JP2010047479A - Pest control composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new pest control composition that simultaneously controls pests which can not be controlled or has difficulty in the control by an insecticide, an acaricide or a fungicide by each alone. <P>SOLUTION: The pest control composition includes a compound represented by general formula (1), a known insecticide, a known acaricide or a known fungicide as active ingredients. (In the formula, A<SB>1</SB>, A<SB>2</SB>, A<SB>3</SB>and A<SB>4</SB>are each a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R<SB>1</SB>and R<SB>2</SB>are each independently a hydrogen atom, a 1-4C alkyl group or a 1-4C alkylcarbonyl group; G<SB>1</SB>and G<SB>2</SB>are mutually independently an oxygen atom or a sulfur atom; and Xs may be each the same or different and a hydrogen atom, a halogen atom, a 1-3C alkyl group or a trifluoromethyl group). <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a novel pest control composition exhibiting an excellent pest control action for labor-saving control of pests in crops.

  WO 2005/073165 pamphlet describes the amide derivative and its usage as an insecticide.

Further, International Publication No. 2003/008372 pamphlet, International Publication No. 2005/042474 pamphlet, and Pesticide Manual (Thirst Edition) describe insecticides, acaricides and fungicides.
International Publication No. 2005/073165 Pamphlet International Publication No. 2003/008372 Pamphlet International Publication No. 2005/042474 Pamphlet The pestiside manual

  However, the insecticides, acaricides and fungicides mentioned above have pests that cannot be controlled by themselves or are difficult.

  Therefore, an object of the present invention is to provide a new pest control composition capable of simultaneously controlling pests that cannot be controlled or difficult by using insecticides, acaricides or fungicides alone.

  As a result of intensive studies to solve the above problems, the present inventors have found that one or more compounds selected from the compound represented by the general formula (1), a known insecticide, The inventors have found that a plurality of pests can be efficiently controlled by combining one or two or more compounds selected from mite agents or known fungicides, and have completed the present invention.

That is, the present invention is as follows.
[1]
General formula (1)

{Where
A ₁ , A ₂ , A ₃ , A ₄ each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X is a hydrogen atom, a halogen atom or a trifluoromethyl group,
n represents an integer from 0 to 4,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1 -C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group , C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or, shows the C1-C6 perfluoroalkyl sulfonyl group, Y _2, Y ₄ each independently represent a hydrogen atom, a halogen atom or C1-C4 alkyl group, shows .) In either represented or,
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 An alkyl group, wherein at least one of Y ₆ and Y ₉ must be a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 halo; Represents an alkylsulfinyl group or a C1-C3 haloalkylsulfonyl group. } As an active ingredient, one or two or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides or known fungicides A pest control composition characterized by the above.

[2]
In the general formula (1), the compound represented by the general formula (1)
A ₁ , A ₂ , A ₃ , A ₄ each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X is a hydrogen atom, a halogen atom or a trifluoromethyl group,
n represents an integer from 0 to 4,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1 -C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group , C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or, shows the C1-C6 perfluoroalkyl sulfonyl group, Y _2, Y ₄ each independently represent a hydrogen atom, a halogen atom or C1-C4 alkyl group, shows .) In either represented or,
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 An alkyl group, wherein at least one of Y ₆ and Y ₉ must be a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 halo; A compound represented by an alkylsulfinyl group or a C1-C3 haloalkylsulfonyl group (wherein Y ₁ is a trifluoromethylthio group, Y ₂ and Y ₄ are hydrogen atoms, Y ₃ is a heptafluoroisopropyl group, and Y ₅ is Bromine atoms, X is a hydrogen atom, G ₁ and G ₂ are oxygen atoms, R ₁ and R ₂ are hydrogen atoms, and Q ₁ is an unsubstituted phenyl group. ] The pesticidal composition according to the above.

[3]
The compound represented by the general formula (1) is represented by the general formula (1a).

{Where
When either R ₁ or R ₂ is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both are a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group. ,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), Or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or a C1-C4 represents an alkyl group. here, Y _6, at least one is always C1-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru Represented by showing a Rusuruhoniru group.). } The pest control composition according to [1] or [2], which is a compound represented by

[4]
In the general formula (1a), the compound represented by the general formula (1)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) In the above [3], The pest control composition as described.

[5]
In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. The compound represented by Jill group, pest control composition according to [4].

[6]
In the general formula (1a), the compound represented by the general formula (1)
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1 -C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 A group having one or more substituents which may be the same or different and are selected from an alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; Phenyl group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), Or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or a C1-C4 represents an alkyl group. here, Y _6, at least one is always C1-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru A compound represented by showing a Rusuruhoniru group.), The [1] or pest control composition according to [2].

[7]
In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1 -C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 A group having one or more substituents which may be the same or different and are selected from an alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; Phenyl group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Represented by Jill group,
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) In the above [6], The pest control composition as described.

[8]
In the general formula (1a), the compound represented by the general formula (1)
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is fluorine atom, chlorine atom, iodine atom, C1-C4 alkyl group, C1- C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group shows a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl, Y ₂ and Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) Or the general formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or a C1-C4 represents an alkyl group. here, Y _6, at least one is always C1-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru A compound represented by showing a Rusuruhoniru group.), The [1] or pest control composition according to [2].

[9]
In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Represented by Jill group,
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is fluorine atom, chlorine atom, iodine atom, C1-C4 alkyl group, C1- C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group shows a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl, And Y ₂ and Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) The pest control composition as described in [8] above.

[10]
In the general formula (1a), the compound represented by the general formula (1)
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), Or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C2 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 represents an alkyl group. here, Y _6, at least one is always C2-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru A compound represented by showing a Rusuruhoniru group.), The [1] or pest control composition according to [2].

[11]
In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Represented by Jill group,
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl Group, or cyano group, Y ₃ represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), [10] A pest control composition as described in 1. above.

[12]
In the general formula (1), the compound represented by the general formula (1)
A ₁ , A ₂ , A ₃ , A ₄ each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
When either R ₁ or R ₂ is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both are a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group. ,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X is a hydrogen atom, a halogen atom or a trifluoromethyl group,
n represents an integer from 0 to 4,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ represents a C1-C4 alkoxy group or a C1-C4 haloalkoxy group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 halo An alkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, or a cyano group, Y ₃ represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, and Y ₂ and Y ₄ are each independently Represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group), or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 represents an alkyl group. here, Y _6, compound der represented by.) indicating at least one is always C1-C4 alkoxy group or a C1-C4 haloalkoxy group Y ₉ , Pest control composition according to [1].

[13]
In the general formula (1a), the compound represented by the general formula (1)
When either R ₁ or R ₂ is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both are a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group. ,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ represents a C1-C4 haloalkoxy group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, a C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y _2, Y ₄ each independently represent a hydrogen atom, a halogen atom Or a C1-C4 alkyl group.) The pest control composition as described in [12] above.

[14]
In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. It is a compound represented by Jill group, pest control composition according to [13].

[15]
Known insecticides, known acaricides or known fungicides are azinephos methyl, acephate, isoxathion, isofenphos, etion, etrimphos, oxydimethone methyl, oxydeprophos, quinalphos, chlorpyrifos, chlorpyrifosmethyl, chlorfenvinphos, cyanophos, Dioxabenzophos, dichlorvos, disulfoton, dimethylvinphos, dimethoate, sulprophos, diazinon, thiometone, tetrachlorbinphos, temefos, tebupyrimfos, terbufos, nared, bamidthione, pyraclofos, pyridafenthione, pyrimifosmethyl, fenitrothion, fenthion, fentoate, fentolfofo Thion, Flupyrazophos, Prothiophos, Propafos, Profenofos, Hoxime, Hosalon, Ho Met, formothion, folate, malathion, mecarbam, mesulfenphos, methamidophos, metidathion, parathion, methylparathion, monocrotophos, trichlorfone, O-ethylphenyl-4-phosphonothiothio, isazophosthiothiphosfothathionophos , Hosthiethane, phosphocarb, O-4-dimethylsulfamoylphenyl O, O-diethylphosphothioate, etoprophos, alanicarb, aldicarb, isoprocarb, etiophencarb, carbaryl, carbosulfan, xylcarb, pyricarb, pyricarb Nobucarb, furthiocarb, propoxyl, bendiocarb, benfuracarb, mesomil, metorcarb, 3,5-xylylmethylcarbamate, carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate, pentrin, cyclohalothrin, cyhalothrin, cyhalothrin , Lambda siharthrin, cyfluthrin, beta cyfluthrin, cypermethrin, alpha cypermethrin, zeta cypermethrin, silafluophene, tetramethrin, tefluthrin, deltamethrin, tralomethrin, bifenthrin, phenothrin, fenvalerate, fenpropatoline, framethrin fluretrin Nates, fulvalinates, flubrosinates , Permethrin, Resmethrin, Metofluthrin, Dimefluthrin, Profluthrin, Etofenprox, Cartap, Thiocyclam, Benzlutap, Acetamiprid, Imidacloprid, Clothianidin, Dinotefuran, Thiacloprid, Thiamethoxam, Nitenpyram, Flufluzuron, Flufluzuron Bistrifluron, fluazuron, flucycloxuron, flufenoxuron, hexaflumulone, lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyphenozide, diophenolan, cyromazine, pyriproxyfen, buprofezin, methoprene, hydroprene, quinoprene, triazamate, endosulfan The Rufenson, chlorbenzilate, dicophore, bromopropyrate, acetoprole, fipronil, etiprole, pyrethrin, rotenone, nicotine sulfate, abamectin, Bacillus thuringiensis, spinosad, acequinosyl, amideflumet, amitraz, etoxazole, quinomethionate, clofentezine , Phenbutadium oxide, dienochlor, cyhexatin, spirodiclofen, spiromesifen, tetradiphone, tebufenpyrad, binapacryl, bifenazate, pyridaben, pyrimidifene, phenazaquin, phenothiocarb, fenpyroximate, fluacrylimine, fluazinam, flufenzine, polyhexinactin, polyhexinactin Milbemectin, Ruff Nuron, mecarbam, methiocarb, mevinphos, formethanate, halfenprox, azadirachtin, diafenthiuron, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate, chlorfenapyr, tolfenpyrad, pymetrozine, phenoxycarb, hydramethylnon , Hydroxypropyl starch, pyridalyl, flufenelim, flubendiamide, flonicamid, metaflumizone, repimectin, tripropyrisocyclic, levamisole hydrochloride, morantel tartrate, dazomet, metam sodium,
General formula (AA)

[Wherein R ₅₁ represents a methyl group or a chloro group, R ₅₂ represents a methyl group, a chloro group, a bromo group or a cyano group, and R ₅₃ represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group. R ₅₄ represents a methyl group or an isopropyl group. A compound represented by
Compound (BB),

Triazimephone, hexaconazole, propiconazole, ipconazole, prochloraz, triflumizole, tebuconazole, epoxiconazole, difenoconazole, flusilazole, triazimenol, cyproconazole, metconazole, fluquinconazole, vitertanol, tetraconazole, tritico Nazole, flutriafor, penconazole, diconazole, fenbuconazole, bromconazole, imibenconazole, cimeconazole, microbutanyl, himexazole, imazalyl, framethopyl, tifluzamide, etridiazole, oxpoconazole, oxpoconazole fumarate, pefazoate , Prothioconazole, Pyriphenox, Phenarimol, Nuarimol, Bupirimate, Mepanipiri , Cyprozinyl, pyrimethanil, metalaxyl, oxadixyl, benalaxyl, thiophanate, thiophanate methyl, benomyl, carbendazim, fuberidazole, thiabendazole, manzeb, propineb, dineb, methylam, mannebu, dilam, thiuram, chlorothalonil, ethaboxamil, oxyfluxanil, oxyflurane , Silthiofam, Mepronil, Dimethomorph, Fenpropidin, Fenpropimorph, Spiroxamine, Tridemorph, Dodemorph, Flumorph, Azoxystrobin, Cresoxime Methyl, Metominostrobin, Orisatrobin, Fluoxastrobin, Trifloxystrobin, Dimoxystrobin , Pyraclostrobin, picoxystrobin, iprodione, procymidone, Nclozoline, clozolinate, fursulfamide, dazomet, methyl isothiocyanate, chloropicrin, metasulfocarb, hydroxyisoxazole, hydroxyisoxazole potassium, eclomesol, 1,3-Dichloropropene, carbam, basic copper chloride, basic copper sulfate, nonylphenol Copper sulfonate, copper oxine, dodecylbenzene sulfonate bisethylenediamine copper complex salt (II), anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide, inorganic sulfur, hydrated sulfur agent, lime sulfur mixture, zinc sulfate , Fentin, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hypochlorite, metallic silver, edifenphos, tolcrofosmethyl, fosetyl, iprobenphos, dinocap, pyrazophos, carpropamide, fusalide, trisi Crasol, Pyroxylone, Diclocimet, Phenoxanil, Kasugamycin, Validamycin, Polyoxin complex, Blasticidin S, Oxytetracycline, Mildiomycin, Streptomycin, Rapeseed oil, Machine oil, Bench avalicarb isopropyl, Iprovaricarb, Propamocarb, Dietofencarb, Fluorimide Fludioxanyl, fenpicuronyl, quinoxyphene, oxolinic acid, chlorothalonil, captan, phorpet, probenazole, acibenzoral S methyl, thiazinyl, cyflufenamide, fenhexamide, diflumetrim, metolaphenone, picobenzamide, proquinazide, famoxadone, cyazofamide, phenamidonal, oxamidon, zoxamid, Dithia , Fluazinam, Diclofluanid, Triphorine, Isoprothiolane, Ferimzone, Diclomedin, Teclophthalam, Pencyclon, Quinomethionate, Iminocazine Acetate, Iminocazine Albesylate, Ambamu, Polycarbamate, Thiadiazine, Chloroneb, Organonickel, Guazatine, Dodine, Kintozene, Tolylfluanid, anilazine, nitrotalisopropyl, fenitropan, dimethylolmol, benazole, harpin protein, flumetobar, mandipropamide, penthiopyrad,
General formula (CC)

[Wherein R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group and a heterocyclic alkyl group, R12 and R17 each represents a hydrogen atom, and R13 and R14 each represent Independently, it represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R15 and R16 each represent a hydrogen atom, and R18 represents an aryl group or a heterocycle. Or a compound represented by the general formula (DD)

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. The pest control composition according to any one of [1] to [14], which is a compound represented by the formula:

[16]
Known insecticides, known acaricides or known fungicides are fenitrothion, fenthion, isoxathione, acephate, buprofezin, pyriproxyfen, silafluophene, dinotefuran, imidacloprid, etofenprox, halfenprox, thiamethoxam, clothianidin, acetamiprid, nitenpyram, thiacloprid , Benfuracarb, Mesomil, Fenobucarb, Spinosad, Pymetrozine, Chromafenozide, Lepimectin, Fipronil,
General formula (AA)

[Wherein R ₅₁ represents a methyl group or a chloro group, R ₅₂ represents a methyl group, a chloro group, a bromo group or a cyano group, and R ₅₃ represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group. R ₅₄ represents a methyl group or an isopropyl group. A compound represented by
Compound (BB),

Fenproxymate, pyridaben, hexothiazox, fenbutazin oxide, tebufenpyrad, pyrimidifen, etoxazole, polynactin complex, milbemectin, acequinosyl, befenazate, spirodiclofen, dienochlor, spiromesifen, tetradiphone, chlorfenapyr, clofentegi, tolfenpyramide , Difenthiuron, flufenoxuron, penthiopyrado, fursulfamide, iminotadine albecylate, acibenzoral S methyl, ferimzone, pyroxylone, oryastrostrobin, azoxystrobin, carpropamide, diclocimet, probenazole, thiazinyl, isoprothiolane, tricyclazole, fusalide, kasugamycin , Fenoki Nil, mepronil, dichromedine, penclone, validamycin A, edifenphos, furametopil, tifluzamide, flutolanil, metminostrobin, iprobenphos, oxolinic acid, teclophthalam, cimeconazole, hydroxyisoxazole, picoxystrobin, flusilazole, carboxin, tebuconazole, tri Azimenol, difenoconazole, thiabendazole, fludioxanyl, metalaxyl, streptomycin,
General formula (CC)

[Wherein R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group and a heterocyclic alkyl group, R12 and R17 each represents a hydrogen atom, and R13 and R14 each represent Independently, it represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R15 and R16 each represent a hydrogen atom, and R18 represents an aryl group or a heterocycle. Or a compound represented by the general formula (DD)

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. ] The pest control composition as described in said [15] which is a compound represented by these.

[17]
Any one of [1] to [16] above, which contains 0.001 to 95% by weight of at least one compound selected from known insecticides, known acaricides and known fungicides. A pest control composition as described in 1. above.

[18]
A pest control method comprising applying the pest control composition according to the above [17] to a pest or a habitat of the pest.

[19]
A method for preventing damage by pests, which comprises applying the pest control composition according to [17] to plant seeds.

[20]
A method for preventing damage by pests, which comprises contacting the plant seeds with the pest control composition according to [17].

[21]
The prevention method according to the above [20], wherein the method for contacting the plant seeds is a seed spraying treatment, a smearing treatment, a dipping treatment, or a dressing treatment.

[22]
Plant seeds are corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper and rape seed, taro, potato, The prevention method according to the above [19], which is a potato, konjac seed, edible lily or tulip bulb.

[23]
The prevention method according to the above [22], wherein the plant seed is a transformed seed.

[24]
Plant seeds to which the pesticidal composition according to the above [17] is applied.

[25]
A method for preserving plant seeds, comprising applying the pest control composition according to the above [17] to plant seeds.

[26]
The preservation method according to [25], wherein the application method to the plant seed is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment or fumigation / smoke treatment.

[27]
A method for preserving a crop, comprising applying the pest control composition according to the above [17] to a crop of an agricultural plant.

[28]
[27] The preservation method according to [27], wherein the application method to the harvest of the agricultural plant is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment, fumigation / smoke treatment, or pressure injection.

  According to the present invention, a known insecticide, a known acaricide, or a known fungicide alone does not provide a sufficient control effect, and also has a remarkable control effect against a plurality of pests exhibiting drug resistance and the like. It is possible to provide a pest control composition having a remarkable control effect against a plurality of pests exhibiting the above and exhibiting pests that could not be controlled alone and drug resistance. Therefore, the pest control composition of the present invention can greatly contribute to the labor saving of agriculture.

The present invention is described in detail below.
In the general formula, the expression “Ca—Cb (a, b represents an integer of 1 or more)”, for example, the expression “C1-C3” means 1 to 3 carbon atoms. , “C2-C6” means 2 to 6 carbon atoms, and “C1-C4” means 1 to 4 carbon atoms. “N-” means normal, “i-” means iso, “s-” means secondary, and “t-” means tertiary.

Specific examples of the “halogen atom” and each “group” in the general formula are shown below.
“Halogen atom” includes fluorine atom, chlorine atom, bromine atom or iodine atom.

