydro 1H pyrido [3, 2-b] [1 , 4] oxazine, compound No. 1-212: 7— (5 Fluoro-3, 3, 4, 4-tetramethyl-3, 4 dihydric oral isoquinoline 1-yl) 4-Methyl 3, 4 Dihydro- 1H pyrido [3, 2-b] [l, 4] oxazine, 3—No. 211 compound: 3— (4, 4 difluoro 2 hydroxy— 3, 3 dimethyl— 1, 2, 3, 4—tetrahydroisoquinoline 1 yl) quinoline,

 3—No. 219 compounds: 3— (5 Fluoro-2-hydroxy-3, 3, 4, 4-tetramethyl —1, 2, 3, 4-tetrahydroisoquinoline 1-yl) quinoline and

 3— Compound No. 226: 3— (4, 4 Difluoro 2, 3, 3 Trimethyl-1, 2, 3, 4—Tetrahydroisoquinoline 1 yl) quinoline

 It is.

 [0077] The compound (la) of the present invention can be produced by a known method described in Non-Patent Document 1 or the like, or by methods A to F described below.

[0078] (Method A)

R²、 R°、 R⁴、 X、 n、 Y及び mは、前記と同意義を示す (伹 し、 R¹が結合して 、る炭素原子と R³が結合して 、る炭素原子との結合は単結合であ る。）。 [0079] In the above formula, ring A, ring B,

R ² , R °, R ⁴ , X, n, Y, and m have the same meaning as described above (where R ¹ is bonded, R ³ is bonded to R ³ , and Is a single bond.)

 Method A is a method for producing the compound (la) of the present invention by reacting a nitrile compound (II) and an alcohol compound (III) according to a litter reaction.

[0080] (Process A)

 In step A, the nitrile compound (II) is reacted with the alcohol compound (III) in the presence of an acid in a solvent or in the absence of a solvent (preferably in the absence of a solvent). ).

 The alcoholic compound (III) to be used is usually 1 to 6 mol, preferably 1.1 to 3.0 mol, per 1 mol of the nitrile compound (11).

When a solvent is used in this step, the solvent used is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, and octane. Elements; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, dichloromethane, chloroform and carbon tetrachloride; or dioxane, jetyl ether, tetrahydrofuran (THF) and ethers such as dibutyl ether, preferably hydrocarbons, aromatic hydrocarbons or halogenated hydrocarbons, and more preferably benzene or dichloroethane.

 The acid used in this step is not particularly limited as long as it is used as an acid in a normal litter reaction. For example, inorganic acids such as sulfuric acid, phosphoric acid and perchloric acid; formic acid and trifluoroacetic acid Carboxylic acids such as benzene sulfonic acid, toluene sulfonic acid and trifluoromethane sulfonic acid; or Lewis acids such as tin tetrachloride and trifluoroboron, preferably inorganic acids, carboxylic acids Acids or sulfonic acids are preferable, and sulfuric acid or trifluoromethanesulfonic acid is more preferable. The amount of the acid used is usually 1 to 20 moles per mole of the nitrile compound (11), and preferably 1 to 15 monolayers.

 While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 100 ° C., preferably 0 ° C. to 80 ° C.

 While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 15 minutes to 120 hours, preferably 30 minutes to 72 hours.

 The starting material of the above-mentioned method A-Torrui compound (II) is a known compound or a known method {for example, Non-Patent Document 5: Journal, Med, Medicinal, Chemistry (j. Med. m.), 22 卷, page 816 (1979)}.

 The alcohol compound (III) used in this step is a known compound, or a known method {for example, Non-Patent Document 6: Tetrahedron, 55 卷, page 4595 (1999). Can be produced according to the method

 The compound (lb) of the present invention can be produced by Method B described below.

(Method B)

In the above formula, ring A, ring B, R \ R ³ , X, n, Y and m are as defined above (provided that, in the compound (la ′), R ¹ is bonded). The carbon atom to which R ³ is bonded is a single bond, and in the compound (lb), the carbon atom to which R ¹ is bonded to the carbon atom to which R ³ is bonded in the compound (lb). The bond is a double bond.) O

In Method B, the compound (lb) of the present invention is produced by acidifying (dehydrogenating) the compound (la ′) in which R ² and R ⁴ are hydrogen atoms in the compound (la) of the present invention. Is the method.

 [0083] (Process B)

 Step B is a step for producing the compound (lb) of the present invention by oxidizing (dehydrogenating) the compound (la ′) in a solvent in the presence of a catalyst.

 The catalyst used in this step is not particularly limited as long as it is used for a normal oxidation (dehydrogenation) reaction. For example, it can be palladium carbon, acid platinum or Raney nickel, and preferably palladium. —Carbon.

 The amount of the catalyst used is usually from 0.005 to 10 mol, and preferably from 0.05 to L0 mol, relative to 1 mol of the compound (la ′).

 The solvent used in this step does not inhibit the reaction, and is not particularly limited as long as it is a solvent. For example, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane, Halogenated hydrocarbons such as chloroform and tetrasalt carbon; or ethers such as dioxane, jetyl ether, tetrahydrofuran (THF) and dibutyl ether, preferably hydrocarbons More preferably, it is toluene or xylene.

While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally 0 ° C to 200 ° C, preferably 20 ° C to 180 ° C. While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 1 hour to 120 hours, preferably 3 hours to 72 hours.

 Compound (Ic) of the present invention can be produced by Method C and Method D described below.

 (C method)

R⁴、 X、 n、 Y及び mは、前記と同意義を示す (伹 し、 R¹が結合して 、る炭素原子と R³が結合して 、る炭素原子との結合は単結合であ る。）。 [0085] In the above formula, ring A, ring B,

R ⁴ , X, n, Y, and m are as defined above (where R ¹ is bonded, R ³ is bonded to R ³ , and the bond to the carbon atom is a single bond). is there.).

Method C is a method for producing compound (1) in which R ⁵ is a hydrogen atom in compound (Ic) of the present invention by reducing compound (la) of the present invention.

[0086] (Process C)

 Step C is a step for producing compound (Ic ′) of the present invention by subjecting compound (la) to a reduction reaction in a solvent.

The reduction reaction used in this step is not particularly limited as long as it is used to reduce imine. For example, a catalytic reduction catalyst such as palladium carbon, platinum oxide and Raney nickel and hydrogen are used. Catalytic hydrogenation reaction; reaction using a combination of metal-acid such as zinc-acetic acid and tin-hydrochloric acid as the reducing agent; such as lithium aluminum hydride, sodium borohydride and sodium cyanoborohydride as the reducing agent The reaction may be a reaction using a metal hydride, preferably a reaction using a metal hydride as a reducing agent, and more preferably a reaction using sodium borohydride as a reducing agent. The amount of the metal-acid combination or metal hydride used is compound (la) 1 monolayer, but usually 0.5 to 20 monoles, which is preferred. ί, 0.5 to 10 mono. Moreover, the hydrogen pressure used for the catalytic hydrogenation reaction is usually 1 to 10 atm, and preferably 1 to 2 atm.

 The solvent used in this step does not inhibit the reaction, and is not particularly limited as long as it is a solvent. For example, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane, Halogenated hydrocarbons such as black mouth form and tetrasalt carbon; alcohols such as methanol, ethanol and 2-propanol; acids such as acetic acid, hydrochloric acid and sulfuric acid; or dioxane, jetyl ether, Ethers such as tetrahydrofuran (THF) and dibutyl ether can be used, preferably alcohols, and more preferably ethanol.

 While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally 0 ° C to 200 ° C, preferably 20 ° C to 180 ° C.

 While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 1 hour to 120 hours, preferably 2 hours to 72 hours.

[0087] (Method D)

X、 n、 Y及び mは、前記と同意義を示し、 R°a は、 R⁵における、置換されていてもよい C〜Cアルキル基、置換されていてもよい C [0088] In the above formula, ring A, ring B,

X, n, Y and m represents the same meanings as defined above, R ° a is in R ^5, which may be substituted C~C alkyl group, an optionally substituted C

 1 6 1

~ C alkylsulfur group, optionally substituted c ~ c alkylsulfur group

6 1 6

 , Optionally substituted c ~ group, optionally substituted

 1c alkylsulfamoyl

 6

 Aralkyl group, acyl group, tree (C ~

 1c alkyl) silyl group or Gee (

 6 c ~

Shows a 1 c alkoxy 6) phosphoryl group (provided that in R ¹ is a bond, Ru bonded carbon atoms and R ^3, Ru bond with the carbon atoms is a single bond.) O

Method D consists of alkylating, sulf-Louis 匕, sulfo-Louis 匕, sulfamoylation, aralkylation, acylation, silylation or phosphorylation of the compound (Ic,) of the present invention. This is a process for producing the compound (Ic ") of the invention.

 (Process D)

 In step D, compound (1) is converted to a compound in the presence of a base in a solvent.

Z-R ⁵ a, (IV)

(In the formula, R ⁵ a ′ has the same meaning as R ⁵ a except for the formyl group, and Z represents a halogen atom, particularly a chlorine, bromine or iodine atom.)

In which R ⁵ is R ⁵ a to produce a compound (Ic ″) of the present invention by reacting with a compound (IV) having the formula (IV) or a mixed acid anhydride of formic acid and acetic acid.

 The amount of compound anhydride (IV) and the mixed acid anhydride of formic acid and acetic acid used is usually 1 to 130 monolayers for compound (Ic ') 1 monolayer, and preferably 1.1 to 1 10 monoles.

 The base used in this step is not particularly limited as long as it is used as a base (deoxidizing agent) in a normal reaction. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate And alkali metal hydrogen carbonates such as potassium hydrogen carbonate; alkali metal hydrides such as sodium hydride, lithium hydride and potassium hydride; sodium hydroxide, potassium hydroxide and barium hydroxide Alkali metal hydroxides or alkaline earth metal hydroxides; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; triethylamine, tributylamine, diisopropylethyla Min, N-methylmorpholine, pyridine, 4-((N, N-dimethylamino) pyri , N, N-dimethylaniline, N, N-jetylaniline, 1,5-diazabicyclo [4.3.0] noner-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABCO) And 1,8-diazabicyclo [5. 4. 0] — 7-undecene (DBU) and other organic bases; or organic metals such as butyl lithium and lithium diisopropylamide, preferably alkaline Metal carbonate, more preferably potassium carbonate.

 The amount of the base to be used is generally 1-30 mol, preferably 1.1-10 mol, per 1 mol of compound (IV).

The solvent used in this step does not inhibit the reaction, and is not particularly limited as long as it is a solvent. For example, hydrocarbons such as hexane, cyclohexane, benzene and toluene; Halogenated hydrocarbons such as chloromethane, dichloroethane, chloroform and tetrachloroethane; ethers such as dioxane, jetyl ether, tetrahydrofuran (THF) and ethylene glycol dimethyl ether; dimethylformamide, dimethylacetamide and Amides such as hexamethylphosphoric triamide (HMPA); ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; -tolyls such as acetonitrile and isobutyric-tolyl; or methyl acetate, Esters such as ethyl acetate and propyl acetate can be used, preferably ketones, and more preferably acetone.

 While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 150 ° C., preferably 0 ° C. to 40 ° C.

 While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 5 minutes to 120 hours, preferably 15 minutes to 48 hours.

 (E method)

X、 n、 Y及び mは、前記と同意義を示す (但し 、 R¹が結合して 、る炭素原子と R³が結合して 、る炭素原子との結合は単結合である 丄 (VI) (Id) In the above formula, ring A, ring B,

X, n, Y and m are as defined above (provided that R ¹ is bonded and R ³ is bonded to R ^{3 and the} bond to the carbon atom is a single bond)

Method E is a method for producing the compound (Id) of the present invention in which R ⁵ is a hydroxyl group by oxidizing and reducing the compound (la).

(E-1 process) In step E-1, the oxazolidine compound (V) is produced by reacting the compound (la) produced according to the above method A with an oxidizing agent in a solvent or non-solvent (preferably in a solvent). It is a process to do.

 When a solvent is used in this step, the solvent used is not particularly limited as long as it does not inhibit the reaction. For example, organic acids such as formic acid and acetic acid; hexane, cyclohexane, benzene, toluene and Hydrocarbons such as xylene; halogenated hydrocarbons such as dichloromethane, dichloromethane, chloroform and carbon tetrachloride; alcohols such as methanol, ethanol and 2-propanol; or dioxane, jetyl ether, Ethers such as tetrahydrofuran (THF) and dibutyl ether can be used, preferably alcohols or hydrocarbons, more preferably alcohols, and particularly preferably methanol.

 The oxidizing agent used in this step is not particularly limited as long as it is used in a reaction in which ordinary imine is oxidized to oxazolidine. For example, methacroperbenzoic acid, paranitroperbenzoic acid and Perbenzoic acids such as monoperoxyphthalic acid; peracids such as trifluoroperacetic acid, peracetic acid and formic acid; peroxides such as dimethyldioxolane; Hydroperoxides such as hydroxide, tamyl hydroperoxide and hydrogen peroxide, preferably perbenzoic acids, peracids or hydroperoxides under metal catalysis. More preferred are perbenzoic acids or peracids, and particularly preferred are metabenzoic perbenzoic acid or peracetic acid.

 The amount of the oxidizing agent used is usually 1 to 20 moles per mole of the compound (la), and preferably 1 to 15 monolayers.

 The reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, but is usually 0 ° C to 200 ° C, preferably 10 ° C to 100 ° C.

 While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 15 minutes to 120 hours, preferably 30 minutes to 72 hours.

 (E-2 process)

Process E-2 is a process for producing N-xoxide compound (VI) by treating oxazolidine compound (V) with an acid in a solvent or non-solvent (preferably in a solvent). . When a solvent is used in this step, the solvent used is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane , Halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride; or ethers such as dioxane, jetyl ether, tetrahydrofuran (THF) and dibutyl ether, preferably halogen. Hydrocarbons, and more preferably black mouth form.

 The acid used in this step is not particularly limited. For example, inorganic acids such as sulfuric acid, formic acid, phosphoric acid and perchloric acid; sulfonic acids such as benzenesulfonic acid, toluenesulfonic acid and trifluoromethansulfonic acid; or Lewis acids such as tin tetrachloride and trifluoroboron can be used, preferably inorganic acids or sulfonic acids, and more preferably sulfuric acid or methanol sulfonic acid.

 The amount of the acid used is usually 1 to 20 mol, preferably 1.1 to 15 mol, per 1 mol of the oxazolidin compound (V).

