JP2003171370A - Heterocyclic imino aromatic compound and fungicide for agricultural and horticultural use - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new fungicide for agricultural and horticultural use. <P>SOLUTION: This invention provides a heterocyclic imino aromatic compound expressed by formula (1) [A<SP>1</SP>is a (substituted) heterocyclic group; A<SP>2</SP>is a group selected from the group of formula (2), and the like; G is CH<SB>2</SB>CO<SB>2</SB>Me, or the like; X<SP>1</SP>and X<SP>2</SP>are each independently a halogen, an alkyl, or the like; X<SP>4</SP>groups are same or different substituents selected from halogen, alkyls, and the like; and (n) is the number of the substituents and is 0-6], a salt of the compound permissible as agrochemicals, and the fungicide for agricultural or horticultural use containing one or more compounds selected from the above compounds as an active component. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel heterocyclic imino aromatic compound or a salt thereof, and a fungicide containing one or more selected from the heterocyclic imino aromatic compound or a salt thereof as an active ingredient.

[0002]

2. Description of the Related Art Certain imino compounds are known in International Patent Application Publication (WO-95 / 27693) and European Patent Application (EP-254426) and are used as agricultural and horticultural fungicides. The use of is disclosed.

However, the heterocyclic imino aromatic compound of the present invention is a novel compound which has not been described in the literature.

[0004]

The existing fungicides for agricultural and horticultural use should not be satisfactory in terms of their efficacy and residual effect due to the increase of resistant bacteria and the narrow spectrum of existing agents. Therefore, there is a demand for the development of a fungicide having a low dose, high efficacy, and higher safety for target crops.

[0005]

In view of such circumstances, the present inventors have conducted various studies to find an excellent fungicide for agricultural and horticultural use, and as a result, the novel heterocyclic imino aromatic compound or its salt is sterilized. The present invention has been completed by finding that it has remarkable activity as an agent and is safe for target crops.

That is, the present invention provides the following [1] to

It relates to [9].

[1] Formula (1)

[0008]

[Chemical 9]

[Wherein A ¹ is

[0010]

[Chemical 10]

Va, Vb, Vc and Vd each independently represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and Ve represents a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a single bond, However, Va, Vb, Vc,
At least one of Vd and Ve is a nitrogen atom,
An oxygen atom or a sulfur atom, Va-Vb, Vb-V
The bond of c, Vc-Vd and Vd-Ve may be a single bond or a double bond, and a hydrogen atom or Y may be bonded to each atom, and A ² is from A ² a to A ² w

[0012]

[Chemical 11]

[0013]

[Chemical 12]

Represents a group selected from, G is G ¹ to G
¹⁴

[0015]

[Chemical 13]

Represents a group selected from: Z is --OR¹,
-SR¹Or -NR²R³And B is -CH₂-,-
C (= CH-OR^Four)-Or -C (= N-OR^Four)-
Yes, Y is Y'-D- (CH₂)_p− (However,
When Y is 2 or more, they may be the same or different. ),
A¹The two carbons on the same carbon atom of
Oxygen atom, nitrogen atom or sulfur atom together with elementary atom
3 to 7-membered ring which may contain 1 to 3 each or C = Q¹
Or Va and Vb, Vb and Vc, Vc
And Vd or two substituents Y on Vd and Ve are the same.
In the beginning, Va and Vb, Vb and Vc, Vc and Vd,
Is a carbon atom, a nitrogen atom, an oxygen atom together with Vd and Ve.
And one or more same or different selected from sulfur atom
Benzene containing the above atoms, optionally substituted with Y,
Forming a 5- or 6-membered ring in which one ring may be condensed
And D is a single bond, -NR^Five-, -C (= Q²)-,-
NR^Five-C (= Q²)-, -C (= Q²) -C (= Q³)
-, -CR⁶= N-, -N = CR⁶-, -CR⁶= N-N
= CR⁶-, -N = CR⁶-ON = CR⁶-, -CR⁶=
N-O-, -CR⁶= N-O-CR⁶= N-O-, -O-
N = CR⁶-CR⁶= N-O-, -CR⁶= N-NR^Five-
Or -ON = CR⁶-CR⁶= N-NR^Five−,
Q¹, Q²And Q³Are independently = O, = S, = N
-R⁷Or = C (R⁸) (R⁹) And Q^FourAnd Q^Five
Are independently = O or = S, X¹And X
³Are each independently halogen, C₁~ C₆Alkyl, C₁~ C
₆Haloalkyl, C₁~ C₆Alkoxy, C₁~ C₆Haloa
Lucoxy, C₁~ C₆Alkylthio, C₁~ C₆Alkyla
Mino, (C₁~ C₆Alkyl)₂Amino, NO₂, CN, ho
Lumil, OH, SH, NU¹U², C₁~ C₆Alkoxyca
Lubonyl, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo
Alkylcarbonyl, R^aMay be replaced with
Nil, R^aPhenoxy optionally substituted with R^aSet in
Optionally substituted phenylcarbonyl or C₁~ C₆
Alkylcarbonyloxy, X²Is C₁~ C₆A
Rukiru, C₁~ C₆Haloalkyl or R^aReplaced by
It's phenyl, and X^FourIs halogen, C₁~ C
₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C₆Arcoki
Shi, C₁~ C₆Haloalkoxy, C₁~ C₆Alkylthio,
C₁~ C₆Alkylamino, (C₁~ C₆Alkyl)₂Ami
No, NO₂, CN, formyl, OH, SH, NU¹U²,
C₁~ C₆Alkoxycarbonyl, C₁~ C₆Alkylcal
Bonil, C₁~ C₆Haloalkylcarbonyl, R^aReplace with
Optionally phenyl, R^aMay be replaced with
I phenoxy, R^aPhenylca optionally substituted with
Lubonyl or C₁~ C₆Alkylcarbonyloxy
R (However, X to replace^FourAre the same if two or more
They may be different from each other. ), R¹, R²And R^FourAre each
Independently, hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Haloa
Rukiru, C₃~ C₆Cycloalkyl, C₁~ C₆Alkoxy
C₁~ C₆Alkyl, C₁~ C₆Alkylsulfenyl C₁
~ C₆Alkyl, R^aPhenyl C optionally substituted with
₁~ C₆Alkyl or R^aHete optionally substituted with
Lower C₁~ C₆Alkyl and R³Is the hydrogen source
Child, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~
C₆Cycloalkyl, C₁~ C₆Alkoxy C₁~ C₆Al
Kill, C₁~ C₆Alkylsulfenyl C₁~ C₆Archi
Le, R^aPhenyl optionally substituted with R,^aReplaced by
Optional phenyl C₁~ C₆Alkyl or R^aso
Optionally substituted heteroaryl C₁~ C₆Alkyl
And R^FiveAnd R⁶Are each independently halogen, C₁
~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₆Shiku
Lower alkyl, C₁~ C₆Alkoxy, C₁~ C₆Alkoxy
C ₁~ C₆Alkyl, C₁~ C₆Alkylsulfenyl C₁
~ C₆Alkyl, C₁~ C₆Haloalkoxy, C₁~ C₆A
Rukylsulphenyl, C₁~ C₆Alkylsulfinyl,
C₁~ C₆Alkylsulfonyl, C₁~ C₆Haloalkyls
Luphenyl, C₁~ C₆Haloalkylsulfinyl, C₁
~ C₆Haloalkylsulfonyl, C₂~ C₆Alkenyl,
C₂~ C₆Haloalkenyl, C₂~ C₆Alkenyloxy,
C₂~ C₆Haloalkenyloxy, C₂~ C₆Alkenyls
Luphenyl, C₂~ C₆Alkenylsulfinyl, C₂~
C₆Alkenylsulfonyl, C₂~ C₆Halo alkenyls
Luphenyl, C₂~ C₆Haloalkenylsulfinyl, C
₂~ C₆Haloalkenylsulfonyl, C ₂~ C₆Alkini
Le, C₂~ C₆Haloalkynyl, C₂~ C₆Alkynyl oki
Shi, C₂~ C₆Haloalkynyloxy, C₂~ C₆Alkini
Rusulfenyl, C₂~ C₆Alkynylsulfinyl, C
₂~ C₆Alkynylsulfonyl, C₂~ C₆Haloalkynyl
Sulfenyl, C₂~ C₆Haloalkynylsulfinyl,
C₂~ C₆Haloalkynylsulfonyl, NO₂, CN, ho
Lumil, OH, SH, SCN, C₁~ C₆Alkoxycar
Bonil, C₁~ C₆Haloalkoxycarbonyl, C₁~ C₆
Alkylcarbonyl, C₁~ C₆Haloalkylcarboni
Le, C₁~ C₆Alkylcarbonyloxy, R ^aReplaced by
Optionally phenyl, R^aMay be replaced with
Phenyl C₁~ C₆Alkyl, R^aMay be replaced with
Phenylsulfonyl, R^aMay be replaced with
Phenyl C₁~ C₆Alkylsulfonyl, R^aReplaced by
Optionally heteroaryl, R^aMay be replaced with
Heteroaryl C₁~ C₆Alkyl, R^aReplaced by
Optionally heteroarylsulfonyl, R^aReplaced by
Optionally phenylcarbonyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkylcarbonyl, R^aso
Optionally substituted heteroarylcarbonyl or
-NU¹U²Where R⁶May be a hydrogen atom
R⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Ha
Lower alkyl, C₃~ C₆Cycloalkyl, C₁~ C₆Arco
Kish, C₁~ C₆Alkoxy C₁~ C₆Alkyl, C₁~ C₆
Alkylsulfenyl C₁~ C₆Alkyl, C₁~ C₆Al
Killsulfonyl, C₁~ C₆Haloalkylsulfonyl, C
₁~ C₆Alkylcarbonyl, C₁~ C₆Haloalkylcal
Bonil, R^aPhenyl optionally substituted with R,^aSet in
Optionally substituted phenoxy, R^aHas been replaced with
Good phenyl C₁~ C₆Alkyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkoxy, R^aReplaced by
Optionally phenylsulfonyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkylsulfonyl, R^aso
Optionally substituted heteroaryl, R^aReplaced by
Optionally heteroaryloxy, R^aReplaced by
Optionally heteroaryl C₁~ C₆Alkyl, R^aSet in
Optionally substituted heteroarylsulfonyl, R^aso
Optionally substituted phenylcarbonyl, R^aReplace with
Optionally phenoxycarbonyl, R^aReplaced by
Optional phenyl C₁~ C₆Alkylcarbonyl,
R^aA heteroaryl carbon which may be substituted with
Le, R^aHeteroaryloxy optionally substituted with
Carbonyl or R^aHeteroa optionally substituted with
Reel C₁~ C₆Alkylcarbonyl, R⁸and
R⁹Are each independently a hydrogen atom, halogen, C₁~ C₆A
Rukiru, C₁~ C₆Alkoxy, C₁~ C₆Alkylsulf
C, C₂~ C₆Alkenyl, NO₂, CN, formyl
Or C₁~ C₆An alkoxycarbonyl, R^TenIs
Hydrogen atom, halogen, R¹⁴, -OR¹⁴, -SR¹⁴, -S
OR¹⁴, Or -SO₂R¹⁴And R¹¹Is the hydrogen source
Child, R¹⁴Or CN and R¹²Is a hydrogen atom or R
¹⁴And R¹³Is a hydrogen atom, halogen, C₁~ C₆Al
Kill, C₁~ C₆Haloalkyl, C ₃~ C₆Cycloalk
Le, C₁~ C₆Alkoxy C₁~ C₆Alkyl, C₂~ C₆A
Lucenyl or C₂~ C₆Alkynyl, R¹⁴Is C
₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₂~ C₆Al
Kenil, C ₂~ C₆Haloalkenyl, C₂~ C₆Alkini
Le, C₂~ C₆Haloalkynyl, C₃~ C₆Cycloalk
Le, C₁~ C₆Alkylcarbonyl or C₁~ C₆Arco
Xycarbonyl, Y'is halogen, R^bReplace with
May be C₁~ C₁₂Alkyl, R^bReplaced by
May be C₃~ C₆Cycloalkyl, R^bReplaced by
May be C₂~ C₁₂Alkenyl, R^bHas been replaced with
Good C₂~ C₁₂Alkynyl, R^bMay be replaced with
I C₁~ C₁₂Alkoxy, R^bC optionally substituted with
₁~ C₆Alkoxy C₁~ C₆Alkoxy, R^bReplaced by
May be C₂~ C₆Alkenyloxy, R^bReplaced by
May be C₂~ C₆Alkynyloxy, R^bReplace with
May be C₁~ C₆Alkylsulfenyl, R^b
C optionally substituted with₂~ C₆Alkenylsulfeni
Le, R^bC optionally substituted with₂~ C₆Alkynils
Ruphenyl, R^bC optionally substituted with₁~ C₆Al
Kirsulfinyl, R^bC optionally substituted with₂~ C
₆Alkenylsulfinyl, R^bMay be replaced with
C₂~ C₆Alkynylsulfinyl, R^bHas been replaced by
May be C₁~ C₆Alkylsulfonyl, R^bReplaced by
May be C₂~ C₆Alkenylsulfonyl, R^bSet in
C that may be replaced₂~ C₆Alkynylsulfonyl, R
^bC optionally substituted with₁~ C₆Alkoxy Carboni
Le, R^bC optionally substituted with₁~ C₆Alkylcal
Bonil, R^bC optionally substituted with₁~ C₆Alkyl
Carbonyloxy, R^cPheny optionally substituted with
Le, R^cPhenoxy optionally substituted with R^cReplace with
Optionally phenyl C₁~ C₆Alkyl, R^cSet in
Phenyl C which may be substituted₁~ C₆Alkoxy, R^c
Phenylsulfonyl optionally substituted with R^cSet in
Optionally substituted phenylsulfinyl, R^cReplace with
Optionally phenylsulfenyl, R^cReplaced by
Optional phenyl C₁~ C₆Alkylsulfeni
Le, R^cPhenyl C optionally substituted with₁~ C₆Al
Kirsulfinyl, R^cPheny optionally substituted with
Le C₁~ C₆Alkylsulfonyl, R^cHas been replaced with
Good heteroaryl, R^cMay be replaced with
Teloaryloxy, R^cHete optionally substituted with
Lower C₁~ C₆Alkyl, R^cEven if replaced with
Good heteroaryl C₁~ C₆Alkoxy, R^cReplaced by
Optionally heteroarylsulfinyl, R^cSet in
Optionally substituted heteroarylsulfenyl, R^c
A heteroarylsulfonyl optionally substituted with R
^cHeteroaryl C optionally substituted with₁~ C₆Al
Kirsulphenyl, R^cHetero optionally substituted with
Aryl C₁~ C₆Alkylsulfinyl, R^cReplaced by
Optionally substituted heteroaryl C₁~ C₆Alkyl sulfo
Nil, R^cPhenylcarboni optionally substituted with
Le, R^cPhenylcarbonyl which may be substituted with
Kish, R^cPhenoxycarboni optionally substituted with
Le, R^cPhenyl C optionally substituted with₁~ C₆Al
Kircarbonyl, R^cPhenyl optionally substituted with
C₁~ C₆Alkylcarbonyloxy, R^cReplaced by
Optionally heteroarylcarbonyl, R^cReplaced by
Optionally heteroarylcarbonyloxy, R^cso
Optionally substituted heteroaryloxycarboni
Le, R^cHeteroaryl C optionally substituted with₁~ C
₆Alkylcarbonyl, R^cHete optionally substituted with
Lower C₁~ C₆Alkylcarbonyloxy, N
O₂, CN, formyl or naphthyl, R^aIs ha
Rogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C
₃~ C₆Cycloalkyl, C₁~ C₆Alkoxy, C₁~ C₆
Alkoxy C₁~ C₆Alkyl, C₁~ C₆Alkylsulf
Phenyl C₁~ C₆Alkyl, C₁~ C₆Haloalkoxy, C
₁~ C₆Alkylsulfenyl, C₁~ C₆Alkylsulf
Inyl, C₁~ C₆Alkylsulfonyl, C₁~ C₆Haloa
Rukylsulphenyl, C₁~ C₆Haloalkylsulfini
Le, C₁~ C₆Haloalkylsulfonyl, C₂~ C₆Arche
Nil, C₂~ C₆Haloalkenyl, C₂~ C₆Alkenyl
Kish, C₂~ C₆Haloalkenyloxy, C₂~ C₆Arche
Nilsulphenyl, C₂~ C₆Alkenylsulfinyl,
C₂~ C₆Alkenylsulfonyl, C₂~ C₆Halo archeni
Rusulfenyl, C₂~ C₆Haloalkenylsulfini
Le, C₂~ C₆Haloalkenylsulfonyl, C₂~ C₆Al
Quinyl, C₂~ C₆Haloalkynyl, C₂~ C₆Alkynyl
Oxy, C₂~ C₆Haloalkynyloxy, C₂~ C₆Al
Quinylsulfenyl, C₂~ C₆Alkynyl sulfini
Le, C₂~ C₆Alkynylsulfonyl, C₂~ C₆Halo al
Quinylsulfenyl, C₂~ C₆Halo alkynyl sulfi
Nil, C₂~ C₆Haloalkynylsulfonyl, NO₂, C
N, formyl, SH, OH, SCN, C₁~ C₆Arcoki
Sicarbonyl, C₁~ C₆Alkylcarbonyl, C₁~ C₆
Haloalkylcarbonyl, C₁~ C₆Alkyl carbonyl
Oxy, phenyl or -NU¹U²And replace
R^aIs 1 to 5 (provided that R is^aIs 2 or more
May be the same or different from each other), R^bIs a halogen
N, C₃~ C₆Cycloalkyl, C₁~ C₆Alkoxy, C
₁~ C₆Alkoxy C₁~ C₆Alkoxy, C₁~ C₆Archi
Rusulphenyl C₁~ C₆Alkoxy, C₁~ C₆Halo al
Coxy, C₁~ C₆Alkylsulfenyl, C₁~ C₆Al
Kirsulfinyl, C₁~ C₆Alkylsulfonyl, C₁
~ C₆Haloalkylsulfenyl, C₁~ C₆Halo Archi
Rusulfinyl, C₁~ C₆Haloalkylsulfonyl, C
₂~ C₆Alkenyloxy, C₂~ C₆Halo alkenyl oki
Shi, C₂~ C₆Alkenylsulfenyl, C₂~ C₆Arche
Nilsulfinyl, C₂~ C₆Alkenylsulfonyl, C
₂~ C₆Haloalkenylsulfenyl, C₂~ C₆Halo al
Kenylsulfinyl, C₂~ C₆Haloalkenyl sulfoni
Le, C₂~ C₆Alkynyloxy, C₂~ C₆Halo alkini
Roxy, C₂~ C₆Alkynylsulfenyl, C₂~ C₆
Alkynylsulfinyl, C₂~ C₆Alkynyl sulfoni
Le, C₂~ C₆Haloalkynylsulfenyl, C₂~ C₆Ha
Loalkynylsulfinyl, C₂~ C₆Halo alkynyls
Lefonil, NO₂, CN, formyl, OH, SH, SC
N, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Alkyl
Carbonyl, C₁~ C₆Haloalkylcarbonyl, C₁~
C₆Alkylcarbonyloxy, R^aEven if replaced with
Good phenyl, R^aPhenoki optionally substituted with
Shi, R^aPhenyl C optionally substituted with ₁~ C₆Al
Koxy, R^aPhenylsulfoni which may be substituted with
Le, R^aPhenyl C optionally substituted with₁~ C₆Al
Killsulfonyl, R^aHeteroa optionally substituted with
Reel, R^aA heteroaryl which may be substituted with
Kish, R^aHeteroarylsulu that may be substituted with
Honil, R^aPhenylcarboni optionally substituted with
Le, R^aPhenoxycarboni optionally substituted with
Le, R^aPhenyl C optionally substituted with₁~ C₆Al
Kircarbonyl, R^aHeteroa optionally substituted with
Reel carbonyl, R^aHetero optionally substituted with
Aryloxycarbonyl or R^aHas been replaced with
Good heteroaryl C₁~ C₆Alkyl carbonyl
Is -NU¹U²Or an oxygen atom or a nitrogen atom
Or 1 to 4 heteroatoms selected from sulfur atoms
An optionally substituted 3- to 7-membered ring, which is substituted R^b
Is 1 to 8 (provided that R is^bIf there are two or more
May be the same or different from each other), R^cIs a halogen
R^bC optionally substituted with₁~ C₁₂Alkyl, R
^bC optionally substituted with₃~ C₆Cycloalkyl, R^b
C optionally substituted with₂~ C ₁₂Alkenyl, R^bSet in
C that may be replaced₂~ C₁₂Alkynyl, R^bReplaced by
May be C₁~ C₁₂Alkoxy, R^bReplaced by
May be C₁~ C₆Alkoxy C₁~ C₆Alkoxy, R
^bC optionally substituted with₂~ C₆Alkenyloxy,
R^bC optionally substituted with₂~ C₆Alkynyl oki
Shi, R^bC optionally substituted with₁~ C₆Alkylsul
Phenyl, R^bC optionally substituted with₂~ C ₆Arche
Nilsulphenyl, R^bC optionally substituted with₂~ C
₆Alkynylsulfenyl, R^bMay be replaced with
C₁~ C₆Alkylsulfinyl, R^bHas been replaced with
Good C₂~ C₆Alkenylsulfinyl, R^bReplaced by
May be C₂~ C₆Alkynylsulfinyl, R^b
C optionally substituted with₁~ C₆Alkylsulfonyl,
R^bC optionally substituted with₂~ C₆Alkenyl sulfo
Nil, R^bC optionally substituted with₂~ C₆Alkynyl
Sulfonyl, R^bC optionally substituted with₁~ C₆Al
Coxycarbonyl, R^bC optionally substituted with₁~ C
₆Alkylcarbonyl, R^bC optionally substituted with₁
~ C₆Alkylcarbonyloxy, NO₂, CN, Holmi
Le, OH, SH, SCN, C₁~ C₆Alkoxy Carboni
Le, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo Archi
Lecarbonyl, C ₁~ C₆Alkylcarbonyloxy, R
^aPhenyl optionally substituted with R,^aHas been replaced by
Phenoxy, R^aMay be replaced with
Nil C₁~ C ₆Alkyl, R^aMay be replaced with
Phenyl C₁~ C₆Alkoxy, R^aMay be replaced with
Phenylsulfonyl, R^aMay be replaced with
Phenylsulfinyl, R^aMay be replaced with
Nilsulphenyl, R^aPheny optionally substituted with
Le C₁~ C₆Alkylsulfenyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkylsulfinyl, R^a
Phenyl C optionally substituted with₁~ C₆Alkylsul
Honil, R^aA heteroaryl which may be substituted with
R^aHeteroaryloxy optionally substituted with R,^a
Heteroaryl C optionally substituted with₁~ C₆Archi
Le, R^aHeteroaryl C optionally substituted with₁~ C
₆Alkoxy, R^aHeteroaryl optionally substituted with
Rusulfinyl, R^aHeteroa optionally substituted with
Reel Sulfenyl, R^aHete optionally substituted with
Lower arylsulfonyl, R^aMay be replaced with
Terror aryl C₁~ C₆Alkylsulfenyl, R^aSet in
Optionally substituted heteroaryl C₁~ C₆Alkyls
Rufinil, R^aHeteroaryl optionally substituted with
Le C₁~ C₆Alkylsulfonyl, R^aHas been replaced with
Good phenyl carbonyl, R^aMay be replaced with
Phenyl carbonyloxy, R^aEven if replaced with
Good phenoxycarbonyl, R^aMay be replaced with
I Phenyl C₁~ C₆Alkylcarbonyl, R^aReplaced by
Optional phenyl C₁~ C₆Alkylcarbonyl
Kish, R^aHeteroarylcarc which may be substituted with
Bonil, R^aA heteroaryl group optionally substituted with
Lubonyloxy, R^aHeteroa optionally substituted with
Reel oxycarbonyl, R^aMay be replaced with
Heteroaryl C₁~ C₆Alkylcarbonyl, R^aSet in
Optionally substituted heteroaryl C₁~ C₆Alkyr
Lubonyloxy or -NU¹U²And R to replace^c
Is 1 to 5 (provided that R is^cIf there are two or more
May be the same or different from each other), U¹And U²Is
Each independently, hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Ha
Lower alkyl, C₃~ C₆Cycloalkyl, C₁~ C₆Arco
Kishi C₁~ C₆Alkyl, C₁~ C₆Alkylsulfenyl
C₁~ C₆Alkyl, formyl, C₁~ C₆Alkyl sulfo
Nil, C₁~ C₆Haloalkylsulfonyl, C₁~ C₆Al
Coxycarbonyl, C₁~ C₆Alkylcarbonyl or
C₁~ C₆Haloalkylcarbonyl, or U
¹And U²Together with oxygen, nitrogen or sulfur
Contains 1 to 4 heteroatoms selected from yellow atoms
Is a 3- to 7-membered ring, and n represents the number of substituents.
, 0 to 4, p is the number of repetitions, is 0 or
Et al 2. ] A heterocyclic imino aromatic compound represented by
Or the salt acceptable as the pesticide.

[2] A ¹ is

[0018]

[Chemical 14]

[0019]

[Chemical 15]

Where d represents the number of substituents, 0 to 2, and e represents the number of substituents, 0 to 3,
f represents the number of substituents and is 0 to 4, g is the number of substituents and is 0 to 5, h is the number of substituents and is 0 to 6, and i is , Represents the number of substituents, 0 to 1, j represents the number of substituents, 0 to 7,
k represents the number of substituents is from 0 8, Ya and Y are each independently a _{Y'-D- (CH 2) p} - or is (provided that the total of Ya and Y are two more time, and what Ya, Y What or Ya and may be the same or different from each other and Y.), the two Y or Ya substituted on the same carbon atom of a ^1, an oxygen atom together with the carbon atom ,
The heterocyclic imino aroma according to [1], which forms a 3- to 7-membered ring which may respectively contain 1 to 3 nitrogen atoms or sulfur atoms or forms C = Q ¹ , and Ya may represent a hydrogen atom. Group compounds or their pesticidally acceptable salts.

[3] The heterocyclic imino aromatic compound or the pesticidally acceptable salt thereof according to [1] or [2], wherein A ¹ represents a 5-membered heterocycle.

[4] A ¹ is

[0023]

[Chemical 16]

(Wherein Y, Ya, d and f have the same meanings as in [2]) and are acceptable as the heterocyclic imino aromatic compound or the pesticide thereof according to [1] and [2]. Ru salt.

[5] Ya and Y are independently Y '.
-D- (CH _{2) p} - in either, (provided that when the sum of the Ya and Y are two or more, and do Ya, may be the same or different from each other and Y do or Ya and Y.) With 2 Y or Ya substituted on the same carbon atom of A ¹ , a 3- to 7-membered ring optionally having 1 to 3 oxygen atoms, nitrogen atoms or sulfur atoms together with the carbon atom, or C = Q
The heterocyclic imino aromatic compound according to [2], [3] or [4] which forms ¹ , or a pesticidally acceptable salt thereof.

[6] G represents G ¹ [1], [2],
The heterocyclic imino aromatic compound of [3], [4] or [5] or a pesticidally acceptable salt thereof.

[7] The salt acceptable as a pesticide is a hydrochloride, hydrobromide, hydroiodide, formate, acetate or oxalate [1], [2], [3]. ,
The salt according to [4], [5] or [6].

[8] [1], [2], [3],
A pesticide containing one or more selected from the heterocyclic imino aromatic compounds or salts thereof described in [4], [5], [6] or [7] as an active ingredient.

[0029]

[9] [1], [2], [3],
A bactericide containing, as an active ingredient, one or more selected from the heterocyclic imino aromatic compounds described in [4], [5], [6] or [7] or salts thereof.

However, when the present compound has stereoisomers, geometric isomers, tautomers, diastereomers, all the respective isomers and mixtures thereof are included.

[0031]

BEST MODE FOR CARRYING OUT THE INVENTION Each substituent of the compound of the present invention represented by the formula (1) is exemplified below.

The abbreviations have the following meanings.

Me is a methyl group, Et is an ethyl group, Pr is a propyl group, Bu is a butyl group, Pen is a pentyl group, Hex.
Is hexyl group, Hep is heptyl group, Oct is octyl group, Non is nonyl group, Dec is decyl group, Undec is undecanyl group, Dodec is dodecyl group, n is normal,
i is iso, s is secondary, t is tertiary,
c represents cyclo, Ph represents a phenyl group, and in the notation of the phenyl group, for example, 2-Cl-Ph represents a 2-chlorophenyl group, 2-MeO-3-Me-Ph represents 2-methoxy-3-.
Represents a methylphenyl group.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ ,
^{R 8, R 9, R 13} , R 14, R a, X 1, X 2, X 3, X 4, U 1
And C ₁ -C ₆ alkyl in the definition of U ² is
Methyl, ethyl, n- as linear or branched alkyl
Propyl, i-propyl, n-butyl, i-butyl, t-butyl, s-butyl, n-pentyl, n-hexyl, 2-ethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl,
1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-
Dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl and 4-methyl Examples include pentyl.

R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹³ , R ^a ,
The halogen atom in the definition of R ^b , R ^c , X ¹ , X ³ , X ⁴ and Y ′ includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R
C ₁ -C ₆ haloalkyl in the definition of ¹³ , R ¹⁴ , ^Ra , X ¹ , X ² , X ³ , X ³ , X ⁴ , U ¹ and U ² is fluoromethyl or chloromethyl as a linear or branched haloalkyl. , Bromomethyl, iodomethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 1-bromoethyl, 1-iodoethyl, 1-fluoroethyl, 2-chloroethyl, 2-bromoethyl , 2-iodoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2,2,2-trifluoro-1 -Chloroethyl, 3-fluoropropyl, 3-chloropropyl, 1-fluoro-i-propyl, 1-chloro-i-propyl, heptafluoropropyl, 1,1,2,2, Examples thereof include 3,3-hexafluoro-n-propyl, 4-chlorobutyl, 4-fluorobutyl, 5-chloropentyl, 5-fluoropentyl, 6-chlorohexyl and 6-fluorohexyl.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R
C ₃ in the definition of ¹³ , R ¹⁴ , R ^a , R ^b , U ¹ and U ^2.
The -C ₆ cycloalkyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl and the like.

R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ^a , R ^b ,
C ₁ -C ₆ alkoxy in the definition of X ¹ , X ³ and X ⁴ is, as linear or branched alkoxy, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s- Butoxy, t-butoxy, n-pentyloxy, n-hexyloxy, 1,1-dimethylpropoxy,
1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-
Ethylpropoxy, 1,1,2-trimethylpropoxy, 1,2,
2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2-methylpropoxy 1-methylbutoxy, 2
-Methylbutoxy, 3-methylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1.3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethyl Examples thereof include butoxy, 3,3-dimethylbutoxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy and 4-methylpentyloxy.

R ⁵ , R ⁶ , R ^a , R ^b , X ¹ , X ³ and X ⁴
C ₁ -C ₆ haloalkoxy in the definition of is C ₁
To C ₆ straight-chain or branched haloalkoxy, fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, dichloromethoxy, trichloromethoxy, difluoromethoxy, trifluoromethoxy,
Chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, 1-chloroethoxy, 1-
Bromoethoxy, 1-iodoethoxy, 1-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2,2,2-trifluoro
-1-chloroethoxy, 1,1,2,2-tetrafluoroethoxy, 3-bromopropoxy, 1-fluoro-i-propoxy, 1
-Chloro-i-propoxy, 3-fluoropropoxy, 3-chloropropoxy, heptafluoropropoxy, 1,1,2,2,3,
Examples thereof include 3-hexafluoropropoxy, 4-chlorobutoxy, 4-fluorobutoxy, 5-chloropentyloxy, 5-fluoropentyloxy, 6-chlorohexyloxy and 6-fluorohexyloxy.

R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ^a , R ^b , X ¹ , X ³
And C ₁ -C ₆ alkylsulfenyl in the definition of X ⁴ is methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio as a straight-chain or branched alkylsulfenyl. , T-butylthio, n-pentylthio, n-hexylthio and the like.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₁ -C ₆ alkylsulfinyl, methylsulfinyl as linear or branched alkylsulfinyl,
Examples thereof include ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, n-pentylsulfinyl and n-hexylsulfinyl.

R ⁵ , R ⁶ , R ⁷ , R ^a , R ^b , U ¹ and U ²
C ₁ -C ₆ alkylsulfonyl in the definition of
As a linear or branched alkylsulfonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl,
Examples thereof include i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl and n-hexylsulfonyl.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R
C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl in the definition of ¹³ , R ^a , U ¹ and U ² is methoxymethyl, ethoxymethyl, n-propoxymethyl, i-propoxymethyl, n-butoxymethyl, i -Butoxymethyl, s-butoxymethyl, t-butoxymethyl, n-pentyloxymethyl,
2-methoxyethyl, 3-ethoxypropyl, 3-methoxypropyl and the like can be mentioned.

C ₁ -C ₆ alkoxy C ₁ in the definition of R ^b
~ C ₆ alkoxy includes methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, i-propoxymethoxy, n-butoxymethoxy, i-butoxymethoxy, s-butoxymethoxy, t-butoxymethoxy, n-pentyloxymethoxy, 2 -Methoxyethoxy, 3-ethoxypropoxy, 3-methoxypropoxy and the like can be mentioned.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ ,
R ^a, as the C ₁ -C ₆ alkylsulfenyl C ₁ -C ₆ alkyl in the definition of U ¹ and U ^2, straight-chain or a branched alkyl sulphenyl alkyl, methylthiomethyl, ethylthiomethyl, n- Propylthiomethyl,
i-propylthiomethyl, n-butylthiomethyl, i-butylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, n-pentylthiomethyl, 2-methylthioethyl, 3-ethylthiopropyl and 3-methylthio Examples include propyl.

As C ₁ -C ₆ alkylsulfenyl C ₁ -C ₆ alkoxy in the definition of R ^b , methylthiomethoxy, ethylthiomethoxy, n-propylthiomethoxy,
i-propylthiomethoxy, n-butylthiomethoxy, i-butylthiomethoxy, s-butylthiomethoxy, t-butylthiomethoxy, n-pentylthiomethoxy, 2-methylthioethoxy, 3-ethylthiopropoxy and 3-methylthio Examples include propoxy.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₁ -C ₆ haloalkylsulfenyl, trifluoromethylthio as linear or branched haloalkylthio, chlorodifluoromethyl-thio, bromo difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1 , 1,2,2-Tetrafluoroethylthio, 2-fluoroethylthio, pentafluoroethylthio, 1-fluoro-i-propylthio and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₁ -C ₆ haloalkylsulfinyl, linear or fluoro methylsulfinyl as branched haloalkylsulfinyl, chlorodifluoromethyl methylsulfinyl, bromodifluoromethyl methylsulfinyl, trifluoromethylsulfinyl, trichloromethyl methylsulfinyl, 2,2,2 Ethylsulfinyl, 1,1,2,2-
Tetrafluoroethylsulfinyl, 2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 1-fluoro-i-propylsulfinyl and the like can be mentioned.

R ⁵ , R ⁶ , R ⁷ , R ^a , R ^b , U ¹ and U ²
C ₁ -C ₆ haloalkylsulfonyl in the definition of is a linear or branched haloalkylsulfonyl such as fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2, Examples thereof include 2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-fluoroethylsulfonyl, pentafluoroethylsulfonyl and 1-fluoro-i-propylsulfonyl.

R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹³ , R ¹⁴ and R
^As C ₂ -C ₆ alkenyl in the definition of ^a , straight-chain or branched alkenyl is ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl. , 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl -2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-
Methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3
-Butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1-methyl-2-pentenyl, 2-methyl-2
-Pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl , 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,
3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1,
2-trimethyl-2-propenyl and 1-ethyl-1-methyl-2
-Propenyl and the like can be mentioned.

[0051] R ^5, R ^6, R ¹⁴ and Examples C ₂ -C ₆ haloalkenyl in the definition of R ^a, 2-chloroethenyl as straight or branched haloalkenyl, 2-bromoethenyl, 2,2-dichloroethenyl pantothenyl , 3-chloro-2-propenyl, 3-fluoro-2-propenyl, 3-bromo-2-propenyl, 3-iodo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-difluoro-2 -Propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3-butenyl and 4,4-difluoro-3-
Butenyl and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ alkenyloxy, a straight-chain or branched alkenyloxy 1-methyl ethenyl oxy, 2-propenyloxy, 1-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy and 2-methyl -2-propenyloxy and the like.

C ₅ -C ₆ haloalkenyloxy in the definition of R ⁵ , R ⁶ , R ^a , R ^b and X is 2-chloroethenyloxy, 2-chloroethenyloxy as a straight-chain or branched haloalkenyloxy, 2- Bromoethenyloxy, 2,2-dichloroethenyloxy, 3-chloro-2-propenyloxy, 3-fluoro-2-propenyloxy, 3-bromo-2-propenyloxy, 3-iodo-2-propenyloxy, 3 , 3-dichloro-2-
Examples thereof include propenyloxy, 3,3-difluoro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy and 4,4-difluoro-3-butenyloxy.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ alkenyl Le phenyl, straight or branched 1-methyl-et tennis Lucio as alkenyl Le phenyl, 2-propenylthio, 1-methyl-2-propenylthio, 2-butenylthio, 3-butenylthio and 2- Methyl-2
-Propenylthio and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ alkenylsulfinyl, 1-methyl ethenyl Nils sulfinyl a linear or branched alkenylsulfinyl, 2-propenyl Nils sulfinyl, 1-methyl-2
-Propenylsulfinyl, 2-butenylsulfinyl, 3
Examples include-butenylsulfinyl and 2-methyl-2-propenylsulfinyl.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ alkenylsulfonyl, 1-methyl ethenyl sulfonyl as straight-chain or branched alkenyl sulfonyl, 2-propenyl-sulfonyl, 1-methyl-2-propenyl-sulfonyl, 2-butenyl sulfonyl, 3-butenyl sulfonyl And 2-methyl-2-propenylsulfonyl and the like.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ halo alkenyl Le phenyl, linear or 2-chloro et tennis Lucio as branched halo alkenyl Le phenyl, 2-bromo et tennis thio, 2,2-dichloroethene tennis thio, 3-chloro-2-propenylthio , 3-fluoro-
2-propenylthio, 3-bromo-2-propenylthio, 3-iodo-2-propenylthio, 3,3-dichloro-2-propenylthio, 3,3-difluoro-2-propenylthio, 4-chloro-2 -Butenylthio, 4,4-dichloro-3-butenylthio and 4,4-
Difluoro-3-butenylthio and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
_2- C ₆ haloalkenylsulfinyl includes 2-chloroethenylsulfinyl, 2-bromoethenylsulfinyl, 2,2-dichloroethenylsulfinyl and 3-chloro-2-, which may be linear or branched haloalkenylsulfinyl.
Propenylsulfinyl, 3-Fluoro-2-propenylsulfinyl, 3-Bromo-2-propenylsulfinyl, 3-
Iodo-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 3,3-difluoro-2-propenylsulfinyl, 4-chloro-2-butenylsulfinyl, 4,4
-Dichloro-3-butenylsulfinyl and 4,4-difluoro-3-butenylsulfinyl and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ haloalkenyl sulfonyl, straight or chloro ethenyl sulfonyl as branched haloalkenyl sulfonyl, 2-bromo-ethenyl sulfonyl, 2,2-dichloroethene pantothenyl sulfonyl, 3-chloro-2-propenyl-sulfonyl , 3-fluoro-2-propenylsulfonyl, 3-bromo-2-propenylsulfonyl, 3-iodo-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl,
3,3-difluoro-2-propenylsulfonyl, 4-chloro-2-
Examples include butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl and the like.

[0060] R ^5, as the C ₂ -C ₆ alkynyl in the definition of R ^6, R ^13, R ¹⁴ and R ^a, linear or branched ethynyl as alkynyl, 1-propynyl, 2-propynyl, 1-methyl -2-propynyl, 1,1-dimethyl-2-propynyl, 1-methyl-1-ethyl-2-propynyl, 1-butynyl,
2-butynyl, 3-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl
-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl
-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-
Butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, Examples include 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl and hexynyl.

[0061] R ^5, as the C ₂ -C ₆ haloalkynyl the definition of R ^6, R ¹⁴ and R ^a, linear or branched chloroethynyl as haloalkynyl, bromo ethynyl, iodo ethynyl, 3-chloro-2 -Propinyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, 4-bromo-3
-Butynyl, 4-iodo-3-butynyl, 6-iodo-5-hexynyl and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
_2- C ₆ alkynyloxy includes ethynyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 1,1-dimethyl-as linear or branched alkynyloxy.
2-propynyloxy, 1-methyl-1-ethyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 1,1-dimethyl-2-butynyloxy, 1-pentynyloxy, Examples include 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy and hexynyloxy.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ haloalkynyloxy, straight-chain or branched-chloro ethynyloxy as haloalkynyloxy, bromo ethynyloxy, iodo ethynyloxy, 3-
Chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 3-iodo-2-propynyloxy, 4-bromo-3-butynyloxy, 4-iodo-3-butynyloxy, 6-iodo-5-hexynyloxy, etc. can give.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
₂ -C ₆ The alkyl Nils Le phenyl, straight-chain or branched alkyl Nils Le ethynylthio as phenyl, 2-
Propynylthio, 1-methyl-2-propynylthio, 1,1-dimethyl-2-propynylthio, 1-methyl-1-ethyl-2-propynylthio, 2-butynylthio, 3-butynylthio, 1-methyl-2- Butynylthio, 1,1-dimethyl-2-butynylthio, 1-
Examples include pentynylthio, 2-pentynylthio, 3-pentynylthio, 4-pentynylthio and hexynylthio.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ alkynylsulfinyl, straight or ethynyl sulfinyl a branched alkynylsulfinyl, 2-propynyl sulfinyl, 1-methyl-2-propynyl sulfinyl, 1,1-dimethyl-2-propynyl sulfinyl, 1-methyl - 1-ethyl-2-propynylsulfinyl, 2-butynylsulfinyl, 3-butynylsulfinyl, 1-methyl-2-butynylsulfinyl, 1,1-dimethyl-
2-butynylsulfinyl, 1-pentynylsulfinyl,
Examples include 2-pentynylsulfinyl, 3-pentynylsulfinyl, 4-pentynylsulfinyl and hexynylsulfinyl.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ alkynylsulfonyl, ethynyl sulfonyl as linear or branched alkynylsulfonyl,
2-propynylsulfonyl, 1-methyl-2-propynylsulfonyl, 1,1-dimethyl-2-propynylsulfonyl, 1-methyl-1-ethyl-2-propynylsulfonyl, 2-butynylsulfonyl, 3-butynylsulfonyl, 1-methyl-2-butynylsulfonyl, 1,1-dimethyl-2-butynylsulfonyl, 1
-Pentynylsulfonyl, 2-Pentynylsulfonyl, 3-
Examples include pentynylsulfonyl, 4-pentynylsulfonyl and hexynylsulfonyl.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ haloalkylene Nils Le phenyl, straight or branched halo alkyl Nils Le chloroethynyl thio as phenyl, bromo ethynyl thio, iodo ethynyl thio, 3-chloro-2-propynylthio, 3-bromo-2-propynyl Thio, 3-iodo-2-propynylthio, 4-bromo-3-butynylthio, 4-iodo-3-butynylthio and 6-iodo-5-
Hexynylthio and the like can be mentioned.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ halo alkynylsulfinyl, straight or chloroethynyl sulfinyl a branched halo alkynylsulfinyl, bromo ethynyl sulfinyl, iodo ethynyl sulfinyl, 3-chloro-2-propynyl sulfinyl, 3-bromo-2-propynyl sulfinyl, 3-
Examples thereof include iodo-2-propynylsulfinyl, 4-bromo-3-butynylsulfinyl, 4-iodo-3-butynylsulfinyl and 6-iodo-5-hexynylsulfinyl.

C in the definition of R ⁵ , R ⁶ , R ^a and R ^b
The ₂ -C ₆ haloalkynyl sulfonyl, chloroethynyl sulfonyl as straight-chain or branched halo alkynylsulfonyl, bromo ethynyl sulfonyl, iodo ethynyl sulfonyl, 3-chloro-2-propynyl-sulfonyl, 3
-Bromo-2-propynylsulfonyl, 3-iodo-2-propynylsulfonyl, 4-bromo-3-butynylsulfonyl, 4-
Examples thereof include iodo-3-butynylsulfonyl and 6-iodo-5-hexynylsulfonyl.

R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁴ , R ^a , R ^b , X
C ₁ -C ₆ alkoxycarbonyl in the definition of ¹ , X ³ , X ⁴ , U ¹ and U ² is, as linear or branched alkoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl. , N-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, n-
Examples include pentyloxycarbonyl and n-hexyloxycarbonyl.

R ⁵ , R ⁶ , R ⁷ , R ¹⁴ , R ^a , R ^b , X ¹ , X
C ₁ -C ₆ alkylcarbonyl in the definition of ³ , X ⁴ , U ¹ and U ² is, as a linear or branched alkylcarbonyl, acetyl, propionyl, n-propylcarbonyl, i-propylcarbonyl, n-butylcarbonyl. ,
Examples thereof include i-butylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, n-pentylcarbonyl and n-hexylcarbonyl.

R ⁵ , R ⁶ , R ⁷ , R ^a , R ^b , X ¹ , X ³ ,
C ₁ -C ₆ haloalkylcarbonyl in the definition of X ⁴ , U ¹ and U ² is, as a linear or branched haloalkylcarbonyl, chloroacetyl, fluoroacetyl, chlorofluoroacetyl, chlorodifluoroacetyl, dichloroacetyl, difluoroacetyl. , Trifluoroacetyl, 3,3,3-trifluoropropionyl, pentafluoropropionyl and the like.

R ⁵ , R ⁶ , R ^a , R ^b , X ¹ , X ³ , X ⁴ , U ¹
And C ₁ -C ₆ alkylcarbonyloxy in the definition of U ² include acetyloxy, propionyloxy as linear or branched alkylcarbonyloxy,
Examples include n-propylcarbonyloxy, i-propylcarbonyloxy, n-butylcarbonyloxy, i-butylcarbonyloxy, s-butylcarbonyloxy, t-butylcarbonyloxy, n-pentylcarbonyloxy and n-hexylcarbonyloxy. To be

The phenyl C ₁ -C ₆ alkyl optionally substituted by R ^a in the definition of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^c is a straight group. Benzyl, 2-chlorobenzyl, 3- as a chain or branched phenylalkyl
Bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-t-butylbenzyl, 2-methylbenzyl, 2-methoxybenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1 -Methyl-1-phenylethyl, 1- (4-chlorophenyl) -1-methylethyl, 1-
(3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-
Phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2 -Phenylpropyl, 2- (4-chlorophenyl) -2-methylpropyl, 2-methyl-2- (3-methylphenyl) propyl, 1-phenylpentyl, 2-phenylpentyl, 3-phenylpentyl, 4-phenylpentyl , 5-phenylpentyl, 1-methyl-1-phenylbutyl, 1-methyl-2-phenylbutyl, 1-methyl-3-phenylbutyl, 1-methyl-4-phenylbutyl, 2-methyl-2-phenylbutyl , 2- (4-chlorophenyl) -2-methylbutyl, 2-methyl-2- (3-methylphenyl) butyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenyl Hexyl, 6-phenylhexyl 1-methyl-1-phenylpentyl, 1-methyl-2-phenylpentyl, 1-methyl-3-phenylpentyl, 1-methyl-4-phenylpentyl, 2-methyl-2-phenylpentyl, 2- (4- Examples include chlorophenyl) -2-methylpentyl and 2-methyl-2- (3-methylphenyl) pentyl.