Examples of the “C1-C3 alkyl group” include linear or branched alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, etc.
As the “C1-C4 alkyl group”, in addition to the “C1-C3 alkyl group”, for example, a linear or branched chain such as n-butyl, s-butyl, i-butyl, t-butyl, cyclopropylmethyl, etc. An alkyl group having 1 to 4 carbon atoms,
The “C1-C6 alkyl group” includes, for example, n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl, 4-methyl-2-pentyl in addition to “C1-C4 alkyl group” Linear or branched alkyl groups having 1 to 6 carbon atoms such as 3-methyl-n-pentyl and cyclobutylmethyl,
Examples of the “C1-C3 haloalkyl group” include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, bromodifluoromethyl, 1-fluoroethyl. 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl 2-bromoethyl, 2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl, pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo- n-propyl, 1,3-difluoro-2-propyl, 1,3-di Olo-2-propyl, 1,1,1-trifluoro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl, heptafluoro-n A linear or branched alkyl group having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as -propyl;
As the “C1-C4 haloalkyl group”, in addition to the “C1-C3 haloalkyl group”, for example, 4-fluoro-n-butyl, 4-chloro-n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, etc. A linear or branched alkyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, and
Examples of the “C2-C4 alkenyl group” include alkenyl groups having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, and 3-butenyl. Examples of the “—C4 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, A straight chain having a double bond in a carbon chain substituted by one or more halogen atoms which may be the same or different, such as 4,4-difluoro-3-butenyl and 3,4,4-tribromo-3-butenyl. A chain or branched alkenyl group having 2 to 4 carbon atoms, and
Examples of the “C2-C4 alkynyl group” include a straight chain or branched chain having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc. An alkynyl group having 2 to 4 carbon atoms, and examples of the “C 2 -C 4 haloalkynyl group” include a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. A linear or branched alkynyl group having 2 to 4 carbon atoms having
Examples of the “C3-C6 cycloalkyl group” include cycloalkyl groups having 3 to 6 carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like. , As the “C 3 -C 6 halocycloalkyl group”, for example, one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like And a cycloalkyl group having 3 to 6 carbon atoms having a cyclic structure substituted by
Examples of the “C1-C3 alkoxy group” include linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy, etc., and “C1-C4 Examples of the “alkoxy group” include, in addition to “C1-C3 alkoxy group”, linear or branched alkoxy having 1 to 4 carbon atoms such as n-butyloxy, isobutyloxy, s-butyloxy, t-butyloxy and the like. Groups,
Examples of the “C1-C3 haloalkoxy group” include trifluoromethoxy, difluoromethoxy, monofluoromethoxy, pentafluoroethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2-fluoro Ethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2,2-dichloroethoxy, 2,2,2-trichloroethoxy, 3-fluoro-n-propyloxy, 2 , 2,3,3-tetrafluoro-n-propyloxy, 2,2,3,3,3-pentafluoro-n-propyloxy, 1,3-difluoro-2-propyloxy, 1-chloro-3- Fluoro-2-propyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, 2,2,2-trifluoro-1-tri Substituted with one or more halogen atoms, which may be the same or different, such as fluoromethylethoxy, 2-trifluoromethoxy-1,1,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, etc. Examples thereof include linear or branched haloalkoxy groups having 1 to 3 carbon atoms. The “C1-C4 haloalkoxy group” includes, for example, 1,1,1 in addition to the “C1-C3 haloalkoxy group”. 1 to 3 linear or branched carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 1,3,3,4,4,4-octafluoro-2-butyloxy 4 haloalkoxy groups are mentioned,
Examples of the “C1-C3 alkylthio group” include linear or branched alkylthio groups having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like. As the “C1-C4 alkylthio group”, in addition to the “C1-C3 alkylthio group”, for example, a linear or branched chain such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio, etc. Examples thereof include alkylthio groups having 1 to 4 carbon atoms. Examples of the “C1-C3 haloalkylthio group” include trifluoromethylthio, pentafluoroethylthio, 2-fluoroethylthio, 2,2,2-trifluoroethyl. Thio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, 1,1,2,3,3 -Hexafluoropropylthio, 2,2,2-trifluoro-1-trifluoromethylethylthio, 2-trifluoromethoxy-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoro Examples thereof include a linear or branched alkylthio group having 1 to 3 carbon atoms substituted with one or more halogen atoms, which may be the same or different, such as ethylthio, and “C1-C4 haloalkylthio group” "In addition to" C1-C3 haloalkylthio group ", for example, nonafluoro-n-butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio and the like may be the same or different. A linear or branched alkylthio group having 1 to 4 carbon atoms substituted with at least one halogen atom;
Examples of the “C1-C3 alkylsulfinyl group” include linear or branched alkyl having 1 to 3 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like. Examples of the “C1-C3 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro- i-propylsulfinyl, 1,1,2,3,3,3-hexafluoropropylsulfinyl, 2,2,2-trifluoro-1-trifluoromethylethylsulfinyl, 2-trifluoromethoxy-1,1,2 -Trifle 1 to 3 linear or branched carbon atoms substituted by one or more halogen atoms, which may be the same or different, such as roethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, etc. An alkylsulfinyl group of
Examples of the “C1-C3 alkylsulfonyl group” include linear or branched alkyl having 1 to 3 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like. Examples of the “C1-C3 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro- i-propylsulfonyl, 1,1,2,3,3,3-hexafluoropropylsulfonyl, 2,2,2-trifluoro-1-trifluoromethylethylsulfonyl, 2-trifluoromethoxy-1,1,2 -Trifluoroethylsulfonyl, 1,1, , For example, linear or branched alkylsulfonyl group having 1 to 3 carbon atoms which is substituted by the same or may be different one or more halogen atoms, such as 2-tetrafluoroethyl sulfonyl,
Examples of the “arylsulfonyl group” include carbon atoms having an aromatic ring such as phenylsulfonyl, p-toluenesulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl, acenaphthylenylsulfonyl and the like. 6-14 arylsulfonyl groups are mentioned,
Examples of the “C1-C4 alkylamino group” include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino, 2,2,2-trifluoroethylamino and the like. Examples thereof include a linear, branched, or cyclic alkylamino group having 1 to 4 carbon atoms. Examples of the “di-C1-C4 alkylamino group” include dimethylamino, diethylamino, N-ethyl-N-methylamino. An amino group substituted with two linear or branched alkyl groups having 1 to 4 carbon atoms, which may be the same or different, and the like,
Examples of the “C1-C4 alkylcarbonyl group” include linear, branched or cyclic alkylcarbonyl groups having 1 to 4 carbon atoms such as formyl, acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like. ,
Examples of the “C1-C4 haloalkylcarbonyl group” include fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl, 2,2 , 3,3,3-pentafluoropropionyl and the like, which are linear or branched alkylcarbonyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different. ,
Examples of the “C1-C4 alkylcarbonyloxy group” include linear or branched alkylcarbonyloxy groups having 1 to 4 carbon atoms such as acetoxy and propionyloxy,
Examples of the “C1-C4 alkoxycarbonyl group” include linear or branched alkoxycarbonyl groups having 1 to 4 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, etc.
Examples of the “C1-C4 perfluoroalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i -A linear or branched alkyl group having 1 to 4 carbon atoms, all substituted with fluorine atoms such as butyl, etc. is shown, and "C2-C6 perfluoroalkyl group" means, for example, pentafluoro Fluorine such as ethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, perfluoro-n-pentyl, perfluoro-n-hexyl Straight or branched carbon atoms having 2 to 6 carbon atoms, all substituted by atoms Alkyl group, and the like,
Examples of the “C 1 -C 6 perfluoroalkylthio group” include trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro- linear or branched alkylthio groups having 1 to 6 carbon atoms, which are all substituted with fluorine atoms such as i-butylthio, perfluoro-n-pentylthio, perfluoro-n-hexylthio and the like,
Examples of the “C1-C6 perfluoroalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2 1 to 6 linear or branched carbon atoms all substituted with fluorine atoms such as -butylsulfinyl, nonafluoro-i-butylsulfinyl, perfluoro-n-pentylsulfinyl, perfluoro-n-hexylsulfinyl, etc. An alkylsulfinyl group of
Examples of the “C1-C6 perfluoroalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2 1 to 6 linear or branched carbon atoms all substituted by fluorine atoms such as -butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-hexylsulfonyl, etc. Of the alkylsulfonyl group.

  The compounds represented by the general formula (1) and the general formula (1a) may contain one or a plurality of asymmetric carbon atoms or asymmetric centers in the structural formula. In some cases, the compounds represented by the general formula (1) and the general formula (1a) include all the optical isomers and a mixture in which they are contained in an arbitrary ratio. Moreover, although the compound represented by General formula (1) and General formula (1a) may have two or more types of geometric isomers originating in a carbon-carbon double bond in the structural formula, The compounds represented by the general formula (1) and the general formula (1a) include all geometric isomers and a mixture in which they are contained in an arbitrary ratio.

As the compounds represented by the general formula (1) and the general formula (1a), compounds having the following atoms or groups can be mentioned as preferred compounds.
A ₁ , A ₂ , A ₃ and A ₄ are preferably A ₁ is a carbon atom, a nitrogen atom or an oxidized nitrogen atom, and at the same time A ₂ , A ₃ and A ₄ are all carbon atoms, and more preferably In A, A ₁ , A ₂ , A ₃ and A ₄ are all carbon atoms.

R ₁ is preferably a hydrogen atom, a C1-C4 alkyl group, or an acetyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
R ₂ is preferably a hydrogen atom, a C1-C4 alkyl group, or an acetyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
Preferably a G _1, G ₂ is, G _1, G ₂ are both _an oxygen atom.
X is preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a fluorine atom.
n is preferably 0, 1 or 2, and more preferably 0 or 1.
X ₁ is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom.
X ₂ is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
X ₃ and X ₄ are preferably hydrogen atoms.

Q ₁ is preferably a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
A pyridyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Is Jill group.

Q ₁ is more preferably a phenyl group,
Fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, A substituted phenyl group having 1 to 3 identical or different substituents selected from a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group, and a nitro group;
A pyridyl group, or
Fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, A substituted pyridyl group having 1 to 2 substituents which may be the same or different, selected from a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group.

Q ₂ is preferably a substituted phenyl group or a substituted pyridyl group represented by general formula (2) or general formula (3).

In general formula (2), Y ₁ is preferably trifluoromethylthio group, pentafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, trifluoromethylsulfinyl group, pentafluoroethyl. Sulfinyl group, heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group , Methoxy group, ethoxy group, trifluoromethoxy group, pentafluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy More preferably, trifluoromethylthio group, pentafluoroethylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, trifluoromethoxy group, 2-fluoro An ethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group.

In general formula (2), Y ₅ is preferably fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-butyl. Group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, pentafluoroethylthio group, heptafluoro-i-propylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, hepta Fluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, cyano group, Methoxy group, Etoxy Group, n-propyloxy group, trifluoromethoxy group, pentafluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloro An ethoxy group.

In general formula (3), Y ₆ and Y ₉ are preferably each independently a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, n-butyl group, 2-butyl group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, pentafluoroethylthio group, heptafluoro-i-propylthio group, trifluoromethylsulfinyl group , Pentafluoroethylsulfinyl group, heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i -Propylsulfonyl group, cyano Group, methoxy group, ethoxy group, n-propyloxy group, trifluoromethoxy group, pentafluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2 , 2,2-trichloroethoxy group, and any one of Y ₆ and Y ₉ is always trifluoromethylthio group, pentafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, Fluoromethylsulfinyl group, pentafluoroethylsulfinyl group, heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, Heptafluoro-i- Propylsulfonyl group, methoxy group, ethoxy group, trifluoromethoxy group, pentafluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2, 2-trichloroethoxy group, more preferably, any one of Y ₆ and Y ₉ is always trifluoromethylthio group, pentafluoroethylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, trifluoromethylsulfonyl Group, pentafluoroethylsulfonyl group, trifluoromethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group.

Formula (3) in, as preferably _{Y 2, Y 4, Y 7} , independently, a hydrogen atom, a halogen atom, a methyl group, more preferably a hydrogen atom,
Y ₃ is preferably pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, trifluoro Methylthio group, pentafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, nonafluoro-n-butylthio group, nonafluoro-2-butylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group , Heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, nonafluoro-n-butylsulfinyl group, nonafluoro-2-butylsulfinyl group, trifluoromethylsulfonyl group, pentafluoro Tylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group, pentafluoroethoxy group, 1,1,1,3 , 3,3-hexafluoro-i-propyloxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, 2,2,2-trifluoro-1-trifluoromethylethoxy group, 2, -Trifluoromethoxy-1,1,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group,
Y ₈ is preferably pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, trifluoro Methylthio group, pentafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, nonafluoro-n-butylthio group, nonafluoro-2-butylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group , Heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, nonafluoro-n-butylsulfinyl group, nonafluoro-2-butylsulfinyl group, trifluoromethylsulfonyl group, pentafluoro Tylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group, pentafluoroethoxy group, 1,1,1,3 , 3,3-hexafluoro-i-propyloxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, 2,2,2-trifluoro-1-trifluoromethylethoxy group, 2, -Trifluoromethoxy-1,1,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group.

In the general formula described below, L is preferably a chlorine atom, a bromine atom, or a hydroxy group.
R ₁ a is preferably a hydrogen atom, a C1-C4 alkyl group or an acetyl group, more preferably a hydrogen atom, a methyl group or an ethyl group.
R ₂ a is preferably a hydrogen atom, a C1-C4 alkyl group, or an acetyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
As Preferably _{G 1 a, G 2 a,} G 1 a, G 2 a are both an oxygen atom.
X ₁ a is preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a fluorine atom.
X ₂ a is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
X ₃ a and X ₄ a are preferably hydrogen atoms.
The preferred Y ₁ a, trifluoromethylthio group, pentafluoroethylthio group, heptafluoro -n- propylthio, heptafluoro -i- propylthio group, trifluoromethyl sulfinyl group, pentafluoroethyl sulfinyl group, heptafluoro -n -Propylsulfinyl group, heptafluoro-i-propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, methoxy group, ethoxy group, A trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,2-trichloroethoxy group, and Preferably, trifluoromethylthio group, pentafluoroethylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, trifluoromethoxy group, 2-fluoroethoxy group, They are 2,2-difluoroethoxy group and 2,2,2-trifluoroethoxy group.

Y ₂ a and Y ₄ a are preferably a hydrogen atom, a halogen atom or a methyl group, and more preferably a hydrogen atom.
Y ₅ a is preferably a fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-butyl group, trifluoromethyl group, Methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, pentafluoroethylthio group, heptafluoro-i-propylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, heptafluoro-n-propylsulfinyl group , Heptafluoro-i-propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, cyano group, methoxy group, ethoxy group, n -Propyl Alkoxy group, a trifluoromethoxy group, pentafluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoro-ethoxy, 2,2,2-trifluoroethoxy group, a 2,2,2-trichloroethoxycarbonyl group.

R _a and R _b are each preferably a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group or a heptafluoro-n-propyl group, and more preferably a fluorine atom, a trifluoromethyl group or a pentafluoro group, respectively. It is an ethyl group.
_Rc is preferably a hydroxy group, chlorine atom, bromine atom, iodine atom, methoxy group, ethoxy group, methylsulfonyloxy group, trifluoromethylsulfonyloxy group, phenylsulfonyloxy group, p-toluenesulfonyloxy group, acetoxy group , A trifluoroacetoxy group, more preferably a hydroxy group, a chlorine atom, a bromine atom, a methoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, a p-toluenesulfonyloxy group, More preferably, they are a hydroxy group, a chlorine atom, and a bromine atom.
R _c ′ is preferably a hydroxy group.
R _c ″ is preferably a chlorine atom or a bromine atom.
J and J ′ are each preferably a hydroxy group, a chlorine atom, or a bromine atom, and more preferably a chlorine atom.

Although the manufacturing method of the compound represented by General formula (1) and General formula (1a) below is shown, a manufacturing method is not limited to the manufacturing method shown below.
The following Q ₂ a shown in the production method of the general formula (2)

(Wherein, _{Y 1, Y 2, Y 3} , Y 4, Y 5 have the same meanings as _{Y 1, Y 2, Y 3} , Y 4, Y 5 in the [1].)
General formula (3)

_{(Wherein, Y 6, Y 7, Y} 8, Y 9 have the same meanings as _{Y 6, Y 7, Y 8} , Y 9 in the [1].) Or the general formula (5)

(In the formula, Y ₁ a, Y ₂ a, Y ₄ a, Y ₅ a, R _a , R _b , R _c are Y ₁ a, Y ₂ a, Y ₄ a, Y ₅ a in the above [15]. , R _a , R _b , and R _c ).

  Manufacturing method 1

(In General Formula (19) to General Formula (26), A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, and Q ₁ are in the above [1]. Is synonymous with A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , and L has a leaving ability such as a halogen atom and a hydroxy group Represents a functional group.)

1- (i) General formula (19) + General formula (20) → General formula (21)
A compound represented by the general formula (21) can be produced by reacting the compound represented by the general formula (19) and the compound represented by the general formula (20) in a suitable solvent or without a solvent. it can. In this step, an appropriate base can be used.

  The solvent is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as water, benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, Chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, ketones such as acetone, methyl isobutyl ketone and cyclohexanone Amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide and the like. These solvents may be used alone or in combination of two or more. Combined and can be used.

  Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, and potassium carbonate. Examples thereof include carbonates, phosphates such as dipotassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metal alcoholates such as sodium methoxide and sodium ethoxide, and the like. . These bases may be appropriately selected and used within a range of 0.01 to 50 times molar equivalent to the compound represented by the general formula (19). The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours.

  For example, when the compound represented by the general formula (19) is an m-nitro aromatic carboxylic acid halide, the m-nitro aromatic carboxylic acid halide is reacted with a corresponding aromatic carboxylic acid and a halogenating agent, It can be manufactured easily. Examples of the halogenating agent include halogenating agents such as thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, and phosgene.

  On the other hand, the compound represented by the general formula (21) is produced from the compound represented by the general formula (20) and the compound represented by the general formula (20) without using a halogenating agent. It is possible. For example, Chem. Ber. p. 788 (1970), that is, a method using a condensing agent using N, N′-dicyclohexylcarbodiimide by appropriately using an additive such as 1-hydroxybenzotriazole. Examples of other condensing agents used in this case include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1,1'-carbonylbis-1H-imidazole, and the like.

  In addition, as another method for producing the compound represented by the general formula (21), a mixed acid anhydride method using chloroformates can be shown. Am. Chem. Soc. By following the method described on page 5012 (1967), the compound represented by the general formula (21) can be produced. Examples of the chloroformate used in this case include isobutyl chloroformate and isopropyl chloroformate. In addition to the chloroformates, diethylacetyl chloride, trimethylacetyl chloride and the like can be used.

  Both the method using a condensing agent and the mixed acid anhydride method are not limited to the solvent, reaction temperature, and reaction time described in the above literature, and an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate. What is necessary is just to select suitably temperature and reaction time according to progress of reaction.

1- (ii) General formula (21) → General formula (22)
The compound represented by the general formula (21) can be led to the compound represented by the general formula (22) by a reduction reaction. Examples of the reduction reaction include a method using a hydrogenation reaction and a method using a metal compound (for example, stannous chloride (anhydride), iron powder, zinc powder, etc.).
In the former method, the reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, under a hydrogen atmosphere. Examples of the catalyst include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, platinum catalysts, cobalt catalysts, ruthenium catalysts, rhodium catalysts, etc., and solvents include water, methanol, ethanol, etc. Alcohols, aromatic hydrocarbons such as benzene and toluene, linear or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate. The pressure is 0.1 to 10 MPa, the reaction temperature is −20 ° C. to the reflux temperature of the solvent to be used, and the reaction time is appropriately selected within the range of several minutes to 96 hours, and the compound of the general formula (22) is selected. It can be manufactured efficiently.
As the latter method, “Organic Synthesis” Coll. Vol. III P.I. According to the conditions described in 453, a method of using stannous chloride (anhydride) as a metal compound can be exemplified.

1- (iii) General formula (22) + General formula (23) → General formula (24)
A compound represented by the general formula (24) can be produced by reacting the compound represented by the general formula (22) with the compound represented by the general formula (23) in an appropriate solvent or without a solvent. it can. In this step, an appropriate base can be used.

  The solvent is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as water, benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, Linear or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, ketones such as acetone, methyl isobutyl ketone and cyclohexanone , Dimethylformamide, amides such as dimethylacetamide, nitriles such as acetonitrile, and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents may be used alone or in combination of two or more. Can be used Kill.

  Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, and potassium carbonate. Examples thereof include carbonates, phosphates such as dipotassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metal alcoholates such as sodium methoxide and sodium ethoxide, and the like. . These bases may be appropriately selected and used within a range of 0.01 to 50 times molar equivalent to the compound represented by the general formula (22). The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours. It can also be produced by a method using the condensing agent described in 1- (i) above or a mixed acid anhydride method.

1- (iv) General formula (24) + General formula (25) → General formula (26)
A compound represented by the general formula (26) by reacting a compound represented by the general formula (24) with an alkyl compound having a leaving group represented by the general formula (25) in a solvent or without a solvent. Can be manufactured. Examples of the compound represented by the general formula (25) include alkyl halides such as methyl iodide, ethyl iodide, and n-propyl bromide. In this step, a suitable base or solvent can be used, and as the base or solvent, those exemplified in the above 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of said 1- (i).
Alternatively, instead of the compound represented by the general formula (25), an alkylating agent such as dimethyl sulfate or diethyl sulfate may be reacted with the compound represented by the general formula (24). It is possible to produce the compound represented by 26).