 While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 100 ° C., preferably 0 ° C. to 80 ° C.

 While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 15 minutes to 120 hours, preferably 30 minutes to 72 hours.

 (E—3 steps)

 Step E-3 is a step for producing the compound (Id) of the present invention by subjecting the N-oxide compound (VI) to a reduction reaction in a solvent, except for the following conditions. It is performed in the same way as the process.

 The reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, but is usually 0 ° C to 200 ° C, preferably 10 ° C to 100 ° C.

 While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 10 minutes to 72 hours, preferably 15 minutes to 24 hours.

(F method)

In the above formula, ring A, ring B, RRRR ⁴ , X, n, Y and m are as defined above, R ⁵ b is an optionally substituted C to C alkoxy group in R ⁵ , C optionally substituted

 1 6

 ~ C alkyloxy group, optionally substituted c ~ c alkyloxy group, substituted

2 6 2 6

In this case, it represents an aralkyloxy group or an acyloxy group (provided that R ¹ is bonded and TV, a carbon atom and R ³ are bonded, and the bond between the carbon atom is a single bond).

Method F is a method for producing a compound (Ie) of the present invention in which R ⁵ is R ⁵ b by alkylating, alkenylating, alkynylating, aralkylating or acylating the compound (Id) of the present invention. It is.

 (F process)

 Step F comprises compound (Id) in the presence of a base in a solvent with the formula

 Z-R, (VII)

(Wherein R ⁵ b ′ is a group excluding the formyl group, and a group excluding the oxygen atom (ie, excluding the formyloxy group, R ⁵ b is —O—R ⁵ b)). Z represents a halogen atom (in particular, a chlorine, bromine or iodine atom).

Is a step of producing a compound (Ie) of the present invention by reacting with a halogenated compound (VII) or a mixed acid anhydride of formic acid and acetic acid, except for the following conditions, The same is done.

 The base used in this step is preferably an alkali metal carbonate or alkali metal hydride, more preferably an alkali metal hydride, and most preferably sodium hydride.

 The solvent used in this step is preferably an amide or a ketone, more preferably an amide, and most preferably dimethylformamide.

While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 150 ° C., preferably 0 ° C. to 40 ° C. While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

[0090] After completion of each of the above reactions, the target compound of each reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insoluble matter is present, it is appropriately removed by filtration, and then an organic solvent immiscible with water, such as ethyl acetate, is added, washed with water, and then containing the target compound. The organic layer is separated and dried over anhydrous magnesium sulfate, and then the solvent is distilled off to obtain the target compound for each reaction.

[0091] If necessary, the obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation or chromatography.

 [0092] The step of producing the salt of the compound (I) of the present invention comprises the compound (la), (lb),

 Extract concentrate of reaction mixture containing (Ic '), (Ic "), (Id) and (Ie), or compounds (la), (lb), (Ic'), (Ic") (Id) and This is carried out by adding an acid to a solution obtained by dissolving (Ie) in a suitable solvent.

 [0093] The acid used in the reaction is a hydrohalic acid (eg hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid), inorganic such as nitric acid, perchloric acid, sulfuric acid and phosphoric acid. Acids; alkyl sulfonic acids (eg methane sulfonic acid, trifluoromethane sulfonic acid and ethane sulfonic acid), aryl sulfonic acids (eg benzene sulfonic acid and ρ-toluene sulfonic acid) and carboxylic acids (eg succinic acid and sulfur Acid) and organic acid amide compounds such as saccharin, preferably nitric acid, sulfuric acid or methanesulfonic acid.

 The amount of the acid used is usually 1 equivalent to 10 equivalents, and preferably 1 equivalent to 5 equivalents.

 [0094] The solvent used in the reaction is not particularly limited as long as the reaction is not inhibited. For example, ethers such as ether, diisopropyl ether, tetrahydrofuran (THF) and dioxane; or methanol and ethanol And preferably are ether or methanol.

 [0095] The reaction temperature is usually -20 ° C to 50 ° C, preferably -10 ° C to 30 ° C.

The reaction time varies depending on the type of solvent used and the temperature. ~ 1 hour.

 [0096] The resulting salt is isolated by conventional methods. That is, it is isolated by filtration when it is precipitated as crystals, and is isolated as an aqueous solution by separating an organic solvent and water when it is water-soluble.

 [0097] The compound (I) of the present invention is useful as an active ingredient of an agrochemical composition (particularly a pest control agent). For example, as an agricultural and horticultural fungicide, it exhibits an excellent control effect against diseases caused by various plant pathogens. In particular, rice blast, head blight, azuki bean, tomato, cucumber and kidney beans gray mold, mycorrhizal disease, onion white leaf blight, wheat snow rot, powdery mildew, apple moniliosis, spots Excellent control effect against various diseases such as deciduous leaf disease, tea anthracnose, pear red star disease, black spot disease, grape black depression and citrus black spot disease. Since the compound of the present invention has an excellent therapeutic effect, disease control by treatment after infection is possible.

 [0098] When using the compound of the present invention, in the same manner as in the case of conventional agricultural chemical preparations, various forms such as emulsions, powders, wettable powders, liquids, granules and suspensions are prepared together with adjuvants. Can be formulated. In actual use of these preparations, they can be used as they are or after diluting to a predetermined concentration with a diluent such as water.

 [0099] The auxiliary agent used can be a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickening agent, a stabilizer, and the like, and can be appropriately added as necessary. .

[0100] The carrier used is divided into a solid carrier and a liquid carrier, and the solid carrier is starch, sugar, cellulose powder, cyclodextrin, activated carbon, soy flour, wheat flour, chaff flour, wood flour, fish flour and milk powder. Animal or vegetable powders such as; or minerals such as talc, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white force, bonbon, clay, alumina, silica and sulfur powder Liquid carrier can be powder; water; animal and vegetable oils such as soybean oil, nut oil and corn oil; alcohols such as ethyl alcohol and ethylene glycol; ketones such as acetone and methyl ethyl ketone Ethers such as dioxane and tetrahydrofuran; kerosene, kerosene, liquid paraffin, xylene, toluene Aliphatic Z aromatic hydrocarbons such as methylbenzene, tetramethylbenzene, cyclohexane and solvent naphtha; Halogenated hydrocarbons such as black mouth form and black mouth benzene; Acid amides such as dimethyl formamide Class: Ethiacetate Esters such as glycerol esters of fatty acids and fatty acids; -tolyls such as acetonitrile; sulfur-containing compounds such as dimethyl sulfoxide; or pyrrolidones such as N-methylpyrrolidone.

 [0101] The compounding mass ratio of the compound of the present invention to the adjuvant is usually 0.05: 99.95 to 90:10, and preferably 0.2: 99.8 to 80:20.

 [0102] The concentration or amount used of the compound of the present invention varies depending on the target crop, method of use, formulation, application rate, etc., but in the case of foliage treatment, it is usually 0.1 to 10,000 ppm per active ingredient. In the case of soil treatment, it is usually 10-: LOOOOOgZha, preferably 100-10000 gZha.

 [0103] The compound of the present invention may contain other pesticides such as insecticides, acaricides, attractants, nematicides, fungicides, antiviral agents, herbicides, and Z or plant growth as necessary. It can be mixed or used in combination with agents, and those used or combined are preferably insecticides, acaricides, nematicides or fungicides.

 [0104] The insecticides used are, for example, O, O Jetyl—O— (5 phenol—3-isoxazolyl) phosphorothioate (generic name: isoxathione), O, O dimethyl—O— (3— Methyl-4-tropho) thiophosphate (generic name: phetrothion), O, O Jethyl O- (2 isopropyl-4-methylpyrimidine-6 yl) thiophosphate (generic name: diazinon), O , S Organophosphate compounds such as dimethyl N-acetyl phosphoramidothioate (generic name: acephate) and O, O dimethyl S—1,2-diethoxycarbo-ruethyl dithiophosphate (generic name: malathion);

 [0105] 2-tert-Butylimino-1-3-Isopropyl-5-Fu-Lu 3, 4, 5, 6-Tetrahydro

 -2H- 1, 3, 5 Thiadiazine-4-one (generic name: buprofen), 1 naphthinole N-methyl carbamate (generic name: carnolyl), 2-isopropoxyphenyl N-methyl carbamate (generic name: proboxil) , S-methyl N- (methylcarbamoyloxy) thioacetimidate (generic name: mesomil) and N, N dimethyl-2-methylcarbamoyloximino 2- (methylthio) acetoamide (generic name: oxamyl) Silicate compounds;

[0106] (RS)-a—Shiano 1 3 phenoxybenzyl = (RS) —2— (4—black mouthpiece)- 3-methylbutyrate (generic name: fenvalerate), 3-phenoxybenzyl = (IRS, 3 RS) — (IRS, 3SR) — 3— (2,2 dichlorobut) -1,2,2 dimethylcyclopropane carboxy Pyrethroid compounds such as rate (generic name: permethrin) and 2- (4 ethoxyphenol) 2 methyl propyl 3-phenoxybenzyl ether (generic name: etofenprox);

 [0107] 1- [3,5 Dichloro 4-4- (3 Black mouth 5 Trifluoromethyl 1-2 Pyridyloxy) phenol] —3— (2, 6 Difluro-benzoyl) urea (generic name: Chlorfur) Benzoylurea compounds such as 1) (3,5 dichloro-2,4 difluorophenol) 3— (2,6 diflurobenzoyl) urea (generic name: teflubenslon);

[0108] 1— (6 Chlomouth 1-Pyridylmethyl) N-tro-Imidazolidine 1 2-Ilideneamine (generic name: Imidacloprid) and [C (E)] — N— [ E) methyl] neonicotinoid compounds such as N, monomethyl mononitroguanidine (generic name: clothiazine); or

 [0109] 5-Amino 1- [2, 6-Dichloro 1- (Trifluoromethyl) phenol] — 4— [(Trifluoromethyl) sulfier] 1— 1H Pyrazole-3 Carbo-tolyl (generic name: Fipro) -L).

 [0110] The fungicides used are, for example, Manganese ethylene bis (dithiocarbamate) (generic name: mannebu), zinc and manganese ethylenebis (dithiocarbamate) (generic name: manzeb) and 3, 3 ethylene. Dithiocarnomate compounds such as bis (tetrahydro-4,6 dimethyl-2H-1,3,5-thiadiazine 2-thione (generic name: mirneb) (trichloromethylthio) cyclohexene 4-ene 1,2 dicarboximide (general N-halogenoalkyl, such as N- (l, 1, 2, 2-tetrachloroethylthio) cyclohexyl-4-ene-1,2-dicarboximide (generic name: captaphor) Thioimide compounds;

 Halogenoaromatic compounds, such as 4, 5, 6, 7-tetrachlorophthalic phthalide (generic name: fusalide) and tetrachlorophthalic isophthalic-tolyl (generic name: chlorothalic);

Methyl 1 (butylcarbamoyl) 2-benzimidazole carbamate (generic name: Benzimidazole compounds such as Benomyl);

 (E) — 4 black mouth a, a, α trifluoro N— (1—imidazole 1—yl— 2 propoxyshtildene) o toluidine (generic name: triflumizole), 2— (4 black mouth ferrule) ) — 2— (1H— 1, 2, 4 Triazole— 1-ylmethyl) hexane-tolyl (generic name: microbutayl), N-propyl mono N— {2— (2, 4, 6 trichlorophenoxy) C) Ethyl} Imidazole-1 Carboxamide (generic name: Prochloraz) and 2- (4 Fluoro-Fol) — 1— (1H— 1, 2, 4 Triazol 1-yl) —3 Trimethylsilyl mouth bread 2-ol ( Azole compounds such as (generic name: cimeconazole);

 3 Kuroguchiichi N— (3 Kuroguchiichi 2, 6 Dinitro 1 4-a,, α Trifnoreo Minotrinore) — 5 Pyridine amine compounds such as trifluoromethyl-2-pyridinamine (generic name: fluazinam);

 1- (2 cyano-2-methoxyiminoacetyl) 3 cyanoacetamide compounds such as 3 ethyl urea (generic name: simoxa-l);

 Methyl Ν— (2-methoxyacetyl) Ν— (2, 6 xylyl) DL ara-nate (generic name: metalaxyl) and 2-methoxy Ν— (2 oxo 1, 3 oxazolidin-3-yl) aceto 2 ' , 6 'xylidide (generic name: oxadixyl) methyl Ν -phenylacetinol Ν— (2, 6 xylinole) DL amide compounds (generic name: benalaxyl);

 Ν— (3,5 dichlorophenol) -1,2,2 dimethylcyclopropane-1,2,2 dicarboximide (generic name: Procymidone), 3-— (3,5 dichlorophenol) One イ ソ —Isopropinole 2,4 diio Xicoimidazolidine—dicanolevoxyimides such as 1-carboxamide (generic name: yprodione) and 3— (3,5 dichlorophenol) -5-methyl-5 bulyl-1,4-oxazolidinone (generic name: vinclozolin) System compound;

 Copper-based compounds such as cupric hydroxide (generic name: cupric hydroxide) and kappa 8-quinolinolate (generic name: quinoline copper);

 Isoxazole compounds such as 3-hydroxy 5-methylisoxazole (generic name: hymexazole);

Aluminum tris (ethyl phosphonate) (generic name: fosetyl aluminum), Ο— 2, 6 -Dichloro-p-tolyl = o, o dimethyl phosphorothioate (generic name: Torque Mouth Phosmethyl), S benzyl O, O diisopropyl phosphorothioate and O ethyl S, S diphenol-nore phosphorodithioate, aluminum Organophosphorus compounds such as tilhydrogen phosphonate;

 Benth anilide compounds such as a, a, α-trifluoro-3, monoisopropoxy o toluanilide (generic name: flutol) and 3'-isopropoxy-o tolurilide (generic name: meprol);

 (E, Z) 4— {3— (4-Chlorophenol) — 3— (3, 4-Dimethoxyphenol) Ataliloyl} Morpholine (generic name: dimethomorph) and (shi) —cis— 4— {3— Morpholine compounds such as (4-t-butylphenol) -2-methylpropyl} -2,6-dimethylmorpholine (generic name: fenpropimol);

 1, 1-iminotazine-based compounds such as iminodi (otatamethylene) digadi-umtriacetate (generic name: iminotadine);

 1, 2, 5, 6-Tetrahydro 4H Pillow Mouth [3, 2, 1—ij] Quinolin 4-one (generic name: Pyroxylone), 4, 5, 6, 7-Tetrachromic Fusaride (generic name: Fusaride) ) And 2, 2 Dicloguchiichi N— [1— (4 Black mouth) ethyl] 1 Ethyl 3 Methylcyclopropane carboxamide (generic name: Carprobamide); Melanin biosynthesis inhibitors;

 Resistance inducers such as 1, 2, 5, 6-tetrahydro-l-alkyloxy 1, 2 benzisothiazole 1, 1-dioxide (generic name: probenazole);

 Copper agent;

 Sulfur agent;

 Or it may be a tin agent.