The heteroaryl C ₁ -C ₆ alkyl optionally substituted by R ^a in the definition of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^c is a straight group. As a chain or branched heteroarylalkyl, pyridin-2-ylmethyl, 5-chlorothiophen-2-ylmethyl, 1-methyl-3-chloropyrazol-5-ylmethyl, 2- (3-methylfuran-2-
Yl) ethyl, 3- (6-trifluoromethylpyridine-2-
Yl) propyl, 4- (pyrimidin-2-yl) butyl, 5-
(1,2,4-triazol-1-yl) pentyl, 6- (pyrrol-1-yl) hexyl and the like can be mentioned.

R³, R^Five, R⁶, R⁷, R^b, R^c, X¹,
X², X³And X^FourIn the definition of^aHas been replaced with
As good phenyl, Ph, 2-Cl-Ph, 3-Cl-Ph, 4-Cl
-Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-Me-Ph, 3-Me-Ph, 4-M
e-Ph, 2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 4-Br-Ph, 2,4-C
l₂-Ph, 3,4-Cl₂-Ph, 2,4,6-Cl₃-Ph, 3,4- (MeO)₂-Ph, 2-
Cl-4-Me-Ph, 2-MeO-4-Me-Ph, 2-Cl-4-i-PrO-Ph, 3-Cl-4
-PhCH₂O-Ph, 2,4-Me₂-Ph, 2,5-Me₂-Ph, 2,6-F₂-Ph, 2,
3,4,5,6-F_Five-Ph, 4-Et-Ph, 4-i-Pr-Ph, 4-n-Bu-Ph, 4-s-
Bu-Ph, 4-t-Bu-Ph, 4- (t-BuCH₂) -Ph, 4-Et (Me)₂-Ph, 4-
n-Hex-Ph, 4-((Me)₂(CN) C) -Ph, 4- (MeCH = CH) -Ph, 4- (Me
C≡C) -Ph, 4-CF₃-Ph, 4-CF₃CH₂-Ph, 4- (Cl ₂C = CHCH₂) -P
h, 4- (BrC≡C) -Ph, 4- (2,2-F₂-c-BuCH₂) -Ph, 4- (1-Me-c
-Pr) -Ph, 4-i-PrO-Ph, 4-t-BuO-Ph, 4-n-HexO-Ph, 4-Me
CC (O) Ph, 4- (CH₂= CHCH₂O) -Ph, 4-CHF ₂O-Ph, 4-CBrF₂O-P
h, 4-CF₃O-Ph, 4-CF₃CH₂O-Ph, 4- (CF₂= CHCH₂CH₂O) -Ph,
4-CCl ₃CCH₂O-Ph, 4-MeS-Ph, 4-s-BuS-Ph, 4-EtSO-Ph, 4
-MeSO₂-Ph, 4-EtSO₂-Ph, 4-i-PrSO₂-Ph, 4-t-BuSO₂-P
h, 4- (MeCH = CHCH₂S) -Ph, 4- (CH₂= CHCH₂SO) -Ph, 4- (ClCH
= CHCH₂SO₂) -Ph, 4- (HC≡CCH₂S) -Ph, 4- (HC≡CCH₂SO-P
h), 4- (HC≡CCH₂SO₂) -Ph, 4-CHF₂S-Ph, 4-CBrF₂S-Ph, 4
-CF₃S-Ph, 4-CF₃CH₂S-Ph, 4-CHF₂CF₂S-Ph, 4-CHF₂SO-P
h, 4-CBrF₂SO-Ph, 4-CF₃SO-Ph, 4-CF₃CH₂SO₂-Ph, 4-CHF
₂CF₂SO₂-Ph, 4-CHF₂SO ₂-Ph, 4-CBrF₂SO₂-Ph, 4-CF₃SO₂-
Ph, 4- (Cl₂C = CHCH₂S) -Ph, 4- (Cl₂C = CHCH₂SO) -Ph, 4- (Cl
₂C = CHCH₂SO₂) -Ph, 4- (BrC≡CCH₂S) -Ph, 4- (BrC≡CCH₂S
O) -Ph, 4- (BrC≡CCH₂SO₂) -Ph, 4-CHO-Ph, 4-NO₂-Ph, 3-
CN-Ph, 4-CN-Ph, 4- (Me)₂N-Ph, 4-Me (MeC (O)) N-Ph, 4-P
hN (Me) -Ph, 4-PhCH₂(MeC (O)) N-Ph, 4-MeC (O) -Ph, 4-EtC
(O) -Ph, 4-n-PrC (O) -Ph, 4-i-PrC (O) -Ph, 4-i-BuC (O) -P
h, 4-t-BuC (O) -Ph, 4-i-BuCH₂C (O) -Ph, 4-Et (Me)₂C (O)-
Ph, 4-n-HexC (O) -Ph, 4-MeOCH₂-Ph, 4-EtOCH₂-Ph, 4-i-
PrOCH₂-Ph, 4-MeSCH₂-Ph, 4-EtSCH₂-Ph, 4-i-PrSCH₂-P
h, 4-CF₃C (O) -Ph, 4-CF₃CF₂C (O) -Ph, 4-MeC (O) O-Ph, 4-
EtC (O) O-Ph, 4-n-PrC (O) O-Ph, 4-i-PrC (O) O-Ph, 4-i-Bu
C (O) O-Ph, 4-t-BuC (O) O-Ph, 4-i-BuCH₂C (O) O-Ph, 4-Et
(Me)₂C (O) O-Ph, 4-n-HexC (O) O-Ph, 4-CF₃C (O) O-Ph, 4-C
F₃CF₂C (O) O-Ph, 3,5-Cl₂-Ph, 2,6-Cl₂-Ph, 2,5-Cl₂-P
h, 2,3-Cl₂-Ph, 2,3-F₂-Ph, 2,5-F₂-Ph, 3,4-F₂-Ph, 3,
5-F₂-Ph, 2,4-F₂-Ph, 2-CF₃-Ph, 3- (3-Cl-Ph, CH₂O) -P
h, 2-F-6-CF₃-Ph, 2-F-6-Cl-Ph, 2-F-6-Me-Ph, 2-F-6-M
eO-Ph, 2-F-6-OH-Ph, 2-F-6-MeS-Ph, 2-F-5-Cl-Ph, 2-F
-5-CF₃-Ph, 2-F-5-Me-Ph, 2-F-5-MeO-Ph, 2-F-5-OH-P
h, 2-F-5-MeS-Ph, 2-F-4-Cl-Ph, 2-F-4-CF₃-Ph, 2-F-4-
Me-Ph, 2-F-4-MeO-Ph, 2-F-3-Cl-Ph, 2-F-3-Me-Ph, 2-F
-3-MeO-Ph, 3-F-2-Cl-Ph, 3-F-2-Me-Ph, 3-F-2-MeO-P
h, 3-F-4-Cl-Ph, 3-F-4-Me-Ph, 3-F-4-MeO-Ph, 3-F-5-C
l-Ph, 3-F-5-Me-Ph, 3-F-5-MeO-Ph, 3-F-6-Cl-Ph, 3-F-
6-Me-Ph, 3-F-6-MeO-Ph, 4-F-2-Cl-Ph, 4-F-2-Me-Ph, 4
-F-2-MeO-Ph, 4-F-3-Cl-Ph, 4-F-3-Me-Ph, 4-F-3-MeO-P
h, 2,4,6-F₃-Ph, 2-OH-Ph, 4-I-Ph, 4-MeOC (O) -Ph, 4-M
eNHC (O) -Ph, 2,6-Me₂-Ph, 3-CF₃-Ph, 2-Br-Ph, 3-Br-P
h, 2-MeC (O) -Ph, 2-I-Ph, 3-I-Ph, 4-c-Pr-Ph, 4- (2-Cl
-c-Pr) -Ph, 4- (2,2-Cl₂-c-Pr) -Ph, 4- (Ph-CH = CH) -Ph, 4
-(Ph-C≡C) -Ph, 4-PhS-Ph, 4-HO-Ph, 4-EtO-Ph, 4-PenO
-Ph, 2-F-3-CF₃-Ph, 2,3-Me₂-Ph, 3,4-Me₂-Ph, 3,5-Me₂
-Ph, 2,3- (MeO)₂-Ph, 2,4- (MeO)₂-Ph, 2,5- (MeO)₂-Ph,
3,5- (MeO)₂-Ph, 2-F-3-I-Ph, 2-F-4-I-Ph, 2-F-5-I-P
h, 2-F-6-I-Ph, 2-F-4-EtO-Ph, 2-F-4-PrO-Ph, 2-F-4-i
-PrO-Ph, 2-F-4-BuO-Ph, 2-F-4-s-BuO-Ph, 2-F-4-i-BuO
-Ph, 2-F-4-t-BuO-Ph, 2-F-4-PenO-Ph, 2-F-4- (2-Me-Bu
O) -Ph, 2-F-4- (2,2-Me₂-PrO) -Ph, 2-F-4-HexO-Ph, 2-F-
4- (2-Et-Hex) O-Ph, 2-F-4-Et-Ph, 2-F-4-Pr-Ph, 2-F-4-
i-Pr-Ph, 2-F-4-Bu-Ph, 2-F-4-s-Bu-Ph, 2-F-4-i-Bu-P
h, 2-F-4-t-Bu-Ph, 2-F-4-Pen-Ph, 2-F-4- (2-Me-Bu) -P
h, 2-F-4- (2,2-Me₂-Pr) -Ph, 2-F-4-Hex-Ph, 2-F-4- (2-E
t-Hex) -Ph, 2-F-6-PhS-Ph, 2-F-6-Me₂N-Ph, 2-F-6-MeNH
-Ph, 2-F-6-Ph-Ph, 3,4-methylenedioxy-Ph, 3,4-ethyl
enedioxy-Ph, 2-F-3-Br-Ph, 2-F-4-Br-Ph, 2-F-5-Br-P
h, 2-F-6-Br-Ph, 3-F-2-Br-Ph, 3-F-4-Br-Ph, 3-F-5-Br
-Ph, 3-F-6-Br-Ph, 4-F-2-Br-Ph, 4-F-3-Br-Ph, 2-Cl-3
-Me-Ph, 2-Cl-4-Me-Ph, 2-Cl-5-Me-Ph, 2-Cl-6-Me-Ph,
3-Cl-2-Me-Ph, 3-Cl-4-Me-Ph, 3-Cl-5-Me-Ph, 3-Cl-6-M
e-Ph, 4-Cl-2-Me-Ph, 4-Cl-3-Me-Ph, 2,3-F₂-4-Me-Ph,
2,3-F₂-5-Me-Ph, 2,3-F₂-6-Me-Ph, 2,4-F₂-3-Me-Ph, 2,
4-F₂-5-Me-Ph, 2,4-F₂-6-Me-Ph, 2,5-F₂-3-Me-Ph, 2,5-
F₂-4-Me-Ph, 2,5-F₂-6-Me-Ph, 2,6-F₂-3-Me-Ph, 2,6-F₂
-4-Me-Ph, 2,3-F₂-4-Cl-Ph, 2,3-F₂-5-Cl-Ph, 2,3-F₂-6
-Cl-Ph, 2,4-F₂-3-Cl-Ph, 2,4-F₂-5-Cl-Ph, 2,4-F₂-6-C
l-Ph, 2,5-F₂-3-Cl-Ph, 2,5-F₂-4-Cl-Ph, 2,5-F₂-6-Cl-
Ph, 2,6-F₂-3-Cl-Ph, 2,6-F₂-4-Cl-Ph, 2,3-F₂-4-MeO-P
h, 2,3-F₂-5-MeO-Ph, 2,3-F₂-6-MeO-Ph, 2,4-F₂-3-MeO-
Ph, 2,4-F₂-5-MeO-Ph, 2,4-F₂-6-MeO-Ph, 2,5-F₂-3-MeO
-Ph, 2,5-F₂-4-MeO-Ph, 2,5-F₂-6-MeO-Ph, 2,6-F₂-3-Me
O-Ph, 2,6-F₂-4-MeO-Ph, 2,3-F₂-4-EtO-Ph, 2,3-F₂-5-E
tO-Ph, 2,3-F₂-6-EtO-Ph, 2,4-F₂-3-EtO-Ph, 2,4-F₂-Five-
EtO-Ph, 2,4-F₂-6-EtO-Ph, 2,5-F₂-3-EtO-Ph, 2,5-F₂-Four
-EtO-Ph, 2,5-F₂-6-EtO-Ph, 2,6-F₂-3-EtO-Ph, 2,6-F₂-
4-EtO-Ph, 2,3-F₂-4-Et-Ph, 2,3-F₂-5-Et-Ph, 2,3-F₂-6
-Et-Ph, 2,4-F₂-3-Et-Ph, 2,4-F₂-5-Et-Ph, 2,4-F₂-6-E
t-Ph, 2,5-F₂-3-Et-Ph, 2,5-F₂-4-Et-Ph, 2,5-F₂-6-Et-
Ph, 2,6-F₂-3-Et-Ph, 2,6-F₂-4-Et-Ph, 2,3-F₂-4-Br-P
h, 2,3-F₂-5-Br-Ph, 2,3-F₂-6-Br-Ph, 2,4-F₂-3-Br-P
h, 2,4-F₂-5-Br-Ph, 2,4-F₂-6-Br-Ph, 2,5-F₂-3-Br-P
h, 2,5-F₂-4-Br-Ph, 2,5-F₂-6-Br-Ph, 2,6-F₂-3-Br-P
h, 2,6-F₂-4-Br-Ph, 2,6-F₂-4-Pr-Ph, 2,6-F₂-4-i-Pr-P
h, 2,6-F₂-4-c-Pr-Ph, 2,6-F₂-4-Bu-Ph, 2,6-F₂-4-i-Bu
-Ph, 2,6-F₂-4-s-Bu-Ph, 2,6-F₂-4-t-Bu-Ph, 2,6-F₂-Four-
Pen-Ph, 2,6-F₂-4-Hex-Ph, 2,6-F₂-4-Ph-Ph, 2,6-F₂-Four-
PhCH₂-Ph, 2,6-F₂-4-PrO-Ph, 2,6-F₂-4-i-PrO-Ph, 2,6-
F₂-4-c-PrO-Ph, 2,6-F₂-4-BuO-Ph, 2,6-F₂-4-i-BuO-P
h, 2,6-F₂-4-s-BuO-Ph, 2,6-F₂-4-t-BuO-Ph, 2,6-F₂-Four-
PenO-Ph, 2,6-F₂-4-HexO-Ph, 2,6-F₂-4-PhO-Ph, 2,6-F₂
-4-PhCH₂O-Ph, 2-F-6-Cl-3-MeO-Ph, 2-F-6-Cl-4-MeO-P
h, 2-F-6-Cl-5-MeO-Ph, 2-F-6-Cl-3-Me-Ph, 2-F-6-Cl-4
-Me-Ph, 2-F-6-Cl-5-Me-Ph, 2-F-6-MeO-3-Cl-Ph, 2-F-6
-MeO-4-Cl-Ph, 2-F-6-MeO-5-Cl-Ph, 2-F-6-MeO-3-Me-P
h, 2-F-6-MeO-4-Me-Ph, 2-F-6-MeO-5-Me-Ph, 2,4,6-Me₃
-Ph, 2-Cl-3-MeO-Ph, 2-Cl-4-MeO-Ph, 2-Cl-5-MeO-Ph,
2-Cl-6-MeO-Ph, 3-Cl-2-MeO-Ph, 3-Cl-4-MeO-Ph, 3-Cl-
5-MeO-Ph, 3-Cl-6-MeO-Ph, 4-Cl-2-MeO-Ph, 4-Cl-3-MeO
-Ph, 2-Me-3-MeO-Ph, 2-Me-4-MeO-Ph, 2-Me-5-MeO-Ph,
2-Me-6-MeO-Ph, 3-Me-2-MeO-Ph, 3-Me-4-MeO-Ph, 3-Me-
5-MeO-Ph, 3-Me-6-MeO-Ph, 4-Me-3-MeO-Ph and 2,6- (M
eO)₂-Ph etc.

In R ⁵ , R ⁶ , R ⁷ , R ^b and R ^c ,
Optionally substituted with R ^a heteroaryl, heteroaryl sulfonyl optionally substituted by R ^a, optionally substituted with R ^a as defined in even better heteroarylcarbonyl, optionally substituted with R ^a Good heteroaryl includes 5-chlorothiophen-2-yl, 3,5-dimethylfuran-2-yl, 3-cyanopyrrol-1-yl, oxazol-2
-Yl, 2-methylsulfenyloxazol-4-yl, 4-
Methylthiazol-2-yl, 2-trifluoromethylimidazol-1-yl, isoxazol-3-yl, 3-chloroisoxazol-4-yl, 3-methylisothiazol-5-yl, 3-phenylpyrazol- 1-yl, 1-methylpyrazol-5-yl, 2-methylsulfonyl-1,3,4-oxadiazol-5-yl, 2-bromo-1,3,4-thiadiazol-2-yl,
1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-1-yl, 1,2,3-thiadiazol-5-yl, 1,2,3-triazol-1-yl, 1,2,3,
4-tetrazol-1-yl, 6-phenoxypyridin-2-yl, 6-methoxypyrimidin-2-yl, pyrazin-2-yl,
Pyridazin-3-yl, 1,3,5-triazin-2-yl and 1,
2,4-triazin-6-yl and the like can be mentioned.

[0078] ^{R 5, R 6, R 7} , R b, R c, X 1, in X ³ and X ^4, which may be substituted by R ^a phenyl sulfonyl optionally substituted by and R ^a phenyl The phenyl optionally substituted by R ^a , which is defined by carbonyl, is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2- Bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-4-chlorophenyl , 2,3,4,5,6-pentafluorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,5-dimethylphenyl, 4-methyl-2,3,5,6-tetra Fluorophenyl, 2-me Kishifeniru, 3-methoxyphenyl, 4-methoxyphenyl, 2,6
Dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-
Examples thereof include trimethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl and 4-trifluoromethylphenyl.

R^Five, R⁶, R⁷, R^bAnd R^cIn
R^aPhenyl C optionally substituted with₁~ C₆Alkyl
Sulfonyl and R^aPhenyl optionally substituted with
C₁~ C ₆R defined by alkylcarbonyl^aReplace with
Optionally phenyl C₁~ C₆As alkyl,
Benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chloro
Lolobenzyl, 4-methylbenzyl, 4-t-butylbenzi
2-methylbenzyl, 2-methoxybenzyl, 1-phenyl
Ruethyl, 1- (3-chlorophenyl) ethyl, 2-phenyl
Ethyl, 1-methyl-1-phenylethyl, 1- (4-chlorophenyl
Phenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-
Methyl ethyl, 1-phenyl propyl, 2-phenyl propyl
, 3-phenylpropyl, 1-phenylbutyl, 2-phenyl
Rubutyl, 3-phenylbutyl, 4-phenylbutyl, 1-medium
Cyl-1-phenylpropyl, 1-methyl-2-phenylpropy
1-methyl-3-phenylpropyl, 2-methyl-2-phenyl
Rupropyl, 2- (4-chlorophenyl) -2-methylpropyi
2-methyl-2- (3-methylphenyl) propyl, 1-f
Phenyl pentyl, 2-phenyl pentyl, 3-phenyl pen
Chill, 4-phenylpentyl, 5-phenylpentyl, 1-me
Tyl-1-phenylbutyl, 1-methyl-2-phenylbutyl,
1-methyl-3-phenylbutyl, 1-methyl-4-phenylbuty
2-methyl-2-phenylbutyl, 2- (4-chlorophenyl
) -2-methylbutyl, 2-methyl-2- (3-methylphenyl)
) Butyl, 1-phenylhexyl, 2-phenylhexyl
3-phenylhexyl, 4-phenylhexyl, 5-phen
Nylhexyl, 6-phenylhexyl, 1-methyl-1-phen
Nylpentyl, 1-methyl-2-phenylpentyl, 1-methyl
Lu-3-phenylpentyl, 1-methyl-4-phenylpentyl
2-methyl-2-phenylpentyl, 2- (4-chlorophene
Nyl) -2-methylpentyl and 2-methyl-2- (3-methyl
Phenyl) pentyl and the like.

[0080] ^{R 7, R b, R c} , in X ^1, X ³ and X ^4, is defined by also good phenoxycarbonyl substituted with R ^a in an optionally substituted phenoxy and R ^a, R Examples of phenoxy which may be substituted with ^a include phenoxy, 2-fluorophenoxy, 3-fluorophenoxy, 4-fluorophenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2-bromophenoxy and 3 -Bromophenoxy, 4-bromophenoxy, 4-iodophenoxy, 2,4-dichlorophenoxy, 3,
4-dichlorophenoxy, 2,6-difluorophenoxy, 2,
6-dichlorophenoxy, 2-fluoro-4-chlorophenoxy, 2,3,4,5,6-pentafluorophenoxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy,
2,5-Dimethylphenoxy, 4-methyl-2,3,5,6-tetrafluorophenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-methoxyphenoxy, 2,6-dimethoxyphenoxy, 3,4-dimethoxy Phenoxy, 3,4,5-trimethoxyphenoxy, 2-trifluoromethylphenoxy, 3-
Examples thereof include trifluoromethylphenoxy and 4-trifluoromethylphenoxy.

In the definition of R ⁷ , R ^b and R ^c , the phenyl C ₁ -C ₆ alkoxy which may be substituted with R ^a is benzyloxy or 2-chlorobenzyl which may be linear or branched phenylalkoxy. Oxy, 3-bromobenzyloxy, 4-chlorobenzyloxy, 4-methylbenzyloxy, 4-t-butylbenzyloxy, 2-methylbenzyloxy, 2-methoxybenzyloxy, 1-phenylethyloxy, 1- (3 -Chlorophenyl) ethyloxy, 2-
Phenylethyloxy, 1-methyl-1-phenylethyloxy, 1- (4-chlorophenyl) -1-methylethyloxy, 1- (3-chlorophenyl) -1-methylethyloxy, 1
-Phenylpropyloxy, 2-phenylpropyloxy, 3-phenylpropyloxy, 1-phenylbutyloxy, 2-phenylbutyloxy, 3-phenylbutyloxy, 4-phenylbutyloxy, 1-methyl-1-phenylpropyloxy , 1-methyl-2-phenylpropyloxy, 1
-Methyl-3-phenylpropyloxy, 2-methyl-2-phenylpropyloxy, 2- (4-chlorophenyl) -2-methyl-propyloxy, 2-methyl-2- (3-methylphenyl) propyloxy, 1 -Phenylpentyloxy, 2-phenylpentyloxy, 3-phenylpentyloxy, 4-
Phenylpentyloxy, 5-phenylpentyloxy,
1-methyl-1-phenylbutyloxy, 1-methyl-2-phenylbutyloxy, 1-methyl-3-phenylbutyloxy, 1
-Methyl-4-phenylbutyloxy, 2-methyl-2-phenylbutyloxy, 2- (4-chlorophenyl) -2-methylbutyloxy, 2-methyl-2- (3-methylphenyl) butyloxy, 1-phenyl Hexyloxy, 2-phenylhexyloxy, 3-phenylhexyloxy, 4-phenylhexyloxy, 5-phenylhexyloxy, 6-phenylhexyloxy, 1-methyl-1-phenylpentyloxy, 1
-Methyl-2-phenylpentyloxy, 1-methyl-3-phenylpentyloxy, 1-methyl-4-phenylpentyloxy, 2-methyl-2-phenylpentyloxy, 2- (4-chlorophenyl) -2-methyl Examples include pentyloxy and 2-methyl-2- (3-methylphenyl) pentyloxy.

[0082] in R ^7, R ^b and R ^c, optionally substituted with R ^a in optionally substituted heteroaryloxy, and R ^a is also defined in good heteroaryloxycarbonyl, substituted by R ^a As the heteroaryloxy which may be present, 5-chlorothiophen-2-yloxy,
3,5-dimethylfuran-2-yloxy, 3-cyano-pyrrole
-1-yloxy, oxazol-2-yloxy, 2-methylsulphenyloxazol-4-yloxy, 4-methylthiazol-2-yloxy, 2-trifluoromethylimidazol-4-yloxy, isoxazol-3-yloxy,
3-chloroisoxazol-4-yloxy, 3-methylisothiazol-5-yloxy, 1-benzyl-3-phenylpyrazol-5-yloxy, 1-methylpyrazol-5-yloxy, 2-methylsulfonyl-1, 3,4-oxadiazol-5-yloxy, 2-bromo-1,3,4-thiadiazol-2-yloxy, 1,2,4-oxadiazol-3-yloxy, 1,2,4-thiadiazole- 5-yloxy, 1,2,4-triazol-3-yloxy, 1,2,3-thiadiazol-5-yloxy, 1,2,3
-Triazol-5-yloxy, 1,2,3,4-tetrazole-5
-Yloxy, 6-phenoxypyridin-2-yloxy, 6-
Methoxypyrimidin-2-yloxy, pyrazin-2-yloxy, pyridazin-3-yloxy, 1,3,5-triazine-2-
Iloxy, 1,2,4-triazin-6-yloxy and the like can be mentioned.

[0083] in R ^c, R ^a which may be phenyl sulfenyl substituted with, is defined by R ^a phenyl sulfone optionally substituted by alkylsulfonyl and R ^a optionally substituted by phenyl carbonyloxy, R ^The phenyl which may be substituted with ^a includes phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl and 3-bromophenyl. , 4-bromophenyl, 4-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-difluorophenyl,
2,6-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,3,4,5,6-pentafluorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,5-dimethylphenyl, 4-methyl-2,3,5,6-tetrafluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,6-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5 -Trimethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl and the like.

[0084] in R ^c, optionally substituted with R ^a in optionally substituted phenyl C ₁ -C ₆ alkylsulfenyl, phenyl optionally substituted with R ^a C ₁ -C ₆ alkylsulfinyl and R ^a Phenyl C ₁ -C ₆ alkyl optionally substituted with R ^a defined by phenyl C ₁ -C ₆ alkylcarbonyloxy includes benzyl and 2-chlorobenzyl as linear or branched phenylalkyl. , 3-bromobenzyl, 4-chlorobenzyl, 4-
Methylbenzyl, 4-t-butylbenzyl, 2-methylbenzyl, 2-methoxybenzyl, 1-phenylethyl, 1- (3-
Chlorophenyl) ethyl, 2-phenylethyl, 1-methyl
-1-phenylethyl, 1- (4-chlorophenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-methylethyl, 1-
Phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl , 1-methyl-3-
Phenylpropyl, 2-methyl-2-phenylpropyl, 2-
(4-chlorophenyl) -2-methylpropyl, 2-methyl-2-
(3-methylphenyl) propyl, 1-phenylpentyl,
2-phenylpentyl, 3-phenylpentyl, 4-phenylpentyl, 5-phenylpentyl, 1-methyl-1-phenylbutyl, 1-methyl-2-phenylbutyl, 1-methyl-3-phenylbutyl, 1-methyl -4-phenylbutyl, 2-methyl-2-
Phenylbutyl, 2- (4-chlorophenyl) -2-methylbutyl, 2-methyl-2- (3-methylphenyl) butyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5 -Phenylhexyl, 6-phenylhexyl, 1-methyl-1-phenylpentyl, 1-methyl-2-phenylpentyl, 1-methyl-3-phenylpentyl, 1-methyl-4-phenylpentyl, 2-methyl-2 -Phenylpentyl, 2- (4-chlorophenyl) -2-methylpentyl, 2-methyl-2- (3-methylphenyl) pentyl and the like can be mentioned.

[0085] in R ^c, R ^a with optionally substituted heteroaryl arylsulfinyl, defined by R ^a in the optionally substituted heteroaryl sulfenyl and may be substituted by R ^a heteroarylcarbonyloxy Examples of the heteroaryl optionally substituted with R ^a include 5-chlorothiophen-2-yl, 3,5-dimethylfuran-
2-yl, 3-cyanopyrrol-1-yl, oxazol-2-yl, 2-methylsulphenyloxazol-4-yl, 4-methylthiazol-2-yl, 2-trifluoromethylimidazol-1-yl, Isoxazol-3-yl, 3-chloroisoxazol-4-yl, 3-methylisothiazol-5-yl,
3-phenylpyrazol-1-yl, 1-methylpyrazol-5-
2-methylsulfonyl-1,3,4-oxadiazole-5-yl
2-bromo-1,3,4-thiadiazol-2-yl, 1,2,4-
Oxadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-1-yl, 1,2,3-thiadiazol-5-yl, 1,2,3- Triazol-1-yl, 1,2,3,4-tetrazol-1-yl, 6-phenoxypyridin-2-yl, 6-methoxypyrimidin-2-yl, pyrazin-2-yl, pyridazin-3-yl, Examples include 1,3,5-triazin-2-yl and 1,2,4-triazin-6-yl.

Heteroaryl C ₁ -C ₆ alkoxy optionally substituted by R ^a in the definition of R ^c is pyridin-2-ylmethyloxy, 5-chlorothiophene as a linear or branched heteroarylalkoxy. -2-ylmethyloxy, 1-methyl-3-chloropyrazol-5-ylmethyloxy, 2- (3-methylfuran-2-yl) ethyloxy, 3- (6-trifluoromethylpyridin-2-yl) Propyloxy, 4- (pyrimidin-2-yl) butyloxy, 5
Examples include- (triazol-1-yl) pentyloxy and 6- (pyrrol-1-yl) hexyloxy.

In R ^c , ^a heteroaryl C ₁ -C ₆ alkylsulfenyl optionally substituted with R ^a , ^a heteroaryl C ₁ -C ₆ alkylsulfinyl optionally substituted with R ^a , substituted with R ^a Optionally substituted heteroaryl C ₁ -C ₆ alkylsulfonyl, optionally substituted R ^a heteroaryl C ₁ -C ₆ alkylcarbonyloxy defined as optionally substituted R ^a heteroaryl Examples of C ₁ -C ₆ alkyl include pyridin-2-ylmethyl, 5-chlorothiophen-2-ylmethyl, 1-methyl-3-chloropyrazol-5-ylmethyl and 2- (as linear or branched heteroarylalkyl. 3-methylfuran-2-
Yl) ethyl, 3- (6-trifluoromethylpyridine-2-
Yl) propyl, 4- (pyrimidin-2-yl) butyl, 5-
(Triazol-1-yl) pentyl and 6- (pyrrole-
1-yl) hexyl and the like can be mentioned.

R in Y '^cMay be replaced with
I phenyl, R^cPhenylsul which may be substituted with
Phenyl, R^cPhenylsulf that may be substituted with
Inyl, R^cPhenylsulfoni which may be substituted with
Le, R^cPhenylcarbonyl which may be substituted with
And R^cPhenylcarbonyl which may be substituted with
R defined by xy^cPhenyl optionally substituted with
As, Ph, 2-Cl-Ph, 3-Cl-Ph, 4-Cl-Ph, 2-F-Ph, 3
-F-Ph, 4-F-Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph, 2-MeO-P
h, 3-MeO-Ph, 4-MeO-Ph, 4-Br-Ph, 2,4-Cl₂-Ph, 3,4-Cl
₂-Ph, 2,4,6-Cl₃-Ph, 3,4- (MeO)₂-Ph, 2-Cl-4-Me-Ph, 2
-MeO-4-Me-Ph, 2-Cl-4-i-PrO-Ph, 3-Cl-4-PhCH ₂O-Ph,
2,4-Me₂-Ph, 2,5-Me₂-Ph, 2,6-F₂-Ph, 2,3,4,5,6-F_Five-P
h, 4-Et-Ph, 4-i-Pr-Ph, 4-n-Bu-Ph, 4-s-Bu-Ph, 4-t-B
u-Ph, 4- (t-BuCH₂) -Ph, 4-Et (Me)₂-Ph, 4-n-Hex-Ph, 4-
((Me)₂(CN) C) -Ph, 4-PhCH₂-Ph, 4- (4-F-Ph) (Me)₂-Ph, 4
-(MeCH = CH) -Ph, 4- (MeC≡C) -Ph, 4-CF₃-Ph, 4-CF₃CH₂-P
h, 4- (Cl₂C = CHCH₂) -Ph, 4- (BrC≡C) -Ph, 4- (2,2-F₂-c-B
uCH₂) -Ph, 4- (1-Me-c-Pr) -Ph, 4-i-PrO-Ph, 4-t-BuO-P
h, 4-n-HexO-Ph, 4-MeCC (O) Ph, 4- (CH₂= CHCH₂O) -Ph, 4
-CHF₂O-Ph, 4-CBrF₂O-Ph, 4-CF₃O-Ph, 4-CF₃CH₂O-Ph, 4
-(CF₂= CHCH₂CH₂O) -Ph, 4-CCl₃CCH₂O-Ph, 4-MeS-Ph, 4-s
-BuS-Ph, 4-EtSO-Ph, 4-MeSO₂-Ph, 4-EtSO₂-Ph, 4-i-Pr
SO₂-Ph, 4-t-BuSO₂-Ph, 4- (MeCH = CHCH₂S) -Ph, 4- (CH₂= C
HCH₂SO) -Ph, 4- (ClCH = CHCH₂SO₂) -Ph, 4- (HC≡CCH₂S) -P
h, 4- (HC≡CCH₂SO-Ph), 4- (HC≡CCH₂SO₂) -Ph, 4-CHF₂S-
Ph, 4-CBrF₂S-Ph, 4-CF₃S-Ph, 4-CF₃CH₂S-Ph, 4-CHF₂CF
₂S-Ph, 4-CHF₂SO-Ph, 4-CBrF₂SO-Ph, 4-CF₃SO-Ph, 4-CF
₃CH₂SO₂-Ph, 4-CHF₂CF₂SO₂-Ph, 4-CHF₂SO₂-Ph, 4-CBrF₂
SO₂-Ph, 4-CF₃SO₂-Ph, 4- (Cl₂C = CHCH₂S) -Ph, 4- (Cl₂C = C
HCH₂SO) -Ph, 4- (Cl₂C = CHCH₂SO₂) -Ph, 4- (BrC≡CCH₂S) -P
h, 4- (BrC≡CCH₂SO) -Ph, 4- (BrC≡CCH₂SO₂) -Ph, 4-CHO-
Ph, 4-NO₂-Ph, 3-CN-Ph, 4-CN-Ph, 4- (Me)₂N-Ph, 4-Me
(MeC (O)) N-Ph, 4-PhMeN-Ph, 4-PhCH₂(MeC (O)) N-Ph, 4-P
hCH₂O-Ph, 4- (2-Cl-Ph) CH₂O-Ph, 4- (3-Cl-Ph) CH₂O-Ph,
4- (4-Cl-Ph) CH₂O-Ph, 4- (2-Me-Ph) CH₂O-Ph, 4- (3-Me-P
h) CH₂O-Ph, 4- (4-F-Ph) CH₂O-Ph, 4- (4-Et-Ph) CH₂O-Ph,
4- (2-Cl-Ph) CH₂S-Ph, 4- (3-Cl-Ph) CH₂S-Ph, 4- (4-Cl-P
h) CH₂SO-Ph, 4- (2-Me-Ph) CH₂S-Ph, 4- (3-Me-Ph) CH₂SO₂-
Ph, 4- (2,4-F₂-Ph) CH₂O-Ph, 3- (3,4-Cl₂-Ph) CH₂O-Ph, 4
-(2,5-Me₂-Ph) CH₂O-Ph, 4- (2,3,5,6-F_Five-Ph) CH₂O-Ph, 4-
MeC (O) -Ph, 4-EtC (O) -Ph, 4-n-PrC (O) -Ph, 4-i-PrC (O)-
Ph, 4-i-BuC (O) -Ph, 4-t-BuC (O) -Ph, 4-i-BuCH₂C (O) -P
h, 4-Et (Me)₂C (O) -Ph, 4-n-HexC (O) -Ph, 4-PhC (O) -Ph,
4- (2-Cl-Ph) C (O) -Ph, 4- (3-Br-Ph) C (O) -Ph, 4- (4-Cl-P
h) C (O) -Ph, 4- (2-Me-Ph) C (O) -Ph, 4-MeOCH₂-Ph, 4-EtOC
H₂-Ph, 4-i-PrOCH₂-Ph, 4-MeSCH₂-Ph, 4-EtSCH₂-Ph, 4-
i-PrSCH₂-Ph, 4-CF₃C (O) -Ph, 4-CF₃CF₂C (O) -Ph, 4-MeC
(O) O-Ph, 4-EtC (O) O-Ph, 4-n-PrC (O) O-Ph, 4-i-PrC (O) O
-Ph, 4-i-BuC (O) O-Ph, 4-t-BuC (O) O-Ph, 4-i-BuCH₂C (O)
O-Ph, 4-Et (Me)₂C (O) O-Ph, 4-n-HexC (O) O-Ph, 4-CF₃C
(O) O-Ph, 4-CF₃CF₂C (O) O-Ph, 4-PhC (O) O-Ph, 3-Ph-Ph,
4-Ph-Ph, 4- (4-Cl-Ph) -Ph, 4- (2,5-Me₂-Ph) -3-Me-Ph, 3
-PhO-Ph, 4-PhO-Ph, 4- (4-Cl-Ph) O-Ph, 4- (4-Me-Ph) O-P
h, 4- (4-F-Ph) O-Ph, 4- (4-MeO-Ph) O-Ph, 4- (2,4-Cl₂-P
h) O-Ph, 4- (3,4-Cl₂-Ph) O-Ph, 4- (2-Pyridyl) -Ph, 4- (5
-Cl-2-Pyridyl) -Ph, 2,3-Cl₂-Ph, 3,5-Cl₂-Ph, 2,6-Cl₂
-Ph, 2,5-Cl₂-Ph, 2,3-F₂-Ph, 2,5-F₂-Ph, 3,4-F₂-Ph,
3,5-F₂-Ph, 2,4-F₂-Ph, 2-CF₃-Ph, 3- (3-Cl-PhCH₂O) -P
h, 2-F-6-CF₃-Ph, 2-F-6-Cl-Ph, 2-F-6-Me-Ph, 2-F-6-M
eO-Ph, 2-F-6-OH-Ph, 2-F-6-MeS-Ph, 2-F-5-Cl-Ph, 2-F
-5-CF₃-Ph, 2-F-5-Me-Ph, 2-F-5-MeO-Ph, 2-F-5-OH-P
h, 2-F-5-MeS-Ph, 2-F-4-Cl-Ph, 2-F-4-CF₃-Ph, 2-F-4-
Me-Ph, 2-F-4-MeO-Ph, 2-F-3-Cl-Ph, 2-F-3-Me-Ph, 2-F
-3-MeO-Ph, 3-F-2-Cl-Ph, 3-F-2-Me-Ph, 3-F-2-MeO-P
h, 3-F-4-Cl-Ph, 3-F-4-Me-Ph, 3-F-4-MeO-Ph, 3-F-5-C
l-Ph, 3-F-5-Me-Ph, 3-F-5-MeO-Ph, 3-F-6-Cl-Ph, 3-F-
6-Me-Ph, 3-F-6-MeO-Ph, 4-F-2-Cl-Ph, 4-F-2-Me-Ph, 4
-F-2-MeO-Ph, 4-F-3-Cl-Ph, 4-F-3-Me-Ph, 4-F-3-MeO-P
h, 2,4,6-F₃-Ph, 2-OH-Ph, 4-I-Ph, 4-MeOC (O) -Ph, 4-M
eNHCO-Ph, 2,6-Me₂-Ph, 2,6- (MeO)₂-Ph, 4- (6-F-5-CF₃-
2-Pyridyl) -Ph, 4- (2-Pyridyl) O-Ph, 4- (5-Cl-2-Pyridy
l) O-Ph, 4- (3-Cl-5-F-2-Pyridyl) O-Ph, 4- (5-Cl-2-Thie
nyl) O-Ph, 3-CF₃-Ph, 2-Br-Ph, 3-Br-Ph, 2-MeC (O) -P
h, 2-I-Ph, 3-I-Ph, 4-c-Pr-Ph, 4- (2-Cl-c-Pr) -Ph, 4-
(2,2-Cl₂-c-Pr) -Ph, 4- (Ph-CH = CH) -Ph, 4- (Ph-C≡C) -P
h, 4-PhS-Ph, 4-HO-Ph, 4-EtO-Ph, 4-PenO-Ph, 2-F-3-C
F₃-Ph, 2,3-Me₂-Ph, 3,4-Me₂-Ph, 3,5-Me₂-Ph, 2,3- (Me
O)₂-Ph, 2,4- (MeO)₂-Ph, 2,5- (MeO)₂-Ph, 3,5- (MeO)₂-P
h, 2-F-3-I-Ph, 2-F-4-I-Ph, 2-F-5-I-Ph, 2-F-6-I-P
h, 2-F-4-EtO-Ph, 2-F-4-PrO-Ph, 2-F-4-i-PrO-Ph, 2-F
-4-BuO-Ph, 2-F-4-s-BuO-Ph, 2-F-4-i-BuO-Ph, 2-F-4-t
-BuO-Ph, 2-F-4-PenO-Ph, 2-F-4- (2-Me-BuO) -Ph, 2-F-4
-(2,2-Me₂-PrO) -Ph, 2-F-4-HexO-Ph, 2-F-4- (2-Et-Hex)
O-Ph, 2-F-4-Et-Ph, 2-F-4-Pr-Ph, 2-F-4-i-Pr-Ph, 2-F
-4-Bu-Ph, 2-F-4-s-Bu-Ph, 2-F-4-i-Bu-Ph, 2-F-4-t-Bu
-Ph, 2-F-4-Pen-Ph, 2-F-4- (2-Me-Bu) -Ph, 2-F-4- (2,2-
Me₂-Pr) -Ph, 2-F-4-Hex-Ph, 2-F-4- (2-Et-Hex) -Ph, 2-F
-6-PhS-Ph, 2-F-6-Me₂N-Ph, 2-F-6-MeNH-Ph, 2-F-6-Ph-
Ph, 3,4-methylenedioxy-Ph, 3,4-ethylenedioxy-Ph, 2
-F-3-Br-Ph, 2-F-4-Br-Ph, 2-F-5-Br-Ph, 2-F-6-Br-P
h, 3-F-2-Br-Ph, 3-F-4-Br-Ph, 3-F-5-Br-Ph, 3-F-6-Br
-Ph, 4-F-2-Br-Ph, 4-F-3-Br-Ph, 2-Cl-3-Me-Ph, 2-Cl-
4-Me-Ph, 2-Cl-5-Me-Ph, 2-Cl-6-Me-Ph, 3-Cl-2-Me-P
h, 3-Cl-4-Me-Ph, 3-Cl-5-Me-Ph, 3-Cl-6-Me-Ph, 4-Cl-
2-Me-Ph, 4-Cl-3-Me-Ph, 2,3-F₂-4-Me-Ph, 2,3-F₂-5-Me
-Ph, 2,3-F₂-6-Me-Ph, 2,4-F₂-3-Me-Ph, 2,4-F₂-5-Me-P
h, 2,4-F₂-6-Me-Ph, 2,5-F₂-3-Me-Ph, 2,5-F₂-4-Me-P
h, 2,5-F₂-6-Me-Ph, 2,6-F₂-3-Me-Ph, 2,6-F₂-4-Me-P
h, 2,3-F₂-4-Cl-Ph, 2,3-F₂-5-Cl-Ph, 2,3-F₂-6-Cl-P
h, 2,4-F₂-3-Cl-Ph, 2,4-F₂-5-Cl-Ph, 2,4-F₂-6-Cl-P
h, 2,5-F₂-3-Cl-Ph, 2,5-F₂-4-Cl-Ph, 2,5-F₂-6-Cl-P
h, 2,6-F₂-3-Cl-Ph, 2,6-F₂-4-Cl-Ph, 2,3-F₂-4-MeO-P
h, 2,3-F₂-5-MeO-Ph, 2,3-F₂-6-MeO-Ph, 2,4-F₂-3-MeO-
Ph, 2,4-F₂-5-MeO-Ph, 2,4-F₂-6-MeO-Ph, 2,5-F₂-3-MeO
-Ph, 2,5-F₂-4-MeO-Ph, 2,5-F₂-6-MeO-Ph, 2,6-F₂-3-Me
O-Ph, 2,6-F₂-4-MeO-Ph, 2,3-F₂-4-EtO-Ph, 2,3-F₂-5-E
tO-Ph, 2,3-F₂-6-EtO-Ph, 2,4-F₂-3-EtO-Ph, 2,4-F₂-Five-
EtO-Ph, 2,4-F₂-6-EtO-Ph, 2,5-F₂-3-EtO-Ph, 2,5-F₂-Four
-EtO-Ph, 2,5-F₂-6-EtO-Ph, 2,6-F₂-3-EtO-Ph, 2,6-F₂-
4-EtO-Ph, 2,3-F₂-4-Et-Ph, 2,3-F₂-5-Et-Ph, 2,3-F₂-6
-Et-Ph, 2,4-F₂-3-Et-Ph, 2,4-F₂-5-Et-Ph, 2,4-F₂-6-E
t-Ph, 2,5-F₂-3-Et-Ph, 2,5-F₂-4-Et-Ph, 2,5-F₂-6-Et-
Ph, 2,6-F₂-3-Et-Ph, 2,6-F₂-4-Et-Ph, 2,3-F₂-4-Br-P
h, 2,3-F₂-5-Br-Ph, 2,3-F₂-6-Br-Ph, 2,4-F₂-3-Br-P
h, 2,4-F₂-5-Br-Ph, 2,4-F₂-6-Br-Ph, 2,5-F₂-3-Br-P
h, 2,5-F₂-4-Br-Ph, 2,5-F₂-6-Br-Ph, 2,6-F₂-3-Br-P
h, 2,6-F₂-4-Br-Ph, 2,6-F₂-4-Pr-Ph, 2,6-F₂-4-i-Pr-P
h, 2,6-F₂-4-c-Pr-Ph, 2,6-F₂-4-Bu-Ph, 2,6-F₂-4-i-Bu
-Ph, 2,6-F₂-4-s-Bu-Ph, 2,6-F₂-4-t-Bu-Ph, 2,6-F₂-Four-
Pen-Ph, 2,6-F₂-4-Hex-Ph, 2,6-F₂-4-Ph-Ph, 2,6-F₂-Four-
PhCH₂-Ph, 2,6-F₂-4-PrO-Ph, 2,6-F₂-4-i-PrO-Ph, 2,6-
F₂-4-c-PrO-Ph, 2,6-F₂-4-BuO-Ph, 2,6-F₂-4-i-BuO-P
h, 2,6-F₂-4-s-BuO-Ph, 2,6-F ₂-4-t-BuO-Ph, 2,6-F₂-Four-
PenO-Ph, 2,6-F₂-4-HexO-Ph, 2,6-F₂-4-PhO-Ph, 2,6-F ₂
-4-PhCH₂O-Ph, 2-F-6-Cl-3-MeO-Ph, 2-F-6-Cl-4-MeO-P
h, 2-F-6-Cl-5-MeO-Ph, 2-F-6-Cl-3-Me-Ph, 2-F-6-Cl-4
-Me-Ph, 2-F-6-Cl-5-Me-Ph, 2-F-6-MeO-3-Cl-Ph, 2-F-6
-MeO-4-Cl-Ph, 2-F-6-MeO-5-Cl-Ph, 2-F-6-MeO-3-Me-P
h, 2-F-6-MeO-4-Me-Ph, 2-F-6-MeO-5-Me-Ph, 4-HepO-P
h, 4-OctO-Ph, 4-NonO-Ph, 4-DecO-Ph, 4-UndecO-Ph, 4
-DodecO-Ph, 4-Hep-Ph, 4-Oct-Ph, 4-Non-Ph, 4-Dec-P
h, 4-Undec-Ph, 4-Dodec-Ph, 2-Cl-4-HepO-Ph, 2-Cl-4-
OctO-Ph, 2-Cl-4-NonO-Ph, 2-Cl-4-DecO-Ph, 2-Cl-4-Un
decO-Ph, 2-Cl-4-DodecO-Ph, 2-Cl-4-Hep-Ph, 2-Cl-4-O
ct-Ph, 2-Cl-4-Non-Ph, 2-Cl-4-Dec-Ph, 2-Cl-4-Undec-
Ph, 2-Cl-4-Dodec-Ph, 3-Cl-4-HepO-Ph, 3-Cl-4-OctO-P
h, 3-Cl-4-NonO-Ph, 3-Cl-4-DecO-Ph, 3-Cl-4-UndecO-P
h, 3-Cl-4-DodecO-Ph, 3-Cl-4-Hep-Ph, 3-Cl-4-Oct-P
h, 3-Cl-4-Non-Ph, 3-Cl-4-Dec-Ph, 3-Cl-4-Undec-Ph,
3-Cl-4-Dodec-Ph, 2-F-4-HepO-Ph, 2-F-4-OctO-Ph, 2-F
-4-NonO-Ph, 2-F-4-DecO-Ph, 2-F-4-UndecO-Ph, 2-F-4-
DodecO-Ph, 2-F-4-Hep-Ph, 2-F-4-Oct-Ph, 2-F-4-Non-P
h, 2-F-4-Dec-Ph, 2-F-4-Undec-Ph, 2-F-4-Dodec-Ph, 3
-F-4-HepO-Ph, 3-F-4-OctO-Ph, 3-F-4-NonO-Ph, 3-F-4-
DecO-Ph, 3-F-4-UndecO-Ph, 3-F-4-DodecO-Ph, 3-F-4-H
ep-Ph, 3-F-4-Oct-Ph, 3-F-4-Non-Ph, 2-Cl-3-MeO-Ph,
2-Cl-4-MeO-Ph, 2-Cl-5-MeO-Ph, 2-Cl-6-MeO-Ph, 3-Cl-
2-MeO-Ph, 3-Cl-4-MeO-Ph, 3-Cl-5-MeO-Ph, 3-Cl-6-MeO
-Ph, 4-Cl-2-MeO-Ph, 4-Cl-3-MeO-Ph, 2-Me-3-MeO-Ph,
2-Me-4-MeO-Ph, 2-Me-5-MeO-Ph, 2-Me-6-MeO-Ph, 3-Me-
2-MeO-Ph, 3-Me-4-MeO-Ph, 3-Me-5-MeO-Ph, 3-Me-6-MeO
-Ph, 4-Me-3-MeO-Ph, 3-F-4-Dec-Ph, 3-F-4-Undec-Ph,
3-F-4-Dodec-Ph and 2,4,6-Me₃-Ph etc.