  Manufacturing method 2

(Formula (20), the general formula (23), and the general formula (27) - In the general formula _{(30), A 1, A} 2, A 3, A 4, G 1, G 2, R 1, R 2 , X, n, and Q ₁ have the same meanings as A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, and Q _{1 in} [1], and L Represents a functional group having a leaving ability such as a halogen atom or a hydroxy group, and Hal represents a chlorine atom or a bromine atom.)

2- (i) General formula (27) + General formula (23) → General formula (28)
The solvent and the base described in 1- (i) above are appropriately selected, or the carboxylic acid having an amino group represented by the general formula (27) and the general formula (23) according to the solvent-free or base-free conditions. Carboxylic acids having an acylamino group represented by the general formula (28) can be produced by reacting with the compound represented. The reaction time and reaction temperature can be appropriately selected from the conditions described in 1- (i) above.

2- (ii) General formula (28) → General formula (29)
Known reaction of a compound represented by the general formula (28) with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride, etc. By the halogenation reaction, a compound represented by the general formula (29) can be produced.

2- (iii) General formula (29) + General formula (20)-> General formula (30)
The solvent and the base described in 1- (i) above are appropriately selected, or the compound represented by the general formula (29) and the compound represented by the general formula (20) are selected according to the solventless or abasic conditions. By reacting, the compound represented by the general formula (30) can be produced. The reaction time and reaction temperature can be appropriately selected from the conditions described in 1- (i) above.

2- (iv) General formula (28) + General formula (20) → General formula (30)
The compound represented by the general formula (28) is reacted with the compound represented by the general formula (20) according to the conditions using the condensing agent described in 1- (i) above or the conditions using the mixed acid anhydride method. By making it, the compound represented by General formula (30) can be manufactured.

  Manufacturing method 3

(In the general formula (48) and the general formula (49), A ₁ , A ₂ , A ₃ , A ₄ , X, n, G ₂ , R ₂ are A ₁ , A ₂ , A ₃ in the above [1]. , A ₄ , X, n, G ₂ and R _2. )
The compound represented by the general formula (48) is reacted with an appropriate reagent in an appropriate solvent or without a solvent using an appropriate base to produce the compound represented by the general formula (49). be able to.

  Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, chloroform, and the like. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitrile, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, 1,3-dimethyl 2-imidazolidinone, sulfolane, can indicate dimethyl sulfoxide, water, etc. These solvents may be used alone or as a mixture of two or more.

  Examples of the base include organic bases such as triethylamine, tributylamine, pyridine and 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium bicarbonate and potassium carbonate, Phosphate salts such as potassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metal alkoxides such as sodium methoxide and sodium ethoxide, and organic lithiums such as n-butyllithium And Grignard reagents such as ethylmagnesium bromide.

  These bases may be appropriately selected and used within a range of 0.01 to 50 times molar equivalent to the compound represented by the general formula (48).

  Examples of the reactive agent include alkyl halides such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide, allyl halides such as allyl iodide, odor, and the like. And propargyl halides such as propargyl halide, acyl halides such as acetyl chloride, acid anhydrides such as trifluoroacetic anhydride, and alkyl sulfates such as dimethyl sulfate and diethyl sulfate. These reactants may be appropriately selected or used as a solvent in the range of 1 to 5 molar equivalents relative to the compound represented by the general formula (48). The reaction temperature may be appropriately selected from −80 ° C. to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.

  Manufacturing method 4

(In the general formula (22) and the general formula (50), A ₁ , A ₂ , A ₃ , A ₄ , X, n, G ₂ , R ₂ are A ₁ , A ₂ , A ₃ in the above [1]. , A ₄ , X, n, G ₂ and R _2. )

4- (i) General formula (22) → General formula (50)
By reacting the compound represented by the general formula (22) with an aldehyde or ketone in an appropriate solvent or without a solvent, adding an appropriate catalyst, and reacting under a hydrogen atmosphere, the general formula (50) The compounds represented can be produced.

  Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, chloroform, and the like. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether Rusuruhokishido, alcohols such as methanol, ethanol, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more.

  Examples of the catalyst include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts, and the like.

Examples of aldehydes include aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and bromoacetaldehyde.
Examples of ketones include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.
The reaction pressure may be appropriately selected within the range of 0.1 MPa to 10 MPa.
The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent to be used, and the reaction time may be appropriately selected within the range of several minutes to 96 hours.

4- (ii) General formula (22) → General formula (50) (Alternative method 1)
A compound represented by the general formula (50) is reacted with an aldehyde or a ketone in an appropriate solvent or without a solvent, and treated with an appropriate reducing agent, whereby the compound represented by the general formula (50) is treated. Can be manufactured.

  Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, chloroform, and the like. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether Rusuruhokishido, alcohols such as methanol, ethanol, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more.

  Examples of the reducing agent include borohydrides such as sodium borohydride, sodium cyanoborohydride, and sodium triacetoxyborohydride.

Examples of aldehydes include aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and bromoacetaldehyde.
Examples of ketones include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.

  The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.

4- (iii) General formula (22) → General formula (50) (Alternative method 2)
In the general formula (50), R ₁ is a methyl group by reacting the compound represented by the general formula (22) with a formylating agent in an appropriate solvent or without solvent and adding an appropriate additive. Compounds can be produced.

  Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, chloroform, and the like. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether Rusuruhokishido, alcohols such as methanol, ethanol, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more.

Examples of the formylating agent include formic acid anhydrides such as formaldehyde, formic acid, fluoroformic acid, formyl (2,2-dimethylpropionic acid), formic acid esters such as phenyl formate, pentafluorobenzaldehyde, and oxazole. it can.
Examples of the additive include inorganic acids such as sulfuric acid, organic acids such as formic acid, borohydrides such as sodium borohydride and sodium cyanoborohydride, boronic acid, lithium aluminum hydride, and the like.

  The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.

  Manufacturing method 5

(In the general formula (31) and the general formula _{(32), R 2, Y} 2, Y 3, Y 4, Y 5 R 2 in the _{[1], Y 2, Y 3, Y} 4, Y 5 is And m represents 1 or 2, and Rf represents a C1-C3 haloalkyl group.)
By using an appropriate oxidizing agent, the compound represented by the general formula (32) can be produced from the compound represented by the general formula (31), for example, see Tetrahedron Lett. The method described on page 4955 (1994) can be shown.

  Examples of the oxidizing agent include organic peracids such as m-chloroperbenzoic acid, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetroxide, acyl nitrate, iodine, bromine, N -Bromosuccinimide, iodosylbenzyl, t-butyl hypochlorite, etc. can be shown. What is necessary is just to select an oxidizing agent suitably in the range of 1-5 times molar equivalent with respect to the compound represented by General formula (31).

  Appropriate additives can be added, and examples thereof include ruthenium (III) chloride.

  The solvent used in this step is not limited to the solvents described in the above documents, and any solvent may be used as long as it does not significantly inhibit the progress of this reaction. These solvents may be used alone or in combination of two or more. Can be used. The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours.

  Hereinafter, Tables 1 to 6 show typical compounds represented by the general formula (1) and the general formula (1a) having insecticidal action, but the present invention is not limited thereto. .

In the table, “n-” represents normal, “Me” represents methyl group, “Et” represents ethyl group, “n-Pr” represents normal propyl group, “i-Pr” represents isopropyl group, “N-Bu” represents a normal butyl group, “i-Bu” represents an isobutyl group, “s-Bu” represents a secondary butyl group, “t-Bu” represents a tertiary butyl group, and “H” represents a hydrogen atom. `` O '' is an oxygen atom, `` S '' is a sulfur atom, `` C '' is a carbon atom, `` N '' is a nitrogen atom, `` F '' is a fluorine atom, `` Cl '' is a chlorine atom, “Br” represents a bromine atom, “I” represents an iodine atom, “CF ₃ ” represents a trifluoromethyl group, “C ₂ F ₅ ” represents a pentafluoroethyl group, “nC ₃ F ₇ ” represents a heptafluoro- n-propyl group, “iC ₃ F ₇ ” represents a heptafluoro-i-propyl group, “2-C ₄ F ₉ ” represents a nonafluoro-2-butyl group, and “SCF _3- ” represents a trifluoromethylthio group. , " “SC ₂ F ₅ ” represents a pentafluoroethylthio group, “SnC ₃ F ₇ ” represents a heptafluoro-n-propylthio group, “S (O) CF ₃ ” represents a trifluoromethylsulfinyl group, “S (O) the C ₂ F ₅ "is pentafluoroethyl sulfinyl group," S (O) -nC ₃ F ₇ "is heptafluoro -n- propyl sulfinyl group," SO ₂ CF ₃ "is trifluoromethylsulfonyl group," “SO ₂ C ₂ F ₅ ” represents a pentafluoroethylsulfonyl group, “SO ₂ -nC ₃ F ₇ ” represents a heptafluoro-n-propylsulfonyl group, “OMe” represents a methoxy group, and “OEt” represents an ethoxy group. , “OCF ₃ ” represents a trifluoromethoxy group, “OCH ₂ CF ₃ ” represents a 2,2,2-trifluoroethoxy group, and “OCH (CF ₃ ) ₂ ” represents 1,1,1,3,3, 3-hexafluoro-2-propyloxy group, “Ac” represents an acetyl group, respectively. .
General formula (A)

一般式（A）

General formula (A)

一般式（A）

General formula (A)

一般式（B）

General formula (B)

一般式（C）

General formula (C)

一般式（D）

General formula (D)

Hereinafter, Table 7 shows physical property values of the compound represented by the general formula (1). The ¹ H-NMR shift value shown here uses tetramethylsilane as an internal reference material unless otherwise specified.

  Hereinafter, although the typical compound of the compound represented by General Formula (CC) which has bactericidal action is shown in Table 8, this invention is not limited to these.

  In Table 8, Me represents a methyl group, i-Pr represents an isopropyl group, and t-Bu represents a tertiary butyl group.

  Hereinafter, typical compounds of the compound represented by the general formula (DD) having a bactericidal action are shown in Table 9, but the present invention is not limited thereto.

  In Table 9, Me represents a methyl group, i-Pr represents an isopropyl group, and t-Bu represents a tertiary butyl group.

  Table 10 below shows typical compounds represented by formula (AA) having insecticidal action, but the present invention is not limited thereto.

  In Table 10, Me represents a methyl group, Cl represents a chloro group, and Br represents a bromo group.

  The pest control composition of the present invention contains 0.001 to 95% by weight, preferably 0.01 to 80% by weight, of one or more compounds of known insecticides, known acaricides or known fungicides, respectively. .

  In the pest control composition of the present invention, known insecticides and known acaricides that can be combined with the compound represented by the general formula (1) of the present invention include, for example, azinphos-methyl, acephate (acephate), isoxathion, isofenphos, ethion, etrimfos, oxydemeton-methyl, oxydeprofos, quinalphos, chlorpyrifos , Chlorpyrifos-methyl, chlorfenvinphos, cyanophos, dioxabenzofos, dichlorvos, disulfoton, dimethylvinphos, dimethoate ), Sulprofos, diazinon, thiometon, Tetrachlorvinphos, temephos, tebupirimfos, terbufos, nared, vamidion, pyraclofos, pyridaphenthion, pyrimiphosmethyl, imi Fenitrothion, fenthion, phenthate, flupyrazofos, prothiofos, propaphos, propenofos, profenofos, phoxim, phosalone, phosmet, Formothion, phorate, malathion, mecarbam, mesulfenfos, metamidophos, methidathion, parathions, methyl parathion-methyl, monocrotophos ( monocrotophos), trichlor Trichlorfon, O-ethyl O-4-nitrophenyl phenylphosphothioate (EPN), isazofos, isamifos, cadusafos, diamidafos, diclofenthion, dichfenthion organophosphorus insecticides such as fenamiphos, fosthiazate, fosthietan, phosphocarb, O-4-dimethylsulfenylphenyl O, O-diethylphosphothiothioate (DSP), ethoprophos (ethoprophos), etc. Aldicarb, isoprocarb, ethiofencarb, carbaryl, carbosulfan, xylylcarb, Thiodicarb, pirimicarb, fenobucarb, furothiocarb, propoxur, bendiocarb, benfuracarb, methomyl, metolcarb, 3, 5 Carbamate insecticides such as xylyl methylcarbamate (XMC), carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate, empentrin (empenthrin) ), Cycloprothrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin, cypermethrin ), Alphasipe Metrin (alpha-cypermethrin), zeta-cypermethrin (zeta-cypermethrin), silafluofen (silafluofen), tetramethrin (tetramethrin), tefluthrin (deltamethrin), tralomethrin (bilothrin), bifenthrin (phenfenrin) ), Fenvalerate, fenpropathrin, furamethrin, prallethrin, flucythrinate, fluvalinate, flubrocythrinate, permethrin ), Synthetic pyrethroid insecticides such as resmethrin, etofenprox, and various isomers thereof, cartap, thiocyclam, neristoxin insecticides such as benzultap, Acetamiprid, imida Neonicotinoid insecticides such as loprid (imidacloprid), clothianidin, dinotefuran, thiacloprid, thiamethoxam, nitenpyram, chlorfluazuron, diflubenzuron (diflubenzuron) Teflubenzuron, triflumuron, novaluron, noviflumurur, bistrifluron, fluazuron, flucycloxuron, flufenoxuron, hexafluron Hexaflumuron, lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyfenozide, diofenolan, diofenolan, fenromide, proxyropy Insect growth regulators such as buprofezin, metoprene, hydroprene, kinoprene, triazamate, endosulfan, chlorfenson, chlorobenzilate , Organochlorine insecticides such as dicofol, bromopropylate, phenylpyrazole insecticides such as acetoprole, fipronil, etiprole, pyrethrin (pyrethrins), rotenone ( rotenone, nicotine sulfate, abamectin, bacillus thuringiensis (BT), insecticidal natural products such as spinosad, acequinocyl, amidoflumet, amitraz , Etoxazole, chinomethionat, clofentezin ( clofentezine, fenbutatin oxide, dienochlor, cyhexatin, spirodiclofen, spiromesifen, tetradifon, tebufenpyrad, binapacryl, binapacryl, binapacryl (bifenazate), pyridaben, pyrimidifen, fenazaquin, fenothiocarb, fenpyroximate, fluacrypyrim, fluaziry, fluazinam, flufenzine, hexitix (propargite), benzomate, polynactins, milbemectin, lufenuron, mecarbam, methiocarb, mevinphos, halfenprox (half) enprox), azadirachtin, diafenthiuron, indoxacarb, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate oleate), chlorfenapyl, tolfenpyrad, pymetrozine, phenoxycarb, hydramethylnon, hydroxy propyl starch, pyridalyl, flufenerim, Flubendiamide, flonicamid, metaflumizone, lepimectin, tripyrosicyanurate (TPIC), levamisol hydrochloride, morantel tartrate, dazomet, dazomet, sodium (metam-sodium), a compound represented by the general formula (AA), a compound (BB) and the like.

  Examples of known fungicides that can be combined with the compound represented by the general formula (1) in the pest control composition of the present invention include triadimefon, hexaconazole, and propiconazole. , Ipconazole, prochloraz, triflumizole, tebconazole, epoxiconazole, difenoconazole, flusilazole, triadimenol, cyproconazole (cyproconazole), metconazole, fluquinconazole, bitertanol, tetraconazole, triticonazole, flutriafol, penconazole, diniconazole ), Fenbuconazole ( fenbuconazole), bromuconazole, imibenconazole, simeconazole, microbutanil, hymexazol, imazalil, furametpyr, diflumamide (difluamide) ), Oxpoconazole, oxpoconazole-fumarate, pefurazoate, prothioconazole and other azole fungicides, pyrifenox, fenarimol ( Pyrimidine fungicides such as fenarimol, nuarimol, bupirimate, anilinopyrimidine fungicides such as mepanipyrim, cyprodinil, pyrimethanil, metalaxyl, oxadinil ), Acyl such as benalaxyl Lanine fungicides, thiophanate, thiophanate-methyl, benomyl, carbendazim, carbendazim, fuberidazole, thiabendazole and other benzimidazole fungicides, mancozeb, Dithiocarbamate fungicides such as propineb, zineb, metiram, maneb, ziram, thiram, organochlorine fungicides such as chlorothalonil, ethaboxam (ethaboxam), carboxamide fungicides such as oxycarboxin, carboxyxin, flutolanil, silthiofam, mepronil, dimethomorph, fenpropidin, Fenpropimorph, spiroxamine, tridemol morpholine fungicides such as (tridemorph), dodemorph, flumorph, azoxystrobin, kresoxim-methyl, metinominostrobin, orysastrobin, oryastros Stravirlin fungicides such as robin (fluoxastrobin), trifloxystrobin, dimoxystrobin, pyraclostrobin, picoxystrobin, iprodione, procymidone ), Vinclozolin, dicarboximide fungicides such as clozolinate, flusulfamide, dazomet, methyl isothiocyanate, chloropicrin, methasulfocarb, Hydroxyisoxazole (hydr soil fungicides such as oxyisoxazole), hydroxyisoxazole-potassium, echlomezole, 1,3-Dichloropropene (DD), metam-sodium, basic copper chloride ), Basic copper sulfate, copper nonylphenol sulfonate, copper-oxinate, dodecylbenzenesulfonate bisethylenediamine copper complex (II) (DBEDC), anhydrous copper sulfate (copper) Copper fungicides such as sulfate anhydride, copper sulfate, cupric hydroxide, inorganic sulfur, wettable sulfur, lime sulfur mixture polysulfide), zinc sulfate, fentin, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hypochlorite (sodiu m hypochlorote), inorganic fungicides such as metallic silver, edifenphos, tolclofos-methyl, fosetyl, iprobenfos, dinocap, pyrazophos, etc. Organic phosphorus fungicides, carpropamid, fthalide, tricyclazole, pyroquilon, diclocymet, phenoxanil and other melanin biosynthesis inhibitors fungicides, kasugamycin , Validamycin A, polyoxins, polyoxins, blastcidin-S, oxytetracycline, mildiomycin, streptomycin and other antibiotic fungicides, rapeseed oil ( natural product fungicides such as rape seed oil and machine oil, (benthiavalicarb-isopropyl), iprovalicarb, propamocarb, prophetocarb, carbamate fungicides such as dietofencarb, fluorimide, fludioxonil, pyrrole fungicides such as fenpiclonil, quinoxyphene Quinoxyfen), quinolinic fungicides such as oxolinic acid, phthalimido phthalonitrile fungicides such as chlorothalonil, captan, folpet, probenazole, acibenzoral Smethyl ( Plant activators that induce plant disease resistance such as acibenzolar-S-methyl and tiadinil, cyflufenamid, fenhexamid, diflumetorim, metrafenone, picobenzamide (picobenzamide) ), Proquinazid, famoxadone, cyazofamid, fenamidone, zoxamide, boscalid, cymoxanil, dithianon, fluanidani, fluazinam d ), Triforine, isoprothiolane, ferimzone, diclomezine, tecloftalam, pencycuron, quinomethionate, iminooctadine-triacetate, iminooctadine-triacetate Salt (iminoctadine-albesilate), Ammoam, polycarbamate, thiadiazin, chloroneb, nickel dimethyldithiocarbamate, guazatine, dodecylguanidine-acetquinto, zenezene ), Trilf Tolylfluanid, anilazine, nitrothal-isopropyl, fenitropan, dimethirimol, benthiazole, harpin protein, flumetover, mandipropa Examples thereof include a mandipropamide, a penthiopyrad, a compound represented by the general formula (CC), a compound represented by the general formula (DD), and the like. Some of the compounds listed above can take stereoisomers, but these isomers are also included in the present invention.