 [0111] Hereinafter, the compounds of the present invention will be specifically described with reference to Examples, Formulation Examples and Test Examples. The present invention is not limited to these.

 Example

[0112] Example 1

'ε— Λ / 一 g)— ε 2 Black mouth 3— (5-Fluoro-3, 3, 4, 4— Tetramethyl 1, 3, 4 Dihydroisoquinoline — 1—yl) quinoline (Compound No. 1—198) (Process A) )

'ε— Λ / 1 g) — ε

 (¾χο) (粱 οτ ε each ε ε category [πο]

° εΐ 'eSS' £ LZ ₊ Vi) fLZ: (z / m) ^ mu

° (ZH0 = f 'P' Ηΐ) ΐε

f 'P' HI) ZO'S '(89

H N-H_T 'Ηΐ) 6S'Z— SS'Z

H NH _T

 . One. OSI-9 ΐΐ: Whip

目 (I/I ° -Μ

Eye (I / I

'ε— ci / 一 g)— ε ^ Translate 8ΐ ^ W ^ ( ^m 0 · 9) 峯 ^ —Ma ^% 01 -2M ^m · Χ) Λ ^ Ο) Λ (^

'ε—ci / 1 g) —ε

 (¾X9) (ox-s- ^ M ^ »be ίί, ^ ρ 1 ίί, ^^ ΰ / s) — ε

zm [επο] ° 9ετ '88 ΐ ¹ 7ΛΖ '9ΐε' τεε '( ₊ ) 99ε' ++ ^) 89ε :( ^ζ / ω) ^ mu

' Ήΐ ° (s' Ηΐ) Z'S

'Ήΐ

H N-H_T ) WL '(zHS'8 = f''Ηΐ)WL' (ω 'ΗΖ) 9VL-ZVL' (ω 'Ηΐ) 0Γ9- 89 · 9' ( ^s Ήε) 09 · ΐ '(s Ήε) 03 "ΐ '(s Ήε)

H NH _T

. (% 6 ¾1) ₀ ^^ eyes, ^

·χ べ

· Χ

^Si "0Q ε) —- ^ -z- K ^ ^^^-ε 'z- (^ —- ^ ^ -z) —ε, ¾

t9

8L l £ / 900ZdT / 13d ° εΐ 'ΟΖΖ' SfZ Ί Ζ 'LZ ₊ Vi) 9LZ: (z / ui) mu

 ° (ZHO = 1 "'Ρ' Ηΐ)

'P 'Ηΐ) Z8"Z '(ΖΗ9·8= f

3Γ6 '(ZHO

'P' Ηΐ) Z8 "Z '(ΖΗ9 · 8 = f

H N-H_T

H NH _T

(χε

 -ΐEach 粱 呦 ^^ Be ίί, ^ ρ (/ y- i- ^ ^ y si ^-'ε— ci / — 9) — ε

S-zone No. [9] 0] ° εΟΖΖ 'ΟΖΖ' LfZ Ί L 'LZ ₊ Vi) 9LZ: (z / m) mu

° (ZH0 = 1 "'P' Ηΐ) 9Γ6 '( ^z H0" 2 = f' P 'Ηΐ) 8S "8' (zW8 = f 'P' Ηΐ) ΖΓ8 mVS = i 'P

 'Ηΐ) Z8 "Z' (ΖΗ · 8 = ί" '' Ηΐ) SL'L ^ HVS = i '' Ηΐ) 6S "Z '(ω Ήε) LZ'LSO'L ^ HVL

= f 'ΗΖ) S6 "S VL = [' ΗΖ) 68: ^ dd g (OQO 'ZH ^ H ^ H NH _T

(# 01

 -ΐEach 粱 呦 ^^ Be ίί, ^ ρ (/ y- i- ^ ^ y si ^-'ε— ci / — s) — ε

 w, [eno]

. > n 呦 ^^) ½ί ^ ¾ϊ 第 〜 ϋ¾ϊ 第 《定 «m 翁 ^; ε〜τί ^ ¾ϊ 第

° OSI 'ΟΖΖ' SfZ ₊ Vi) SLZ: (ζ / ω) ^ mu

° (ΖΗ9 · ΐ = ί "'Ρ' Ηΐ) 68 · 8 '(ΖΗΖ · Ζ = ί"' Ρ 'Ηΐ) ZVS' ( ^ζ

'Ρ 'Ηΐ Η9 · ΐ = ί "'Ρ' Ηΐ) WL '(ΖΗΖ · Ζ = ί"' Ρ 'Ηΐ) IV I' (ΖΗΖ · Ζ = ί "'Ρ' Ηΐ) ZL

'Ρ' Ηΐ

) WL '(ω' ΗΖ) 00 ·-06 · 9 '( ^Ζ Η2 ・ 8 = Γ' Ρ 'Ηΐ) 69 · 9' ( ^s 'Ηΐ) IS'S' (ω 'Ηΐ) Z-LZ'Z'

H N-H_T (ω 'ΗΪ) 8ΐ · ε— ει · ε' (ω Ήζ) οο · ε— 6 ：

H NH _T

.

Ε, ¾tiii¾ ( ^Sui os) ma fH 峯 峯 氺, tsu ^ (T ^ O, s) / —, ¾ (

S9

8L l £ / 900ZdT / 13d (粱

° m 'szi Ί Ζ Ίβζ ₊ η) Ζ6Ζ z + ₊ n) f6Z-(^ / ^ ^^^

° (ΖΗΟ = 1 ”'Ρ' Ηΐ) 3Γ6 '(ΖΗΟ = 1”' Ρ Ή ΐ) ZS "8

= 1 "'' Ηΐ) 6S" Z '(s Ήΐ) 2ε *

H N-H_T

H NH _T

(粱

 9ε-"[Each 粱 呦 ^^ All ίί, ^ ρ (/ y- 1-^ ^ y si ^ ― 'ε— ^ — 9) — ε

 8th [6Π0]

° fll 'SZI' ΖΟΖ 'SZZ Ί Ί Ζ6Ζ' ( ₊ Vi) Z6Z Z + ₊ n) f6Z-(^ / ^ ^^^ ° (ZH0 = f 'P' Ηΐ) εΐ · 6 '(ZHO = f' P 'Ηΐ) 9S "8 8 = 1"' P 'Ηΐ) 9Γ8'(zHS'8 = f 'P

'Ηΐ) 98

= f 'ΗΖ) 96 · ε VL = [ΉΖ) L6'Z: ^ dd g (3Q0' ZH ^ H ^ H NH _T

(粱

- ε9S-"[Each one

-ε

 m [8πο]

° SZl 'ΟΖΖ' LfZ Ί Ζ 'LZ ₊ Vi) 9LZ: (ζ / ω) mu

 ° (ZH0 = f 'P' Ηΐ) 8Γ6 '(ZHO = f' P 'Ηΐ) 6S "8 8 = 1"' P 'Ηΐ) 8Γ8' (zHS'8 = f 'P

'HI) S8 "Z' (zH2" 8 = f '' Ηΐ) 6Z "Z '(zH2" 8 = f' 'Ηΐ) Ϊ9 "Ζ' (ω Ήε) 2S" Z-66 "9 ^ HVL

mm no]

99

'ε— ^ EH — 9)— ε 8L l £ / 900ZdT / 13d (粱 z — "[Each 粱 呦

'ε— ^ EH — 9) — ε

° en 'szi' zfz Ί Ζ '\ LZ ₊ n) ZLZ-(^ / ^ ^^^

' 'Ηΐ) SL'L ' 'Ηΐ) 0 9"Z '(ΖΗε·8=ί" 'P 'Ηΐ) 9Z'L

' 'ΗΖ) Z6 •S

H N-H_T ° (ZHO = f 'P' Ηΐ) 9Γ6 '(ZHO = f' P 'Ηΐ) WS' ( ^Z H

'' Ηΐ) SL'L '' Ηΐ) 0 9 "Z '(ΖΗε · 8 = ί"' P 'Ηΐ) 9Z'L

'' ΗΖ) Z6 • S

H NH _T

— ε °szi 'βη 'βζζ Ί Ζ 'ess

(粱 τ — "[Each 粱 呦

— Ε ° szi 'βη' βζζ Ί Ζ 'ess

° (ZHS = 1 "'Ρ' Ηΐ) fV6 = 1"'Ρ' Ηΐ) 9S "8 '( ^z H0" 8 = f' P 'Ηΐ) ΖΓ8' (VL = {'P' Ηΐ) 98 · ' (ΖΗ0 · 8 'Ζ'Ζ' 0 · ΐ = ί '' PPP 'Ηΐ) IV I' (ΖΗΖ · Ζ = ί "'Ρ' Ηΐ) Ζ9" Ζ '(ΖΗ 0 · 8' ΓΖ '0 · ΐ = ί "'ΡΡΡ' Ηΐ) 63" Ζ '(ΖΗΖ · Ζ = ί "' Ρ 'Ηΐ) fZ'L

H N-H_T

H NH _T

(粱

'ε-¾ΰ :-9)— ε 8ε-ΐEach 粱 呦

'ε-¾ΰ: -9) — ε

° fll 'SZI' ΖΟΖ '6ΖΖ Ί Ζ Ζ6Ζ' ( ₊ Vi) Z6Z Z + ₊ n) f6Z ■ (' ^Z / ^) ^^^

0 ( ^s 'Ηΐ) ΖΓ6' ( ^s 'Ηΐ) 0 8' ( ^Ζ Η2 ・ 8 = Γ 'P' Ηΐ) 6Γ8 '(zHS'8 = f' P 'Ηΐ) 06 "Z'(zHS'8 = f '' Ηΐ) 08

= f ';' ΗΖ) S6 "S VL = ['; ΉΖ) fS'Z: radd g (OQO' zH 00S) 4 ^^^ H NH _T

L9

8L l £ / 900ZdT / 13d gi m [92ΐο]

° en 'szi' οζζ 'zfz' ess '\ LZ' ( ₊ η) ζ∑ζ-(^ / ^ ^^^

 ° (ZHO = 1 "'P

'P 'HI) SZ"'Ηΐ) 80 ・ 6' (ZHO

'P' HI) SZ "

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'Ρ 'Ηΐ) ΖΖ' L 'Ρ 'Ηΐ) ss'9 '(^S 'ΗΪ)

'6·9ΐ=ί" 'ΡΡ 'ΗΪ) SOT '(^ΖΗΓΠ '6·9Ϊ= f 'PP 'Ηΐ) Ζ9'Ζ

H N-H_T 'Ηΐ) S8 "8' (ω 'ΗΖ) ΐ · 8— 80 · 8

'V-iq' Ηΐ) ΐΖ · Ζ '(ΖΗ

'Ρ' Ηΐ) ΖΖ 'L' Ρ 'Ηΐ) ss'9' ( ^S 'ΗΪ)

'6 · 9ΐ = ί "' ΡΡ 'ΗΪ) SOT' ( ^Ζ ΗΓΠ '6 · 9Ϊ = f' PP 'Ηΐ) Ζ9'Ζ

H NH _T

S Recommended No. [93 TO]

° en 'οετ' 9 'ζοζ' οζζ '6 ζ' (+ w) zs :( ^ζ / ω) m

ω 'ΗΖ) VL-1 'Ρ' Ηΐ) 0Γ8 '

ω 'ΗΖ) VL-1

VL '(ω' Ηΐ) 66 · 9— 96 · 9 '(ΖΗΖ · Ζ = 1 "' Ρ 'Ηΐ) S9"9' ( ^s 'Ηΐ) ΖΖ ^' (ω 'Ηΐ) 8Ζ-Ζτ' (ω

H N-H_T 'ΗΖ) S8 — 08

H NH _T

°. _O 90 G 0

'Ρ 'Ηΐ) 60·8 '(ω Ήε) 69"Z-S9"Z m (seioj ° en 'οετ' 9 'ζοζ' οζζ '6 ζ' (+ w) zs :( ^ζ / ω) m

'Ρ' Ηΐ) 60 · 8 '(ω Ήε) 69 "Z-S9" Z

'' Ηΐ) 0S "Z '(ω' ΗΖ) 9Z'L-IZ'L '(ΖΗΖ · Ζ = ί"' Ρ 'Ηΐ) fVL' (ΖΗΖ · Ζ = ί "'Ρ' Ηΐ) S6" 9 '( ^s ' Ηΐ) SV '(ω' Ηΐ) 60Τ-90Τ '(ZHS'9I' 8 "S = f 'PP' Ηΐ) Ζ6'Ζ 'W91' ¥ 01 =

8.M7lC / 900Zdf / X3d (ω Ή ^) S2 "2-S8" T '(ω' Hf) S8 "T-8FT: ^ dd g (3Q0 'ZH ^ H ^ H NH _T

6th Zone [0910] ° 60ΐ 'SSI' 6W '8Ζΐ' 292 '16 Ζ '( ₊ η) 90Ζ-(^ / ^ ^^^

'Ρ 'Ηΐ) 0Γ8 '(s q Ήΐ) Ϊ6"Ζ 'Ρ 'Ηΐ) 9ΓΖ '(ΖΗΖ·Ζ=ί" '； Ή ΐ) 0Ζ"Ζ '(ΖΗ ·Ζ=ί" '； 'Ηΐ) SS"Z '(ω Ή2) S0"Z-S8"9 '(ΖΗ ·Ζ=ί" 'Ρ 'Ηΐ) SS"9 '(^s 'Η2) Ζ8 •Ζ '(s Ήε) 2S"T

H N-H_T Ζ8 ・ 8

'Ρ' Ηΐ) 0Γ8 '(sq Ήΐ) Ϊ6 "Ζ' Ρ 'Ηΐ) 9ΓΖ' (ΖΗΖ · Ζ = ί"'； ΐ ΐ) 0Ζ "Ζ' (ΖΗ · Ζ = ί"'；' Ηΐ) SS "Z '(ω Ή2) S0" Z-S8 "9' (ΖΗ · Ζ = ί"'Ρ' Ηΐ) SS "9 '( ^s ' Η2) Ζ8 • Ζ' (s Ήε) 2S" T