[0089] in Y ', R ^c substituted by phenyl C ₁ optionally -C ₆ alkyl, by phenyl C ₁ optionally -C ₆ alkylsulfenyl-substituted with R ^c, optionally substituted with R ^c also phenyl C ₁ -C ₆ alkylsulfinyl, substituted phenyl C ₁ optionally -C ₆ alkylsulfonyl in R ^c, with R phenyl optionally substituted by ^c C ₁ -C ₆ alkylcarbonyl and R ^c optionally substituted as defined in a phenyl C ₁ -C ₆ alkylcarbonyloxy, phenyl optionally substituted by R ^c C ₁
~ C ₆ alkyl includes benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl and 4-t-as linear or branched phenylalkyl.
Butylbenzyl, 2-methylbenzyl, 2-methoxybenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1
-(4-chlorophenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-
Phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-
Phenylpropyl, 1-methyl-3-phenylpropyl, 2-
Methyl-2-phenylpropyl, 2- (4-chlorophenyl)-
2-methylpropyl, 2-methyl-2- (3-methylphenyl)
Propyl, 1-phenylpentyl, 2-phenylpentyl,
3-phenylpentyl, 4-phenylpentyl, 5-phenylpentyl, 1-methyl-1-phenylbutyl, 1-methyl-2-phenylbutyl, 1-methyl-3-phenylbutyl, 1-methyl-
4-phenylbutyl, 2-methyl-2-phenylbutyl, 2- (4
-Chlorophenyl) -2-methylbutyl, 2-methyl-2- (3-
Methylphenyl) butyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenylhexyl, 1-methyl-1-phenylpentyl, 1-methyl-2- Phenylpentyl, 1-methyl-3-phenylpentyl, 1-methyl-4-phenylpentyl, 2-methyl-2-phenylpentyl, 2- (4-chlorophenyl) -2-methylpentyl and 2-methyl-2-
Examples include (3-methylphenyl) pentyl.

In the definition of Y ', phenyl C ₁ -C ₆ alkoxy which may be substituted with R ^c is benzyloxy, 2-chlorobenzyloxy, 3-bromobenzyl as linear or branched phenylalkoxy. Oxy, 4-chlorobenzyloxy, 4-methylbenzyloxy, 4-t-butylbenzyloxy, 2-methylbenzyloxy, 2-methoxybenzyloxy, 1-phenylethyloxy, 1- (3-chlorophenyl) ethyloxy, 2 -Phenylethyloxy, 1-methyl-1-phenylethyloxy, 1
-(4-chlorophenyl) -1-methylethyloxy, 1- (3-
Chlorophenyl) -1-methylethyloxy, 1-phenylpropyloxy, 2-phenylpropyloxy, 3-phenylpropyloxy, 1-phenylbutyloxy, 2-phenylbutyloxy, 3-phenylbutyloxy, 4-phenylbutyloxy , 1-methyl-1-phenylpropyloxy, 1
-Methyl-2-phenylpropyloxy, 1-methyl-3-phenylpropyloxy, 2-methyl-2-phenylpropyloxy, 2- (4-chlorophenyl) -2-methyl-propyloxy, 2-methyl-2- (3-methylphenyl) propyloxy, 1-phenylpentyloxy, 2-phenylpentyloxy, 3-phenylpentyloxy, 4-phenylpentyloxy, 5-phenylpentyloxy, 1-methyl-1-phenylbutyloxy, 1 -Methyl-2-phenylbutyloxy, 1-methyl-3-phenylbutyloxy, 1-methyl-4-phenylbutyloxy, 2-methyl-2-phenylbutyloxy, 2- (4-chlorophenyl) -2-methyl Butyloxy, 2
-Methyl-2- (3-methylphenyl) butyloxy, 1-phenylhexyloxy, 2-phenylhexyloxy, 3-phenylhexyloxy, 4-phenylhexyloxy, 5-
Phenylhexyloxy, 6-phenylhexyloxy,
1-methyl-1-phenylpentyloxy, 1-methyl-2-phenylpentyloxy, 1-methyl-3-phenylpentyloxy, 1-methyl-4-phenylpentyloxy, 2-methyl-
2-phenylpentyloxy, 2- (4-chlorophenyl) -2
Examples include-methylpentyloxy and 2-methyl-2- (3-methylphenyl) pentyloxy.

[0091] in Y ', optionally substituted by R may be substituted with ^c phenoxy and R ^c are defined in good phenoxycarbonyl, as a good phenoxy optionally substituted with R ^c is phenoxy, 2 -Fluorophenoxy, 3-Fluorophenoxy, 4-Fluorophenoxy, 2-Chlorophenoxy, 3-Chlorophenoxy, 4-Chlorophenoxy, 2-Bromophenoxy, 3-Bromophenoxy, 4-Bromophenoxy, 4-Iodophenoxy, 2 , 4-dichlorophenoxy, 3,4-dichlorophenoxy, 2,6-difluorophenoxy, 2,6-dichlorophenoxy, 2-fluoro-4-chlorophenoxy, 2,3,4,5,6-pentafluorophenoxy, 2-methylphenoxy, 3-methylphenoxy,
4-methylphenoxy, 2,5-dimethylphenoxy, 4-methyl-2,3,5,6-tetrafluorophenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-methoxyphenoxy, 2,6-dimethoxyphenoxy, Examples thereof include 3,4-dimethoxyphenoxy, 3,4,5-trimethoxyphenoxy, 2-trifluoromethylphenoxy, 3-trifluoromethylphenoxy and 4-trifluoromethylphenoxy.

[0092] in Y ', heteroaryl optionally substituted by R ^c, heteroaryl sulfonate optionally substituted with R ^c alkylsulfonyl, optionally substituted by R ^c heteroaryl sulfenyl, substituted with R ^c which may be heteroarylsulfonyl, optionally substituted by R good heteroarylcarbonyl optionally substituted with ^c and R ^c are defined in good heteroarylcarbonyloxy, optionally substituted by R ^c hetero As aryl, 2-fluorofuran-3-yl, 3-cyanopyrrol-1-yl, oxazol-2-yl, 2-methylsulphenyloxazol-4-yl, 2-methylsulfonyl-1,3,4- Oxadiazol-5-yl, 2-bromo-1,3,4-thiadiazole-5-
1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-1-yl, 1,2,3-
Triazol-1-yl, 1,2,3,4-tetrazol-1-yl,
6-methoxypyrimidin-2-yl, pyridazin-3-yl, 1,
3,5-triazin-2-yl, 1,2,4-triazin-6-yl, 1-
Methylpyrazol-5-yl, 1-methylpyrazol-4-yl, 1-methylpyrazol-3-yl, 1-phenylpyrazol-5-yl, 1-phenylpyrazol-4-yl, 1-phenylpyrazole-3- Yl, 1-methyl-4-fluoropyrazole-5
-Yl, 1-methyl-4-fluoropyrazol-3-yl, 1-methyl-3-fluoropyrazol-4-yl, 1-methyl-3-fluoropyrazol-5-yl, 1-methyl-5-fluoropyrazole -3-yl, 1-methyl-5-fluoropyrazol-4-yl, 1
-Methyl-4-chloropyrazol-5-yl, 1-methyl-4-chloropyrazol-3-yl, 1-methyl-3-chloropyrazole-4
-Yl, 1-methyl-3-chloropyrazol-5-yl, 1-methyl-5-chloropyrazol-3-yl, 1-methyl-5-chloropyrazol-4-yl, 1-methyl-3-bromopyrazole -4-yl, 1-methyl-3-phenylpyrazol-4-yl, 1-methyl
-5-nitropyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl, 1-methyl-3-difluorochloromethylpyrazol-4-yl, 1-methyl-3-trifluoromethyl- 5-methoxypyrazol-4-yl, 1-methyl-5-
Trifluoromethylpyrazol-3-yl, 1-methyl-4-methoxycarbonylpyrazol-5-yl, 1-methyl-4-methoxycarbonylpyrazol-3-yl, 1-methyl-5-methoxycarbonylpyrazol-3-yl , 1-methyl-3-chloro-4
-Methoxycarbonylpyrazol-5-yl, 1-methyl-3-
Chloro-4-ethoxycarbonylpyrazol-5-yl, 1-methyl-4-ethoxycarbonylpyrazol-3-yl, 1,4-dimethylpyrazol-5-yl, 1,4-dimethylpyrazole-3-
Yl, 1,3-dimethylpyrazol-4-yl, 1,3-dimethylpyrazol-5-yl, 1,5-dimethylpyrazol-3-yl,
1,5-dimethylpyrazol-4-yl, 1,5-dimethyl-4-chloropyrazol-3-yl, 1,3-dimethyl-5-chloropyrazol-4-yl, 1,3-dimethyl-5-fluoro Pyrazol-4-yl, 1,3-dimethyl-5-methoxypyrazol-4-yl, 1,3,
5-trimethylpyrazol-4-yl, 1,3-dimethyl-4-chloropyrazol-5-yl, 1,3-dimethyl-4-fluoropyrazol-5-yl, 1,3-dimethyl-4-nitropyrazole- 5-yl, 1,3-dimethyl-4-methoxypyrazol-5-yl, 1-methyl-3,5-dichloropyrazol-4-yl, 1-methyl-3,5-
Difluoropyrazol-4-yl, 1-phenyl-3,5-dichloropyrazol-4-yl, 1-phenyl-3,5-difluoropyrazol-4-yl, 1- (2-pyridyl) -3,5-dichloro Pyrazol-4-yl, 1-phenyl-5-methylpyrazol-4-yl, 1-phenyl-5-trifluoromethylpyrazol-4-yl, 1-phenyl-5-difluorochloromethylpyrazole-
4-yl, 1-t-butyl-5-methylpyrazol-4-yl, 1-methyl-3-chloro-5-methylthiopyrazol-4-yl, 1-methyl-pyrrol-2-yl, 1-methyl- Pyrrole-3-yl, 1-
Methyl-4-trifluoromethylpyrrol-5-yl, furan
-2-yl, furan-3-yl, 5-methylfuran-2-yl, 5-
Phenylfuran-2-yl, 2,5-dimethylfuran-3-yl,
2,4-dimethylfuran-3-yl, thiophen-2-yl, thiophen-3-yl, 5-phenylthiophen-2-yl, 5-methylthiophen-2-yl, 5-bromothiophen-2-yl, 3-
Bromothiophen-2-yl, 4,5-dibromothiophen-2-
Yl, 5-iodothiophen-2-yl, 5-chlorothiophen-2-yl, 5-phenyl-2-methylthiophen-3-yl, 5
-Nitrothiophen-3-yl, 3-methylthiophen-2-yl, 3-chlorothiophen-2-yl, 3-methoxythiophen-2-yl, 3-fluorothiophen-2-yl, thiazole
-4-yl, thiazol-5-yl, thiazol-2-yl, 2,4
-Dimethylthiazol-5-yl, 2-bromo-4-methylthiazol-5-yl, 2-chloro-4-methylthiazol-5-yl, 2-chloro-4-ethylthiazol-5-yl, 2-chloro -Four
-Trifluoromethylthiazol-5-yl, 2-methyl-4-
Trifluoromethylthiazol-5-yl, 2-methyl-4-ethylthiazol-5-yl, 2-bromo-4-ethylthiazole
-5-yl, 2-ethyl-4-methylthiazol-5-yl, 2-methoxy-4-methylthiazol-5-yl, 2-chloro-4-fluorothiazol-5-yl, 2-phenyl-4- Ethoxycarbonylthiazol-5-yl, 2-chlorothiazol-4-yl,
2-methylthiazol-4-yl, 1-phenyl-5-methyloxazol-4-yl, 1,3-dimethyloxazol-5-yl,
3-Methylisothiazol-5-yl, 3-benzyloxy-5-
Methylisothiazol-4-yl, 4-chloro-5-ethoxycarbonylisothiazol-3-yl, isoxazole-5-
Yl, 3,5-dimethylisoxazol-4-yl, 5-methylisoxazol-3-yl, 3-phenyl-5-methylisoxazol-4-yl, 4-cyanoisoxazol-3-yl, 1- Methylimidazol-5-yl, 1-methyl-4,5-dichloroimidazol-2-yl, 1,5-dimethyl-2-chloroimidazol-4-yl, 1-phenyl-5-methyl-1,2,3 -Triazol-4-yl, 1-phenyl-5-ethyl-1,2,3-triazol-4-yl, 1-phenyl-5-dibromomethyl-1,2,3-triazol-4-yl, 4- Methyl-1,2,3-thiadiazole-5
-Yl, 4-ethyl-1,2,3-thiadiazol-5-yl, 1,2,3
-Thiadiazol-5-yl, 1,2,3-thiadiazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-
Yl, 6-methylpyridin-3-yl, 6-chloropyridin-2-
Yl, 6-phenoxypyridin-2-yl, 2-chloropyridin-4-yl, 2-fluoropyridin-4-yl, 2,6-dichloropyridin-4-yl, 2-methoxypyridin-4-yl, 3 , 6-Dichloropyridin-2-yl, 2-chloro-6-methylpyridine-4
-Yl, 3-fluoropyridin-2-yl, 3-fluoropyridin-4-yl, quinoxalin-2-yl, 6-chloroquinoxalin-2-yl, 6-fluoroquinoxalin-2-yl, 6 -Methoxyquinoxalin-2-yl, 5-chloroquinoxalin-2-yl, 5-fluoroquinoxalin-2-yl, 5-methoxyquinoxalin-2-yl, 1-methylindole-3- 1-methyl-2-chloroindol-3-yl, 1-methyl-2-fluoroindol-3-yl, benzothiazol-2-yl, 5-fluorobenzothiazol-2-yl, 6-fluorobenzothiazole -2-yl, quinolin-4-yl, pyrazin-2-yl, 3
-Chloropyrazin-2-yl, 3-methylpyrazin-2-yl, 3
-Ethylpyrazin-2-yl, 2-phenyl-4-methylpyrimidin-5-yl, 2,4-dimethylpyrimidin-5-yl, 4-trifluoromethylpyrimidin-5-yl, 4-difluorochloromethylpyrimidin- 5-yl, 4-pentafluoroethylpyrimidin-5-yl, 4-methylthiopyrimidin-5-yl,
4-Bromodifluoromethylpyrimidin-5-yl and 2-
Methyl-4-chlorodifluoromethylpyrimidin-5-yl and the like can be mentioned.

The heteroaryl C ₁ -C ₆ alkoxy which may be substituted with R ^c in the definition of Y'is pyridin-2-ylmethyloxy, 5-chlorothiophene as a linear or branched heteroarylalkoxy. -2-ylmethyloxy, 1-methyl-3-chloropyrazol-5-ylmethyloxy, 2- (3-methylfuran-2-yl) ethyloxy, 3- (6-trifluoromethylpyridin-2-yl) Propyloxy, 4- (pyrimidin-2-yl) butyloxy, 5
Examples include- (triazol-1-yl) pentyloxy and 6- (pyrrol-1-yl) hexyloxy.

[0094] in Y ', R ^c substituted by heteroaryl C ₁ optionally -C ₆ alkyl, is heteroaryl C ₁ optionally -C ₆ alkylsulfenyl-substituted with R ^c, is substituted with R ^c Optionally heteroaryl C ₁ -C
₆ alkylsulfinyl, heteroaryl optionally substituted by R ^c C ₁ -C ₆ alkylsulfonyl, optionally substituted by R ^c in an optionally substituted heteroaryl C ₁ -C ₆ alkylcarbonyl and R ^c R defined as a good heteroaryl C ₁ -C ₆ alkylcarbonyloxy
^Examples of the heteroaryl C ₁ -C ₆ alkyl which may be substituted with ^c include pyridin-2-ylmethyl, 5-chlorothiophen-2-ylmethyl, 1-methyl-3-, as linear or branched heteroarylalkyl. Chloropyrazol-5-ylmethyl, 2- (3-methylfuran-2-yl) ethyl, 3- (6
-Trifluoromethylpyridin-2-yl) propyl, 4-
(Pyrimidin-2-yl) butyl, 5- (triazol-1-yl) pentyl, 6- (pyrrol-1-yl) hexyl and the like can be mentioned.

In [0095] Y ', as defined in R ^c in optionally substituted heteroaryloxy and optionally substituted by R ^c heteroaryloxycarbonyl, R
Examples of the heteroaryloxy which may be substituted with ^c include 5-chlorothiophen-2-yloxy, 3,5-dimethylfuran-2-yloxy, 3-cyano-1-methylpyrrol-1-
Iloxy, oxazol-2-yloxy, 2-methylsulphenyloxazol-4-yloxy, 4-methylthiazol-2-yloxy, 2-trifluoromethylimidazol-4-yloxy, isoxazol-3-yloxy, 3-
Chloroisoxazol-4-yloxy, 3-methylisothiazol-5-yloxy, 1-benzyl-3-phenylpyrazol-5-yloxy, 1-methylpyrazol-5-yloxy, 2-methylsulfonyl-1,3, 4-oxadiazol-5-yloxy, 2-bromo-1,3,4-thiadiazol-5-yloxy, 1,2,4-oxadiazol-3-yloxy, 1,2,4-thiadiazole-5- Iloxy, 1,2,4-triazol-3-yloxy, 1,2,3-thiadiazol-5-yloxy, 1,2,3
-Triazol-5-yloxy, 1,2,3,4-tetrazole-5
-Yloxy, 6-phenoxypyridin-2-yloxy, 6-
Methoxypyrimidin-2-yloxy, pyrazin-2-yloxy, pyridazin-3-yloxy, 1,3,5-triazine-2-
Iloxy, 1,2,4-triazin-6-yloxy and the like can be mentioned.

Naphthyl in the definition of Y'is 1
Examples include-naphthyl and 2-naphthyl.

[0097] R ^c and Y may be substituted in R ^b in 'C ₁ -C ₆ alkylsulfenyl, optionally substituted with R ^b C ₁ -C ₆ alkylsulfinyl, substituted by R ^b Optionally C ₁ -C ₆ alkylsulfonyl, R
optionally substituted with ^b be substituted also a good C ₁ -C ₆ alkylcarbonyl and R ^b is also defined a good C ₁ -C ₆ alkylcarbonyloxy, optionally substituted with R ^b C ₁ ~ Examples of C ₆ alkyl include linear, branched alkyl such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, s-butyl, n-pentyl, n-hexyl, 2-ethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl- 2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-
Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, fluoromethyl, chloromethyl , Bromomethyl, iodomethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 1-bromoethyl, 1-iodoethyl, 1-fluoroethyl, 2-chloroethyl, 2-bromoethyl , 2-iodoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-
Trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2,2,2-trifluoro-1-chloroethyl, 3-fluoropropyl, 3-chloropropyl, 1-fluoro-i-propyl, 1- Chloro-i-propyl, heptafluoropropyl, 1,1,2,2,3,3-hexafluoropropyl, 4-chlorobutyl, 4-fluorobutyl, 5-chloropentyl, 5-
Fluoropentyl, 6-chlorohexyl, 6-fluorohexyl, methoxymethyl, ethoxymethyl, n-propoxymethyl, i-propoxymethyl, n-butoxymethyl, i-butoxymethyl, s-butoxymethyl, t-butoxymethyl,
n-pentyloxymethyl, 2-methoxyethyl, 3-ethoxypropyl, 3-methoxypropyl, methylthiomethyl,
Ethylthiomethyl, n-propylthiomethyl, i-propylthiomethyl, n-butylthiomethyl, i-butylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, n-pentylthiomethyl, 2-methylthioethyl , 3-ethylthiopropyl, 3-methylthiopropyl, benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-t-butylbenzyl, 2-methylbenzyl,
2-methoxybenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1- (4-chlorophenyl) -1-methylethyl, 1- (3 -Chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1- Phenylpropyl, 1-methyl-2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4-
Chlorophenyl) -2-methylpropyl, 2-methyl-2- (3-
Methylphenyl) propyl, 1-phenylpentyl, 2-phenylpentyl, 3-phenylpentyl, 4-phenylpentyl, 5-phenylpentyl, 1-methyl-1-phenylbutyl, 1-methyl-2-phenylbutyl, 1- Methyl-3-phenylbutyl, 1-methyl-4-phenylbutyl, 2-methyl-2-phenylbutyl, 2- (4-chlorophenyl) -2-methylbutyl, 2-methyl-2- (3-methylphenyl) butyl , 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenylhexyl, 1-methyl-1-phenylpentyl, 1-methyl-2-phenylpentyl, 1 -Methyl-3-phenylpentyl, 1-methyl-4-phenylpentyl, 2-methyl-2-phenylpentyl, 2- (4-chlorophenyl) -2-methylpentyl, 2-methyl-2- (3-methylphenyl ) Pentyl, pyridin-2-yl Methyl, 5-chlorothiophen-2-ylmethyl, 1-methyl-3-chloropyrazol-5-ylmethyl, 2-
(3-Methylfuran-2-yl) ethyl, 3- (6-trifluoromethylpyridin-2-yl) propyl, 4- (pyrimidine-
2-yl) butyl, 5- (triazol-1-yl) pentyl, 6- (pyrrol-1-yl) hexyl and the like can be mentioned.

[0098] R ^c and may be substituted by R ^b in Y 'C ₂ ~C ₆ alkenyloxy, optionally substituted by R ^b C ₂ -C ₆ alkenyl Le phenyl, substituted by R ^b also defined a good C ₂ -C ₆ alkenylsulfonyl optionally substituted with even better C ₂ -C ₆ alkenylsulfinyl and R ^b are, optionally substituted with R ^b C ₂
~ C ₆ alkenyl includes ethenyl, 1-propenyl, 2-propenyl, 1-alkenyl as straight chain or branched alkenyl.
Butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-
Pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1- Dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1- Methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-
Butenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-
Butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-
Butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-
Butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-
Butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-
Ethyl-3-butenyl, 1-methyl-2-pentenyl, 2-methyl
-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-
Pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,
3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1,
2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 2-chloroethenyl, 2-bromoethenyl, 2,2-
Dichloroethenyl, 3-chloro-2-propenyl, 3-fluoro-2-propenyl, 3-bromo-2-propenyl, 3-iodo-2
-Propenyl, 3,3-dichloro-2-propenyl, 3,3-difluoro-2-propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3-butenyl and 4,4-difluoro-3-butenyl Etc.

[0099] R ^c and may be substituted by R ^b in Y 'C ₂ ~C ₆ alkynyloxy, optionally substituted by R ^b C ₂ -C ₆ alkyl Nils Le phenyl, substituted by R ^b which may be C ₂ -C ₆ alkynylsulfinyl,
And optionally substituted with R ^b as defined in good C ₂ -C ₆ alkynylsulfonyl, as good C ₂ -C ₆ alkynyl optionally substituted with R ^b, ethynyl as linear or branched alkynyl, 1-propynyl, 2-propynyl,
1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl,
1-methyl-1-ethyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-butynyl, 1-methyl-3-
Butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-pentynyl, 1- Methyl-4-pentynyl,
2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, hexynyl, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl , 3-bromo-2-propynyl,
3-iodo-2-propynyl, 4-bromo-3-butynyl, 4-iodo-3-butynyl, 6-iodo-5-hexynyl and the like can be mentioned.

R ^c and Y ′ defined as C ₁ -C ₆ alkoxycarbonyl optionally substituted by R ^b .
The C ₁ -C ₆ alkoxy which may be substituted with R ^b includes linear or branched alkoxy such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and i-.
Butoxy, s-butoxy, t-butoxy, n-pentyloxy, n-hexyloxy, 1,1-dimethylpropoxy, 1,2-
Dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1
-Ethyl-2-methylpropoxy 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylbutoxy, 2-
Ethyl butoxy, 1,1-dimethyl butoxy, 1,2-dimethyl butoxy, 1.3-dimethyl butoxy, 2,2-dimethyl butoxy, 2,3-dimethyl butoxy, 3,3-dimethyl butoxy, 1-
Methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, dichloromethoxy, trichloromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy , Bromodifluoromethoxy, dichlorofluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-iodoethoxy, 1-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2-fluoroethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2,2,2-trifluoro-1-chloroethoxy, 1,1,2,2 -Tetrafluoroethoxy, 3-bromopropoxy, 1-fluoro-i-propoxy, 1-chloro B-i-propoxy, 3-fluoropropoxy, 3-chloropropoxy, heptafluoropropoxy, 1,1,2,2,3,3-hexafluoropropoxy, 4-chlorobutoxy, 4-fluorobutoxy,
5-chloropentyloxy, 5-fluoropentyloxy,
6-chlorohexyloxy, 6-fluorohexyloxy,
Benzyloxy, 2-chlorobenzyloxy, 3-bromobenzyloxy, 4-chlorobenzyloxy, 4-methylbenzyloxy, 4-t-butylbenzyloxy, 2-methylbenzyloxy, 2-methoxybenzyloxy, 1-phenyl Ethyloxy, 1- (3-chlorophenyl) ethyloxy,
2-phenylethyloxy, 1-methyl-1-phenylethyloxy, 1- (4-chlorophenyl) -1-methylethyloxy, 1- (3-chlorophenyl) -1-methylethyloxy, 1
-Phenylpropyloxy, 2-phenylpropyloxy, 3-phenylpropyloxy, 1-phenylbutyloxy, 2-phenylbutyloxy, 3-phenylbutyloxy, 4-phenylbutyloxy, 1-methyl-1-phenylpropyloxy , 1-methyl-2-phenylpropyloxy, 1
-Methyl-3-phenylpropyloxy, 2-methyl-2-phenylpropyloxy, 2- (4-chlorophenyl) -2-methylpropyloxy, 2-methyl-2- (3-methylphenyl)
Propyloxy, 1-phenylpentyloxy, 2-phenylpentyloxy, 3-phenylpentyloxy, 4-phenylpentyloxy, 5-phenylpentyloxy, 1-methyl-1-phenylbutyloxy, 1-methyl-2-phenyl Butyloxy, 1-methyl-3-phenylbutyloxy, 1-methyl-4-phenylbutyloxy, 2-methyl-2-phenylbutyloxy, 2- (4-chlorophenyl) -2-methylbutyloxy, 2-methyl -2- (3-methylphenyl) butyloxy, 1-phenylhexyloxy, 2-phenylhexyloxy, 3-phenylhexyloxy, 4-phenylhexyloxy, 5-phenylhexyloxy, 6-phenylhexyloxy, 1-methyl -1-phenylpentyloxy, 1-methyl-2-phenylpentyloxy, 1-methyl-3-phenylpentyloxy, 1-methyl-4-phenylpentyloxy , 2-methyl-2-phenyl-pentyloxy, 2- (4-chlorophenyl) -2-methyl-pentyloxy, 2-methyl-2-
(3-methylphenyl) pentyloxy, pyridin-2-ylmethyloxy, 5-chlorothiophen-2-ylmethyloxy, 1-methyl-3-chloropyrazol-5-ylmethyloxy, 2- (3-methylfuran -2-yl) ethyloxy, 3- (6
-Trifluoromethylpyridin-2-yl) propyloxy, 4- (pyrimidin-2-yl) butyloxy, 5- (1,2,4
Examples include -triazol-1-yl) pentyloxy and 6- (pyrrol-1-yl) hexyloxy.

C ₁ -C ₁₂ alkyl optionally substituted by R ^b in the definition of R ^c and Y ′ is methyl, ethyl, n-propyl, i-propyl, n as linear or branched alkyl. -Butyl, i-butyl, t-butyl, s-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decanyl, 2-ethylpropyl, 2,2-dimethylpropyl , 1,2-dimethylpropyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1
-Methylpropyl, 1-ethyl-2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2- Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,
4-methylpentyl, 2-ethylhexyl, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 1-bromoethyl, 1-
Iodoethyl, 1-fluoroethyl, 2-chloroethyl, 2-
Bromoethyl, 2-iodoethyl, 2-fluoroethyl, 2,
2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,
2-trichloroethyl, pentafluoroethyl, 2,2,2-trifluoro-1-chloroethyl, 3-fluoropropyl, 3-
Chloropropyl, 1-fluoro-i-propyl, 1-chloro-i-
Propyl, heptafluoropropyl, 1,1,2,2,3,3-hexafluoropropyl, 4-chlorobutyl, 4-fluorobutyl, 5-chloropentyl, 5-fluoropentyl, 6-chlorohexyl, 6-fluorohexyl , 7-fluoroheptyl,
8-chlorooctyl, methoxymethyl, ethoxymethyl,
n-propoxymethyl, i-propoxymethyl, n-butoxymethyl, i-butoxymethyl, s-butoxymethyl, t-butoxymethyl, n-pentyloxymethyl, 2-methoxyethyl, 3-ethoxypropyl, 3-methoxypropyl , Methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, i-propylthiomethyl, n-butylthiomethyl, i-butylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, n-pentylthiomethyl, 2-methylthioethyl, 3-
Ethylthiopropyl, 3-methylthiopropyl, benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-t-butylbenzyl, 2-methylbenzyl, 2-methoxybenzyl, 1- Phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1- (4-chlorophenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-methyl Ethyl, 1-phenylpropyl, 2-phenylpropyl,
3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl
-1-phenylpropyl, 1-methyl-2-phenylpropyl,
1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4-chlorophenyl) -2-methylpropyl, 2
-Methyl-2- (3-methylphenyl) propyl, 1-phenylpentyl, 2-phenylpentyl, 3-phenylpentyl,
4-phenylpentyl, 5-phenylpentyl, 1-methyl-1
-Phenylbutyl, 1-methyl-2-phenylbutyl, 1-methyl-3-phenylbutyl, 1-methyl-4-phenylbutyl, 2-
Methyl-2-phenylbutyl, 2- (4-chlorophenyl) -2-
Methylbutyl, 2-methyl-2- (3-methylphenyl) butyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenylhexyl, 1-methyl- 1-phenylpentyl, 1-methyl-2-phenylpentyl, 1-methyl-3-phenylpentyl, 1-methyl-4-phenylpentyl, 2-methyl-
2-phenylpentyl, 2- (4-chlorophenyl) -2-methylpentyl, 2-methyl-2- (3-methylphenyl) pentyl, pyridin-2-ylmethyl, 5-chlorothiophen-2-ylmethyl, 1-methyl -3-chloropyrazol-5-ylmethyl, 2- (3-methylfuran-2-yl) ethyl, 3- (6-trifluoromethylpyridin-2-yl) propyl, 4- (pyrimidin-2-yl) butyl , 5- (1,2,4-triazol-1-yl) pentyl, 6- (pyrrol-1-yl) hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 2,2-dichlorocyclopropyl Methyl, 1-phenylpyrazole-5-carboxymethyl, tetrahydropyran-2-ylmethyl, imidazol-1-ylmethyl, 2-difluoromethoxyethyl, 2-
Methylsulfenylethyl, 3-cyanopropyl, 2-formyl-2-methylpropyl, 4-methoxycarbonyl-4-cyanobutyl, 5- (2-chlorophenyl) pentyl, 1-phenyl-1-methoxymethyl, 1-phenyl- 1-ethoxymethyl,
1- (2-chlorophenyl) -1-methoxymethyl, 1- (3-chlorophenyl) -1-methoxymethyl, 1- (4-chlorophenyl) -1-methoxymethyl, 1- (2-fluorophenyl)-
1-methoxymethyl, 1- (3-fluorophenyl) -1-methoxymethyl, 1- (4-fluorophenyl) -1-methoxymethyl, 1- (2-methylphenyl) -1-methoxymethyl, 1-
(3-Methylphenyl) -1-methoxymethyl, 1- (4-methylphenyl) -1-methoxymethyl, 1-phenyl-1-chloromethyl, 1-phenyl-1,1-dimethoxymethyl and 6-morpholinohexyl Etc.

C ₁ -C ₁₂ alkenyl which may be substituted by R ^b in the definition of R ^c and Y'is ethenyl, 1-propenyl, 2-propenyl, 1-butenyl as a straight chain or branched alkenyl. , 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 6-heptenyl, 7 -Octenyl, 8-nonenyl, 9-decenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl -2-propenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,
3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl
-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-
Butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-
Butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-
Butenyl, 1,3-dimethyl-3-butenyl, 2,3-dimethyl-2-
Butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-
Butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl
-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-
Pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,
4-methyl-4-pentenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl, 3-chloro -2-propenyl, 3-fluoro-2-propenyl, 3-bromo
-2-propenyl, 3-iodo-2-propenyl, 3,3-dichloro
-2-propenyl, 3,3-difluoro-2-propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4-difluoro-3-butenyl 2-phenylethenyl, 3- Cyano-2-propenyl, 4- (4-chlorophenyl) -4-ethoxycarbonyl-3-butenyl, 3- (thiazole-2-carbonyloxy)
-4-methoxy-3-butenyl, 2-phenylethenyl, 2- (4-
Chlorophenyl) ethenyl, 2- (3-chlorophenyl) ethenyl, 2- (2-chlorophenyl) ethenyl, 2- (4-fluorophenyl) ethenyl, 2- (3-fluorophenyl) ethenyl, 2- (2-fluorophenyl) Ethenyl, 2- (4-methylphenyl) ethenyl, 2- (3-methylphenyl) ethenyl, 2- (2-methylphenyl) ethenyl, 2-phenyl-
1,2-dibromoethenyl and 6- (pyrazol-1-yl)-
3-hexenyl and the like can be mentioned.

C ₁ -C ₁₂ alkynyl optionally substituted by R ^b in the definition of R ^c and Y'is ethynyl, 1-propynyl, 2-propynyl, 1-methyl as straight chain or branched alkynyl. -2-propynyl, 1,1-dimethyl-2-propynyl, 1-methyl-1-ethyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2
-Butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2 , 2-Dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -Methyl-3-pentynyl, 1-
Methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2
-Pentynyl, hexynyl, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl, 3-
Bromo-2-propynyl, 3-iodo-2-propynyl, 4-bromo-3-butynyl, 4-iodo-3-butynyl, 6-iodo-5-hexynyl, 4- (2-chlorothiazol-5-yl) -3-butynyl, 5-formyl-3-pentynyl, 6-methylsulfenyl-
5-hexynyl, 2-phenylethynyl and 3-cyano-5-
Hexynyl and the like can be mentioned.

C ₁ -C ₁₂ alkoxy which may be substituted by R ^b in the definition of R ^c and Y ′ is methoxy, ethoxy, n-, which may be linear or branched alkoxy.
Propoxy, i-propoxy, n-butoxy, i-butoxy,
s-Butoxy, t-butoxy, n-pentyloxy, n-hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1,2- Trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2-
Methylpropoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1.3-dimethylbutoxy, 2,2 -Dimethyl butoxy, 2,
3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decanyloxy, fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, dichloromethoxy, trichloromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, 1-chloroethoxy,
1-bromoethoxy, 1-iodoethoxy, 1-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro Ethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2,2,2-trifluoro
-1-chloroethoxy, 1,1,2,2-tetrafluoroethoxy, 3-bromopropoxy, 1-fluoro-i-propoxy, 1
-Chloro-i-propoxy, 3-fluoropropoxy, 3-chloropropoxy, heptafluoropropoxy, 1,1,2,2,3,
3-hexafluoropropoxy, 4-chlorobutoxy, 4-fluorobutoxy, 5-chloropentyloxy, 5-fluoropentyloxy, 6-chlorohexyloxy, 6-fluorohexyloxy, benzyloxy, 2-chlorobenzyloxy, 3 -Bromobenzyloxy, 4-chlorobenzyloxy, 4-methylbenzyloxy, 4-t-butylbenzyloxy, 2-methylbenzyloxy, 2-methoxybenzyloxy, 1-phenylethyloxy, 1- (3-chlorophenyl) Ethyloxy, 2-phenylethyloxy, 1-methyl
-1-Phenylethyloxy, 1- (4-chlorophenyl) -1-
Methylethyloxy, 1- (3-chlorophenyl) -1-methylethyloxy, 1-phenylpropyloxy, 2-phenylpropyloxy, 3-phenylpropyloxy, 1-phenylbutyloxy, 2-phenylbutyloxy, 3- Phenylbutyloxy, 4-phenylbutyloxy, 1-methyl-1
-Phenylpropyloxy, 1-methyl-2-phenylpropyloxy, 1-methyl-3-phenylpropyloxy, 2-methyl-2-phenylpropyloxy, 2- (4-chlorophenyl) -2-methylpropyloxy, 2 -Methyl-2- (3-methylphenyl) propyloxy, 1-phenylpentyloxy, 2-phenylpentyloxy, 3-phenylpentyloxy, 4-phenylpentyloxy, 5-phenylpentyloxy, 1-methyl-1- Phenylbutyloxy, 1-methyl-
2-phenylbutyloxy, 1-methyl-3-phenylbutyloxy, 1-methyl-4-phenylbutyloxy, 2-methyl-
2-phenylbutyloxy, 2- (4-chlorophenyl) -2-
Methylbutyloxy, 2-methyl-2- (3-methylphenyl) butyloxy, 1-phenylhexyloxy, 2-phenylhexyloxy, 3-phenylhexyloxy, 4-phenylhexyloxy, 5-phenylhexyloxy, 6-
Phenylhexyloxy, 1-methyl-1-phenylpentyloxy, 1-methyl-2-phenylpentyloxy, 1-methyl-3-phenylpentyloxy, 1-methyl-4-phenylpentyloxy, 2-methyl-2- Phenylpentyloxy, 2- (4-chlorophenyl) -2-methylpentyloxy, 2-methyl-2- (3-methylphenyl) pentyloxy, pyridin-2-ylmethyloxy, 5-chlorothiophen-2-ylmethyl Oxy, 1-methyl-3-chloropyrazole
-5-ylmethyloxy, 2- (3-methylfuran-2-yl) ethyloxy, 3- (6-trifluoromethylpyridin-2-yl) propyloxy, 4- (pyrimidin-2-yl) butyloxy, 5 -(Triazol-1-yl) pentyloxy, 6-
(Pyrrol-1-yl) hexyloxy, 1-phenylpyrazole-5-carboxymethyloxy, tetrahydropyran-2-ylmethyloxy, imidazol-1-ylmethyloxy, 2-difluoromethoxyethyloxy, 2-methylsulfenyl Ethyloxy, 3-cyanopropyloxy, 2-
Formyl-2-methylpropyloxy, 4-methoxycarbonyl-4-cyanobutyloxy, 5- (2-chlorophenyl)
Examples include pentyloxy and 6-morpholinohexyloxy.

[0105] As the R ^c and Y is C ₁ optionally -C ₆ alkoxy C ₁ -C ₆ alkoxy substituted with R ^b in the definition of ', methoxymethoxy, ethoxymethoxy, n- propoxy methoxy, i- propoxy methoxy , N-butoxymethoxy, i-butoxymethoxy, s-butoxymethoxy,
t-butoxymethoxy, n-pentyloxymethoxy, 2-methoxyethoxy, 3-ethoxypropoxy, 3-methoxypropoxy, cyanomethoxymethoxy, 2- (2-nitroethoxy) ethoxy, 3- (1-methylpyrazole-5- Ilmethoxy) propyloxy, 4- (3-cyano-2-methylpropyloxy) butoxy, 5-benzyloxypentyloxy and 5- (2-trifluoromethylthiazol-5-yl)
Methoxyhexyloxy and the like can be mentioned.

In the definition of Y, a 3- to 7-membered ring optionally containing 1 to 3 oxygen atoms, nitrogen atoms or sulfur atoms together with the carbon atoms by 2 Y substituted on the same carbon as A ^1. Examples thereof include cyclopropyl, 2,2-dichlorocyclopropyl, cyclobutyl, oxetane, cyclopentyl and the like.

[0107] in the definition of R ² and R ^3, the R ² and R ³ and the oxygen atom may together from 1 selected from nitrogen atom or a sulfur atom include a 4 heteroatoms 3 The 7-membered ring includes aziridine, morpholine,
Hexamethyleneimine, 4-benzylpiperazine and the like can be mentioned.

[0108] in the definition of U ¹ and U ^2, and the U ¹ and U ² together form an oxygen atom, also from 1 selected from nitrogen atom or a sulfur atom include a 4 heteroatoms Suitable 3- to 7-membered rings include aziridine, morpholine, hexamethyleneimine, 4-benzylpiperazine and the like.

[0109] As A ¹ is include 5-membered ring heterocycles and 6 membered heterocyclic ring such as Preferred A ¹ are, for example,

[0110]

[Chemical 17]

[0111]

[Chemical 18]

And more preferable A ^{1 is} as follows.
For example,

[0113]

[Chemical 19]

And particularly preferable A ^{1 is} as follows.
For example,

[0115]

[Chemical 20]

And the like. Note that Y, Ya, d, e,
f, g, h, i, j and k have the same meanings as described above.

Examples of A ² include A ² a to A ² y.

As B, for example, --CH _2- , --C
(= CH-OR ⁴⁾ - or -C (N = OR ⁴⁾ - and the like.

R ¹ is preferably, for example, hydrogen atom, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, n-pentyl, 3-methylbutyl, n-. Examples include hexyl and benzyl, and more preferable examples include methyl.

R ² is preferably, for example, hydrogen atom, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, n-pentyl, 3-methylbutyl, n-. Examples include hexyl and benzyl, and more preferable examples include methyl.

[0121] As R ³ is preferably, for example, a hydrogen atom, methyl, ethyl, good and benzyl optionally substituted by phenyl which may be substituted and R ^a in R ^a can be mentioned, more preferably, Examples thereof include a hydrogen atom, phenyl which may be substituted with ^Ra , and methyl.

R ⁴ includes, for example, a hydrogen atom, methyl, ethyl, benzyl and the like, and more preferably, methyl is mentioned.

Examples of R ⁵ include a hydrogen atom, methyl, acetyl, phenyl and benzyl,
More preferably, for example, methyl, acetyl and the like can be mentioned.

Examples of R ⁶ include a hydrogen atom, a chlorine atom, methyl, ethyl, methoxycarbonyl, methylsulfenyl, phenyl optionally substituted with R ^a and benzyl.

[0125] As R ⁷ is, for example, phenyl optionally substituted by R ^a, R ^a with optionally substituted heteroaryl, hydrogen, methyl, ethyl, methoxy, benzyloxy, acetyl and R ^a Examples thereof include optionally substituted benzyl and the like.

Examples of R ⁸ and R ⁹ include hydrogen atom, chlorine atom, methyl, ethyl and benzyl.

Examples of R ¹⁰ include hydrogen atom, chlorine atom, methyl and methoxy.

Examples of R ¹¹ include a hydrogen atom, methyl and ethyl.

Examples of R ¹² include a hydrogen atom and methyl.

Examples of R ¹³ include hydrogen atom, chlorine atom, bromine atom, methyl and methoxy.

R ^a is preferably, for example, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C
_{1 ~C 6} haloalkyl, C _{1 ~C 6} haloalkoxy, CN,
Examples thereof include nitro and C ₁ -C ₆ alkoxycarbonyl and the like, and more preferable examples include Cl, F, Br, trifluoromethyl, methoxy, ethoxy, ethyl, propyl and methyl.

[0132] As R ^b are preferably, for example, a halogen atom, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylsulfenyl, optionally substituted with R ^a phenyl, optionally substituted with R ^a And heteroaryl, CN, nitro, C ₁ -C ₆ alkoxycarbonyl and the like.

[0133] As R ^c, preferably, for example, a halogen atom, phenyl optionally substituted with R ^a, which may be substituted by R ^a heteroaryl, phenyl carbonyl optionally substituted with R ^a , phenyl sulfonyl optionally substituted by R ^a, which may be substituted by R ^b C ₁ ~C ₆ alkyl, optionally substituted with R ^b C ₂
To C ₆ alkenyl, C _{2 to} C ₆ optionally substituted with R ^b
Alkynyl, R ^b substituted by C ₁ optionally -C ₆ alkoxy, R ^b substituted by C ₁ optionally -C ₆ alkylsulfenyl, CN, nitro, OH, SH, SCN and C ₁ -C ₆ alkoxycarbonyl and the like can be mentioned.

X ¹ is preferably, for example, a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C _1.
1 -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy, CN,
Nitro, SR, NU ¹ U ² , phenylcarbonyl which may be substituted with ^Ra , C ₁ -C ₄ alkoxycarbonyl and the like can be mentioned, more preferably, for example, Cl,
F, I, Br, methoxy, ethyl, n-propyl, ethoxy, n-propoxy, chlorodifluoromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, pentafluoroethyl, ethoxycarbonyl, CN, acetyl and methyl Is mentioned.

X ² is preferably, for example, C _1-
Examples thereof include C ₄ alkyl and phenyl optionally substituted with R ^a , and more preferable examples include methyl and phenyl.

X ³ is preferably, for example, a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C
₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy, CN,
Nitro, SR, NU ¹ U ² , phenylcarbonyl which may be substituted with ^Ra , C ₁ -C ₄ alkoxycarbonyl and the like can be mentioned, more preferably, for example, Cl,
F, I, Br, methoxy, ethyl, n-propyl, ethoxy, n-propoxy, chlorodifluoromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, pentafluoroethyl, ethoxycarbonyl, CN, acetyl and methyl Is mentioned.

X ⁴ is preferably, for example, a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C
₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy, CN,
Nitro, SR, NU ¹ U ² , phenylcarbonyl which may be substituted with ^Ra , C ₁ -C ₄ alkoxycarbonyl and the like can be mentioned, more preferably, for example, Cl,
F, I, Br, methoxy, ethyl, n-propyl, ethoxy, n-propoxy, chlorodifluoromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, pentafluoroethyl, ethoxycarbonyl, CN, acetyl and methyl Is mentioned.