The pest control composition of the present invention is suitable for controlling various agricultural and forestry, horticulture, stored grain pests, sanitary pests, nematodes and the like that harm rice plants, fruit trees, vegetables, other crops, and florets. As LEPIDOPTERA, bats (Endoclyta excrescens), yellow bats (Endoclyta sinensis), white bats (Palpifer sexnotata), rose clam (Acleris comariana), apple wolfberry moth (Adoxophyes orana fasciata), chanocok oxophyllum spe. , Apple chipworm (Archips breviplicanus), green chipworm (Archips fuscocupreanus), black chipworm (Archips xylosteanus), rush moth (Bactra furfurana), hosobahairofurakiana (Cnephasia cinereipalpana), chestnut aestuosa), apple cinchoi (Grapholita inopinata), pear cinchoni (Grapholita molesta), chi Japanese cypress (Homona magnanima), Japanese apple oyster (Hoshinoa adumbratana), Japanese bean moth (Leguminivora glycinivorella), Japanese azuki moth (Matsumuraeses azukivora), Japanese soybean moth (Matsumuraeses falcana), Japanese cypress (Matsumuraeses falcana) Clams (Spilonota lechriaspis), Apples (Spilonota ocellana), Grape commune (Eupoecillia ambiguella), Crested crested oyster (Phalonidia mesotypa), Artemisia clandestina (Phtheochroides clandestina), Grape podium mona ), Minoga (Bambalina sp.), Mioga (Eumeta japonica), Chaminoga (Eumeta minuscula), Kokuga (Nemapogon granellus), Iga (Tinea translucens), Nashichibiga (Bucculatrix pyrivorella), Pseudomona (Lyonetia clerknetia) prunifoliella) ptilia soyella, Caloptilia theivora, appleopter moth (Caloptilia zachrysa), oyster moth (Cuphodes diospyrosella), golden moth (Phyllonorycter ringoniella), pear moth (Pule), citrus moth Acrolepiopsis sapporensis), Prunella xylostella, Pyella xylostella, Argyresthia conjugella, Paranthrene regalis, Synanthedon hector, Trismas brilliant , Cotton beetle (Pectinophora gossypiella), potato moth (Phthorimaea operculella), peach sinker moth (Carposina niponensis), apple larva (Illiberis pruni), black moth (Latoia sinica), moth flavscens (Naseu), oid eus alis, Parasas consocia, Scopelodes contracus, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diaphania inivica, Diaphania inc ), Ephestia elutella, Ephestia kuehniella, Etiella zinckenella, Euzophera batangensis, Glyphodes pyloells aunida ), Rice bran (Marasmia exigua), legume (Maruca testulalis), cotton moth (Notarcha derogata), green moth (Ostrinia furnacalis), azuki bean moth (Ostrinia scapulalis), puffer moth (Ostriella zagulia) ), Noshimema Lamiga (Plodia interpunctella), Sankameiga (Scirpophaga incertulas), Ipomosei parsley (Parnara guttata), Papilio helenus, Papilio machaon hippocrates, Papilio xuthus, Papilio xuthus, Monias butterfly , Lumpides boeticus, Angerona prunaria, Ascotis selenaria, Biston robustum, Cystidia couaggaria, Dendrolima ace testis Odonestis pruni japonensis, Cephonodes hylas, Grape sparrow (Acosmeryx castanea), Black killer whale (Clostera anachoreta), Black-headed killer whale (Clostera anastomosis), Moncler killer whale (Phalera flavescens ero ), Orcaia thyellina, Oryia thyellina, H. (Spilosoma imparilis), Acanthoplusia agnata, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Anomis flava, Anomis grava, Anomis gri Nettle squirrel (Trichoplusia ni), Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Heliothis maritima, Mamestra brassicae, Naranga aenescens, Paralysium separatus (Pseudalet) Spodoptera deprava ta), Spodoptera exigua, Spodoptera litura, Apple trimon (Triaena intermedia), Nashikenmon (Viminia rumicis), Xestia c-nigrum, etc., Hemioptera Marker bug (Megacopta punctatissimum), Spotted bug (Carpocoris purpureipennis), Spotted beetle (Dolycoris baccarum), Giant tortoise (Eurydema pulchrum), Tortoise (Eurydema rugosum), Tiger worm (Eysd) , Eysarcoris parvus, Eysarcoris ventralis, Glaucias subpunctatus, Graphosoma rubrolineus, Longyomorpha mista, Long-tailed beetle , Nezara viridula, Ichimon Zizmokumushi (Piezodorus hybneri), Chabanae stink bug (Plautia stali), Scotinophara lurida, Siwainokamemushi (Starioides iwasakii), Greater sword beetle (Acanthocoris sordidus), Orokumoshimushii punctiger), Scarlet beetle (Cletus trigonus), Paramecium beetle (Molipteryx fulginosa), Beetle beetle (Leptocorisa acuta), Beetle beetle (Leptocorisa chinensis), Thai beetle beetle (Leptocorisa or helicopter) clavatus), red beetle bug (Aeschynteles maculatus), red beetle beetle bug (Liorhyssus hyalinus), edible beetle bug (Cavelerius saccharivorus), horned beetle bug (Macropes obnubilus), flat beetle Long-tailed bug (Paromius exguus) ), Copter, Togo hemipterus, Dysdercus cingulatus, Dysdercus poecilus, Galleatus spinifrons, Metasalis populi, Stepitis, Stephynci Stephanitis pyrioides, Uhlerites debile, Uhlerites latius, Adelphocoris lineolatus, Adelphocoris triannulatus, Apolygus luco rum spinolai, red-faced turtle (Creontiades pallidifer), tobacco turtle (Cyrtopeltis tennuis), giant black-faced turtle (Ectometopterus micantulus), black-faced turtle (Halticiellus insularis), apple black-legged turtle (Heterocordylus disp i), Madarakas turtle (Lygus saundersi), sugar beet turtles (Orthotylus flavosparsus), wheat turtles (Stenodema calcaratum), stag beetle turtles (Stenotus binotatus), Akasikakasika turtle (Stenotus rubrovittatus), Usumonidori mussel (yl) Homooptera, such as Trigonotylus coelestialium, Agrophasaltria nigrofuscata, Aphrophora costalis, Aphrophora flavipes, Aphrophora vitis, Aphrophora vitis, , Hosoawafuki (Philaenus spumarius), Bluefin leafhopper (Bothrogonia japonica), Leafhopper (Cicadella viridis), Whiteleaf leafhopper (Cofana spectra), Aguriahana quercus, Alpineoidia ali ferruginea), lid Arboridia apicalis, Edwardiana flavescens, Roseana leaf (Edwardsiana rosae), Empoasca abietis, Empoasca onukii, submarine Leafhopper (Zyginella citri), Leafhopper leafhopper (Macrosteles fascifrons), Leafhopper leafhopper (Nephotettix cincticeps), Leafhopper leafhopper (Nephotettix nigropictus), Taiwantsuba leafhopper (Nephotettix virescens), Apple leaflet Sorhoanus tritici, Speusotettix subfusculus, Japanese green planthopper (Laodelphax striatellus), Japanese green planthopper (Nilaparvata lugens), Saturus green planthopper (Numata muiri), Corn planter (Peregrinus maiden) aricida), white-spotted leafhopper (Sogatella furcifera), green-spotted leafworm (Sogatella panicicola), stag beetle (Anomoneura mori), white-spotted lice (Calophya nigridorsalis), citrus white-headed lice (Diaphorina citri), white-headed lice Psylla alni, Pepylla jamatonica, Psylla mali, Psylla malivorella, Psylla pyrisuga, Psylla tobirae, ae phoro camphor, Trioza quercicola), honey beetle (Aleurocanthus spiniferus), grape lice (Aleurolobus taonabae), tobacco white lice (Bemisia tabaci), citrus white lice (Dialeurodes citri), on-site white lice (Trialeurodes vaporarioemi) (V iteus vitifolii, Aphidounguis mali, Eriosoma lanigerum, Geoica lucifuga, Acyrthosiphon pisum, Aphis crtricola, Aphis citricola, Aphis citricola Aphids (Aphis farinose yanagicola), cotton aphids (Aphis gossypii), potato aphids (Aulacorthum solani), wheat aphids (Brachycaudus helichrysi), radish aphids (Brevicoryne brassicae),
Tulip aphid (Dysaphis tulipae), Aedes aphid (Euceraphis punctipennis), peach beetle (Hyalopterus pruni), black-headed aphid (Lipaphis erysimi), yellow-spotted aphid (san) Broad beetle aphids (Megoura crassicauda), pear beetle (Melanaphis siphonella), apple aphid (Myzus malisuctus), aphid aphid (Myzus mumecola), peach aphid (Myzus persicae), negia aphid era (Ovatus malicolens), Rhopalosiphum nymphaeae, Rhopalosiphum padi, Rhapalosiphum rufiabdominalis, Sappaphis piri, Nasiphi piri (Schiza cola), wheat beetle aphid (Sitobion akebiae), barb beetle aphid (Sitobion ibarae), rice aphid (Toxoptera aurantii), citrus aphid (Toxoptera citricidus), peach aphid (Tuberocephalus momonro) , Schizaphis graminum, Drosicha corpulenta, Icerya purchasi, Cristicoccus matsumotoi, Crisicoccus pine, ocist Scale scale (Planococcus citri), Fuji scale meal scale (Planococcus kraunhiae), citrus scale scale (Pseudococcus citriculus), scallop scale (Pseudococcus comstocki), horn beetle (Ceroplastes ceriferus), ruby plast Coccus discrepans, Coccus hesperidum, Coccus pseudomagnoliarum, Ericerus pela, Lecanium corni, Lecanium peri Pulvinaria aurantii), Pulvinaria citricola, Pulvinaria kuwacola, olive scale insect (Saissetia oleae), citrus scale insect (Andaspis kashicola), red spotted scale (Aonidiella aurantii, citrus scale) Aspidiotus destructor, Aspidiotus hederae, Red-footed scale (Chrysomphalus ficus), Nymphalidae (Comstockaspis perniciosa), Black-headed scale (Duplaspidi) otus claviger), citrus scale insect (Lepidosaphes beckii), apple pod scale bug (Lepidosaphes ulmi), pear scale insect (Lopholeucaspis japonica), puffer bug (Parlatoreopsis pyri), camellia camellia aellia (Parlia) Scale insects (Parlatoria theae), ground beetle scales (Parlatoria ziziphi), bark beetle scales (Pinnaspis aspidistrae), citrus scale scale (Pseudaonidia duplex), chano scale scale (Pseudaonidia paeoniae), stag beetle (Pseuda) Pseudaulacaspis prunicola), Unaspis yanonensis, etc., COLEOPTERA (Eucetonia roelofsi), Heptophylla picea, Japanese beetle (Melolontha japonica), Scarabae beetle (Mimela splendens), Core red crested beetle (Oxycetonia jucunda), Japanese beetle (Popillia japonica), Japanese beetle Angenus thunus ), Tobacco beetle (Lasioderma serricorne), Lyctus brunneus, Carpophilus dimidiatus, Carpophilus hemipterus, Epilachna vigintioctomapilto , Common beetle (Epilachna varivestis), red beetle (Alphitobius laevigatus), red beetle (Neatus picipes), red beetle (Palorus ratzeburgii), red beetle (Palorus subdepressus), t Tribolium castaneum, Tribolium confusum, Epicauta gorhami, Aeolesthes chrysothrix, Anoplophora malasiaca, ham P , Grape beetle (Xylotrechus pyrrhoderus), green beetle (Xystrocera globosa), bean weevil (Acanthoscelides obtectus), beetle weevil (Callosobruchus chinensis), jujube beetle (Callosobruchus feculais), ham ham ), Beetle leaf beetle (Cassida nebulosa), beetle beetle (Chaetocnema concinna), beetle beetle (Colasposoma dauricum), beetle beetle beetle (Crioceris quatuordecimpunctata), beetle beetle (Donacia provosti), ruri beetle (ina) nea), Luperomorpha tunebrosa, Medythia nigrobilineata, Oulema oryzae, Pagria signata, radish beetle (Phaedon brassicae), Phyllotta sham Leptinotarsa decemlineata), corn root worms (Diabrotica sp.), Eel weevil (Involvulus cupreus), peach weevil (Rhynchites heros), aphid weevil (Cylas formicarius), apple weevil (Anthonomus pomorum) Ceuthorhynchidius albosuturalis), Curculio sikkimensis, weevil (Echinocnemus squameus), weevil (Euscepes postfasciatus), horned weevil (Hypera nigrirostris), alfalfa weevil Listroderes costirostris, Apple weevil (Phyllobius armatus), Chibi beetle weevil (Sitona japonicus), Cotton weevil (Anthonomus grandis), Scotch weevil (Sitophilus oryzae), Sweeophilus estamas tus Tomicus piniperda, THYSANOPTERA, etc. lilivora), Croton thrips (Heliothrips haemorrhoidalis), Cosmos thrips (Microcephalothrips abdominalis), Soybean thrips (Mycterothrips glycines), Thrips thrips (Pseudodendrothrips mori), Chano thalis rs Selenothrips rubrocinctus, Thrips alliorum, Thrips coloratus, Thrips flavus, Thrips flavus, Thrips flavus, Thrips flavus, Thrips flavus ), Thrips palmi, Franklinella occidentalis, Soybean thrips (Thrips setosus), Gladiolus thrips (Thrips simplex), Thrips tabacioth, Thrips tabacioth Hump thrips chinensis, Haplothrips kurdjumovi, Thrips thrips (Haplothrips niger), Leeuwenia pasanii, Lithrips Da thrips (L Itotetothrips pasaniae), Ponticulothrips diospyrosi, etc., ORTHOPTERA ), Japanese clover (Homorocoryphus jezoensis), Japanese crested rice (Homorocoryphus lineosus), Kera (Gryllotalpa sp.), Cox lion (Oxya hyla intricata), Cox yezoensis, Tocusama migratoria (Locusta migratoria), etc.
The diptera (DIPTERA) includes: Tipula aino, Bradysia agrestis, Soybean fly (Asphondylia sp.), Fly fly (Dacus cucurbitae), Citrus fly (Dacus dorsalis) D , Rhacochlaena japonica, Hydrellia griseola, Hydrellia sasakii, Drosophila suzukii, Drosophila suzukii, Glofly (Chromatomyia horticola), eggplant leaf fly (Liriomyza bryoniae), green leaf fly (Liriomyza chinensis), bean leaf fly (Liriomyza trifolii), tomato leaf fly (Liriomyza sativae), agrowing leaflet (Liriomyza elia) platura), Tenza Papimya cunicularia, Phormia regina, Musca domestica, Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Cutus pi, ERA ), Japanese bee wasp (Athalia japonica), bee (Athalia rosae ruficornis), apple bee (Arge mali), horn bee (Arge pagana), bee (Dryocosmus kuriphilus), black ant (Formica japonica) NA, etc. (ARI) , Mite mites (Polyphagotarsonemus latus), cyclamen mites (Steneotarsonemus pallidus), sand mites (Tarsonemus waitei), lice mites (Pyemotes ventricosus), wheat mites (Penthaleus major), grape mites (Brevipalpus palisi, mites) (Do lichotetranychus floridanus), oyster spider mite (Tenuipalpus zhizhilashviliae), southern spider spider mite (Brevipalpus phoenicis), nicknamed spider mite (Tuckerella pavoniformis), clover spider mite (Bryobia praetiosa), fake spider spider mite (Bryobia rubri spider spider mite (Bryobia rubri) ), Chestnut mite (Eotetranychus pruni), white spider mite (Eotetranychus sexmanaculatus), Smith spider mite (Eotetranychus smithi), walnut spider mite (Eotetranychus uncatus), cedar spider mite (Oligonychus hondoensis), tick Panonychus citri), apple spider mite (Panonychus ulmi), black spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus kanzawai), spider spider mite (Tetranychus urticae), sweet spider mite (Tetranychus viennensis), mite Aca a theae), tulip rustic mites (Aceria tulipae), citrus mites (Aculops pelekassi), peach mites (Aculus fockeui), apple rustic mites (Aculus schlechtendali), green rusted mites (Calacarus carinatus), grape rust mites (Calepitrimerus vitis), pith rim Scarlet mite (Eriophyes chibaensis), Acarus siro (Acarus siro), Mud mite (Aleuroglyphus ovatus), Robin tick (Rhizoglyphus robini), Scarlet mite (Tyrophagus putrescentiae), Mite (Tyrophagus putrescentot) ), Leptotrombidium pallidum, etc.
TYLENCHIDA includes bentgrass nematode (Anguina agrostis), wheat nematode (Anguina tritici), imogusaresenchu (Ditylenchus destructor), namishkusenchu (Tylenchorhynchus claytoni), martini Tylenchorhynchus sp.), Hirschmanniella imamuri, Hirschmanniella oryzae, Pratylenchus coffeae, Pratylenchus convallariae, enchall Chanegusa nematode (Pratylenchus loosi), wheat nematode nematode (Pratylenchus neglectus), northern nematode nematode (Pratylenchus penetrans), negresa nematode (Pratylenchus sp.), Namila nematode (Helicotylenchus dihystera), cha Helicotylenchus erythrinae, Helicotylenchus sp., Hoplolaimus sp., Rotylenchulus reniformis, Brachyur nematode (Scutellonema brachyurum), B Nematode (Cactodera cacti), Nematocyst nematode (Cryphodera sp.), Potato cyst nematode (Globodera rostochiensis), Nematocyst nematode (Heterodera elachista), Soy bean nematode (Heterodera glycines), Clover cyst nematode (Heterodera nematode) Meloidogyne arenaria, Meloidogyne camelliae, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne sp.), Tylenchulus semipenetrans, Aphelenchus avenae, and the like, DORYLAIMIDA, Longidorus martini, Nagaido nematode (Longidorus sp.), USA Hippo nematode (Xiphinema americanum), Papilio nematode (Xiphinema sp.), Yumihari nematode (Trichodorus sp.), Etc. ), Etc. ), Etc., as flea eyes (SIPHONAPTERA), the dog flea (Ctenocephalides cani) s), lice (ANOPLURA), head lice (Pediculus humanus humanus), etc., arthropod labrum (CHILOPODA), geji (Thereuronema tuberculata), etc., arthropod bipod (DIPLOPODA), Examples of molluscs (MOLLUSCA) such as Oxidus gracilis include slugs (Incilaria bilineata).

  Examples of plant diseases that can be controlled by the pest control composition of the present invention include rice blast (Pyricularia oryzae), blight (Rhizoctonia solani), sesame leaf blight (Cochliobolus miyabeanus), and idiot seedling (Gibberella fujikuroi). ); Wheat powdery mildew (Erysiphe graminis f.sp.hordei; f.sp.tritici), rust (Puccinia striiformis; P. graminis; P.recondita; P.hordei), leafy disease (Pyrenophora graminea) , Pyrenophora teres, Fusarium calmorum; F.anenaceum; F.graminearum; Microdochium nivale, Snow rot (Typhula sp .; Micronectriella nivale), Bare scab (Ustilago tritici; U.nuda) ), Rot rot (Tilletia caries), eye spot (Pseudocercosporella herpotrichoides), strain rot (Rhizoctonia cerealis), cloud disease (Rhynchosporium secalis), leaf blight (Septoria tritici), leaf blight (Leptosphaeria nodorum); , Cucumber, tomato, strawberry, grape, potato, soybean, cabbage, eggplant, lettuce Botrytis cinerea; rice, cabbage, komatsuna, tomato, eggplant and other seedling blight (Rhizoctonia solani); grape downy mildew (Plasmopora viticola), rust (Phakopsora ampelopsidis), powdery mildew ( Uncinula necator), black scab (Elsinoe ampelina), late rot (Glomerella cingulata); apple powdery mildew (Podosphaera leucotricha), black scab (Venturia inaequalis), spotted leaf (Alternaria mali), red scab (Gymnosporangium yamada) ), Moniria disease (Sclerotinia mali), rot disease (Valsa mali); pear black spot disease (Alternaria kikuchiana), black star disease (Venturia nashicola), red star disease (Gymnosporangium haraeanum), ring rot (Physalospora piricola) Sclerotinia cinerea, black spot disease (Cladosporium carpophilum), homopsis spoilage disease (Phomopsis sp.); Oyster anthracnose (Gloeosporium kaki), leaf fall (Cercospora kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia) ); Cucumber downy mildew (Pseudoperonospora cube) nsis), brown spot (Corynospora melonis), wilt (Rizoctonia solani), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum lagenarium), vine blight (Mycosphaerella melonis); Diseases (Alternaria solani), leaf mold disease (Cladosporium fulvam), plague (Phytophthora infestans); eggplant powdery mildew (Erysiphe cichoracorum), subtilis disease (Mycovellosiella nattrassii); cruciferous vegetable black spot disease (Alternaria japonica) White spot disease (Cercosporella brassicae), clubroot disease (Plasmodiophora brassicae), root rot disease (Phoma lingam); green onion rust (Puccinia allii), black spot (Alternaria porri); spinach, green onion etc. ); Soybean purpura (Cercospora kikukuchii), black scab (Elsinoe glycinnes), black spot (Diaporthe phaseololum); common bean anthracnose (Colletotrichum lindemuthianum); groundnut black rot (Mycosphaerellapersonatum), brown spot (Cercospora) arachidicola); Pea Udo Mildew (Erysiphe pisi), downy mildew (Peronospora pisi); potato summer plague (Alternaria solani), black rot (Rhizoctonia solani), plague (Phytophthora infestans); broad bean downy mildew (Peronospora viciae), plague (Phytophthora nicotianae); Chamodium rot (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthracnose (Colletotrichum theae-sinensis); tobacco red scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), charcoal Colletotrichum tabacum, platy (Phytophthora parasitica); brown spot of sugar beet (Cercospora beticola); black spot of rose (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases (Septoria chrysanthemi-indici), white rust (Puccinia horiana); strawberry powdery mildew (Sphaerotheca humuli), plague (Phytophthora nicotianae); green beans, cucumber, tomato, strawberry, potato, soybean, cabbage, eggplant, lettuce, etc. Fungus Disease (Sclerotinia sclerotiorum); citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcettii); carrot black leaf blight (Alternaria dauci); turf ground patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa) ), Large patch disease (Rhizoctonia solani) and the like, but are not limited thereto.