H NH _T

 oi I-ε

8th Area [63 TO]

° τοΐ 'en' οετ '' ZL \ 'ιζζ' ζ '\ LZ' (+ ^) οοε :( ^ζ / ω) ^ mu

'Ρ 'Ηΐ) 60·8 '(s q Ήΐ) 68"Ζ '(ΖΗΖ·8=ί" 'Ρ Ή ° (ΖΗ8 · ΐ = ί "'Ρ' Ηΐ) Z8" 8

'Ρ' Ηΐ) 60 · 8 '(sq Ήΐ) 68 "Ζ' (ΖΗΖ · 8 = ί"'Ρ Ή

) 0Z'£ ' (ω 'ΗΖ) S 'Z-L£'Z '(ω 'Η^) OS'S- 00 ： ^dd g ( 3Q0 'ZH ^H ^ H N-H_T '(ZHS'Z

) 0Z '£' (ω 'ΗΖ) S' ZL £ 'Z' (ω 'Η ^) OS'S- 00: ^ dd g (3Q0' ZH ^ H ^ H NH _T

[ベ fi ^

[Be fi ^

 ^ 'ΐ 一 べ ^: ー Η'ε ¾' ε 'ー / ε—Be ίί, ^ —' τ

L w, [83ΐο] οΐ0ΐ 'SIT' SZl 'f9l' 8Ζΐ '6ΐ' 6ΖΖ 'f9Z' 6LZ 'ZOS: ( ^ζ / ω) mu

'Ρ 'Ηΐ) 0Γ8 '(s q Ήΐ) 0·8 'Ρ 'Ηΐ) 6ΓΖ '(ΖΗΖ·Ζ=ί" ΐ) 68

'Ρ' Ηΐ) 0Γ8 '(sq Ήΐ) 0 · 8' Ρ 'Ηΐ) 6ΓΖ' (ΖΗΖ · Ζ = ί "

'Ηΐ)

'Ηΐ) '(ΖΗΐ·9=ί" 'Ηΐ) '(ΖΗ6·9

'Ηΐ)' (ΖΗΐ · 9 = ί "'Ηΐ)' (ΖΗ6 · 9

6L

8.M7lC / 900Zdf / X3d , 2.85 (2H, q, J = 12.4Hz), 5.28 (IH, s), 6.52 (IH, d, J = 7.7Hz), 6.85—7.04 (2H, m), 7. 53 (IH, t, J = 7.5Hz), 7.70 (IH, t, J = 7.8Hz), 7.77 (IH, d, J = 8.2Hz), 7.91 (IH, br.s), 8.10 (IH, d, J = 8.5Hz), 8.87 (IH, d, J = 2.1Hz).

Mass spectrum (m / z): 332 (M +), 303, 289, 262, 248, 204, 157, 130, 101.

Example 50

 3— (5-Fluoro-1, 3, 3, 4, 4-Tetramethyl 1, 3, 4 Dihydroisoquinoline 1—yl) 1, 7 Naphthyridine (Compound No. 1 206)

Melting point: 134-136 ° C.

^J H-NMR spectrum (500MHz, CDCl) δ ppm: 1.33 (6H, s), 1.46 (6H, s), 6.92 (IH, d

 Three

d, J = 2.1, 6.9Hz), 7.18-7.22 (2H, m), 7.70 (IH, d, J = 5.5Hz), 8.30 (IH, d, J = 2.1Hz), 8.68 (IH, d, J = 5.5Hz), 9.15 (IH, d, J = 2.1Hz), 9.58 (IH, s).

Mass spectrum (m / z): 333 (M +), 318, 302, 290, 276, 261.

Example 51

 7— (5 Fluoro 3, 3, 4, 4—Tetramethyl 1, 3, 4 Dihydroisoquinoline 1—yl) 3, 4 Dihydro 1H pyrido [3, 2-b] [l, 4] oxazine ( Compound No. 1—21 No. 1)

Physical property: Oily substance.

^J H-NMR spectrum (500MHz, CDCl) δ ppm: 1.23 (6H, br s), 1.40 (6H, s), 3.58—3.6

 Three

 1 (2H, m), 4.23 (2H, t, J = 4.3Hz), 5.04 (IH, s), 7.08-7.12 (2H, m), 7.15-7.19 (IH, m), 7.19 (IH, d, J = 1.8Hz), 7.81 (IH, d, J = 1.8Hz).

Mass spectrum (m / z): 339 (M +), 338, 324, 296.

Example 52

 7— (5 Fluoro 3, 3, 4, 4—Tetramethyl 1, 3, 4 Dihydroisoquinoline 1—yl) 4-Methyl 3, 4, Dihydro 1H pyrido [3, 2-b] [l, 4] oxazine (Compound number 1 212)

Physical property: Oily substance.

^J H-NMR spectrum (500MHz, CDCl) δ ppm: 1.22 (6H, br s), 1.39 (6H, s), 3.16 (3H,

 Three

s), 3.48 (2H, t, J = 4.3Hz), 4.25 (2H, t, J = 4.3Hz), 7.07-7.17 (4H, m), 7.87 (IH, d, J = 1.8Hz).

Mass spectrum (m / z): 353 (M +), 352, 338, 310, 297, 148.

Example 53

 1— (6, 7 Dihydro-5H cyclopenta [b] pyridine-1-yl) 5 Fluoro 3, 3, 3, 4, 4-tetramethyl 1, 3, 4 Dihydroisoquinoline (Compound No. 1-213) Physical properties: gum.

^J H-NMR spectrum (500MHz, CDC1) δ ppm: 1.26 (6H, s), 1.42 (6H, s), 2.14-2.20 (

 Three

 2H, m), 2.98 (2H, t, J = 7.6Hz), 3.05 (2H, t, J = 7.6Hz), 6.96 (1H, d, J = 7.6Hz), 7.10-7

.20 (2H, m), 7.67 (1H, s), 8.40 (1H, s).

Mass spectrum (m / z): 322 (M ⁺ ), 321, 307, 279, 265, 250.

Example 54

 3— (5-Fluoro-1, 3, 3, 4, 4— Tetramethyl 1, 3, 4 Dihydroisoquinoline 1—Inole) 5, 6, 7, 8— Tetrahydroquinoline (Compound No. 1 214)

Physical properties: gum.

^J H-NMR spectrum (500MHz, CDC1) δ ppm: 1.26 (6H, s), 1.41 (6H, s), 1.81-1.85 (

 Three

 2H, m), 1.90-1.95 (2H, m), 2.82 (2H, t, J = 6.2Hz), 2.96 (2H, t, J = 6.2Hz), 6.97 (1H, d, J = 7.6Hz), 7.10-7.19 (2H, m), 7.53 (1H, s), 8.40 (1H, s).

Mass spectrum (m / z): 336 (M +), 335, 321, 279, 264.

Example 55

 3- (4,4 Difluoro-1,2 Hydroxy-1,3,3 Dimethyl-1,2,3,4-Tetrahydrin Oral isoquinoline 1-yl) quinoline (Compound No. 3—No. 211)

 (1) 4, 4 Difluoro 1, 3, 3 Dimethyl 8b Quinoline 1 3-yl 1, 4, 8b Dihydro — 3H Oxazileno [3, 2-a] isoquinoline (Step E-1)

、§ω·_3εε)マ 峯 峯氺 ' ε -

3- (4, 4 Difunoleol 3, 3 Dimethinoleol 3, 4 Dihydroisoquinoline 1-yl) quinoline (12.0 g, 36.0 mmol) in methanol (250 mL) was added to m-cloperbenzoic acid (9 0 g) was added, and the mixture was stirred at room temperature for 5 hours, and then an aqueous sodium sulfite solution and an aqueous sodium hydrogen carbonate solution were added. After stirring for 30 minutes, extraction with ethyl acetate is performed, the extract is concentrated under reduced pressure, and the resulting residue is subjected to silica gel column chromatography (elution solvent: hexane Z vinegar).

_, §Ω · 3εε) Ma Mine Mine氺'ε -

(¾xs-a: miz- ε each 粱 呦 ^ be ίί, ^ ρ i- d / ^ A

 ° SZl 'f l' ΟΖΖ '992' ΖΖΖ

ΐ) 6 · 8 '(ζΗ8 · ΐ = ί "' Ρ 'Ηΐ) ΐε · 8'(zHS'8 = f 'Ρ Ήΐ) 8Γ8' ( ^z H6''Z = f 'Ρ' Ηΐ) 68 · WL = i '' HT) S8 "Z '(ω' H2) S9" Z-ZS "Z '(ΖΗΖ · Ζ = ί" Ήΐ) ΖΥί' (ΖΗΖ · Ζ = ί "'Ρ Ήΐ) 9ΓΖ' (ΖΗ8 · ΐ

 . One. sw- whip

 ° (%

^ 8 * ¾ί) ^ ¾§ 呦 W eyes, 0 ^ (7 "[= 邈 4§7 total ^^ ^:瀚 缀 缀) 一

ふ つ 翻 ¾累

°

Two times

'V- / — ε—ベ

'V- / — ε—Be

 8 'ΐθΐ' 6Π 'SZl' 9fZ '392' f6Z 'TOS' ΙΖΖ

00 · 6 '( ^Ζ ΗΓ2 = Γ' Ρ ') LVS' ( ^Ζ Η2 · 8 = Γ 'Ρ Ήΐ) ΖΓ8' (ω Ήε) 88 · Ζ— 8Ζ · Ζ '(ω' HS) S9 "Z-0 VI

8·9呦 ί¾目、っ . One. 6SI- SSI: Whip

8 · 9 呦 ί¾ 目 、 っ

8L l £ / 900ZdT / 13d Washing with sopropyl ether gave the desired product (910 mg, 2.7 mmol) (yield 90%). Melting point: 231-232 ° C.

 NMR ^ vector (500MHz, CDC1) δ ppm: 1.30 (3H, s), 1.59 (3H, d, J = 1.4Hz), 5.

 Three

13 (IH, d, J = 4.8Hz), 6.66 (IH, d, J = 8.2Hz), 7.22-7.37 (4H, m), 7.52-7.55 (2H, m), 7.75 (IH, d, J = 7.6Hz), 7.82 (IH, d, J = 8.9Hz), 7.96 (IH, d, J = 2.1Hz), 8.66 (IH, d, J = 1.4Hz) ₀

Mass spectrum (m / z): 340 (M +), 325, 267, 247, 220, 211, 160.

 In the same manner as in Example 55, the following compound of Example 56 was synthesized.

Example 56

 3- (4, 4 Difluoro-1, 2 Hydroxy 1, 3, 3, Dimethyl 1, 2, 3, 4—Tetrahydride 1-yl isoquinoline) 2-Methoxyquinoline (Compound No. 3-212)

Melting point: 187 ° C.

^J H-NMR spectrum (500MHz, CDC1) δ ppm: 1.29 (3Η, s), 1.58 (3H, s), 4.21 (3H, br

 Three

s), 4.76 (IH, brs), 5.72 (IH, brs), 6.83 (IH, brs), 7.24-7.26 (IH, m), 7.32 (2H, q, J = 6.6Hz), 7.59 (2H, t , J = 7.6Hz), 7.69 (IH, d, J = 7.6Hz), 7.86 (IH, brs), 8.04 (IH, brs

).

Mass spectrum (m / z): 370 (M +), 355, 321, 297, 282, 211, 160.

Example 57

 3- (4,4-Difluoro-2-methoxy 3,3 dimethyl-1,2,3,4-tetrahydroisoquinoline-1-yl) quinoline (Compound No. 3-213)

3- (4,4 Difluoro-2 hydroxy-3,3 dimethyl 1,2,3,4-tetrahydroisoquinoline 1-yl) quinoline (50.3 mg, 0.15 mm) obtained in Example 55 (3) above Methyl iodide (0.01 mL, 0.22 mmol) was added dropwise to a dimethylformamide solution (lmL), and finally 60 wt% oily sodium hydride (8.8 mg, 0.22 mmol) was added, followed by stirring at room temperature for 30 minutes. did. After completion of the reaction, water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed once with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by thin layer chromatography (developing solvent: hexane Z ethyl acetate = 2Z1) to obtain the desired product (34.6 mg, 0.10 mmol) (yield 66.2%). 09 zone first

° ΠΖ 'LfZ Ί9Ζ' ΖΖ O 'Z9S ₊ n) zsz-(^ / ^ ^^^

ΐ) 9S"Z Ή ΐ) SS"Z

'Ρ 'Ηΐ) 8Γ3 '(ω Ή ΐ) wz-zvz '(ω 'HI) ors- 99 'Wi=f 'ρ Ήε) zs'i v\=[ 'ρ Ήε) ιτ\ '(ω'P' Ηΐ) SF8 '( ^s ' Ηΐ) Zl • 8

ΐ) 9S "Z Ή ΐ) SS" Z

'Ρ' Ηΐ) 8Γ3 '(ω Ή ΐ) wz-zvz' (ω 'HI) ors- 99' Wi = f 'ρ Ήε) zs'i v \ = [' ρ Ήε) ιτ \ '(ω

'Η ΐ · ΐ— 90 · ΐ Z'L = i' Ήε) 93 ： radd g (\ DQD ^ Ηη00) Η ^^ H NH _T

° 0. ΐ: Whip

 6S zone No.

'L Ί9Ζ' zzz '6εε' see '(+ ^) 89ε :( ^ζ / ω)> ^: Mu

'； 'Ηΐ) ' 'Ηΐ) Z'L 'P 'Ηΐ) 89·9 '(ZHS'S =f 'P 'Ηΐ) 8Γ3 '(ω 'Ηΐ) WZSVZ '(ω 'Ηΐ) 08 — W 'Wl=f 'P Ήε) ZS'I '(ζΗΐ

Ρ 'Ηΐ) ΐ · 8' (s Ήΐ) εΐ · 8 ΐ) ZS'L '(ω' Η SZ'Z— ΐΖ · 'Ή ΐ) ZS "Z

';' Ηΐ) '' Ηΐ) Z'L 'P' Ηΐ) 89 · 9 '(ZHS'S = f' P 'Ηΐ) 8Γ3' (ω 'Ηΐ) WZSVZ' (ω 'Ηΐ) 08 — W' Wl = f 'P Ήε) ZS'I' (ζΗΐ

 . 0 ^ 91- S9I: Whip

一 、^Ηエー (粱 is— ε- ^ Μ ^ »^ ίί ^ (/ y- 1—be fi ^ 'ε' z Ί

1 、 ^ Η

 8S zone No.

