JP2007302617A - Heterocyclic derivative and method for using the derivative as insecticide - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound represented by the general formula (1) and exhibiting a high insecticidal effect, and to provide an insecticide containing the compound as an active ingredient. <P>SOLUTION: The compound represented by the general formula (1) [Het is a five-membered aromatized heterocyclic group; Z is -C(=G<SB>1</SB>)Q<SB>1</SB>, -C(=G<SB>1</SB>)G<SB>2</SB>R<SB>3</SB>(G<SB>1</SB>, G<SB>2</SB>are each O or the like; Q<SB>1</SB>, R<SB>3</SB>are each a substituted phenyl, a substituted heterocyclic group, a 1 to 6C alkyl, a 1 to 6C haloalkyl, or the like), or the like; X is H, a 1 to 3C alkyl or the like; (n) is an integer to 0 to 3; G<SB>3</SB>is O or the like; Q<SB>2</SB>is a substituted phenyl; a substituted pyridyl or the like; R<SB>1</SB>, R<SB>2</SB>are each H, a 1 to 4C alkyl, or the like], and the insecticide containing the compound as an active ingredient. The compound of the present invention exhibits high insecticidal activities and excellent control effects against various insect pests. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a novel heterocyclic derivative and a method of using it as an insecticide containing the compound as an active ingredient.

  In WO 2005/21488, a compound similar to the compound of the present invention is recognized as an insecticide, but it is clear that the compound is outside the scope of the claims of the present invention.

In WO 2005/73165 pamphlet, description of a compound similar to the compound of the present invention as an insecticide is recognized, but it is clear that the compound is outside the scope of the claims of the present invention.
International Publication No. 2005/21488 Pamphlet International Publication No. 2005/73165 Pamphlet

  An object of the present invention is to provide an insecticide having a high insecticidal effect. Another object of the present invention is to provide an insecticide containing the compound represented by the general formula (1) as an active ingredient.

  As a result of intensive studies to solve the above problems, the present inventors have found that the compound of the present invention is a novel compound not described in the literature and has a remarkably excellent insecticidal effect, and has completed the present invention. It has come to be.

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

{In the formula, Het is a 5-membered aromatic heterocyclic group (herein, the aromatic 5-membered heterocyclic group is pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, A thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a furyl group, a thienyl group, an oxadiazolyl group and a triazolyl group).
Z is _{-C (= G 1) Q 1} , -C (= G 1) G 2 R 3, -SO 2 Q 1 or -Q _{1 (wherein, G 1,} G ₂ represents an oxygen atom or a sulfur atom ,
Q ₁ and R ₃ are C1-C6 alkyl groups,
A C1-C6 haloalkyl group,
A C2-C6 alkenyl group,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group,
A C2-C6 haloalkynyl group,
A C3-C8 cycloalkyl group,
A C3-C8 halocycloalkyl group,
A phenyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement Fe Group,
A naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement naphth Group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, An oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group. C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 halo An alkylthio group, 1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, A substituted heterocyclic group having one or more substituents selected from a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (wherein the heterocyclic group is a pyridyl group, pyridine- N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl Group, thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group.),

-E ₁ -Z ₁ -R ₄
(Where
E ₁ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C2-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group,
R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group,
A C3-C8 cycloalkyl group,
A C3-C8 halocycloalkyl group,
A phenyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement Fe Group,
A naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement naphth Group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, An oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group), or the same or different, a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 halo An alkylthio group, 1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, A substituted heterocyclic group having one or more substituents selected from a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group is shown (the heterocyclic group here is a pyridyl group, Pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiyl Zoriru group, thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group.),