  The content of the compound effective for pest control in the pest control composition of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, and 10 to 90% by weight for wettable powders. In the case of granules, it is 0.1 to 20% by weight and in the case of flowable preparations it is 10 to 90% by weight. On the other hand, the amount of carrier in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, 80 to 99% by weight for granules, and flowable preparations Is 10 to 90% by weight. The amount of the auxiliary agent is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and In the flowable preparation, it is 0.1 to 20% by weight.

  The pest control composition of the present invention is used for controlling pests as it is, or appropriately diluted with water or the like, or suspended in an amount effective for pest control in order to control various pests. Apply to the habitat. The amount used varies depending on various factors such as purpose, target pest, crop growth, pest generation tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. The active ingredient per area may be appropriately selected from the range of 0.1 g to 1000 g, and preferably in the range of 1 g to 500 g.

  As a method for controlling the pest by applying the pest control composition of the present invention to the pest or the habitat of the pest, for example, spraying on the foliage for pests generated in fruit trees, cereals, vegetables, etc. In addition, soil treatment, soil application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dressing, paddy rice seedling box treatment, water surface treatment, etc., are absorbed into the soil and absorbed from the roots. Can also be used. In addition, it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection. Further, for example, in addition to spraying on stored grain pests, house pests, sanitary pests, forest pests, etc., they can also be used for application to house building materials, smoke, baits and the like.

  By applying the pest control composition of the present invention to the harvest of agricultural plants, it is possible to control pests generated during storage of the crop. That is, an amount effective for pest control in the form of the pest control composition of the present invention as it is, or appropriately diluted or suspended with water or the like is used in an agricultural plant crop or an agricultural plant crop. A post-harvest treatment such as spraying, smearing, coating, dipping, powder coating, fumigation / smoke, or pressure injection may be performed on the storage place.

  Agricultural plant crops include, for example, rice, barley, wheat, corn, rye, oats, peas, green beans, cowpea, sultani beans, saltapia beans, butter beans, peggia beans, white beans, lima beans, broad beans, soybeans, Azuki beans, apricots, plums, sweet potatoes, plums, nectarines, peaches, oranges, grapefruits, natsumikan, mandarin oranges, sudachi, daidai, kabosu, lime, lemon, loquat, quince, apples, pears, pears, avocados, kiwifruits, guava , Date Palm, Pineapple, Passion Fruit, Banana, Papaya, Mango, Strawberry, Cranberry, Huckleberry, Blackberry, Blueberry, Oyster, Watermelon, Grape, McWauli, Melon, Turnip, Cauliflower, Cabbage, Daikon, Chinese Cabbage, Komatsuna, Creso , Kale, horseradish, radish, broccoli, sweet potato, konjac potato, taro, potato, pumpkin, cucumber, shirori, artichoke, endive, burdock, salsify, chicory, lettuce, shiitake mushroom, celery, carrot, parsnip, parsley, tomato , Eggplant, bell pepper, asparagus, onion, garlic, leek, scallion, green beans, okra, sugarcane, ginger, sugar beet, spinach, immature green beans, immature peas, oil seeds , Cotton seeds, etc.), nuts (almond, ginnan, chestnut, walnut, pecan etc.), cacao beans, coffee beans, tea, hops, etc., but the present invention is not limited to these.

  By applying the pest control composition of the present invention to plant seeds, pests generated during seed storage can be controlled. That is, the pest control composition of the present invention is sprayed and applied to a plant seed or a plant seed storage location in an amount effective for pest control as it is, or appropriately diluted or suspended with water or the like. Treatments such as spraying, coating, dipping, dressing, smoke or fumigation may be performed.

  By applying the pest control composition of the present invention to plant seeds, it is possible to prevent damage caused by pests generated in the plant after sowing. That is, the pest control composition of the present invention is sprayed, smeared, soaked or dressed in an amount effective for controlling pests as it is, or appropriately diluted with water or the like, or suspended. It is only necessary to contact a plant seed with a compound that is effective in controlling pests.

Plant seeds refer to those that store nutrients for germination of young plants and are used for agricultural reproduction. For example, seeds such as corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, sweet pepper, rape, sweet potato , Seed seeds such as konjac, edible lily, bulbs such as tulips and seed balls such as raccoon. These plant seeds may be transformed. A transformed plant refers to a plant that has been created by artificially manipulating genes and the like and does not exist in nature. For example, soybean, corn, cotton, etc. imparted with herbicide resistance, rice, tobacco, etc. adapted to cold regions, corn, cotton, potato, etc., imparted with the ability to produce insecticides.
The pest control composition of the present invention is generally used after being formulated in a convenient form for use according to a conventional formulation method for agricultural and horticultural drugs. That is, these are mixed in a suitable inert carrier, or if necessary, together with an auxiliary agent in a suitable ratio and dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and an appropriate dosage form, for example, , Suspensions, emulsions, solutions, wettable powders, granules, powders, tablets and the like.

  The inert carrier may be either solid or liquid, and examples of materials that can be a solid inert carrier include soy flour, cereal flour, wood flour, bark flour, saw flour, tobacco stem flour, walnut Shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as pulverized synthetic resin, clays (eg kaolin, bentonite, acidic clay), talc (eg talc, pyrophyllide), silicas (For example, diatomaceous earth, siliceous sand, mica, white carbon (some synthetic high-dispersed silicic acid called hydrous fine silicon, hydrous silicic acid, and some products contain calcium silicate as a main component), activated carbon, sulfur powder, pumice, calcined diatomaceous earth , Brick minerals, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, ammonium sulfate, phosphorous, ammonium nitrate, urea, salt, etc. Manabu fertilizers, etc. can be mentioned compost, which are used alone or in the form of a mixture of two or more.

  As materials that can be used as liquid inert carriers, in addition to those having solvent ability, compounds that are effective in controlling pests can be dispersed with the aid of auxiliary agents without having solvent ability. For example, the following carriers may be used as representative examples, and these may be used alone or in the form of a mixture of two or more, such as water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene). Glycol), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg diethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, Mineral oil), good Group hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, etc.), esters (eg, ethyl acetate, butyl acetate, propion) Ethyl acrylate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (eg dimethylformamide, diethylformamide, dimethylacetamide etc.) and nitriles (eg acetonitrile).

  As the auxiliary agent, typical auxiliary agents exemplified below can be exemplified, and these auxiliary agents are used depending on the purpose, and are used alone or in some cases, in combination with two or more auxiliary agents. In some cases, it is possible to use no adjuvant.

  Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting compounds that are effective in controlling pests, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher grades. Surface activity such as fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher alcohol sulfate Agents can be indicated.

  Further, for the purpose of dispersion stabilization, adhesion and / or binding of compounds effective for pest control, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxy Adjuvants such as methylcellulose, gum arabic, polyvinyl alcohol, pine oil, coconut oil, bentonite, xanthan gum, lignin sulfonate can be used.

  In order to improve the fluidity of solid products, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.

  The pest control composition of the present invention is stable to light, heat, oxidation, etc., but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2,6-di-t-butyl-4-methyl). Stabilizers such as phenol), phenol derivatives such as BHA (butylhydroxyanisole), bisphenol derivatives, arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, phenetidine and acetone condensates, or benzophenone compounds As a result, a more stable composition can be obtained.

  The pest control composition of the present invention can also be mixed with plant protection agents and materials such as herbicides, fertilizers, soil conditioners, plant growth regulators, etc. to make a multipurpose composition with further excellent efficacy.

  The following examples explain typical examples for producing the compound represented by the general formula (1) of the present invention, but are not limited thereto.

[Example 1-1]
Preparation of 4-heptafluoroisopropyl-2- (trifluoromethylthio) aniline

10.0 g of 2- (trifluoromethylthio) aniline, 45.8 g of 2-iodoheptafluoropropane, 10.8 g of hydrosulfite sodium, 5.2 g of sodium hydrogen carbonate, 2.1 g of tetra-n-butylammonium hydrogen sulfate The mixture was added to a mixed solvent of 200 ml of t-butyl methyl ether and 200 ml of water, and stirred vigorously at room temperature for 10 hours. The organic phase was separated and washed with a saturated aqueous sodium hydrogen carbonate solution, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 20: 1) to give 6.5 g (yield 40%) of the title object as an orange oil.
¹ H-NMR (CDCl ₃ , ppm) δ4.80 (2H, broad-s), 6.84 (1H, d, J = 8.3Hz), 7.45 (1H, d, J = 8.3Hz), 7.70 (1H, s ).
Using the same method, the following arinins were produced.
4-Heptafluoroisopropyl-2- (pentafluoroethylthio) aniline
¹ H-NMR (CDCl ₃ , ppm) δ4.79 (2H, broad-s), 6.83 (1H, d, J = 8.8Hz), 7.45 (1H, dd, J = 2.0Hz and 8.8Hz), 7.67 ( 1H, d, J = 2.0Hz).
Orange oil 4-heptafluoroisopropyl-2- (heptafluoro-n-propylthio) aniline
¹ H-NMR (CDCl ₃ , ppm) δ4.78 (2H, broad-s), 6.84 (1H, d, J = 8.8Hz), 7.46 (1H, dd, J = 2.0Hz and 8.8Hz), 7.67 ( 1H, d, J = 2.0Hz).
Yellow oil 4- (heptafluoro-n-propyl) -2- (trifluoromethylthio) aniline
¹ H-NMR (CDCl ₃ , ppm) δ 4.20 (2H, broad), 6.85 (1H, d, J = 8.3Hz), 7.44 (1H, dd, J = 2.0, 8.3Hz), 7.69 (1H, d , J = 2.0Hz).
Yellow oil

[Example 1-2]
Preparation of 2-bromo-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline

To a solution obtained by adding 3.30 g of 4-heptafluoroisopropyl-2- (trifluoromethylthio) aniline to 10 ml of N, N-dimethylformamide, 1.62 g of N-bromosuccinimide dissolved in 5 ml of N, N-dimethylformamide was added. Drop loading was performed. After stirring at room temperature for 2 hours, ethyl acetate and water were added to the reaction solution. The organic phase was separated, washed with 50 ml of water, and dried over anhydrous magnesium sulfate. The solution obtained by filtering off anhydrous magnesium sulfate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 15: 1) to give 2.92 g of the title object product. (Yield 73%) was obtained as a light brown oil.
_{^{1 H-NMR (CDCl 3,}} ppm) δ5.29 (2H, broad-s), 7.68 (1H, s), 7.74 (1H, d, J = 2.0Hz).
Using the same method, the following anilines were produced.
2-Bromo-4-heptafluoroisopropyl-6- (pentafluoroethylthio) aniline

¹ H-NMR (CDCl ₃ , ppm) δ 5.28 (2H, broad-s), 7.65 (1H, s), 7.75 (1H, d, J = 2.0 Hz).
Orange oil 2-bromo-4- (heptafluoro-n-propyl) -6- (trifluoromethylthio) aniline

¹ H-NMR (CDCl ₃ , ppm) δ5.36 (2H, broad-s), 7.67 (1H, s), 7.72 (1H, d, J = 2.0 Hz).
Orange oil
Further, 2-chloro-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline was produced using N-chlorosuccinimide instead of N-bromosuccinimide.

_{^{1 H-NMR (CDCl 3,}} ppm) δ5.23 (2H, broad-s), 7.60 (1H, s), 7.64 (1H, s).
Red oil

[Example 1-3]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-nitrobenzamide

7.47 g of 3-nitrobenzoyl chloride and 7.56 g of 2-bromo-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline were added to 50 ml of pyridine, followed by stirring at 90 ° C. for 10 hours. The reaction solution was poured into ice water, and the pH was adjusted to pH 1 with 2N hydrochloric acid, followed by extraction with ethyl acetate. The residue obtained by distilling off the solvent under reduced pressure was added to a mixed solvent of 30 ml of tetrahydrofuran and 20 ml of water, followed by stirring in an ice-water bath. To this solution, 1.2 g of sodium hydroxide was added and stirred for 1.5 hours in an ice-water bath, and then stirred at room temperature for 20 hours. Ethyl acetate and water were added to the reaction solution, and the organic phase was separated and washed once with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to give 6.85 g of the title object product ( 68% yield) was obtained as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 7.80 (1H, t, J = 7.8Hz), 8.05 (2H, s), 8.16 (1H, s), 8.30-8.34 (1H, m), 8.50-8.53 (1H, m), 8.82 (1H, t, J = 2.0Hz).

[Example 1-4]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-aminobenzamide

To a solution of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-nitrobenzamide 6.85 g and stannous chloride (anhydride) 7.61 g in 50 ml of ethanol, concentrated hydrochloric acid was added. 5 ml was added and stirred at 60 ° C. for 3 hours. After returning to room temperature, the reaction solution was poured into ice water and neutralized with potassium carbonate. Insoluble material was removed by filtration, followed by extraction with ethyl acetate, and the solvent was distilled off under reduced pressure. The precipitated solid was washed with n-hexane to give the title object product (5.13 g, yield 79%) as a white solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ5.40 (2H, broad-s), 6.78-6.81 (1H, m), 7.13-7.21 (3H, m), 7.99 (1H, s), 8.25 ( 1H, d, J = 2.0Hz), 10.64 (1H, s).
The following compounds were prepared using similar methods.
N- (2-Bromo-4-heptafluoroisopropyl-6-pentafluoroethylthio) phenyl 3-aminobenzamide

_{^{1 H-NMR (CDCl 3,}} ppm) δ3.91 (2H, broad-s), 6.91-6.94 (1H, m), 7.25-7.34 (3H, m), 8.01 (2H, s), 8.06 (1H, s).
White solid N- [2-bromo-4-heptafluoroisopropyl-6- (heptafluoro-n-propylthio)] phenyl 3-aminobenzamide

¹ H-NMR (DMSO-d ₆ , ppm) δ5.40 (2H, broad-s), 6.80 (1H, d, J = 7.8Hz), 7.14-7.22 (3H, m), 8.00 (1H, s) , 8.29 (1H, s), 10.67 (1H, s).
White solid N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-aminobenzamide

¹ H-NMR (CDCl ₃ , ppm) δ3.91 (2H, broad-s), 6.91-6.94 (1H, m), 7.26-7.32 (3H, m), 7.84 (1H, d, J = 2.4Hz) , 7.97 (1H, s), 8.09 (1H, s).
White solid

[Example 1-5]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(2-chloropyridin-3-yl) carbonylamino] benzamide (Compound No. 1-158)

N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-aminobenzamide (200 mg) and pyridine (56 mg) were added to tetrahydrofuran (3 ml). To a solution of tetrahydrofuran (1 ml) was dissolved 2-chloronicotinic acid chloride (63 mg). The dripping was carried out at room temperature. After stirring at room temperature for 2 hours, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. The solid was washed once with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, the solvent was distilled off under reduced pressure, and the precipitated solid was washed with n-hexane to give 210 mg (yield 84%) of the title object product as a white solid. Got as.
_{^{1 H-NMR (CDCl 3,}} ppm) δ7.42-7.46 (1H, m), 7.60 (1H, t, J = 7.8Hz), 7.80 (1H, d, J = 7.8Hz), 7.94 (1H, d , J = 7.8Hz), 8.02 (1H, s), 8.03 (1H, s), 8.22-8.28 (2H, m), 8.33 (1H, s), 8.41 (1H, s), 8.55 (1H, dd, J = 2.0Hz and 2.9Hz).

[Example 2-1]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (methylamino) benzamide

5 ml of 98% sulfuric acid was cooled to 0 ° C. to 5 ° C. and stirred, and 1.0 g of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-aminobenzamide was added. After stirring for 10 minutes, 5 ml of 37% formaldehyde aqueous solution was added dropwise, and the temperature was kept between 0 ° C. and 5 ° C., followed by stirring for 3 hours. In the cooled state, the reaction solution was neutralized with 28% aqueous ammonia, and ethyl acetate was added to separate the organic phase. The residue obtained by drying over anhydrous magnesium sulfate and distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to give 0.74 g (yield) of the title product. 72%) was obtained as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ2.91 (3H, s), 4.00 (1H, broad), 6.83-6.86 (1H, m), 7.17-7.24 (2H, m), 7.34 (1H, t, J = 7.8Hz), 7.98-8.01 (2H, m), 8.11 (1H, s).
The following compounds were prepared using similar methods.
N- (2-bromo-4-heptafluoroisopropyl-6-pentafluoroethylthio) phenyl 3- (methylamino) benzamide

¹ H-NMR (CDCl ₃ , ppm) δ2.91 (3H, s), 3.99 (1H, broad), 6.83-6.86 (1H, m), 7.17-7.22 (2H, m), 7.34 (1H, t, J = 7.8Hz), 8.01 (2H, s), 8.08 (1H, s).
White solid N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3- (methylamino) benzamide

¹ H-NMR (CDCl ₃ , ppm) δ2.90 (3H, s), 3.97 (1H, broad), 6.81-6.84 (1H, m), 7.16-7.18 (2H, m), 7.32 (1H, t, J = 7.8Hz), 7.56 (2H, s), 7.85 (1H, d, J = 2.0Hz).
White solid

[Example 2-2]
N- (2-Bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(N ′-(2,6-difluorobenzoyl) -N′-methyl) amino] benzamide (Compound No. 2-151) )Manufacturing of

N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (methylamino) benzamide (170 mg) and pyridine (28 mg) were added to tetrahydrofuran (3 ml) in tetrahydrofuran (3 ml) and 2,6-difluoro dissolved in tetrahydrofuran (1 ml). 52 mg of benzoyl chloride was added dropwise at room temperature. After stirring at room temperature for 2 hours, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. The solid was washed once with 1N hydrochloric acid and a saturated aqueous sodium hydrogen carbonate solution, the solvent was distilled off under reduced pressure, and the precipitated solid was washed with n-hexane to give 148 mg (yield 70%) of the title object product as a white solid. Got as.
¹ H-NMR (CDCl ₃ , ppm) δ3.56 (3H, s), 6.69-6.74 (2H, m), 7.13-7.18 (1H, m), 7.43-7.47 (2H, m), 7.72 (1H, s), 7.77-7.81 (1H, m), 7.91 (1H, s), 8.01 (2H, s).

