JP2012077078A - Novel triazolone derivative and pest control agent containing the same as active constituent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a safely-usable novel pest control agent exerting sure effect.SOLUTION: The novel pest control agent includes a triazolone derivative represented by formula as an active constituent. In the formula: Ris COR(wherein Ris a 1C-8C alkyl group or a phenyl group), SRor SNHR(wherein Ris a 1C-8C alkyl group or a phenyl group); Ris a hydrogen atom, COR(wherein Ris a 1C-8C alkyl group or a phenyl group) or SR(wherein Ris a 1C-8C alkyl group); and X is a nitrogen atom.

Description

  The present invention relates to a novel triazolone derivative and a pest control agent containing it as an active ingredient.

  Many pest control agents have been found so far, but new drugs are still required due to problems such as a decrease in drug sensitivity, long-lasting effects, and safety during use. In addition, treating the chemicals with soil, water, seeds, etc., and protecting the crops from pests in an osmotic manner, in terms of labor saving in agriculture, reduction of environmental burden, safety for workers, etc. This is the desired control method.

  The compounds represented by the following formula (a) have been known so far from Weed Science (1968), 16 (2), 152-158 (Non-patent Document 1), American College of Physicians, Bulletin (1968), 3 (2), 175-180 (Non-patent Document 2) and the like are known to have herbicidal activity, but their insecticidal activity is not known.

Formula (a)
In WO95 / 18123 (Patent Document 1), it is disclosed that the compound represented by the following formula (b) has insecticidal activity, but there is no suggestion about the compound of the present invention.

Formula (b)
Moreover, in WO95 / 18123 (patent document 1), although the compound shown by following formula (c) is disclosed, there is no description about the insecticidal activity.

Formula (c)
Further, in Izvestiya Vysshikh Uchebnykh Zavedenii, Tekhnologiya Tekstil'noi Promyshlennosti (1990), (4), 51-53 (Non-patent Document 3), a compound represented by the following formula (d) is disclosed, but its insecticidal activity There is no description about.

Formula (d)

WO95 / 18123

Weed Science (1968), 16 (2), 152-158 American College of Physicians, Bulletin (1968), 3 (2), 175-180 Izvestiya Vysshikh Uchebnykh Zavedenii, Tekhnologiya Tekstil’noi Promyshlennosti (1990), (4), 51-53

  It is to provide a novel pest control agent that has a certain effect and can be used safely.

  In order to solve the above problems, the present inventors have made the following formula (I) as the first invention.

Formula (I)
[Where
R ₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
CH ₂ -O-R ₃ ,
_{CH 2 -O-CO-R 3} ,
(In the above group, R ₃ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
COR ₄ ,
COOR ₄ ,
CONHR ₄ ,
COSR ₄ ,
(In the above group, R ₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ,
SOR ₅ ,
SOOR ₅ ,
SNHR ₅ ,
CSNHR ₅ ,
CSSR ₅ ,
(In the above group, R ₅ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6} ,
CH ₂ -O-R ₆ ,
(In the above group, R ₆ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇ ,
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ,
SOR ₈ ,
SOOR ₈ ,
SNHR ₈ ,
CSR ₈ ,
CSNHR ₈ ,
CSSR ₈ ,
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
NH ₂
NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CO−R ₉ ) ₂ ,
N− (COO−R ₉ ) ₂ ,
N− (COS−R ₉ ) ₂ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
NH-R ₁₀ ,
NH-S-R ₁₀ ,
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−R ₁₁ ,
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−NR ₁₂ R ₁₃ ,
(In the above group, R ₁₂ and R ₁₃ are each independently
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group) or
O−R ₁₄ ,
(In the above group, R ₁₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
X represents a nitrogen atom or CH], and provides a pest control agent comprising one or more compounds represented by the formula:

As a preferred embodiment of the pest control agent of the present invention,
R ₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
COR ₄ ,
COOR ₄ ,
CONHR ₄ ,
COSR ₄ ,
(In the above group, R ₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ,
SOR ₅ ,
SOOR ₅ ,
SNHR ₅ ,
CSSR ₅ ,
(In the above group, R ₅ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6} ,
CH ₂ -O-R ₆ ,
(In the above group, R ₆ represents an optionally substituted C 1-8 alkyl group),
COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇ ,
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ,
SOOR ₈ ,
CSR ₈ ,
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH ₂
NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH-R ₁₀ ,
N−S−R ₁₀ ,
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group)
N = CH−R ₁₁ ,
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group optionally substituted with a phenyl group),
N = CH−NR ₁₂ R ₁₃ ,
(In the above group, R ₁₂ and R ₁₃ each independently represent a C1-8 alkyl group which may be substituted), or
O-R ₁₄
(R ₁₄ may be substituted C1~8 alkyl group,
Represents a benzyl group optionally substituted with a phenyl group),
X is a pest control agent comprising at least one compound of formula (I) representing a nitrogen atom or CH.

As a more preferred embodiment,
R ₁ is a hydrogen atom, COR ₄ (R ₄ is an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ , or SNHR ₅ (R ₅ is substituted) An optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group),
R ₂ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6} ,
CH ₂ -O-R ₆ ,
(In the above group, R ₆ represents an optionally substituted C 1-8 alkyl group), COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇ ,
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ,
SOOR ₈ ,
CSR ₈ ,
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH ₂
NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH-R ₁₀ ,
N−S−R ₁₀
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−R ₁₁ ,
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group optionally substituted with a phenyl group),
N = CH-NR ₁₂ R ₁₃
(In the above group, R ₁₂ and R ₁₃ each independently represents an optionally substituted C 1-8 alkyl group), or
O-R ₁₄
(R ₁₄ may be substituted C1~8 alkyl group,
Represents a benzyl group optionally substituted with a phenyl group),
X is a pest control agent comprising at least one compound of formula (I) which is a nitrogen atom.
As a particularly preferred embodiment,
R ₁ is a hydrogen atom, COR ₄ (R ₄ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ , or SNHR ₅ (R ₅ is substituted) Represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group),
R ₂ is a hydrogen atom, COR ₇ (R ₇ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), or SR ₈ (R ₈ is optionally substituted) X represents a good C1-8 alkyl group), and X is a pest control agent comprising at least one compound of formula (I) which is a nitrogen atom.

  As the second invention, the following formula (I ′)

Formula (I ')
[In the formula
R ₁ 'is a hydrogen atom,
An optionally substituted C1-8 alkyl group, a phenyl group optionally substituted benzyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
COR ₄ ',
COOR ₄ ',
CONHR ₄ ',
COSR ₄ ',
(In the above group, R ₄ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ',
SOR ₅ ',
SOOR ₅ ',
SNHR ₅ ',
CSSR ₅ '
(In the above group, R ₅ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ ′ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
CH ₂ -O-CO-R ₆ ',
CH ₂ -O-R ₆ ',
(In the above group, R ₆ ′ represents an optionally substituted C1-8 alkyl group), COR ₇ ′,
COOR ₇ ',
CONHR ₇ ',
COSR ₇ ',
(In the above group, R ₇ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ '
SOOR ₈ '
CSR ₈ ''
(In the above group, R ₈ ′ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH ₂
NH-CO-R ₉ ',
NH-COO-R ₉ ',
NH-COS-R ₉ ',
NH-CSS-R ₉ ',
N− (CSS−R ₉ ′) ₂ ,
(In the above group, R ₉ ′ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH-R ₁₀ ',
NH-S-R ₁₀ ',
(In the above group, R ₁₀ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−R ₁₁ '
(In the above group, R ₁₁ 'is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group optionally substituted with a phenyl group),
N = CH−NR ₁₂ 'R ₁₃ '
(In the above group, R ₁₂ ′ and R ₁₃ ′ each independently represent a C1-8 alkyl group which may be substituted),
O−R ₁₄ '
(In the above group, R ₁₄ ′ is an optionally substituted C 1-8 alkyl group,
Represents a benzyl group optionally substituted with a phenyl group),
X represents a nitrogen atom or CH,
However, R ₁ ′ and R ₂ ′ do not represent a hydrogen atom or acetyl group at the same time, and R ₂ ′ does not represent NH ₂ when R ₁ ′ is an acetyl group.] And its salts.

As a preferred embodiment of the second invention,
R ₁ ′ represents a hydrogen atom, COR ₄ ′ (R ₄ ′ represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ ′, or SNHSR ₅ ′ ( SR ₅ ′ represents an optionally substituted C1-8 alkyl group or an optionally substituted phenyl group), R ₂ ′ represents a hydrogen atom, an optionally substituted C1-8 alkyl group, An optionally substituted C2-8 alkenyl group, a phenyl group optionally substituted benzyl group, an optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
CH ₂ -O-CO-R ₆ ',
CH ₂ -O-R ₆ ',
(In the above group, R ₆ ′ represents an optionally substituted C1-8 alkyl group), COR ₇ ′,
COOR ₇ ',
CONHR ₇ ',
COSR ₇ ',
(In the above group, R ₇ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group, a phenyl group on which the phenyl group may be substituted, an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ',
SOOR ₈ ',
CSR ₈ ',
(In the above group, R ₈ ′ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH ₂
NH-CO-R ₉ ',
NH-COO-R ₉ ',
NH-COS-R ₉ ',
NH-CSS-R ₉ ',
N− (CSS−R ₉ ′) ₂ ,
(In the above group, R ₉ ′ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH-R ₁₀ ',
N−S−R ₁₀ '
(In the above group, R ₁₀ ′ is an optionally substituted C 1-8 alkyl group,
A phenyl group that may be substituted, a phenyl- (C1-4 alkyl) group that may be substituted, or a 5- or 6-membered heterocycloalkyl group that may be substituted).
N = CH−R ₁₁ ',
(In the above group, R ₁₁ ′ is a hydrogen atom, an optionally substituted C1-8 alkyl group, an optionally substituted phenyl group, or an optionally substituted phenyl group (C1-4 alkyl). ) Represents a group)
N = CH−NR ₁₂ 'R ₁₃ '
(In the above group, R ₁₂ ′ and R ₁₃ ′ each independently represents an optionally substituted C1-8 alkyl group), or
O−R ₁₄ '
(R ₁₄ ′ is an optionally substituted C1-8 alkyl group,
Represents a benzyl group optionally substituted with a phenyl group),
X represents a nitrogen atom, provided that R ₁ ′ and R ₂ ′ are not simultaneously hydrogen atoms or acetyl groups at the same time, and when R ₁ ′ is an acetyl group, R ₂ ′ is NH ₂ There are provided triazolone derivatives and salts thereof.

As a particularly preferred embodiment,
R ₁ ′ represents a hydrogen atom, COR ₄ ′ (R ₄ ′ represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ ′, or SNHR ₅ ′ ( R ₅ represents an optionally substituted C 1-8 alkyl group or an optionally substituted phenyl group, R ₂ ′ represents a hydrogen atom, COR ₇ ′ (R ₇ ′ represents a substituted Or an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), or SR ₈ ′ (R ₈ ′ represents an optionally substituted C1-8 alkyl group), and X is Provided are a triazolone derivative and a salt thereof, which represent a nitrogen atom, but R ₁ ′ and R ₂ ′ do not simultaneously represent a hydrogen atom or simultaneously an acetyl group.

  As a third invention, a pest control method using a pest control agent comprising at least one triazolone derivative represented by the above formula (I) is provided.

  A fourth invention provides a method for controlling pests, which comprises applying a pest control agent comprising one or more triazolone derivatives represented by the above formula (I) to plants or soil. .

  The pest control agent comprising the triazolone derivative of the present invention exhibits an excellent control effect against agricultural and horticultural pests, sanitary pests, animal parasites, stored grain pests, clothing pests, house pests and unpleasant pests, Further, the pest control agent of the present invention is a pest control agent that exhibits an excellent effect even by osmotic transfer chemical treatment of pests, particularly agricultural and horticultural pests, and is reliable and safe to use.

  In the definitions of the above formulas (I) and (I ′), the “optionally substituted C1-8 alkyl group” refers to a linear, branched, cyclic or combination thereof having 1 to 8 carbon atoms. Alkyl group. When this alkyl group contains a branched or cyclic alkyl group, it is clear that the carbon number of the alkyl group they represent is 3 or more. Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, and a nitro group.