. > n 呦

ω 'ΗΖ) '； 'Ηΐ) '； 'Ηΐ) ' 'Ηΐ) Z'L

'P Ήε) 83"ΐ '(ζΗ ·ΐ=ί" 'P Ήε) 9ΖΊ： d g ( Q 'ZHWOOS ^ 匪 顺- H_T ° 6fl '09 ΐ '9ΖΖ' LfZ 'L9Z' 6SS ₊ n) f Z-^ / ^ ^^^ 'P' Ηΐ) Ζ8 ・ 8 '( ^s ' Ηΐ) 3Γ8 ΐ) fVS I) S8 "Z' (

ω 'ΗΖ)';'Ηΐ)';'Ηΐ)''Ηΐ)Z'L

'P Ήε) 83 "ΐ' (ζΗ · ΐ = ί"'P Ήε) 9ΖΊ: dg (Q' ZHWOOS ^ 匪 顺-H _T

. One. ε8ΐ: Whip

8L l £ / 900ZdT / 13d 3— (2 aralkyloxy 4,4 difluoro 1,3,3 dimethyl 1,2, 3, 4—tetrahydroisoquinoline 1—yl) quinoline (Compound No. 3—216)

Melting point: 134 ° C.

 1H-NMR spectrum (500MHz, CDCl) δ ppm: 1.28 (3H, d, J = 1.4Hz), 1.59 (3H, d, J =

 Three

 1.4Hz), 3.26-3.29 (IH, m), 3.96—3.99 (IH, m), 4.79-4.89 (2H, m), 5.22 (IH, d, J = 5.5 Hz), 5.35-5.40 (IH, m), 6.69 (IH, d, J = 7.6Hz), 7.26 (IH, t, J = 7.6Hz), 7.36 (IH, t, J = 7.6Hz), 7.57 (IH, t, J = 7.6Hz) , 7.72-7.75 (2H, m), 7.82 (IH, d, J = 8.2Hz), 8.13 (1

H, d, J = 7.6 Hz), 8.14 (IH, s), 8.85 (IH, d, J = 2.1 Hz).

Mass spectrum (m / z): 380 (M +), 365, 350, 339, 322, 309, 294.

Example 61

 3— (2 Benzyloxy— 4, 4 Difluoro 3, 3 Dimethyl— 1, 2, 3, 4—Tetrahydroisoquinoline— 1—yl) quinoline (Compound No. 3—217)

Physical properties: amorphous.

^J H-NMR spectrum (500MHz, CDCl) δ ppm: 1.29 (3H, d, J = 1.4Hz), 1.69 (3H, d, J =

 Three

 I.4Hz), 3.70 (IH, d, J = 9.6Hz), 4.49 (IH, d, J = 10.3Hz), 5.26 (IH, d, J = 5.5Hz), 6.70 (IH, d, J = 7.6 Hz), 6.77 (2H, t, J = 4.1Hz), 7.11—7.18 (3H, m), 7.27 (IH, t, J = 6.9Hz), 7.37 (IH, t, J = 7.6Hz), 7.59 ( IH, t, J = 7.6Hz), 7.74-7.77 (2H, m), 7.81 (IH, d, J = 8.2 Hz), 8.16 (IH, s), 8.17 (IH, d, J = 4.1Hz), 8.91 (IH, d, J = 2.1Hz).

Mass spectrum (m / z): 430 (M +), 415, 322, 307, 287, 266, 248.

Example 62

 3— (2 Acetoxy 4,4-difluoro-3,3 dimethyl-1,2,3,4-tetrahydr Oral isoquinoline—1-yl) quinoline (Compound No. 3-—218)

Melting point: 161-162 ° C.

 1H-NMR spectrum (500MHz, CDCl) δ ppm: 1.37 (3H, s), 1.50 (3H, d, J = 2.1Hz), 1.

 Three

 69 (3H, s), 5.37 (IH, brs), 6.71 (IH, d, J = 7.6Hz), 7.29 (IH, t, J = 7.6Hz), 7.40 (IH, t, J = 7.6Hz), 7.54 (IH, t, J = 7.6Hz), 7.71-7.74 (IH, m), 7.79 (2H, dd, J = 8.2, 11.7Hz), 8.11 (IH, d, J = 8.2Hz), 8.18 (IH , d, J = 2.1 Hz), 8.87 (IH, s).

Mass spectrum (m / z): 382 (M +), 340, 322, 310, 266, 247, 230. ° sfz 'Z9Z' HZ 'εεε' εθε ₊ n) sL £ ( ² / ^) Η ^^^

'Ηΐ) 0Γ8' (s Ήΐ) 80

'P 'Ηΐ) SS"9 '(^s 'Ηΐ) SFS ' P Ή ΐ) wz

'ρ Ήε) en '(^s Ήε) εε) 9S "Z '(ω Ή2) S6" 9-28 "9

'P' Ηΐ) SS "9 '( ^s ' Ηΐ) SFS' P Ή ΐ) wz

'ρ Ήε) en' ( ^s Ήε) εε

'； Ήε) S9 ： radd 9 ODOD Η Ν-Η_Τ • ΐ '(s Ήε) ΖΓΐ

'; Ήε) S9: radd 9 ODOD Η Ν-Η _Τ

. One. Whip

{zz ε

S9 category

° 8W 'sfz' Z9Z 'HZ' εεε 'βη' { ₊ η) ζ '-^ ΛΗ ^^^

'Ηΐ) 9S"Z '(ω 'Η2) 6·9— S8'9 ° (s' Ηΐ) SZ "8 '(zH6" 8 = f' P 'Ηΐ) 0Γ8' ( ^s Ή ΐ) 60

'Ηΐ) 9S "Z' (ω 'Η2) 6 · 9— S8'9

'ρ Ήε) β _T

ozz ε

 9th area

° S8 '8 ΐ' SfZ 'Ζ9Ζ' LLZ 'ΖΖΖ' ( ₊ η) 0 Ζ-^ / ^ ^^^

'Ρ 'Ηΐ) ZL'L '(ω Ήε) W L-W L '； 'Ηΐ) 0 S" '(ω 'ΗΖ) ΐ6·9— S8'9 '(^zH9"Z=f 'Ρ 'Ηΐ) ΐε·9 '(^s 'Ηΐ) 60"3 Ήε) W\ '(^ζΗΐ^=Γ° W \ = ['Ρ' Ηΐ) '(V

'Ρ' Ηΐ) ZL'L '(ω Ήε) W LW L';'Ηΐ) 0 S "' (ω 'ΗΖ) ΐ6 · 9— S8'9' ( ^z H9" Z = f 'Ρ' Ηΐ) ΐε · 9 '( ^s ' Ηΐ) 60 "3 Ήε) W \' ( ^ζ Ηΐ ^ = Γ

H N-H_T 'ρ Ήε) os "i' (s Ήε) 9ε · ΐ '( ^s Ήε) ΟΖΊ:

H NH _T

 ° Tsu 81-98Ϊ: Whip

ε9圏第 (# 6X2-ε

ε9 category

98

'Ρ 'Ηΐ) Zl'l 'Ηΐ) ZS'Z '(ω ' HS) fVL-SO'L '(ω 'ΗΖ) 6·9— S8'9

'Ρ 'Ηΐ) ZS"9 '(^s 'Ηΐ) ΖΖ^ '(ΖΗε·0ΐ=ί" 'Ρ 'Ηΐ) ZVf '(ΖΗε·0ΐ=ί" 'Ρ 'Ηΐ) ST '(s Ήε) 99·ΐ '(^ζΗΐ^=Γ 'Ρ Ήε) IS"! '(s Ήε) 9VI '(s Ήε) 6ΐ·ΐ：

H N-H_T 8L l £ / 900ZdT / 13d 60 · 8

'Ρ' Ηΐ) Zl'l 'Ηΐ) ZS'Z' (ω 'HS) fVL-SO'L' (ω 'ΗΖ) 6 · 9— S8'9

'Ρ' Ηΐ) ZS "9 '( ^s ' Ηΐ) ΖΖ ^' (ΖΗε · 0ΐ = ί"'Ρ' Ηΐ) ZVf '(ΖΗε · 0ΐ = ί "' Ρ 'Ηΐ) ST' (s Ήε) 99 · Ϊ́ '( ^ζ Ηΐ ^ = Γ' Ρ Ήε) IS "! '(S Ήε) 9VI' (s Ήε) 6ΐ

H NH _T

. One. ε8ΐ: Whip

 89th

° m 'Z9Z' 9LZ 'εεε' βη 'ezs' ( ₊ η) οβζ-(^ / ^ ^^^

° ( ^s ' Ηΐ) fLS '( ^z H6 "8 = f'

'P 'Ηΐ) ZS'L '(ω 'Ηΐ) SZ"Z-69"Z '； Ή ΐ) 9S'Z '(ω 'ΗΖ) 6·9— 8·9 '(^zH9"Z=f 'Ρ 'Ηΐ) 9S"9 '(ω 'Ηΐ) 8S'S— OS'S 'Ηΐ) OS'SP 'Ηΐ) 0Γ8' (s Ήΐ) 60

'P' Ηΐ) ZS'L '(ω' Ηΐ) SZ "Z-69" Z '; Ή ΐ) 9S'Z' (ω 'ΗΖ) 6 · 9— 8 · 9' ( ^z H9 "Z = f 'Ρ' Ηΐ) 9S "9 '(ω' Ηΐ) 8S'S— OS'S 'Ηΐ) OS'S

'(ω Ήζ)

H N-H_T 'Ρ Ήε) 6VI' (s Ήε) 92Ί '(s Ήε) SVI:

H NH _T

. JSI: Whip

(zz-ε

 → '£' Ζ Λ-Λ ^ ^ ^ → '' ε '£-: /:--^^ -Z)-£

° 6W 'sfz' Z9Z 'HZ' εεε 'ζζε' { ₊ η) ζ ^ ζ '-^ ΛΗ ^^^

'； 'Ηΐ) S'Z '(ω 'ΗΖ) S6"9-28"9 '(^zH9"Z=f 'P 'Ηΐ) Γ9 '(^s 'Ηΐ) 9Γ3 '(ω 'Ηΐ) 6S'S- SS'S '(ω° ( ^s ' Ηΐ) fLS '( ^Ζ Η2 · 8 = Γ' Ρ 'Ηΐ) 0Γ' (s Ήΐ) Ζ0 "8

';' Ηΐ) S'Z '(ω' ΗΖ) S6 "9-28" 9 '( ^z H9 "Z = f' P 'Ηΐ) Γ9' ( ^s ' Ηΐ) 9Γ3 '(ω' Ηΐ) 6S'S- SS'S '(ω

'HI) L ^ ZZ ^ Z' ( ^s Ήε) 09 · ΐ '( ^ζ ΗΓ ^ = Γ' ρ Ήε) 8 ΐ '( ^s Ήε) εε · ΐ' ( ^s Ήε)

H N-H_T 'Ηΐ) 60 · ΐ— 00 · ΐ

H NH _T

. One. 8W- ΐ: Whip zzz-ε Each 粱 呦 ^ ベ ίί, ^ ρ (/ y- i- d / ^ ^

 99 zone first

'P 'Ηΐ) ZL'f '(^s 'HS) ZZ'Z '(^ζΗΐ·

8L l £ / 900ZdT / 13d

'P' Ηΐ) ZL'f '( ^s ' HS) ZZ'Z' ( ^ζ Ηΐ

 . One. S9I- 9ΐ: Whip

No. 1

° 96ΐ 'ΟΖΖ' LfZ Ί9Ζ 'fSZ' l- ₊ n) ZZZ: (z / ui) mu

° (ζΗ8 · ΐ = ί "'Ρ' Ηΐ) 8 · 8 '(ΖΗ9 · 8 = 1"' Ρ Ή ΐ) ΐΐ · 8 '(ΖΗ8 · ΐ = ί "' Ρ 'Ηΐ) ΐ0 · 8' ( ω Ήε) ZS'L-IL'L

'Ρ 'Ηΐ) IV '( s-iq 'ΗΪ) 06· ΐ '(s Ήε) 8ε·ΐ '(^s Ήε) ζε·ΐ: a g (^ε ιつ 'ZH OOS)

'' Ηΐ) 6S "Z

'Ρ' Ηΐ) IV '(s-iq' ΗΪ) 06 · ΐ '(s Ήε) 8ε · ΐ' ( ^s Ήε) ζε · ΐ: ag ( ^ε ι one 'ZH OOS)

- ε . One. 06 ΐ: Whip τ—Be ίί ^ One 'ε' ζ

-ε

No. 1

° Z9Z 'LLZ' 682 'LIZ' ZZZ 'OSS' (+ W) S6S: ( ^ζ / ω) m

' 'Ηΐ) SS"Z '(ω 'ΗΖ) 96·9— 98·9 '(^zH9"Z=f 'Ρ 'Ηΐ) Ζε·9 '(^s 'Ηΐ) ΖΖ^ '(^S'HT) ZU\ '(^s Ήε) 29"ΐ '(^ζΗΐ^=Γ 'Ρ Ήε) Ζ '1 '(s Ήε) 9ΖΊ '(^s Ήε) ΖΊ ：

H N-H_T ° ( ^s 'Ηΐ) ΐ8 ・ 8' ( ^s 'Ηΐ) 60 ・ 8'(zHS'8 = f 'Ρ' Ηΐ) 80 ・ 8

'' Ηΐ) SS "Z '(ω' ΗΖ) 96 · 9— 98 · 9 '( ^z H9" Z = f' Ρ 'Ηΐ) Ζε · 9' ( ^s ' Ηΐ) ΖΖ ^ '( ^S ' HT) ZU \ '( ^s Ήε) 29 "ΐ' ( ^ζ Ηΐ ^ = Γ 'Ρ Ήε) Ζ' 1 '(s Ήε) 9ΖΊ' ( ^s Ήε) ΖΊ:

H NH _T

. One. S9I: Whip

 69 zone

° Lfl 'Z9Z' 9LZ 'Ζ Ζ' 89S 'Zf' ( ₊ η) 0 (^ / ^) ^^^

° ( ^s 'Ηΐ) 08 ・ 8' ( ^Ζ Η2 ・ 8 = Γ 'Ρ' Ηΐ) ZVS '( ^s ' Ηΐ)

88

8.M7lC / 900Zdf / X3d 6Hz), 7.29 (IH, t, J = 7.6Hz), 7.54 (IH, t, J = 7.6Hz), 7.68-7.74 (2H, m), 7.80 (IH, d, J = 8.2Hz), 8.09 ( IH, s), 8.10 (IH, d, J = 8.9 Hz), 8.85 (IH, d, J = 2.1 Hz).