[Example 3-1]
Production of 3- (benzoylamino) benzoic acid

To 100 ml of water, 5.90 g of sodium hydroxide and 10.0 g of 3-aminobenzoic acid were added and stirred at room temperature, and then 10.3 g of benzoyl chloride was added dropwise so that the internal temperature was maintained at 25-35 ° C. Subsequently, after stirring at room temperature for 6 hours, 25 ml of 6N hydrochloric acid was added dropwise. The precipitated solid was collected by filtration, and the collected filtrate was washed twice with 100 ml of water and dried at 50 ° C. under reduced pressure to obtain 13.9 g (yield 79%) of the title object as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ7.40-7.56 (5H, m), 7.78 (1H, d, J = 7.8Hz), 8.00 (2H, d, J = 8.3Hz), 8.15 (1H, d , J = 7.8Hz), 8.35 (1H, t, J = 2.0Hz), 9.89 (1H, s).

[Example 3-2]
Production of 3- (N-benzoyl-N-methylamino) benzoic acid

To 70 ml of acetone, 5.0 g of 3- (benzoylamino) benzoic acid and 2.95 g of 95% potassium hydroxide (powder) were added and stirred at room temperature, and then 6.4 g of 98% dimethyl sulfate was added dropwise. After completion of the charging, the temperature was raised to reflux conditions, stirred for 4 hours, and cooled to room temperature. The insoluble material was removed by filtration, and the solvent was evaporated under reduced pressure. The residue obtained was charged with 5 ml of 50% aqueous potassium hydroxide solution and 20 ml of ethanol, and stirred at room temperature for 2 hours. To the residue obtained by distilling off the solvent under reduced pressure, 50 ml of ethyl acetate and 50 ml of water were added to separate the aqueous phase, and concentrated hydrochloric acid was added to the aqueous phase to obtain an acidic solution. Subsequently, 100 ml of ethyl acetate was added for extraction, the organic phase was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The precipitated solid was washed with an n-hexane-ethyl acetate mixed solvent (3: 1) and dried under reduced pressure to obtain 3.80 g (yield 72%) of the title object product as a white solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ3.39 (3H, s), 7.21-7.31 (5H, m), 7.35-7.43 (2H, m), 7.70-7.73 (2H, m), 13.07 ( 1H, broad-s).

[Example 3-3]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(N′-benzoyl-N′-methyl) amino] benzamide (Compound No. 2-141)

7.66 g of 3- (N-benzoyl-N-methylamino) benzoic acid, 4.28 g of thionyl chloride and 0.1 ml of N, N-dimethylformamide were added to 40 ml of toluene, followed by stirring at 90 ° C. for 2 hours. The reaction solution was concentrated under reduced pressure to obtain a light brown oil. This oily substance was charged in 30 ml of pyridine in which 4.40 g of 2-bromo-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline was dissolved, and stirred at 90 ° C. for 8 hours. The reaction solution was diluted with ethyl acetate, the organic phase was washed once with 2N hydrochloric acid and saturated aqueous sodium hydrogen carbonate, and concentrated under reduced pressure to give a brown oil. This oily substance was added to a mixed solvent of 40 ml of THF-20 ml of water, then, 4.0 g of sodium hydroxide was charged, and the mixture was stirred at room temperature for 6 hours. Ethyl acetate and water were added to the reaction solution, and the organic phase was separated and washed once with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 9: 1 → 2: 1) to give the title The desired product (4.06 g, yield 60%) was obtained as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ3.55 (3H, s), 7.18-7.22 (2H, m), 7.27-7.35 (4H, m), 7.42 (1H, t, J = 7.8Hz), 7.62 (1H, s), 7.73 (1H, d, J = 7.8Hz), 7.97 (1H, s), 7.99 (1H, s), 8.10 (1H, s).

[Example 4]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfinyl) phenyl 3-[(N′-benzoyl-N′-methyl) amino] benzamide (Compound No. 2-176)

To 12 ml of dichloromethane was added 0.50 g of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(N′-benzoyl-N′-methyl) amino] benzamide and stirred at room temperature. did. Next, 0.26 g of m-chloroperbenzoic acid was charged and stirred at room temperature for 15 hours. A sodium thiosulfate aqueous solution was added to the reaction solution to eliminate the remaining peroxide, and then the organic phase was separated. After washing with water once and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 7: 3). 0.27 g (yield 53%) of the title object product was obtained as a white amorphous substance.
¹ H-NMR (CDCl ₃ , ppm) δ3.57 (3H, s), 7.20-7.33 (5H, m), 7.40 (1H, d, J = 7.8Hz), 7.47 (1H, t, J = 7.8Hz ), 7.57 (1H, s), 7.71 (1H, d, J = 7.8Hz), 8.03-8.05 (1H, m), 8.11 (1H, s), 8.26 (1H, s).

[Example 5]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfonyl) phenyl 3-[(N′-benzoyl-N′-methyl) amino] benzamide (Compound No. 2-191)

To a mixed solvent of dichloromethane 2 ml-acetonitrile 2 ml-water 4 ml, N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(N′-benzoyl-N′-methyl) amino] Benzamide 130 mg and sodium periodate 120 mg were added and stirred at room temperature. Next, 10 mg of ruthenium (III) chloride was added and stirred at room temperature for 5 hours. An aqueous sodium thiosulfate solution was added to the reaction solution to eliminate the remaining peroxide, and then 30 ml of ethyl acetate was charged to separate the organic phase. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 5: 3) to give 82 mg (yield) of the title object. 60%) was obtained as a white amorphous.
¹ H-NMR (CDCl ₃ , ppm) δ3.57 (3H, s), 7.18-7.36 (6H, m), 7.43 (1H, t, J = 7.8Hz), 7.61 (1H, d, J = 2.0Hz ), 7.68 (1H, d, J = 7.8Hz), 8.28 (1H, d, J = 2.0Hz), 8.32 (1H, d, J = 2.0Hz), 8.76 (1H, s).

[Example 6-1]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (benzoylamino) benzamide

A solution prepared by adding 300 mg of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-aminobenzamide prepared in Example 1-4 and 85 mg of pyridine to 3 ml of tetrahydrofuran was dissolved in 1 ml of tetrahydrofuran. 75 mg of benzoyl chloride was added dropwise at room temperature. After stirring at room temperature for 2 hours, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. The product was washed once with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate, the solvent was distilled off under reduced pressure, and the precipitated solid was washed with n-hexane to give 345 mg (yield 97%) of the title product as a white solid. It was.
¹ H-NMR (DMSO-d ₆ , ppm) δ7.53-7.64 (4H, m), 7.81 (1H, d, J = 7.8Hz), 8.00-8.05 (3H, m), 8.11 (1H, d, J = 7.8Hz), 8.31 (1H, d, J = 1.5Hz), 8.41 (1H, s), 10.52 (1H, s), 10.93 (1H, s).

[Example 6-2]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfonyl) phenyl 3- (benzoylamino) benzamide (Compound No. 1-191)

N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (benzoylamino) benzamide 0.34 g, sodium periodate 0.33 g in dichloromethane 2.5 ml-acetonitrile 2.5 ml-water The mixture was added to 5 ml of the mixed solution and stirred at room temperature. Next, 10 mg of ruthenium (III) chloride was added, and the mixture was stirred at room temperature for 7 hours. Sodium bisulfite was added to the reaction solution to decompose the peroxide, and then ethyl acetate was added to separate the organic phase. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to give 0.23 g of the title object product ( Yield 65%) was obtained as a white solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ7.53-7.63 (4H, m), 7.74 (1H, d, J = 7.8Hz), 7.98-8.01 (2H, m), 8.08 (1H, d, J = 8.3Hz), 8.24 (1H, s), 8.38 (1H, t, J = 1.5Hz), 8.81 (1H, s), 10.51 (1H, s), 10.82 (1H, s).

[Example 7]
Preparation of 4-heptafluoroisopropyl-2-methyl-6- (trifluoromethylthio) aniline

2-Bromo-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline (0.92 g), trimethylboroxine (0.13 g) and potassium carbonate (1.44 g) were added to a mixed solvent of toluene (10 ml), ethanol (5 ml) and water (5 ml). Stir in the atmosphere at room temperature. Next, 0.2 g of tetrakis (triphenylphosphine) palladium (0) was charged, and then the temperature was raised to 80 ° C. and stirred for 8 hours. After returning to room temperature, insolubles were filtered off, ethyl acetate and water were added, and the organic phase was separated. The residue obtained by drying over anhydrous magnesium sulfate and distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 20: 1) to give 0.31 g of the title object product ( Yield 40%) was obtained as a pale yellow oil.
_{^{1 H-NMR (CDCl 3,}} ppm) δ2.24 (3H, s), 4.77 (2H, broad-s), 7.34 (1H, s), 7.60 (1H, s).

[Example 8-1]
Preparation of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3-nitrobenzamide

1.17 g of 3-nitrobenzoyl chloride and 1.20 g of (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) aniline were added to 8 ml of pyridine and stirred at 90 ° C. for 6 hours. Ethyl acetate and 1N hydrochloric acid were added to the reaction solution, and the organic phase was separated while the aqueous phase was acidified. The organic phase was then washed twice with a saturated aqueous sodium bicarbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was added to a mixed solution of 10 ml of tetrahydrofuran and 5 ml of water. To this solution, 0.32 g of sodium hydroxide was added and stirred at room temperature for 1 day. Ethyl acetate and water were added to the reaction solution to separate the organic phase, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1). Thus, 1.20 g (yield 72%) of the title object product was obtained as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 7.56 (1H, s), 7.71-7.79 (3H, m), 8.30 (1H, d, J = 7.8Hz), 8.48-8.51 (1H, m), 8.77 ( (1H, t, J = 2.0Hz).

[Example 8-2]
Preparation of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3-aminobenzamide

N- (2-Chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3-nitrobenzamide was used as a starting material, and the title product was prepared according to the conditions described in Example 1-4. White solid. Yield 86%.
_{^{1 H-NMR (CDCl 3,}} ppm) δ3.39 (2H, broad-s), 6.89-6.92 (1H, m), 7.22-7.32 (3H, m), 7.52-7.53 (2H, m), 7.69 ( (1H, d, J = 1.5Hz).

[Example 8-3]
Preparation of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3- (benzoylamino) benzamide (Compound No. 1-241)

N- (2-Chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3-aminobenzamide was used as a starting material, and the title product was prepared according to the conditions described in Example 1-5. White solid. Yield 80%.
¹ H-NMR (CDCl ₃ , ppm) δ7.36-7.43 (3H, m), 7.47-7.53 (2H, m), 7.63-7.65 (2H, m), 7.81-7.87 (3H, m), 8.20 ( 1H, s), 8.28 (1H, s), 8.39 (1H, s).

[Example 9-1]
Production of 2- (2,2,2-trifluoroethoxy) nitrobenzene

A solution obtained by adding 1.70 g of 60% sodium hydride to 20 ml of N, N-dimethylformamide was stirred at 5 ° C., and 4.25 g of 2,2,2-trifluoroethanol dissolved in 5 ml of N, N-dimethylformamide was added. Drop loading was performed. After returning to room temperature and stirring for 1 hour, 5.0 g of 2-fluoronitrobenzene dissolved in 5 ml of N, N-dimethylformamide was added dropwise. Subsequently, after stirring at room temperature for 2 hours, the reaction solution was diluted with ethyl acetate, and then water was charged to separate the organic phase. The residue obtained by drying over anhydrous magnesium sulfate and distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to give 8.14 g of the title object product ( Yield 90%) was obtained as a yellow oil.
¹ H-NMR (CDCl ₃ , ppm) δ4.50 (2H, q, J = 7.8Hz), 7.13-7.22 (2H, m), 7.57-7.62 (1H, m), 7.88 (1H, dd, J = 2.0, 8.3Hz).

[Example 9-2]
Production of 2- (2,2,2-trifluoroethoxy) aniline

2- (2,2,2-trifluoroethoxy) nitrobenzene (3.50 g), 10% palladium-carbon (0.15 g) was added to methanol (25 ml), and the mixture was stirred at room temperature for 3 hours in an atmospheric hydrogen atmosphere. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title object product (2.86 g, yield 95%) as a pale-yellow oil.
¹ H-NMR (CDCl ₃ , ppm) δ3.83 (2H, broad-s), 7.34 (2H, q, J = 8.3Hz), 6.68-6.78 (3H, m), 6.85-6.90 (1H, m) .

[Example 9-3]
Preparation of 4-heptafluoroisopropyl-2- (2,2,2-trifluoroethoxy) aniline

2- (2,2,2-trifluoroethoxy) aniline 2.85 g, 2-iodoheptafluoropropane 6.62 g, hydrosulfite sodium 3.11 g, sodium bicarbonate 1.50 g, tetra-n-butylammonium sulfate 0.61 g of hydrogen salt was added to a mixed solvent of 30 ml of t-butyl methyl ether and 30 ml of water, and stirred vigorously at room temperature for 12 hours. The organic phase was separated and washed with saturated aqueous sodium hydrogen carbonate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 9: 1) to give 13.99 g (yield 74%) of the title object product as a pale yellow oil.
_{^{1 H-NMR (CDCl 3,}} ppm) δ4.14 (2H, broad-s), 4.39 (2H, q, J = 7.8Hz), 6.79 (1H, d, J = 8.3Hz), 6.95 (1H, s ), 7.11 (1H, d, J = 8.3Hz).

[Example 9-4]
Preparation of 2-bromo-4-heptafluoroisopropyl-6- (2,2,2-trifluoroethoxy) aniline

The title product was prepared according to the conditions described in Example 1-2 using 4-heptafluoroisopropyl-2- (2,2,2-trifluoroethoxy) aniline as a starting material. Brown oil. Yield 88%.
¹ H-NMR (CDCl ₃ , ppm) δ 4.41 (2H, q, J = 7.8Hz), 4.58 (2H, broad-s), 6.90 (1H, s), 7.39 (1H, s).

[Example 9-5]
N- [2-Bromo-4-heptafluoroisopropyl-6- (2,2,2-trifluoroethoxy)] phenyl 3-[(N′-benzoyl-N′-methyl) amino] benzamide (Compound No. 2- 269)

The title product was prepared according to the conditions described in Example 3-3 using 2-bromo-4-heptafluoroisopropyl-6- (2,2,2-trifluoroethoxy) aniline as a starting material. White amorphous. Yield 69%.
¹ H-NMR (CDCl ₃ , ppm) δ3.54 (3H, s), 4.42 (2H, q, J = 7.8Hz), 7.14-7.21 (3H, m), 7.24-7.31 (4H, m), 7.37 (1H, t, J = 7.8Hz), 7.46 (1H, s), 7.60-7.62 (2H, m), 7.66-7.69 (1H, m).

[Example 10-1]
Preparation of 4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -2- (trifluoromethylthio) aniline

While mixing 5.0 g of 2-trifluoromethylthioaniline and 6.5 g of hexafluoroacetone hydrate at room temperature, 0.1 g of p-toluenesulfonic acid monohydrate was added, and the reaction solution was stirred at 100 ° C. for 20 minutes. Stir for hours. After confirming the disappearance of the starting material by TLC, ethyl acetate and saturated aqueous sodium hydrogen carbonate were added to the reaction solution, followed by liquid separation extraction. Anhydrous magnesium sulfate was added to the organic phase, dried and filtered. The residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to give 4.74 g (yield 51%) of the title product as a brown oil. Got as.
_{^{1 H-NMR (CDCl 3,}} ppm) δ4.71 (2H, broad), 6.81 (1H, d, J = 8.8Hz), 7.58 (1H, d, J = 8.8Hz), 7.84 (1H, d, J = 1.5Hz).

[Example 10-2]
Preparation of 2-bromo-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethylthio) aniline

4- [1-Hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -2- (trifluoromethylthio) aniline as a starting material according to the conditions described in Example 1-2 The title object was produced. Red oil. Yield 81%.

[Example 10-3]
N- [2-Bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] Preparation of 3-nitrobenzamide

As described in Example 1-3, starting from 2-bromo-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethylthio) aniline The title product was prepared according to the conditions described above. White solid. Yield 70%.

[Example 10-4]
N- [2-Bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] Preparation of 3-aminobenzamide

N- [2-Bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-nitrobenzamide as a starting material The title product was prepared according to the conditions described in Examples 1-4. White solid. Yield 90%.

[Example 10-5]
N- [2-bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-[(2-fluorobenzoyl) ) Production of amino] benzamide

N- [2-Bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-aminobenzamide and 2-fluoro The title compound was prepared according to the conditions described in Example 1-5 using benzoyl chloride as a starting material. White solid. Yield 84%.

[Example 10-6]
N- [2-Bromo-4- {1-chloro-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-[(2-fluorobenzoyl) ) Production of amino] benzamide

N- [2-Bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-[(2 at room temperature -Fluorobenzoyl) amino] benzamide (1.0 g) and pyridine (0.2 g) were charged into 10 ml of thionyl chloride. Then, it heated up and stirred under recirculation | reflux conditions. After confirming disappearance of the raw material by TLC, the reaction solution was concentrated under reduced pressure after cooling. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 3: 1) to obtain 0.77 g (yield 75%) of the title object as a white solid.

[Example 10-7]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(2-fluorobenzoyl) amino] benzamide (Compound No. 1-143)

N- [2-Bromo-4- {1-chloro-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-[(2 at room temperature -Fluorobenzoyl) amino] benzamide 400 mg and potassium fluoride 166 mg were charged into 10 ml of N, N-dimethylformamide. Thereafter, the temperature was raised to 120 ° C. and stirred for 5 hours. After cooling to room temperature, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. Anhydrous magnesium sulfate was added and the mixture was dried and filtered, and the filtrate was concentrated under reduced pressure. Diisopropyl ether was added to the obtained residue and washed. The filtrated product obtained by filtering the suspension was dried under reduced pressure at room temperature to obtain 281 mg (yield 72%) of the title object.
¹ H-NMR (DMSO-d ₆ , ppm) δ7.33-7.40 (2H, m), 7.57-7.62 (2H, m), 7.68-7.73 (1H, m), 7.81 (1H, d, J = 7.8 Hz), 8.01 (1H, d, J = 7.8Hz), 8.04 (1H, s), 8.30 (1H, d, J = 2.0Hz), 8.37 (1H, s), 10.70 (1H, s), 10.95 ( 1H, s).

[Example 10-8]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-[(2-fluorobenzoyl) amino] benzamide (Compound 1-143)

N- [2-Bromo-4- {1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] 3-[(2 at room temperature -Fluorobenzoyl) amino] benzamide 300 mg was charged into 20 ml of methylene chloride. Next, 470 mg of 2,2-difluoro-1,3-dimethyl-2-imidazolidinone was added dropwise and stirred at room temperature for 8 hours. Water was added to the reaction solution to separate the organic phase. Anhydrous magnesium sulfate was added to the organic phase, dried and filtered. The obtained filtrate was concentrated to dryness under reduced pressure, and the resulting solid was pulverized to obtain 181 mg (yield 60%) of the powdery target product.
The physical property values are described in Example 10-7.

[Example 11-1]
Preparation of 2-trifluoromethoxy-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline

While mixing 3.38 g of 2-trifluoromethoxyaniline and 4.75 g of hexafluoroacetone hydrate at room temperature, 0.1 g of p-toluenesulfonic acid monohydrate was added, and the reaction solution was stirred at 100 ° C. for 20 minutes. Stir for hours. After confirming the disappearance of the starting material by TLC, ethyl acetate and saturated aqueous sodium hydrogen carbonate were added to the reaction solution, followed by liquid separation extraction. Anhydrous magnesium sulfate was added to the organic phase, dried and filtered. The residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to give 3.60 g (yield 55%) of the title product as a brown oil. Got as.
¹ H-NMR (CDCl ₃ , ppm) δ3.37 (1H, broad-s), 4.10 (2H, broad-s), 6.83 (1H, d, J = 8.8Hz), 7.39 (1H, d, J = 8.8Hz), 7.50 (1H, s).

[Example 11-2]
Preparation of 2-bromo-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -6-trifluoromethoxyaniline

Starting from 2-trifluoromethoxy-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline as a starting material and according to the conditions described in Example 1-2, the title purpose The thing was manufactured. Red oil. Yield 92%.
¹ H-NMR (CDCl ₃ , ppm) δ3.98 (1H, t, J = 2.4Hz), 4.55 (2H, broad-s), 7.47 (1H, s), 7.71 (1H, d, J = 1.5Hz ).