Y ′ is preferably, for example, a hydrogen atom, a halogen atom, or C ₁ -which may be substituted with R ^b.
C ₆ alkyl, C ₁ -C ₆ alkoxy optionally substituted with R ^b , phenyl optionally substituted with R ^c , phenoxy optionally substituted with R ^c , optionally substituted with R ^c Good phenyl C ₁ -C ₆ alkyl, heteroaryl optionally substituted with R ^c , CN, nitro and C ₁ -C ₆
Alkoxycarbonyl etc. are mentioned.

U ¹ and U ² are preferably, for example, hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₂ haloalkyl, phenyl, heteroaryl, C ₁ -C ₄ alkylcarbonyl and C ₁ -C. ₄ alkoxycarbonyl and the like, more preferably, for example, H, methyl, phenyl,
Benzyl, acetyl, methoxycarbonyl are mentioned.

D is preferably, for example, a single bond, -C (= Q ² )-and -C (R ⁶ ) = N-O-.

Z is -OR ¹ , -SR ¹ and -N
R ² R ³ and the like.

As Q ¹ , Q ² and Q ^3, it is preferable that
O, a = S, = N-R ⁷ and = CH _2.

As Q ⁴ and Q ⁵ , ═O is preferable.
And = S.

As G, for example, G ¹ , G ² , G ³ ,
G ⁴ , G ⁵ , G ⁶ , G ⁷ and G ⁸ are mentioned, preferably, for example, G ¹ , G ² , G ³ and G ⁴ , and more preferably G ¹ .

N is preferably 0, 1 or 2.

P is preferably 0 or 1.

Further, as the pesticidally acceptable salt of the heterocyclic imino aromatic compound of the present invention, for example, hydrochloride, hydrobromide, hydroiodide, formate, acetate,
Examples thereof include ammonium salt, isopropylamine salt, oxalate salt and the like.

The compounds of the present invention are preferably those in which the imino bond does not change due to tautomerism.

Next, as a plant disease to be controlled by the compound of the present invention, rice blast (Pyricularia) is used.
a oryzae), sesame leaf blight (Cochliobo)
lms myabeanus), blight (Rhizo)
ctonia solani), powdery mildew of wheat (Erysiphe graminis f. sp. h.
ordei, f. sp. tritici), leaf spot disease (P
yrenophora graminea), net blotch (Pyrenophora teres), red mold (Gibberella zeae), rust (Puc)
cina striformis, P. grami
nis, P.N. recondita, P. holde
i), snow rot (Tipula sp., Microne)
ctria nivalis), naked smut (Ustil
ago tritici, U.S.S. nuda), eye spot (Pseudocercosporella her
potrichoides), cloud disease (Rhyncho)
sporium secalis), leaf blight (Sept)
oria tritici), wilt disease (Leptosp)
haeria nodorum), citrus black spot (Diaportthe citri), and scab (El)
sinoe fawcetti), fruit rot (Pen
icillium digitalum, P. ital
Icum), Monili disease of apple (Sclerotin
ia mali), rot (Valsa mal)
i), powdery mildew (Podosphaera lcuc)
hotricha), leaf spot disease (Alternari)
a mali), scab (Venturia inae)
qualis), pear scab (Venturian)
Ashicola), Black spot (Alternaria)
kikuchuiana), red scab (Gymnospor)
Angium haraenum), Peach scab (S
clerotinia cinerea), scab (C
ladosporium carpophilum),
Phomopsis sp.,
Downy mildew of grape (Plasmopara vitico
la), black scab (Elsinoe ampelin)
a), late rot (Glomerella ingula)
te), powdery mildew (Uncinula necato)
r), rust disease (Phakopsora ampelop)
sidis), anthracnose of oyster (Gloeosporiu)
m kaki), leaf blight (Cercospora ka)
ki, Mycosphaerella hawae),
Downy mildew of cucurbits (Pseudoperonospora)
cubensis), anthracnose (Colletotri)
chum lagenarium), powdery mildew (Sp)
haerotheca fuliginea), vine blight (Mycosphaerella meloni)
s), Phytophthora in tomato
Festans), ring spot disease (Alternarias)
olani), leaf mold (Cladosporiumf)
ulvum), brown leaf spot of aubergine (Phomopsis v)
exans), powdery mildew (Erysiphe cic)
horakoarum), black spot of cruciferous vegetables (A
lternaria japonica), white spot (C
ercosporella brassicae, green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchi)
i), black scab (Elsinoe glycine)
s), Black spot disease (Diaporthe phaseo)
lum), kidney anthracnose (Colletotric)
hum lindemuthianum), peanut black astringent disease (Mycosphaerella perso)
natum), brown spot (Cercospora ara)
chidicola), powdery mildew of pea (Ery)
siphe pisi), summer blight of potato (Alt)
ernaria solani), powdery mildew of strawberry (Sphaerotheca humuli), rice blast of tea (Exobasidium reticula)
tum), white scab (Elsinoe leucospi)
la), tobacco scab (Alternaria li)
ngipes), powdery mildew (Erysiphe ci)
choracearum), anthracnose (Colletot)
Richum tabacum), sugar beet leaf spot (Cercospora beticola), rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannos)
a), Chrysanthemum leaf spot (Septoria chrysa)
nthemiindici), white rust (Puccin)
ia horiana), gray mold of various crops (B
otrytis cinerea), Sclerotinia sclerotioru of various crops
m) and the like.

On the other hand, the compounds of the present invention include extremely useful compounds having almost no adverse effects on mammals, fish, crustaceans and beneficial insects.

Next, in the above (1), G is G ¹ and A ² is A ² y
The production methods of the compounds of the present invention represented by the following are respectively described below. (Manufacturing method)

[0152]

[Chemical 21]

[0153]

[Chemical formula 22]

[0154]

[Chemical formula 23]

[0155]

[Chemical formula 24]

[0156]

[Chemical 25]

[0157]

[Chemical formula 26]

(A ³ and A ⁴ are independently the above A ¹
And a ring having a nitrogen atom at the α-position of the leaving group L ¹ or the imino bond, and A ⁵ is the above-mentioned A ¹
And a ring having an oxygen atom, a sulfur atom or a nitrogen atom at C = M ¹ or the α-position of the imino bond. X, n, Z, R ⁴ , A ¹ and A ² have the same meanings as described above. L ¹ is a good leaving group such as fluorine atom, chlorine atom, bromine atom, iodine atom, alkoxy having 1 to 4 carbon atoms, phenoxy, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms. , Alkylsulfonyloxy having 1 to 4 carbon atoms, benzenesulfonyloxy, toluenesulfonyloxy, 1-pyrazolyl, 1-imidazolyl and the like. L ² and L ⁶ are good leaving groups such as alkoxy having 1 to 4 carbons and 1 to 4 carbons.
Are alkylthio, phenoxy, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms, 1-pyrazolyl, 1-imidazolyl and the like. L ³ is independently a good leaving group such as chlorine atom, bromine atom, iodine atom, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, phenoxy, alkylamino having 1 to 4 carbon atoms. , C1-C4 dialkylamino, 1-pyrazolyl, 1-imidazolyl and the like. L ⁴ is a good leaving group such as a chlorine atom, a bromine atom, an iodine atom, and a carbon number of 1
~ 4 alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy and the like. L ⁵
Is a good leaving group such as a chlorine atom or a bromine atom. L ⁷ is an alkyl group having 1 to 4 carbon atoms, a phenyl group, a toluyl group, or the like. L ⁸ is a hydrogen atom, a trimethylsilyl group, a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group or the like. L
⁹ and L ¹⁰ each independently represent the same meaning as Y or together represent 1-imidazolyl, 1-pyrazolyl, 1-piperidinyl or morpholino. Y
¹ represents an alkyl group having 1 to 6 carbon atoms or ^a benzyl group which may be substituted with ^Ra . Y ² , Y ⁹ and Y ¹⁰ are
Each independently represents the same meaning as Y. Y ³ , Y ⁴ , Y ⁷ , Y ⁸
And Y ¹¹ each independently represent a hydrogen atom or the same meaning as Y. Y ⁵ and Y ⁶ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or ^a phenyl group which may be substituted with ^Ra . M represents an oxygen atom, a sulfur atom or N—Y ² . M ¹ represents an oxygen atom or a sulfur atom. M ² represents an oxygen atom, a sulfur atom or N—Y ⁹ . Hal represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. R ^a have the same meanings as defined above. The starting material, a nitronaphthyl acetic acid compound represented by the formula (3), can be prepared according to European Patent Application Publication (EP-57081).
7), Synthesis, page 51 (1993), Journal of Organic Chemistry (J. Org. Chem.), Vol. 61, 59.
It can be produced by a known method described on page 94 (1996) and the like. Examples of the method for producing the compound represented by the formula (9) from the nitronaphthyl acetic acid compound (3) include European Patent Application Publication (EP-447118), Organic Functional Group Preparations (Organic Functional Group).
Preparations (Academic)
Volume 1, p. 313 (1968), Journal of.
The American Chemical Society (J. Am.
Chem. Soc. ) 54, 781 (1932)
Year), Chemical Review (Chem. Rev.) No. 5
Volume 5, page 181 (1955) and the like can be used. That is, by converting the nitronaphthyl acetic acid compound (3) to an aminonaphthyl acetic acid compound (4) by a reduction reaction, by reacting with carbon disulfide in the presence of a base, a dithiocarbamic acid compound (5) is converted, Furthermore, dithiocarbamic acid compound (5)
Is converted into an isothiocyanate compound (7) by reacting with an acid halide compound represented by the formula (6), and then the isothiocyanate compound (7) is reacted with an amine compound represented by the formula (8). By doing so, the thiourea compound (9) can be produced. At this time, the thiourea compound (18) can be similarly produced by using ammonia as the amine compound. The isothiocyanate compound (7) can also be produced by a method of reacting the aminonaphthylacetic acid compound (4) with the thiocarbonyl compound represented by the formula (10). The thiourea compound (9) can also be produced by a method of reacting the aminonaphthyl acetic acid compound (4) with the isothiocyanate compound represented by the formula (11). In addition, the thiourea compound (9) was synthesized by Synthetic Communication (Syn
th. Commun. ) Vol. 25, No. 1, p. 43 (199
5 years), it can be converted to a carbodiimide compound (22) by reacting with a sulfonic acid halide compound (21).

Compounds (1-1) and (1-2) of the present invention
Is based on the aminonaphthyl acetic acid compound (4), Angewev Chemie, Volume 80,
It can be produced according to the method described on page 799 (1968) or according to the method. That is, the compound (1-1) of the present invention is obtained by alkylating a compound represented by the formula (12) in advance to form an ammonium salt represented by the formula (13) in a solvent, if necessary, as a catalyst. It can be produced by reacting with the aminonaphthyl acetic acid compound (4) in the presence. Similarly, the compound of the present invention (1-2)
Is obtained by alkylating the compound represented by the formula (14) into an oxonium salt or a thioxonium salt represented by the formula (15) in advance, and optionally in a solvent, optionally in the presence of a catalyst, aminonaphthyl acetic acid. It can be produced by reacting with compound (4). The solvent may be any solvent inert to the reaction, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, xylene and toluene, pentane, hexane and cyclohexane. And the like, and mixed solvents thereof and the like, and preferably dichloromethane, chloroform, 1,2-dichloroethane and the like. As the alkylating agent,
For example, alkyl halides such as methyl iodide, ethyl iodide, and benzyl bromide, dimethyl sulfate, diethyl sulfate, sulfonic acid esters such as methyl trifluoromethanesulfonate, trimethyloxonium tetrafluoroborate, triethyloxonium tetra Examples thereof include trialkyloxonium salts such as fluoroborate salts and the like, and preferable examples include trimethyloxonium tetrafluoroborate salts and the like. As the catalyst, for example,
Examples thereof include silver oxide and trifluoromethanesulfonic acid silver salt. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent.
The reaction time may be 5 minutes to 300 hours, preferably 1 hour to 168 hours. The equivalent of the alkylating agent can be used in the range of 0.5 to 50 equivalents based on (12) or (14), and is preferably in the range of 1 to 20 equivalents. As the equivalent of the substrate, (13) or (15) can be used in the range of 0.5 to 50 equivalents with respect to (4), and 1
The range of 20 to 20 equivalents is preferred.

The compound (1-3) of the present invention comprises the dithiocarbamic acid compound (5) and the ketone compound represented by the formula (16) in a solvent, if necessary, in the presence of a base, and in some cases, in the presence of a base. It can be produced by converting the compound into a dithiocarbamic acid ester compound (17) by reacting in the presence of a catalyst, and then reacting with a dehydrating agent in a solvent, if necessary, in the presence of a catalyst, if necessary.
The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Chloroform, 1,2-
Halogenated hydrocarbons such as dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide,
N-methylpyrrolidone, amides such as N, N'-dimethylimidazolidinone, pentane, hexane, aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof or the like, and preferably, Dichloromethane, chloroform, 1,2-dichloroethane and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As the dehydrating agent, concentrated sulfuric acid, dicyclohexylcarbodiimide, phosphorus pentachloride, phosphorus oxychloride or the like is used. Also, concentrated sulfuric acid can be used as a solvent. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents with respect to (5), and is preferably in the range of 0.1 to 20 equivalents. Further, as the equivalent of the substrate, (16) can be used in the range of 0.5 to 50 equivalents with respect to (5), and the range of 1 to 20 equivalents is preferable. The equivalent of the dehydrating agent can be used in the range of 0.1 to 100 equivalents with respect to (17), and is preferably in the range of 1 to 50 equivalents.

The compound (1-4) of the present invention contains the thiourea compound (9) and the carbonyl compound represented by the formula (19) in a solvent, if necessary, in the presence of a base, if necessary. It can be produced by reacting in the presence of a catalyst. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Chloroform,
Halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like. Amides, pentane, hexane, cyclohexane and other aliphatic hydrocarbons,
Examples thereof include dimethyl sulfoxide, water, a mixed solvent thereof, and the like, with preference given to ethanol, tetrahydrofuran, chloroform, dimethylformamide, and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. Examples of the catalyst include tetra-
N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time can be in the range of 5 minutes to 100 hours,
The range of 1 hour to 48 hours is preferable. The equivalent of the base can be used in the range of 0.1 to 50 equivalents with respect to (9), and the range of 1 to 20 equivalents is preferable. Also, as the equivalent of the substrate, (19) is (9)
It can be used in the range of 0.5 to 50 equivalents, with the range of 1 to 20 equivalents being preferred.

The compound (1-5) of the present invention contains the thiourea compound (9) and the acid halogen compound represented by the formula (20) in a solvent, if necessary, in the presence of a base, if necessary. Can be produced by reacting in the presence of a catalyst. The solvent may be any solvent inert to the reaction, for example, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane, chloroform and 1,2-dichloroethane. Halogenated hydrocarbons, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, pentane and hexane , Aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, and preferably tetrahydrofuran, chloroform, dimethylformamide and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature is
It can be carried out in the range of −80 ° C. to the boiling point of the solvent, and 0 ° C.
To the boiling point range of the solvent is preferred. As the reaction time,
It can be carried out for 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of base is
It can be used in the range of 0.1 to 50 equivalents relative to (9), and is preferably in the range of 1 to 20 equivalents. Further, as the equivalent of the substrate, (20) is 0.5 with respect to (9).
It can be used in the range of 1 to 50 equivalents, with the range of 1 to 20 equivalents being preferred.

The compound (1-6) of the present invention is obtained by reacting the carbodiimide compound (22) with a carbonyl compound (23) in a solvent, if necessary, in the presence of a base, and optionally in the presence of a catalyst. Can be manufactured by. The solvent may be any solvent inert to the reaction, for example, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane, chloroform and 1,2-dichloroethane. Halogenated hydrocarbons, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, pentane and hexane , Aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, preferably dichloromethane, chloroform, 1,2-dichloroethane and the like.
Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature is -80
It can be carried out in the range of 0 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be in the range of 5 minutes to 100 hours, and 1 hour to 48 hours.
A time range is preferred. The equivalent of base is (22)
However, it can be used in the range of 0.01 to 50 equivalents, and the range of 1 to 20 equivalents is preferable. Further, as the equivalent of the substrate, (23) can be used in the range of 0.5 to 50 equivalents with respect to (22), and the range of 1 to 20 equivalents is preferable.

The compound (1-7) of the present invention can be obtained by reacting the thiourea compound (9) with the amide compound represented by the formula (24). That is, the thiourea compound (9) and the amide compound represented by the formula (24) can be converted into the pseudothiourea compound (25) by reacting them in a solvent, if necessary, in the presence of a catalyst. Furthermore, a pseudo thiourea compound (2
5) can be converted to an imidoyl chloride compound (26) by treating with a halogenating agent in a solvent, if necessary, in the presence of a catalyst, if necessary. Further, (26) can be converted to the compound (1-7) of the present invention by reacting in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. Also,
By using a base in the reaction of (25) with a halogenating agent, (1-7) can be obtained without isolating (26). In the reaction of obtaining (9) to (25), the solvent may be any solvent inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, benzene, and the like. Aromatic hydrocarbons such as xylene and toluene, dichloromethane, chloroform,
Halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like. Amides, pentane, hexane, cyclohexane and other aliphatic hydrocarbons,
Examples thereof include dimethyl sulfoxide or water, or a mixed solvent thereof, and preferably ethanol, tetrahydrofuran, chloroform, 1,2-dichloroethane,
Examples thereof include ethyl acetate, acetone, acetonitrile, dimethylformamide, water and the like. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. Reaction time is 5 minutes to 1
It can be carried out in the range of 00 hours, preferably in the range of 1 to 48 hours. As the equivalent of the substrate, (24) can be used in the range of 0.5 to 50 equivalents with respect to (9), and the range of 1 to 20 equivalents is preferable. (25)
In the reaction for obtaining (26) to (26), any solvent may be used as long as it is inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, benzene, xylene and toluene. Such as aromatic hydrocarbons, dichloromethane, chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, Amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N, N'-dimethylimidazolidinone, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, etc. Enthusiasm And preferably include dichloromethane, chloroform, 1,2-dichloroethane and the like. As the halogenating agent, tetrachloroethane /
Examples thereof include triphenylphosphine, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, oxalic acid dichloride, chlorine and N-chlorosuccinimide. The reaction temperature is -8
It can be carried out in the range of 0 ° C. to the boiling point of the solvent, and preferably in the range of 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, and 1 hour to 4 hours.
A range of 8 hours is preferred. As the equivalent amount of the chlorinating agent,
It can be used in the range of 0.01 to 50 equivalents relative to (25), and preferably in the range of 0.1 to 20 equivalents.
In the reaction for obtaining (1-7) from (26), the solvent may be any solvent inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, Aromatic hydrocarbons such as benzene, xylene, toluene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, propionitrile Such as nitriles, dimethylformamide, dimethylacetamide, N
-Methylpyrrolidone, amides such as N, N'-dimethylimidazolidinone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, and the base includes For example, triethylamine, tributylamine,
Organic bases such as pyridine, N-methylpiperidine and 4-dimethylaminopyridine, and inorganic bases such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide and sodium hydride are used.
The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents with respect to (26), and preferably in the range of 0.1 to 20 equivalents.

The compound (1-10) of the present invention can be obtained by reacting the thiourea compound (9) with the ketone compound represented by the formula (16). That is, the pseudo thiourea compound (27) is obtained by reacting the thiourea compound (9) with the ketone compound represented by the formula (16) in a solvent, if necessary, in the presence of a catalyst as the case requires.
Can be converted to. Furthermore, the pseudothiourea compound (27) can be converted into the hydroxythiazolidine compound (1-8) by reacting it in a solvent in the presence of an acid or a basic catalyst, if necessary. Furthermore (1-
8) can be converted to the compound of the present invention (1-9) by optionally treating with a dehydrating agent in a solvent, optionally in the presence of a base, and optionally in the presence of a catalyst. Furthermore, (1-9) can be converted to a free compound (1-10) by treating with a base in a solvent, if necessary. In addition, by reacting (9) with (16) for a long period of time or by heat treatment or treatment with a catalyst, (27) or (1-8) can be obtained without isolation (1
-9) can also be obtained. In addition, in the reaction of (9) and (16), by using a base, without isolating (27) or (1-8) or (1-9), (1
-10) can also be obtained. Further, by using a base in the reaction of (1-8) with a dehydrating agent, (1-10) can be obtained without isolating (1-9).
It can also be obtained by treating the thiazoline compound (31) obtained similarly from the thiourea compound (18) with an alkylating agent in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. . In the reaction for obtaining (1-8) from (9), the solvent may be any solvent inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, Aromatic hydrocarbons such as benzene, xylene, toluene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, propionitrile And nitriles such as dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, and preferably. , Ethano Le, tetrahydrofuran, chloroform,
1,2-dichloroethane, ethyl acetate, acetone, acetonitrile, dimethylformamide, water and the like can be mentioned. Examples of the acidic catalyst include hydrochloric acid, hydrobromic acid, hydroiodic acid, hydrofluoric acid, acetic acid, tetrafluoroboric acid and the like. Examples of the basic catalyst include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, and hydrogenation. An inorganic base such as sodium is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. As the equivalent of the substrate, (16) can be used in the range of 0.5 to 50 equivalents with respect to (9), and the range of 1 to 20 equivalents is preferable. From the hydroxy thiazolidine compound (1-8) to the compound of the present invention (1-9)
In the reaction for obtaining, the solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran,
Ethers such as dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane,
Chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide,
Dimethylacetamide, N-methylpyrrolidone, N,
Amides such as N′-dimethylimidazolidinone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane,
Examples thereof include dimethyl sulfoxide, water, a mixed solvent thereof, and the like, and preferable examples include dichloromethane, chloroform, 1,2-dichloroethane and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. Also, pyridine or the like can be used as a solvent. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As the dehydrating agent, methanesulfonyl chloride, toluenesulfonyl chloride, trifluoromethanesulfonic anhydride, concentrated sulfuric acid, dicyclohexylcarbodiimide, phosphorus pentachloride, phosphorus oxychloride or the like is used. Also, concentrated sulfuric acid can be used as a solvent. It is also possible to carry out the reaction by azeotropic dehydration using a solvent such as toluene, benzene or xylene. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours.
The equivalent amount of the base can be used in the range of 0.01 to 50 equivalents based on (1-8), and is 0.1 to 20.
An equivalent range is preferred. The equivalent of the dehydrating agent is (1-
It can be used in the range of 0.1 to 100 equivalents, preferably 1 to 50 equivalents, based on 8). (1-
In the reaction for obtaining (1-10) from 9), the solvent may be any solvent inert to the reaction, for example, methanol,
Lower alcohols such as ethanol, diethyl ether,
Ethers such as tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, acetone, methyl ethyl ketone, etc. Ketones,
Acetonitrile, nitriles such as propionitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, amides such as N, N'-dimethylimidazolidinone, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, dimethyl sulfoxide Or water, or a mixed solvent thereof, and the like, and as the base,
For example, organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide,
An inorganic base such as sodium hydride is used. The reaction temperature may be -80 ° C to the boiling point of the solvent,
The range of 0 ° C. to the boiling point of the solvent is preferable. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents with respect to (1-9), and is preferably in the range of 0.1 to 20 equivalents. In the reaction for obtaining (1-10) from (31),
The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Chloroform, 1,2-
Halogenated hydrocarbons such as dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide,
Examples include amides such as N-methylpyrrolidone and N, N′-dimethylimidazolidinone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like. , For example, organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine and 4-dimethylaminopyridine, and inorganic bases such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide and sodium hydride. Is used. Examples of the alkylating agent include alkyl halides such as methyl iodide, ethyl iodide, and benzyl bromide, sulfonic acid esters such as dimethyl sulfuric acid, diethyl sulfuric acid, and trifluoromethanesulfonic acid methyl ester,
Examples thereof include trialkyloxonium salts such as trimethyloxonium tetrafluoroborate and triethyloxonium tetrafluoroborate, and preferably trifluoromethanesulfonic acid methyl ester and the like. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents with respect to (31), and preferably in the range of 0.1 to 20 equivalents. The equivalent amount of alkylating agent is (31)
On the other hand, it can be used in the range of 0.01 to 50 equivalents, preferably 0.1 to 20 equivalents.

Compounds (1-11) and (1-1) of the present invention
2) can be produced by the following method. That is, by reacting an isothiocyanate compound (7) with a propargylamine compound represented by the formula (32) in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. It can be converted to the propargyl thiourea compound represented by (33). further,
When (33) is treated with a radical generator in a solvent, if necessary, a mixture of (1-11) and (1-12) can be obtained. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide and N-methyl. Amides such as pyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water,
Alternatively, mixed solvents thereof and the like can be mentioned, and preferably tetrahydrofuran, chloroform, acetone, acetonitrile and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As a radical generator, trifluoroacetic acid,
Oxygen, air, benzoyl peroxide, azobisisobutyronitrile, etc. are used. Also, trifluoroacetic acid can be used as a solvent. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. Reaction time is 5 minutes to 10
It can be carried out for 0 hours, preferably for 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.05 to 150 equivalents based on (7), and is preferably in the range of 1 to 20 equivalents. Further, as the equivalent of the substrate, (32) is 0.5 to 5 relative to (7).
It can be used in a range of 0 equivalent, and a range of 1 to 20 equivalent is preferable.

The compound (1-13) of the present invention is obtained by treating the above-mentioned propargyl thiourea compound (33) with a halogenating agent in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. It can be manufactured. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N
-Amids such as methylpyrrolidone, pentane, hexane, aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, preferably dichloromethane, chloroform,
1,2-dichloroethane, acetonitrile and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As the halogenating agent, iodine, bromine, N-bromosuccinimide,
N-chlorosuccinimide, N-iodosuccinimide, tetrabutylammonium tribromide, etc. are used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours.
The equivalent of the base can be used in the range of 0.01 to 50 equivalents based on (33), and is preferably in the range of 1 to 20 equivalents. The equivalent amount of the halogenating agent is (3
It can be used in the range of 0.01 to 50 equivalents relative to 3) and is preferably in the range of 1 to 20 equivalents.

The compound (1-14) of the present invention can be produced by the method described in (1) above.
-13) and an amine compound, an alcohol compound or a mercaptan compound represented by the formula (34), if necessary, in a solvent, in the presence of a base, if necessary, in the presence of a catalyst, if necessary. . The solvent only needs to be inert to the reaction, for example, methanol,
Lower alcohols such as ethanol, diethyl ether,
Ethers such as tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, acetone, methyl ethyl ketone, etc. Ketones,
Nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethylsulfoxide or water, or a mixed solvent thereof, etc. Named
Preferred are tetrahydrofuran, benzene, chloroform, 1,2-dichloroethane, acetonitrile and the like. Examples of the base include triethylamine,
Organic bases such as tributylamine, pyridine, diazabicycloundecene, N-methylpiperidine, and 4-dimethylaminopyridine, cesium fluoride, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide,
An inorganic base such as potassium hydroxide or sodium hydride is used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature is -8
It can be carried out in the range of 0 ° C. to the boiling point of the solvent, and preferably in the range of 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, and 1 hour to 4 hours.
A range of 8 hours is preferred. The equivalent of base is (1-
It can be used in the range of 0.01 to 50 equivalents relative to 13) and is preferably in the range of 1 to 20 equivalents. Also,
As the equivalent of the substrate, (34) can be used in the range of 0.5 to 50 equivalents with respect to (1-13), and 1
The range of 20 to 20 equivalents is preferred.

Compounds (1-15) and (1-1) of the present invention
6) can be produced by the following method. That is, the isothiocyanate compound (7) and the allylamine compound represented by the formula (35) are added in a solvent, if necessary,
In the presence of a base, if necessary, in the presence of a catalyst,
It can be converted into an allylthiourea compound represented by the formula (36) by reacting. Further, (36) is optionally treated with a radical generator in a solvent to give a compound of the present invention (1-15) when Y ² is phenyl.
When Y ² is other than phenyl, the compound of the present invention (1-1
6) can be obtained respectively. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide and N-methyl. Examples thereof include amides such as pyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof. Preferred are tetrahydrofuran, chloroform, acetone, acetic acid. Tonitoriru, and the like. As the base, for example,
Triethylamine, tributylamine, pyridine, N-
Organic bases such as methylpiperidine and 4-dimethylaminopyridine and inorganic bases such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide and sodium hydride are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As the radical generator, trifluoroacetic acid, oxygen, air, benzoyl peroxide, azobisisobutyronitrile or the like is used. Also, trifluoroacetic acid can be used as a solvent. Reaction temperature is -80 ℃
To the boiling point of the solvent, preferably 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.05 to 150 equivalents based on (7), and is preferably in the range of 1 to 20 equivalents. Further, as the equivalent of the substrate, (35) is 0.5 to 5 relative to (7).
It can be used in a range of 0 equivalent, and a range of 1 to 20 equivalent is preferable.

The compound (1-17) of the present invention is obtained by treating the above-mentioned allylthiourea compound (36) with a halogenating agent in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. It can be manufactured. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N
-Amids such as methylpyrrolidone, pentane, hexane, aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, preferably dichloromethane, chloroform,
1,2-dichloroethane, acetonitrile and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As the halogenating agent, iodine, bromine, N-bromosuccinimide,
N-chlorosuccinimide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent,
The range of 0 ° C. to the boiling point of the solvent is preferable. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents based on (36), and is preferably in the range of 1 to 20 equivalents.
The equivalent amount of the halogenating agent is 0.0 with respect to (36).
It can be used in the range of 1 to 50 equivalents and 1 to 20
An equivalent range is preferred.

The compound (1-18) of the present invention can be produced by the method described in (1) above.
-17) and an amine compound, an alcohol compound or a mercaptan compound represented by the formula (34), if necessary, in a solvent, in the presence of a base, if necessary, in the presence of a catalyst. . The solvent only needs to be inert to the reaction, for example, methanol,
Lower alcohols such as ethanol, diethyl ether,
Ethers such as tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, acetone, methyl ethyl ketone, etc. Ketones,
Nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethylsulfoxide or water, or a mixed solvent thereof, etc. Named
Preferred are tetrahydrofuran, benzene, chloroform, 1,2-dichloroethane, acetonitrile and the like. Examples of the base include triethylamine,
Organic bases such as tributylamine, pyridine, diazabicycloundecene, N-methylpiperidine, and 4-dimethylaminopyridine, cesium fluoride, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide,
An inorganic base such as potassium hydroxide or sodium hydride is used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature is -8
It can be carried out in the range of 0 ° C. to the boiling point of the solvent, and preferably in the range of 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, and 1 hour to 4 hours.
A range of 8 hours is preferred. The equivalent of base is (1-
It can be used in the range of 0.01 to 50 equivalents relative to 17) and is preferably in the range of 1 to 20 equivalents. Also,
As the substrate equivalent, (34) can be used in the range of 0.5 to 50 equivalents relative to (1-17), and 1
The range of 20 to 20 equivalents is preferred.

The compound (1-19) of the present invention can be produced by the method described in Synthesis page 896 (1981) or by a method analogous thereto. That is,
It is obtained by reacting the isothiocyanate compound (7) with the olefin compound represented by the formula (37) in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, and dichloromethane. , Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide and N-methyl. Amides such as pyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water,
Alternatively, a mixed solvent thereof and the like can be mentioned, and preferably,
Tetrahydrofuran, benzene, chloroform, 1,2
-Dichloroethane, acetonitrile and the like. The equivalent amount of the base is 0.01 to 50 relative to (7).
It can be used in an equivalent range, and a range of 1 to 20 equivalents is preferable. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature is
It can be carried out in the range of −80 ° C. to the boiling point of the solvent, and 0 ° C.
To the boiling point range of the solvent is preferred. As the reaction time,
It can be carried out for 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of base is
It can be used in the range of 0.01 to 50 equivalents relative to (7), and is preferably in the range of 1 to 20 equivalents. Also,
As the equivalent of the substrate, (37) was 0.
It can be used in the range of 5 to 50 equivalents and 1 to 20
An equivalent range is preferred.

The compound (1-20) of the present invention can be produced according to the method described in West German Patent Application Publication (DE-3025559) or according to the method. That is, the isothiocyanate compound (7) and the formula (38)
In a solvent with a hydrazine compound represented by, if necessary,
Depending on the case, it can be converted to a thiosemicarbazide compound (39) by reacting in the presence of a catalyst. Further, the compound is converted into an acylthiosemicarbazide compound (41) by reacting with a carbonyl compound represented by the formula (40) in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. can do. further,
The compound (1-20) of the present invention can be obtained by treating the acylthiosemicarbazide compound (41) with a dehydrating agent in a solvent, if necessary, in the presence of a catalyst, if necessary. In the reaction for obtaining the thiosemicarbazide compound (39) from the isothiocyanate compound (7), the solvent may be any solvent inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, dimethoxyethane. Ethers such as benzene, xylene, aromatic hydrocarbons such as toluene, dichloromethane, chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, Acetonitrile, nitriles such as propionitrile, dimethylformamide, dimethylacetamide, N
-Amids such as methylpyrrolidone, pentane, hexane, aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or a mixed solvent thereof, and the like, preferably tetrahydrofuran, chloroform,
1,2-dichloroethane, acetone, acetonitrile,
Examples thereof include dimethylformamide. As a catalyst,
For example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. As the equivalent of the substrate, (38) is (7),
It can be used in the range of 0.01 to 50 equivalents, and the range of 1 to 20 equivalents is preferable. From the thiosemicarbazide compound (39) to the acylthiosemicarbazide compound (4
In the reaction for conversion into 1), the solvent may be any solvent inert to the reaction, and examples thereof include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane, Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, esters such as ethyl acetate,
Ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, or dimethyl sulfoxide or these And the like, and preferably tetrahydrofuran, chloroform, 1,2-dichloroethane, acetone, acetonitrile, dimethylacetamide and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, diazabicycloundecene, N-methylpiperidine, and 4-dimethylaminopyridine, and cesium fluoride, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, and hydroxide. Inorganic bases such as sodium, potassium hydroxide and sodium hydride are used. Examples of the catalyst include tetra-N-
Butyl ammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent,
The range of 0 ° C. to the boiling point of the solvent is preferable. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents based on (39), and is preferably in the range of 1 to 20 equivalents.
As the equivalent of the substrate, (40) is (39),
It can be used in the range of 0.01 to 50 equivalents, and the range of 1 to 20 equivalents is preferable. In the reaction for obtaining the compound (1-20) of the present invention from the acylthiosemicarbazide compound (41), the solvent may be any one inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, diethyl ether, Tetrahydrofuran, ethers such as dimethoxyethane, benzene, xylene,
Aromatic hydrocarbons such as toluene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile. , Dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, dimethyl sulfoxide, or a mixed solvent thereof, and the like, and preferably benzene, xylene, chloroform and the like. Is mentioned. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. As the dehydrating agent, concentrated sulfuric acid, dicyclohexylcarbodiimide, phosphorus pentachloride, phosphorus oxychloride or the like is used. Also, concentrated sulfuric acid can be used as a solvent. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent amount of the dehydrating agent is 0.01 with respect to (41).
It can be used in the range of 1 to 50 equivalents, with the range of 1 to 20 equivalents being preferred.

The compound (1-21) of the present invention can be produced according to the method described in West German Patent Application Publication (DE-3025559) or according to the method. That is, the aforementioned acylthiosemicarbazide compound (41)
Can be obtained by reacting with an alkylating agent, optionally in a solvent, optionally in the presence of a base, and optionally in the presence of a catalyst. The solvent may be any one inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, benzene,
Aromatic hydrocarbons such as xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, propionitrile and the like. Nitriles, dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water,
Alternatively, a mixed solvent thereof and the like can be mentioned, and preferably,
Ethanol, tetrahydrofuran, chloroform, 1,
2-dichloroethane, dimethylacetamide and the like can be mentioned. Examples of the alkylating agent include methyl iodide,
Alkyl halides such as ethyl iodide and benzyl bromide, sulfonic acid esters such as dimethylsulfate, diethylsulfate and methyl methyl trifluoromethanesulfonate,
Examples include trialkyloxonium salts such as trimethyloxonium tetrafluoroborate and triethyloxonium tetrafluoroborate. As a catalyst,
For example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent amount of alkylating agent is (4
It can be used in the range of 0.01 to 50 equivalents relative to 1) and is preferably in the range of 1 to 20 equivalents.

The compound (1-22) of the present invention contains the above-mentioned thiosemicarbazide compound (39) and the ketone compound represented by the formula (16) in a solvent, if necessary, in the presence of a base, if necessary. In some cases, it can be obtained by reacting in the presence of a catalyst. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran,
Ethers such as dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane,
Chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide,
Examples thereof include amides such as dimethylacetamide and N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, with preference given to ethanol, tetrahydrofuran, chloroform and 1 , 2-dichloroethane, acetone, acetonitrile, dimethylformamide and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours.
The equivalent of the base can be used in the range of 0.05 to 150 equivalents based on (39), and the range of 1 to 20 equivalents is preferable. The equivalent of the substrate is (1
6) can be used in the range of 0.5 to 50 equivalents with respect to (39), and the range of 1 to 20 equivalents is preferable.

The compound (1-23) of the present invention is prepared by reacting the isothiocyanate compound (7) with the hydrazine compound represented by the formula (42) in a solvent, if necessary, in the presence of a catalyst. , A thiosemicarbazide compound (43), and then further reacting with a ketone compound represented by the formula (16) in a solvent, if necessary, in the presence of a base, and optionally in the presence of a catalyst. can get. Isothiocyanate compound (7)
From the above, in the reaction for obtaining the thiosemicarbazide compound (43), the solvent may be any solvent inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol,
Ethers such as diethyl ether, tetrahydrofuran, dimethoxyethane, etc., aromatic hydrocarbons such as benzene, xylene, toluene, dichloromethane, chloroform,
Halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like. Examples thereof include amides, aliphatic hydrocarbons such as pentane, hexane, and cyclohexane, dimethyl sulfoxide, a mixed solvent thereof, and the like, with preference given to ethanol, tetrahydrofuran, chloroform, acetonitrile, and the like.
As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. Reaction time is 5 minutes to 10
It can be carried out for 0 hours, preferably for 1 hour to 48 hours. As the equivalent of the substrate, (42) can be used in the range of 0.01 to 50 equivalents with respect to (7), and the range of 1 to 20 equivalents is preferable. From the thiosemicarbazide compound (43) to the compound of the present invention (1-2
In the reaction for obtaining 3), any solvent may be used as long as it is inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, benzene, xylene, toluene and the like. Aromatic hydrocarbons, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethyl Formamide, dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water,
Alternatively, a mixed solvent thereof and the like can be mentioned, and preferably,
Tetrahydrofuran, benzene, xylene, chloroform, dimethylacetamide, N-methylpyrrolidone and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. Examples of the catalyst include tetra-
N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time can be in the range of 5 minutes to 100 hours,
The range of 1 hour to 48 hours is preferable. The equivalent of the base can be used in the range of 0.05 to 150 equivalent based on (43), and the range of 1 to 20 equivalent is preferable. Further, as the equivalent of the substrate, (16) can be used in the range of 0.5 to 50 equivalents with respect to (43), and the range of 1 to 20 equivalents is preferable.

The compound (1-24) of the present invention contains the above-mentioned thiosemicarbazide compound (43) and the carbonyl compound represented by the formula (19) in a solvent, if necessary, in the presence of a base, if necessary. Can be produced by reacting in the presence of a catalyst. The solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran,
Ethers such as dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane,
Chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide,
Dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, dimethyl sulfoxide or water, or mixed solvents thereof, and the like, and preferably ethanol, tetrahydrofuran, chloroform, dimethyl. Formamide and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours.
The equivalent of base is 0.1 to 5 relative to (43).
It can be used in a range of 0 equivalent, and a range of 1 to 20 equivalent is preferable. Further, as the equivalent of the substrate, (19) can be used in the range of 0.5 to 50 equivalents with respect to (43), and the range of 1 to 20 equivalents is preferable.

The compound (1-25) of the present invention can be produced by the method described in Heterocycles, Vol. 50, p. 195 (1999), or according to the method. That is, isothiocyanate compound (7)
And a mercaptan compound represented by the formula (44) are reacted in a solvent, if necessary, in the presence of a base, and optionally in the presence of a catalyst to give a dithiocarbamate compound (45). The compound can be converted to the dithioacetal compound (2-1) by treating with an alkylating agent in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. Further, by reacting the dithioacetal compound (2-1) and the carbonyl compound represented by the formula (46) in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst (2 A mixture of -2) and (1-25) is obtained. In addition, in the reactions from (7) to (2-1), (4
It is also possible to obtain (2-1) without isolating 5). In addition, in the reaction of (2-1) to (1-25), (1-25) can be obtained by isolating (2-2) by heating for a long time or by heating. In addition, the isolated (2-2) is converted into (1-25) by reacting or heating in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst, if necessary. You can also do it. In the reaction from (7) to (2-1), the solvent may be any solvent inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, Aromatic hydrocarbons such as benzene, xylene, toluene, dichloromethane, chloroform,
Halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like. Amides, pentane, hexane, cyclohexane and other aliphatic hydrocarbons,
Dimethyl sulfoxide or water, or a mixed solvent thereof or the like can be mentioned, preferably tetrahydrofuran,
Benzene, toluene, dichloromethane, chloroform,
1,2-dichloroethane, acetone, acetonitrile,
Examples thereof include dimethylacetamide. As a base,
For example, organic bases such as triethylamine, tributylamine, pyridine, diazabicycloundecene, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, hydrogenation. An inorganic base such as sodium is used. Examples of the catalyst include tetra-
N-butylammonium bromide or the like is used. Examples of the alkylating agent include alkyl halides such as methyl iodide, ethyl iodide and benzyl bromide, sulfonic acid esters such as dimethyl sulfuric acid, diethyl sulfuric acid and trifluoromethanesulfonic acid methyl ester, trimethyloxonium tetrafluoroboric acid. Examples thereof include salts and trialkyloxonium salts such as triethyloxonium tetrafluoroborate. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. Reaction time is 5 minutes to 10
It can be carried out for 0 hours, preferably for 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.01 to 50 equivalents with respect to (7),
A range of 1 to 20 equivalents is preferred. Further, it can be used in the range of 0.01 to 50 equivalents relative to (45), and the range of 1 to 20 equivalents is preferable. As the equivalent of the substrate, (44) can be used in the range of 0.01 to 50 equivalents with respect to (7), and the range of 1 to 20 equivalents is preferable. In addition, the alkylating agent is (0) to (45).
It can be used in the range of 01 to 50 equivalents and 1 to 2
A range of 0 equivalents is preferred. (2-1) to (1-25)
In the reaction to, the solvent may be any solvent inert to the reaction, for example, lower alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, benzene, xylene,
Aromatic hydrocarbons such as toluene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile. , Dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or a mixed solvent thereof, and the like, and preferably tetrahydrofuran, xylene, toluene and the like. Is mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, diazabicycloundecene, N-methylpiperidine, and 4-dimethylaminopyridine, and cesium fluoride, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, and hydroxide. Inorganic bases such as sodium, potassium hydroxide and sodium hydride are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent amount of the base is 0.
It can be used in the range of 01 to 50 equivalents and 1 to 2
A range of 0 equivalents is preferred. The equivalent of the substrate is (4
6) can be used in the range of 0.01 to 50 equivalents with respect to (2-1), and the range of 1 to 20 equivalents is preferable.

The compound (1-26) of the present invention is disclosed in JP-A-55-55
-108869 and Chemistry Letters (Che
mistry Letters, p. 1705 (1988)
(Year), or according to the method described. That is, the isothiocyanate compound (7) and the amine compound represented by the formula (47) can be converted to a thiourea compound (48) by reacting them in a solvent, if necessary, in the presence of a catalyst, if necessary. Further, the thiourea compound (48) is a pseudothiourea compound obtained by reacting the ketone compound represented by the formula (16) with a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst. It can be converted into (2-3), and further (2-3) can be converted into a free compound (2-4) by treating with a base in a solvent, if necessary. Further, (2-4) can be converted to the compound of the present invention (1-26) by treating with acid in a solvent, if necessary. Further, in the reaction of the thiourea compound (48) with the ketones (16), by using an excessive amount of base,
(2-4) can also be obtained without isolating (2-3). Further, by reacting the thiourea compound (48) with the ketones (16) for a long period of time or by heat treatment, (2-3) and (2-4) can be obtained without isolation (1-26). You can also get In the reaction for obtaining the thiourea compound (48) from the isothiocyanate compound (7), a solvent may be inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, dimethoxyethane and the like. Ethers, aromatic hydrocarbons such as benzene, xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile , Nitriles such as propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone,
Pentane, hexane, aliphatic hydrocarbons such as cyclohexane or dimethyl sulfoxide or a mixed solvent thereof, and the like, preferably tetrahydrofuran,
Chloroform, 1,2-dichloroethane, ethyl acetate,
Examples include acetonitrile and dimethylacetamide. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. Reaction temperature is -80 ℃
To the boiling point of the solvent, preferably 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. As the equivalent of the substrate, (47) can be used in the range of 0.01 to 50 equivalents relative to (7), and the range of 1 to 20 equivalents is preferable. In the reaction for obtaining the compound (1-26) of the present invention from the thiourea compound (48), the solvent may be any one inert to the reaction, and examples thereof include lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, dimethoxy. Ethers such as ethane, benzene, xylene,
Aromatic hydrocarbons such as toluene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile. , Dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, preferably tetrahydrofuran and chloroform. , 1,2-dichloroethane, acetone, acetonitrile, dimethylformamide and the like. Examples of the base include triethylamine,
Tributylamine, pyridine, N-methylpiperidine,
An organic base such as 4-dimethylaminopyridine or an inorganic base such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide or sodium hydride is used. Examples of the catalyst include tetra-N-
Butyl ammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent,
The range of 0 ° C. to the boiling point of the solvent is preferable. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.05 to 150 equivalents with respect to (48), and the range of 1 to 20 equivalents is preferable. Further, as the equivalent of the substrate, (16) can be used in the range of 0.5 to 50 equivalents relative to (48), and the range of 1 to 20 equivalents is preferable.

The compound (1a) of the present invention is reacted with a formic acid halide compound, a formic acid ester compound or a formic acid amide compound represented by the formula (49) in a solvent in the presence of a base and, in some cases, a catalyst to give the compound of the present invention. Invention compound (1
It can be converted to b). Further, (1b) is reacted with an alkyl halide represented by formula (50), an alkyl sulfate ester, or the like in a solvent, if necessary, in the presence of a base, if necessary, in the presence of a catalyst, to give It can be converted to the invention compound (1c). Also, from (1a) to (1
In the reaction to b), it is possible to directly synthesize (1c) without isolation of (1b) by using an excess of base. The solvent may be any inert as long as it is inert to the reaction, and examples thereof include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane, chloroform and 1,2-.
Halogenated hydrocarbons such as dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide,
Amides such as N-methylpyrrolidone, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof and the like can be mentioned, and preferably tetrahydrofuran, benzene,
Xylene, toluene, dichloromethane, chloroform,
1,2-dichloroethane, acetonitrile, dimethylformamide and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours.
The equivalent of the base can be used in the range of 0.05 to 150 equivalents, preferably 1 to 20 equivalents, relative to (1a). The equivalent of the substrate is (4
9) can be used in the range of 0.5 to 50 equivalents with respect to (1a), and the range of 1 to 20 equivalents is preferable.

The compound represented by the formulas G ² to G ¹⁴ of G in (1) has a group represented by the formulas G ² to G ¹⁴ at the ortho position of nitronaphthalene instead of the naphthyl acetic acid compound as a raw material. It can be similarly produced by using the substituted compound as a starting material.