  In the definitions of the above formulas (I) and (I ′), the “optionally substituted C2-8 alkenyl group” is represented by a linear, branched, cyclic or combination thereof having 2 to 8 carbon atoms. An alkenyl group. When this alkenyl group contains a branched or cyclic alkyl group, it is clear that the carbon number of the alkenyl group represented by these is 3 or more. Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, and a nitro group.

  In the definitions of the above formulas (I) and (I ′), the “optionally substituted C2-8 alkynyl group” is a linear, branched, cyclic or combination thereof having 2 to 8 carbon atoms. An alkynyl group. When this alkynyl group contains a branched or cyclic alkyl group, it is clear that the carbon number of the alkynyl group represented by these is 3 or more. Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, and a nitro group.

  In the definitions of the above formulas (I) and (I ′), “an optionally substituted phenyl group”, “an optionally substituted phenyl- (C1-4 alkyl) group”, “a phenyl group Examples of the substituent which may be substituted on the benzyl group which may be substituted include a halogen atom, a C1-4 alkyl group which may be substituted with a halogen atom, and a C1 which may be substituted with a halogen atom. -4 alkoxy groups, hydroxyl groups, cyano groups, nitro groups.

  In the definitions of the above formulas (I) and (I ′), “optionally substituted aromatic 5- or 6-membered heterocyclic methyl group”, “optionally substituted aromatic 5-membered or 6-membered heterocyclic group” The term “aromatic 5-membered or 6-membered heterocycle” means, for example, pyridyl group, pyrimidinyl group, pyridazinyl group, furyl group, pyranyl group, thienyl group, pyrrolyl group, imidazolyl group, triazolyl group, thiazolyl group, etc. Examples of the substituent which may be substituted include a halogen atom, a C1-4 alkyl group which may be substituted with a halogen atom, a C1-4 alkoxy group which may be substituted with a halogen atom, a hydroxyl group, A cyano group and a nitro group are mentioned.

  In the definitions of the above formulas (I) and (I ′), the “5-membered or 6-membered heterocycloalkyl group” of the “optionally substituted 5- or 6-membered heterocycloalkyl group” means a morpholinyl group. , A pyrrolidinyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, and the like. The substituent which may be substituted is a halogen atom, a C1-4 alkyl group which may be substituted with a halogen atom, or a halogen atom. A C1-4 alkoxy group, a hydroxyl group, a cyano group, and a nitro group which may be used.

In the above formulas (I) and (I ′), the optionally substituted C1-8 alkyl group represented by R ₁ and R ₁ ′ is specifically a methyl group, an ethyl group, an isopropyl group, or cyclopropylmethyl. Group, trifluoromethyl group and the like, and an ethyl group is preferable.

In the above formulas (I) and (I ′), the benzyl group on which the phenyl group represented by R ₁ and R ₁ ′ may be substituted is specifically a benzyl group or a 2,4,6-trimethylbenzyl group. 4-trifluoromethoxybenzyl group and the like, preferably a benzyl group.

In the above formulas (I) and (I ′), the optionally substituted aromatic 5- or 6-membered heterocyclic methyl group represented by R ₁ and R ₁ ′ is specifically a 4-pyridylmethyl group 5-chloro-3-thiazolylmethyl group, 2-furanyl group, 6-chloro-3-pyridyl group and the like, preferably 6-chloro-3-pyridyl group.

In the above formulas (I) and (I ′), R ₁ and R ₁ ′ are CH ₂ —O—R ₃ , CH ₂ —O—CO—R ₃ , CH ₂ —O—R ₃ ′, CH ₂ —O 'when referring to, R ₃ and R _3' -CO-R ₃ may be substituted C1~8 alkyl group, optionally substituted C2~8 alkenyl group, may be substituted C2~8 Specific examples of R ₁ representing an alkynyl group include a methoxymethyl group, an ethoxymethyl group, an isopropyloxymethyl group, an acetyloxymethyl group, an isopropylcarbonyloxymethyl group, a cyclopropanecarbonyloxymethyl group, and the like. An isopropylcarbonyloxymethyl group and an ethoxymethyl group, more preferably an ethoxymethyl group.

In the above formulas (I) and (I ′), when R ₁ and R ₁ ′ represent COR ₄ , COOR ₄ , CONHR ₄ , COSR ₄ , COR ₄ ′, COOR ₄ ′, CONHR ₄ ′, COSR ₄ ′ , R ₄ and R ₄ ′ are an optionally substituted C1-8 alkyl group, an optionally substituted phenyl group, an optionally substituted benzyl group, an optionally substituted aromatic 5 A 5-membered or 6-membered heterocycle, an optionally substituted 5-membered or 6-membered heterocycloalkyl group, preferably an optionally substituted C1-8 alkyl group, an optionally substituted phenyl group; Specific examples of R ₁ and R ₁ ′ include an acetyl group, an n-pentylcarbonyl group, a cyclopropylcarbonyl group, a cyclohexylcarbonyl group, an isopropylcarbonyl group, a benzylcarbonyl group, a benzoyl group, and a 4-trifluoromethoxybenzoyl group. , 4-me Rubenzoyl group, pyrrolidine-1-carbonyl group, 2,6-difluorobenzoyl group, 2,6-dichlorobenzoyl group, pyrimidine-4-carbonyl group, 2,4,6-trimethylbenzoyl group, 3-pyridylcarbonyl group, Examples include isothiazole-4-carbonyl group, 4-morpholinylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group, and the like, preferably acetyl group and benzoyl group.

In the above formulas (I) and (I ′), R ₁ and R ₁ ′ are SR ₅ , SOR ₅ , SOOR ₅ , SNHR ₅ , CSNHR ₅ , CSSR ₅ , SR ₅ ′, SOR ₅ ′, SOOR ₅ ′ When SNHR ₅ ′, CSNHR ₅ ′, CSSR ₅ ′ are shown, R ₅ and R ₅ ′ are optionally substituted C1-8 alkyl groups, optionally substituted C2-8 alkenyl groups, substituted May be a C2-8 alkynyl group, an optionally substituted phenyl group, an optionally substituted phenyl- (C1-4 alkyl) group, an optionally substituted aromatic 5 or 6 membered Heterocycle, an optionally substituted 5- or 6-membered heterocycloalkyl group, preferably an optionally substituted C1-8 alkyl group, an optionally substituted phenyl group, or a phenyl group substituted Optionally substituted phenyl- (C1-4 alkyl) group, optionally substituted aromatic 5-membered Is a 6-membered heterocycle, more preferably optionally substituted C1~8 alkyl group or an optionally substituted phenyl group, a phenylthio Examples of specific R ₁ and R ₁ ' Group, 4-morpholinylthio group, di-n-butylaminothio group, n-hexylthio group, sec-butylthio group, cyclohexylthio group, 1-phenylpropan-2-ylthio group, tert-butylaminothio group, 4,4 , 4-trifluorobutan-2-ylthio group, isopropylthio group, isopropylsulfonyl group, isothiazol-4-carbonyl group, heptan-2-ylthio group, phenylsulfonyl group, heptane-4-ylthio group, 5H-tetrazole- 5-carbonyl group, 2H-imidazole-2-carbonyl group, methanesulfonyl group, tert-butylthio group, pyridin-3-ylmethylthio group, 6-chloro-pyridin-3-ylmethylthio group, etc. Preferably, n-hexylthio group, sec-butylthio group, cyclohexylthio group, 1-phenylpropan-2-ylthio group, tert-butylaminothio group, phenylthio group, isopropylthio group, 4,4,4-tri A fluorobutan-2-ylthio group, more preferably an n-hexylthio group, a sec-butylthio group, a cyclohexylthio group, a phenylthio group, an isopropylthio group, or a 4,4,4-trifluorobutan-2-ylthio group .

In the above formulas (I) and (I ′), preferred examples of R ₁ and R ₁ ′ are a hydrogen atom, COR ₄ and COR ₄ ′ (R ₄ and R ₄ ′ may be optionally substituted C 1-8. alkyl group, or an optionally substituted phenyl _{group,), SR 5, sNHR 5} , SR 5 ' or sNHR _5' (R ₅ and R ₅ ', optionally substituted C1~8 alkyl group, Or an optionally substituted phenyl group), specifically, an acetyl group, a 4-methylbenzoyl group, a cyclohexylcarbonyl group, a 3-pyridylcarbonyl group, a 4-morpholinylcarbonyl group, a benzylcarbonyl group. Benzoyl group, 2,6-difluorobenzoyl group, 4-trifluoromethoxybenzoyl group, 2,4,6-trimethylbenzoyl group, isopropylcarbonyl group, phenylthio group, n-hexylthio group, sec-butylthio group, 1-pyrrolidinylcarb Bonyl group, cyclohexylthio group, 4,4,4-trifluorobutan-2-ylthio group, isopropylthio group, heptan-2-ylthio group, heptan-4-ylthio group, tert-butylaminothio group, Preferred are acetyl group, benzoyl group, n-hexylthio group, sec-butylthio group, cyclohexylthio group, phenylthio group, isopropylthio group, and 4,4,4-trifluorobutan-2-ylthio group.

In the above formulas (I) and (I ′), the optionally substituted C1-8 alkyl group represented by R ₂ and R ₂ ′ specifically includes a methyl group, an ethyl group, an isopropyl group, trifluoromethyl. Group, tert-butyl group, n-hexyl group and the like, and an ethyl group is preferable.

In the above formulas (I) and (I ′), the optionally substituted C 2-8 alkenyl group represented by R ₂ and R ₂ ′ is specifically an allyl group, 3,3,3-trifluoro- Examples thereof include a 1-propenyl group and a 3-hexynyl group, and an allyl group is preferable.

In the above formulas (I) and (I ′), the phenyl group optionally substituted by the phenyl group represented by R ₂ and R ₂ ′ is specifically a benzyl group, a 4-trifluoromethoxybenzyl group, 2 2,4,6-trimethylbenzyl group, and the like, preferably a benzyl group.

In the above formulas (I) and (I ′), R ₂ and R ₂ ′ are CH ₂ —O—CO—R ₆ , CH ₂ —O—R ₆ , CH ₂ —O—CO—R ₆ ′, CH ₂ When —O—R ₆ ′ is represented, R ₆ and R ₆ ′ may be an optionally substituted C1-8 alkyl group, an optionally substituted C2-8 alkenyl group, an optionally substituted C2-8 Specific examples of R ₂ and R ₂ ′ include ethoxymethyl, isopropylcarbonyloxymethyl, allyloxymethyl, trifluoromethoxymethyl, sec-butyloxymethyl, acetyloxymethyl, cyclo Examples thereof include a propanecarbonyloxymethyl group, preferably an isopropylcarbonyloxymethyl group and an ethoxymethyl group.

In the above formulas (I) and (I ′), when R ₂ and R ₂ ′ represent COR ₇ , COOR ₇ , CONHR ₇ , COSR ₇ , COR ₇ ′, COOR ₇ ′, CONHR ₇ ′, COSR ₇ ′, R ₇ and R ₇ ′ are an optionally substituted C1-8 alkyl group, an optionally substituted C2-8 alkenyl group, an optionally substituted C2-8 alkynyl group, and optionally substituted. A phenyl group, a benzyl group in which the phenyl group may be substituted, a 5- or 6-membered heterocycloalkyl group that may be substituted, and preferably an optionally substituted C1-8 alkyl group, substituted An optionally substituted phenyl group, an optionally substituted benzyl group, an optionally substituted 5- or 6-membered heterocycloalkyl group, and specific examples of R ₂ and R ₂ ′ include , Acetyl group, benzylcarbonyl group, cyclohexylcarbo Group, 4-trifluoromethoxybenzoyl group, isothiazole-4-carbonyl group, 4-methylbenzoyl group, pyrrolidine-1-carbonyl group, 2,6-dichlorobenzoyl group, 2,4,6-trimethylbenzoyl group, 4H-pyrazole-4-carbonyl group, 2,6-difluorobenzoyl group, S-isopropylcarbothioate group, etc. are mentioned, preferably benzylcarbonyl group, cyclohexylcarbonyl group, 4-methylbenzoyl group, pyrrolidine-1-carbonyl Group, 2,6-dichlorobenzoyl group, 2,4,6-trimethylbenzoyl group.