Mass spectrum (m / z): 338 (M ⁺ ), 323, 267, 247, 210, 160, 72.

[0162] Formulation Example 1

 Powder

The compound of Example 1 (1.0 wt _^0/0), Doriresu A (alkyl ether phosphate, Japan Kayaku Co., Ltd., 0.4 wt%), Carplex # 80- D (white carbon, Shionogi (Giyaku Pharmaceutical Co., Ltd., 1.5% by weight), calcium carbonate (Adachi Lime Co., Ltd., 0.5% by weight), and Keiwa clay-style steel (Keiwa Furnace Co., Ltd., 32.1% by weight) , And then pulverized with an Eco Sample サ ン プ ル —Type 1 (Nonmar Mill), manufactured by Fuji Padal Co., Ltd. Wako Furnace Co., Ltd.) was added and mixed to obtain a powder DL.

[0163] Formulation Example 2

 Emulsion

The compound of Example 2 (10 wt%) was dissolved in a mixed solution of xylene (manufactured by Wako Pure Chemical Industries, Ltd., 40 wt%) and D MSO (manufactured by Wako Pure Chemical Industries, Ltd., 35 weight _^0/0), the solution Parako 1KPS (a mixture of a surfactant and a nonionic surfactant, 25% by weight, manufactured by Nippon Emulsifier Co., Ltd.) was added and mixed to obtain an emulsion.

[0164] Formulation Example 3

 Wettable powder

The compound of Example 3 (1 wt _^0/0), Carplex # 80- D (10 wt _^0/0), Gohsenol GL05 (poly Bulle alcohol, Nippon Synthetic Chemical Industry Co., 2 weight ⁰ /.), The two Yukoru 29 IPG (dioctylsulfosuccinic acid sodium salt, manufactured by Nippon Emulsifier Co., Ltd., 0.5% by weight), neogen powder (linear alkylbenzene sulfonic acid sodium salt), manufactured by Daiichi Kogyo Seiyaku Co., Ltd., 5% by weight), Radiolite # 200 (fired diatomaceous earth), Showa Chemical Industry Co., Ltd., 10 wt%) and H derivative (Kaolinite clay), Keiwa Furnace Co., Ltd., 71.5 wt%) The sample KII-1 was pulverized to obtain a wettable powder.

[0165] Formulation Example 4 Granule

 Compound of Example 4 (2% by weight), sodium tripolyphosphate (Mitsui Chemicals Co., Ltd., 2% by weight), Amicol NO. 1 (dextrin, Nippon Starch Chemicals Co., Ltd., 1.5% by weight) ), Bentonite (Toyoshun Mining Co., Ltd., 25% by weight) and Calhin 600 (Calcium carbonate, Adachi Lime Co., Ltd., 69.5% by weight) are mixed, Dome Gran (Fuji Baudal Co., Ltd., screen) Extrusion granulation was performed using 0.9 mm φ). The resulting granulated product was dried with a shelf-type dryer (manufactured by Tabai Co., Ltd., PERFECT OVEN PS-222 type, 60 ° C), and then sieved to 600 to 1180 m to obtain granules. .

Test example 1

 Rice, rice blast control trial (therapeutic effect)

 The plant cultivation test plant (rice: Kofu) in the 3rd to 4th leaf stage was spray-inoculated with the pathogen spore suspension, and the pot was placed in an inoculation room with a room temperature of 20-23 ° C to promote disease. The compound of the present invention was dissolved in a dimethylsulfoxide methanol mixed solution (volume ratio: 7Z3) to prepare a spray solution containing 300 ppm of the compound of the present invention and sprayed uniformly in the pot. The severity of the disease 7 days after vaccination was investigated. The test was performed in duplicate.

 In addition, the disease severity was determined by the following criteria by visually observing the disease severity of the test plant, and expressed in 4 stages from 0 to 3.

 Disease severity is 0: No disease at all!

 Disease severity is 1: The disease severity is less than 40% of the untreated area.

 Disease severity is 2: The disease severity is 40% or more and less than 80%.

 Disease severity is 3: The disease severity is 80% or more.

As a result of this test, Example 4 (Compound No. 1-10), Example 7 (Compound No. 1 35), Example 14 (Compound No. 1-56), Example 15 (Compound No. 1-77) Example 18 (Compound number 1-100), Example 19 (Compound number 1-123), Example 20 (Compound number 1-129), Example 21 (Compound number 1-130) Example 22 (Compound No. 1-131), Example 23 (Compound No. 1-132), Example 24 (Compound No. 1-133), Example 25 (Compound No. 1-135) Example 26 (Compound number 1-165), Example 27 (Compound number 1-166), Example 28 (Compound number 1-167), Example 30 (Compound number 1-166) — 170), Example 31 No. 1-173), Example 32 (Compound No. 1-172), Example 33 (Compound No. 1-177), Example 34 (Compound No. 1-178), Example 35 (Compound No. 1— 185), Example 40 (Compound No. 2-89), Example 44 (Compound No. 3-100), Example 46 (Compound No. 3-133), Example 47 (Compound No. 3-167), Compound of Example 48 (Compound No. 3-170), Example 50 (Compound No. 1 206), Example 51 (Compound No. 1121), Example 52 (Compound No. 1-212), In Example 55 (Compound No. 3-211), Example 63 (I Compound No. 3-219), and Example 71 (I Compound No. 3-226), the disease severity was 0.

Test example 2

 Tomato gray mold control test (preventive effect)

 Dispersion solution containing 300 ppm of the compound of the present invention by dissolving the drug substance in dimethyl sulfoxide and methanol (volume ratio 7: 3) in a pot cultivation test plant in the 2nd to 3rd leaf stage (tomato: large-scale Fushou) Was sprayed uniformly. After cultivating for 1 day, the pot was spray-inoculated with the pathogen spore suspension, and the pot was placed in an inoculation room with a room temperature of 20-23 degrees to promote disease. The severity of the disease 2 days after vaccination was investigated. The test was performed in duplicate.

 In addition, the disease severity was determined by the following criteria by visually observing the disease severity of the test plant, and expressed in 4 stages from 0 to 3.

 Disease severity is 0: No disease at all!

 Disease severity is 1: The disease severity is less than 40% of the untreated area.

 Disease severity is 2: The disease severity is 40% or more and less than 80%.

 Disease severity is 3: The disease severity is 80% or more.

As a result of this test, Example 1 (Compound No. 1 198), Example 15 (Compound No. 1 77), Example 16 (Compound No. 1-78), Example 19 (Compound No. 1-123), Example 20 (Compound number 1-129), Example 21 (Compound number 1-130), Example 22 (Compound number 1-131), Example 24 (Compound number 1-130) -133), Example 25 (Compound No. 1-135), Example 26 (Compound No. 1 165), Example 28 (Compound No. 1 167), Example 30 (Compound No. 1) 1170), Example 31 (Compound No. 1 173), Example 32 (Compound No. 1 172), Example 35 (Compound No. 1-185), Example 41 (Compound No. 2-112), Implementation Example 45 (Y compound number 3-123), Example 46 (Y compound number 3-133), Example 48 (Y compound number 3-170) Example 50 (Compound No. 1 206), Example 55 (Compound No. 3-211), Example 63 (Compound No. 3-219) and Example 71 (Compound No. 3-226) The disease severity was 0.

Industrial applicability

 The 3- (isoquinoline-1-yl) quinoline derivative or a salt thereof, which is a compound of the present invention, can be used as an agrochemical composition, in particular, as an agricultural and horticultural fungicide, and does not damage host plants. It is effective against various phytopathogenic fungi, especially rice blast, and is an excellent agricultural and horticultural fungicide.

 The plant diseases for which the compound of the present invention exhibits excellent efficacy are, for example, rice blast (Pyricularia oryzae) and gray mold (Botrytis cin erea) of cucumber, tomato and kidney beans. The bactericidal spectrum is not limited to these diseases