G at the ortho position of nitronaphthalene², G^Five，
G⁶Or G⁷The compound in which the group represented by
International application publication WO96 / 26191, International application publication WO
96/36615 or JP-A-9-104676
G referring to the method described in the report³Or G⁹The base represented by
The converted compounds are, for example, those described in WO99 / 20615.
G referring to the law^FourCompounds substituted by
With reference to the method described in the publication WO96 / 36229, G^TenBut
Substituted compounds are described, for example, in German Patent 19756115.
G referring to the method described¹¹, G¹²Or G¹⁴Replaced by
The compound is described in, for example, JP-A No. 11-335361.
Refer to the method of G¹³Compounds substituted by
Japanese Patent Laid-Open No. 11-220050 and Japanese Patent Laid-Open No. 7-179450.
It can be manufactured by referring to the method described in
it can. Also, A of (1)²Is the expression A²a to A²d, A²h
To A²m, A²o to A²Table with q or A²v to A²w
As a raw material, instead of the naphthalene ring
By using a compound having a corresponding heterocycle,
Can be manufactured like Also, A ²Is the expression A²e or A²Table with f
As a raw material, the compound
Instead of the corresponding aminopyrazole-N-acetic acid compound
It can be similarly produced by using the product. The raw material
The minopyrazole-N-acetic acid compound is produced by the following method.
Can be built.

[0183]

[Chemical 27]

(X, n and Z have the same meanings as described above, and L ¹¹ is a good leaving group such as chlorine atom, bromine atom,
Examples thereof include iodine atom, alkylsulfonyloxy having 1 to 4 carbon atoms, benzenesulfonyloxy, and toluenesulfonyloxy. ) Nitropyrazole-N-acetic acid compounds (53) and (5
4) can be produced by reacting the haloacetic acid compound represented by the formula (52) with a nitropyrazole compound (51) in a solvent in the presence of a base and, in some cases, a catalyst. The solvent may be any solvent inert to the reaction, for example, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane, chloroform and 1,2-dichloroethane. Halogenated hydrocarbons, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, pentane and hexane , Aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or mixed solvents thereof, and the like, preferably, tetrahydrofuran, benzene, xylene, toluene, dichloromethane,
Examples include chloroform, 1,2-dichloroethane, acetonitrile, dimethylformamide and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, and the like.
Inorganic bases such as sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide and sodium hydride are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of base is (51),
It can be used in the range of 0.05 to 150 equivalents, and 1
The range of 20 to 20 equivalents is preferred. Further, as the equivalent of the substrate, (52) can be used in the range of 0.5 to 50 equivalents with respect to (51), and the range of 1 to 20 equivalents is preferable. The obtained mixture of (53) and (54) can be separated and purified by an arbitrary purification method such as recrystallization or column chromatography. It can also be used for the next reaction without separation. From (53) to (5
5) or (54) to (56) can be similarly produced according to the above-mentioned method for producing the aminonaphthyl compound (4) from the nitronaphthyl acetic acid compound (3). Alternatively, the mixture of (55) and (56) can be obtained without separating (53) and (54), and then separated and purified by any purification method such as recrystallization or column chromatography.

The nitropyrazole compound (51) can be obtained, for example, from Journal of Organic Chemistry (J. Org. Chem.) Vol. 38, page 1777 (1).
973).

The aminopyrazole-N-acetic acid compounds (55) and (56) are aminopyrazole compounds represented by the formula (52) in a solvent in the presence of a base and, in some cases, a catalyst. It can be produced by reacting with compound (57). The solvent may be any solvent inert to the reaction, for example, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, dichloromethane, chloroform and 1,2-dichloroethane. Halogenated hydrocarbons, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, pentane and hexane , Aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof, and the like, and preferably tetrahydrofuran, benzene, xylene, toluene, dichloromethane, chloroform, 1,2-diene. Roroetan, acetonitrile, dimethylformamide and the like. Examples of the base include triethylamine,
Tributylamine, pyridine, N-methylpiperidine,
An organic base such as 4-dimethylaminopyridine or an inorganic base such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide or sodium hydride is used. Examples of the catalyst include tetra-N-
Butyl ammonium bromide or the like is used. The reaction temperature may be -80 ° C to the boiling point of the solvent,
The range of 0 ° C. to the boiling point of the solvent is preferable. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base can be used in the range of 0.05 to 150 equivalents based on (57), and the range of 1 to 20 equivalents is preferable. Further, as the equivalent of the substrate, (52) can be used in the range of 0.5 to 50 equivalents with respect to (57), and the range of 1 to 20 equivalents is preferable. Obtained (5
The mixture of 5) and (56) can be separated and purified by any purification method such as recrystallization and column chromatography. It can also be used for the next reaction without separation.

[0187] The compound A ² is represented by the formula A ² g is
It can be similarly produced by using a corresponding aminopyrazole-N-acetic acid compound as a raw material.

[0188] Further, A ² has the formula A ² r, A ² s, for the compounds represented by A ² t or A ² u, it can be prepared via the same manner N- acid compound.

The compound of the present invention in which A ¹ in the above (1) is represented by an oxothiolene ring or a dithiolene ring can also be produced by the following method.

[0190]

[Chemical 28]

(Y ³ , Y ⁴ and L ⁴ have the same meanings as described above, A ³ has the same meaning as A ^2, and L ^{1 2} and L ¹³ are
It represents C ₁ -C ₆ alkyl, or L ¹² and L ¹³ together represent a piperazine ring, a morpholine ring or a pyrrolidine ring. ) When A ¹ is an oxothiolene ring, a commercially available tetramethylthiourea (58) and a ketone compound (16) are reacted with each other in a solvent, if necessary, in the presence of a base, to give an oxathioleniminium salt. It can be (59). Further, the obtained (59) is reacted with a heterocyclic amine (60) to give the compound (1) of the present invention.
-27) can be obtained.

When A ¹ is a dithiolene ring, the amine (61) is sequentially treated with carbon disulfide and a ketone compound (16) to give a dithiocarbamate compound (6
2) and then dehydration with concentrated sulfuric acid or tetrafluoroboric acid to give a dithioleniminium salt (63)
Can be Furthermore, the compound (1-28) of the present invention can be obtained by reacting the obtained (63) with a heterocyclic amine (60).

In the reaction for obtaining the oxathioleniminium salt (59) from teteramethylthiourea (58), a solvent may be used as long as it is inert to the reaction, and examples thereof include diethyl ether, tetrahydrofuran, dimethoxyethane and dioxane. Etc., aromatic hydrocarbons such as benzene, xylene, toluene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, Acetonitrile, nitriles such as propionitrile, dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone or pentane, hexane, aliphatic hydrocarbons such as cyclohexane or a mixed solvent thereof, and the like, and preferably, The Hexane, tetrahydrofuran, benzene, xylene, toluene, dichloromethane,
Examples include chloroform, 1,2-dichloroethane, acetonitrile, dimethylformamide and the like. The reaction temperature may be -80 ° C to the boiling point of the solvent,
The range of 0 ° C. to the boiling point of the solvent is preferable. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. As the equivalent of the substrate, (16) can be used in the range of 0.5 to 50 equivalents with respect to (58), and the range of 1 to 20 equivalents is preferable. In the reaction for obtaining the compound (1-28) of the present invention from the oxathioleniminium salt (59), the solvent may be any inert as long as it is inert to the reaction, and examples thereof include diethyl ether, tetrahydrofuran, dimethoxyethane and dioxane. Aromatic hydrocarbons such as ethers, benzene, xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, Nitriles such as propionitrile, amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, and aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and mixed solvents thereof, and the like, and preferably dioxane, Tetrahydr Furan, benzene, xylene, toluene, dichloromethane, chloroform,
1,2-dichloroethane, acetonitrile, dimethylformamide and the like can be mentioned. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. Also, pyridine or the like can be used as a solvent. Reaction temperature is -80 ℃
To the boiling point of the solvent, preferably 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of base is (5
It can be used in the range of 0.5 to 50 equivalents, preferably 1 to 20 equivalents, based on 9). As the equivalent of the substrate, (60) is 0.5 to 5 with respect to (59).
It can be used in a range of 0 equivalent, and a range of 1 to 20 equivalent is preferable.

From the amine compound (61) to the dithiocarbamate compound (62), a dithioleniminium salt (6
The reaction for obtaining 3) is based on Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bul).
l) Volume 17, page 1924 (1969), Tetrahedron Letters
rs) 1137 (1971) and Chemical and Pharmaceutical Bulletin (Chem.
Pharm. Bull) 20: 1711 (197)
2 years) or a method similar thereto. In the reaction for obtaining the compound (1-29) of the present invention from the dithioleniminium salt (63), the solvent may be inert to the reaction, and examples thereof include ethers such as diethyl ether, tetrahydrofuran, dimethoxyethane and dioxane. , Benzene, xylene, toluene and other aromatic hydrocarbons, dichloromethane, chloroform,
Halogenated hydrocarbons such as 1,2-dichloroethane, esters such as ethyl acetate, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like. Amides or pentanes, hexane, aliphatic hydrocarbons such as cyclohexane, or mixed solvents thereof, and the like, and preferably,
Dioxane, tetrahydrofuran, benzene, xylene, toluene, dichloromethane, chloroform, 1,2
-Dichloroethane, acetonitrile, dimethylformamide and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogencarbonate,
Inorganic bases such as sodium hydroxide, potassium hydroxide and sodium hydride are used. Also, pyridine or the like can be used as a solvent. The reaction temperature may be -80 ° C to the boiling point of the solvent, preferably 0 ° C to the boiling point of the solvent. Reaction time is 5 minutes to 100
It can be carried out for a period of time, preferably from 1 hour to 48 hours. As the equivalent of the base, the base can be used in the range of 0.5 to 50 equivalents based on (63), and the range of 1 to 20 equivalents is preferable. As the equivalent of the substrate, (60) can be used in the range of 0.5 to 50 equivalents with respect to (63), and the range of 1 to 20 equivalents is preferable.

Also, A ³ is

[0196]

[Chemical 29]

When (X ¹ , X ³ , X ⁴ and n have the same meanings as described above),

[0198]

[Chemical 30]

(Y ³ , Y ⁴ , A ³ , L ¹¹ and Z have the same meanings as above.) (1-27) or (1-28) obtained in the same manner as above.
If necessary, the compound of the present invention (1-29) or (1-30) can be obtained by treating the compound with the haloacetic acid compound (52) in the presence of a base, if necessary, in a solvent.

In the reaction for obtaining the compound (1-29) or (1-30) of the present invention from (1-27) or (1-28), the solvent may be any one inert to the reaction,
For example, ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, aromatic hydrocarbons such as benzene, xylene and toluene, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate. , Ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone,
Pentane, hexane, aliphatic hydrocarbons such as cyclohexane, dimethyl sulfoxide or water, or a mixed solvent thereof and the like can be mentioned, and preferably tetrahydrofuran, benzene, xylene, toluene, dichloromethane, chloroform, 1,2-dichloroethane, acetonitrile. , Dimethylformamide and the like. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, N-methylpiperidine, and 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, and the like. Inorganic bases are used. As the catalyst, for example, tetra-N-butylammonium bromide or the like is used. Reaction temperature is -80 ℃
To the boiling point of the solvent, preferably 0 ° C. to the boiling point of the solvent. The reaction time may be 5 minutes to 100 hours, preferably 1 hour to 48 hours. The equivalent of the base is (1-2
7) or (1-28), 0.05 to 150
It can be used in an equivalent range, and a range of 1 to 20 equivalents is preferable. Further, as the equivalent of the substrate, (52) can be used in the range of 0.5 to 50 equivalents with respect to (1-27) or (1-28), and the range of 1 to 20 equivalents is preferable.

The compound of the present invention or an intermediate thereof produced in each step can be obtained from the reaction solution by a conventional method. It can be separated and purified by any purification method.

Examples of compounds included in the present invention are shown in Tables 1 to 5. However, the compound of the present invention is not limited to these.

The abbreviations in the table have the following meanings.

Me: methyl group, Et: ethyl group, Pr:
Propyl group, Bu: butyl group, Pen: Pentyl group, He
x: Hexyl group, Hep: is heptyl group, Oct: Octyl group, Non: Nonyl group, Dec: Decyl group, Und
ec: undecanyl group, Dodec: dodecyl group, P
h: phenyl group, n: normal, i: iso, s: secondary, t: tertiary, c: cyclo.

Also, the meaning of Ya in the table is different from the above.

[Table 1]

[0207]

[Chemical 31]

[0208]

[Chemical 32]

[0209]

[Chemical 33]

[0210]

[Chemical 34]

[0211]

[Chemical 35]

[0212]

[Chemical 36]

[0213]

[Chemical 37]

[0214]

[Chemical 38]

[0215]

[Chemical Formula 39]

[0216]

[Chemical 40]

[0217]

[Chemical 41]

[0218]

[Chemical 42]

[0219]

[Chemical 43]

[0220]

[Chemical 44]

[0221]

[Chemical formula 45]

[0222]

[Chemical formula 46]

[0223]

[Chemical 47]

[0224]

[Chemical 48]

[0225]

[Chemical 49]

[0226]