In the above formulas (I) and (I ′), R ₂ and R ₂ ′ are SR ₈ , SOR ₈ , SOOR ₈ , SNHR ₈ , CSR ₈ , CSNHR ₈ , CSSR ₈ , SR ₈ ′, SOR ₈ ′, SOOR ₈ When indicating ', SNHR ₈ ', CSR ₈ ', CSNHR ₈ ', CSSR ₈ ', R ₈ and R ₈ ' are optionally substituted C1-8 alkyl groups, optionally substituted C2-8. An alkenyl group, an optionally substituted C2-8 alkynyl group, an optionally substituted phenyl group, an optionally substituted benzyl group, an optionally substituted aromatic 5 or 6 membered Heterocycle represents an optionally substituted 5-membered or 6-membered heterocycloalkyl group, preferably an optionally substituted C1-8 alkyl group. Specific examples of R ₂ and R ₂ ′ include sec-Butylthio group, isothiazol-4-ylthio group, methanesulfonyl group, phenylsulfonyl group, 4,4,4-trifluoro Tan-2-ylthio group, 1,2,4-triazol-3-one-2-ylthiocarbonyl group and the like, preferably sec-butylthio group, 1,2,4-triazol-3-one-2 -An ylthiocarbonyl group.

In the above formulas (I) and (I ′), R ₂ and R ₂ ′ are NH—CO—R ₉ , NH—COO—R ₉ , NH—COS—R ₉ , NH—CSS—R ₉ , N— ( _{CO-R 9) 2, N-} (COO-R 9) 2, N- (COS-R 9) 2, N- (CSS-R 9) 2, NH-CO-R 9 ', NH-COO-R ₉ ', NH-COS-R ₉ ', NH-CSS-R ₉ ', N- (CO-R ₉ ') ₂ , N- (COO-R ₉ ') ₂ , N- (COS-R ₉ ') ₂ , when N- (CSS-R ₉ ′) ₂ is represented, R ₉ and R ₉ ′ are optionally substituted C1-8 alkyl groups, optionally substituted C2-8 alkenyl groups, substituted An optionally substituted C2-8 alkynyl group, an optionally substituted phenyl group, an optionally substituted phenyl- (C1-4 alkyl) group, an optionally substituted aromatic 5 member or 6 A membered heterocycle, an optionally substituted 5- or 6-membered heterocycloalkyl group, preferably an optionally substituted C1-8 alkyl Group, a phenyl group which may be substituted, a specific R ₂ and R ₂ ', isopropyl carba mode dithioate group, S- isopropyl carba Mochio benzoate group, a pyrimidine-5-carboxamide group, 5H -Tetrazole-5 carboxyamide group, benzamide group, 2,6-difluorobenzamide group, n-hexanecarboxamide group, cyclohexanecarboxyamide group, ethoxycarbonylamino group, cyclopropanecarboxyamide group, etc., preferably n- Hexanecarbonylamide group.

In the above formulas (I) and (I ′), when R ₂ and R ₂ ′ represent NH—R ₁₀ , NH—S—R ₁₀ , NH—R ₁₀ ′, NH—S—R ₁₀ ′, R ₁₀ and R ₁₀ ′ are an optionally substituted C1-8 alkyl group, an optionally substituted C2-8 alkenyl group, an optionally substituted C2-8 alkynyl group, an optionally substituted phenyl Group, phenyl- (C1-4 alkyl) group in which phenyl group may be substituted, aromatic 5-membered or 6-membered heterocycle optionally substituted, 5-membered or 6-membered optionally substituted A heterocycloalkyl group, preferably an optionally substituted C1-8 alkyl group, an optionally substituted phenyl group, an optionally substituted phenyl- (C1-4 alkyl) group, substituted a heterocyclic ring which may aromatic 5-membered or 6-membered optionally be, Oyo specific R ₂ As R ₂ 'is isopropyl thio group, isopropylamino group, 2,6-difluorobenzyl group, 3-pyridyl-methylamino group, neopentyl group, 1-phenylethyl group, cyclohexylamino group, n- hexylamino Group, phenylethylamino group, benzylamino group, phenylpropylamino group, cyclopropylmethylamino group, tetrahydro-2H-pyran-4-ylamino group, 5H-tetrazol-5-carbonyl group, 2H-imidazole-2-carbonyl group 1- (4-cyanophenyl) ethylamino group, 1- (4-methylphenyl) ethylamino group, 1- (4-fluorophenyl) ethylamino group, 5-acetamido-2-acetoxymethyl-3,4- Diacetoxy-tetrahydro-2H-pyran-6-yl-amino group, 1- (4-tert-butylphenyl) ethylamino group, phenylamino group, 1- (4-trifluoro Methylphenyl) ethylamino group, 2,2-dimethyl-1-phenylpropylamino group, 2,2,2-trifluoro-1-phenyl) ethylamino group, 1- (1-cyano-2,2,2- Trifluoro-1-phenyl) ethylamino group and the like, preferably benzylamino group, 5-acetamido-2-acetoxymethyl-3,4-diacetoxy-tetrahydro-2H-pyran-6-yl-amino group .

In the above formulas (I) and (I ′), when R ₂ and R ₂ ′ represent N═CH—R ₁₁ and N═CH—R ₁₁ ′, R ₁₁ and R ₁₁ ′ are substituted with a hydrogen atom. C1-8 alkyl group which may be substituted, C2-8 alkenyl group which may be substituted, C2-8 alkynyl group which may be substituted, phenyl group which may be substituted, phenyl group is substituted An optionally substituted phenyl- (C1-4 alkyl) group, an optionally substituted 5- or 6-membered heterocycloalkyl group, preferably a hydrogen atom, an optionally substituted C1-8 alkyl group, a substituted A phenyl group which may be substituted, a phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted, and specific examples of R ₂ and R ₂ ′ include an ethylideneamino group, a hexylideneamino group, 2-Phenylethylideneamino group, benzylide An amino group, a cyclopropylmethyleneamino group, a 3-phenylpropylideneamino group, a (1- (4-trifluoromethyl) phenyl) ethylideneamino group, and the like, preferably a hexylideneamino group, a cyclopropylmethyleneamino group, 3-phenylpropylideneamino group, (1- (4-trifluoromethyl) phenyl) ethylideneamino group.

In the above formulas (I) and (I ′), when R ₂ and R ₂ ′ represent N═CH—NR ₁₂ R ₁₃ , N═CH—NR ₁₂ ′ R ₁₃ ′, R ₁₂ , R ₁₃ , R ₁₂ ', R ₁₃ ' each independently represents an optionally substituted C1-8 alkyl group, an optionally substituted C2-8 alkenyl group, an optionally substituted C2-8 alkynyl group, or a substituted group. Optionally substituted phenyl group, optionally substituted benzyl group, optionally substituted aromatic 5- or 6-membered heterocycle, optionally substituted 5- or 6-membered heterocycloalkyl Group, preferably an optionally substituted C1-8 alkyl group, and specific examples of R ₂ and R ₂ ′ include (N-ethyl-N-trifluoromethylamino) -methyleneamino group, ( N-phenyl-N-methylamino) -methyleneamino group, dimethylaminomethyleneamino group, (N-methyl Le -N- pyrimidin-4-ylamino) - methylene amino group and the like, preferably dimethylaminomethyleneamino group.

In the above formulas (I) and (I ′), when R ₂ and R ₂ ′ represent O—R ₁₄ and O—R ₁₄ ′, R ₁₄ and R ₁₄ ′ may be optionally substituted C1-8. Alkyl group, optionally substituted C2-8 alkenyl group, optionally substituted C2-8 alkynyl group, optionally substituted phenyl group, phenyl group optionally substituted benzyl group, substituted An optionally substituted aromatic 5-membered or 6-membered heterocycle, an optionally substituted 5-membered or 6-membered heterocycloalkyl group, preferably an optionally substituted C1-8 alkyl group, a phenyl group Is an optionally substituted benzyl group. Specific examples of R ₂ and R ₂ ′ include methoxy group, isopropyloxy group, allyloxy group, 4-morpholinyloxy group, 5-pyrimidineoxy group, benzyloxy group, 3- And pyridyloxy group Of these, a methoxy group and a benzyloxy group are preferable.

In the above formulas (I) and (I ′), R ₂ and R ₂ ′ are preferably a hydrogen atom, an amino group, COR ₇ , COR ₇ ′ (R ₇ and R ₇ ′ are optionally substituted C 1- 8 alkyl group, optionally substituted C2-8 alkenyl group, optionally substituted C2-8 alkynyl group, optionally substituted phenyl group, phenyl group optionally substituted benzyl group, substituted Represents an optionally substituted 5- or 6-membered heterocycloalkyl group), NH—CO—R ₉ , NH—CO—R ₉ ′ (R ₉ and R ₉ ′ are optionally substituted C1— 8 alkyl group, optionally substituted C2-8 alkenyl group, optionally substituted C2-8 alkynyl group, optionally substituted phenyl group, phenyl group optionally substituted phenyl- (C1 ~ 4 alkyl) groups, optionally substituted aromatic 5 or 6 membered hetero Represents a heterocycloalkyl group of 5-membered optionally substituted or _{6-membered), NH-R 10, NH} -R 10 '(R 10 and R _10' is optionally substituted C1~8 alkyl Group, optionally substituted C2-8 alkenyl group, optionally substituted C2-8 alkynyl group, optionally substituted phenyl group, phenyl group optionally substituted phenyl- (C1-4 Alkyl) group, an optionally substituted aromatic 5- or 6-membered heterocycle, an optionally substituted 5- or 6-membered heterocycloalkyl group), or N = CH—R ₁₁ , N ═CH—R ₁₁ ′ (R ₁₁ and R ₁₁ ′ are a hydrogen atom, an optionally substituted C1-8 alkyl group, an optionally substituted C2-8 alkenyl group, an optionally substituted C2— 8 Alkynyl group, optionally substituted phenyl group, phenyl group substituted Which may be phenyl - a (C1 -4 alkyl) group, a heterocycloalkyl group 5- or 6-membered optionally substituted), more preferably a hydrogen atom, COR _7, COR ₇ '( R ₇ and R ₇ ′ represent an optionally substituted C1-8 alkyl group and an optionally substituted phenyl group), SR ₈ , SR ₈ ′ (R ₈ and R ₈ ′ are substituted) Specifically, a benzylcarbonyl group, a cyclohexylcarbonyl group, a 4-methylbenzoyl group, a 1-pyrrolidinylcarbonyl group, a 2,6-dichlorobenzoyl group, 2, 4,6-trimethylbenzoyl group, n-hexanecarbonylamide group, benzylamino group, hexylideneamino group, cyclopropylmethyleneamino group, 3-phenylpropylideneamino group, (1- (4-trifluoromethyl) phenyl) Ethylidenia Group, preferably a hydrogen atom, benzylcarbonyl group, cyclohexylcarbonyl group, 4-methylbenzoyl group, pyrrolidine-1-carbonyl group, 2,6-dichlorobenzoyl group, 2,4,6-trimethylbenzoyl group , Sec-butylthio group, particularly preferably a hydrogen atom.

  In the above formulas (I) and (I ′), X represents CH or a nitrogen atom, preferably a nitrogen atom.

In the above formula (I), as a preferred combination, R ₁ is a hydrogen atom, COR ₄ (R ₄ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ or SNHR ₅ (R ₅ represents an optionally substituted C1-8 alkyl group or an optionally substituted phenyl group), R ₂ is a hydrogen atom, COR ₇ (R ₇ is an optionally substituted C1~8 alkyl or optionally substituted represents a phenyl group), or SR _8, (R ₈ represents a C1~8 alkyl group which may be substituted), X Is a nitrogen atom. As a preferred specific combination, when X is a nitrogen atom, R ₂ is a hydrogen atom, R ₁ is a hydrogen atom, an acetyl group, a 3-pyridylcarbonyl group, a benzoyl group, a 2,6-difluorobenzoyl group, a 4-trifluoro group, Fluoromethoxybenzoyl group, 2,4,6-trimethylbenzoyl group, isopropylcarbonyl group, phenylthio group, n-hexylthio group, sec-butylthio group, cyclohexylthio group, 4,4,4-trifluorobutan-2-ylthio group , An isopropylthio group, a heptan-2-ylthio group, a heptane-4-ylthio group, and a tert-butylaminothio group. A particularly preferred specific combination is when X is a nitrogen atom and R ₂ is a hydrogen atom. R ₁ is a hydrogen atom, an acetyl group, a benzoyl group, an isopropylthio group, or a 4,4,4-trifluorobutan-2-ylthio group.