[Example 11-3]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3- (benzoylamino) benzamide (Compound 1-243)

Examples 10-3 to 10-7 using 2-bromo-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -6-trifluoromethoxyaniline as a starting material The title product was prepared according to the conditions described in 1. White solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ7.48-7.67 (4H, m), 7.73-7.81 (2H, m), 7.94-8.14 (4H, m), 8.38 (1H, s), 10.51 ( 1H, s), 10.63 (1H, s).

[Example 12-1]
Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfinyl) phenyl 3-nitrobenzamide

9.56 g of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) thio] phenyl 3-nitrobenzamide prepared in Example 1-3 and 2.80 g of metachloroperbenzoic acid were added to 100 ml of dichloromethane. The mixture was stirred overnight at room temperature. To the reaction solution, 2.70 g of metachloroperbenzoic acid was added, and the mixture was further stirred at room temperature for 96 hours. A saturated aqueous sodium thiosulfate solution was added to the reaction solution, and the organic phase was separated, washed with water, and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1) to give 5.80 g (yield 59%) of the desired product as a white solid. Got as.
¹ H-NMR (CDCl ₃ , ppm) δ 7.80 (1H, t, J = 7.8Hz), 8.18 (1H, d, J = 2.0Hz), 8.24 (1H, s), 8.30 (1H, dd, J = 2.0, 7.8Hz), 8.46 (1H, s), 8.53 (1H, dd, J = 2.0, 7.8Hz), 8.80 (1H, t, J = 2.0Hz).

[Example 12-2]
Preparation of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-aminobenzamide

1.02 g of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-nitrobenzamide and 0.99 g of stannous chloride (anhydrous) are added to 10 ml of ethanol, and then concentrated hydrochloric acid 1 ml was added dropwise. After charging, the temperature was raised to 60 ° C. and stirred for 4 hours. The reaction solution was neutralized with sodium hydroxide under ice-cooling, and the precipitated insoluble material was removed by filtration using celite. The filtrate on celite was washed with ethyl acetate. The organic phase of the filtrate was washed with 20% aqueous sodium hydroxide solution and saturated brine, and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to obtain 0.83 g of the desired product (yield 85%) as a white solid. Got as.
¹ H-NMR (CDCl ₃ , ppm) δ3.95 (2H, broad), 6.92 (1H, dd, J = 2.0, 7.3Hz), 7.23 (1H, s), 7.24 (1H, d, J = 7.3Hz ), 7.31 (1H, t, J = 7.3Hz), 8.11 (1H, d, J = 7.3Hz), 8.17 (1H, s), 8.30 (1H, s).

[Example 12-3]
Preparation of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3- (methylamino) benzamide

To 10 ml of concentrated sulfuric acid, 1.96 g of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-aminobenzamide was added and stirred. Subsequently, 5.6 ml of 37% formaldehyde aqueous solution was dropped while maintaining the liquid temperature of 30 to 40 ° C., and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with 20% aqueous sodium hydroxide solution and water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with diisopropyl ether to obtain 1.30 g (yield 65%) of the desired product as a white solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ 2.80 (3H, s), 4.99 (1H, broad), 7.07-7.08 (1H, m), 7.28 (1H, d, J = 7.3Hz), 7.48- 7.49 (1H, m), 7.51 (1H, s), 8.13 (1H, d, J = 2.0Hz), 8.24 (1H, s), 10.12 (1H, broad).

[Example 12-4]
N- [2-Bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-{[N ′-(2-chloropyridin-3-yl) carbonyl-N′-methyl] amino} benzamide Production of (Compound No. 2-180)

Example 1-5 using 2-chloronicotinic acid chloride starting from N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3- (methylamino) benzamide The title product was prepared by following the conditions described in 1. White amorphous. Yield 70%.
¹ H-NMR (CDCl ₃ , ppm) δ3.58 (3H, s), 7.15 (1H, dd, J = 4.9, 7.3Hz), 7.42-7.45 (2H, m), 7.60 (1H, d, J = 7.3Hz), 7.71-7.72 (2H, m), 8.13 (1H, s), 8.19-8.29 (3H, m).

[Example 12-5]
N- [2-Bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-{[N ′-(pyrimidin-5-yl) carbonyl-N′-methyl] amino} benzamide (Compound No. 2-281)

Starting from N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-aminobenzamide prepared in Example 12-3, pyrimidine-5-carboxylic acid chloride was used. The title product was prepared by following the conditions described in Example 1-5. Pale yellow solid. Yield 53%.
¹ H-NMR (CDCl ₃ , ppm) δ3.59 (3H, s), 7.34 (1H, d, J = 8.3 Hz), 7.51 (1H, t, J = 7.8 Hz), 7.78 (2H, dd, J = 3.9, 1.5Hz), 8.14 (1H, d, J = 2.0Hz), 8.24 (1H, s), 8.35 (1H, s), 8.67 (2H, s), 9.11 (1H, s).
Next, typical preparation examples of the present invention are shown, but the present invention is not limited thereto. In the preparation examples, “parts” means “parts by weight”.

[Formulation Example 1]
2 parts of Compound 2-180, 10 parts of probenazole, 0.5 part of wetting agent (trade name Airol CT-1 manufactured by Toho Chemical Industry Co., Ltd.), 3 parts of binder (manufactured by Nippon Synthetic Chemical Co., Ltd., Gohsenol) , 15 parts talc (trade name Victorylite manufactured by Katsumiyama Mining Co., Ltd.) and 71.5 parts clay (trade name SP manufactured by Katsuyama Co., Ltd., trade name SP) are mixed, and after addition, extrusion granulator Molded with. The obtained molded product was dried and then sized to obtain granules.

[Formulation Example 2]
2 parts of Compound 2-180, 5 parts of orisatrobin, 0.5 part of wetting agent (trade name Airol CT-1 manufactured by Toho Chemical Industry Co., Ltd.), binder (made by Daiichi Kogyo Seiyaku Co., Ltd., trade name cellogen) ) 3 parts, 15 parts of talc (trade name Victorylite, manufactured by Katsumiyama Mining Co., Ltd.) and 74.5 parts of clay (trade name SP, manufactured by Katsuyama Industrial Co., Ltd.), mixed and extruded, and then extruded. Molded with a granulator. The obtained molded product was dried and then sized to obtain granules.

[Formulation Example 3]
0.5 part of compound 2-141, 0.2 part of kasugamycin monohydrochloride, 0.3 part of flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles C), clay (manufactured by Asahi Mizue Co., Ltd., trade name) 50 parts of O-4410) and 49 parts of calcium carbonate (product name NN # 200, manufactured by Nitto Flour Industry Co., Ltd.) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 4]
0.5 part of compound 1-243, tricyclazole 1.0 part, flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles A) 0.3 part, clay (manufactured by Asahi Minesue Co., Ltd., trade name O-4410) ) 50 parts, 48.2 parts of calcium carbonate (manufactured by Nitto Flour Chemical Co., Ltd., trade name NN # 200) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 5]
Compound 2-180 0.5 part, flutolanil 2.0 part, flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles A) 0.3 part, clay (manufactured by Asahi Mineral Co., Ltd., trade name O-4410 ) 50 parts, 47.2 parts of calcium carbonate (manufactured by Nitto Flour Chemical Co., Ltd., trade name NN # 200) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 6]
Compound 2-141 0.5 parts, fursulfamide 0.3 parts, flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles A) 0.3 parts, clay (manufactured by Asahi Mineral Co., Ltd., trade name O-) 4410) 50 parts and 48.9 parts of calcium carbonate (manufactured by Nitto Flour Chemical Co., Ltd., trade name Doreres A) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 7]
Compound 1-243 0.5 part, fenitrothion 3.0 part, flocculant (manufactured by Sankyo Co., Ltd., Doreless A) 0.3 part, amorphous hydrous silicic acid (manufactured by Degussa Japan Co., Ltd., trade name Carplex) # 80D) 2.0 parts, clay (made by Asahi Minesue Co., Ltd., trade name O-4410) 50 parts, calcium carbonate (made by Nitto Flour Chemical Co., Ltd., trade name NN # 200) 44.2 parts The mixture was mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 8]
5 parts of Compound 2-180, 10 parts of imidacloprid, 1.5 parts of wetting / dispersing agent (trade name Solpol 3074, manufactured by Toho Chemical Industry Co., Ltd.), dispersing agent (trade name, Demol N, manufactured by Kao Corporation) 2 .5 parts, 0.08 part of thickener (Rhodia Nikka Co., Ltd., trade name Road Pole) and 80.92 parts of water were mixed, pulverized with a wet pulverizer and filtered to obtain a flowable agent. Obtained.

[Formulation Example 9]
10 parts of Compound 2-141, 15 parts of pyridaben, 2.5 parts of wetting and dispersing agent (trade name Solpol 3074, manufactured by Toho Chemical Industry Co., Ltd.), dispersant (trade name Demol N, manufactured by Kao Corporation) 3 0.0 part, a thickener (Rhodia Nikka Co., Ltd., trade name Road Pole) 0.08 part and water 69.42 parts were mixed, then pulverized with a wet pulverizer and filtered to obtain a flowable agent. Obtained.

[Formulation Example 10]
10 parts of Compound 1-243, 5 parts of chlorfenapyr, 1.5 parts of wetting / dispersing agent (trade name Solpol 3074, manufactured by Toho Chemical Industry Co., Ltd.), dispersing agent (trade name, Demol N, manufactured by Kao Corporation) 2 .5 parts, 0.08 part of thickener (Rhodia Nikka Co., Ltd., trade name Road Pole) and 80.92 parts of water were mixed, pulverized with a wet pulverizer and filtered to obtain a flowable agent. Obtained.

[Formulation Example 11]
10 parts of compound 2-180, 20 parts of buprofezin, 1.5 parts of wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.5 parts of dispersant (trade name Emar, manufactured by Kao Corporation) Then, 2.0 parts of a dispersant (trade name Demol N, manufactured by Kao Corporation) and 64 parts of diatomaceous earth were mixed and then pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 12]
10 parts of compound 2-141, 20 parts of pymetrozine, 1.5 parts of a wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.5 parts of a dispersant (trade name Emar, manufactured by Kao Corporation) Then, 2.0 parts of a dispersant (trade name Demol N, manufactured by Kao Corporation) and 64 parts of diatomaceous earth were mixed and then pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 13]
10 parts of Compound 1-243, 5 parts of fipronil, 2.0 parts of a wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.0 parts of a dispersant (trade name Emar, manufactured by Kao Corporation) Then, 2.0 parts of a dispersant (trade name Demol N, manufactured by Kao Corporation) and 79 parts of diatomaceous earth were mixed, and then pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 14]
30 parts of isoxathion, 2.0 parts of a dispersant (trade name Solpol 7290P, manufactured by Toho Chemical Industry Co., Ltd.) and 25 parts of amorphous hydrous silicic acid (trade name Carplex # 80D, manufactured by Degussa Japan Co., Ltd.) were mixed. Thereafter, 10 parts of Compound 2-180, 1.5 parts of a wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.0 parts of a dispersant (trade name Emar, manufactured by Kao Corporation), dispersed After mixing 2.0 parts of an agent (trade name Demol N, manufactured by Kao Corporation) and 27.5 parts of diatomaceous earth, the mixture was pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 15]
5 parts of compound 2-141, 5 parts of dinotefuran, 2.0 parts of a wetting agent (manufactured by Toho Chemical Co., Ltd., Solpol 5050), 2.0 parts of a dispersant (trade name Emar, manufactured by Kao Corporation), and After mixing 86 parts of diatomaceous earth, the mixture was pulverized with a jet mill to obtain a wettable powder.
Furthermore, in order to clarify that the pest control composition of the present invention has an excellent pest control effect, test examples are shown below, but the present invention is not limited thereto.

[Test Example 1]
Insecticidal test against peach aphid Planted eggplant (variety: Senryo 2) in a plastic pot with a diameter of 8 cm and a height of 8 cm, and after breeding the peach aphid, sprayed the medicinal solution diluted to a predetermined concentration on the foliage. . After air drying, the pot was left in the greenhouse, and after 5 days of spraying, the number of aphids parasitic on each eggplant was investigated, and the control rate was calculated according to the following criteria (1 ward 1 pot 2 continuous system).
Control rate = 100 − {(Ta × Cb) / (Tb × Ca)} × 100
Table 11 shows the results of the number of parasites after spraying in the treated group Tb: the number of parasites before spraying in the treated group Ca: the number of parasites after spraying in the untreated group Cb: the number of parasites before spraying in the untreated group.

[Test Example 2]
Insecticidal test against resistant cotton aphids After planting cucumbers (variety: Sagami Hanjiro) in a plastic pot with a diameter of 8 cm and a height of 8 cm, and breeding resistant cotton aphids, the medicinal solution diluted to the prescribed concentration is applied to the foliage. Sufficiently sprayed. After air drying, the pot was left in the greenhouse, and after 5 days of spraying, the number of aphids parasitic on each cucumber was investigated, and the control rate was calculated according to the following criteria (1 ward 1 pot 2 continuous system).
Control rate = 100 − {(Ta × Cb) / (Tb × Ca)} × 100
Table 12 shows the results of the number of parasites after spraying in the treated group Tb: the number of parasites before spraying in the treated group Ca: the number of parasites after spraying in the untreated group Cb: the number of parasites before spraying in the untreated group.

[Test Example 3]
Insecticidal test for Japanese brown planthopper Sprinkle a solution prepared by diluting to a predetermined concentration on rice seedlings (variety: Koshihikari), air-dry, and put in a glass test tube with a diameter of 3 cm and a height of 10 cm together with 10 Japanese rice planters. Cotton plug was put on. The number of survivors 6 days after the treatment was investigated, and the death rate was calculated (2 units per 10 wards in 1 ward). The results are shown in Table 13.

[Test Example 4]
Insecticidal test against a spider mite Filled with a plastic cup with a diameter of 8 cm, put a lid with a hole with a diameter of 1 cm, place absorbent cotton on the top of the lid, hang it underwater from the lid, and the absorbent cotton is always moistened by capillary action I made it. A leaf disk having a diameter of 2 cm was prepared from green kidney leaves and placed on the absorbent cotton, and 4 adult females of the spider mite were inoculated there. On the next day, the female adults were removed, the number of eggs laid was examined, and a chemical solution prepared to a predetermined concentration was sprayed using a vertical sprayer. After spraying, it was placed in a constant temperature room at 25 ° C., and the number of hatched larvae surviving on the leaf disk was investigated 6 days after spraying, and the hatched larvae rate was calculated (1 drug, 1 concentration, 2 consecutive). The results are shown in Table 14.

[Test Example 5]
Tests for control of Japanese brown planthopper and corn borer by application of rice seedling box After 50g of granules were treated per box on rice (cultivar: Nipponbare), transplanted to Honda. As for the control effect on Japanese brown planthopper, the number of parasites was investigated for 30 strains in each group 40 days and 60 days after transplantation, and as for the control effect on corn borer, the number of damaged leaves was investigated for 100 strains in each group 50 days after transplantation, and the rate of damaged leaves was calculated. The results are shown in Table 15.

[Test Example 6]
Insecticidal test against mung beetle larvae Cut cabbage leaves for 30 seconds in chemical solution diluted to a predetermined concentration, air-dried, put into a plastic container with a diameter of 9 cm, inoculate 10 mites of 2 maturity larvae, and kept still in a constant temperature room at 25 ° C. I put it. Six days after the treatment, the number of surviving insects was examined, and the death rate was calculated (2 units per 10 wards in 1 ward). The results are shown in Table 16.

[Test Example 7]
Nika-meiga insecticidal test and rice blast control test using rice seedling box application After treatment of rice (variety: Koshihikari) grown in a seedling box with a prescribed amount of granules, 4 plants are transplanted in 1 / 5000a pots for 4 pots. did. 14 days after the treatment of 2 pots, the stems and leaves were cut out and placed in a plastic cup (diameter 10 cm, height 10 cm) together with 10 second instar larvae, and the mortality was investigated 4 days later (two-running system). The other 2 pots were placed in an artificial weather chamber (setting conditions: 25 ° C., 12 hours light / dark cycle) 30 days after the treatment, and spray-inoculated with a rice blast spore suspension. The weather chamber was kept at high humidity, and after 7 days, the number of blast spots was investigated, and the control value was calculated by the following formula (two continuous systems). The results are shown in Table 17.
Control value = (1−number of lesions in treated area / number of lesions in untreated area) × 100

[Test Example 8]
Paddy rice Ichimongiseseri and blast control test Rice powder (variety: Koshihikari) 70 days after transplanting (mid-May) was sprayed with a powder at a predetermined concentration. Prior to spraying, the leaves that had been parasitic on Ichimongiseseri were removed, and the number of insects was examined for 100 strains in each group 20 days after spraying. In addition, an affected seedling of blast disease was placed in the center of each ward 10 days before spraying, and after 30 days of spraying, the number of ear blasting ears was investigated for 20 strains in each ward, and the control value was calculated by the following formula. The results are shown in Table 18.
Degree of damage a: Onset of head neck b: Onset of branch infarction 1/3 or more c: Onset of inferior branch infarction 1/3 Injury = attack rate of a + onset rate of b × 0.66 + onset rate of c × 0.26
Control value = (1-Damage level of treated area / Damage level of untreated area) x 100

[Test Example 9]
Paddy rice Ichimon dissemination and blight control test Rice (variety: Koshihikari) 70 days after transplanting (mid-May) was sprayed with a predetermined amount of powder. Prior to spraying, the leaves that had been parasitic on Ichimongiseseri were removed, and the number of insects was examined for 100 strains in each group 20 days after spraying. Further, rice plant blight fungus cultivated in a bran medium 7 days before spraying was inoculated to the plant origin, and 30 days after spraying, the pathogenic strain was investigated for 100 strains in each ward, and the pathogenic strain rate was calculated. The results are shown in Table 19.