[Table 1] ――――――――――――――――――――――――――――――――――― Ya Yb X ―――――――――― ――――――――――――――――――――――――――― HHH H Cl H HFH H Br H HIH H Me HH Et HH n-Pr HH i-Pr HH n -Bu HH i-Bu HH s-Bu HH t-Bu HH n-Pen HH 3-Me-n-Bu HH n-Hex HH Ethenyl HH 1-Propenyl HH Ethynyl HH CF ₃ H H c-Pr H H c-Hex H H MeO H H t-BuO H H CF ₃ OH H MeS H H MeSO H H MeSO ₂ H H NO ₂ H H NC H H CHO H H Me ₂ NH H PhCH ₂ H H PhCH = CH H H 4-Cl-PHCH = CH H H PhCH = CHCH ₂ HH PhCC HH Ph HH MeNHC (O) HH PhNHC (O) HH EtNHC (O) HH 2-F-PhNHC (O) HH 3-F-PhNHC (O) HH 4-F-PhNHC (O) HH 2-Cl -PhNHC (O) HH 3-Cl-PhNHC (O) HH 4-Cl-PhNHC (O) HH 2-Me-PhNHC (O) HH 3-Me-PhNHC (O) HH 4-Me-PhNHC (O) HH 2-Br-PhNHC (O) HH 3-Br-PhNHC (O) HH 4-Br-PhNHC (O) HH 2-MeO-PhNHC (O) HH 3-MeO-PhNHC (O) HH 4-MeO- PhNHC (O) HH 2,6-F ₂ -PhNHC (O) H H MeOC (O) H H MeOCH ₂ H H MeOC (= NOMe) H H MeC (= NOMe) H H MeC (O) H H CH ₂ SMe H H CH ₂ SCH ₂ Ph H H Pyrazol-1-ylCH ₂ H H ClCH ₂ H H BrCH ₂ H H CF ₃ CF ₂ HH PhC (O) NH HH 1-Naphthyl HH 2-Naphthyl HH 1-Me-Pyrazol-5-yl HH 1-Me-3-Cl-Pyrazol-5-yl HH 2-F-Furan-3-yl HH Oxazol -2-yl HH 1,2,4-Oxadiazol-3-yl HH 1,2,4-Thiadizazol-5-yl HH 1,2,4-Triazol-1-yl HH 1,2,3-Triazol-1 -yl HH 1,2,3,4-Tetrazol-1-yl HH 6-MeO-Pyrimidin-2-yl HH Pyridazin-3-yl HH 1,3,5-Triazin-2-yl HH 1,2,4 -Triazin-6-yl HH 1-Me-Pyrrol-2-yl HH Furan-2-yl HH Thiophen-2-yl HH Thiazol-5-yl HH 2,4-Me ₂ -Oxazol-5-yl HH 3-Me-Isothiazol-5-yl HH Isoxazol-5-yl HH 1-Me-Imidazol-5-yl HH 4-Me-1,2,3-Thiadiazol-5-yl HH Pyridin -4-yl HH Quinoxalin-2-yl HH 6-Cl-Quinoxalin-2-yl HH 6-F-Quinoxalin-2-yl HH 1-Me-Indol-3-yl HH Benzothiazol-2-yl HH 5-F -Benzothiazol-2-yl HH 6-F-Benzothiazol-2-yl HH Quinolin-4-yl HH Pyrazin-2-yl HH 4-CClF ₂ -Pyrimidin-5-yl HH Benzofuran-2-yl HH Ph HH 2-Cl-Ph HH 3-Cl-Ph HH 4-Cl-Ph HH 2-F-Ph HH 3-F-Ph HH 4-F-Ph HH 2-Me-Ph HH 3-Me-Ph HH 4-Me-Ph HH 2-MeO-Ph HH 3-MeO-Ph HH 4-MeO-Ph HH 4-Br-Ph HH 2,4-Cl ₂ -Ph H H 3,4-Cl ₂ -Ph H H 2,4,6-Cl ₃ -Ph H H 3,4- (MeO) ₂ -Ph H H 2-Cl-4-Me-Ph H H 2-MeO-4-Me-Ph H H 2,4-Me ₂ -Ph H H 2,5-Me ₂ -Ph H H 2,6-F ₂ -Ph H H 2,3,4,5,6-F _Five -Ph H H 4-Et-Ph H H 4-i-Pr-Ph H H 4-t-Bu-Ph H H 4-CF ₃ -Ph H H 4-i-PrO-Ph H H 4-t-BuO-Ph H H 4-CHF ₂ O-Ph H H 4-CF ₃ O-Ph H H 4-MeS-Ph H H 4-CHO-Ph H H 4-NO ₂ -Ph H H 4-CN-Ph H H 4-PhCH ₂ O-Ph H H 4-MeC (O) -Ph H H 4-PhC (O) -Ph H H 4-MeOCH ₂ -Ph H H 4-MeSCH ₂ -Ph H H 4-MeC (O) O-Ph H H 4-Ph-Ph H H 4-PhO-Ph H H 2,3-Cl ₂ -Ph H H 3,5-Cl ₂ -Ph H H 2,6-Cl ₂ -Ph H H 2,5-Cl ₂ -Ph H H 2,3-F ₂ -Ph H H 2,5-F ₂ -Ph H H 3,4-F ₂ -Ph H H 3,5-F ₂ -Ph H H 2,4-F ₂ -Ph H H 2-CF ₃ -Ph H H 2-F-6-CF ₃ -Ph H H 2-F-6-Cl-Ph H H 2-F-6-Me-Ph H H 2-F-6-MeO-Ph H H 2-F-4-Cl-Ph H H 2-F-4-CF ₃ -Ph HH 2-F-4-Me-Ph HH 2-F-4-MeO-Ph HH 3-F-4-Cl-Ph HH 3-F-4-Me-Ph HH 3-F-4-MeO -Ph HH 4-F-2-Cl-Ph HH 4-F-2-Me-Ph HH 4-F-2-MeO-Ph HH 4-F-3-Cl-Ph HH 4-F-3-Me -Ph HH 4-F-3-MeO-Ph HH 2-OH-Ph HH 4-I-Ph HH 4-MeOC (O) -Ph HH 2,6-Me ₂ -Ph H H 2,6- (MeO) ₂ -Ph H H 3-CF ₃ -Ph H H 2-Br-Ph H H 3-Br-Ph H H 2-MeC (O) -Ph H H 4-c-Pr-Ph H H 4-PhS-Ph H H 2,3-Me ₂ -Ph H H 3,4-Me ₂ -Ph H H 3,5-Me ₂ -Ph H H 2,3- (MeO) ₂ -Ph H H 2,4- (MeO) ₂ -Ph H H 2,5- (MeO) ₂ -Ph H H 3,5- (MeO) ₂ -Ph HH 2-F-4-I-Ph HH 2-F-4-EtO-Ph HH 2-F-6-Ph-Ph HH 3,4-methylenedioxy-Ph HH 3,4-ethylenedioxy-Ph HH 2 -F-4-Br-Ph HH 2-Cl-4-Me-Ph HH 2,4,6-Me ₃ -Ph H -CH = CH-CH = CH- H -CH = N-CH = CH- H -N = CH-CH = CH- H-(CH ₂ ) ₃ -H-(CH ₂ ) _Four -H -CH ₂ -CH ₂ -O-CH ₂ -H -CO- (CH ₂ ) ₃ -H -CH ₂ -CH (CH ₂ Ph) -CH ₂ -H -CH ₂ -CH ₂ -CH (Me) -CH ₂ -H -CH = CH-CH = C (OMe)-H Me HH Me Cl H Me FH Me Br H Me IH Me Me H Me Et H Me n-Pr H Me i-Pr H Me n-Bu H Me i -Bu H Me s-Bu H Me t-Bu H Me n-Pen H Me 3-Me-n-Bu H Me n-Hex H Me Ethenyl H Me 1-Propenyl H Me Ethynyl H Me CF ₃ H Me c-Pr H Me c-Hex H Me MeO H Me t-BuO H Me CF ₃ OH Me MeS H Me MeSO H Me MeSO ₂ H Me NO ₂ H Me NC H Me CHO H Me Me ₂ NH Me PhCH ₂ H Me PhCH = CH H Me 4-Cl-PHCH = CH H Me PhCH = CHCH ₂ H Me PhCC H Me Ph H Me MeNHC (O) H Me PhNHC (O) H Me EtNHC (O) H Me 2-F-PhNHC (O) H Me 3-F-PhNHC (O) H Me 4-F- PhNHC (O) H Me 2-Cl-PhNHC (O) H Me 3-Cl-PhNHC (O) H Me 4-Cl-PhNHC (O) H Me 2-Me-PhNHC (O) H Me 3-Me- PhNHC (O) H Me 4-Me-PhNHC (O) H Me 2-Br-PhNHC (O) H Me 3-Br-PhNHC (O) H Me 4-Br-PhNHC (O) H Me 2-MeO- PhNHC (O) H Me 3-MeO-PhNHC (O) H Me 4-MeO-PhNHC (O) H Me 2,6-F ₂ -PhNHC (O) H Me MeOC (O) H Me MeOCH ₂ H Me MeOC (= NOMe) H Me MeC (= NOMe) H Me MeC (O) H Me CH ₂ SMe H Me CH ₂ SCH ₂ Ph H Me Pyrazol-1-ylCH ₂ H Me ClCH ₂ H Me BrCH ₂ H Me CF ₃ CF ₂ H Me PhC (O) NH H Me 1-Naphthyl H Me 2-Naphthyl H Me 1-Me-Pyrazol-5-yl H Me 1-Me-3-Cl-Pyrazol-5-yl H Me 2-F-Furan -3-yl H Me Oxazol-2-yl H Me 1,2,4-Oxadiazol-3-yl H Me 1,2,4-Thiadizazol-5-yl H Me 1,2,4-Triazol-1-yl H Me 1,2,3-Triazol-1-yl H Me 1,2,3,4-Tetrazol-1-yl H Me 6-MeO-Pyrimidin-2-yl H Me Pyridazin-3-yl H Me 1, 3,5-Triazin-2-yl H Me 1,2,4-Triazin-6-yl H Me 1-Me-Pyrrol-2-yl H Me Furan-2-yl H Me Thiophen-2-yl H Me Thiazol -5-yl H Me 2,4-Me ₂ -Oxazol-5-yl H Me 3-Me-Isothiazol-5-yl H Me Isoxazol-5-yl H Me 1-Me-Imidazol-5-yl H Me 4-Me-1,2,3-Thiadiazol-5 -yl H Me Pyridin-4-yl H Me Quinoxalin-2-yl H Me 6-Cl-Quinoxalin-2-yl H Me 6-F-Quinoxalin-2-yl H Me 1-Me-Indol-3-yl H Me Benzothiazol-2-yl H Me 5-F-Benzothiazol-2-yl H Me 6-F-Benzothiazol-2-yl H Me Quinolin-4-yl H Me Pyrazin-2-yl H Me 4-CClF ₂ -Pyrimidin-5-yl H Me Benzofuran-2-yl H Me Ph H Me 2-Cl-Ph H Me 3-Cl-Ph H Me 4-Cl-Ph H Me 2-F-Ph H Me 3-F- Ph H Me 4-F-Ph H Me 2-Me-Ph H Me 3-Me-Ph H Me 4-Me-Ph H Me 2-MeO-Ph H Me 3-MeO-Ph H Me 4-MeO-Ph H Me 4-Br-Ph H Me 2,4-Cl ₂ -Ph H Me 3,4-Cl ₂ -Ph H Me 2,4,6-Cl ₃ -Ph H Me 3,4- (MeO) ₂ -Ph H Me 2-Cl-4-Me-Ph H Me 2-MeO-4-Me-Ph H Me 2,4-Me ₂ -Ph H Me 2,5-Me ₂ -Ph H Me 2,6-F ₂ -Ph H Me 2,3,4,5,6-F _Five -Ph H Me 4-Et-Ph H Me 4-i-Pr-Ph H Me 4-t-Bu-Ph H Me 4-CF ₃ -Ph H Me 4-i-PrO-Ph H Me 4-t-BuO-Ph H Me 4-CHF ₂ O-Ph H Me 4-CF ₃ O-Ph H Me 4-MeS-Ph H Me 4-CHO-Ph H Me 4-NO ₂ -Ph H Me 4-CN-Ph H Me 4-PhCH ₂ O-Ph H Me 4-MeC (O) -Ph H Me 4-PhC (O) -Ph H Me 4-MeOCH ₂ -Ph H Me 4-MeSCH ₂ -Ph H Me 4-MeC (O) O-Ph H Me 4-Ph-Ph H Me 4-PhO-Ph H Me 2,3-Cl ₂ -Ph H Me 3,5-Cl ₂ -Ph H Me 2,6-Cl ₂ -Ph H Me 2,5-Cl ₂ -Ph H Me 2,3-F ₂ -Ph H Me 2,5-F ₂ -Ph H Me 3,4-F ₂ -Ph H Me 3,5-F ₂ -Ph H Me 2,4-F ₂ -Ph H Me 2-CF ₃ -Ph H Me 2-F-6-CF ₃ -Ph H Me 2-F-6-Cl-Ph H Me 2-F-6-Me-Ph H Me 2-F-6-MeO-Ph H Me 2-F-4-Cl-Ph H Me 2- F-4-CF ₃ -Ph H Me 2-F-4-Me-Ph H Me 2-F-4-MeO-Ph H Me 3-F-4-Cl-Ph H Me 3-F-4-Me-Ph H Me 3- F-4-MeO-Ph H Me 4-F-2-Cl-Ph H Me 4-F-2-Me-Ph H Me 4-F-2-MeO-Ph H Me 4-F-3-Cl- Ph H Me 4-F-3-Me-Ph H Me 4-F-3-MeO-Ph H Me 2-OH-Ph H Me 4-I-Ph H Me 4-MeOC (O) -Ph H Me 2 , 6-Me ₂ -Ph H Me 2,6- (MeO) ₂ -Ph H Me 3-CF ₃ -Ph H Me 2-Br-Ph H Me 3-Br-Ph H Me 2-MeC (O) -Ph H Me 4-c-Pr-Ph H Me 4-PhS-Ph H Me 2,3-Me ₂ -Ph H Me 3,4-Me ₂ -Ph H Me 3,5-Me ₂ -Ph H Me 2,3- (MeO) ₂ -Ph H Me 2,4- (MeO) ₂ -Ph H Me 2,5- (MeO) ₂ -Ph H Me 3,5- (MeO) ₂ -Ph H Me 2-F-4-I-Ph H Me 2-F-4-EtO-Ph H Me 2-F-6-Ph-Ph H Me 3,4-methylenedioxy-Ph H Me 3,4- ethylenedioxy-Ph H Me 2-F-4-Br-Ph H Me 2-Cl-4-Me-Ph H Me 2,4,6-Me ₃ -Ph H Et Et H Et n-Pr H Et i-Pr H Et n-Bu H Et s-Bu H Et t-Bu H Et CF ₃ H Et CF ₂ CF ₃ H Et 1-Naphthyl H Et 2-Naphthyl H Et Ph H Et 2-Cl-Ph H Et 4-Cl-Ph H Et 2-F-Ph H Et 4-F-Ph H Et 2-Me-Ph H Et 3-Me-Ph H Et 4-Me-Ph H Et 2-MeO-Ph H Et 3-MeO-Ph H Et 4-MeO-Ph H Et 4-Br-Ph H Et 2,6-F ₂ -Ph H Et 4-CF ₃ -Ph H Et 4-Ph-Ph H Et 4-PhO-Ph H Et 2,3-F ₂ -Ph H Et 2,5-F ₂ -Ph H Et 3,4-F ₂ -Ph H Et 3,5-F ₂ -Ph H Et 2,4-F ₂ -Ph H Et 2-F-4-Cl-Ph H Et 2-F-4-Me-Ph H Et 2-F-4-MeO-Ph H Et 3-F-4-Cl-Ph H Et 3- F-4-Me-Ph H Et 3-F-4-MeO-Ph H Et 4-F-2-Cl-Ph H Et 4-F-2-Me-Ph H Et 4-F-2-MeO- Ph H Et 4-F-3-Cl-Ph H Et 4-F-3-Me-Ph H Et 4-F-3-MeO-Ph H Et 2,6- (MeO) ₂ -Ph H Et 2-Br-Ph H Et 3-Br-Ph H Et 4-EtO-Ph H Et 2,3-Me ₂ -Ph H Et 3,4-Me ₂ -Ph H Et 3,5-Me ₂ -Ph H Et 2-Cl-3-Me-Ph H Et 2-Cl-4-Me-Ph H Et 3-Cl-4-Me-Ph H Et 4-Cl-2-Me-Ph H Et 4- Cl-3-Me-Ph H Et 2,4,6-Me ₃ -Ph H Pr Et H Pr n-Pr H Pr i-Pr H Pr s-Bu H Pr t-Bu H Pr CF ₃ H Pr CF ₂ CF ₃ H Pr 1-Me-3-Cl-Pyrazol-4-yl H Pr 1-Me-5-Cl-Pyrazol-3-yl H Pr 1-Me-5-Cl-Pyrazol-4-yl H Pr Ph H Pr 2-Cl-Ph H Pr 4-Cl-Ph H Pr 2-F-Ph H Pr 4-F-Ph H Pr 2-Me-Ph H Pr 4-Me-Ph H Pr 4-Br-Ph H Pr 2 , 6-F ₂ -Ph H Pr 2,3-F ₂ -Ph H Pr 2,5-F ₂ -Ph H Pr 3,4-F ₂ -Ph H Pr 3,5-F ₂ -Ph H Pr 2,4-F ₂ -Ph H Pr 2-Br-Ph H Br n-Pr H Br i-Pr H Br s-Bu H Br t-Bu H Br CF ₃ H Br CF ₂ CF ₃ H Br Ph H Br 2-Cl-Ph H Br 4-Cl-Ph H Br 2-F-Ph H Br 4-F-Ph H Br 2-Me-Ph H Br 4-Me-Ph H Br 4-Br -Ph H i-Pr i-Pr H i-Pr s-Bu H i-Pr t-Bu H i-Pr CF ₃ H i-Pr CF ₂ CF ₃ H i-Pr Ph H i-Pr 2-Cl-Ph H i-Pr 4-Cl-Ph H i-Pr 2-F-Ph H i-Pr 4-F-Ph H i-Pr 2-Me-Ph H i-Pr 4-Me-Ph H i-Pr 4-Br-Ph H i-Pr 2-Br-Ph H HH Cl H Cl Cl HF Cl H Br Cl HI Cl H Me Cl H Et Cl H n-Pr Cl H i-Pr Cl H n-Bu Cl H i-Bu Cl H s-Bu Cl H t-Bu Cl H n-Pen Cl H 3-Me-n-Bu Cl H n-Hex Cl H Ethenyl Cl H 1 -Propenyl Cl H Ethynyl Cl H CF ₃ Cl H c-Pr Cl H c-Hex Cl H MeO Cl H t-BuO Cl H CF ₃ O Cl H MeS Cl H MeSO Cl H MeSO ₂ Cl H NO ₂ Cl H NC Cl H CHO Cl H Me ₂ N Cl H PhCH ₂ Cl H PhCH = CH Cl H 4-Cl-PHCH = CH Cl H PhCH = CHCH ₂ Cl H PhCC Cl H Ph Cl H MeNHC (O) Cl H PhNHC (O) Cl H EtNHC (O) Cl H 2-F-PhNHC (O) Cl H 3-F-PhNHC (O) Cl H 4-F- PhNHC (O) Cl H 2-Cl-PhNHC (O) Cl H 3-Cl-PhNHC (O) Cl H 4-Cl-PhNHC (O) Cl H 2-Me-PhNHC (O) Cl H 3-Me- PhNHC (O) Cl H 4-Me-PhNHC (O) Cl H 2-Br-PhNHC (O) Cl H 3-Br-PhNHC (O) Cl H 4-Br-PhNHC (O) Cl H 2-MeO- PhNHC (O) Cl H 3-MeO-PhNHC (O) Cl H 4-MeO-PhNHC (O) Cl H 2,6-F ₂ -PhNHC (O) Cl H MeOC (O) Cl H MeOCH ₂ Cl H MeOC (= NOMe) Cl H MeC (= NOMe) Cl H MeC (O) Cl H CH ₂ SMe Cl H CH ₂ SCH ₂ Ph Cl H Pyrazol-1-ylCH ₂ Cl H ClCH ₂ Cl H BrCH ₂ Cl H CF ₃ CF ₂ Cl H PhC (O) NH Cl H 1-Naphthyl Cl H 2-Naphthyl Cl H 1-Me-Pyrazol-5-yl Cl H 1-Me-3-Cl-Pyrazol-5-yl Cl H 2-F-Furan -3-yl Cl H Oxazol-2-yl Cl H 1,2,4-Oxadiazol-3-yl Cl H 1,2,4-Thiadizazol-5-yl Cl H 1,2,4-Triazol-1-yl Cl H 1,2,3-Triazol-1-yl Cl H 1,2,3,4-Tetrazol-1-yl Cl H 6-MeO-Pyrimidin-2-yl Cl H Pyridazin-3-yl Cl H 1, 3,5-Triazin-2-yl Cl H 1,2,4-Triazin-6-yl Cl H 1-Me-Pyrrol-2-yl Cl H Furan-2-yl Cl H Thiophen-2-yl Cl H Thiazol -5-yl Cl H 2,4-Me ₂ -Oxazol-5-yl Cl H 3-Me-Isothiazol-5-yl Cl H Isoxazol-5-yl Cl H 1-Me-Imidazol-5-yl Cl H 4-Me-1,2,3-Thiadiazol-5 -yl Cl H Pyridin-4-yl Cl H Quinoxalin-2-yl Cl H 6-Cl-Quinoxalin-2-yl Cl H 6-F-Quinoxalin-2-yl Cl H 1-Me-Indol-3-yl Cl H Benzothiazol-2-yl Cl H 5-F-Benzothiazol-2-yl Cl H 6-F-Benzothiazol-2-yl Cl H Quinolin-4-yl Cl H Pyrazin-2-yl Cl H 4-CClF ₂ -Pyrimidin-5-yl Cl H Benzofuran-2-yl Cl H Ph Cl H 2-Cl-Ph Cl H 3-Cl-Ph Cl H 4-Cl-Ph Cl H 2-F-Ph Cl H 3-F- Ph Cl H 4-F-Ph Cl H 2-Me-Ph Cl H 3-Me-Ph Cl H 4-Me-Ph Cl H 2-MeO-Ph Cl H 3-MeO-Ph Cl H 4-MeO-Ph Cl H 4-Br-Ph Cl H 2,4-Cl ₂ -Ph Cl H 3,4-Cl ₂ -Ph Cl H 2,4,6-Cl ₃ -Ph Cl H 3,4- (MeO) ₂ -Ph Cl H 2-Cl-4-Me-Ph Cl H 2-MeO-4-Me-Ph Cl H 2,4-Me ₂ -Ph Cl H 2,5-Me ₂ -Ph Cl H 2,6-F ₂ -Ph Cl H 2,3,4,5,6-F _Five -Ph Cl H 4-Et-Ph Cl H 4-i-Pr-Ph Cl H 4-t-Bu-Ph Cl H 4-CF ₃ -Ph Cl H 4-i-PrO-Ph Cl H 4-t-BuO-Ph Cl H 4-CHF ₂ O-Ph Cl H 4-CF ₃ O-Ph Cl H 4-MeS-Ph Cl H 4-CHO-Ph Cl H 4-NO ₂ -Ph Cl H 4-CN-Ph Cl H 4-PhCH ₂ O-Ph Cl H 4-MeC (O) -Ph Cl H 4-PhC (O) -Ph Cl H 4-MeOCH ₂ -Ph Cl H 4-MeSCH ₂ -Ph Cl H 4-MeC (O) O-Ph Cl H 4-Ph-Ph Cl H 4-PhO-Ph Cl H 2,3-Cl ₂ -Ph Cl H 3,5-Cl ₂ -Ph Cl H 2,6-Cl ₂ -Ph Cl H 2,5-Cl ₂ -Ph Cl H 2,3-F ₂ -Ph Cl H 2,5-F ₂ -Ph Cl H 3,4-F ₂ -Ph Cl H 3,5-F ₂ -Ph Cl H 2,4-F ₂ -Ph Cl H 2-CF ₃ -Ph Cl H 2-F-6-CF ₃ -Ph Cl H 2-F-6-Cl-Ph Cl H 2-F-6-Me-Ph Cl H 2-F-6-MeO-Ph Cl H 2-F-4-Cl-Ph Cl H 2- F-4-CF ₃ -Ph Cl H 2-F-4-Me-Ph Cl H 2-F-4-MeO-Ph Cl H 3-F-4-Cl-Ph Cl H 3-F-4-Me-Ph Cl H 3- F-4-MeO-Ph Cl H 4-F-2-Cl-Ph Cl H 4-F-2-Me-Ph Cl H 4-F-2-MeO-Ph Cl H 4-F-3-Cl- Ph Cl H 4-F-3-Me-Ph Cl H 4-F-3-MeO-Ph Cl H 2-OH-Ph Cl H 4-I-Ph Cl H 4-MeOC (O) -Ph Cl H 2 , 6-Me ₂ -Ph Cl H 2,6- (MeO) ₂ -Ph Cl H 3-CF ₃ -Ph Cl H 2-Br-Ph Cl H 3-Br-Ph Cl H 2-MeC (O) -Ph Cl H 4-c-Pr-Ph Cl H 4-PhS-Ph Cl H 2,3-Me ₂ -Ph Cl H 3,4-Me ₂ -Ph Cl H 3,5-Me ₂ -Ph Cl H 2,3- (MeO) ₂ -Ph Cl H 2,4- (MeO) ₂ -Ph Cl H 2,5- (MeO) ₂ -Ph Cl H 3,5- (MeO) ₂ -Ph Cl H 2-F-4-I-Ph Cl H 2-F-4-EtO-Ph Cl H 2-F-6-Ph-Ph Cl H 3,4-methylenedioxy-Ph Cl H 3,4- ethylenedioxy-Ph Cl H 2-F-4-Br-Ph Cl H 2-Cl-4-Me-Ph Cl H 2,4,6-Me ₃ -Ph Cl -CH = CH-CH = CH- Cl -CH = N-CH = CH- Cl -N = CH-CH = CH- Cl-(CH ₂ ) ₃ -Cl-(CH ₂ ) _Four -Cl -CH ₂ -CH ₂ -O-CH ₂ -Cl -CO- (CH ₂ ) ₃ -Cl -CH ₂ -CH (CH ₂ Ph) -CH ₂ -Cl -CH ₂ -CH ₂ -CH (Me) -CH ₂ -Cl -CH = CH-CH = C (OMe)-Cl Me Cl Cl Me Cl Cl Me F Cl Me Br Cl Me I Cl Me Me Cl Me Et Cl Me n-Pr Cl Me i-Pr Cl Me n-Bu Cl Me i-Bu Cl Me s-Bu Cl Me t-Bu Cl Me n-Pen Cl Me 3-Me-n-Bu Cl Me n-Hex Cl Me Ethenyl Cl Me 1-Propenyl Cl Me Ethynyl Cl Me CF ₃ Cl Me c-Pr Cl Me c-Hex Cl Me MeO Cl Me t-BuO Cl Me CF ₃ O Cl Me MeS Cl Me MeSO Cl Me MeSO ₂ Cl Me NO ₂ Cl Me NC Cl Me CHO Cl Me Me ₂ N Cl Me PhCH ₂ Cl Me PhCH = CH Cl Me 4-Cl-PHCH = CH Cl Me PhCH = CHCH ₂ Cl Me PhCC Cl Me Ph Cl Me MeNHC (O) Cl Me PhNHC (O) Cl Me EtNHC (O) Cl Me 2-F-PhNHC (O) Cl Me 3-F-PhNHC (O) Cl Me 4-F- PhNHC (O) Cl Me 2-Cl-PhNHC (O) Cl Me 3-Cl-PhNHC (O) Cl Me 4-Cl-PhNHC (O) Cl Me 2-Me-PhNHC (O) Cl Me 3-Me- PhNHC (O) Cl Me 4-Me-PhNHC (O) Cl Me 2-Br-PhNHC (O) Cl Me 3-Br-PhNHC (O) Cl Me 4-Br-PhNHC (O) Cl Me 2-MeO- PhNHC (O) Cl Me 3-MeO-PhNHC (O) Cl Me 4-MeO-PhNHC (O) Cl Me 2,6-F ₂ -PhNHC (O) Cl Me MeOC (O) Cl Me MeOCH ₂ Cl Me MeOC (= NOMe) Cl Me MeC (= NOMe) Cl Me MeC (O) Cl Me CH ₂ SMe Cl Me CH ₂ SCH ₂ Ph Cl Me Pyrazol-1-ylCH ₂ Cl Me ClCH ₂ Cl Me BrCH ₂ Cl Me CF ₃ CF ₂ Cl Me PhC (O) NH Cl Me 1-Naphthyl Cl Me 2-Naphthyl Cl Me 1-Me-Pyrazol-5-yl Cl Me 1-Me-3-Cl-Pyrazol-5-yl Cl Me 2-F-Furan -3-yl Cl Me Oxazol-2-yl Cl Me 1,2,4-Oxadiazol-3-yl Cl Me 1,2,4-Thiadizazol-5-yl Cl Me 1,2,4-Triazol-1-yl Cl Me 1,2,3-Triazol-1-yl Cl Me 1,2,3,4-Tetrazol-1-yl Cl Me 6-MeO-Pyrimidin-2-yl Cl Me Pyridazin-3-yl Cl Me 1, 3,5-Triazin-2-yl Cl Me 1,2,4-Triazin-6-yl Cl Me 1-Me-Pyrrol-2-yl Cl Me Furan-2-yl Cl Me Thiophen-2-yl Cl Me Thiazol -5-yl Cl Me 2,4-Me ₂ -Oxazol-5-yl Cl Me 3-Me-Isothiazol-5-yl Cl Me Isoxazol-5-yl Cl Me 1-Me-Imidazol-5-yl Cl Me 4-Me-1,2,3-Thiadiazol-5 -yl Cl Me Pyridin-4-yl Cl Me Quinoxalin-2-yl Cl Me 6-Cl-Quinoxalin-2-yl Cl Me 6-F-Quinoxalin-2-yl Cl Me 1-Me-Indol-3-yl Cl Me Benzothiazol-2-yl Cl Me 5-F-Benzothiazol-2-yl Cl Me 6-F-Benzothiazol-2-yl Cl Me Quinolin-4-yl Cl Me Pyrazin-2-yl Cl Me 4-CClF ₂ -Pyrimidin-5-yl Cl Me Benzofuran-2-yl Cl Me Ph Cl Me 2-Cl-Ph Cl Me 3-Cl-Ph Cl Me 4-Cl-Ph Cl Me 2-F-Ph Cl Me 3-F- Ph Cl Me 4-F-Ph Cl Me 2-Me-Ph Cl Me 3-Me-Ph Cl Me 4-Me-Ph Cl Me 2-MeO-Ph Cl Me 3-MeO-Ph Cl Me 4-MeO-Ph Cl Me 4-Br-Ph Cl Me 2,4-Cl ₂ -Ph Cl Me 3,4-Cl ₂ -Ph Cl Me 2,4,6-Cl ₃ -Ph Cl Me 3,4- (MeO) ₂ -Ph Cl Me 2-Cl-4-Me-Ph Cl Me 2-MeO-4-Me-Ph Cl Me 2,4-Me ₂ -Ph Cl Me 2,5-Me ₂ -Ph Cl Me 2,6-F ₂ -Ph Cl Me 2,3,4,5,6-F _Five -Ph Cl Me 4-Et-Ph Cl Me 4-i-Pr-Ph Cl Me 4-t-Bu-Ph Cl Me 4-CF ₃ -Ph Cl Me 4-i-PrO-Ph Cl Me 4-t-BuO-Ph Cl Me 4-CHF ₂ O-Ph Cl Me 4-CF ₃ O-Ph Cl Me 4-MeS-Ph Cl Me 4-CHO-Ph Cl Me 4-NO ₂ -Ph Cl Me 4-CN-Ph Cl Me 4-PhCH ₂ O-Ph Cl Me 4-MeC (O) -Ph Cl Me 4-PhC (O) -Ph Cl Me 4-MeOCH ₂ -Ph Cl Me 4-MeSCH ₂ -Ph Cl Me 4-MeC (O) O-Ph Cl Me 4-Ph-Ph Cl Me 4-PhO-Ph Cl Me 2,3-Cl ₂ -Ph Cl Me 3,5-Cl ₂ -Ph Cl Me 2,6-Cl ₂ -Ph Cl Me 2,5-Cl ₂ -Ph Cl Me 2,3-F ₂ -Ph Cl Me 2,5-F ₂ -Ph Cl Me 3,4-F ₂ -Ph Cl Me 3,5-F ₂ -Ph Cl Me 2,4-F ₂ -Ph Cl Me 2-CF ₃ -Ph Cl Me 2-F-6-CF ₃ -Ph Cl Me 2-F-6-Cl-Ph Cl Me 2-F-6-Me-Ph Cl Me 2-F-6-MeO-Ph Cl Me 2-F-4-Cl-Ph Cl Me 2- F-4-CF ₃ -Ph Cl Me 2-F-4-Me-Ph Cl Me 2-F-4-MeO-Ph Cl Me 3-F-4-Cl-Ph Cl Me 3-F-4-Me-Ph Cl Me 3- F-4-MeO-Ph Cl Me 4-F-2-Cl-Ph Cl Me 4-F-2-Me-Ph Cl Me 4-F-2-MeO-Ph Cl Me 4-F-3-Cl- Ph Cl Me 4-F-3-Me-Ph Cl Me 4-F-3-MeO-Ph Cl Me 2-OH-Ph Cl Me 4-I-Ph Cl Me 4-MeOC (O) -Ph Cl Me 2 , 6-Me ₂ -Ph Cl Me 2,6- (MeO) ₂ -Ph Cl Me 3-CF ₃ -Ph Cl Me 2-Br-Ph Cl Me 3-Br-Ph Cl Me 2-MeC (O) -Ph Cl Me 4-c-Pr-Ph Cl Me 4-PhS-Ph Cl Me 2,3-Me ₂ -Ph Cl Me 3,4-Me ₂ -Ph Cl Me 3,5-Me ₂ -Ph Cl Me 2,3- (MeO) ₂ -Ph Cl Me 2,4- (MeO) ₂ -Ph Cl Me 2,5- (MeO) ₂ -Ph Cl Me 3,5- (MeO) ₂ -Ph Cl Me 2-F-4-I-Ph Cl Me 2-F-4-EtO-Ph Cl Me 2-F-6-Ph-Ph Cl Me 3,4-methylenedioxy-Ph Cl Me 3,4- ethylenedioxy-Ph Cl Me 2-F-4-Br-Ph Cl Me 2-Cl-4-Me-Ph Cl Me 2,4,6-Me ₃ -Ph Cl Et Et Cl Et n-Pr Cl Et i-Pr Cl Et n-Bu Cl Et s-Bu Cl Et t-Bu Cl Et CF ₃ Cl Et CF ₂ CF ₃ Cl Et 1-Naphthyl Cl Et 2-Naphthyl Cl Et Ph Cl Et 2-Cl-Ph Cl Et 4-Cl-Ph Cl Et 2-F-Ph Cl Et 4-F-Ph Cl Et 2-Me-Ph Cl Et 3-Me-Ph Cl Et 4-Me-Ph Cl Et 2-MeO-Ph Cl Et 3-MeO-Ph Cl Et 4-MeO-Ph Cl Et 4-Br-Ph Cl Et 2,6-F ₂ -Ph Cl Et 4-CF ₃ -Ph Cl Et 4-Ph-Ph Cl Et 4-PhO-Ph Cl Et 2,3-F ₂ -Ph Cl Et 2,5-F ₂ -Ph Cl Et 3,4-F ₂ -Ph Cl Et 3,5-F ₂ -Ph Cl Et 2,4-F ₂ -Ph Cl Et 2-F-4-Cl-Ph Cl Et 2-F-4-Me-Ph Cl Et 2-F-4-MeO-Ph Cl Et 3-F-4-Cl-Ph Cl Et 3- F-4-Me-Ph Cl Et 3-F-4-MeO-Ph Cl Et 4-F-2-Cl-Ph Cl Et 4-F-2-Me-Ph Cl Et 4-F-2-MeO- Ph Cl Et 4-F-3-Cl-Ph Cl Et 4-F-3-Me-Ph Cl Et 4-F-3-MeO-Ph Cl Et 2,6- (MeO) ₂ -Ph Cl Et 2-Br-Ph Cl Et 3-Br-Ph Cl Et 4-EtO-Ph Cl Et 2,3-Me ₂ -Ph Cl Et 3,4-Me ₂ -Ph Cl Et 3,5-Me ₂ -Ph Cl Et 2-Cl-3-Me-Ph Cl Et 2-Cl-4-Me-Ph Cl Et 3-Cl-4-Me-Ph Cl Et 4-Cl-2-Me-Ph Cl Et 4- Cl-3-Me-Ph Cl Et 2,4,6-Me ₃ -Ph Cl Pr Et Cl Pr n-Pr Cl Pr i-Pr Cl Pr s-Bu Cl Pr t-Bu Cl Pr CF ₃ Cl Pr CF ₂ CF ₃ Cl Pr 1-Me-3-Cl-Pyrazol-4-yl Cl Pr 1-Me-5-Cl-Pyrazol-3-yl Cl Pr 1-Me-5-Cl-Pyrazol-4-yl Cl Pr Ph Cl Pr 2-Cl-Ph Cl Pr 4-Cl-Ph Cl Pr 2-F-Ph Cl Pr 4-F-Ph Cl Pr 2-Me-Ph Cl Pr 4-Me-Ph Cl Pr 4-Br-Ph Cl Pr 2 , 6-F ₂ -Ph Cl Pr 2,3-F ₂ -Ph Cl Pr 2,5-F ₂ -Ph Cl Pr 3,4-F ₂ -Ph Cl Pr 3,5-F ₂ -Ph Cl Pr 2,4-F ₂ -Ph Cl Pr 2-Br-Ph Cl Br n-Pr Cl Br i-Pr Cl Br s-Bu Cl Br t-Bu Cl Br CF ₃ Cl Br CF ₂ CF ₃ Cl Br Ph Cl Br 2-Cl-Ph Cl Br 4-Cl-Ph Cl Br 2-F-Ph Cl Br 4-F-Ph Cl Br 2-Me-Ph Cl Br 4-Me-Ph Cl Br 4-Br -Ph Cl i-Pr i-Pr Cl i-Pr s-Bu Cl i-Pr t-Bu Cl i-Pr CF ₃ Cl i-Pr CF ₂ CF ₃ Cl i-Pr Ph Cl i-Pr 2-Cl-Ph Cl i-Pr 4-Cl-Ph Cl i-Pr 2-F-Ph Cl i-Pr 4-F-Ph Cl i-Pr 2-Me-Ph Cl i-Pr 4-Me-Ph Cl i-Pr 4-Br-Ph Cl i-Pr 2-Br-Ph Cl HH Me H Cl Me HF Me H Br Me HI Me H Me Me H Et Me H n-Pr Me H i-Pr Me H n-Bu Me H i-Bu Me H s-Bu Me H t-Bu Me H n-Pen Me H 3-Me-n-Bu Me H n-Hex Me H Ethenyl Me H 1 -Propenyl Me H Ethynyl Me H CF ₃ Me H c-Pr Me H c-Hex Me H MeO Me H t-BuO Me H CF ₃ O Me H MeS Me H MeSO Me H MeSO ₂ Me H NO ₂ Me H NC Me H CHO Me H Me ₂ N Me H PhCH ₂ Me H PhCH = CH Me H 4-Cl-PHCH = CH Me H PhCH = CHCH ₂ Me H PhCC Me H Ph Me H MeNHC (O) Me H PhNHC (O) Me H EtNHC (O) Me H 2-F-PhNHC (O) Me H 3-F-PhNHC (O) Me H 4-F- PhNHC (O) Me H 2-Cl-PhNHC (O) Me H 3-Cl-PhNHC (O) Me H 4-Cl-PhNHC (O) Me H 2-Me-PhNHC (O) Me H 3-Me- PhNHC (O) Me H 4-Me-PhNHC (O) Me H 2-Br-PhNHC (O) Me H 3-Br-PhNHC (O) Me H 4-Br-PhNHC (O) Me H 2-MeO- PhNHC (O) Me H 3-MeO-PhNHC (O) Me H 4-MeO-PhNHC (O) Me H 2,6-F ₂ -PhNHC (O) Me H MeOC (O) Me H MeOCH ₂ Me H MeOC (= NOMe) Me H MeC (= NOMe) Me H MeC (O) Me H CH ₂ SMe Me H CH ₂ SCH ₂ Ph Me H Pyrazol-1-ylCH ₂ Me H ClCH ₂ Me H BrCH ₂ Me H CF ₃ CF ₂ Me H PhC (O) NH Me H 1-Naphthyl Me H 2-Naphthyl Me H 1-Me-Pyrazol-5-yl Me H 1-Me-3-Cl-Pyrazol-5-yl Me H 2-F-Furan -3-yl Me H Oxazol-2-yl Me H 1,2,4-Oxadiazol-3-yl Me H 1,2,4-Thiadizazol-5-yl Me H 1,2,4-Triazol-1-yl Me H 1,2,3-Triazol-1-yl Me H 1,2,3,4-Tetrazol-1-yl Me H 6-MeO-Pyrimidin-2-yl Me H Pyridazin-3-yl Me H 1, 3,5-Triazin-2-yl Me H 1,2,4-Triazin-6-yl Me H 1-Me-Pyrrol-2-yl Me H Furan-2-yl Me H Thiophen-2-yl Me H Thiazol -5-yl Me H 2,4-Me ₂ -Oxazol-5-yl Me H 3-Me-Isothiazol-5-yl Me H Isoxazol-5-yl Me H 1-Me-Imidazol-5-yl Me H 4-Me-1,2,3-Thiadiazol-5 -yl Me H Pyridin-4-yl Me H Quinoxalin-2-yl Me H 6-Cl-Quinoxalin-2-yl Me H 6-F-Quinoxalin-2-yl Me H 1-Me-Indol-3-yl Me H Benzothiazol-2-yl Me H 5-F-Benzothiazol-2-yl Me H 6-F-Benzothiazol-2-yl Me H Quinolin-4-yl Me H Pyrazin-2-yl Me H 4-CClF ₂ -Pyrimidin-5-yl Me H Benzofuran-2-yl Me H Ph Me H 2-Cl-Ph Me H 3-Cl-Ph Me H 4-Cl-Ph Me H 2-F-Ph Me H 3-F- Ph Me H 4-F-Ph Me H 2-Me-Ph Me H 3-Me-Ph Me H 4-Me-Ph Me H 2-MeO-Ph Me H 3-MeO-Ph Me H 4-MeO-Ph Me H 4-Br-Ph Me H 2,4-Cl ₂ -Ph Me H 3,4-Cl ₂ -Ph Me H 2,4,6-Cl ₃ -Ph Me H 3,4- (MeO) ₂ -Ph Me H 2-Cl-4-Me-Ph Me H 2-MeO-4-Me-Ph Me H 2,4-Me ₂ -Ph Me H 2,5-Me ₂ -Ph Me H 2,6-F ₂ -Ph Me H 2,3,4,5,6-F _Five -Ph Me H 4-Et-Ph Me H 4-i-Pr-Ph Me H 4-t-Bu-Ph Me H 4-CF ₃ -Ph Me H 4-i-PrO-Ph Me H 4-t-BuO-Ph Me H 4-CHF ₂ O-Ph Me H 4-CF ₃ O-Ph Me H 4-MeS-Ph Me H 4-CHO-Ph Me H 4-NO ₂ -Ph Me H 4-CN-Ph Me H 4-PhCH ₂ O-Ph Me H 4-MeC (O) -Ph Me H 4-PhC (O) -Ph Me H 4-MeOCH ₂ -Ph Me H 4-MeSCH ₂ -Ph Me H 4-MeC (O) O-Ph Me H 4-Ph-Ph Me H 4-PhO-Ph Me H 2,3-Cl ₂ -Ph Me H 3,5-Cl ₂ -Ph Me H 2,6-Cl ₂ -Ph Me H 2,5-Cl ₂ -Ph Me H 2,3-F ₂ -Ph Me H 2,5-F ₂ -Ph Me H 3,4-F ₂ -Ph Me H 3,5-F ₂ -Ph Me H 2,4-F ₂ -Ph Me H 2-CF ₃ -Ph Me H 2-F-6-CF ₃ -Ph Me H 2-F-6-Cl-Ph Me H 2-F-6-Me-Ph Me H 2-F-6-MeO-Ph Me H 2-F-4-Cl-Ph Me H 2- F-4-CF ₃ -Ph Me H 2-F-4-Me-Ph Me H 2-F-4-MeO-Ph Me H 3-F-4-Cl-Ph Me H 3-F-4-Me-Ph Me H 3- F-4-MeO-Ph Me H 4-F-2-Cl-Ph Me H 4-F-2-Me-Ph Me H 4-F-2-MeO-Ph Me H 4-F-3-Cl- Ph Me H 4-F-3-Me-Ph Me H 4-F-3-MeO-Ph Me H 2-OH-Ph Me H 4-I-Ph Me H 4-MeOC (O) -Ph Me H 2 , 6-Me ₂ -Ph Me H 2,6- (MeO) ₂ -Ph Me H 3-CF ₃ -Ph Me H 2-Br-Ph Me H 3-Br-Ph Me H 2-MeC (O) -Ph Me H 4-c-Pr-Ph Me H 4-PhS-Ph Me H 2,3-Me ₂ -Ph Me H 3,4-Me ₂ -Ph Me H 3,5-Me ₂ -Ph Me H 2,3- (MeO) ₂ -Ph Me H 2,4- (MeO) ₂ -Ph Me H 2,5- (MeO) ₂ -Ph Me H 3,5- (MeO) ₂ -Ph Me H 2-F-4-I-Ph Me H 2-F-4-EtO-Ph Me H 2-F-6-Ph-Ph Me H 3,4-methylenedioxy-Ph Me H 3,4- ethylenedioxy-Ph Me H 2-F-4-Br-Ph Me H 2-Cl-4-Me-Ph Me H 2,4,6-Me ₃ -Ph Me -CH = CH-CH = CH- Me -CH = N-CH = CH- Me -N = CH-CH = CH- Me-(CH ₂ ) ₃ -Me-(CH ₂ ) _Four -Me -CH ₂ -CH ₂ -O-CH ₂ -Me -CO- (CH ₂ ) ₃ -Me -CH ₂ -CH (CH ₂ Ph) -CH ₂ -Me -CH ₂ -CH ₂ -CH (Me) -CH ₂ -Me -CH = CH-CH = C (OMe)-Me Me Cl Me Me Cl Me Me F Me Me Br Me Me I Me Me Me Me Me Et Me Me n-Pr Me Me i-Pr Me Me n-Bu Me Me i-Bu Me Me s-Bu Me Me t-Bu Me Me n-Pen Me Me 3-Me-n-Bu Me Me n-Hex Me Me Ethenyl Me Me 1-Propenyl Me Me Ethynyl Me Me CF ₃ Me Me c-Pr Me Me c-Hex Me Me MeO Me Me t-BuO Me Me CF ₃ O Me Me MeS Me Me MeSO Me Me MeSO ₂ Me Me NO ₂ Me Me NC Me Me CHO Me Me Me ₂ N Me Me PhCH ₂ Me Me PhCH = CH Me Me 4-Cl-PHCH = CH Me Me PhCH = CHCH ₂ Me Me PhCC Me Me Ph Me Me MeNHC (O) Me Me PhNHC (O) Me Me EtNHC (O) Me Me 2-F-PhNHC (O) Me Me 3-F-PhNHC (O) Me Me 4-F- PhNHC (O) Me Me 2-Cl-PhNHC (O) Me Me 3-Cl-PhNHC (O) Me Me 4-Cl-PhNHC (O) Me Me 2-Me-PhNHC (O) Me Me 3-Me- PhNHC (O) Me Me 4-Me-PhNHC (O) Me Me 2-Br-PhNHC (O) Me Me 3-Br-PhNHC (O) Me Me 4-Br-PhNHC (O) Me Me 2-MeO- PhNHC (O) Me Me 3-MeO-PhNHC (O) Me Me 4-MeO-PhNHC (O) Me Me 2,6-F ₂ -PhNHC (O) Me Me MeOC (O) Me Me MeOCH ₂ Me Me MeOC (= NOMe) Me Me MeC (= NOMe) Me Me MeC (O) Me Me CH ₂ SMe Me Me CH ₂ SCH ₂ Ph Me Me Pyrazol-1-ylCH ₂ Me Me ClCH ₂ Me Me BrCH ₂ Me Me CF ₃ CF ₂ Me Me PhC (O) NH Me Me 1-Naphthyl Me Me 2-Naphthyl Me Me 1-Me-Pyrazol-5-yl Me Me 1-Me-3-Cl-Pyrazol-5-yl Me Me 2-F-Furan -3-yl Me Me Oxazol-2-yl Me Me 1,2,4-Oxadiazol-3-yl Me Me 1,2,4-Thiadizazol-5-yl Me Me 1,2,4-Triazol-1-yl Me Me 1,2,3-Triazol-1-yl Me Me 1,2,3,4-Tetrazol-1-yl Me Me 6-MeO-Pyrimidin-2-yl Me Me Pyridazin-3-yl Me Me 1, 3,5-Triazin-2-yl Me Me 1,2,4-Triazin-6-yl Me Me 1-Me-Pyrrol-2-yl Me Me Furan-2-yl Me Me Thiophen-2-yl Me Me Thiazol -5-yl Me Me 2,4-Me ₂ -Oxazol-5-yl Me Me 3-Me-Isothiazol-5-yl Me Me Isoxazol-5-yl Me Me 1-Me-Imidazol-5-yl Me Me 4-Me-1,2,3-Thiadiazol-5 -yl Me Me Pyridin-4-yl Me Me Quinoxalin-2-yl Me Me 6-Cl-Quinoxalin-2-yl Me Me 6-F-Quinoxalin-2-yl Me Me 1-Me-Indol-3-yl Me Me Benzothiazol-2-yl Me Me 5-F-Benzothiazol-2-yl Me Me 6-F-Benzothiazol-2-yl Me Me Quinolin-4-yl Me Me Pyrazin-2-yl Me Me 4-CClF ₂ -Pyrimidin-5-yl Me Me Benzofuran-2-yl Me Me Ph Me Me 2-Cl-Ph Me Me 3-Cl-Ph Me Me 4-Cl-Ph Me Me 2-F-Ph Me Me 3-F- Ph Me Me 4-F-Ph Me Me 2-Me-Ph Me Me 3-Me-Ph Me Me 4-Me-Ph Me Me 2-MeO-Ph Me Me 3-MeO-Ph Me Me 4-MeO-Ph Me Me 4-Br-Ph Me Me 2,4-Cl ₂ -Ph Me Me 3,4-Cl ₂ -Ph Me Me 2,4,6-Cl ₃ -Ph Me Me 3,4- (MeO) ₂ -Ph Me Me 2-Cl-4-Me-Ph Me Me 2-MeO-4-Me-Ph Me Me 2,4-Me ₂ -Ph Me Me 2,5-Me ₂ -Ph Me Me 2,6-F ₂ -Ph Me Me 2,3,4,5,6-F _Five -Ph Me Me 4-Et-Ph Me Me 4-i-Pr-Ph Me Me 4-t-Bu-Ph Me Me 4-CF ₃ -Ph Me Me 4-i-PrO-Ph Me Me 4-t-BuO-Ph Me Me 4-CHF ₂ O-Ph Me Me 4-CF ₃ O-Ph Me Me 4-MeS-Ph Me Me 4-CHO-Ph Me Me 4-NO ₂ -Ph Me Me 4-CN-Ph Me Me 4-PhCH ₂ O-Ph Me Me 4-MeC (O) -Ph Me Me 4-PhC (O) -Ph Me Me 4-MeOCH ₂ -Ph Me Me 4-MeSCH ₂ -Ph Me Me 4-MeC (O) O-Ph Me Me 4-Ph-Ph Me Me 4-PhO-Ph Me Me 2,3-Cl ₂ -Ph Me Me 3,5-Cl ₂ -Ph Me Me 2,6-Cl ₂ -Ph Me Me 2,5-Cl ₂ -Ph Me Me 2,3-F ₂ -Ph Me Me 2,5-F ₂ -Ph Me Me 3,4-F ₂ -Ph Me Me 3,5-F ₂ -Ph Me Me 2,4-F ₂ -Ph Me Me 2-CF ₃ -Ph Me Me 2-F-6-CF ₃ -Ph Me Me 2-F-6-Cl-Ph Me Me 2-F-6-Me-Ph Me Me 2-F-6-MeO-Ph Me Me 2-F-4-Cl-Ph Me Me 2- F-4-CF ₃ -Ph Me Me 2-F-4-Me-Ph Me Me 2-F-4-MeO-Ph Me Me 3-F-4-Cl-Ph Me Me 3-F-4-Me-Ph Me Me 3- F-4-MeO-Ph Me Me 4-F-2-Cl-Ph Me Me 4-F-2-Me-Ph Me Me 4-F-2-MeO-Ph Me Me 4-F-3-Cl- Ph Me Me 4-F-3-Me-Ph Me Me 4-F-3-MeO-Ph Me Me 2-OH-Ph Me Me 4-I-Ph Me Me 4-MeOC (O) -Ph Me Me 2 , 6-Me ₂ -Ph Me Me 2,6- (MeO) ₂ -Ph Me Me 3-CF ₃ -Ph Me Me 2-Br-Ph Me Me 3-Br-Ph Me Me 2-MeC (O) -Ph Me Me 4-c-Pr-Ph Me Me 4-PhS-Ph Me Me 2,3-Me ₂ -Ph Me Me 3,4-Me ₂ -Ph Me Me 3,5-Me ₂ -Ph Me Me 2,3- (MeO) ₂ -Ph Me Me 2,4- (MeO) ₂ -Ph Me Me 2,5- (MeO) ₂ -Ph Me Me 3,5- (MeO) ₂ -Ph Me Me 2-F-4-I-Ph Me Me 2-F-4-EtO-Ph Me Me 2-F-6-Ph-Ph Me Me 3,4-methylenedioxy-Ph Me Me 3,4- ethylenedioxy-Ph Me Me 2-F-4-Br-Ph Me Me 2-Cl-4-Me-Ph Me Me 2,4,6-Me ₃ -Ph Me Et Et Me Et n-Pr Me Et i-Pr Me Et n-Bu Me Et s-Bu Me Et t-Bu Me Et CF ₃ Me Et CF ₂ CF ₃ Me Et 1-Naphthyl Me Et 2-Naphthyl Me Et Ph Me Et 2-Cl-Ph Me Et 4-Cl-Ph Me Et 2-F-Ph Me Et 4-F-Ph Me Et 2-Me-Ph Me Et 3-Me-Ph Me Et 4-Me-Ph Me Et 2-MeO-Ph Me Et 3-MeO-Ph Me Et 4-MeO-Ph Me Et 4-Br-Ph Me Et 2,6-F ₂ -Ph Me Et 4-CF ₃ -Ph Me Et 4-Ph-Ph Me Et 4-PhO-Ph Me Et 2,3-F ₂ -Ph Me Et 2,5-F ₂ -Ph Me Et 3,4-F ₂ -Ph Me Et 3,5-F ₂ -Ph Me Et 2,4-F ₂ -Ph Me Et 2-F-4-Cl-Ph Me Et 2-F-4-Me-Ph Me Et 2-F-4-MeO-Ph Me Et 3-F-4-Cl-Ph Me Et 3- F-4-Me-Ph Me Et 3-F-4-MeO-Ph Me Et 4-F-2-Cl-Ph Me Et 4-F-2-Me-Ph Me Et 4-F-2-MeO- Ph Me Et 4-F-3-Cl-Ph Me Et 4-F-3-Me-Ph Me Et 4-F-3-MeO-Ph Me Et 2,6- (MeO) ₂ -Ph Me Et 2-Br-Ph Me Et 3-Br-Ph Me Et 4-EtO-Ph Me Et 2,3-Me ₂ -Ph Me Et 3,4-Me ₂ -Ph Me Et 3,5-Me ₂ -Ph Me Et 2-Cl-3-Me-Ph Me Et 2-Cl-4-Me-Ph Me Et 3-Cl-4-Me-Ph Me Et 4-Cl-2-Me-Ph Me Et 4- Cl-3-Me-Ph Me Et 2,4,6-Me ₃ -Ph Me Pr Et Me Pr n-Pr Me Pr i-Pr Me Pr s-Bu Me Pr t-Bu Me Pr CF ₃ Me Pr CF ₂ CF ₃ Me Pr 1-Me-3-Cl-Pyrazol-4-yl Me Pr 1-Me-5-Cl-Pyrazol-3-yl Me Pr 1-Me-5-Cl-Pyrazol-4-yl Me Pr Ph Me Pr 2-Cl-Ph Me Pr 4-Cl-Ph Me Pr 2-F-Ph Me Pr 4-F-Ph Me Pr 2-Me-Ph Me Pr 4-Me-Ph Me Pr 4-Br-Ph Me Pr 2 , 6-F ₂ -Ph Me Pr 2,3-F ₂ -Ph Me Pr 2,5-F ₂ -Ph Me Pr 3,4-F ₂ -Ph Me Pr 3,5-F ₂ -Ph Me Pr 2,4-F ₂ -Ph Me Pr 2-Br-Ph Me Br n-Pr Me Br i-Pr Me Br s-Bu Me Br t-Bu Me Br CF ₃ Me Br CF ₂ CF ₃ Me Br Ph Me Br 2-Cl-Ph Me Br 4-Cl-Ph Me Br 2-F-Ph Me Br 4-F-Ph Me Br 2-Me-Ph Me Br 4-Me-Ph Me Br 4-Br -Ph Me i-Pr i-Pr Me i-Pr s-Bu Me i-Pr t-Bu Me i-Pr CF ₃ Me i-Pr CF ₂ CF ₃ Me i-Pr Ph Me i-Pr 2-Cl-Ph Me i-Pr 4-Cl-Ph Me i-Pr 2-F-Ph Me i-Pr 4-F-Ph Me i-Pr 2-Me-Ph Me i-Pr 4-Me-Ph Me i-Pr 4-Br-Ph Me i-Pr 2-Br-Ph Me HH CF ₃ H Cl CF ₃ HF CF ₃ H Br CF ₃ HI CF ₃ H Me CF ₃ H Et CF ₃ H n-Pr CF ₃ H i-Pr CF ₃ H n-Bu CF ₃ H i-Bu CF ₃ H s-Bu CF ₃ H t-Bu CF ₃ H n-Pen CF ₃ H 3-Me-n-Bu CF ₃ H n-Hex CF ₃ H Ethenyl CF ₃ H 1-Propenyl CF ₃ H Ethynyl CF ₃ H CF ₃ CF ₃ H c-Pr CF ₃ H c-Hex CF ₃ H MeO CF ₃ H t-BuO CF ₃ H CF ₃ O CF ₃ H MeS CF ₃ H MeSO CF ₃ H MeSO ₂ CF ₃ H NO ₂ CF ₃ H NC CF ₃ H CHO CF ₃ H Me ₂ N CF ₃ H PhCH ₂ CF ₃ H PhCH = CH CF ₃ H 4-Cl-PHCH = CH CF ₃ H PhCH = CHCH ₂ CF ₃ H PhCC CF ₃ H Ph CF ₃ H MeNHC (O) CF ₃ H PhNHC (O) CF ₃ H EtNHC (O) CF ₃ H 2-F-PhNHC (O) CF ₃ H 3-F-PhNHC (O) CF ₃ H 4-F-PhNHC (O) CF ₃ H 2-Cl-PhNHC (O) CF ₃ H 3-Cl-PhNHC (O) CF ₃ H 4-Cl-PhNHC (O) CF ₃ H 2-Me-PhNHC (O) CF ₃ H 3-Me-PhNHC (O) CF ₃ H 4-Me-PhNHC (O) CF ₃ H 2-Br-PhNHC (O) CF ₃ H 3-Br-PhNHC (O) CF ₃ H 4-Br-PhNHC (O) CF ₃ H 2-MeO-PhNHC (O) CF ₃ H 3-MeO-PhNHC (O) CF ₃ H 4-MeO-PhNHC (O) CF ₃ H 2,6-F ₂ -PhNHC (O) CF ₃ H MeOC (O) CF ₃ H MeOCH ₂ CF ₃ H MeOC (= NOMe) CF ₃ H MeC (= NOMe) CF ₃ H MeC (O) CF ₃ H CH ₂ SMe CF ₃ H CH ₂ SCH ₂ Ph CF ₃ H Pyrazol-1-ylCH ₂ CF ₃ H ClCH ₂ CF ₃ H BrCH ₂ CF ₃ H CF ₃ CF ₂ CF ₃ H PhC (O) NH CF ₃ H 1-Naphthyl CF ₃ H 2-Naphthyl CF ₃ H 1-Me-Pyrazol-5-yl CF ₃ H 1-Me-3-Cl-Pyrazol-5-yl CF ₃ H 2-F-Furan-3-yl CF ₃ H Oxazol-2-yl CF ₃ H 1,2,4-Oxadiazol-3-yl CF ₃ H 1,2,4-Thiadizazol-5-yl CF ₃ H 1,2,4-Triazol-1-yl CF ₃ H 1,2,3-Triazol-1-yl CF ₃ H 1,2,3,4-Tetrazol-1-yl CF ₃ H 6-MeO-Pyrimidin-2-yl CF ₃ H Pyridazin-3-yl CF ₃ H 1,3,5-Triazin-2-yl CF ₃ H 1,2,4-Triazin-6-yl CF ₃ H 1-Me-Pyrrol-2-yl CF ₃ H Furan-2-yl CF ₃ H Thiophen-2-yl CF ₃ H Thiazol-5-yl CF ₃ H 2,4-Me ₂ -Oxazol-5-yl CF ₃ H 3-Me-Isothiazol-5-yl CF ₃ H Isoxazol-5-yl CF ₃ H 1-Me-Imidazol-5-yl CF ₃ H 4-Me-1,2,3-Thiadiazol-5-yl CF ₃ H Pyridin-4-yl CF ₃ H Quinoxalin-2-yl CF ₃ H 6-Cl-Quinoxalin-2-yl CF ₃ H 6-F-Quinoxalin-2-yl CF ₃ H 1-Me-Indol-3-yl CF ₃ H Benzothiazol-2-yl CF ₃ H 5-F-Benzothiazol-2-yl CF ₃ H 6-F-Benzothiazol-2-yl CF ₃ H Quinolin-4-yl CF ₃ H Pyrazin-2-yl CF ₃ H 4-CClF ₂ -Pyrimidin-5-yl CF ₃ H Benzofuran-2-yl CF ₃ H Ph CF ₃ H 2-Cl-Ph CF ₃ H 3-Cl-Ph CF ₃ H 4-Cl-Ph CF ₃ H 2-F-Ph CF ₃ H 3-F-Ph CF ₃ H 4-F-Ph CF ₃ H 2-Me-Ph CF ₃ H 3-Me-Ph CF ₃ H 4-Me-Ph CF ₃ H 2-MeO-Ph CF ₃ H 3-MeO-Ph CF ₃ H 4-MeO-Ph CF ₃ H 4-Br-Ph CF ₃ H 2,4-Cl ₂ -Ph CF ₃ H 3,4-Cl ₂ -Ph CF ₃ H 2,4,6-Cl ₃ -Ph CF ₃ H 3,4- (MeO) ₂ -Ph CF ₃ H 2-Cl-4-Me-Ph CF ₃ H 2-MeO-4-Me-Ph CF ₃ H 2,4-Me ₂ -Ph CF ₃ H 2,5-Me ₂ -Ph CF ₃ H 2,6-F ₂ -Ph CF ₃ H 2,3,4,5,6-F _Five -Ph CF ₃ H 4-Et-Ph CF ₃ H 4-i-Pr-Ph CF ₃ H 4-t-Bu-Ph CF ₃ H 4-CF ₃ -Ph CF ₃ H 4-i-PrO-Ph CF ₃ H 4-t-BuO-Ph CF ₃ H 4-CHF ₂ O-Ph CF ₃ H 4-CF ₃ O-Ph CF ₃ H 4-MeS-Ph CF ₃ H 4-CHO-Ph CF ₃ H 4-NO ₂ -Ph CF ₃ H 4-CN-Ph CF ₃ H 4-PhCH ₂ O-Ph CF ₃ H 4-MeC (O) -Ph CF ₃ H 4-PhC (O) -Ph CF ₃ H 4-MeOCH ₂ -Ph CF ₃ H 4-MeSCH ₂ -Ph CF ₃ H 4-MeC (O) O-Ph CF ₃ H 4-Ph-Ph CF ₃ H 4-PhO-Ph CF ₃ H 2,3-Cl ₂ -Ph CF ₃ H 3,5-Cl ₂ -Ph CF ₃ H 2,6-Cl ₂ -Ph CF ₃ H 2,5-Cl ₂ -Ph CF ₃ H 2,3-F ₂ -Ph CF ₃ H 2,5-F ₂ -Ph CF ₃ H 3,4-F ₂ -Ph CF ₃ H 3,5-F ₂ -Ph CF ₃ H 2,4-F ₂ -Ph CF ₃ H 2-CF ₃ -Ph CF ₃ H 2-F-6-CF ₃ -Ph CF ₃ H 2-F-6-Cl-Ph CF ₃ H 2-F-6-Me-Ph CF ₃ H 2-F-6-MeO-Ph CF ₃ H 2-F-4-Cl-Ph CF ₃ H 2-F-4-CF ₃ -Ph CF ₃ H 2-F-4-Me-Ph CF ₃ H 2-F-4-MeO-Ph CF ₃ H 3-F-4-Cl-Ph CF ₃ H 3-F-4-Me-Ph CF ₃ H 3-F-4-MeO-Ph CF ₃ H 4-F-2-Cl-Ph CF ₃ H 4-F-2-Me-Ph CF ₃ H 4-F-2-MeO-Ph CF ₃ H 4-F-3-Cl-Ph CF ₃ H 4-F-3-Me-Ph CF ₃ H 4-F-3-MeO-Ph CF ₃ H 2-OH-Ph CF ₃ H 4-I-Ph CF ₃ H 4-MeOC (O) -Ph CF ₃ H 2,6-Me ₂ -Ph CF ₃ H 2,6- (MeO) ₂ -Ph CF ₃ H 3-CF ₃ -Ph CF ₃ H 2-Br-Ph CF ₃ H 3-Br-Ph CF ₃ H 2-MeC (O) -Ph CF ₃ H 4-c-Pr-Ph CF ₃ H 4-PhS-Ph CF ₃ H 2,3-Me ₂ -Ph CF ₃ H 3,4-Me ₂ -Ph CF ₃ H 3,5-Me ₂ -Ph CF ₃ H 2,3- (MeO) ₂ -Ph CF ₃ H 2,4- (MeO) ₂ -Ph CF ₃ H 2,5- (MeO) ₂ -Ph CF ₃ H 3,5- (MeO) ₂ -Ph CF ₃ H 2-F-4-I-Ph CF ₃ H 2-F-4-EtO-Ph CF ₃ H 2-F-6-Ph-Ph CF ₃ H 3,4-methylenedioxy-Ph CF ₃ H 3,4-ethylenedioxy-Ph CF ₃ H 2-F-4-Br-Ph CF ₃ H 2-Cl-4-Me-Ph CF ₃ H 2,4,6-Me ₃ -Ph CF ₃ -CH = CH-CH = CH- CF ₃ -CH = N-CH = CH- CF ₃ -N = CH-CH = CH- CF ₃ -(CH ₂ ) ₃ -CF ₃ -(CH ₂ ) _Four -CF ₃ -CH ₂ -CH ₂ -O-CH ₂ -CF ₃ -CO- (CH ₂ ) ₃ -CF ₃ -CH ₂ -CH (CH ₂ Ph) -CH ₂ -CF ₃ -CH ₂ -CH ₂ -CH (Me) -CH ₂ -CF ₃ -CH = CH-CH = C (OMe)-CF ₃ Me Cl CF ₃ Me Cl CF ₃ Me F CF ₃ Me Br CF ₃ Me I CF ₃ Me Me CF ₃ Me Et CF ₃ Me n-Pr CF ₃ Me i-Pr CF ₃ Me n-Bu CF ₃ Me i-Bu CF ₃ Me s-Bu CF ₃ Me t-Bu CF ₃ Me n-Pen CF ₃ Me 3-Me-n-Bu CF ₃ Me n-Hex CF ₃ Me Ethenyl CF ₃ Me 1-Propenyl CF ₃ Me Ethynyl CF ₃ Me CF ₃ CF ₃ Me c-Pr CF ₃ Me c-Hex CF ₃ Me MeO CF ₃ Me t-BuO CF ₃ Me CF ₃ O CF ₃ Me MeS CF ₃ Me MeSO CF ₃ Me MeSO ₂ CF ₃ Me NO ₂ CF ₃ Me NC CF ₃ Me CHO CF ₃ Me Me ₂ N CF ₃ Me PhCH ₂ CF ₃ Me PhCH = CH CF ₃ Me 4-Cl-PHCH = CH CF ₃ Me PhCH = CHCH ₂ CF ₃ Me PhCC CF ₃ Me Ph CF ₃ Me MeNHC (O) CF ₃ Me PhNHC (O) CF ₃ Me EtNHC (O) CF ₃ Me 2-F-PhNHC (O) CF ₃ Me 3-F-PhNHC (O) CF ₃ Me 4-F-PhNHC (O) CF ₃ Me 2-Cl-PhNHC (O) CF ₃ Me 3-Cl-PhNHC (O) CF ₃ Me 4-Cl-PhNHC (O) CF ₃ Me 2-Me-PhNHC (O) CF ₃ Me 3-Me-PhNHC (O) CF ₃ Me 4-Me-PhNHC (O) CF ₃ Me 2-Br-PhNHC (O) CF ₃ Me 3-Br-PhNHC (O) CF ₃ Me 4-Br-PhNHC (O) CF ₃ Me 2-MeO-PhNHC (O) CF ₃ Me 3-MeO-PhNHC (O) CF ₃ Me 4-MeO-PhNHC (O) CF ₃ Me 2,6-F ₂ -PhNHC (O) CF ₃ Me MeOC (O) CF ₃ Me MeOCH ₂ CF ₃ Me MeOC (= NOMe) CF ₃ Me MeC (= NOMe) CF ₃ Me MeC (O) CF ₃ Me CH ₂ SMe CF ₃ Me CH ₂ SCH ₂ Ph CF ₃ Me Pyrazol-1-ylCH ₂ CF ₃ Me ClCH ₂ CF ₃ Me BrCH ₂ CF ₃ Me CF ₃ CF ₂ CF ₃ Me PhC (O) NH CF ₃ Me 1-Naphthyl CF ₃ Me 2-Naphthyl CF ₃ Me 1-Me-Pyrazol-5-yl CF ₃ Me 1-Me-3-Cl-Pyrazol-5-yl CF ₃ Me 2-F-Furan-3-yl CF ₃ Me Oxazol-2-yl CF ₃ Me 1,2,4-Oxadiazol-3-yl CF ₃ Me 1,2,4-Thiadizazol-5-yl CF ₃ Me 1,2,4-Triazol-1-yl CF ₃ Me 1,2,3-Triazol-1-yl CF ₃ Me 1,2,3,4-Tetrazol-1-yl CF ₃ Me 6-MeO-Pyrimidin-2-yl CF ₃ Me Pyridazin-3-yl CF ₃ Me 1,3,5-Triazin-2-yl CF ₃ Me 1,2,4-Triazin-6-yl CF ₃ Me 1-Me-Pyrrol-2-yl CF ₃ Me Furan-2-yl CF ₃ Me Thiophen-2-yl CF ₃ Me Thiazol-5-yl CF ₃ Me 2,4-Me ₂ -Oxazol-5-yl CF ₃ Me 3-Me-Isothiazol-5-yl CF ₃ Me Isoxazol-5-yl CF ₃ Me 1-Me-Imidazol-5-yl CF ₃ Me 4-Me-1,2,3-Thiadiazol-5-yl CF ₃ Me Pyridin-4-yl CF ₃ Me Quinoxalin-2-yl CF ₃ Me 6-Cl-Quinoxalin-2-yl CF ₃ Me 6-F-Quinoxalin-2-yl CF ₃ Me 1-Me-Indol-3-yl CF ₃ Me Benzothiazol-2-yl CF ₃ Me 5-F-Benzothiazol-2-yl CF ₃ Me 6-F-Benzothiazol-2-yl CF ₃ Me Quinolin-4-yl CF ₃ Me Pyrazin-2-yl CF ₃ Me 4-CClF ₂ -Pyrimidin-5-yl CF ₃ Me Benzofuran-2-yl CF ₃ Me Ph CF ₃ Me 2-Cl-Ph CF ₃ Me 3-Cl-Ph CF ₃ Me 4-Cl-Ph CF ₃ Me 2-F-Ph CF ₃ Me 3-F-Ph CF ₃ Me 4-F-Ph CF ₃ Me 2-Me-Ph CF ₃ Me 3-Me-Ph CF ₃ Me 4-Me-Ph CF ₃ Me 2-MeO-Ph CF ₃ Me 3-MeO-Ph CF ₃ Me 4-MeO-Ph CF ₃ Me 4-Br-Ph CF ₃ Me 2,4-Cl ₂ -Ph CF ₃ Me 3,4-Cl ₂ -Ph CF ₃ Me 2,4,6-Cl ₃ -Ph CF ₃ Me 3,4- (MeO) ₂ -Ph CF ₃ Me 2-Cl-4-Me-Ph CF ₃ Me 2-MeO-4-Me-Ph CF ₃ Me 2,4-Me ₂ -Ph CF ₃ Me 2,5-Me ₂ -Ph CF ₃ Me 2,6-F ₂ -Ph CF ₃ Me 2,3,4,5,6-F _Five -Ph CF ₃ Me 4-Et-Ph CF ₃ Me 4-i-Pr-Ph CF ₃ Me 4-t-Bu-Ph CF ₃ Me 4-CF ₃ -Ph CF ₃ Me 4-i-PrO-Ph CF ₃ Me 4-t-BuO-Ph CF ₃ Me 4-CHF ₂ O-Ph CF ₃ Me 4-CF ₃ O-Ph CF ₃ Me 4-MeS-Ph CF ₃ Me 4-CHO-Ph CF ₃ Me 4-NO ₂ -Ph CF ₃ Me 4-CN-Ph CF ₃ Me 4-PhCH ₂ O-Ph CF ₃ Me 4-MeC (O) -Ph CF ₃ Me 4-PhC (O) -Ph CF ₃ Me 4-MeOCH ₂ -Ph CF ₃ Me 4-MeSCH ₂ -Ph CF ₃ Me 4-MeC (O) O-Ph CF ₃ Me 4-Ph-Ph CF ₃ Me 4-PhO-Ph CF ₃ Me 2,3-Cl ₂ -Ph CF ₃ Me 3,5-Cl ₂ -Ph CF ₃ Me 2,6-Cl ₂ -Ph CF ₃ Me 2,5-Cl ₂ -Ph CF ₃ Me 2,3-F ₂ -Ph CF ₃ Me 2,5-F ₂ -Ph CF ₃ Me 3,4-F ₂ -Ph CF ₃ Me 3,5-F ₂ -Ph CF ₃ Me 2,4-F ₂ -Ph CF ₃ Me 2-CF ₃ -Ph CF ₃ Me 2-F-6-CF ₃ -Ph CF ₃ Me 2-F-6-Cl-Ph CF ₃ Me 2-F-6-Me-Ph CF ₃ Me 2-F-6-MeO-Ph CF ₃ Me 2-F-4-Cl-Ph CF ₃ Me 2-F-4-CF ₃ -Ph CF ₃ Me 2-F-4-Me-Ph CF ₃ Me 2-F-4-MeO-Ph CF ₃ Me 3-F-4-Cl-Ph CF ₃ Me 3-F-4-Me-Ph CF ₃ Me 3-F-4-MeO-Ph CF ₃ Me 4-F-2-Cl-Ph CF ₃ Me 4-F-2-Me-Ph CF ₃ Me 4-F-2-MeO-Ph CF ₃ Me 4-F-3-Cl-Ph CF ₃ Me 4-F-3-Me-Ph CF ₃ Me 4-F-3-MeO-Ph CF ₃ Me 2-OH-Ph CF ₃ Me 4-I-Ph CF ₃ Me 4-MeOC (O) -Ph CF ₃ Me 2,6-Me ₂ -Ph CF ₃ Me 2,6- (MeO) ₂ -Ph CF ₃ Me 3-CF ₃ -Ph CF ₃ Me 2-Br-Ph CF ₃ Me 3-Br-Ph CF ₃ Me 2-MeC (O) -Ph CF ₃ Me 4-c-Pr-Ph CF ₃ Me 4-PhS-Ph CF ₃ Me 2,3-Me ₂ -Ph CF ₃ Me 3,4-Me ₂ -Ph CF ₃ Me 3,5-Me ₂ -Ph CF ₃ Me 2,3- (MeO) ₂ -Ph CF ₃ Me 2,4- (MeO) ₂ -Ph CF ₃ Me 2,5- (MeO) ₂ -Ph CF ₃ Me 3,5- (MeO) ₂ -Ph CF ₃ Me 2-F-4-I-Ph CF ₃ Me 2-F-4-EtO-Ph CF ₃ Me 2-F-6-Ph-Ph CF ₃ Me 3,4-methylenedioxy-Ph CF ₃ Me 3,4-ethylenedioxy-Ph CF ₃ Me 2-F-4-Br-Ph CF ₃ Me 2-Cl-4-Me-Ph CF ₃ Me 2,4,6-Me ₃ -Ph CF ₃ Et Et CF ₃ Et n-Pr CF ₃ Et i-Pr CF ₃ Et n-Bu CF ₃ Et s-Bu CF ₃ Et t-Bu CF ₃ Et CF ₃ CF ₃ Et CF ₂ CF ₃ CF ₃ Et 1-Naphthyl CF ₃ Et 2-Naphthyl CF ₃ Et Ph CF ₃ Et 2-Cl-Ph CF ₃ Et 4-Cl-Ph CF ₃ Et 2-F-Ph CF ₃ Et 4-F-Ph CF ₃ Et 2-Me-Ph CF ₃ Et 3-Me-Ph CF ₃ Et 4-Me-Ph CF ₃ Et 2-MeO-Ph CF ₃ Et 3-MeO-Ph CF ₃ Et 4-MeO-Ph CF ₃ Et 4-Br-Ph CF ₃ Et 2,6-F ₂ -Ph CF ₃ Et 4-CF ₃ -Ph CF ₃ Et 4-Ph-Ph CF ₃ Et 4-PhO-Ph CF ₃ Et 2,3-F ₂ -Ph CF ₃ Et 2,5-F ₂ -Ph CF ₃ Et 3,4-F ₂ -Ph CF ₃ Et 3,5-F ₂ -Ph CF ₃ Et 2,4-F ₂ -Ph CF ₃ Et 2-F-4-Cl-Ph CF ₃ Et 2-F-4-Me-Ph CF ₃ Et 2-F-4-MeO-Ph CF ₃ Et 3-F-4-Cl-Ph CF ₃ Et 3-F-4-Me-Ph CF ₃ Et 3-F-4-MeO-Ph CF ₃ Et 4-F-2-Cl-Ph CF ₃ Et 4-F-2-Me-Ph CF ₃ Et 4-F-2-MeO-Ph CF ₃ Et 4-F-3-Cl-Ph CF ₃ Et 4-F-3-Me-Ph CF ₃ Et 4-F-3-MeO-Ph CF ₃ Et 2,6- (MeO) ₂ -Ph CF ₃ Et 2-Br-Ph CF ₃ Et 3-Br-Ph CF ₃ Et 4-EtO-Ph CF ₃ Et 2,3-Me ₂ -Ph CF ₃ Et 3,4-Me ₂ -Ph CF ₃ Et 3,5-Me ₂ -Ph CF ₃ Et 2-Cl-3-Me-Ph CF ₃ Et 2-Cl-4-Me-Ph CF ₃ Et 3-Cl-4-Me-Ph CF ₃ Et 4-Cl-2-Me-Ph CF ₃ Et 4-Cl-3-Me-Ph CF ₃ Et 2,4,6-Me ₃ -Ph CF ₃ Pr Et CF ₃ Pr n-Pr CF ₃ Pr i-Pr CF ₃ Pr s-Bu CF ₃ Pr t-Bu CF ₃ Pr CF ₃ CF ₃ Pr CF ₂ CF ₃ CF ₃ Pr 1-Me-3-Cl-Pyrazol-4-yl CF ₃ Pr 1-Me-5-Cl-Pyrazol-3-yl CF ₃ Pr 1-Me-5-Cl-Pyrazol-4-yl CF ₃ Pr Ph CF ₃ Pr 2-Cl-Ph CF ₃ Pr 4-Cl-Ph CF ₃ Pr 2-F-Ph CF ₃ Pr 4-F-Ph CF ₃ Pr 2-Me-Ph CF ₃ Pr 4-Me-Ph CF ₃ Pr 4-Br-Ph CF ₃ Pr 2,6-F ₂ -Ph CF ₃ Pr 2,3-F ₂ -Ph CF ₃ Pr 2,5-F ₂ -Ph CF ₃ Pr 3,4-F ₂ -Ph CF ₃ Pr 3,5-F ₂ -Ph CF ₃ Pr 2,4-F ₂ -Ph CF ₃ Pr 2-Br-Ph CF ₃ Br n-Pr CF ₃ Br i-Pr CF ₃ Br s-Bu CF ₃ Br t-Bu CF ₃ Br CF ₃ CF ₃ Br CF ₂ CF ₃ CF ₃ Br Ph CF ₃ Br 2-Cl-Ph CF ₃ Br 4-Cl-Ph CF ₃ Br 2-F-Ph CF ₃ Br 4-F-Ph CF ₃ Br 2-Me-Ph CF ₃ Br 4-Me-Ph CF ₃ Br 4-Br-Ph CF ₃ i-Pr i-Pr CF ₃ i-Pr s-Bu CF ₃ i-Pr t-Bu CF ₃ i-Pr CF ₃ CF ₃ i-Pr CF ₂ CF ₃ CF ₃ i-Pr Ph CF ₃ i-Pr 2-Cl-Ph CF ₃ i-Pr 4-Cl-Ph CF ₃ i-Pr 2-F-Ph CF ₃ i-Pr 4-F-Ph CF ₃ i-Pr 2-Me-Ph CF ₃ i-Pr 4-Me-Ph CF ₃ i-Pr 4-Br-Ph CF ₃ i-Pr 2-Br-Ph CF ₃ ――――――――――――――――――――――――――――――――――― [Table 2]