When the pest control agent represented by the above formula (I) is an animal parasitic pest control agent, as a preferred combination, R ₁ is a hydrogen atom, COR ₄ (R ₄ is an optionally substituted C ₁ -C ₁ SR ₅ , SNHR ₅ (R ₅ is an optionally substituted C 1-8 alkyl group, an optionally substituted phenyl group, or an optionally substituted phenyl group, or an optionally substituted phenyl group) Represents an optionally substituted 5- or 6-membered heterocycloalkyl group), an optionally substituted C1-8 alkyl group, a phenyl group optionally substituted benzyl group, or CH ₂ —OR ₃ (R ₃ is a representative) and optionally substituted C1~8 alkyl group, R ₂ represents a hydrogen atom, COR _{7 (R 7} may be substituted C1~8 alkyl group, or optionally substituted represents a phenyl group), SR ₈ (R ₈ is optionally substituted Represents an even or C1~8 alkyl group), optionally substituted C1~8 alkyl group, optionally substituted C2~8 alkenyl group, a benzyl group which may phenyl group substituted or CH _2, —OR ₃ (R ₃ represents an optionally substituted C 1-8 alkyl group), and X is a nitrogen atom. As a more preferred combination, R ₁ is a hydrogen atom or a methyl group, X is a nitrogen atom, R ₂ is an optionally substituted C 1-8 alkyl group, an optionally substituted C 2-8 alkenyl group, phenyl R ₂ is a hydrogen atom, X is a nitrogen atom, R ₁ is SR ₅ , SNHR ₅ (R ₅ is an optionally substituted C 1-8 alkyl group) Represents an optionally substituted phenyl group, or an optionally substituted 5- or 6-membered heterocycloalkyl group), or X is a nitrogen atom, and R ₁ and R ₂ are the same, COR ₄ (R ₄ represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), or CH ₂ —OR ₃ (R ₃ represents an optionally substituted C1— Represents an 8 alkyl group).

In the above formula (I ′), as a preferable combination, R ₁ ′ is a hydrogen atom, COR ₄ ′ (R ₄ ′ is an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group. the _{represented), SR 5 ', sNHR 5} ' (R 5 ' may be substituted C1~8 alkyl group, an optionally substituted phenyl group or substituted optionally a 5-membered or 6-membered, Represents a heterocycloalkyl group), a C1-8 alkyl group which may be substituted, a benzyl group in which a phenyl group may be substituted, or CH ₂ —OR ₃ ′ (R ₃ ′ may be substituted) R ₂ ′ represents a hydrogen atom, COR ₇ ′ (R ₇ ′ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group). ), SR ₈ ′ (R ₈ ′ represents an optionally substituted C1-8 alkyl group), substituted An optionally substituted C 1-8 alkyl group, an optionally substituted C 2-8 alkenyl group, a phenyl group optionally substituted benzyl group, or CH ₂ —OR ₃ (R ₃ is optionally substituted C 1 And X represents a nitrogen atom, provided that R ₁ ′ and R ₂ ′ do not represent a hydrogen atom or an acetyl group at the same time.

As a more preferred combination, R ₁ ′ is a hydrogen atom, COR ₄ ′ (R ₄ ′ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ ′. Or SNHR ₅ ′ (R ₅ ′ represents an optionally substituted C1-8 alkyl group, and optionally substituted phenyl group), R ₂ ′ represents a hydrogen atom, COR ₇ ′ (R ₇ ′ is optionally substituted by C1~8 alkyl group represents a or an optionally substituted phenyl group), or SR ₈ '(R _8' represents optionally substituted C1~8 alkyl group) And X is a nitrogen atom (provided that R ₁ ′ and R ₂ ′ do not represent a hydrogen atom or an acetyl group at the same time), or R ₁ ′ represents a hydrogen atom or a methyl group, and X represents a nitrogen atom in and, R ₂ 'is optionally substituted C1~8 alkyl, optionally substituted C2~8 alkenyl Or a group, a benzyl group which may phenyl group substituted, R ₂ 'is a hydrogen atom, X represents a nitrogen atom, R _1' is _{SR 5 ', SNHR 5' (} R 5 ' is substituted An optionally substituted C1-8 alkyl group, an optionally substituted phenyl group, or an optionally substituted 5- or 6-membered heterocycloalkyl group), or X is a nitrogen atom, R ₁ ′ and R ₂ ′ are the same and COR ₄ ′ (R ₄ ′ represents an optionally substituted C 1-8 alkyl group or an optionally substituted phenyl group), or CH ₂ —OR ₃ ′ (R ₃ ′ represents an optionally substituted C1-8 alkyl group).

As a preferred specific combination, when X is a nitrogen atom, R ₂ ′ is a hydrogen atom, R ₁ ′ is an acetyl group, 3-pyridylcarbonyl group, benzoyl group, 2,6-difluorobenzoyl group, 4-trifluoro Methoxybenzoyl group, 2,4,6-trimethylbenzoyl group, isopropylcarbonyl group, phenylthio group, n-hexylthio group, sec-butylthio group, cyclohexylthio group, 4,4,4-trifluorobutan-2-ylthio group, An isopropylthio group, a heptan-2-ylthio group, a heptane-4-ylthio group, and a tert-butylaminothio group can be mentioned, and a particularly preferred specific combination is when X is a nitrogen atom and R ₂ ′ is a hydrogen atom. R ₁ ′ is an acetyl group, a benzoyl group, an isopropylthio group, or a 4,4,4-trifluorobutan-2-ylthio group.

  Specific examples of the compounds represented by formula (I) or (I ′) are shown in Tables 1 to 4.

The compound represented by the formula (I) can be obtained by synthesis by the following method, or for some compounds as a commercial product.
The following formula (Ia),

Formula (Ia)
[Wherein R ₁ is
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
CH ₂ -O-R ₃ ,
CH ₂ -O-CO-R ₃
(In the above group, R ₃ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
COR ₄ ,
COOR ₄ ,
CONHR ₄ ,
COSR ₄ ,
(In the above group, R ₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ,
SOR ₅ ,
SOOR ₅ ,
SNHR ₅ ,
CSNHR ₅ ,
CSSR ₅ ,
(In the above group, R ₅ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6} ,
CH ₂ -O-R ₆ ,
(In the above group, R ₆ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ,
SOR ₈ ,
SOOR ₈ ,
SNHR ₈ ,
CSR ₈ ,
CSNHR ₈ ,
CSSR ₈ ,
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
NH ₂
NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CO−R ₉ ) ₂ ,
N− (COO−R ₉ ) ₂ ,
N− (COS−R ₉ ) ₂ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
NH-R ₁₀ ,
NH-S-R ₁₀
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH-R ₁₁
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH-NR ₁₂ R ₁₃
(In the above group, R ₁₂ and R ₁₃ are each independently a C1-8 alkyl group which may be substituted,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
O-R ₁₄
(In the above group, R ₁₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
X represents a nitrogen atom or CH].
Formula (IIa)

Formula (IIa)
[Wherein R ₂ and X are the same as defined in the above formula (Ia)], and can be synthesized using as a raw material.
In formula (Ia):
A C1-8 alkyl group in which R ₁ may be substituted;
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
CH ₂ -O-R ₃ ,
_{CH 2 -O-CO-R 3} ,
(In the above group, R ₃ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
The compound represented by the formula (Ia) is obtained by reacting the compound represented by the formula (IIa) and the reagent represented by the following formula (IIIa) or the following formula (IIIb) in the presence or absence of a base. Obtainable.

Formula (IIIa)

Formula (IIIb)
[In the above formulas (IIIa) and (IIIb), R ₁ and R ₃ have the same meaning as defined above, and Y represents a chlorine atom, a bromine atom or an iodine atom. ].
In the case of using a base, for example, potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like can be used, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa).
As the solvent used in the reaction, for example, ethyl acetate, chloroform, acetone, tetrahydrofuran, dichloromethane and the like are used, and preferably acetone. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 50 to 100 equivalents, relative to the compound represented by the formula (IIa). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.
In formula (Ia):
R ₁ is COR ₄ ,
COOR ₄ ,
CONHR ₄ ,
COSR ₄
(In the above group, R ₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
A compound represented by the formula (Ia), a compound represented by the formula (IIa), a compound represented by the following formula (IVa), and the following formula (IVa): It can be obtained by reacting the reagent represented by the formula (IVb) or the following formula (IVc) in the presence or absence of a base.

Formula (IVa)

Formula (IVb)

Formula (IVc)
[In the above formulas (IVa), (IVb) and (IVc), R ₄ has the same meaning as defined above, and Z represents an oxygen atom, a sulfur atom or NH. ].
When a base is used, examples of the base used include potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa).
As the solvent used in the reaction, for example, acetone, ethyl acetate, water, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, chloroform, or dichloromethane can be used, and preferably acetone or water. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (IIa). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.
In formula (Ia):
R ₁ is SR ₅ ,
SOR ₅ ,
SOOR ₅ ,
SNHR ₅ ,
CSNHR ₅ ,
CSSR ₅ ,
(In the above group, R ₅ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
(Representing an optionally substituted aromatic 5- or 6-membered heterocycle, optionally substituted 5- or 6-membered heterocycloalkyl group), the compound represented by the formula (Ia) is: By reacting a compound represented by the formula (IIa) with a reagent represented by the following formula (Va) prepared by, for example, a method represented by a new experimental chemistry course (14-III 1742-1746) in the presence of a base. Obtainable.

Formula (Va)
[In the above formula (Va), R ₅ has the same meaning as defined above, and Y represents a chlorine atom or a bromine atom. ]
As the base to be used, for example, potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like can be used, and triethylamine is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa).
As the solvent used in the reaction, for example, dimethylformamide, chloroform, acetone, tetrahydrofuran, dimethyl sulfoxide, dichloromethane and the like are used, and dimethylformamide is preferable. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 10 to 50 equivalents, relative to the compound represented by formula (IIa). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.

The compound represented by the formula (IIa) can be obtained as follows.In the formula (IIa),
When R ₂ represents a hydrogen atom, it can be obtained by the method described in J. Heterocyclic. Chem., 16, 199 (1979).

In formula (IIa)
A C1-8 alkyl group in which R ₂ may be substituted;
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
When it represents an optionally substituted aromatic 5- or 6-membered heterocyclic methyl group, a compound of formula (IIa) can be obtained according to the following scheme [formula (VIa), formula (VIb), R ₂ in formula (VIc) and formula (IIa) has the same meaning as defined above]. That is, the amine represented by formula (VIa) is reacted with a halogenated aryl carbonate compound in the presence or absence of a base to form formula (VIb), then reacted with hydrazine to formula (VIc), and further an acid catalyst. It can be obtained by reacting with formic acid or orthoformate in the presence or absence.

When a base is used in the reaction from formula (VIa) to formula (VIb), for example, potassium carbonate, sodium hydroxide, sodium hydride, butyllithium, triethylamine, pyridine and the like can be used, and pyridine is preferred. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (VIa).
As the solvent used in the reaction, for example, dichloromethane, ethyl acetate, chloroform, acetone, tetrahydrofuran and the like are used, and preferably dichloromethane. The solvent to be used can use 1-1000 equivalent with respect to the compound shown by Formula (VIa), Preferably it is 2-50 equivalent.
The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.
As the solvent used in the reaction from formula (VIb) to formula (VIc), for example, ethanol, methanol, dichloromethane, chloroform, acetone, tetrahydrofuran and the like are used, and preferably ethanol. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (VIb). The reaction can be carried out at −78 to 200 ° C., preferably 80 to 100 ° C.
In the reaction from formula (VIc) to formula (IIa), when an acid is used, as the acid to be used, for example, paratoluenesulfonic acid, hydrochloric acid, sulfuric acid, formic acid, aluminum chloride, etc. can be used, preferably Paratoluenesulfonic acid, hydrochloric acid, and formic acid. The acid to be used can be used in an amount of 0.0001 to 50 equivalents, preferably 0.01 to 5 equivalents, relative to the compound represented by the formula (VIc). As the solvent used in the reaction, for example, ethanol, methanol, dichloromethane, chloroform, acetone, tetrahydrofuran and the like are used, and ethanol is preferable. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (VIc).
The formic acid or orthoformate to be used can be used in an amount of 1 to 1000 equivalents, preferably 3 to 20 equivalents, relative to the compound represented by the formula (VIc). The reaction can be carried out at 0 to 250 ° C, preferably 110 to 160 ° C.