Claims

The scope of the claims  -General formula

 (I) (Where  Ring A and ring B may be the same or different  An optionally substituted benzene ring; an optionally substituted C 1 -C cycloalkyl ring (  3 8 Wherein the cycloalkyl ring may be partially unsaturated); or an optionally substituted 1 to 4 identical or different rings from which the group forces comprising oxygen, nitrogen and sulfur forces are also selected. Represents a 5- to 6-membered heteroaryl ring containing the constituent heteroatoms, wherein the heteroaryl ring is partially hydrogenated! / R ³ and R ⁴ may be the same or different  From hydrogen atom; neuron atom; neuron atom, c to c alkoxy group and phenoxy group  1 6 A group force that may be substituted with 1 to 3 substituents of the same or different ones selected from c to c alkyl groups; hydroxyl groups; rho, rogen atoms, c to c alkoxy groups, and phenoxy groups. 1 6 1 6 The group force may also be substituted with 1 to 3 substituents of the same or different one selected from a ~ C alkoxy group; a norogen atom, a C 1 -C alkoxy group and a phenoxy group. 1 6 1 6 Group power selected by the same or different selected 1 to 3 substituents, C  1 ~ C alkylthio group; consisting of a norogen atom, a C ~ C alkoxy group and a phenoxy group 6 1 6 Group power may also be substituted with the same or different 1 to 3 substituents selected C ~  1 C alkylsulfinyl group; whether it is a norogen atom, a C to C alkoxy group or a phenoxy group 6 1 6 May be substituted with 1 to 3 substituents which are the same or different, and may be substituted with 1 to 3 C alkylsulfol groups; a norogen atom, a C to C alkoxy group and a phenoxy group. Substituted with 1 to 3 identical or different substituents C to c cycloalkyl group; a norogen atom, c to c alkoxy group and phenoxy 3 6 1 6 Group power as basic force C 1 -C cycloalkyloxy group which may be substituted with the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and a phenol 3 6 1 6 Noxy group power Group power C 1 -C cycloalkylthio group optionally substituted by the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and  3 6 1 6 Phenoxy group force Group power C 1 -C alkenyl group optionally substituted by 1 to 3 selected or different substituents; a norogen atom, a C 1 -C alkoxy group and a phenyl group  2 6 1 6 Noxy group strength Group force C 1 -C alkoxy group optionally substituted by the same or different 1 to 3 substituents selected; a nitrogen atom, C 1 -C alkoxy group and  2 6 1 6 ヱ Noxy group force Group force C 1 -C alkenylthio group optionally substituted by the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and  2 6 1 6 Phenoxy group force Group force C 1 -C alkyl group optionally substituted by 1 to 3 identical or different substituents selected; a nitrogen atom, a C 1 -C alkoxy group and a phenyl group  2 6 1 6 Noxy group force Group force C 1 -C alkyloxy group optionally substituted by 1 to 3 identical or different substituents selected; a nitrogen atom, C 1 -C alkoxy group and  2 6 1 6 ヱ Noxy group power Group force Selected C to C alkylthio group optionally substituted with 1 to 3 different substituents; Nonogen atom, same or different 1 to 3  2 6 C to c alkyl group, c to c alkoxy group,  1 6 1 6 May be substituted with one or different 1 to 2 C 1 -C alkyl or acyl.  1 6 Iamino group, nitro group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group  1 6 Group power also may be substituted with the same or different 1 to 6 substituents selected; aryl group; a norogen atom, optionally substituted with 1 to 3 different halogens C -C alkyl group, C -C alkoxy group, 1 to 2 identical or different (amino group, nitro group, cyano optionally substituted by DC -C alkyl or acyl) 1 6 Group, hydroxyl group, mercapto group and c-c alkylthio group power  1 6 Alternatively, it may be substituted with 1 to 6 different substituents, or an aryloxy group; a nitrogen atom, C 1 to C 6 optionally substituted with 1 to 3 different halogens 16 alkyl group, C to C alkoxy group, the same or different 1 to 2 C to C alkyl group Or an amino group, nitro group, cyano group, hydroxyl group, mercapto group and C to C alkylthio group which may be substituted with asil group power of the same or different 1 to 6 selected  1 6 A arylthio group; a halogen atom, a C 1 -C alkyl group which may be substituted with 1 to 3 halogen atoms, the same or different, and a C 1 -C alkoxy group Force Heteroaryl group optionally substituted with the same or different 1 to 6 substituents selected; Nonogeneous atom, optionally substituted with 1 to 3 different halogens C to C Alkyl group and C to C alkoxy group force is also selected heteroalkyloxy group optionally substituted by the same or different 1 to 6 substituents; a norogen atom, the same or different 1 to 3 A group force consisting of a C 1 -C alkyl group and a C 1 -C alkoxy group optionally substituted with halogen, which is selected from the same or different 1 to 6 substituents, and may be heteroarylthioA group; a norogen atom, substituted with 1-3 identical or different halogens, C-C alkyl groups, C-C alkoxy groups, identical or different 1-2 C-C 1 6 1 6 1 6 Amino group, nitro group, cyano group, hydroxyl group which may be substituted with alkyl or acyl , A mercapto group and a c to c alkylthio group force are also selected, the same or different  1 6 Aralkyl group which may be substituted with 1 to 6 substituents; halogen atom, C to C alkyl group which may be substituted with 1 to 3 different halogens, C to C  1 6 1 6 alkoxy group, identical or different 1 to 2 C 1 -C alkyl or acyl  1 6 Optionally substituted amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c  1 6 alkylthio group power group power selected Aralkyloxy group which may be substituted with 1 to 6 substituents which may be the same or different; a norogen atom, substituted with 1 to 3 halogens which may be the same or different C 1 -C alkyl group, C 1 -C alkoxy group, the same or different 1 to 2 C 1 -C alkyl or acyl may be substituted  1 6 From amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkylthio group  1 6 Or a group force selected from 1 to 6 substituents selected from the same or different, and may be an aralkylthio group; an acyl group; an acyloxy group; an acylthio group; or a cyano group, or ^{Two of} R ² , R ³ and R ⁴ are taken together to form a halogen atom, c-c alkyl. Group, c to c alkoxy group and phenoxy group force are also selected the same or different 1 6 A C 1 -C cycloalkyl ring optionally substituted with 1 to 3 substituents (wherein  3 8 The chloroalkyl ring may contain 1 to 3 heteroatoms selected from the group forces of oxygen, nitrogen and sulfur), or R ¹ and R ² ; or R ³ and R ⁴ are , Taken together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ^{4 taken} together represent a methylene group, or R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ together represent a single bond, Q is a nitrogen atom or a formula N—R ⁵ group (wherein R ⁵ is a hydrogen atom; a hydroxyl group; an amino group optionally substituted by the same or different 1 to 2 C 1 -C alkyl or acyl,  1 6 Halogen atoms, c-c alkoxy groups and phenoxy groups  1 6 Or a C 1 -C alkyl group optionally substituted with 1 to 3 different substituents;  1 6 Atoms, c to c alkoxy groups, and phenoxy group forces are the same or selected  1 6 C 1 -C alkoxy group optionally substituted with 1 to 3 different substituents;  1 6 The same or different group forces are also selected. 1 6 A C 1 -C alkylsulfinyl group optionally substituted with 1 to 3 substituents;  1 6 Gen atom, c-c alkoxy group and phenoxy group power  1 6 Is a C 1 -C alkylsulfonyl group optionally substituted with 1 to 3 different substituents;  1 6 Halogen atoms, c-c alkoxy groups and phenoxy groups  1 6 Or a C 1 -C alkyl sulfamo optionally substituted with 1 to 3 different substituents.  1 6 Selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 C 1 -C alkenyl optionally substituted with 1 to 3 identical or different substituents  2 6 oxy group; selected from the group forces of a norogen atom, c to c alkoxy group and phenoxy group  1 6 C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents 26 Roxy group; a C atom-alkyl group, a C-C alkoxy group, a C-C alkoxy group, which may be substituted with the same or different 1 to 3 halogen atoms, the same or different 1 to 2 c to c An amino group optionally substituted by alkyl or acyl, a nitro group, a cyan group, 1 6 Hydroxyl group, mercapto group and C-C alkylthio group  1 6 Is an aralkyl group optionally substituted with 1 to 6 different substituents; a norogen atom, a C 1 to C alkyl group optionally substituted with 1 to 3 identical or different halogens A C to C alkoxy group, the same or different 1 to 2 C to C alkyl or 1 6 1 6 An amino group optionally substituted by a sil, a nitro group, a cyano group, a hydroxyl group, a mercapto group, and C-C alkylthio group power group power chosen 1-6 identical or different substitutions 1 6 Substituted with a group may be an aralkyloxy group; an acyl group; an acyloxy group; tri- (C  1 -C alkyl) silyl group; or G (C1-Calkoxy) phosphoryl group. Represents 6 1 6 X may be the same or different when n is an integer from 2 to 4  A halogen atom; from the group consisting of a norogen atom, a C to C alkoxy group and a phenoxy group  1 6 C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents selected  1 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 C 1 to C cycloalkyl optionally substituted with 1 to 3 identical or different substituents  3 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 C 1 -C alkenyl optionally substituted with 1 to 3 identical or different substituents  2 6 groups; the same selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 A C 1 -C alkyl group optionally substituted with one or different 1 to 3 substituents;  2 6 Substituted with 1 to 3 halogen atoms, the same or different! /, C  1 ~ C alkyl group, C ~ C alkoxy group, same or different 1-2 C ~ C al 6 1 6 1 6 Amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkylthio group which may be substituted with a kill or acyl group group power of the same or different selected  1 6 An aryl group which may be substituted with 1 to 6 substituents; a halogen atom, a C to C alkyl group and a C to C alkoxy group which may be substituted with the same or different 1 to 3 halogens Group force selected heteroaryl group optionally substituted with 1 to 6 substituents of the same or different selected; a nonogen atom, a C to C alkoxy group and a phenoxy group  1 6 C group power is selected C-C alkoxy group which may be substituted with the same or different 1 to 3 substituents selected; group atom consisting of a nonogen atom, C-C alkoxy group and phenoxy group selected C 1 -C alkylthio group which may be substituted with the same or different 1 to 3 substituents; the same or different 1 to 3 group forces consisting of a nonogen atom, a C 1 -C alkoxy group and a phenoxy group are also selected May be substituted with Tiji-c alkyl sulfier group; neurogen atom, c-c alkoxy group and phenoxy 1 6 1 6 C group power is C-C alkylsulfonyl group optionally substituted by the same or different 1 to 3 selected substituents; 1 to 2 C to C alkyls which are the same or different  1 6 1 6 substituted with a kill group or an acyl group may be an amino group; an acyl group; a cyan group; or C  1 C alkyl group, c to c alkyl group, c to c alkyl group, aryl group and hetero 6 2 6 2 6 Represents the N-hydroxy (C to C alkane) imidoyl group in which the hydrogen atom of the hydroxyl group may be substituted with the selected substituent.  1 6  Y may be the same or different when m is an integer of 2 to 6,  A halogen atom; from the group consisting of a norogen atom, a C to C alkoxy group and a phenoxy group  1 6 C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents selected  1 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 C 1 to C cycloalkyl optionally substituted with 1 to 3 identical or different substituents  3 6 kill group; selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 C 1 -C alkenyl optionally substituted with 1 to 3 identical or different substituents  2 6 groups; the same selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group  1 6 A C 1 -C alkyl group optionally substituted with one or different 1 to 3 substituents;  2 6 Substituted with 1 to 3 halogen atoms, the same or different! /, C  1 ~ C alkyl group, C ~ C alkoxy group, same or different 1-2 C ~ C al 6 1 6 1 6 Amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkylthio group which may be substituted with a kill or acyl group group power of the same or different selected  1 6 An aryl group which may be substituted with 1 to 6 substituents; a halogen atom, a C to C alkyl group and a C to C alkoxy group which may be substituted with the same or different 1 to 3 halogens Group force selected heteroaryl group optionally substituted with 1 to 6 substituents of the same or different selected; a nonogen atom, a C to C alkoxy group and a phenoxy group  1 6 C group power is selected C-C alkoxy group which may be substituted with the same or different 1 to 3 substituents selected; group atom consisting of a nonogen atom, C-C alkoxy group and phenoxy group selected A C 1 -C alkylthio group optionally substituted with 1 to 3 identical or different substituents; a nonogen atom, a C 1 -C alkoxy group and a phenoxy group May be substituted with the same or different 1 to 3 substituents selected, C 1 to C alkyl sulfier groups; norogen atoms, C 2 to C alkoxy groups and phenoxy groups C 1 -C alkyl sulfonyl group optionally substituted with 1 to 3 identical or different substituents selected; 1 to 2 C 1 to C alkyls identical or different  1 6 16 substituted with a kill group or an acyl group may represent an amino group; an acyl group; a cyan group; or a hydroxyl group;  n represents an integer of 0 to 4,  m represents an integer of 0 to 6,  A bond including a dotted line represents a single bond or a double bond,  In the case where the bond including Q and the dotted line is a single bond, the bond including the other dotted line represents a single bond. )  Or a salt thereof. [2] Ring A may be substituted, benzene ring, C 1 -C cycloalkyl ring or pyridine  5 6  The compound or a salt thereof according to claim 1, which is a ring. [3] The compound or a salt thereof according to claim 1, wherein ring A is substituted! Or a benzene ring.  [4] Ring B may be substituted !, but may be a benzene ring, thiophene ring, oxazole ring, thiazole ring, pyridine ring, pyrazine ring, oxazine ring, dihydrooxazine ring, cyclopentane ring or cyclo The compound or salt thereof according to any one of claims 1 to 3, which is a hexane ring.  [5] The compound or a salt thereof according to any one of claims 1 to 3, wherein ring B is substituted! Or is a benzene ring, a pyridine ring or a dihydrooxazine ring.  [6] The compound or a salt thereof according to any one of claims 1 to 3, wherein Ring B is an optionally substituted benzene ring or pyridine ring. [7] R \ R ² , R ³ and R ⁴ forces Hydrogen atom; Norogen atom; C 1 -C alkyl group optionally substituted with 1 to 3 identical or different halogen atoms; Hydroxyl group; C alkoxy group  1 6 1 6  C to c alkylthio group; c to c alkylsulfier group; c to c alkylsulfo-; 1 4 1 4 1 4 C-C cycloalkyl group; C-C cycloalkyloxy group; C-C cycloalkyl Kirthio group; c to c-alkyl group; c to c-alkoxy group; c to c-alkyl group 2 6 2 6 2 4 C-c alkyl group; c-c alkyloxy group; c-c alkylthio  2 4 2 4 2 4 A group; a halogen atom, a C to C alkyl group, a C to C alkoxy group, which may be substituted with the same or different 1 to 3 halogen atoms, or the same or different 1 to 2 C to  1 4 1 4 1 Amino group, nitro group, cyano group, water optionally substituted with C alkyl or acetyl 2 Acid group, mercapto group, and c-c alkylthio group group force also selected same or  14 A phenyl group or a naphthyl group, which may be substituted with 1 to 3 different substituents; a nitrogen atom, a C to C alkyl group, a C to C alkoxy group and a C to C alkylthio group;  1 4 1 4 1 4 Force group force Selected phenoxy group optionally substituted by the same or different 1 to 3 substituents selected; a nonogen atom, a C to C alkyl group, a C to C alkoxy group and C ~  1 4 1 4 1 C alkylthio group force can also be selected with the same or different 1 to 3 substituents Four Optionally substituted phenylthio group; a neurogen atom, a c-c alkyl group and c-c  1 4 1 Alkoxy group force Group force Substituted with the same or different 1 to 3 selected substituents Four Furyl group, chael group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, pyridyl group, viridyl group or pyridyl group; norogen atom, c to c Consists of an alkyl group and a c to c alkoxy group  1 4 1 4 Group power also may be substituted with the same or different 1 to 3 substituents, which may be substituted with a fluoroxy group, a ceroxy group or a pyridyloxy group; a norogen atom, a C to C alkyl group  1 to 4 groups and C to C alkoxy group forces are the same or different one to three selected  14 A furylthio group, a thiol group or a pyridylthio group, which may be substituted with the above-mentioned substituents; a halogen atom, a C 1 to C alkyl group which may be substituted with the same or different 1 to 3 halogen atoms, C ~ C alkoxy group, same or different 1-2 C ~  1 4 1 4 1 C-alkyl or acetyl substituted amino group, nitro group, cyan group, water 2 Acid group, mercapto group, and c-c alkylthio group group force also selected same or  14 A benzyl group, a phenethyl group, a diphenylmethyl group or a naphthylmethyl group, which may be substituted with 1 to 3 different substituents; a no, a rogen atom, a c to c alkyl group, a c to c  1 4 1 4 Alkoxy group and c to c alkylthio group power Group power selected Same or different  14 Benzyloxy group or phenethylo which may be substituted with 1 to 3 substituents A xyl group; a nitrogen atom, a c-c alkyl group, a c-c alkoxy group and a c-c alkyl group 1 4 1 4 1 4 Ruthio group power Group power chosen Benzylthio group or phenethylthio group optionally substituted with 1 to 3 identical or different substituents; formyl group, C to C alkyl  2 7 carbo group, c to C alkenyl carbonate group, benzoyl group, naphthoyl group, C to C  3 7 2 C alkoxycarbonyl group, c-c alkylthiocarbol group or c-c alkyl 7 2 5 2 7 luminocarbol group; c to c alkylcarboxoxy group, c to c alkoxycar  2 5 2 7 Boroxy group or c-c alkylaminocarboxoxy group; c-c alkyl force  2 7 2 5 A thiolthio group, a c-c alkoxycarbothio group or a c-c alkylamino group.  2 5 2 5 A force that is a thiol-thio group; or a cyano group, Rukill

Group, c-c alkoxy group and phenoxy group power is the same or different selected 14 Or form a C to C cycloalkyl ring optionally substituted with 1 to 3 substituents.  3 6 Or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent a methylene group Or R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ forces together to represent a single bond or a compound according to any one of claims 1 to 6 Its salt. R ² , R ^3, and R ⁴ may be substituted with 1 to 3 identical or different substituents selected from a hydrogen atom, a halogen atom, a fluorine atom, a chlorine atom, and a bromine atomic force. ~ C alkyl group; hydroxyl group; methoxy group; methylthio group; methanesulfinyl group; 14 Tan sulfonyl group; c to c cycloalkyl group; c to c alkyl group; c to c alkyl group 3 6 2 3 2 3 group; fluorine atom, chlorine atom, methyl group and methoxy group force group power selected by the same or different 1 to 3 substituents, which may be substituted Group; phenoxy group; phenylthio group; flinyl group, chenyl group or pyridyl group; fluorine atom, chlorine atom, methyl group and methoxy group force group power of the same or different selected one to three substituents Benzyl group; benzyloxy group; benzylthio group; formyl group, C  2 ~ C alkyl carbo group, c ~ c alkoxy carbo group or c ~ c alkyl 3 2 3 2 3 amino carbonyl group; acetyloxy group, c to c alkoxy carboxy group or  twenty three a force that is a c to c alkylaminocarboxoxy group; an acetylylthio group; or a cyano group; Or Form cycloalkyl ring

Or R ¹ and R ² ; or R ³ and R ⁴ forces together to represent an oxo group, or R ¹ and R ² ; or R ³ and R ⁴ forces together, to form a methylene group. Or R ¹ and R ³ or R ⁴ ; or R ² and R ³ or R ⁴ forces together to represent a single bond or a compound according to any one of claims 1 to 6 or a compound thereof salt. [9] Kill group or chloroalkyl ring

 The compound or salt thereof according to any one of claims 1 to 6, which is formed. [10] The alkyl group according to claims 1 to 6, which is an alkyl group

 The compound or a salt thereof according to any one of the above. [11] R ² , R ³ and R ⁴ are a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group or an ethyl group,