[0227]

[Chemical 50]

[0228]

[Chemical 51]

[0229]

[Chemical 52]

[0230]

[Chemical 53]

[0231]

[Chemical 54]

[0232]

[Chemical 55]

[0233]

[Chemical 56]

[0234]

[Chemical 57]

[0235]

[Chemical 58]

[0236]

[Chemical 59]

[0237]

[Chemical 60]

[0238]

[Chemical formula 61]

[0239]

[Chemical formula 62]

[0240]

[Chemical formula 63]

[0241]

[Chemical 64]

[0242]

[Chemical 65]

[0243]

[Table 2] ――――――――――――――――――――――――――――――――――― Ya Yb X ―――――――― ――――――――――――――――――――――――――― HHH H Cl H HFH H Br H HIH H Me HH Et HH n-Pr HH i-Pr HH n -Bu HH i-Bu HH s-Bu HH t-Bu HH n-Pen HH 3-Me-n-Bu HH n-Hex HH Ethenyl HH 1-Propenyl HH Ethynyl HH CF ₃ HH c-Pr HH c-Hex HH MeO HH t-BuO HH CF ₃ OH H MeS H H MeSO H H MeSO ₂ H H NO ₂ H H NC H H CHO H H Me ₂ NH H PhCH ₂ H H PhCH = CH H H 4-Cl-PHCH = CH H H PhCH = CHCH ₂ HH PhCC HH Ph HH MeNHC (O) HH PhNHC (O) HH EtNHC (O) HH 2-F-PhNHC (O) HH 3-F-PhNHC (O) HH 4-F-PhNHC (O) HH 2-Cl-PhNHC ( O) HH 3-Cl-PhNHC (O) HH 4-Cl-PhNHC (O) HH 2-Me-PhNHC (O) HH 3-Me-PhNHC (O) HH 4-Me-PhNHC (O) HH 2- Br-PhNHC (O) HH 3-Br-PhNHC (O) HH 4-Br-PhNHC (O) HH 2-MeO-PhNHC (O) HH 3-MeO-PhNHC (O) HH 4-MeO-PhNHC (O ) HH 2,6-F ₂ -PhNHC (O) H H MeOC (O) H H MeOCH ₂ H H MeOC (= NOMe) H H MeC (= NOMe) H H MeC (O) H H C H ₂ SMe H H CH ₂ SCH ₂ Ph H H Pyrazol-1-ylCH ₂ H H ClCH ₂ H H BrCH ₂ H H CF ₃ CF ₂ HH PhC (O) NH HH 1-Naphthyl HH 2-Naphthyl HH 1-Me-Pyrazol-5- yl HH 1-Me-3-Cl-Pyrazol-5-yl HH 2-F-Furan-3-yl HH Oxazol-2-yl HH 1,2,4-Oxadiazol-3-yl HH 1,2,4- Thiadizazol-5-yl HH 1,2,4-Triazol-1-yl HH 1,2,3-Triazol-1-yl HH 1,2,3,4-Tetrazol-1-yl HH 6-MeO-Pyrimidin- 2-yl HH Pyridazin-3-yl HH 1,3,5-Triazin-2-yl HH 1,2,4-Triazin-6-yl HH 1-Me-Pyrrol-2-yl HH Furan-2-yl HH Thiophen-2-yl HH Thiazol-5-yl HH 2,4-Me ₂ -Oxazol-5-yl HH 3-Me-Isothiazol-5-yl HH Isoxazol-5-yl HH 1-Me-Imidazol-5-yl HH 4-Me-1,2,3-Thiadiazol-5-yl HH Pyridin-4-yl HH Quinoxalin-2-yl HH 6-Cl-Quinoxalin-2-yl HH 6-F-Quinoxalin-2-yl HH 1 -Me-Indol-3-yl HH Benzothiazol-2-yl HH 5-F-Benzothiazol-2-yl HH 6-F-Benzothiazol-2-yl HH Quinolin-4-yl HH Pyrazin-2-yl HH 4-CClF ₂ -Pyrimidin-5-yl HH Benzofuran-2-yl HH Ph HH 2-Cl-Ph HH 3-Cl-Ph HH 4-Cl-Ph HH 2-F-Ph HH 3-F-Ph HH 4-F- Ph HH 2-Me-Ph HH 3-Me-Ph HH 4-Me-Ph HH 2- MeO-Ph H H 3-MeO-Ph H H 4-MeO-Ph H H 4-Br-Ph H H 2,4-Cl ₂ -Ph H H 3,4-Cl ₂ -Ph H H 2,4,6-Cl ₃ -Ph HH 3,4- (MeO) ₂ -Ph H H 2-Cl-4-Me-Ph H H 2-MeO-4-Me-Ph H H 2,4-Me ₂ -Ph H H 2,5-Me ₂ -Ph HH 2,6-F ₂ -Ph H H 2,3,4,5,6-F ₅ -Ph H H 4-Et-Ph H H 4-i-Pr-Ph H H 4-t-Bu-Ph H H 4-CF ₃ -Ph HH 4-i-PrO-Ph HH 4-t-BuO-Ph HH 4-CHF ₂ O-Ph H H 4-CF ₃ O-Ph H H 4-MeS-Ph H H 4-CHO-Ph H H 4-NO ₂ -Ph H H 4-CN-Ph H H 4-PhCH ₂ O-Ph H H 4-MeC (O) -Ph H H 4-PhC (O) -Ph H H 4-MeOCH ₂ -Ph H H 4-MeSCH ₂ -Ph HH 4-MeC (O) O-Ph HH 4-Ph-Ph HH 4-PhO-Ph HH 2,3-Cl ₂ -Ph H H 3,5-Cl ₂ -Ph H H 2,6-Cl ₂ -Ph HH 2 , 5-Cl ₂ -Ph H H 2,3-F ₂ -Ph H H 2,5-F ₂ -Ph H H 3,4-F ₂ -Ph H H 3,5-F ₂ -Ph H H 2,4-F ₂ -Ph HH 2-CF ₃ -Ph H H 2-F-6-CF ₃ -Ph HH 2-F-6-Cl-Ph HH 2-F-6-Me-Ph HH 2-F-6-MeO-Ph HH 2-F-4-Cl-Ph HH 2-F-4-CF ₃ -Ph HH 2-F-4-Me-Ph HH 2-F-4-MeO-Ph HH 3-F-4-Cl- Ph HH 3-F-4-Me-Ph HH 3-F-4-MeO-Ph HH 4-F-2-Cl-Ph HH 4-F-2-Me-Ph HH 4-F-2-MeO- Ph HH 4-F-3-Cl-Ph HH 4-F-3-Me-Ph HH 4-F-3-MeO-Ph HH 2-OH-Ph HH 4-I-Ph HH 4-M eOC (O) -Ph H H 2,6-Me ₂ -Ph H H 2,6- (MeO) ₂ -Ph H H 3-CF ₃ -Ph HH 2-Br-Ph HH 3-Br-Ph HH 2-MeC ( O) -Ph HH 4-c-Pr-Ph HH 4-PhS-Ph HH 2,3-Me ₂ -Ph H H 3,4-Me ₂ -Ph H H 3,5-Me ₂ -Ph HH 2,3- (MeO) ₂ -Ph H H 2,4- (MeO) ₂ -Ph H H 2,5- (MeO) ₂ -Ph H H 3,5- (MeO) ₂ -Ph HH 2-F-4-I-Ph HH 2-F-4-EtO-Ph HH 2-F-6-Ph-Ph HH 3,4-methylenedioxy-Ph HH 3,4-ethylenedioxy-Ph HH 2-F-4-Br-Ph HH 2-Cl- 4-Me-Ph HH 2,4,6-Me ₃ -Ph H -CH = CH-CH = CH- H -CH = N-CH = CH- H -N = CH-CH = CH- H-(CH ₂ ) ₃ -H-(CH ₂ ) ₄ -H -CH ₂ -CH ₂ -O-CH ₂ -H -CO- (CH ₂ ) ₃ -H -CH ₂ -CH (CH ₂ Ph) -CH _2- H -CH ₂ -CH ₂ -CH (Me) -CH ₂ -H -CH = CH-CH = C (OMe)-H Me HH Me Cl H Me FH Me Br H Me IH Me Me H Me Et H Me n -Pr H Me i-Pr H Me n-Bu H Me i-Bu H Me s-Bu H Me t-Bu H Me n-Pen H Me 3-Me-n-Bu H Me n-Hex H Me Ethenyl H Me 1-Propenyl H Me Ethynyl H Me CF ₃ H Me c-Pr H Me c-Hex H Me MeO H Me t-BuO H Me CF ₃ OH Me MeS H Me MeSO H Me MeSO ₂ H Me NO ₂ H Me NC H Me CHO H Me Me ₂ NH Me PhCH ₂ H Me PhCH = CH H Me 4-Cl-PHCH = CH H Me PhCH = CHCH ₂ H Me PhCC H Me Ph H Me MeNHC (O) H Me PhNHC (O) H Me EtNHC (O) H Me 2-F-PhNHC (O) H Me 3-F-PhNHC (O) H Me 4-F-PhNHC (O) H Me 2-Cl-PhNHC (O) H Me 3-Cl-PhNHC (O) H Me 4-Cl-PhNHC (O) H Me 2-Me-PhNHC (O) H Me 3-Me-PhNHC (O) H Me 4-Me-PhNHC (O) H Me 2-Br-PhNHC (O) H Me 3-Br-PhNHC (O) H Me 4-Br-PhNHC (O) H Me 2-MeO-PhNHC (O) H Me 3-MeO-PhNHC (O) H Me 4-MeO-PhNHC (O) H Me 2,6-F ₂ -PhNHC (O) H Me MeOC (O) H Me MeOCH ₂ H Me MeOC (= NOMe) H Me MeC (= NOMe) H Me MeC (O) H Me CH ₂ SMe H Me CH ₂ SCH ₂ Ph H Me Pyrazol-1-ylCH ₂ H Me ClCH ₂ H Me BrCH ₂ H Me CF ₃ CF ₂ H Me PhC ( O) NH H Me 1-Naphthyl H Me 2-Naphthyl H Me 1-Me-Pyrazol-5-yl H Me 1-Me-3-Cl-Pyrazol-5-yl H Me 2-F-Furan-3-yl H Me Oxazol-2-yl H Me 1,2,4-Oxadiazol-3-yl H Me 1,2,4-Thiadizazol-5-yl H Me 1,2,4-Triazol-1-yl H Me 1, 2,3-Triazol-1-yl H Me 1,2,3,4-Tetrazol-1-yl H Me 6-MeO-Pyrimidin-2-yl H Me Pyridazin-3-yl H Me 1,3,5- Triazin-2-yl H Me 1,2,4-Triazin-6-yl H Me 1-Me-Pyrrol-2-yl H Me Furan-2-yl H Me Thiophen-2-yl H Me Thiazol-5-yl H Me 2,4-Me ₂ -Oxazol-5-yl H Me 3-Me-Isothiazol-5 -yl H Me Isoxazol-5-yl H Me 1-Me-Imidazol-5-yl H Me 4-Me-1,2,3-Thiadiazol-5-yl H Me Pyridin-4-yl H Me Quinoxalin-2- yl H Me 6-Cl-Quinoxalin-2-yl H Me 6-F-Quinoxalin-2-yl H Me 1-Me-Indol-3-yl H Me Benzothiazol-2-yl H Me 5-F-Benzothiazol-2 -yl H Me 6-F-Benzothiazol-2-yl H Me Quinolin-4-yl H Me Pyrazin-2-yl H Me 4-CClF ₂ -Pyrimidin-5-yl H Me Benzofuran-2-yl H Me Ph H Me 2-Cl-Ph H Me 3-Cl-Ph H Me 4-Cl-Ph H Me 2-F-Ph H Me 3-F-Ph H Me 4-F-Ph H Me 2-Me-Ph H Me 3-Me-Ph H Me 4-Me-Ph H Me 2-MeO-Ph H Me 3-MeO-Ph H Me 4-MeO-Ph H Me 4-Br-Ph H Me 2,4-Cl ₂ -Ph H Me 3,4-Cl ₂ -Ph H Me 2,4,6-Cl ₃ -Ph H Me 3,4- (MeO) ₂ -Ph H Me 2-Cl-4-Me-Ph H Me 2-MeO -4-Me-Ph H Me 2,4-Me ₂ -Ph H Me 2,5-Me ₂ -Ph H Me 2,6-F ₂ -Ph H Me 2,3,4,5,6-F ₅ -Ph H Me 4-Et-Ph H Me 4-i-Pr-Ph H Me 4-t-Bu-Ph H Me 4-CF ₃ -Ph H Me 4-i-PrO-Ph H Me 4-t- BuO-Ph H Me 4-CHF ₂ O-Ph H Me 4-CF ₃ O-Ph H Me 4-MeS-Ph H Me 4-CHO-Ph H Me 4-NO ₂ -Ph H Me 4-CN-Ph H Me 4-PhCH ₂ O-Ph H Me 4-MeC (O) -Ph H Me 4-PhC (O) -Ph H Me 4-MeOCH ₂ -Ph H Me 4-MeSCH ₂ -Ph H Me 4-MeC (O) O-Ph H Me 4-Ph-Ph H Me 4-PhO-Ph H Me 2,3-Cl ₂ -Ph H Me 3,5-Cl ₂ -Ph H Me 2,6-Cl ₂ -Ph H Me 2,5-Cl ₂ -Ph H Me 2,3-F ₂ -Ph H Me 2,5-F ₂ -Ph H Me 3,4-F ₂ -Ph H Me 3,5-F ₂ -Ph H Me 2,4-F ₂ -Ph H Me 2-CF ₃ -Ph H Me 2-F-6-CF ₃ -Ph H Me 2-F-6-Cl-Ph H Me 2-F- 6-Me-Ph H Me 2-F-6-MeO-Ph H Me 2-F-4-Cl-Ph H Me 2-F-4-CF ₃ -Ph H Me 2-F-4-Me-Ph H Me 2-F-4-MeO-Ph H Me 3-F-4-Cl-Ph H Me 3-F-4-Me-Ph H Me 3-F-4-MeO-Ph H Me 4-F- 2-Cl-Ph H Me 4-F-2-Me-Ph H Me 4-F-2-MeO-Ph H Me 4-F-3-Cl-Ph H Me 4-F-3-Me-Ph H Me 4-F-3-MeO-Ph H Me 2-OH-Ph H Me 4-I-Ph H Me 4-MeOC (O) -Ph H Me 2,6-Me ₂ -Ph H Me 2,6- (MeO) ₂ -Ph H Me 3-CF ₃ -Ph H Me 2-Br-Ph H Me 3-Br-Ph H Me 2-MeC (O) -Ph H Me 4-c-Pr-Ph H Me 4 -PhS-Ph H Me 2,3-Me ₂ -Ph H Me 3,4-Me ₂ -Ph H Me 3,5-Me ₂ -Ph H Me 2,3- (MeO) ₂ -Ph H Me 2, 4- (MeO) ₂ -Ph H Me 2,5- (MeO) ₂ -Ph H Me 3,5- (MeO) ₂ -Ph H Me 2-F-4-I-Ph H Me 2-F-4 -EtO-Ph H Me 2-F-6-Ph-Ph H Me 3,4-methylenedioxy-Ph H Me 3,4-ethylenedioxy-Ph H Me 2-F-4-Br-Ph H Me 2-Cl- 4-Me-Ph H Me 2,4,6-Me ₃ -Ph H Et Et H Et n-Pr H Et i-Pr H Et n-Bu H Et s-Bu H Et t-Bu H Et CF ₃ H Et CF ₂ CF ₃ H Et 1-Naphthyl H Et 2-Naphthyl H Et Ph H Et 2-Cl-Ph H Et 4-Cl-Ph H Et 2-F-Ph H Et 4-F-Ph H Et 2-Me-Ph H Et 3-Me-Ph H Et 4-Me-Ph H Et 2-MeO-Ph H Et 3-MeO-Ph H Et 4-MeO-Ph H Et 4-Br-Ph H Et 2,6-F ₂ -Ph H Et 4-CF ₃ -Ph H Et 4-Ph-Ph H Et 4-PhO- Ph H Et 2,3-F ₂ -Ph H Et 2,5-F ₂ -Ph H Et 3,4-F ₂ -Ph H Et 3,5-F ₂ -Ph H Et 2,4-F _2- Ph H Et 2-F-4-Cl-Ph H Et 2-F-4-Me-Ph H Et 2-F-4-MeO-Ph H Et 3-F-4-Cl-Ph H Et 3-F -4-Me-Ph H Et 3-F-4-MeO-Ph H Et 4-F-2-Cl-Ph H Et 4-F-2-Me-Ph H Et 4-F-2-MeO-Ph H Et 4-F-3-Cl-Ph H Et 4-F-3-Me-Ph H Et 4-F-3-MeO-Ph H Et 2,6- (MeO) ₂ -Ph H Et 2-Br -Ph H Et 3-Br-Ph H Et 4-EtO-Ph H Et 2,3-Me ₂ -Ph H Et 3,4-Me ₂ -Ph H Et 3,5-Me ₂ -Ph H Et 2- Cl-3-Me-Ph H Et 2-Cl-4-Me-Ph H Et 3-Cl-4-Me-Ph H Et 4-Cl-2-Me-Ph H Et 4-Cl-3-Me- Ph H Et 2,4,6-Me ₃ -Ph H Pr Et H Pr n-Pr H Pr i-Pr H Pr s-Bu H Pr t-Bu H Pr CF ₃ H Pr CF ₂ CF ₃ H Pr 1- Me-3-Cl-Pyrazol-4-yl H Pr 1-Me-5-Cl-Pyrazol-3-yl H Pr 1-Me-5-Cl-Pyrazol-4-yl H Pr Ph H Pr 2-Cl -Ph H Pr 4-Cl-Ph H Pr 2-F-Ph H Pr 4-F-Ph H Pr 2-Me-Ph H Pr 4-Me-Ph H Pr 4-Br-Ph H Pr 2,6- F ₂ -Ph H Pr 2,3-F ₂ -Ph H Pr 2,5-F ₂ -Ph H Pr 3,4-F ₂ -Ph H Pr 3,5-F ₂ -Ph H Pr 2,4- F ₂ -Ph H Pr 2-Br-Ph H Br n-Pr H Br i-Pr H Br s-Bu H Br t-Bu H Br CF ₃ H Br CF ₂ CF ₃ H Br Ph H Br 2-Cl- Ph H Br 4-Cl-Ph H Br 2-F-Ph H Br 4-F-Ph H Br 2-Me-Ph H Br 4-Me-Ph H Br 4-Br-Ph H i-Pr i-Pr H i-Pr s-Bu H i-Pr t-Bu H i-Pr CF ₃ H i-Pr CF ₂ CF ₃ H i-Pr Ph H i-Pr 2-Cl-Ph H i-Pr 4-Cl- Ph H i-Pr 2-F-Ph H i-Pr 4-F-Ph H i-Pr 2-Me-Ph H i-Pr 4-Me-Ph H i-Pr 4-Br-Ph H i-Pr 2-Br-Ph H ――――――――――――――――――――――――――――――――――― [Table 3]

[0244]

[Chemical formula 66]

[0245]

[Chemical formula 67]

[0246]

[Chemical 68]

[0247]

[Chemical 69]

[0248]

[Table 3] ――――――――――――――――――――――――――――――――――― -Va-Vb-Vc-Vd- X ― ―――――――――――――――――――――――――――――――――― -S-CH ₂ -C (OH) (C ₂ F ₅ ) -N (Me)-H -S-CH (CH ₂ Br) -CH ₂ -N (Me)-H -SS-CH = N- H -SSC (Ph) = N- H -SSC (CF ₃ ) = N- H -SN (Me) -CH ₂ -S- H -SN (Ph) -CH ₂ -S- H -SN (Me) -CH (Ph) -S- H -N = NC (= O)- O-H-N = N-CH (Me) -O-H-N = N-CH (Ph) -O-H-SO-CH = N-H-SOC (Me) = N-H-SOC (Ph ) = N- H -CH = CH-N (Me) -S- H -CH = CH-N (Ph) -S- H -C (Me) = CH-N (Ph) -S- H -CH = C (Me) -N (Ph) -S- H -C (Me) = C (Me) -N (Ph) -S- H -CH = CH-N (Me) -O- H -CH = CH- N (Ph) -O- H -C (Me) = CH-N (Ph) -O- H -CH = C (Me) -N (Ph) -O- H -C (Me) = C (Me) -N (Ph) -O-H -CH ₂ -CH ₂ -N (Me) -O- H -CH ₂ -CH ₂ -N (Ph) -O- H -CH ₂ -C (= O) -N (Ph) -O- H -CH = NN (Me) -CH ₂ -H -CH = NN (Ph) -CH ₂ -H -CH = NN (Ph) -C (= O)-H -C (Me ) = NN (Ph) -C (= O)-H -N (Me) -CH ₂ -N (Ph) -O- H -N (Me) -C (= O) -N (Ph) -O- _{H -N (Me) -CH 2 -N} (Ph) -S- H -N (Me) -C (= O) -N (Ph) -S- H -S-CH 2 -C (Ph) = N -H -S-CH ₂ -N (Ph) -N (Me)-H -SC ( = O) -N (Ph) -N (Me)-H -O-CH ₂ -C (Ph) = N- H -O-CH ₂ -N (Ph) -N (Me)-H -OC (= O) -N (Ph) -N (Me) -H-S-CH (Ph) -N (Me) -N (Me) -H-O-CH (Ph) -N (Me) -N (Me) -H -N = C (Me) -N = N- H -N = C (Ph) -N = N- H -N = CH-CH = N- H -N = C (Ph) -CH = N- H -SN (Me) -CH ₂ -N (Me)-H -SN (Ph) -CH ₂ -N (Me)-H -ON (Me) -CH ₂ -N (Me)-H -ON (Ph ) -CH ₂ -N (Me)-H -CH ₂ -CH ₂ -N (Me) -N (Me)-H -CH ₂ -CH ₂ -N (Ph) -N (Me)-H -CH ₂ -C (Ph) = NN (Me)-H -CH = C (Ph) -N (Me) -N (Me)-H -CH = CH-N (Ph) -N (Me)-H -CH = C (Ph) -N = N- H -CH = NC (Ph) = N- H -CH ₂ -CH ₂ -N = N- H -N (Me) -O-CH (Ph) -N (Me) -H -O-CH ₂ -C (Ph) = N- H -CH ₂ -CH ₂ -CH ₂ -O- H -CH ₂ -CH ₂ -CH ₂ -S- H -CH ₂ -CH ₂ -CH ₂ -N (Me)-H -CH = CH-CH ₂ -O- H -CH = CH-CH ₂ -S- H -CH = CH-CH ₂ -N (Me)-H -CH ₂ -SC ( = N-Ph) -N (Me)-H -O-CH ₂ -CH ₂ -N (Me)-H -O-CH ₂ -CH (Ph) -N (Me)-H -O-CH = CH -N (Me)-H -O-CH = CH (Ph) -N (Me)-H -N (Me) -CH ₂ -CH ₂ -N (Me)-H -N (Me) -CH _2- CH (Ph) -N (Me)-H -N (Me) -CH = CH-N (Me)-H -N (Me) -CH = CH (Ph) -N (Me)-H -S-CH = NN (Me)-H -SC (Ph) = NN (Me)-H -S-CH ₂ -N = N- H -S-CH (Ph) -N = N- H -O-CH = NN ( Me)-H -OC (Ph) = NN (Me)-H -N (Me) -CH ₂ -N (Me) -N (Me)-H -N (Me) -CH (Ph) -N (Me) -N (Me)-H -N (Me) -CH ₂ -N (Ph) -N (Me)-H -N (Me) -CH (Me) -N (Ph) -N (Me)-H -N (Me) -CH = NN (Me)-H -N (Me) -C (Ph) = NN (Me)-H -N (Me) -CH = NN (Me)-H -N (Me) -CH = NN (Me)-H -N = CH-N (Me) -N (Me)-H -N = C (Ph) -N (Me)- N (Me)-H -N = CH-N (Me) -N (Me)-H -N = CH-N (Ph) -N (Me)-H -SN = CH-N (Me)-H- SN = C (Ph) -N (Me)-H -SN (Me) -CH = N- H -SN (Ph) -C (Ph) = N- H -SN (Me) -C (Ph) = N -H -SN (Ph) -CH = N- H -ON = CH-N (Me)-H -ON = C (Ph) -N (Me)-H -ON (Me) -CH = N- H- ON (Ph) -C (Ph) = N- H -ON (Me) -C (Ph) = N- H -ON (Ph) -CH = N- H -N (Me) -O-CH = N- H-N (Ph) -OC (Ph) = N-H-N (Me) -OC (Ph) = N-H-N (Ph) -O-CH = N-H-N (Me) -CH ₂ -N = N- H -N (Me) -CH (Ph) -N = N- H -SN = CH-S- H -SN = C (Ph) -S- H -O-CH = CH-O- H -OC (Me) = CH-O- H -OC (Ph) = CH-O- H -OC (Me) = C (Ph) -O- H -O-CH ₂ -CH ₂ -O- H- O-CH ₂ -CH (Ph) -O- H -O-CH (Ph) -CH (Me) -O- H -S-CH ₂ -CH ₂ -O- H -S-CH ₂ -CH (Ph ) -O- H -S-CH (Ph) -CH (Me) -O- H -S-CH (Me) -CH (Ph) -O- H -S-CH (Ph) -CH ₂ -O- _{H -S-CH 2 -CH 2 -S-} H -S-CH 2 -CH (Ph) -S- H -S-CH (Ph) -CH (Me) -S- H -N (Me) -CH _{2 -CH 2 -O- H -N (Me} ) -CH 2 -CH (Ph) -O- H -N (Me) -CH (Ph) -CH (Me) -O- H -N (Me) - CH (Me) -CH (Ph) -O- H -N (Me) -CH (Ph) -CH ₂ -O- H -CH ₂ -N = CH-S- H -CH ₂ -N = C (Ph) -S- H -CH ₂ -S-CH = N- H -CH ₂ -SC (Ph) = N- H -CH ₂ -N (Me) -CH ₂ -S- H -CH ₂ -N (Me) -CH (Ph) -S- H -CH ₂ -N (Ph) -CH ₂ -S- H -CH ₂ -N (Ph) -CH (Ph) -S- H ―――――――――――――――――――― ――――――――――――――― [Table 4]

[0249]

[Chemical 70]

[0250]

[Table 4] ――――――――――――――――――――――――――――――――――― -Va-Vb-Vc-Vd-Ve- X ――――――――――――――――――――――――――――――――――― -S-CH ₂ -CH = NN (Me)-H -S-CH ₂ -CH = NN (Ph)-H -S-CH ₂ -C (Me) = NN (Me)-H -S-CH ₂ -C (Ph) = NN (Me)-H -SC (= O) -CH ₂ -N (Me) -N (Me)-H -SC (= O) -CH ₂ -N (Ph) -N (Me)-H -S-CH = C (Me)- N (Ph) -N (Me)-H -SC (= O) -C (Me) = NN (Me)-H -SC (= O) -C (Ph) = NN (Me)-H -CH ₂ -S-CH = CH-N (Me)-H -N = CH-N = C (F) -N (Me)-H -N = CH-N = C (Cl) -N (Me)-H- N = CH-N = C (Br) -N (Me)-H -N = CH-N = C (Ph) -N (Me)-H -N = CH-N = C (OPh) -N (Me )-H -N = CH-N = CH-N (Et)-H -N = CH-N = CH-N (Pr)-H -N = CH-N = C (CF ₃ ) -N (Me) -H -N = C (Cl) -N = CH-N (Me)-H -N = CH-N = CH-N (Me)-H -CH ₂ -CH ₂ -O-CH ₂ -CH _{2- H -CH 2 -CH 2 -N (Me} ) -CH 2 -CH 2 - H -N (Me) -CH 2 -CH = CH-S- H -N (Me) -CH 2 -C (Ph) = CH-S- H -N (Me) -CH ₂ -CH = C (Ph) -S- H -N (Me) -CH ₂ -CH = CH-O- H -N (Me) -CH ₂ -C (Ph) = CH-O- H -N (Me) -CH ₂ -CH = C (Ph) -O- H -N = CH-CH = CH-S- H -N = CH-C (Ph) = CH-S- H -N = CH-CH = C (Ph) -S- H -N = CH-CH = CH-O- H -N = CH-C (Ph) = CH-O- H -N = CH-CH = C (Ph) -O- H -S-CH ₂ -C (= O ) -N (Me) -N (Me)-H -S-CH ₂ -C (= O) -NPh-N (Me)-H -S-CH = CH-CH (Ph) -N (Me)- H -CH = CH-CH = C (Ph) -N (-OMe)-H -CH = CH-CH = C (F) -N (-OMe)-H -CH = CH-CH = C (Cl) -N (-OMe)-H -CH = CH-CH = C (-OPh) -N (-OMe)-H -N (Me) -CH ₂ -S-CH ₂ -N (Me)-H -N (Me) -CH ₂ -S-CH (Ph) -N (Me)-H -N (Me) -CH = CH-CH = N- H -N (Me) -C (Ph) = CH-CH = N- H -N (Me) -CH ₂ -CH ₂ -CH ₂ -N (Me)-H -N (Me) -CH (Ph) -CH ₂ -CH ₂ -N (Me)-H -O- _{CH 2 -CH 2 -CH 2 -N (} Me) - H -O-CH (Ph) -CH 2 -CH 2 -N (Me) - H -O-CH 2 -CH 2 -CH 2 -N (Me )-H -O-CH ₂ -CH ₂ -CH (Ph) -N (Me)-H -S-CH ₂ -CH ₂ -CH ₂ -N (Me)-H -S-CH (Ph) -CH _{2 -CH 2 -N (Me) -} H -S-CH 2 -CH 2 -CH 2 -N (Me) - H -S-CH 2 -CH 2 -CH (Ph) -N (Me) - H - N (Me) -CH ₂ -N (Me) -CH ₂ -N (Me)-H -N (Me) -CH ₂ -N (Me) -CH (Ph) -N (Me)-H -N ( Me) -CH ₂ -O-CH ₂ -N (Me)-H -N (Me) -CH ₂ -O-CH (Ph) -N (Me)-H -S-CH ₂ -CH = CH _2- N (Me)-H -S-CH ₂ -CH = CH (Ph) -N (Me)-H -S-CH = CH ₂ -N (Me) -N (Me)-H -S-CH = CH _{2 -N (Ph) -N (Me} ) - H ------------------------------- --- [Table 5]

[0251]

[Table 5] ―――――――――――――――――――――――――――――――――――

[0252]

[Chemical 71]

[0253]

[Chemical 72]

[0254]

[Chemical formula 73]

――――――――――――――――――――――――――――――――――― When applying the compound of the present invention as a fungicide, Usually, it is mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent,
Addition of binders, anti-caking agents, disintegrating agents, anti-degrading agents, etc., liquids, emulsions, wettable powders, water solutions, water-dispersible granules, water-soluble granules, suspensions, emulsions, suspo It can be put to practical use as a preparation of any dosage form such as emulsion, microemulsion, powder, granule and gel. Further, from the viewpoint of labor saving and improvement of safety, the formulation of any of the above dosage forms can be provided in a water-soluble package.

Examples of the solid carrier include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. Inorganic salts such as, synthetic silicic acid and synthetic silicates.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and the like.
Examples thereof include esters such as γ-butyrolactone, acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

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

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene fatty acid ester. Nonionic surfactants such as oxyethylene sorbitan fatty acid ester, alkyl sulfates, alkylbenzene sulfonates,
Lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid,
Anionic surfactants such as polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates and polystyrenesulfonates, alkylamine salts and alkyl quaternary ammonium salts Examples include cationic surfactants and amphoteric surfactants such as amino acid type and betaine type surfactants.

The content of these surfactants is not particularly limited, but is preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. Further, these surfactants may be used alone or in combination of two or more kinds.

When the compound of the present invention is used as a pesticide, other herbicides of various species, various insecticides, acaricides, nematicides, fungicides, plant growth regulators may be used as necessary during formulation or spraying. You may mix-apply with an agent, a synergist, a fertilizer, a soil conditioner.

[0262] In particular, when mixed with other pesticides or plant hormones, application can be expected to reduce costs by reducing the amount of application, to expand the sterilization spectrum due to the synergistic action of the mixed agents, and to have a higher sterilization effect. At this time, it is possible to combine a plurality of known pesticides at the same time. Examples of the types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chemi).
Cals Handbook, 2001 version. Specific examples of the common names are as follows, but the general names are not limited thereto.

Fungicide: acibenzola
r), ampropyfos, anilazine (a
nilazine), azaconazole, azoxystrobin, benalaxil
xyl), benodanil, benomyl
l), benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine,
Bordeaux mixture, blasticidin-
S (blasticidin-S), bromoconazol
e), bupirimate, butiobate (but
hiobate), calcium polysulphide
ulfide), captafol, captan, copper oxychlode
ride), carpropamid, carbendazim, carboxin, quinomethionat, chinomethionat, chlobenthiazone, chlorfenaz
zol), chloroneb, chlorothalonil (ch
lorothalonil), clozolinate (chlozolinate), cufraneb (cufraneb), cymoxanil (cymoxanil),
Cyproconazol, cyproconazol
prodinil), cyprofuram, debacarb, dichlorophen, diclobutrazol, diclofuranide (d)
iclhlofluanid), diclomedine (diclomedine), dichloran (dicloran), dietofencarb (diethofenc)
arb), diclocymet, difenoconazole, diflumethrin
orim), dimethirimol (dimethirimol), dimethomorph (diniconazol)
e), diiconazole-M (diniconazole-M), dinocap (dinocap), diphenylamine (diphenylamine),
Dipyrithione, ditalimphos (ditali)
mfos), dithianon, and dodem
orph), dodine, drazoxolone
on), edifenphos, epoxiconazole, etaconazol
e), ethirimol, etridiazole (et
ridiazole), famoxadone, fenarimol, febuconazol
e), fenfuram, fenpiclonil (f
enpiclonil), fenpropidin, fenpropimorph, fentin
tin), ferbam, ferimzo
ne), fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamid
e), flutolanil, flutriafol, flupet, folpet, fosetyl-aluminium, fuberidazole, furalaxyl,
Fenamidone, fenhexamide
examid), guazatine, hexachlorobenzene, hexaconazole
aconazole), hymexazol, imazalil, imibenconazol
e), iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane
hiolane), iprovalicarb, kasugamycin, kresoxime-methyl (k
resoxim-methyl), mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazol
e), metiram, metminostrobin (meto)
minostrobin), microbutanil (myclobutanil), nabam (nickel bis (dimethyldithiocarbamate)),
Nitrothal-isopropy
l), nuarimol, octhilinone
none), off-race (ofurace), oxadixyl (oxa)
dixyl), oxycarboxin, oxpoconazole fumarate,
Pefurzoate, penconazole
onazole), pencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidon
e), propamocarb hydrochlori
de), propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil.
l), pyroquilon, quinoxyphene (q
uinoxyfen, quintozene, sulfur (sulfu)
r), spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole
abendazole), thifluzamide, thiophanate-methyl, thiram
iram), tolclofos-methyl,
Tolylfluanid, triadimefon (tr
iadimefon), triadimenol, toriadimenol, triazoxide, tricyclazole
yclazole), tridemorph (tridemorph), triflumizole (triflumizole), triforine (triforine),
Triticonazole, validamycin, vinclozolin, zineb and ziram.

Bactericidal agent: Streptomycin (st
reptomycin), oxytetracycline
ine) and oxolinic acid.

Nematicides: aldoxycar
b), fosthiazate, fosthietan, oxamyl and fenamiphos.

Acaricides: amitraz, bromopropylate, chinomethionat, chlorobezilate
late), clofentezine (clofentezine), cyhexatine (cyhexatine), dicofol (dicofol), dienochlor (dienochlor), etoxazole (etoxaz)
ole), fenazaquin, fenbutatin oxide, fenpropathrin, fenproxim
ate), halfenprox (halfenprox), hexithiazox (hexythiazox), milbemectin (milbe)
mectin), propargite, pyridaben, pyrimidifen, tebufenpyrad, etc.

Insecticide: abamectin, acephate, acetamipir
id), azinphos-methyl, bendiocarb, benfurac
arb), bensultap, bifenthrin, buprofezin, butocarboxim, carbary
l), carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrif
os), chlorfenvinphos, chlorfluazuron, chlorfluazuron, clothianidin, chromafenozid
e), chlorpyrifos-methyl,
Cyfluthrin, beta-cyfluthrin, cypermethrin
rin), cyromazine, cyhalothrin (c
yhalothrin), lambda-cyhalotrin
hrin), deltamethrin, diafenthiuron, diazino
n), diacloden, diflubenzuron, dimethylvinph
os), diofenolan, disulfoton, dimethoate, EPN,
Esfenvalerate, ethiofencarb, ethiprol
e), etofenprox, etrimfos, fenitrothione
n), fenobucarb, fenoxycarb, fenpropathri
n), fenvalerate, fipronil, flucythrinat
e), flufenoxuron, flufenprox, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion
ion), furathiocarb, halofenozide, hexaflumuron (hexaflumur)
on), hydramethylnon, imidacloprid, isofenphos
os), indoxacarb, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion
n), metal dehydrate (metaldehyde), methamidophos (me
thamidophos), methidathion, methacrifos, metal carbs
b), Methomyl, Methoprene
e), methoxychlor, methoxyfenozide, monocrotophos (monoc
rotophos, muscalure, nitenpyram, omethoate, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-parathion-methyl, permethrin.
hrin), phenthoate, phoxim, phorate, phosalo
ne), phosmet, phosphamidon (phosp)
hamidon), pirimicarb (pirimicarb), pirimiphos-methyl (pirimiphos-methyl), prophenofos (pro)
fenofos), pymetrozine (pymetrozine), pyraclofos (pyraclofos), pyriproxyfen (pyriproxyfe)
n), rotenone, sulprofos (sulprofo)
s), silafluofen (silafluofen), spinosad (spinosad), sulfotep (sulfotep), tebufenozide (tebfenozide), teflubenzuron (teflubenzur)
on), tefluthorin, terbufos (ter)
bufos), tetrachlorvinpho
s), thiodicarb, thiamethoxam (t
hiamethoxam), thiofanox, thiometon, tolfenpyra
d), tralomethrin, trichlorfon, triazuron, triflumuron and vamidotion.
hion) etc.

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but is generally 0.00 per hectare (ha) as the active ingredient amount.
About 5 to 50 kg is suitable.

Next, formulation examples of preparations using the compound of the present invention are shown. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight. [Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Examples of other materials include anticaking agents and decomposition inhibitors. [Emulsion] Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Examples of other materials include, for example, spreading agents, decomposition inhibitors and the like. [Suspension] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Examples of other materials include antifreezing agents and thickeners. [Granule wettable powder] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts As other materials, for example, a binder, a decomposition inhibitor and the like can be mentioned. [Liquid formulation] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Other examples include antifreezing agents and spreading agents. [Granule] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Examples of other include a binder and a decomposition inhibitor. [Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, an anti-drift agent and an anti-decomposition agent.

When used, the above formulation was diluted with water to 1-100.
Spray with or without diluting 00 times.

Examples of the method for applying the compound of the present invention include foliar application, soil treatment, seed disinfection, etc., but it is also effective in general methods generally used by those skilled in the art.

[0272]

EXAMPLES Synthesis examples of the compounds of the present invention are shown below as Examples, but the present invention is not limited thereto.

Example 1 Methyl 2- (1,3-dimethyl-4- (aza (5-methyl-4-phenyl-2,5-thiazolinylidene) methyl) pyrazol-5-yl) acetic acid (the compound of the present invention I-1)
Synthesis of methyl 2- (1,3-dimethyl-4-(((methylamino) thioxomethyl) amino) pyrazol-5-yl) acetic acid 512 mg (2 mmol) in 2 ml of N, N-
It was dissolved in dimethylformamide, and 398 mg (2 mmol) of phenacyl bromide was added thereto. 3 at 80 ° C
After heating and stirring for an hour, the reaction mixture was mixed with 10 ml of water and 1
2.5 ml of a normal sodium hydroxide aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (chloroform).
The target methyl 2- (1,3-dimethyl-) is obtained by washing with diisopropyl ether.
4- (aza (5-methyl-4-phenyl-2,5-thiazolinylidene) methyl) pyrazol-5-yl) acetic acid 3
50 mg was obtained as colorless crystals. Melting point: 100-101 ° C. [Example 2] Methyl 2- (2- (aza (5-methyl-4- (4-methyl-phenyl) -2,5-oxathiolenylidene) methyl) -1-naphthyl) Synthesis of acetic acid (inventive compound II-1) Methyl 2- (2-(((dimethylamino) thioxomethyl) amino) -1-naphthylacetic acid 0.8 g (2.65
mmol) in 2 ml of dioxane, to which 4-
Methylphenyl 1-bromoethylketone 0.66 g
(2.9 mmol) was added. After heating and stirring at 105 ° C. for 3 hours, the solvent was distilled off, 10 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform) and further washed with diisopropyl ether to give the desired methyl 2- (2- (aza (5-methyl-4- (4-methyl-phenyl)). -2,5-oxathiolenylidene) methyl) -1-naphthyl) acetic acid 0.58
g was obtained as colorless crystals. Melting point: 118-119 ° C. [Example 3] Methyl (4- (4- (2,6-difluoro-phenyl) -5-methyl- [1,3] -dithiol-2-ylideneamino) -2,5-dimethyl -2H-pyrazole-
Synthesis of 3-yl) -acetic acid (inventive compound III-1) (4- (2,6-difluoro-
Phenyl) -5-methyl- [1,3] dithiol-2-
Ylidene) -dimethyl-ammonium sulfate 1.61
g (4.37 mmol) and methyl 1,3-dimethyl-4-aminopyrazol-5-yl-acetic acid 0.8 g
(4.37 mmol) of 1,2-dichloroethane (8 ml)
Suspended in 0.89 g of triethylamine (8.7
4 mmol) was added. After stirring under heating under reflux, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was washed with diisopropyl ether to give the desired methyl (4- (4- (2,6-difluoro-
Phenyl) -5-methyl- [1,3] -dithiol-2
0.7 g of -ylideneamino) -2,5-dimethyl-2H-pyrazol-3-yl) -acetic acid was obtained as colorless crystals.

Melting point: mp 103-106 ° C. [Example 4] Methyl 2- (3- (aza (5-methyl-4- (4-trifluoromethyl-phenyl) -2,5-oxathiolenylidene) methyl) Synthesis of 2-thiophene) acetic acid (inventive compound II-18) Methyl 3- (2-(((dimethylamino) thioxomethyl) amino) -2-thienylacetic acid obtained in Reference Example 10 290 mg (1.14 mmol) Was dissolved in 10 ml of 1,4-dioxane, and 0.33 g of 4-trifluoromethylphenyl 1-bromoethyl ketone (1.
14 mmol) was added. After heating and stirring at 100 ° C. for 2 hours, the solvent was distilled off, 10 ml of water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 5: 1) to give the target methyl 2
-(3- (aza (5-methyl-4- (4-trifluoromethyl-phenyl) -2,5-oxathiolenylidene))
Methyl) -2-thiophene) acetic acid (260 mg) was obtained as colorless crystals.

Melting point: 92-93 ° C. [Reference Example 1] Synthesis of dimethyl (1,3-dimethyl-4-nitropyrazol-5-yl) malonic acid 7.9 g (60 mmol) of dimethyl malonate was added to N, N-.
Dissolved in 100 ml of dimethylformamide, to which 12.4 g (90 mmol) of anhydrous potassium carbonate and 1,3
-Dimethyl-4-nitro-5-chloropyrazole 5.3
g (30 mmol) was added, and the mixture was stirred at 100 ° C. for 5 hours. The reaction mixture was poured into 100 ml of water, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off and the precipitated crystals were washed with diisopropyl ether to give 3.9 g of dimethyl (1,3-dimethyl-4-nitropyrazol-5-yl) malonic acid as a pale yellow oil. Obtained. Melting point: 78-79 ° C [Reference Example 2] methyl 1,3-dimethyl-4-nitropyrazole-5
Synthesis of -yl-acetic acid 3.7 g (13.7 mmol) of dimethyl (1,3-dimethyl-4-nitropyrazol-5-yl) malonic acid was dissolved in 60 ml of dimethyl sulfoxide, and 1.16 g of anhydrous lithium chloride ( 27.3 mmo) and water 0.
25 g was added, and the mixture was heated with stirring at 100 ° C. for 2 hours. The reaction mixture was poured into 100 ml of water, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off to give methyl 1,3-dimethyl-4-nitropyrazole-5-
2.6 g of yl-acetic acid was obtained as a pale yellow oil.

Reference Example 3 Synthesis of methyl 2- (1,3-dimethyl-4-(((methylamino) thioxomethyl) amino) pyrazol-5-yl) acetic acid Methyl 1,3-dimethyl-4-nitropyrazole -5
1.8 g (8.5 mmol) of -yl-acetic acid was dissolved in 10 ml of methanol, and 5% palladium-activated carbon (0.1%) was added thereto.
After adding 1 g, the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. After the palladium-activated carbon was filtered off, methanol was distilled off under reduced pressure to obtain 1.1 g of methyl 1,3-dimethyl-4-aminopyrazol-5-yl-acetic acid as a pale yellow oily substance.

Subsequently, 1 g of the obtained methyl 1,3-dimethyl-4-aminopyrazol-5-yl-acetic acid (5.
5 mmol) was dissolved in 10 ml of anhydrous tetrahydrofuran, and 0.4 g (5.5 m) of methyl isothiocyanate was dissolved therein.
mol) and triethylamine 0.56 g (5.5 m)
mol) was added and the mixture was stirred at room temperature. After 96 hours, the solvent was evaporated under reduced pressure, 10 ml of water was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and then dried over anhydrous magnesium sulfate. After filtration,
The solvent was distilled off under reduced pressure, and the resulting residue was washed with a mixed solvent of diethyl ether and diisopropyl ether to give methyl 2- (1,3-dimethyl-4-).
1.1 g of (((methylamino) thioxomethyl) amino) pyrazol-5-yl) acetic acid was obtained as colorless crystals.

Melting point: 138-139 ° C. [Reference Example 4] Synthesis of 2-nitro-1-naphthyl trifluoromethanesulfonic acid ester 2-nitro-1-naphthyl alcohol 5 g (26.44)
(mmol) was dissolved in 60 ml of methylene chloride and cooled to 0 ° C. To this, 2.54 g of pyridine (32.15 mmo
l) and trifluoromethanesulfonic anhydride 8.21
g (29.1 mmol) was added, and the mixture was stirred for 4 hours and 30 minutes. The reaction mixture was poured into ice water, extracted with chloroform, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to give 2-nitro-1-naphthyl trifluoromethanesulfonic acid ester as a brown oil. 6.1
g was obtained.