In formula (IIa):
R ₂ is CH ₂ -O-CO-R ₆ ,
CH ₂ -O-R ₆
(In the above group, R ₆ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
The compound represented by the formula (IIa) is obtained by reacting the reagent represented by the formula (VIIa) or the formula (VIIb) with the compound represented by the formula (IIa ′) in the presence or absence of a base. Can do.

Formula (VIIa)

Formula (VIIb)

Formula (IIa ')
[In the above formulas (VIIa) and (VIIb), R ₆ has the same meaning as defined above, Y represents a chlorine atom, bromine or iodine atom. In the formula (IIa ′), X represents a nitrogen atom or CH. Show. ]
In the case of using a base, for example, potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like can be used, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa ′).
As the solvent used in the reaction, for example, ethyl acetate, chloroform, acetone, tetrahydrofuran, dichloromethane and the like are used, and preferably acetone. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 50 to 100 equivalents, relative to the compound represented by the formula (IIa ′). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.
In formula (IIa)
R ₂ is COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇ ,
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
The compound represented by the formula (IIa) is represented by the following formula (VIIIa), the following formula (VIIIb) or the following formula (VIIIc): And the compound represented by the above formula (IIa ′) in the presence or absence of a base.

Formula (VIIIa)

Formula (VIIIb)

Formula (VIIIc)
[In the above formula (VIIIa), formula (VIIIb) and formula (VIIIc), R ₇ has the same meaning as defined above, and Z represents an oxygen atom, a sulfur atom or NH]
When a base is used, examples of the base used include potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa ′).
Examples of the solvent used in the reaction include acetone, ethyl acetate, water, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, chloroform, dichloromethane, preferably dimethylformamide, acetone, or water. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (IIa ′).
The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.

In formula (IIa):
R ₂ is SR ₈ ,
SOR ₈ ,
SOOR ₈ ,
SNHR ₈ ,
CSR ₈ ,
CSNHR ₈ ,
CSSR ₈
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
The compound represented by the formula (IIa) is represented by the following formula (IXa), the following formula (IXb), the following formula (IXc): It can be obtained by reacting a reagent represented by the following formula (IXd) or (IXe) with a compound represented by the above formula (IIa ′) in the presence or absence of a base.

Formula (IXa)

Formula (IXb)

Formula (IXc)

Formula (IXd)

Formula (IXe)
[In the above formula (IXa), formula (IXb), formula (IXc), formula (IXd), formula (IXe), R ₈ has the same meaning as defined above, and W represents a sulfur atom or NH. ]
When a base is used, examples of the base used include potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa ′).
Examples of the solvent used in the reaction include acetone, ethyl acetate, water, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, chloroform, dichloromethane, preferably dimethylformamide, acetone, or water. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (IIa ′). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.

In formula (IIa):
A compound in which R ₂ is NH ₂ (formula (XIa)) can be obtained by Chem. Ber., 98, 3025 (1965).

In formula (IIa):
R ₂ is NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CO−R ₉ ) ₂ ,
N− (COO−R ₉ ) ₂ ,
N− (COS−R ₉ ) ₂ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
The compound represented by the formula (IIa) is represented by the following formula (Xa), the following formula (Xb) or the following formula (Xc): And the following formula (XIa) can be obtained in the presence or absence of a base.

Formula (Xa)

Formula (Xb)

Formula (Xc)

Formula (XIa)
[In the above formula (Xa), formula (Xb), and formula (Xc), R ₉ has the same meaning as defined above, V represents an oxygen atom or a sulfur atom, and X represents a nitrogen atom or CH. ]
When a base is used, examples of the base used include potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (XIa). Examples of the solvent used in the reaction include acetone, ethyl acetate, water, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, chloroform, dichloromethane, preferably dimethylformamide, acetone, or water. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (XIa). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.

In formula (IIa):
R ₂ is NH-R ₁₀ ,
NH-S-R ₁₀
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
A compound represented by the formula (IIa) is represented by the following formula (XIIa) or the following formula (XIIb): It can be obtained by reacting the above formula (XIa) in the presence of a base.

Formula (XIIa)

Formula (XIIb)
[In the formulas (XIIa) and (XIIb), R ₁₀ has the same meaning as defined above, and Y represents a chlorine atom, a bromine atom or an iodine atom. ]
As the base to be used, for example, potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like can be used, and triethylamine is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (XIa). As the solvent used in the reaction, for example, dimethylformamide, chloroform, acetone, tetrahydrofuran, dimethyl sulfoxide, dichloromethane and the like are used, and dimethylformamide is preferable.
The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 10 to 50 equivalents, relative to the compound represented by the formula (XIa). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.

In formula (IIa):
R ₂ is N = CH−R ₁₁
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group)
Can be obtained according to the following scheme.

[In the formulas (XIIIa) and (XIIIb), R _11a and R _11b have the same definition as R ₁₁ above, except that the sum of the carbon numbers of R _11a and R _11b is 0-7, and X is a nitrogen atom. Or CH. ]
That is, the substance represented by the formula (XIIIa) is obtained by reacting the compound represented by the formula (XIa) with the carbonyl compound represented by R _11a —CO—R _11b in the presence of an acid catalyst.
The compound represented by the formula (XIIIb) can also be obtained by reducing the compound represented by the formula (XIIIa) with a common reducing agent such as sodium borohydride, sodium cyanoborohydride and the like.
In the reaction from formula (XIa) to formula (XIIIa), for example, paratoluenesulfonic acid, camphorsulfonic acid, hydrochloric acid, sulfuric acid, acetic acid and the like can be used, and camphorsulfonic acid is preferable. The acid to be used can be used in an amount of 0.0001 to 10 equivalents, preferably 0.005 to 0.05 equivalents, relative to the compound represented by the formula (XIa). Examples of the solvent used for the reaction include dimethylformamide, chloroform, ethanol, methanol, tetrahydrofuran, dimethyl sulfoxide, dichloromethane, and the like, and preferably ethanol.
The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 5 to 50 equivalents, relative to the compound represented by the formula (XIa). The reaction can be carried out at −78 to 250 ° C., preferably 80 to 120 ° C.
As the reducing agent used in the reaction from the formula (XIIIa) to the formula (XIIIb), for example, lithium aluminum hydride, sodium borohydride, sodium cyanoborohydride and the like can be used, preferably sodium borohydride, hydrogen Sodium cyanoborohydride. The reducing agent to be used can be used in an amount of 0.1 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to the compound represented by the formula (XIIIa). As the solvent used for the reaction, for example, chloroform, ethanol, methanol, tetrahydrofuran, dichloromethane and the like are used, and preferably ethanol.
The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 5 to 50 equivalents, relative to the compound represented by the formula (XIIIa). The reaction can be carried out at -78 to 250 ° C, preferably 0 to 30 ° C.

In formula (IIa):
R ₂ is
N = CH-NR ₁₂ R ₁₃
(R ₁₂ and R ₁₃ are each independently
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
The compound represented by the formula (IIa) is a compound represented by the above formula (XIa), and the following formula (XIVa):
It can be obtained by reacting the reagent represented by the above in the presence of an acid catalyst.

Formula (XIVa)
[In the formula (XIVa), R ₁₂ and R ₁₃ have the same definitions as above].
As the acid to be used, for example, p-toluenesulfonic acid, camphorsulfonic acid, hydrochloric acid, sulfuric acid, acetic acid and the like can be used, and camphorsulfonic acid is preferable. The acid to be used can be used in an amount of 0.0001 to 10 equivalents, preferably 0.005 to 0.05 equivalents, relative to the compound represented by the formula (XIa). Examples of the solvent used for the reaction include chloroform, ethanol, methanol, tetrahydrofuran, dimethyl sulfoxide, dichloromethane, and the like, and preferably ethanol. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 5 to 50 equivalents, relative to the compound represented by the formula (XIa). The reaction can be carried out at −78 to 250 ° C., preferably 80 to 120 ° C.

In formula (IIa):
R ₂ is O−R ₁₄
(R ₁₄ may be substituted C1~8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
Or
R ₂ is NH-R ₁₀
(R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group, and when X represents a nitrogen atom, the compound of formula (IIa) can be obtained according to the following scheme.

[In the above scheme, R ₁₀ and R ₁₄ have the same meaning as defined above, and U represents an oxygen atom or a nitrogen atom]
That is, the substance represented by the formula (XVd) is reacted with a halogenated aryl carbonate compound in the presence or absence of a base to form a formula (XVb) and then reacted with hydrazine. And is obtained by further reacting with formic acid or orthoformate in the presence or absence of an acid catalyst.
When a base is used in the reaction from formula (XVa) to formula (XVb), for example, potassium carbonate, sodium hydroxide, sodium hydride, butyllithium, triethylamine, pyridine and the like can be used, and pyridine is preferred. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (XVa). As the solvent used in the reaction, for example, dichloromethane, ethyl acetate, chloroform, acetone, tetrahydrofuran and the like are used, and preferably dichloromethane. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (XVa). The reaction can be carried out at −78 to 200 ° C., preferably 10 to 30 ° C.
As the solvent used for the reaction from formula (XVb) to formula (XVc), for example, ethanol, methanol, dichloromethane, chloroform, acetone, tetrahydrofuran and the like are used, and preferably ethanol. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (XVb). The reaction can be carried out at −78 to 200 ° C., preferably 80 to 100 ° C.
When an acid is used in the reaction from formula (XVc) to formula (XVd), as the acid used, for example, paratoluenesulfonic acid, hydrochloric acid, sulfuric acid, formic acid, aluminum chloride and the like can be used, preferably paratoluene. Sulfonic acid, hydrochloric acid or formic acid. The acid to be used can be used in an amount of 0.0001 to 50 equivalents, preferably 0.01 to 5 equivalents, relative to the compound represented by the formula (XVc). As the solvent used in the reaction, for example, ethanol, methanol, dichloromethane, chloroform, acetone, tetrahydrofuran and the like are used, and ethanol is preferable. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (XVc).
The formic acid or orthoformate used can be used in an amount of 1 to 1000 equivalents, preferably 3 to 20 equivalents, relative to the compound represented by the formula (XVc). The reaction can be carried out at 0 to 250 ° C, preferably 110 to 160 ° C.

  The following formula (Ib)

Formula (Ib)
[Where R _1b = R _2b and R _1b and R _2b are
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6b} ,
CH ₂ -O-R _6b ,
(In the above group, R _6b is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
X represents a nitrogen atom or CH],
It can also be obtained by reacting the reagent represented by the following formula (XVIa) with the compound represented by the formula (IIa ′) in the presence or absence of a base.

Formula (XVIa)
[In the above formula (XVIa), R _1b represents the same meaning as defined above, and Y represents a chlorine atom, a bromine atom or an iodine atom. ]
When a base is used, examples of the base used include potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (IIa ′).
Examples of the solvent used for the reaction include acetone, ethyl acetate, water, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, chloroform, and dichloromethane, and preferably acetone or water. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (IIa ′). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.
The following formula (Ic)

Formula (Ic)
[R _1c is CO-R ₄ ,
COO-R ₄ ,
COS-R ₄ ,
CSS-R ₄ ,
R _2c is NH-CO-R _9c ,
NH-COO-R _9c ,
NH-COS-R _9c
NH-CSS-R _9c ,
N- (CO-R _9c ) ₂
N- (COO-R _9c ) ₂
N− (COS−R _9c ) ₂
N- (CSS-R _9c ) ₂ is shown. Here, R ₄ = R _9c , the definition of R _{4 is} the same as defined in the above formula (I), and X represents a nitrogen atom or CH], the compound represented by the above formula (IVa), It can be obtained by reacting (IVb) or the reagent represented by the formula (IVc) with the formula (XIa) in the presence or absence of a base.
When a base is used, examples of the base used include potassium carbonate, sodium hydroxide, sodium hydride, butyl lithium, triethylamine, pyridine and the like, and potassium carbonate is preferable. The base to be used can be used in an amount of 0.1 to 50 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (XIa).
Examples of the solvent used in the reaction include acetone, ethyl acetate, water, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, chloroform, dichloromethane, preferably dimethylformamide, acetone, or water. The solvent to be used can be used in an amount of 1 to 1000 equivalents, preferably 2 to 50 equivalents, relative to the compound represented by the formula (XIa). The reaction can be carried out at -78 to 200 ° C, preferably 0 to 30 ° C.
The compound obtained as described above can be purified by, for example, chromatography using silica gel to obtain the target product as a pure product.