[Test Example 10]
A pear pear and scab control test A 17-year-old pear (variety: Hosui) was sprayed with a sufficient amount of a drug prepared at a predetermined concentration (early June). Forty days after spraying, the number of fruits damaged by Nashihimeshinki was investigated for all fruits in the ward, and the rate of damage was calculated. Further, on the 14th day after spraying, the occurrence of scab was investigated for any 200 leaves in the ward according to the degree, and the severity was calculated by the following formula. The results are shown in Table 20.
Disease severity = Σ (number of diseased leaves by degree × index) × 100 / (number of leaves surveyed × 5)
Index: (0: No disease, 1: 1 to 3 lesions, 3: 4 to 7 lesions, 5: 8 or more lesions)

[Test Example 11]
Cucumber urine borer insecticidal test and powdery mildew control test A sufficient amount of the drug prepared at a predetermined concentration was sprayed on cucumber (variety: Sagamihanjiro) cultivated in a greenhouse. Seven days after spraying, one leaf was cut out and put into a plastic cup (diameter 10 cm, height 10 cm) together with 5 2nd instar larvae, and the mortality was investigated 4 days later. In addition, powdery mildew on the diseased leaves of cucumber that had been diseased one day after spraying was uniformly inoculated with a paint brush and inoculated 10 days later. The area occupied by lesions per cucumber leaf was examined according to the following index, and the control value was calculated from the average disease severity in each section using the following formula (two-line system). The results are shown in Table 21.
Disease severity 0: No lesion
1: lesion area is 5% or less
2: The lesion area is 6-25%
3: The lesion area is 26-50%
4: The lesion area is 51% or more Control value = (1−average disease severity in treated area / average disease severity in untreated area) × 100

[Test Example 12]
Test of controlling cabbage and root-knot disease by soil treatment of cabbage Planted cabbage (variety: four seasons) cultivated with cell seedlings with a prescribed amount of powder mixed with soil. Seven days after the treatment, the number of strains damaged by Cabrayaga was investigated and the rate of damaged strains was calculated. In addition, 60 days after the treatment, the strain was extracted, and the occurrence of root-knot disease was investigated according to the degree. The results are shown in Table 22.
Disease severity 0: Does not recognize root-knot formation
1: The root hump grows on less than 1-25% of the root system
2: The root humps grow on less than 25-50% of the root system
3: Root bumps grow on less than 50-75% of the root system
4: Root humps grow on roots of 75% or more of the whole root system Control value = (1−average disease severity in treated area / average disease severity in untreated area) × 100

[Test Example 13]
Insecticidal test against citrus thrips larvae A 1% agar gel was injected into a plastic cup (5 cm in diameter and 5 cm in height), and a leaf disk was prepared by placing the fresh leaf of kidney beans cut into a diameter of 4.5 cm on the back of the leaf. Three pre-mating female adults were released, covered and allowed to lay eggs for 2 days. Thereafter, the female adults were removed, and after 4 days, the number of larvae on the leaf discs was counted, and a prescribed concentration of drug was sprayed with a vertical sprayer. Three days after spraying, the number of live insects was counted, and the corrected survival rate was calculated by the following formula. The results are shown in Table 23.
Corrected survival rate = 100 × Ta × Cb / (Tb × Ca)
Ta: Number of surviving insects after spraying in the treated group Tb: Number of surviving insects before spraying in the treated group Ca: Number of surviving insects after spraying in the untreated group Cb: Number of surviving insects before spraying in the untreated group

[Test Example 14]
Rice blast control effect
A predetermined amount of wettable powder and a commercially available seed fungicide (Trihumine wettable powder) were each soaked for 48 hours in naturally infected rice fir (variety: Koshihikari). After soaking (15 ° C., 3 days) and germination (30 ° C., 24 hours), seeds treated with chemicals and seeds not treated with chemicals were sown 100 times per pot in plastic pots. And grown in a greenhouse. After 20 days of cultivation, all seedlings were examined for the presence of disease with the naked eye, and the diseased seedling rate was calculated. The presence or absence of phytotoxicity was also examined with the naked eye. The results are shown in Table 24.
Disease seedling rate = (number of diseased seedlings / total number of surveyed seedlings) × 100

[Test Example 15]
Control effect of sugar beet against flea beetle A predetermined amount of wettable powder was treated with a seed dressing machine (chemical injection in a rotating drum).
After 45 days of treatment, the degree of damage caused by the flea beetle was indexed and the control rate was calculated.
The presence or absence of phytotoxicity was also examined with the naked eye.
The results are shown in Table 25.
The degree of damage and the index are as follows: Index 0: No damage, Index 1: Less damage
Index 2: Medium degree of food damage, Index 3: High degree of food damage Control rate = 100 − ((1 × index 1 number of food damage + 2 × number of food damages of index 2 + 3 × index 3 number of food damages) / 3 × total number of surveys × 100)

[Test Example 16]
Control effect against Azuki beetle
A flowable agent of a predetermined dose was applied to 1 kg of azuki bean seeds by 5, 10, 20 ml. After air drying, a part was transferred to a 9 cm waist high petri dish and left in a constant temperature room at 25 ° C. After 2 and 3 months of treatment, 10 adult weevil pupae were released per waist-high petri dish (5-regulation). Two days after the release, the number of dead insects and the number of eggs laid on azuki bean were examined, and the death rate was calculated. The presence or absence of phytotoxicity was also examined with the naked eye.
The results are shown in Table 26.
Death rate = (Number of dead insects in the treatment area / 50) x 100

Claims (28)

General formula (1)

{Where
A ₁ , A ₂ , A ₃ , A ₄ each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X is a hydrogen atom, a halogen atom or a trifluoromethyl group,
n represents an integer from 0 to 4,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1 -C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group , C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or, shows the C1-C6 perfluoroalkyl sulfonyl group, Y _2, Y ₄ each independently represent a hydrogen atom, a halogen atom or C1-C4 alkyl group, shows .) In either represented or,
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 An alkyl group, wherein at least one of Y ₆ and Y ₉ must be a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 halo; Represents an alkylsulfinyl group or a C1-C3 haloalkylsulfonyl group. } As an active ingredient, one or two or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides or known fungicides A pest control composition characterized by the above. In the general formula (1), the compound represented by the general formula (1)
A ₁ , A ₂ , A ₃ , A ₄ each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X is a hydrogen atom, a halogen atom or a trifluoromethyl group,
n represents an integer from 0 to 4,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1 -C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group , C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or, shows the C1-C6 perfluoroalkyl sulfonyl group, Y _2, Y ₄ each independently represent a hydrogen atom, a halogen atom or C1-C4 alkyl group, shows .) In either represented or,
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 An alkyl group, wherein at least one of Y ₆ and Y ₉ must be a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 halo; A compound represented by an alkylsulfinyl group or a C1-C3 haloalkylsulfonyl group (wherein Y ₁ is a trifluoromethylthio group, Y ₂ and Y ₄ are hydrogen atoms, Y ₃ is a heptafluoroisopropyl group, and Y ₅ is Bromine atom, X is a hydrogen atom, G ₁ and G ₂ are oxygen atoms, R ₁ and R ₂ are hydrogen atoms, and Q ₁ is an unsubstituted phenyl group. A pest control composition as described in 1. above. The compound represented by the general formula (1) is represented by the general formula (1a).

{Where
When either R ₁ or R ₂ is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both are a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group. ,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), Or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or a C1-C4 represents an alkyl group. here, Y _6, at least one is always C1-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru Represented by showing a Rusuruhoniru group.). } The pest control composition of Claim 1 or 2 which is a compound represented by these. In the general formula (1a), the compound represented by the general formula (1)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl Group, or cyano group, Y ₃ represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) The pest control composition listed. In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. It is a compound represented by Jill group, pest control composition of claim 4. In the general formula (1a), the compound represented by the general formula (1)
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1 -C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 A group having one or more substituents which may be the same or different and are selected from an alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; Phenyl group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), Or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or a C1-C4 represents an alkyl group. here, Y _6, at least one is always C1-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru Shows the Rusuruhoniru group.) Is a compound represented by the pest control composition according to claim 1 or 2. In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1 -C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 A group having one or more substituents which may be the same or different and are selected from an alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; Phenyl group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Represented by Jill group,
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) The pest control composition listed. In the general formula (1a), the compound represented by the general formula (1)
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is fluorine atom, chlorine atom, iodine atom, C1-C4 alkyl group, C1- C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group shows a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl, Y ₂ and Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) Or the general formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or a C1-C4 represents an alkyl group. here, Y _6, at least one is always C1-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru Shows the Rusuruhoniru group.) Is a compound represented by the pest control composition according to claim 1 or 2. In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Represented by Jill group,
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is fluorine atom, chlorine atom, iodine atom, C1-C4 alkyl group, C1- C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group shows a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl, And Y ₂ and Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) The pest control composition according to claim 8, wherein In the general formula (1a), the compound represented by the general formula (1)
R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl represents a group or a cyano group,, Y ₃ represents a C2-C6 perfluoroalkyl group, C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl alkylsulfinyl group or a C1-C6 perfluoroalkyl sulfonyl group,, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.), Or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C2 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 represents an alkyl group. here, Y _6, at least one is always C2-C3 haloalkylthio group Y _9, C1-C3 haloalkylsulfinyl group or C1-C3 Haroaru Shows the Rusuruhoniru group.) Is a compound represented by the pest control composition according to claim 1 or 2. In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Represented by Jill group,
Q ₂ is the general formula (2)

(Wherein, Y ₁ is C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or C1-C3 haloalkylsulfonyl group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1- C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl Group, or cyano group, Y ₃ represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₂ , Y ₄ each independently represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.) The pest control composition as described. In the general formula (1), the compound represented by the general formula (1)
A ₁ , A ₂ , A ₃ , A ₄ each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
When either R ₁ or R ₂ is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both are a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group. ,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X is a hydrogen atom, a halogen atom or a trifluoromethyl group,
n represents an integer from 0 to 4,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ represents a C1-C4 alkoxy group or a C1-C4 haloalkoxy group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 halo An alkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, or a cyano group, Y ₃ represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, and Y ₂ and Y ₄ are each independently Represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group), or
General formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1 -C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group or a cyano group, Y ₈ is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₇ is a hydrogen atom, a halogen atom, or C1-C4 represents an alkyl group. here, Y _6, compound der represented by.) indicating at least one is always C1-C4 alkoxy group or a C1-C4 haloalkoxy group Y ₉ , Pest control composition of claim 1. In the general formula (1a), the compound represented by the general formula (1)
When either R ₁ or R ₂ is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both are a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group. ,
G ₁ and G ₂ are each independently an oxygen atom or a sulfur atom,
X ₁ , X ₂ , X ₃ and X ₄ are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
Q ₁ is a phenyl group, or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group, or tetrazolyl group), or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted compound having one or more of the same or different substituents selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. A ring group (the heterocyclic group have the same meanings as defined above.)
Q ₂ is the general formula (2)

(Wherein, Y ₁ represents a C1-C4 haloalkoxy group, Y ₅ is a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group,, Y ₃ is C2-C6 A perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group, Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom Or a C1-C4 alkyl group.) The pest control composition according to claim 12, which is a compound represented by: In the general formula (1a), the compound represented by the general formula (1)
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted group having one or more substituents which may be the same or different and selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. Group,
Pyridyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3- C6-halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkyl Sulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy A substituted phenyl having one or more substituents which may be the same or different, selected from a group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group. It is a compound represented by Jill group, pest control composition of claim 13. Known insecticides, known acaricides or known fungicides are azinephos methyl, acephate, isoxathion, isofenphos, etion, etrimphos, oxydimethone methyl, oxydeprophos, quinalphos, chlorpyrifos, chlorpyrifosmethyl, chlorfenvinphos, cyanophos, Dioxabenzophos, dichlorvos, disulfoton, dimethylvinphos, dimethoate, sulprophos, diazinon, thiometone, tetrachlorbinphos, temefos, tebupyrimfos, terbufos, nared, bamidthione, pyraclofos, pyridafenthione, pyrimifosmethyl, fenitrothion, fenthion, fentoate, fentolfofo Thion, Flupyrazophos, Prothiophos, Propafos, Profenofos, Hoxime, Hosalon, Ho Met, formothion, folate, malathion, mecarbam, mesulfenphos, methamidophos, metidathion, parathion, methylparathion, monocrotophos, trichlorfone, O-ethylphenyl-4-phosphonothiothio, isazophosthiothiphosfothathionophos , Hosthiethane, phosphocarb, O-4-dimethylsulfamoylphenyl O, O-diethylphosphothioate, etoprophos, alanicarb, aldicarb, isoprocarb, etiophencarb, carbaryl, carbosulfan, xylcarb, pyricarb, pyricarb Nobucarb, furthiocarb, propoxyl, bendiocarb, benfuracarb, mesomil, metorcarb, 3,5-xylylmethylcarbamate, carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate, pentrin, cyclohalothrin, cyhalothrin, cyhalothrin , Lambda siharthrin, cyfluthrin, beta cyfluthrin, cypermethrin, alpha cypermethrin, zeta cypermethrin, silafluophene, tetramethrin, tefluthrin, deltamethrin, tralomethrin, bifenthrin, phenothrin, fenvalerate, fenpropatoline, framethrin fluretrin Nates, fulvalinates, flubrosinates , Permethrin, Resmethrin, Metofluthrin, Dimefluthrin, Profluthrin, Etofenprox, Cartap, Thiocyclam, Benzlutap, Acetamiprid, Imidacloprid, Clothianidin, Dinotefuran, Thiacloprid, Thiamethoxam, Nitenpyram, Flufluzuron, Flufluzuron Bistrifluron, fluazuron, flucycloxuron, flufenoxuron, hexaflumulone, lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyphenozide, diophenolan, cyromazine, pyriproxyfen, buprofezin, methoprene, hydroprene, quinoprene, triazamate, endosulfan The Rufenson, chlorbenzilate, dicophore, bromopropyrate, acetoprole, fipronil, etiprole, pyrethrin, rotenone, nicotine sulfate, abamectin, Bacillus thuringiensis, spinosad, acequinosyl, amideflumet, amitraz, etoxazole, quinomethionate, clofentezine , Phenbutadium oxide, dienochlor, cyhexatin, spirodiclofen, spiromesifen, tetradiphone, tebufenpyrad, binapacryl, bifenazate, pyridaben, pyrimidifene, phenazaquin, phenothiocarb, fenpyroximate, fluacrylimine, fluazinam, flufenzine, polyhexinactin, polyhexinactin Milbemectin, Ruff Nuron, mecarbam, methiocarb, mevinphos, formethanate, halfenprox, azadirachtin, diafenthiuron, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate, chlorfenapyr, tolfenpyrad, pymetrozine, phenoxycarb, hydramethylnon , Hydroxypropyl starch, pyridalyl, flufenelim, flubendiamide, flonicamid, metaflumizone, repimectin, tripropyrisocyclic, levamisole hydrochloride, morantel tartrate, dazomet, metam sodium,
General formula (AA)

[Wherein R ₅₁ represents a methyl group or a chloro group, R ₅₂ represents a methyl group, a chloro group, a bromo group or a cyano group, and R ₅₃ represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group. R ₅₄ represents a methyl group or an isopropyl group. A compound represented by
Compound (BB),

Triazimephone, hexaconazole, propiconazole, ipconazole, prochloraz, triflumizole, tebuconazole, epoxiconazole, difenoconazole, flusilazole, triazimenol, cyproconazole, metconazole, fluquinconazole, vitertanol, tetraconazole, tritico Nazole, flutriafor, penconazole, diconazole, fenbuconazole, bromconazole, imibenconazole, cimeconazole, microbutanyl, himexazole, imazalyl, framethopyl, tifluzamide, etridiazole, oxpoconazole, oxpoconazole fumarate, pefazoate , Prothioconazole, Pyriphenox, Phenarimol, Nuarimol, Bupirimate, Mepanipiri , Cyprozinyl, pyrimethanil, metalaxyl, oxadixyl, benalaxyl, thiophanate, thiophanate methyl, benomyl, carbendazim, fuberidazole, thiabendazole, manzeb, propineb, dineb, methylam, mannebu, dilam, thiuram, chlorothalonil, ethaboxamil, oxyfluxanil, oxyflurane , Silthiofam, Mepronil, Dimethomorph, Fenpropidin, Fenpropimorph, Spiroxamine, Tridemorph, Dodemorph, Flumorph, Azoxystrobin, Cresoxime Methyl, Metominostrobin, Orisatrobin, Fluoxastrobin, Trifloxystrobin, Dimoxystrobin , Pyraclostrobin, picoxystrobin, iprodione, procymidone, Nclozoline, clozolinate, fursulfamide, dazomet, methyl isothiocyanate, chloropicrin, metasulfocarb, hydroxyisoxazole, hydroxyisoxazole potassium, eclomesol, 1,3-Dichloropropene, carbam, basic copper chloride, basic copper sulfate, nonylphenol Copper sulfonate, copper oxine, dodecylbenzene sulfonate bisethylenediamine copper complex salt (II), anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide, inorganic sulfur, hydrated sulfur agent, lime sulfur mixture, zinc sulfate , Fentin, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hypochlorite, metallic silver, edifenphos, tolcrofosmethyl, fosetyl, iprobenphos, dinocap, pyrazophos, carpropamide, fusalide, trisi Crasol, Pyroxylone, Diclocimet, Phenoxanil, Kasugamycin, Validamycin, Polyoxin complex, Blasticidin S, Oxytetracycline, Mildiomycin, Streptomycin, Rapeseed oil, Machine oil, Bench avalicarb isopropyl, Iprovaricarb, Propamocarb, Dietofencarb, Fluorimide Fludioxanyl, fenpicuronyl, quinoxyphene, oxolinic acid, chlorothalonil, captan, phorpet, probenazole, acibenzoral S methyl, thiazinyl, cyflufenamide, fenhexamide, diflumetrim, metolaphenone, picobenzamide, proquinazide, famoxadone, cyazofamide, phenamidonal, oxamidon, zoxamid, Dithia , Fluazinam, Diclofluanid, Triphorine, Isoprothiolane, Ferimzone, Diclomedin, Teclophthalam, Pencyclon, Quinomethionate, Iminocazine Acetate, Iminocazine Albesylate, Ambamu, Polycarbamate, Thiadiazine, Chloroneb, Organonickel, Guazatine, Dodine, Kintozene, Tolylfluanid, anilazine, nitrotalisopropyl, fenitropan, dimethylolmol, benazole, harpin protein, flumetobar, mandipropamide, penthiopyrad,
General formula (CC)

[Wherein R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group and a heterocyclic alkyl group, R12 and R17 each represents a hydrogen atom, and R13 and R14 each represent Independently, it represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R15 and R16 each represent a hydrogen atom, and R18 represents an aryl group or a heterocycle. Or a compound represented by the general formula (DD)

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. ] The pest control composition of any one of Claims 1-14 which is a compound represented by these. Known insecticides, known acaricides or known fungicides are fenitrothion, fenthion, isoxathione, acephate, buprofezin, pyriproxyfen, silafluophene, dinotefuran, imidacloprid, etofenprox, halfenprox, thiamethoxam, clothianidin, acetamiprid, nitenpyram, thiacloprid , Benfuracarb, Mesomil, Fenobucarb, Spinosad, Pymetrozine, Chromafenozide, Lepimectin, Fipronil,
General formula (AA)

[Wherein R ₅₁ represents a methyl group or a chloro group, R ₅₂ represents a methyl group, a chloro group, a bromo group or a cyano group, and R ₅₃ represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group. R ₅₄ represents a methyl group or an isopropyl group. A compound represented by
Compound (BB),

Fenproxymate, pyridaben, hexothiazox, fenbutazin oxide, tebufenpyrad, pyrimidifen, etoxazole, polynactin complex, milbemectin, acequinosyl, befenazate, spirodiclofen, dienochlor, spiromesifen, tetradiphone, chlorfenapyr, clofentegi, tolfenpyramide , Difenthiuron, flufenoxuron, penthiopyrado, fursulfamide, iminotadine albecylate, acibenzoral S methyl, ferimzone, pyroxylone, oryastrostrobin, azoxystrobin, carpropamide, diclocimet, probenazole, thiazinyl, isoprothiolane, tricyclazole, fusalide, kasugamycin , Fenoki Nil, mepronil, dichromedine, penclone, validamycin A, edifenphos, furametopil, tifluzamide, flutolanil, metminostrobin, iprobenphos, oxolinic acid, teclophthalam, cimeconazole, hydroxyisoxazole, picoxystrobin, flusilazole, carboxin, tebuconazole, tri Azimenol, difenoconazole, thiabendazole, fludioxanyl, metalaxyl, streptomycin,
General formula (CC)

[Wherein R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group and a heterocyclic alkyl group, R12 and R17 each represents a hydrogen atom, and R13 and R14 each represent Independently, it represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R15 and R16 each represent a hydrogen atom, and R18 represents an aryl group or a heterocycle. Or a compound represented by the general formula (DD)

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. ] The pest control composition of Claim 15 which is a compound represented by these.   17. One to one compound selected from a known insecticide, a known acaricide or a known fungicide is contained in an amount of 0.001 to 95% by weight, respectively. Pest control composition. A pest control method comprising applying the pest control composition according to claim 17 to a pest or a habitat of the pest. A method for preventing damage by pests, which comprises applying the pest control composition according to claim 17 to plant seeds. A method for preventing damage by pests, which comprises contacting the plant seeds with the pest control composition according to claim 17. The prevention method according to claim 20, wherein the method for contacting the plant seeds is a spraying treatment, a smearing treatment, a dipping treatment or a powder coating treatment. Plant seeds are corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper and rape seed, taro, potato, The prevention method according to claim 19, which is a potato, konjac seed pod, edible lily or tulip bulb. The prevention method according to claim 22, wherein the plant seed is a transformed seed. A plant seed to which the pest control composition according to claim 17 is applied. A method for preserving plant seeds, comprising applying the pest control composition according to claim 17 to plant seeds. The preservation method according to claim 25, wherein the application method to the plant seed is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment or fumigation / smoke treatment. A method for preserving a crop, which comprises applying the pest control composition according to claim 17 to a crop of an agricultural plant. 28. The storage method according to claim 27, wherein the application method to the harvest of the agricultural plant is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment, fumigation / smoke treatment or pressure injection.