Reference Example 5 Synthesis of dimethyl 2- (2-nitro-1-naphthyl) malonic acid Sodium hydride washed with hexane 2.31 g (5
2.9 mmol) to N, N-dimethylformamide 46
9.14 g of dimethyl malonate (69.2)
4 mmol) in N, N-dimethylformamide (20 ml)
What was melt | dissolved in was added. After stirring at room temperature for 1 hour and 30 minutes, 2-nitro-1-naphthyl trifluoromethanesulfonic acid ester dissolved in 20 ml of N, N-dimethylformamide was added, and the mixture was further stirred at room temperature for 14 hours. The reaction mixture was poured into a mixed solution of 1N hydrochloric acid and ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated to obtain 12.5 g of the target dimethyl 2- (2-nitro-1-naphthyl) malonic acid as a crude product. [Reference Example 6] Synthesis of methyl 2- (2-nitro-1-naphthyl) acetic acid 12.5 g (41.25 mmol) of dimethyl 2- (2-nitro-1-naphthyl) malonic acid as a crude product was added to 30 ml of acetic acid. Dissolve and add 30 ml of hydrochloric acid to this,
The mixture was heated and stirred at ℃ for 8 hours. The reaction mixture is cooled and the precipitated crystals are filtered to give 2- (2-nitro-).
4.2 g of 1-naphthyl) acetic acid was obtained as pale yellow crystals.

The subsequently obtained 2- (2-nitro-1)
-Naphthyl) acetic acid was dissolved in 60 ml of methanol, 1.2 g of concentrated sulfuric acid was added thereto, and the mixture was heated under reflux. Two hours later,
The solvent was evaporated, 100 ml of water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. By purifying the obtained residue by silica gel column chromatography (ethyl acetate: n-hexane = 1: 5),
2.6 g of the target methyl 2- (2-nitro-1-naphthyl) acetic acid was obtained as pale yellow crystals.

Reference Example 7 Synthesis of methyl 2- (2-amino-1-naphthyl) acetic acid Methyl 2- (2-nitro-1-naphthyl) acetic acid 2.5
g (13.3 mmol) was dissolved in 30 ml of methanol, 0.1 g of 5% palladium-activated carbon was added thereto, and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 hours and 30 minutes. After removing palladium-activated carbon by filtration, methanol was distilled off under reduced pressure to give methyl 2- (2-amino-1-naphthyl).
2.34 g of acetic acid was obtained as a brown oil.

Reference Example 8 Synthesis of methyl 2- (2-(((dimethylamino) thioxomethyl) amino) -1-naphthylacetic acid Thiocarbonyldiimidazole 1.68 g (9.4 mm
was dissolved in 10 ml of N, N-dimethylformamide and cooled to 5 ° C. Subsequently, 1.94 g (9 mmol) of methyl 2- (2-amino-1-naphthyl) acetic acid was added, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Furthermore, 40%
Dimethylamine aqueous solution 1.22 g (10.8 mmol)
Was added and the mixture was further stirred for 1 hour. The solvent was distilled off under reduced pressure,
10 ml of water was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the resulting residue was washed with a mixed solvent of diethyl ether and diisopropyl ether to give methyl 2- (2-(((dimethylamino) thioxomethyl)).
2 g of amino) -1-naphthyl acetic acid was obtained as black crystals.

Reference Example 9 (4- (2,6-difluoro-phenyl) -5-methyl- [1,3] dithiol-2-ylidene) -dimethyl-
Synthesis of ammonium sulfate sodium dimethyldithiocarbamate dihydrate 7.9
80 g of acetonitrile with 3 g (44.33 mmol)
1-bromo-1- (2,6-difluoro-phenyl) -propan-2-one 10.03 g (4
0.3 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, 100 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline,
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. Subsequently, 13 ml of concentrated sulfuric acid was added to the residue and the mixture was mixed at room temperature for 1
Stir for hours. 1.5 l of ethyl acetate was poured into the reaction mixture, and the precipitated crystals were collected by filtration to obtain (4- (2,
6-difluoro-phenyl) -5-methyl- [1,3]
10 g of dithiol-2-ylidene) -dimethyl-ammonium sulfate was obtained as colorless crystals.

Reference Example 10 Synthesis of methyl 3- (2-(((dimethylamino) thioxomethyl) amino) -2-thienylacetic acid 2-chloro-3-nitrothiophene 3 g (18.34 m)
mol), dimethyl malonate 3.63 g (27.51 m)
mol), 4.97 g (36 mmol) of potassium carbonate and 30 ml of N, N-dimethylformamide are mixed,
The mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into a 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give dimethyl 2-
(3-Nitrothiophen-2-yl) malonic acid was obtained.

0.46 g (1.78 mm) of the obtained dimethyl 2- (3-nitrothiophen-2-yl) malonic acid was obtained.
ol) in 2 ml of acetic acid and 2 ml of concentrated hydrochloric acid is added to 100
The mixture was heated and stirred at 0 ° C for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After drying the ethyl acetate layer over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure to give 2-
320 mg of (3-nitrothiophen-2-yl) acetic acid was obtained.

The obtained 2- (3-nitrothiophene-2)
320 g (1.75 mmol) of -yl) acetic acid was dissolved in 5 ml of methanol, 1 drop of concentrated sulfuric acid was added thereto, and the mixture was stirred under reflux for 1 hour. Methanol was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to remove methyl 2
300 mg of-(3-nitrothiophen-2-yl) acetic acid
Got

300 mg (1.52 mmol) of the obtained methyl 2- (3-nitrothiophen-2-yl) acetic acid was obtained.
Dissolved in 15 ml of methanol, 0.45 g
(4.5 mmol) and potassium borohydride 0.5
4 g (10 mmol) was added, and the mixture was stirred at room temperature for 15 minutes. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was added to a solution of 0.29 g (1.62 mmol) of 1,1-thiocarbonyldiimidazole in 5 ml of N, N-dimethylformamide at 0 ° C., and the mixture was stirred at room temperature for 45 minutes. Next, 0.27 g of 50% aqueous methylamine solution was added to the reaction mixture, and the mixture was further stirred at room temperature for 30 minutes.
The reaction mixture was poured into 1N hydrochloric acid, extracted with ethyl acetate, the ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give methyl 2- (3-
(((Dimethylamino) thioxomethyl) amino) -2
-290 mg of thienylacetic acid were obtained.

Next, Tables 6 to 8 show the physical properties and the like of the compounds of the general formula (1) produced according to these methods.
The abbreviations in the table are as described above, from Het1 to Het2.
1 and Ta1 to Ta4 represent the following.

[0289]

[Chemical 74]

[0290]

[Chemical 75]

[Table 6]

[0292]

[Chemical 76]

[0293]

[Table 6] ――――――――――――――――――――――――――――――――――― No. Y ¹ Y ² Het T Physical properties (mp etc.) ――――――――――――――――――――――――――――――――――― I-1 H Ph Het1 CH ₂ COOMe mp100-101 ℃ I-2 H 2,6-F ₂ -Ph Het1 CH ₂ COOMe mp146-147 ℃ I-3 H Ph Het5 CH ₂ COOMe n _D20.2 1.5244 I-4 H 2,6 -F ₂ -Ph Het6 CH ₂ COOMe mp131-132 ℃ I-5 H Ta2 Het2 CH ₂ COOMe n _D21.4 1.5161 ――――――――――――――――――――――――― ―――――――――――― [Table 7]

[0294]

[Chemical 77]

[0295]

[Table 7] ――――――――――――――――――――――――――――――――――― No. Y ¹ Y ² Het T Physical properties (mp etc.) ――――――――――――――――――――――――――――――――――― II-1 Me 4-Me-Ph Het6 CH ₂ COOMe mp 118-119 ° C II-2 Me 4-CF ₃ -Ph Het6 CH ₂ COOMe mp143.5-144 ° C II-3 Me 4-CF ₃ -Ph Het1 CH ₂ COOMe mp133.5 -134 ℃ II-4 Me 4-Me-Ph Het1 CH ₂ COOMe mp74-76 ℃ II-5 Me 4-CF ₃ -Ph Het3 CH ₂ COOMe mp100.5-101 ℃ II-6 Me 4-Me-Ph Het3 CH ₂ COOMe mp80-83 ℃ II-7 Me 2-F-4-CF ₃ -Ph Het3 CH ₂ COOMe mp88-89 ℃ II-8 Me 4-Me-Ph Het3 CH ₂ CONHMe mp166-167 ℃ II-9 Me 4-CF ₃ -Ph Het2 CH ₂ COOMe mp118.5-119.5 ℃ II-10 Me 4-Me-Ph Het2 CH ₂ COOMe oil II-11 Me 4-CF ₃ -Ph Het4 CH ₂ COOMe mp164-165 ℃ II- 12 Me 4-Me-Ph Het4 CH ₂ COOMe mp113-114 ℃ II-13 Me 4-Me-Ph Het5 CH ₂ COOMe oil II-14 Me 4-CF ₃ -Ph Het5 CH ₂ COOMe oil II-15 Me 4- Me-Ph Het7 CH ₂ COOMe mp158-160 ℃ II-16 Me 4-Me-Ph Het8 CH ₂ COOMe mp127-129 ℃ II-17 Me 4-Ph Het9 CH ₂ COOMe mp143-145 ℃ II-18 Me 4 -CF ₃ -Ph Het10 CH ₂ COOMe mp9 2-93 ℃ II-19 Me Ta1 Het2 CH ₂ COOMe mp89-90 ℃ II-20 Me PhNHC (O) Het2 CH ₂ COOMe mp69-70 ℃ II-21 Me 4-t-Bu-Ph Het2 CH ₂ COOMe n _D21.4 1.5153 II-22 Me 4-Cl-Ph Het2 CH ₂ COOMe n _D22.0 1.5473 II-23 Me 2-F-4-CF ₃ -Ph Het2 CH ₂ COOMe n _D21.4 1.5182 II-24 Me 3-F-4-CF ₃ -Ph Het2 CH ₂ COOMe n _D21.4 1.5190 II-25 Me 4-Cl-Ph Het3 CH ₂ COOMe mp 90-93 ℃ II-26 Me 4-t-Bu-Ph Het3 CH ₂ COOMe n _D23.9 1.4298 II-27 Me 3,4-F ₂ -Ph Het3 CH ₂ COOMe n _D21.8 1.4688 II-28 Me 3-F-4-CF ₃ -Ph Het3 CH ₂ COOMe mp116-119 ℃ II-29 Me 4-Me-Ph Het10 CH ₂ COOMe mp103-103.5 ℃ II- 30 Me 4-Cl-Ph Het10 CH ₂ COOMe mp 95.5-96 ℃ II-31 Me 4-t-Bu-Ph Het10 CH ₂ COOMe n _D24.0 1.5037 II-32 Me 3,4-F ₂ -Ph Het10 CH ₂ COOMe mp69-70 ℃ II-33 Me 2-F-4-CF ₃ -Ph Het10 CH ₂ COOMe n _D23.7 1.4419 II-34 Me 3-F-4-CF ₃ -Ph Het10 CH ₂ COOMe mp118. 5-119 ℃ II-35 Me 4-Me-Ph Het11 CH ₂ COOMe mp129-131 ℃ II-36 Me 4-Me-Ph Het12 CH ₂ COOMe mp140.5-141.5 ℃ II-37 Me 4-Me-Ph Het13 CH ₂ COOMe mp 158-160 ℃ II-38 Me 4-Me-Ph Het14 CH ₂ COOMe oil II-39 Me Ta2 Het10 CH ₂ COOMe n _D21.5 1.5344 II-40 Me Ta2 Het2 CH ₂ COOMe n _D21.5 1.5304 II-41 Me Ta2 Het3 CH ₂ COOMe mp157-158 ℃ II-42 Me PhNHC (O) Het10 CH ₂ COOMe mp100-101 ℃ II-43 Me Ta1 Het10 CH ₂ COOMe mp134- 135 ° C II-44 Me 4-Me-Ph Het15 CH ₂ COOEt mp109-111 ° C II-45 Me 4-Me-Ph Het15 CH ₂ COOMe mp129-131 ° C II-46 Me 4-CF ₃ -Ph Het10 CH ₂ COOMe mp113.5-114.5 ℃ II-47 Me 4-Me-Ph Het16 OCOOMe mp149.5-150.5 ℃ II-48 Me 4-Me-Ph Het17 CH ₂ COOMe mp167-170 ℃ II-49 Me 4-Me-Ph Het18 OCH ₂ COOMe mp182-184 ℃ II-50 Me 4-CF ₃ -Ph Het13 CH ₂ COOMe mp180-181 ℃ II-51 Me 4-Me-Ph Het19 CH ₂ COOMe mp166-167 ℃ II-52 Me 4-Me- Ph Het19 CH ₂ COOH mp171-175 ℃ II-53 Me 4-CF ₃ -Ph Het11 CH ₂ COOMe mp165-166 ℃ II-54 Me 4-Me-Ph Het20 CH ₂ COOMe oil contains 50% of II-6 II- 55 Me Ta4 Het3 CH ₂ COOMe n _D22.6 1.5440 II-56 Me 4-Me-Ph Het21 CH ₂ COOMe mp184-186 ℃ ――――――――――――――――――――――― ―――――――――――――― [Table 8]

[0296]

[Chemical 78]

[0297]

[Table 8] ――――――――――――――――――――――――――――――――――― No. Y ¹ Y ² Het T Physical properties (mp etc.) ――――――――――――――――――――――――――――――――――― III-1 Me 2,6-F ₂ -Ph Het1 CH ₂ COOMe mp 103-106 ℃ ―――――――――――――――――――――――――――――――――― -Next, formulation examples of the fungicide for agricultural and horticultural use containing the compound of the present invention as an active ingredient will be specifically shown, but the invention is not limited thereto. In addition, in the following formulation examples, "part" means part by weight. [Formulation Example 1] Emulsion Compound No. of the present invention I-1 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Sorpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) The following are uniformly mixed to form an emulsion. And At the time of use, the above emulsion is diluted 50 to 20000 times and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare. [Formulation Example 2] Wettable powder of the present compound No. I-1 25 parts Pyrophyllite 66 parts Sorpol 5039 4 parts (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex # 80D 3 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) Lignin Calcium sulfonate 2 parts or more are uniformly mixed and pulverized to obtain a wettable powder.

When using the above-mentioned wettable powder,
Diluted to 00 times and the amount of active ingredient is 0.0 per hectare
Sprinkle so that the amount becomes 05 to 50 kg. [Preparation Example 3] Powdered compound of the present invention No. I-1 3 parts Carplex # 80D 0.5 part (white carbon: Shionogi Pharmaceutical Co., Ltd. trade name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and pulverized to give a powder. At the time of use, the amount of the active ingredient is 0.005 to 5 per hectare.
Sprinkle so that it weighs 0 kg. [Formulation Example 4] Granules Compound No. of the present invention I-1 5 parts Bentonite 30 parts Talc 64 parts Calcium lignin sulfonate 1 part More than 1 part are uniformly pulverized, a small amount of water is added and mixed with stirring, granulated with an extrusion granulator, dried and granulated And At the time of use, the amount of the active ingredient of the above-mentioned granules is 0.
Spray so that the amount becomes 005 to 50 kg. [Formulation Example 5] Flowable agent Compound No. of the present invention I-1 25 parts Solpol 3353 5 parts (nonionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 1000C 0.5 part (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Zansan gum ( Natural polymer) 0.2 part Sodium benzoate 0.4 part Propylene glycol 10 parts Water 58.9 parts The above components except the active ingredient (the compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred well. After that, wet milling is performed with a sand mill to obtain a flowable agent. At the time of use, the flowable agent is diluted 50 to 20000 times so that the amount of the active ingredient is 0.005 to 50 k per hectare.
Disperse so that it becomes g. [Formulation Example 6] Granular wettable powder (dry flowable agent) of the present invention compound No. I-1 75 parts Hitenol NE-15 5 parts (anionic surfactant: Dai-ichi Kogyo Seiyaku Co., Ltd. trade name) Vanilex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name) Carplex # 80D 10 parts (white carbon: trade name of Shionogi Seiyaku Co., Ltd.) The above is uniformly mixed and finely pulverized, a small amount of water is added and mixed by stirring, granulated by an extrusion granulator, dried and dried. Use as a flowable agent. When using it, dilute it 50 to 20000 times with water, and the active ingredient is 0.005 to 5 per hectare.
Sprinkle so that it weighs 0 kg. [Test Example] The usefulness of the compound according to the present invention will be specifically described in the following test examples. However, it is not limited to these.

[Test Example 1] Wheat powdery mildew control effect test [0299] Wheat (variety: Norin 61) of 2.0 to 2.5 leaf stage grown in a pot with a diameter of 5.5 cm was treated with the compound emulsion of the present invention with water. 20 ml per pot was sprayed with a chemical solution diluted with 500 ppm and adjusted to 500 ppm.

One day after application, wheat powdery mildew (Ery)
spores of siphe graminis) were directly inoculated. Then, place in a greenhouse, measure the ratio of the lesion area formed 7 days after inoculation to the inoculated leaves, according to the following formula,
The control value was calculated.

[0301]

[Equation 1] Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area rate)] × 100 As a result, the following compounds showed a control value of 70 or more. Inventive Compound No. II-3, II-5, II-7, II-9, II-11, II-13,
II-14, II-17, II-18, II-21, II-22, II-23, II-24, II-25, II
-26, II-27, II-28, II-30, II-31, II-32, II-33, II-34, II-4
1, II-54, III-1 [Test Example 2] Wheat leaf rust control effect test Wheat (cultivar: Norin 61) of 2.0 to 2.5 leaf stage grown in a pot with a diameter of 5.5 cm. The invention compound emulsion was diluted with water and adjusted to 500 ppm, and 20 ml per pot was sprayed with a spray gun.

One day after spraying, wheat leaf rust (Pucc)
spore suspension of inia recondita (2 x 1
0 ⁵ / ml) was sprayed, temperature 20-25 ° C., humidity 95
I put it in the inoculation box more than% for 24 hours. Then place it in the greenhouse,
The lesion area formed 10 days after the inoculation was measured, and the control value was calculated according to the following formula.

[0303]

## EQU2 ## Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area rate)] × 100 As a result, the following compounds showed a control value of 70 or more. Inventive Compound No. I-1, II-1, II-3, II-4, II-5, II-6, II-
7, II-8, II-9, II-10, II-11, II-12, II-13, II-14, II-16, II
-18, II-21, II-22, II-23, II-24, II-25, II-26, II-27, II-2
8, II-29, II-30, II-31, II-32, II-33, II-34, II-35, II-36,
II-37, II-38, II-39, II-40, II-41, II-45, II-46, II-47, II
-50, II-51, II-52, II-53, II-54, III-1 [Test Example 3] Wheat wilt disease control test 2.0 to 2.5 leaves grown in a pot with a diameter of 5.5 cm To a wheat (cultivar: Altria) of the season, a chemical solution prepared by diluting the emulsion of the compound of the present invention with water to 500 ppm was sprayed with 20 ml per pot using a spray gun.

[0304] One day after the application, wilt fungus (Leptosp)
spore suspension of haera nodorum (2 x 10
⁽⁵ cells / ml) were sprayed and inoculated. Put the inoculated wheat in an inoculation box at a temperature of 18 to 20 ° C and a humidity of 95% or more for 7 to
The disease was promoted for 10 days. The ratio of the formed lesion area to the inoculated leaf was measured, and the control value was calculated according to the following formula.

[0305]

## EQU00003 ## Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area rate)] × 100 As a result, the following compounds showed a control value of 70 or more. Inventive Compound No. I-1, II-3, II-4, II-5, II-6, II-7, II-
8, II-10, II-11, II-12, II-13, II-14, II-18, II-19, II-20,
II-21, II-22, II-23, II-24, II-25, II-26, II-27, II-28, II
-29, II-30, II-31, II-32, II-33, II-34, II-35, II-37, II-3
8, II-39, II-40, II-41, II-45, II-47, II-50, II-51, II-54,
II-55, III-1 [Test Example 4] Cucumber downy mildew control effect test A 1.5 leaf stage cucumber (cultivar: Sagamihanjiro) grown in a pot with a diameter of 7 cm was diluted with the compound emulsion of the present invention with water. Then, the chemical solution adjusted to 500 ppm was sprayed with 20 ml per pot using a spray gun.

One day after spraying, cucumber downy mildew (Pseu)
A spore suspension of doperonospora cubensis (2 × 10 ⁵ cells / ml) was sprayed at a temperature of 20-
It was placed in an inoculation box at 25 ° C and a humidity of 95% or more for one day. Then, it was placed in a greenhouse and the ratio of the lesion area formed 7 days after inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula.

[0307]

## EQU00004 ## Control value = [1- (treatment area lesion area rate / non-treatment area lesion area rate)] × 100 As a result, the following compounds showed a control value of 70 or more.

Inventive Compound No. II-4, II-5, II-6, II-
7, II-8, II-11, II-12, II-13, II-14, II-18, II-21, II-25, I
I-26, II-28, II-29, II-30, II-31, II-32, II-33, II-34, II-
37, II-38, II-41, II-46, II-47, II-51, II-54, II-55, III-1

[0309]

INDUSTRIAL APPLICABILITY These compounds of the present invention have an excellent controlling activity against plant diseases and are safe for crops.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) A01N 43/54 A01N 43/54 B Z 43/56 43/56 A 43/653 43/653 N 43/713 43/713 43/78 43/78 F 101 101 C07D 327/04 C07D 327/04 409/12 409/12 411/12 411/12 417/12 417/12 (72) Inventor Hiroyuki Suzuki Minami Saitama Gunhaku, Saitama Prefecture 1470 Shiraoka, Okamachi Osamu Shiraoka, Institute of Biological Sciences, Nissan Kagaku Kogyo Co., Ltd. (72) Inventor, Fumio Hayasaka 1470, Shiraoka, Shiraoka, Minamisaitama-gun, Saitama F-Term, Nissan Biochemical Research Co., Ltd. 4C023 AA03 4C033 AC04 AC17 4C063 AA01 BB09 CC62 CC87 CC92 CC97 DD12 DD22 DD25 DD29 DD41 DD47 DD87 EE03 4H011 AA01 BB08 BB09 BB10 DA02 DA15 DA16 DD03

Claims (9)

[Claims] 1. Formula (1) [Chemical 1] [In the formula, A¹Is [Chemical 2] And Va, Vb, Vc and Vd are independent of each other.
Represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom,
Ve is a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or
Represents a single bond, provided that Va, Vb, Vc, Vd and V
At least one of e is a nitrogen atom, an oxygen atom, or
Is a sulfur atom, Va-Vb, Vb-Vc, Vc-V
The bonds of d and Vd-Ve are single bonds or double bonds, respectively.
However, hydrogen atom or Y bond to each atom
You may A²Is A²a to A²y [Chemical 3] [Chemical 4] Represents a group selected from G is G¹To G¹⁴ [Chemical 5] Represents a group selected from Z is -OR¹, -SR¹Or -NR²R³And B is -CH₂-, -C (= CH-OR^Four)-Or -C
(= N-OR^Four) -Is Y is Y'-D- (CH₂)_p-(Y is 2
When more than one, they may be the same or different. ), A¹of
The carbon atom is replaced by two Ys substituted on the same carbon atom.
With 1 to 1 oxygen atom, nitrogen atom or sulfur atom
3 to 7-membered ring which may contain 3 or C = Q¹Forming
Or Va and Vb, Vb and Vc, Vc and Vd
Or two substituents Y on Vd and Ve are joined together
Therefore, Va and Vb, Vb and Vc, Vc and Vd or Vd
And Ve along with carbon, nitrogen, oxygen and sulfur
One or more kinds of same or different selected from yellow atom
Child, which may be substituted with Y,
Form a 5- or 6-membered ring which may be condensed with one another, D is a single bond, -NR^Five-, -C (= Q²)-, -NR^Five
-C (= Q²)-, -C (= Q²) -C (= Q³)-,-
CR⁶= N-, -N = CR⁶-, -CR⁶= N-N = CR⁶
-, -N = CR⁶-ON = CR⁶-, -CR⁶= N-O
-, -CR⁶= N-O-CR⁶= N-O-, -O-N = C
R⁶-CR⁶= N-O-, -CR⁶= N-NR^Five-Or-
ON-CR = CR⁶-CR⁶= N-NR^Five−, Q¹, Q²And Q³Are independently = O, = S, = N
-R⁷Or = C (R⁸) (R⁹), And Q^FourAnd Q^FiveAre independently = O or = S, X¹And X³Are each independently halogen, C₁~ C₆Archi
Le, C₁~ C₆Haloalkyl, C₁~ C₆Alkoxy, C₁
~ C₆Haloalkoxy, C₁~ C₆Alkylthio, C₁~ C
₆Alkylamino, (C₁~ C₆Alkyl)₂Amino, NO
₂, CN, formyl, OH, SH, NU¹U², C₁~ C₆
Alkoxycarbonyl, C₁~ C₆Alkylcarbonyl,
C₁~ C₆Haloalkylcarbonyl, R^aHas been replaced by
Phenyl, R^aPheno optionally substituted with
Kish, R^aPhenylcarbonyl optionally substituted with
Or C₁~ C₆Alkylcarbonyloxy, X²Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl again
Is R^aPhenyl which may be substituted with X^FourIs halogen, C₁~ C₆Alkyl, C₁~ C₆Haloa
Rukiru, C₁~ C₆Alkoxy, C₁~ C₆Halo arcoki
Shi, C₁~ C₆Alkylthio, C₁~ C₆Alkylamino,
(C₁~ C₆Alkyl)₂Amino, NO₂, CN, Holmi
LE, OH, SH, NU¹U², C₁~ C₆Alkoxy carbo
Nil, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo al
Kircarbonyl, R^aPheny optionally substituted with
Le, R^aPhenoxy optionally substituted with R^aReplace with
Optionally phenylcarbonyl or C₁~ C₆A
It is alkenylcarbonyloxy (provided that it is a substituted X
^FourHowever, if there are two or more, they may be the same or different from each other.
Yes. ), R¹, R²And R^FourAre each independently a hydrogen atom, C₁~ C
₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₆Cycloa
Rukiru, C₁~ C₆Alkoxy C₁~ C₆Alkyl, C₁~
C₆Alkylsulfenyl C₁~ C₆Alkyl, R^aReplace with
Optionally phenyl C₁~ C₆Alkyl or R^a
Heteroaryl C optionally substituted with₁~ C₆Archi
Is R³Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Haloa
Rukiru, C₃~ C₆Cycloalkyl, C₁~ C₆Alkoxy
C₁~ C₆Alkyl, C₁~ C₆Alkylsulfenyl C₁
~ C₆Alkyl, R^aPhenyl optionally substituted with,
R^aPhenyl C optionally substituted with₁~ C₆Alkyl
Or R^aHeteroaryl C optionally substituted with₁~
C₆Alkyl, R^FiveAnd R⁶Are each independently halogen, C₁~ C₆Al
Kill, C₁~ C₆Haloalkyl, C₃~ C₆Cycloalk
Le, C₁~ C₆Alkoxy, C₁~ C₆Alkoxy C ₁~ C₆
Alkyl, C₁~ C₆Alkylsulfenyl C₁~ C₆Al
Kill, C₁~ C₆Haloalkoxy, C₁~ C₆Alkylsul
Phenyl, C₁~ C₆Alkylsulfinyl, C₁~ C₆A
Lucylsulfonyl, C₁~ C₆Haloalkylsulfeni
Le, C₁~ C₆Haloalkylsulfinyl, C₁~ C₆Halo
Alkylsulfonyl, C₂~ C₆Alkenyl, C₂~ C₆Ha
Low alkenyl, C₂~ C₆Alkenyloxy, C₂~ C₆Ha
Ralkenyloxy, C₂~ C₆Alkenylsulfeni
Le, C₂~ C₆Alkenylsulfinyl, C₂~ C₆Arche
Nylsulfonyl, C₂~ C₆Haloalkenylsulfeni
Le, C₂~ C₆Haloalkenylsulfinyl, C₂~ C₆Ha
Ralkenylsulfonyl, C ₂~ C₆Alkynyl, C₂~
C₆Haloalkynyl, C₂~ C₆Alkynyloxy, C₂~
C₆Haloalkynyloxy, C₂~ C₆Alkynyl sulf
C, C₂~ C₆Alkynylsulfinyl, C₂~ C₆A
Lucinylsulfonyl, C₂~ C₆Haloalkynyl sulfe
Nil, C₂~ C₆Haloalkynylsulfinyl, C₂~ C₆
Haloalkynylsulfonyl, NO₂, CN, formyl,
OH, SH, SCN, C₁~ C₆Alkoxycarbonyl,
C₁~ C₆Haloalkoxycarbonyl, C₁~ C₆Alkyl
Carbonyl, C₁~ C₆Haloalkylcarbonyl, C₁~
C₆Alkylcarbonyloxy, R ^aEven if replaced with
Good phenyl, R^aPhenyl C optionally substituted with₁
~ C₆Alkyl, R^aPhenyls optionally substituted with
Lefonil, R^aPhenyl C optionally substituted with₁~ C
₆Alkylsulfonyl, R^aHete optionally substituted with
Lower, R^aHeteroaryl optionally substituted with
Le C₁~ C₆Alkyl, R^aHete optionally substituted with
Lower arylsulfonyl, R^aMay be replaced with
Phenyl carbonyl, R^aPheny optionally substituted with
Le C₁~ C₆Alkylcarbonyl, R^aHas been replaced with
Good heteroarylcarbonyl or -NU¹U²And
, However, R⁶May be a hydrogen atom, R⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Haloa
Rukiru, C₃~ C₆Cycloalkyl, C₁~ C₆Arcoki
Shi, C₁~ C₆Alkoxy C₁~ C₆Alkyl, C₁~ C₆A
Rukylsulphenyl C₁~ C₆Alkyl, C₁~ C₆Archi
Lesulfonyl, C₁~ C₆Haloalkylsulfonyl, C₁
~ C₆Alkylcarbonyl, C₁~ C₆Haloalkylcal
Bonil, R^aPhenyl optionally substituted with R,^aSet in
Optionally substituted phenoxy, R^aHas been replaced with
Good phenyl C₁~ C₆Alkyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkoxy, R^aReplaced by
Optionally phenylsulfonyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkylsulfonyl, R^aso
Optionally substituted heteroaryl, R^aReplaced by
Optionally heteroaryloxy, R^aReplaced by
Optionally heteroaryl C₁~ C₆Alkyl, R^aSet in
Optionally substituted heteroarylsulfonyl, R^aso
Optionally substituted phenylcarbonyl, R^aReplace with
Optionally phenoxycarbonyl, R^aReplaced by
Optional phenyl C₁~ C₆Alkylcarbonyl,
R^aA heteroaryl carbon which may be substituted with
Le, R^aHeteroaryloxy optionally substituted with
Carbonyl or R^aHeteroa optionally substituted with
Reel C₁~ C₆Alkylcarbonyl, R⁸And R⁹Are each independently a hydrogen atom, halogen, C
₁~ C₆Alkyl, C₁~ C₆Alkoxy, C₁~ C₆Archi
Rusulfenyl, C₂~ C₆Alkenyl, NO₂, CN,
Formyl or C₁~ C₆Alkoxycarbonyl, R^TenIs a hydrogen atom, halogen, R¹⁴, -OR¹⁴, -SR
¹⁴, -SOR¹⁴, Or -SO₂R¹⁴And R¹¹Is a hydrogen atom, R¹⁴Or CN, R¹²Is a hydrogen atom or R¹⁴And R¹³Is a hydrogen atom, halogen, C₁~ C₆Alkyl, C₁
~ C₆Haloalkyl, C ₃~ C₆Cycloalkyl, C₁~ C
₆Alkoxy C₁~ C₆Alkyl, C₂~ C₆Alkenyl
Or C₂~ C₆Alkynyl, R¹⁴Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C
₂~ C₆Alkenyl, C ₂~ C₆Haloalkenyl, C₂~ C₆
Alkynyl, C₂~ C₆Haloalkynyl, C₃~ C₆Cyclo
Alkyl, C₁~ C₆Alkylcarbonyl or C₁~ C₆
Alkoxycarbonyl, Y'is halogen, R^bC optionally substituted with₁~ C
₁₂Alkyl, R^bC optionally substituted with₃~ C₆Shiku
Lower alkyl, R^bC optionally substituted with₂~ C₁₂Al
Kenil, R^bC optionally substituted with₂~ C₁₂Alkini
Le, R^bC optionally substituted with₁~ C₁₂Alkoxy,
R^bC optionally substituted with₁~ C₆Alkoxy C₁~ C
₆Alkoxy, R^bC optionally substituted with₂~ C₆Al
Kenyloxy, R^bC optionally substituted with₂~ C₆A
Lucinyloxy, R^bC optionally substituted with₁~ C₆
Alkylsulfenyl, R^bC optionally substituted with₂
~ C₆Alkenylsulfenyl, R^bEven if replaced with
Good C₂~ C₆Alkynylsulfenyl, R^bReplaced by
May be C₁~ C₆Alkylsulfinyl, R^bSet in
C that may be replaced₂~ C₆Alkenylsulfinyl,
R^bC optionally substituted with₂~ C₆Alkynyl sulf
Inyl, R^bC optionally substituted with₁~ C₆Alkyl
Sulfonyl, R^bC optionally substituted with₂~ C₆Al
Kenylsulfonyl, R^bC optionally substituted with₂~ C
₆Alkynylsulfonyl, R^bC optionally substituted with
₁~ C₆Alkoxycarbonyl, R^bEven if replaced with
Good C₁~ C₆Alkylcarbonyl, R^bHas been replaced by
May be C₁~ C₆Alkylcarbonyloxy, R^cSet in
Optionally substituted phenyl, R^cEven if replaced with
Good phenoxy, R^cPhenyl optionally substituted with
C₁~ C₆Alkyl, R^cPheny optionally substituted with
Le C₁~ C₆Alkoxy, R^cMay be replaced with
Phenylsulfonyl, R^cPheny optionally substituted with
Rusulfinyl, R^cPhenyl optionally substituted with
Sulfenyl, R^cPhenyl C optionally substituted with₁
~ C₆Alkylsulfenyl, R^cMay be replaced with
I Phenyl C₁~ C₆Alkylsulfinyl, R^cReplace with
Optionally phenyl C₁~ C₆Alkyl sulfoni
Le, R^cHeteroaryl optionally substituted with R,^cso
Optionally substituted heteroaryloxy, R^cSet in
Optionally substituted heteroaryl C₁~ C₆Alkyl,
R^cHeteroaryl C optionally substituted with₁~ C₆A
Rukoxy, R^cHeteroaryl optionally substituted with
Sulfinyl, R^cHeteroants that may be substituted with
Rusulphenyl, R^cHetero optionally substituted with
Arylsulfonyl, R^cHete optionally substituted with
Lower C₁~ C₆Alkylsulfenyl, R^cReplace with
Optionally substituted heteroaryl C₁~ C₆Alkylsul
Finil, R^cHeteroaryl optionally substituted with
C₁~ C₆Alkylsulfonyl, R^cEven if replaced with
Good phenyl carbonyl, R^cMay be replaced with
Phenylcarbonyloxy, R^cMay be replaced with
Phenoxycarbonyl, R^cMay be replaced with
Phenyl C₁~ C₆Alkylcarbonyl, R^cReplaced by
Optionally phenyl C₁~ C₆Alkylcarbonyl Oki
Shi, R^cA heteroarylcarbo optionally substituted with
Nil, R^cHeteroarylcarc which may be substituted with
Bonyloxy, R^cHeteroants that may be substituted with
Roxycarbonyl, R^cMay be replaced with
Terror aryl C₁~ C₆Alkylcarbonyl, R^cReplace with
Optionally substituted heteroaryl C₁~ C₆Alkylcal
Bonyloxy, NO₂, CN, formyl or naphthyl
And R^aIs halogen, C₁~ C₆Alkyl, C₁~ C₆Haloa
Rukiru, C₃~ C₆Cycloalkyl, C₁~ C₆Arcoki
Shi, C₁~ C₆Alkoxy C₁~ C₆Alkyl, C₁~ C₆A
Rukylsulphenyl C₁~ C₆Alkyl, C₁~ C₆Haloa
Lucoxy, C₁~ C₆Alkylsulfenyl, C₁~ C₆A
Ruquilsulfinyl, C₁~ C₆Alkylsulfonyl, C
₁~ C₆Haloalkylsulfenyl, C₁~ C₆Halo Archi
Rusulfinyl, C₁~ C₆Haloalkylsulfonyl, C
₂~ C₆Alkenyl, C₂~ C₆Haloalkenyl, C₂~ C₆
Alkenyloxy, C₂~ C₆Haloalkenyloxy, C
₂~ C₆Alkenylsulfenyl, C₂~ C₆Alkenyls
Rufinil, C₂~ C₆Alkenylsulfonyl, C₂~ C₆
Haloalkenylsulfenyl, C₂~ C₆Haloalkenyl
Sulfinyl, C₂~ C₆Haloalkenylsulfonyl, C
₂~ C₆Alkynyl, C₂~ C₆Haloalkynyl, C₂~ C₆
Alkynyloxy, C₂~ C₆Haloalkynyloxy, C
₂~ C₆Alkynylsulfenyl, C₂~ C₆Alkynils
Rufinil, C₂~ C₆Alkynylsulfonyl, C₂~ C₆
Haloalkynylsulfenyl, C₂~ C₆Haloalkynyl
Sulfinyl, C₂~ C₆Haloalkynylsulfonyl, N
O₂, CN, formyl, SH, OH, SCN, C₁~ C₆
Alkoxycarbonyl, C₁~ C₆Alkylcarbonyl,
C₁~ C₆Haloalkylcarbonyl, C₁~ C₆Alkyr
Rubonyloxy, phenyl or -NU¹U²And
R to replace^aIs 1 to 5 (provided that R is^aIs 2
If more than one, they may be the same or different from each other), R^bIs halogen, C₃~ C₆Cycloalkyl, C₁~ C₆
Alkoxy, C₁~ C₆Alkoxy C₁~ C₆Alkoxy,
C₁~ C₆Alkylsulfenyl C₁~ C₆Alkoxy, C
₁~ C₆Haloalkoxy, C₁~ C₆Alkylsulfeni
Le, C₁~ C₆Alkylsulfinyl, C₁~ C₆Alkyl
Sulfonyl, C₁~ C₆Haloalkylsulfenyl, C₁
~ C₆Haloalkylsulfinyl, C₁~ C₆Halo Archi
Lesulfonyl, C₂~ C₆Alkenyloxy, C₂~ C₆Ha
Ralkenyloxy, C₂~ C₆Alkenylsulfeni
Le, C₂~ C₆Alkenylsulfinyl, C₂~ C₆Arche
Nylsulfonyl, C₂~ C₆Haloalkenylsulfeni
Le, C₂~ C₆Haloalkenylsulfinyl, C₂~ C₆Ha
Ralkenylsulfonyl, C₂~ C₆Alkynyloxy,
C₂~ C₆Haloalkynyloxy, C₂~ C₆Alkynils
Luphenyl, C₂~ C₆Alkynylsulfinyl, C₂~
C₆Alkynylsulfonyl, C₂~ C₆Halo alkynyls
Luphenyl, C₂~ C₆Haloalkynylsulfinyl, C
₂~ C₆Haloalkynylsulfonyl, NO₂, CN, hol
Mill, OH, SH, SCN, C₁~ C₆Alkoxy carbo
Nil, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo al
Kircarbonyl, C₁~ C₆Alkylcarbonyloxy,
R^aPhenyl optionally substituted with R,^aReplaced by
Phenoxy, R^aMay be replaced with
Phenyl C ₁~ C₆Alkoxy, R^aMay be replaced with
Phenylsulfonyl, R^aMay be replaced with
Phenyl C₁~ C₆Alkylsulfonyl, R^aReplaced by
Optionally heteroaryl, R^aMay be replaced with
Heteroaryloxy, R^aMay be replaced with
Heteroarylsulfonyl, R^aMay be replaced with
Phenyl carbonyl, R^aMay be replaced with
Enoxycarbonyl, R^aMay be replaced with
Nil C₁~ C₆Alkylcarbonyl, R^aHas been replaced by
Optionally heteroarylcarbonyl, R^aReplaced by
Optionally heteroaryloxycarbonyl or R^a
Heteroaryl C optionally substituted with₁~ C₆Archi
Lecarbonyl or -NU¹U²Or acid
1 to 4 selected from elementary atom, nitrogen atom or sulfur atom
3 to 7 membered ring which may contain 4 heteroatoms
And replace it with R^bIs 1 to 8 (provided that R is^b
May be the same or different from each other when two or more), R^cIs halogen, R^bC optionally substituted with₁~ C
₁₂Alkyl, R^bC optionally substituted with₃~ C₆Shiku
Lower alkyl, R^bC optionally substituted with₂~ C ₁₂Al
Kenil, R^bC optionally substituted with₂~ C₁₂Alkini
Le, R^bC optionally substituted with₁~ C₁₂Alkoxy,
R^bC optionally substituted with₁~ C₆Alkoxy C₁~ C
₆Alkoxy, R^bC optionally substituted with₂~ C₆Al
Kenyloxy, R^bC optionally substituted with₂~ C₆A
Lucinyloxy, R^bC optionally substituted with₁~ C₆
Alkylsulfenyl, R^bC optionally substituted with₂
~ C ₆Alkenylsulfenyl, R^bEven if replaced with
Good C₂~ C₆Alkynylsulfenyl, R^bReplaced by
May be C₁~ C₆Alkylsulfinyl, R^bSet in
C that may be replaced₂~ C₆Alkenylsulfinyl,
R^bC optionally substituted with₂~ C₆Alkynyl sulf
Inyl, R^bC optionally substituted with₁~ C₆Alkyl
Sulfonyl, R^bC optionally substituted with₂~ C₆Al
Kenylsulfonyl, R^bC optionally substituted with₂~ C
₆Alkynylsulfonyl, R^bC optionally substituted with
₁~ C₆Alkoxycarbonyl, R^bEven if replaced with
Good C₁~ C ₆Alkylcarbonyl, R^bHas been replaced by
May be C₁~ C₆Alkylcarbonyloxy, NO₂,
CN, formyl, OH, SH, SCN, C₁~ C₆Arco
Xycarbonyl, C₁~ C₆Alkylcarbonyl, C₁~
C₆Haloalkylcarbonyl, C ₁~ C₆Alkyl carbo
Nyloxy, R^aPhenyl optionally substituted with R,^a
Phenoxy optionally substituted with R^aReplaced by
Phenyl C₁~ C ₆Alkyl, R^aReplaced by
Optionally phenyl C₁~ C₆Alkoxy, R^aReplace with
Optionally phenylsulfonyl, R^aReplaced by
Optionally phenylsulfinyl, R^aReplaced by
Phenylsulfenyl, R^aHas been replaced by
May be phenyl C₁~ C₆Alkylsulfenyl, R^a
Phenyl C optionally substituted with₁~ C₆Alkylsul
Finil, R^aPhenyl C optionally substituted with₁~ C
₆Alkylsulfonyl, R^aHete optionally substituted with
Lower, R^aHeteroaryl optionally substituted with
Roxy, R^aHeteroaryl optionally substituted with
C₁~ C₆Alkyl, R^aHetero optionally substituted with
Aryl C₁~ C₆Alkoxy, R^aEven if replaced with
Good heteroarylsulfinyl, R^aHas been replaced by
Optionally heteroarylsulfenyl, R^aReplaced by
Optionally heteroarylsulfonyl, R^aReplaced by
Optionally substituted heteroaryl C₁~ C₆Alkylsulf
R, R^aHeteroaryl C optionally substituted with₁
~ C₆Alkylsulfinyl, R^aMay be replaced with
Heteroaryl C₁~ C₆Alkylsulfonyl, R^aso
Optionally substituted phenylcarbonyl, R^aReplace with
Optionally phenylcarbonyloxy, R^aSet in
Optionally substituted phenoxycarbonyl, R^aReplace with
Optionally phenyl C₁~ C₆Alkyl Carboni
Le, R^aPhenyl C optionally substituted with₁~ C₆Al
Kircarbonyloxy, R^aMay be replaced with
Teloarylcarbonyl, R^aMay be replaced with
Heteroaryl carbonyloxy, R^aHas been replaced by
Optionally heteroaryloxycarbonyl, R^aReplace with
Optionally substituted heteroaryl C₁~ C₆Alkylcal
Bonil, R^aHeteroaryl C optionally substituted with₁
~ C₆Alkylcarbonyloxy or -NU¹U²And
R to replace^cIs 1 to 5 (provided that R is^c
May be the same or different from each other when two or more), U¹And U²Are each independently a hydrogen atom, C₁~ C₆Al
Kill, C₁~ C₆Haloalkyl, C₃~ C₆Cycloalk
Le, C₁~ C₆Alkoxy C₁~ C₆Alkyl, C₁~ C₆A
Rukylsulphenyl C₁~ C₆Alkyl, formyl, C₁
~ C₆Alkylsulfonyl, C₁~ C₆Haloalkyl sul
Honil, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Al
Kircarbonyl or C₁~ C₆Haloalkylcarbonyl
Or U¹And U²Together with oxygen source
1 to 4 selected from a child, a nitrogen atom or a sulfur atom
A 3 to 7 membered ring which may contain a hetero atom, n represents the number of substituents, is 0 to 4, and p represents the number of repetitions and is 0 to 2. ]]
Heterocyclic imino aromatic compound or its pesticide
Acceptable salt. 2. A ¹ is [Chemical 7] And d represents the number of substituents, 0 to 2, and e
Represents the number of substituents, is 0 to 3, f is the number of substituents, is 0 to 4, g is the number of substituents, is 0 to 5, and h is Represents the number of substituents, 0 to 6, i represents the number of substituents, 0 to 1,
j represents the number of substituents, 0 to 7, k represents the number of substituents, 0 to 8, and Ya and Y independently of each other are Y′-D- (CH ₂ ) _p -Or (however, Ya
When the total of Y and Y is 2 or more, Ya may be the same, Y may be the same, or Ya and Y may be the same or different. ), And 2 Y or Ya substituted on the same carbon atom of A ¹ may each contain 1 to 3 oxygen atoms, nitrogen atoms or sulfur atoms together with the carbon atoms 3 to 7
The heterocyclic imino aromatic compound according to claim ^1, which forms a member ring or C = Q ¹ and Ya may represent a hydrogen atom, or a pesticidally acceptable salt thereof. 3. The heterocyclic imino aromatic compound according to claim 1 or 2, wherein A ¹ represents a 5-membered heterocycle, or a pesticidally acceptable salt thereof. 4. A ¹ is represented by: The heterocyclic imino aromatic compound according to claim 1 or 2, wherein Y, Ya, d and f have the same meanings as in claim 2, or a pesticidally acceptable salt thereof. 5. Ya and Y are each independently Y'-D-.
(CH ₂ ) _p − (however, when the total of Ya and Y is 2 or more, Ya may be mutually Y, Y may be the same or different from each other) and A ¹ is With two Y or Ya substituted on the same carbon atom, an oxygen atom, a nitrogen atom or a sulfur atom is added to each carbon atom together with 1
A heterocyclic imino aromatic compound or a pesticidally acceptable salt thereof according to claim 2, 3 or 4 which forms a 3 to 7 membered ring which may contain 3 to 3 or C = Q ¹ . 6. The heterocyclic imino aromatic compound according to claim ¹ , wherein G represents G ¹ , or a pesticidally acceptable salt thereof. 7. The pesticide-acceptable salt is a hydrochloride, hydrobromide, hydroiodide, formate, acetate or oxalate salt. The salt according to 6. 8. A method according to claim 1, 2, 3, 4, 5, 6 or 7.
A pesticide containing, as an active ingredient, one or more kinds selected from the heterocyclic imino aromatic compounds described in 1 or their salts. 9. A method according to claim 1, 2, 3, 4, 5, 6 or 7.
A bactericide containing, as an active ingredient, one or more kinds selected from the heterocyclic imino aromatic compounds or salts thereof described in 1.