  The compound represented by the formula (I ′) can also be obtained in the same manner as the compound represented by the formula (I).

    The insect species showing the control effect of the pest control agent containing at least one compound of the present invention represented by the formula (I) is not particularly limited, but as an agricultural and horticultural pest, lepidoptera Pests (for example, Spodoptera litura, Coleoptera, Acalycium, Aomushi, Konaiga, Shirochimojitoto, Nikameiga, Knotomoiga, Scutella, Sigaiiga, Amoguriga, Dokuga, Agrotis spp, Helicoberpa spp (Helicoverpa sp) ), Etc.), Hemiptera aphids, cotton aphids, Aphisfabae, corn aphids, pea aphids, potato aphids, bean aphids, tulip aphids, Macrosiphum avenae, Metropolophium dirhodum, wheat beetles Aphididae (Aphididae, Adelgidae, Phy11oxeridae), Aphidoxaeidae, Phy11oxeridae, Azalea, Aphididae, Chanomidoriyoyoe Japanese planthoppers such as Japanese brown planthopper, Japanese planthopper, white-tailed planthopper, white-tailed beetle, southern stink bug, stink bug such as red-bellied beetle, silverleaf whitefly, tobacco whitefly, white-footed whitefly, white-eyeworm Scale insects (Diaspididae, Margarodidae, Ortheziidae, Ac1erdiae, Dacty1opiidae, Kerridae, Pseu, etc.) dococcidae, Coccidae, Eriococcidae, Asterolecaniidae, Beesonidae, Lecanodiaspididae, Cerococcidae, etc. Colorado potato beetle, rice beetle, beetle, longhorn beetle, etc., mites (for example, urticae, kanzawa spider mite, citrus mite), hymenopterous insects (for example, wasps), straight worms (for example, grasshoppers), diptera Eye pests (eg, house flies, leafhoppers), thrips pests (eg, southern thrips, citrus thrips, etc.), plant parasitic nematodes (eg, root-knot nematodes, nectar nematodes) And parasites of animals include ticks (eg, Lone star ticks, Gulf ticks, Rocky ticks, West Coast ticks, West Coast ticks, American dog ticks, Crimson ticks) Mites, mites, mites, manes, mites, western mites, western mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites, mites ), Mite mites (for example, bovine mushroom mite mites), mites mites (for example, mushroom mites mite, mite mites mites), mite mites (for example, birds) Ticks), worms, spider mites (e.g., chicken spider mites, stag beetles), tsutsugamushi (e.g. Miyamatsu tsutsugamushi, akatsutsumushi), fleas (e.g., cat fleas, human fleas), lice (e.g. , Chicken lice), lice (eg, pig lice, dog lice, leaf lice, human lice, white lice), flies (eg, bull flies, horn flies), aphids, mosquitoes (eg, Aedes albopictus, Acacia, etc.), flyfish, nukaka , Nematodes (eg, fecal nematodes, helminths, roundworms (eg, tortuous stomachs, murine roundworms), ciliate nematodes, rotifers (eg, swine lungworms, Guangdong dwellers) Hemlockworms, cat lungworms), helminths, caecal worms (eg, chicken roundworm), roundworms (eg, Anisakis nematode, pig roundworm, horse roundworm, dog roundworm, cat roundworm) , Gyrus nematodes (e.g., bursula, spiny-mouthed jawworms, cat stomachworms, horoscope stomachworms, largemouth horse stomachworms, chicken stomachworms), filamentous worms (e.g. , Nematodes, trichinella (e.g., Trichinella, Trichinella), flukes (e.g., Schistosoma japonicum, liver fluke), bald worms, tapeworms (e.g., suspicious leaves (e.g., Manson saccharides), circles (for example, Coleoptera), and protozoa. More preferably, lepidopterous insects, hemiptera pests, thrips pests, diptera pests, Coleoptera pests, animal parasitic fleas, mites, and more preferably hemiptera pests, thrips Pests and animal parasitic mites.

The pest control agent of the present invention can be prepared using a carrier corresponding to the method of use in addition to the compound represented by the formula (I).
Examples of the carrier that can be used include a liquid carrier, a solid carrier, a gaseous carrier, a surfactant, a dispersant, and other adjuvants for preparation.

  Examples of the solid carrier include clays (carion clay, diatomaceous earth, bentonite, acid clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (selinite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.) ) And other fine powders and granules, starch, lactose, vinyl chloride polymers, polyurethane and other synthetic polymers.

  Examples of the liquid carrier include alcohols (methanol, ethanol, isopropanol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, glycerin, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzyl). Alcohol, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (paraffin, n-hexane, cyclohexane, kerosene, kerosene, etc.), ethers (diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diisopropyl ether, Diethyl ether, dioxane, tetrahydrofuran, etc.), esters (propylene carbonate, ethyl acetate, butyl acetate, benzyl benzoate, misses) Isopropyl titanate, propylene glycol fatty acid ester, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), amides (dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, Carbon tetrachloride, etc.), animal and vegetable oils such as soybean oil, cotton seed drops, dimethyl sulfoxide, silicone oil, higher fatty acids, glycerol formal, water and the like.

  Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin A sulfonate or the like is used.
Furthermore, as an adjuvant for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like are used.
The above carriers, surfactants, dispersants, and adjuvants may be used alone or in combination as necessary.

  When the pest control agent of the present invention is an agricultural pest control agent, it is usually mixed with an appropriate solid carrier, liquid carrier, gaseous carrier, surfactant, dispersing agent or other formulation auxiliary agent to prepare an emulsion or liquid. , Suspensions, wettable powders, flowables, powders, granules, tablets, oils, aerosols, smokes and the like.

    Examples of the solid carrier include talc, bennite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.

  Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene. Aromatic hydrocarbons such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil Vegetable oils such as cottonseed oil, dimethyl sulfoxide, water and the like.

  Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

  Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, Lignin sulfonate and the like are used.

  Moreover, as an adjuvant for improving the property of a formulation, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate etc. are used, for example.

  The above carriers, surfactants, dispersants, and adjuvants may be used alone or in combination as necessary.

  The content of the active ingredient in the preparation is not particularly limited, but is usually 1-75% by weight for emulsions, 0.3-25% by weight for powders, 1-90% by weight for wettable powders, and 0 for granules. .5-10% by weight.

The compound represented by the formula (I) and these preparations may be used as they are, but in some cases, they are preferably diluted into seeds, plant foliage parts, root parts, soil, water surfaces, and cultivation materials. Can be applied to seeds, roots, soil, water surface, cultivation materials.
The pest control agent containing at least one compound represented by the formula (I) is a plant, crop (for example, herbicide-tolerant crop, insect pest resistance gene incorporating an insecticidal protein production gene) created by breeding techniques or gene transfer. It can also be applied to the introduction of crops, disease-tolerant crops incorporating disease-inducing substance production genes, disease-enhancing crops, shelf-stable crops, yield-enhancing crops, etc.).

  When the pest control agent of the present invention is an animal parasitic pest control agent, it is a liquid, emulsion, liquefied drop, spray, foam preparation, tablet, granule, fine granule, powder, capsule, tablet, Provided as chewable agents, injection agents, suppositories, cream agents, shampoo agents, rinse agents, resin agents, smoke agents, poison baits, etc., liquid agents and liquefied drops are particularly preferred.

  The liquid preparation can further contain formulation emulsifiers such as ordinary emulsifiers, dispersants, spreading agents, wetting agents, suspending agents, preservatives, propellants, etc. A forming agent can also be blended. Examples of surfactants for emulsification, dispersion, spreading, etc. include soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl allyl ethers, polyoxyethylene fatty acid esters, higher alcohols, alkylaryls A sulfonate or the like is used. Examples of the dispersant include casein, gelatin, polysaccharides, lignin derivatives, saccharides, and synthetic water-soluble polymers. Examples of spreading / wetting agents include glycerin and polyethylene glycol. Examples of the suspending agent include casein, gelatin, hydroxypropyl cellulose, gum arabic and the like. Examples of the stabilizing agent include phenolic antioxidants (BHT, BHA, etc.) and amine antioxidants (diphenylamine, etc.). ), Organic sulfur-based antioxidants and the like. Examples of the preservative include methyl paraoxybenzoate, ethyl paraoxybenzoate, propyl paraoxybenzoate, and butyl paraoxybenzoate. The above carriers, surfactants, dispersants, and adjuvants may be used alone or in combination as necessary. Furthermore, you may contain a fragrance | flavor, a synergist, etc. The content of the active ingredient in the pest control agent of the present invention is usually 1 to 75% by weight in the liquid form.

  Examples of the carrier used for preparing the cream include non-volatile hydrocarbons (such as liquid paraffin), lanolin-added oils and fats, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils, and water. , Emulsifiers, moisturizers, antioxidants, fragrances, borax, and ultraviolet absorbers may be used alone or in combination as required. Examples of the emulsifier include fatty acid sorbitan, polyoxyethylene alkyl ether, and fatty acid polyoxyethylene. The content of the active ingredient in the pest control agent of the present invention is usually 0.5 to 70% by weight for creams.

  For capsules, pills or tablets, the active ingredient in the composition of the present invention is appropriately subdivided and mixed with a diluent or a carrier such as starch, lactose or talc, and further a disintegrant such as magnesium stearate. And / or it can be used by adding a binder and tableting as necessary.

  Carriers for preparing injections must be prepared as sterile solutions, which contain other substances, for example enough salt or glucose to make the solution isotonic with blood. May be. Carriers that can be used include glycerides, benzyl benzoate, isopropyl myristate and esters such as fatty acid derivatives of propylene glycol, organic solvents such as N-methylpyrrolidone, glycerol formal. The content of the active ingredient in the pest control agent of the present invention is suitably 0.01 to 10% by weight for injections.

  Examples of the carrier for preparing the resin agent include vinyl chloride polymers and polyurethane. If necessary, plasticizers such as phthalates, adipic esters, and stearic acid can be added to these substrates. The active ingredient is kneaded in the base material and then molded by injection molding, extrusion molding, press molding or the like. Furthermore, it can be made into an animal ear tag and an animal insect repellent collar through processes such as proper molding and cutting.

Carriers for poisonous baits include food and attractants (flours such as wheat flour and corn flour, starches such as corn starch and potato starch, sugars such as granulated sugar, maltose and honey, foods such as glycerin, onion flavor and milk flavor) Examples thereof include animal powders such as flavors, rice bran powder, fish meal, various pheromones, etc. The content of the active ingredient of the pest control agent of the present invention is usually 0.0001-90% by weight for poison baits.
The pest control agent of the present invention is administered orally or by injection into the body of an applied animal, administered to the whole or a part of the body surface of the applied animal, and covers places where pest invasion, parasitism, and migration are expected. By doing so, pests can be controlled.

  The pest control agent of the present invention may be used as it is, but depending on the case, it can be diluted with water, liquid carrier, commercially available shampoo, rinse, bait, breeding house underlay or the like.