The compound according to any one of claims 1 to 6, wherein two of R ² , R ³ and R ⁴ are combined together to form a cyclobutyl ring, a cyclopentyl ring or a cyclohexyl ring. Its salt. [12] Q is a nitrogen atom or a group of formula N—R ⁵ (wherein R ⁵ is a hydrogen atom; a hydroxyl group; the same or different one or two C 1 to C alkyl or acetyl groups may be substituted. Good amino group,  1 2  Group powers selected from the group consisting of C, C, C and C alkoxy groups, and phenoxy groups  1 2  Or a C 1 -C alkyl group optionally substituted with 1 to 3 different substituents;  14  Group force that also has a C atom, a c to c alkoxy group, and a phenoxy group force  1 2  A C 1 -C alkoxy group optionally substituted with 1 to 3 different substituents; a fluorine atom,  14  Chlorine atom and C-C alkoxy group power Group power chosen Same or different 1-3  1 2  C to c alkylsulfinyl group optionally substituted by one substituent; fluorine atom, salt  1 2  Elementary atom and C-C alkoxy group power Group force Selected 1 to 3 identical or different  1 2  C to c alkylsulfonyl group optionally substituted by a substituent of: fluorine atom, chlorine atom  1 2  Child and C-C alkoki group power is the same or different one to three positions selected  1 2  C to C alkylsulfamoyl group optionally substituted by a substituent; a neurogen atom, C to C  1 2 1 C alkoxy group and phenoki group power group power selected 1 to 3 identical or different Optionally substituted with a substituent of c to c-alkoxy group; a norogen atom, c to c  2 4 1 Alkoxy group and group force that is also a phenoxy group force is also selected 1 to 3 same or different 2 May be substituted with substituents c to c alkyloxy groups; norogen atom, same or young  twenty four Is a C 1 -C alkyl group optionally substituted with 1 to 3 different halogens,  1 2 1 2 Lucoxy group, 1 to 2 C 1 -C alkyl or acetyl substituted with the same or different  1 2 Optionally substituted amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c  1 2 Lukiruthio group power Group force Benzyl group or phenethyl group optionally substituted with 1 to 3 selected or different substituents; nonogen atom, same or different 1 to 3 halogen atoms C-C alkyl group optionally substituted with C-C alkoxy  1 2 1 2 group, substituted with 1-2 identical or different C 1 -C alkyl or acetyl  1 2 Amino group, nitro group, cyano group, hydroxyl group, mercapto group and c to c alkyl group  1 2 基 group strength group force benzyloxy group or phenethyloxy group optionally substituted by the same or different 1 to 3 selected substituents; formyl group, C 1 -C alkyl  2 5 carbo group, c to C alkenyl carbonate group, benzoyl group, naphthoyl group, C to  3 5 2 C alkoxycarbo group, c-c alkylthiocarbol group or c-c alkyl 5 2 5 2 5 Ruaminocarbol group; formyloxy group, C to C alkylcarboloxy group, C  2 5 3 ~ C alkenyl group, benzoyloxy group, naphthoyloxy group, C 5 2 ~ C alkoxycarboxoxy group, c ~ c alkylthiocarboxoxy group or 5 2 5 c to c alkylaminocarbo-loxy group; tri- (c to c alkyl) silyl group; or 2 5 1 2 Di- (C 1 -C alkoxy) phosphoryl group), 1 to: any one of L 1 1 2 Or a salt thereof. Q is a nitrogen atom or a group of the formula N—R ⁵ (wherein R ⁵ is a hydrogen atom; a hydroxyl group; a fluorine atom, a chlorine atom and a bromine atomic force, the same or different 1 to 3 substituents selected. A C to C alkyl group optionally substituted with a fluorine atom, chlorine atom or bromine atom  14 The group force may also be selected from the same or different 1 to 3 substituents which may be substituted with 1 to 3 substituents; a C to C alkoxy group; a C to C alkyloxy group; a C to C alkyloxy group; 1 4 2 4 2 4 Fluorine atom, chlorine atom, fluorine and group power of the group C force C-C alkyl group and C-C alkoxy optionally substituted by the same or different 1 to 3 substituents Fundamental group power Benzyl group which may be substituted with 1 to 3 identical or different substituents selected; same or different 1 to 3 selected from the group consisting of fluorine atom, chlorine atom, fluorine and chlorine C-C alkyl group optionally substituted with 3 substituents and C  1 2  ~ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents 1 2  Optionally substituted benzyloxy group; c to c alkylcarbonyl group, c to c  2 5 2 5 Lucoxycarbonyl group or c-c alkylaminocarbonyl group; or c-c alkyl  2 5 2 5 rucarbonyloxy group, c-c alkoxycarbonyloxy group or c-c alkyl  The compound or a salt thereof according to any one of claims 1 to: L 1, which is a 2 5 2 5 aminocarbo-loxy group). [14] Q force Nitrogen atom or formula N—R ⁵ group (wherein R ⁵ represents a hydrogen atom, a hydroxyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, an aryloxy group, a propargyloxy group, or a benzyl group. Or a benzyloxy group, a acetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an acetyloxy group, a methoxycarbonyloxy group, or an ethoxycarbonyloxy group). Or a salt thereof. [15] Q force Nitrogen atom or N—R ⁵ group (where R ⁵ is a hydrogen atom, a acetyl group, C to C group)  The compound or a salt thereof according to any one of claims 1 to 2, wherein the compound is a 2 3 alkoxyl group or a methyl group. [16] Q force Nitrogen atom or formula N—R ⁵ group (wherein R ⁵ represents a hydrogen atom, a hydroxyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a acetyl group, a methoxycarbon group, an ethoxy group) The compound or a salt thereof according to any one of claims 1 to L1, which is a carbo group, an acetyloxy group, a methoxy carbo-oxy group or an ethoxy carbo-oxy group.  [17] X is a halogen atom; a C-C alkyl group which may be substituted with the same or different 1 to 3 substituents which are selected for the group power of halogen atom; a fluorine atom and a chlorine atom  14  Force group power C 1 -C cycloalkyl group optionally substituted with 1 to 3 substituents selected; fluorine atom and chlorine nuclear power Group power selected same 3 6  Or a C to C alkenyl group which may be substituted with 1 to 3 different substituents;  twenty four Elementary atom and Chlorine nuclear power are the same or different C to C alkynyl groups optionally substituted by 1 to 3 selected substituents; fluorine atom, chlorine atom, bromine atom, Group power consisting of fluorine and chlorine may be substituted with the same or different 1 to 3 selected substituents C to C alkyl group, C to C alkoxy group, same or different  1 4 1 4  An amino group optionally substituted by 1 to 2 C-C alkyl or acetyl, nitro  1 2 Group power with group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group  1 2 A phenyl group or a naphthyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, fluorine and chlorine. C to C alkyl optionally substituted with 1 to 3 substituents  1 to 4 groups and C to C alkoxy group forces can also be selected 1 to 3 identical or different  14 Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Thiazolyl group, Isothiazolyl group, Imidazolyl group, Pyrazolyl group, Pyridyl group, Viradyl group or Pyridazyl group optionally substituted with substituents A C to C alkoxy group which may be substituted with 1 to 3 identical or different substituents;  14 The group force may also be substituted with 1 to 3 substituents of the same or different one selected, and the alkyl group may be substituted with 1 to 3 alkylthio groups; 14 C to C alkylsulfinyl optionally substituted with 1 to 3 different substituents  1 2 Group; fluorine atom and chlorine nuclear power group C-C alkylsulfol group optionally substituted by the same or different 1 to 3 selected substituents; the same or different  1 2 An amino group optionally substituted by 1 to 2 C-C alkyl groups or acetyl groups;  1 2 Rumyl group, c-c alkyl carbo group, benzoyl group, c-c alkoxy carbo group 2 5 2 5 Group or c-C alkylaminocarbol group; cyan group; or C-C alkyl group, C  2 5 1 4 2 ~ C-alkyl group, c-c alkyl group, phenol group, naphthyl group, furyl group, chelate 4 2 4 Nyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, pyridyl group, viridyl group or pyridazyl group group power may be selected and the hydrogen atom of the hydroxyl group may be substituted N-hydroxy (C to C al  The compound or a salt thereof according to any one of claims 1 to 16, wherein the compound is a 14-can) imidoyl group and has an n force of 0 to 3. X is a halogen atom; a fluorine atom, a chlorine atom, and a bromine atomic force. The same or different selected one to three substituents may be substituted. C to C alkyl group; C ~ C cycloalkyl group; fluorine atom, chlorine atom, bromine atom, C ~ C alkyl group and C 6 1 2 1 ~ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents 2 Optionally substituted phenyl group; furyl group, chenyl group or pyridyl group; _{c to c} al  1 2 alkoxy group; an amino group or acetyl group optionally substituted by 1 to 2 C-C alkyl groups  1 2  Luamino group; C to C alkylcarbonyl group, C to C alkoxycarbonyl group or C  2 3 2 3 2 ~ C alkylaminocarbonyl group; cyano group; or c ~ c alkyl group and phenyl group 3 1 2  The hydrogen atom of the hydroxyl group may be substituted with a substituent selected for both the group force and the force, and may be an N-hydroxy- (C to C) alkaneimidoyl group, and an n force of 0 to 2. Item 1-16  1 2  The compound or a salt thereof according to any one of the above. [19] X force is a halogen atom or a C to C alkyl group, and n force is 0 to 2,  14  6. The compound or salt thereof according to any one of 6 above. [20] X force The compound or a salt thereof according to any one of claims 1 to 16, which is a fluorine atom, a chlorine atom or a methyl group and has an n force of 0 to 2. [21] Y force Halogen atom; the same or different 1 C to C alkyl group optionally substituted with 3 substituents; fluorine atom and chlorine atom  14  Force group power C 1 -C cycloalkyl group optionally substituted with 1 to 3 substituents selected; fluorine atom and chlorine nuclear power Group power selected same 3 6  Or a C to C alkenyl group which may be substituted with 1 to 3 different substituents;  twenty four  Elementary atom and Chlorine nuclear power are the same or different C 1-3 alkynyl groups which may be substituted with the same or different substituents; fluorine atom, chlorine atom, bromine atom,  twenty four  Group power consisting of fluorine and chlorine, which may be substituted with the same or different 1 to 3 substituents selected C to C alkyl group, C to C alkoxy group, same or different  1 4 1 4  An amino group optionally substituted by 1 to 2 C-C alkyl or acetyl, nitro  1 2  Group power with group, cyano group, hydroxyl group, mercapto group and c-c alkylthio group  1 2  A phenyl group or a naphthyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, fluorine and chlorine. C to C alkyl optionally substituted with 1 to 3 substituents 1 to 4 groups and C to C alkoxy group forces can also be selected 1 to 3 identical or different Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Thiazolyl group, Isothiazolyl group, Imidazolyl group, Pyrazolyl group, Pyridyl group, Virazyl group or Pyridazyl group optionally substituted with substituents A C to C alkoxy group which may be substituted with 1 to 3 identical or different substituents;  14  The group force may also be substituted with 1 to 3 substituents of the same or different one selected, and the alkyl group may be substituted with 1 to 3 alkylthio groups; 14  C to C alkylsulfinyl optionally substituted with 1 to 3 different substituents  1 2  Group; fluorine atom and chlorine nuclear power group C-C alkylsulfol group optionally substituted by the same or different 1 to 3 selected substituents; the same or different  1 2  An amino group optionally substituted by 1 to 2 C-C alkyl groups or acetyl groups;  1 2  Rumyl group, c-c alkyl carbo group, benzoyl group, c-c alkoxy carbo group 2 5 2 5 group or C to C alkylaminocarbonyl group; cyan group; or hydroxyl group, m force 0  twenty five  21. The compound or a salt thereof according to any one of claims 1 to 20, which is ˜5. [22] Y is a halogen atom; a group force including a fluorine atom, a chlorine atom, and a bromine nuclear atom. A C to C alkyl group that may be substituted with the same or different 1 to 3 selected substituents; C  1 4 5 ~ C cycloalkyl group; fluorine atom, chlorine atom, bromine atom, C ~ C alkyl group and C 6 1 2 1 ~ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents 2 Optionally substituted phenyl group; furyl group, chenyl group or pyridyl group; _{c to c} al  1 2 alkoxy group; an amino group or acetyl group optionally substituted by 1 to 2 C-C alkyl groups  1 2  Luamino group; C to C alkylcarbonyl group, C to C alkoxycarbonyl group or C  2 3 2 3 2 ~ C alkylaminocarbonyl group; cyano group; or hydroxyl group, m force 0-2, Three  21. The compound or salt thereof according to any one of claims 1 to 20. [23] Y force is a halogen atom or a C to C alkyl group, and m force is 0 to 2.  14  The compound or salt thereof according to any one of 0. 24. The compound or salt thereof according to any one of claims 1 to 20, which is a fluorine atom, a chlorine atom or a methyl group and has an m force of 0 to 2. [25] 3— (5 1-yl 3-methyl 3, 4 dihydroisoquinoline 1-yl) quinoline; 3- (5-Fluoro-1,3,4 Dimethyl-1,4 Dihydroisoquinoline 1-yl) quinoline 3— (5—black mouth 3,4 dimethyl-3,4 dihydroisoquinoline 1—yl) quinoline; 1, 1-quinoline-3-yloo 3, H-spiro [cyclobutane 1, 4, mono-isoquinoline]; 3— (5-Fluoro-4,4 dimethyl-3,4 dihydroisoquinoline 1-yl) quinoline 5, 1 Fluoro 1, 1 Quinoline 1 3-yl 1, 3 H-spiro [Cyclobutane 1, 4, 1, Isoquinoline];  5, 1 Fluoro 1, 1 Quinoline 1 3-yl 1, 3 H-spiro [Cyclopentane 1, 4, 1, Soquinoline];  3— (5-Fluoro-1,3,4,4—Tetramethyl-1,3,4 Dihydroisoquinoline 1—yl) -1,7 Naphthyridine;  7— (5 Fluoro 3, 3, 4, 4—Tetramethyl 1, 3, 4 Dihydroisoquinoline 1—Inole) 3, 4 Dihydro 1H pyrido [3, 2-b] [l, 4] oxazine;  7— (5-Fluoro-1,3,4,4—Tetramethyl-1,3,4 Dihydroisoquinoline 1—Inole) 4-Methinole 3,4 Dihydro-2-H pyrido [3, 2-b] [l, 4] Oxazine;  3- (4,4 difluoro-2-hydroxy-1,3,3 dimethyl-1,2,3,4-tetrahydr oral isoquinoline 1 yl) quinoline;  3— (5-fluoro-2-hydroxy-1,3,4,4-tetramethyl-1,2,3,4-tetrahydroisoquinoline 1 yl) quinoline; and  3 -— (4,4-difunole low 2, 3, 3 trimethinole 1, 2, 3, 4-tetrahydroisoquinoline 1 yl) quinoline  Power of group force Selected compound or salt thereof.  An agrochemical composition comprising the compound according to any one of claims 1 to 25 or a salt thereof as an active ingredient.