In addition, the pest control agent according to the present invention can be used by mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like. Drugs that can be used in combination include those described in the Pesticide Manual (published by The British Crop Protection Council 13th edition) and Shibuya Index (published by SHIBUYA INDEX 13th edition, 2008, published by SHIBUYA INDEX RESEARCH GROUP). It is done. More specifically, insecticides, acaricides or nematicides include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenfos ), Pyraclofos, chlorpyrifos-methyl, organophosphate compounds such as diazinon, mesomyl, thiodicarb, aldicarb, oxamyl, propoxyl (Propoxur), carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran, carbamate compounds such as benfuracarb, cartap, thiocyclam (t neolystoxin derivatives such as hiocyclam, organochlorine compounds such as dicofol, tetradifon, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin ( cyhalothrin), fenvalerate, fluvalinate, etofenprox, pyrethroid compounds like silafluofen, diflubenzuron, teflubenzuron, flufenoxuron, flufenoxuron, Benzoylurea compounds such as chlorfluazuron, juvenile hormone-like compounds such as metoprene, molting hormone-like compounds such as chromafenozide, and other compounds such as buprofezin, hexitiazox ( he xythiazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, pyrimidifen, tebufenpyrad, tolfenpyrad, fluacryofyl, fluacpy ), Fulbendizmide, ethiprole, fipronil, etoxazole, imidacloprid, clothianidin, thiamethoxam, thiamethoxam, acetamiprid, aceramiprid thiacloprid, dinotefuran, pymetrozine, bifenazate, spirodiclofen, Piromesifen, flonicamid, chlorfenapyr, pyriproxyfene, indoxacarb, pyridalyl, or spinosad, avermectin, milbemycin, milbemycin Cyenopyrafen, spinetoram, pyrifluquinazon, chlorantraniliprole, cyantraniliprole, spirotetramat, lepimectin, metaflumizone, metaflumizone Luprolol, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flometoquin, organometallic Compounds, dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, compounds such as hydrazine compounds.
Furthermore, the composition according to the present invention can be mixed or used in combination with microbial pesticides such as BT agents, entomopathogenic virus agents and the like.
Bactericides used in combination or in combination include, for example, azoxystrobin, kresoxym-methyl, strobilurin-based compounds such as trifloxystrobin, mepanipyrim, pyrimethanil, Anilinopyrimidine compounds such as cyprodinil, triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole ), Microbutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, quinomethionate, and quinomethionate. Xanthines, maneb, zineb, mancozeb, polycarbamate, dithiocarbamate compounds such as propineb, phenyl carbamate compounds such as dietofencarb, chlorothalonil (chlorothalonil), organochlorine compounds such as quintozene, benomyl, thiophanate-methyl, benzimidazole compounds such as carbendazole, metalaxyl, oxadixyl, Phenylamide compounds such as ofurase, benalaxyl, furalaxyl, cyprofuram, sulfenic compounds such as dichlofluanid, copper hydroxide Copper-based, such as oxine-copper Compounds, isoxazole compounds such as hydroxyisoxazole, organic phosphorus compounds such as fosetyl-aluminium, tolclofos-methyl, captan, captafol, N-halogenothioalkyl compounds such as folpet, procymidone, iprodione, dicarboximide compounds such as vinchlozolin, flutolanil, mepronil Benzanilide compounds, morpholine compounds such as fenpropimorph, dimethomorph, phenthin hydroxide, organotin compounds such as fenthin acetate, Fludioxonil, fenpiclonil Cyanopyrrole compounds such as, fthalide, fluazinam, cymoxanil, triforine, pyrifenox, fenarimol, fenpropidin, penciclone ( pencycuron, cyazofamid, iprovalicarb, or benchthiavalicarb-isopropyl.

EXAMPLES Next, the present invention will be specifically described with reference to examples, but it goes without saying that the present invention is not limited by these examples.
The compound numbers described below are the same as the compound numbers described in Tables 1 to 4, and indicate the structures described in Tables 1 to 4.

Synthesis example
Synthesis Example 1: Synthesis of Compound 21 (Synthesis Method A)
Compound 1 (10.6 g) and potassium carbonate (17.3 g) obtained by the method described in Khimiya Geterotsiklicheskikh Soedinenii, 2 (1), 110 (1966) were dissolved in water (100 mL). Under vigorous stirring, benzoyl chloride (17.5 g) was added dropwise and reacted at room temperature for 20 minutes. The precipitated crystals were collected by filtration to obtain 3.9 g of the title compound.

Synthesis Example 2: Synthesis of Compound 14 (Synthesis Method C)
Benzylamine (3.22 g) was dissolved in pyridine (4.74 g) and dichloromethane (30 mL), and phenyl chlorocarbonate (4.7 g) was added at 0 ° C. After reacting at room temperature for 3 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 0.5N aqueous hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and then under reduced pressure. The solvent was distilled off to obtain 6.9 g of a phenylphenyl carbamate crude product.
Phenylbenzyl carbamate crude product (3.4 g) was dissolved in ethanol (20 mL), hydrazine monohydrate (863 mg) was added, and the mixture was refluxed for 9 hours. After cooling to room temperature, 20 mL of 0.8N aqueous hydrochloric acid was added, and ethanol was distilled off under reduced pressure. After washing with ethyl acetate, the aqueous layer was made alkaline by adding a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.4 g of a crude N-benzylhydrazinecarboxamide product.
N-benzylhydrazinecarboxamide crude product (2.0 g), triethyl orthoformate (5.37 g) and paratoluenesulfonic acid (6.24 g) were dissolved in ethanol (43 mL) and refluxed for 5 days. After adding 30 mL of saturated aqueous sodium hydrogen carbonate solution to the reaction solution, ethanol was distilled off and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel 60 (45 g), elution solvent; hexane: acetone 5: 4) to obtain 380 mg of the title compound. )

Synthesis Example 3: Synthesis of Compound 38 (Synthesis Method E)
Thionyl chloride (677 mg) was added to diisopropyl disulfide (750 mg) at −18 ° C. and reacted at this temperature for 1 hour to obtain a crude isopropylsulfene chloride product.
Compound 1 (170 mg) and triethylamine (444 mg) were dissolved in dimethylformamide (3 mL), and 245 mg of the prepared crude isopropylsulfene chloride was added at 0 ° C. and reacted at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. This was purified by preparative HPLC (column: capcellpak C18-AQ, mobile phase: acetonitrile-water) to obtain 3 mg of the title compound.

Synthesis Example 4: Synthesis of Compound 19 (Synthesis Method D)
Compound 14 (40 mg) synthesized in Synthesis Example 2 was dissolved in dichloromethane (3 mL), and potassium carbonate 128 mg and 2-bromoacetonitrile 110 mg were added and reacted at room temperature for 24 hours. The reaction solution was poured into water, extracted with ethyl acetate, the ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. This was purified by preparative HPLC (column: capcellpak C18-AQ, moving bed: acetonitrile-water) to obtain 8 mg of the title compound.

Synthesis Example 5 Synthesis of Compound 56 Carbohydrazine (4.5 g) was suspended in N-methyl-2-pyrrolidone (10 mL) and triethyl orthoformate (8.15 g) and heated at 140 ° C. for 6 hours. Reacted. After allowing to cool to room temperature, the precipitated crystals were collected by filtration to give 1.96 g of the title compound.

Synthesis Example 6: Synthesis of Compound 89 (Synthesis Method F)
Compound 56 (200 mg) and camphorsulfonic acid (23 mg) synthesized in Synthesis Example 5 were dissolved in 30 mL of ethanol, and benzaldehyde (255 mg) was added. Reflux for 3 hours, pour a portion (3 mL) into water, extract with ethyl acetate, wash the ethyl acetate layer with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dry over anhydrous sodium sulfate. Distillation gave 37 mg of the title compound.

Synthesis Example 7 Synthesis of Compound 90 (Synthesis Method F)
Compound 56 (200 mg) and camphorsulfonic acid (23 mg) synthesized in Synthesis Example 5 were dissolved in 30 mL of ethanol, and benzaldehyde (255 mg) was added. After refluxing for 3 hours and allowing to cool to room temperature, 91 mg of sodium borohydride was added at 0 ° C. The mixture was reacted at room temperature for 2 hours, and 2N-hydrochloric acid (2.5 mL) was added. Furthermore, 7.5 mL of water was added, ethanol was distilled off, 10 mL of chloroform was added, and the mixture was stirred at 50 ° C. After cooling, the mixture was separated into a chloroform layer and an aqueous layer. The aqueous layer was neutralized with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The ethyl acetate layer and the previous chloroform layer were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. This was purified by preparative TLC (developing solvent: hexane: acetone 1: 1) to obtain 58 mg of the title compound.

Synthesis Example 8: Synthesis of Compound 101 (Synthesis Method G)
Phenylhydrazine (2.7 g) and pyridine (3.96 g) were dissolved in dichloromethane (30 mL), phenyl chlorocarbonate (3.91 g) was added at 0 ° C., and the mixture was reacted at room temperature for 2.5 hours. The reaction solution was washed with 0.7N-hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, evaporated under reduced pressure, and purified by column chromatography (silica gel 60: 500 mL developing solvent; hexane: acetone) did. Further, this was recrystallized from 1.48 g of phenyl-2-phenylhydrazinecarboxylate.
Phenyl-2-phenylhydrazinecarboxylate (1.47 g) was dissolved in 10 mL of ethanol, hydrazine monohydrate (370 mg) was added, and the mixture was refluxed for 6 hours. After allowing to cool, ethanol was distilled off under reduced pressure, and the pH was adjusted to 3-4 with hydrochloric acid, followed by extraction with ethyl acetate. The aqueous layer was concentrated under reduced pressure to obtain a crude product of phenylsemicarbazone hydrochloride (1.3 g).
Phenyl semicarbazone hydrochloride (203 mg) and triethyl orthoformate (163 mg) were dissolved in N-methyl-2-pyrrolidone (1 mL) and reacted for 7 hours under heating at 140 ° C. This was purified by preparative HPLC (column: capcellpak C18 AQ, mobile phase: acetonitrile-water) to obtain 28 mg of the title compound.

Synthesis Example 9 Synthesis of Compound 30 (Synthesis Method B)
Compound 1 (170 mg) and potassium carbonate (152 mg) were dissolved in water (1.5 mL). Under vigorous stirring, ethyl chlorocarbonate (208 mg) was added dropwise and reacted at room temperature for 20 minutes. The precipitated crystals were collected by filtration to give 63 mg of the title compound.
The spectral data of the compounds described in Synthesis Examples 1 to 9 and the spectral data of the compounds obtained in the same manner as described above are shown in Tables 5 to 9.

Formulation example

Formulation Example 1 [Granule]
Compound 3 5% by weight
Bentonite 40% by weight
Talc 10% by weight
43% by weight of clay
2% by weight calcium lignin sulfonate
The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.

Formulation Example 2 [wettable powder]
Compound 21 30% by weight
50% by weight of clay
2% white carbon
Diatomaceous earth 13% by weight
Calcium lignin sulfonate 4% by weight
Sodium lauryl sulfate 1% by weight
The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.

Formulation Example 3 [Granule wettable powder]
Compound 38 30% by weight
60% clay
Dextrin 5% by weight
Alkyl maleic acid copolymer 4% by weight
Sodium lauryl sulfate 1% by weight
The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.

Formulation Example 4 [Flowable Agent]
Compound 51 25% by weight
POE polystyryl phenyl ether sulfate 5% by weight
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
PRONAL EX-300 (Toho Chemical Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
100% by weight of water
The total amount excluding the 1% aqueous solution of xanthan gum and an appropriate amount of water from the above blend was premixed and then pulverized with a wet pulverizer. Thereafter, 1% aqueous solution of xanthan gum and the remaining water were added to obtain a flowable agent at 100% by weight.

Formulation Example 5 [Emulsion]
Compound 4 15% by weight
N, N-dimethylformamide 20% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight
10% by weight of polyoxyethylene alkyl aryl ether
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 6 [powder]
Compound 3 2% by weight
60% clay
Talc 37% by weight
Calcium stearate 1% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 7 [DL powder]
Compound 38 2% by weight
DL clay 94.5% by weight
2% white carbon
Calcium stearate 1% by weight
Light liquid paraffin 0.5% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 8 [Fine Granule F]
Compound 38 2% by weight
Carrier 94% by weight
2% white carbon
Hyzol SAS-296 2% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 9 (Liquid drops)
Compound 37 10% by weight
Benzyl alcohol 74.9% by weight
15% by weight propylene carbonate
Dibutylhydroxytoluene 0.1% by weight
The above components were uniformly stirred and dissolved to obtain a liquefied droplet.

Test example

Test Example 1 Green-bellied planthopper control test The seedling root of wheat 48 hours after sowing was treated with a chemical solution prepared to a predetermined concentration with 10% acetone water. After 72 hours of absorption of the drug from the root, 10 second-instar larvae were released. Thereafter, it was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 7 days after the release, and the mortality was calculated according to the following formula. The test was conducted by a two-run system. Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
As a result, at a treatment amount of 20 μg / seedling, compounds 1, 3, 5, 7, 8, 9, 11, 12, 13, 14, 16, 18, 20, 21, 22, 25, 26, 28, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 44, 45, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 58, 59, 60, 61, 62, 63, 64, 66, 67, 68, 69, 70, 71, 75, 76, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 99, 101, 102, 109, 111, 112, 151, 153, 154, 155, 156 are compounds 3, 7, 21, 28, 33, 36, 37, 38, 39, 41, 44, at a throughput of 2 μg / plant. 45, 46, 47, 48, 49, 53, 54, 56, 5 , 61 and 62 showed 80% or more of insecticidal activity mortality.

Test Example 2 Wheat beetle control test A wheat seedling root part 48 hours after sowing was treated with a chemical solution having a predetermined concentration prepared to be 10% acetone water. After 72 hours, the medicinal solution was absorbed from the root, and 10 larvae of the wheat beetle were released. Thereafter, it was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The mortality of the larvae was observed 6 days after the release, and the mortality rate was calculated according to the following formula. The test was conducted by a two-run system.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
As a result, at a treatment amount of 20 μg / seedling, compounds 3, 4, 7, 8, 9 were
Compounds 28, 30, 31, 33, 34, and 35 showed insecticidal activity with a death rate of 80% or more at a treatment amount of 10 μg / seedling.

Test Example 3 A leaf disc having a diameter of 5.0 cm was cut out from a cabbage grown in a pot- shaped control test pot pot and sprayed with a chemical solution having a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween 20). After air drying, the 2nd instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for viability 6 days after release, and the mortality was calculated according to the following formula. The test was conducted by a two-run system.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
As a result, the compounds 4, 8, 9, 20, 21, 22, 28, 30, 31, 33, 36, 37, 39, 41, 44, 45, 46, 47, 49, 51, 54,154,155 showed insecticidal activity with a death rate of 80% or more.

Test Example 4 Cotton Aphid Control Test A leaf disc having a diameter of 2.0 cm was cut out from a cucumber cultivated in a pot and sprayed with a chemical solution of a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween 20). . After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). Six days after release, the number of larvae on the leaves was observed, and the control value was calculated according to the following formula. The test was conducted by a two-run system.
Control value = {(Number of parasites in the untreated group after 6 days of treatment) − (Number of parasites in the treated group after 6 days of treatment) / (Number of parasites in the untreated group after 6 days of treatment)} × 100
As a result, the compound 3, 4, 7, 8, 9, 32, 33, 34, 35, 37, 38, 43, 46, 47, 107, 108, 113, 114 was converted to 50 ppm by treatment with 200 ppm of foliage. By the foliage treatment, Compound 71 showed a high density suppressing effect with a control value of 80 or more.

Test Example 5 Citrus thrips control test A leaf disk with a diameter of 2.8 cm was cut out from green beans grown in a pot and sprayed with a chemical solution of a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween 20). did. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for viability 6 days after release, and the mortality was calculated according to the following formula. The test was conducted by a two-run system.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
By treatment with 200 ppm of foliage, compounds 5, 6, 8, 9, 10, 11, 12, 14, 15, 38, 39, 153, 154, 155, and 156 were converted to compounds 4, 7, 8 by 100 ppm of foliage treatment. , 9, 16, 20, 21, 22, 23 are treated with 50 ppm of foliage treatment to give compounds 51, 52, 53, 54, 56, 57, 58, 59, 61, 62, 63, 64, 66, 77, 81. , 85, 87, 90, 92, 93, 102, 104, 107 are treated with 20 ppm of foliage treatment, and compounds 41, 44, 45, 46, 47 are treated with 10 ppm of foliage treatment, compounds 3, 4, 7, 8 9, 34, 35, 37, 46, 47, 51, 53, 58, 59, 62 showed a high insecticidal activity with a mortality rate of 80% or more.

Test Example 6 Spider Mite Control Test A 4 mL glass vial was charged with 30 μL of an acetone solution adjusted to a predetermined concentration, and a dry film of the compound of the present invention was prepared on the inner wall of the vial. More than 10 young mites were released and capped. The vial was placed in a temperature-controlled room at 25 ° C., 85% humidity and all dark conditions. Life and death were observed 2 days after release, and the mortality was calculated according to the following formula. The test was conducted by a two-run system.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
As a result, at the test concentration of 500 ppm, the compounds 11, 13, 15, 17, 32, 35, 36, 37, 43, 44, 46, 49, 53, 107, 154 have an insecticidal rate of 80% or more. Showed activity.

Claims (9)

Formula (I)

Formula (I)
[Where
R ₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
CH ₂ -O-R ₃ ,
_{CH 2 -O-CO-R 3} ,
(In the above group, R ₃ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
COR ₄ ,
COOR ₄ ,
CONHR ₄ ,
COSR ₄ ,
(In the above group, R ₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ,
SOR ₅ ,
SOOR ₅ ,
SNHR ₅ ,
CSNHR ₅ ,
CSSR ₅ ,
(In the above group, R ₅ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6} ,
CH ₂ -O-R ₆ ,
(In the above group, R ₆ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
Represents an optionally substituted C2-8 alkynyl group),
COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇ ,
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ,
SOR ₈ ,
SOOR ₈ ,
SNHR ₈ ,
CSR ₈ ,
CSNHR ₈ ,
CSSR ₈ ,
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
NH ₂
NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CO−R ₉ ) ₂ ,
N− (COO−R ₉ ) ₂ ,
N− (COS−R ₉ ) ₂ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
NH-R ₁₀ ,
NH-S-R ₁₀ ,
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−R ₁₁ ,
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−NR ₁₂ R ₁₃ ,
(In the above group, R ₁₂ and R ₁₃ are each independently
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group) or
O−R ₁₄ ,
(In the above group, R ₁₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
An optionally substituted C2-8 alkynyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
X is a nitrogen atom or CH] A pest control agent comprising one or more compounds represented by the formula: In the above formula (I), R ₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
COR ₄ ,
COOR ₄ ,
CONHR ₄ ,
COSR ₄ ,
(In the above group, R ₄ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ,
SOR ₅ ,
SOOR ₅ ,
SNHR ₅ ,
CSSR ₅ ,
(In the above group, R ₅ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
_{CH 2 -O-CO-R 6} ,
CH ₂ -O-R ₆ ,
(In the above group, R ₆ represents an optionally substituted C 1-8 alkyl group), COR ₇ ,
COOR ₇ ,
CONHR ₇ ,
COSR ₇ ,
(In the above group, R ₇ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ ,
SOOR ₈ ,
CSR ₈ ,
(In the above group, R ₈ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH ₂
NH-CO-R ₉ ,
NH-COO-R ₉ ,
NH-COS-R ₉ ,
NH-CSS-R ₉ ,
N− (CSS−R ₉ ) ₂ ,
(In the above group, R ₉ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH-R ₁₀ ,
N−S−R ₁₀ ,
(In the above group, R ₁₀ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group)
N = CH−R ₁₁ ,
(In the above group, R ₁₁ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group optionally substituted by a phenyl group), N = CH-NR ₁₂ R ₁₃ ,
(In the above group, R ₁₂ and R ₁₃ each independently represent a C1-8 alkyl group which may be substituted), or
O-R ₁₄
(R ₁₄ may be substituted C1~8 alkyl group,
Represents a benzyl group optionally substituted with a phenyl group),
X represents a nitrogen atom or CH,
The pest control agent of Claim 1 represented by these. In the above formula (I), R ₁ is a hydrogen atom, COR ₄ (R ₄ is an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ , or SNHR ₅ (R ₅ represents an optionally substituted C1~8 alkyl group or an optionally substituted phenyl group) represented by the pest control agent according to claim 2. In the above formula (I), R ₁ is a hydrogen atom, COR ₄ (R ₄ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ , or SNHR ₅ (R ₅ represents an optionally substituted C1-8 alkyl group or an optionally substituted phenyl group), R ₂ represents a hydrogen atom, COR ₇ (R ₇ represents an optionally substituted group) represents an C1~8 alkyl group or an optionally substituted phenyl group), or SR ₈ represents (R ₈ represents a C1~8 alkyl group which may be substituted), X represents a nitrogen atom The pest control agent according to claim 2, wherein Formula (I ')

[In the formula
R ₁ 'is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
Optionally substituted 5- or 6-membered heterocycloalkyl group,
COR ₄ ',
COOR ₄ ',
CONHR ₄ ',
COSR ₄ ',
(In the above group, R ₄ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocycle,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₅ ',
SOR ₅ ',
SOOR ₅ ',
SNHR ₅ ',
CSSR ₅ '
(In the above group, R ₅ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
R ₂ ′ is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted C2-8 alkenyl group,
A benzyl group optionally substituted by a phenyl group,
An optionally substituted aromatic 5- or 6-membered heterocyclic methyl group,
CH ₂ -O-CO-R ₆ ',
CH ₂ -O-R ₆ ',
(In the above group, R ₆ ′ represents an optionally substituted C1-8 alkyl group), COR ₇ ′,
COOR ₇ ',
CONHR ₇ ',
COSR ₇ ',
(In the above group, R ₇ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A benzyl group optionally substituted by a phenyl group,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
SR ₈ '
SOOR ₈ '
CSR ₈ ''
(In the above group, R ₈ ′ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH ₂
NH-CO-R ₉ ',
NH-COO-R ₉ ',
NH-COS-R ₉ ',
NH-CSS-R ₉ ',
N− (CSS−R ₉ ′) ₂ ,
(In the above group, R ₉ ′ is an optionally substituted C 1-8 alkyl group,
Represents an optionally substituted phenyl group),
NH-R ₁₀ ',
NH-S-R ₁₀ ',
(In the above group, R ₁₀ ′ is an optionally substituted C 1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group in which the phenyl group may be substituted,
Represents an optionally substituted 5- or 6-membered heterocycloalkyl group),
N = CH−R ₁₁ '
(In the above group, R ₁₁ 'is a hydrogen atom,
An optionally substituted C1-8 alkyl group,
An optionally substituted phenyl group,
A phenyl- (C1-4 alkyl) group optionally substituted with a phenyl group),
N = CH−NR ₁₂ 'R ₁₃ '
(In the above group, R ₁₂ ′ and R ₁₃ ′ each independently represent a C1-8 alkyl group which may be substituted),
O−R ₁₄ '
(In the above group, R ₁₄ ′ is an optionally substituted C 1-8 alkyl group,
Represents a benzyl group optionally substituted with a phenyl group),
X represents a nitrogen atom or CH, provided that R ₁ ′ and R ₂ ′ do not represent a hydrogen atom or acetyl group at the same time, and when R ₁ ′ is an acetyl group, R ₂ ′ represents NH ₂ It wo n’t happen]
And a salt thereof. In the above formula (I ′), R ₁ ′ is a hydrogen atom, COR ₄ ′ (R ₄ ′ represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), SR _The triazolone derivative according to claim 5, represented by ₅ ′ or SNHR ₅ ′ (R ₅ ′ represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), Its salt. In the above formula (I ′), R ₁ ′ is a hydrogen atom, COR ₄ ′ (R ₄ ′ represents an optionally substituted C 1-8 alkyl group, or an optionally substituted phenyl group), SR ₅ ′ or SNHR ₅ ′ (R ₅ ′ represents an optionally substituted C1-8 alkyl group or an optionally substituted phenyl group), R ₂ ′ represents a hydrogen atom, COR ₇ ′ ( R ₇ ′ represents an optionally substituted C1-8 alkyl group, or an optionally substituted phenyl group), or SR ₈ ′ (R ₈ ′ represents an optionally substituted C1-8 alkyl). The triazolone derivative and the salt thereof according to claim 5, wherein X represents a nitrogen atom. The pest control method using the pest control agent according to claim 1. A pest control method comprising applying the pest control agent according to claim 1 to a plant or soil.