Z ₁ represents —O—, —S—, —SO—, —SO ₂ —, —C (═O) —, —C (═O) O—, —OC (═O) —, —N (R ₅ ) -, - C (= O ) N (R 5) -, or _{-N (R 5) C (=} O) - (R 5 is a hydrogen atom, C1-C4 alkyl groups, C1-C4 alkylcarbonyl groups, C1 -Represents a C4 haloalkylcarbonyl group or a C1-C4 alkoxycarbonyl group. ),
Or _-E 2 -R ₆
(Where
E ₂ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C2-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group,
R ₆ is a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,
A cyano group,
Nitro group,
A hydroxy group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, Or complex Group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group) , Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group).
Alternatively, they may be the same or different and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group. Group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy Substituted heterocyclic ring having one or more substituents selected from a group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group Group (where Heterocyclic groups are pyridyl, pyridine-N-oxide, pyrimidinyl, pyrazinyl, pyridazyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, oxazolyl, isoxazolyl, oxadiazolyl Group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, or tetrazolyl group). ) And
G ₃ represents an oxygen atom or a sulfur atom,
X may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group,
n represents an integer of 0 to 3,
Q ₂ may be a phenyl group, or may be the same or different, and may be a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group. C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1 -C6 haloalkylsulfonyloxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, phenyl group, the same or different, halogen atom, C1 -C6 Alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 haloalkylsulfonyloxy group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group A phenyl group, a thienyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, C1-C6 alkoxy group C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1- A substituted phenyl group having one or more substituents selected from a thienyl group optionally substituted with a C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxy group, and a pentafluorosulfanyl group,
A naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group A substituted naphthyl group having one or more substituents selected from a group, a hydroxy group, and a pentafluorosulfanyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, C1 -C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkyl Sul A substituted heterocyclic group having one or more substituents selected from a nyl group, a cyano group, a nitro group, a hydroxy group, and a pentafluorosulfanyl group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group) , Pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolyl group, or tetrazolyl group. ,
Tetrahydronaphthalene group,
Alternatively, they may be the same or different, and may be a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, One or more substitutions selected from C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group A tetrahydronaphthalene group having a group,
R ₁ and R ₂ are each a hydrogen atom, oxygen atom, halogen atom, hydroxy group, cyano group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group,
A C1-C4 alkyl group,
A C1-C4 alkylcarbonyl group,
A C1-C4 haloalkylcarbonyl group,
A C2-C4 alkenyl group,
A C2-C4 haloalkenyl group,
A C2-C4 alkynyl group,
A C2-C4 haloalkynyl group,
A C1-C4 alkoxycarbonyl group,
A C1-C4 haloalkoxycarbonyl group,
A C2-C4 alkenyloxycarbonyl group,
A C2-C4 alkynyloxycarbonyl group,
Phenoxycarbonyl group, which may be the same or different, may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, One or more substituents selected from a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group Yes Substituted phenoxycarbonyl group that,
A C1-C4 alkylaminocarbonyl group,
A C1-C4 haloalkylaminocarbonyl group,
A C1-C4 alkylcarbonyloxy group,
A C1-C4 haloalkylcarbonyloxy group,
Benzoyl group, which may be the same or different, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement Benzoyl group,
A C1-C4 alkoxy group,
A C1-C4 haloalkoxy group,
A benzyloxycarbonyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group One or more substituents selected from nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted benzyloxycarbonyl group having,
A C1-C4 alkylthio group,
A C1-C4 haloalkylthio group,
A C1-C4 alkylsulfinyl group,
A C1-C4 haloalkylsulfinyl group,
A C1-C4 alkylsulfonyl group,
A C1-C4 haloalkylsulfonyl group,
Benzenesulfonyl group, which may be the same or different, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, One or more substituents selected from a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group Have Substituted benzenesulfonyl group,
Benzylsulfonyl group, which may be the same or different, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, One or more substituents selected from a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group Have Substituted benzylsulfonyl group,
A C1-C4 alkoxy C1-C4 alkyl group,
A C1-C4 haloalkoxy C1-C4 alkyl group,
Or C (= O) C (= O) R ₇ (wherein R ₇ is a C1-C6 alkyl group,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group,
A C3-C8 halocycloalkyl group,
A C1-C6 alkoxy group,
Or a C1-C6 haloalkoxy group). }
A compound represented by

[2] The compound represented by the general formula (1) is represented by the following general formula (2)

(In the formula, A, E, and D independently represent a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and X, n, R ₁ , R ₂ , G ₃ , Z, and Q ₂ have the same meaning as described above. The compound of Claim 1 represented by this.

[3] In the general formula (2), Z is —C (= G ₁ ) Q ₁ , —C (= G ₁ ) G ₂ R ₃ , and Q ₂ is the general formula (3) (Chemical Formula 3)

(Wherein Y ₁ and Y ₅ may be the same or different and are each a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group). Group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, cyano group, Y ₃ is a C1-C6 haloalkyl group , A C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, and a C1-C6 haloalkylsulfonyl group, Y ₂ and Y ₄ represent a hydrogen atom, a halogen atom, and a C1-C4 alkyl group. ) Or the general formula (4)

(Wherein Y ₆ and Y ₉ may be the same or different and are each a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group). Group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, cyano group, Y ₈ is a C1-C6 haloalkyl group , C1-C4 haloalkoxy group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, _{Y 7} represents a hydrogen atom, a halogen atom, in.) showing the C1-C4 alkyl group The compound of [2] represented.

[4] The compound according to [3], wherein in general formula (2), A is a sulfur atom, E is a nitrogen atom, D is a carbon atom, or A and E are carbon atoms, and D is a nitrogen atom.

[5] An insecticide comprising the compound according to any one of [1] to [4] as an active ingredient.

  The compound of the present invention exhibits a control effect against various pests, and has the effect of greatly contributing to the reduction of environmental burden by reducing the amount of drug, as well as the effect of protecting useful crops.

  Terms used in general formulas such as the general formula (1) of the present invention have the meanings described below in their definitions.

  “5-membered aromatized heterocycle” means pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl, furyl, thienyl, oxadiazolyl, triazolyl A 5-membered heterocyclic group such as

“Halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
The notation "Ca-Cb (a, b represents an integer of 1 or more)" means, for example, that "C1-C3" has 1 to 3 carbon atoms, and "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.

  “C1-C4 alkyl group” means, for example, linear or branched chain such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, s-butyl, i-butyl, t-butyl, etc. An alkyl group having 1 to 4 carbon atoms.

  “C1-C6 alkyl group” means, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl-2 -A linear or branched alkyl group having 1 to 6 carbon atoms, such as -pentyl, n-hexyl, 3-methyl-n-pentyl and the like.

  The “C1-C4 haloalkyl group” means, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl, 2-fluoro Ethyl, 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-dichloro-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-propyl, 4-fluoro- linear or branched alkyl having 1 to 4 carbon atoms substituted by one or more halogen atoms which may be the same or different, such as n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, etc. Indicates a group.

  Examples of the “C1-C6 haloalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 1,3 -Difluoro-2-propyl, 1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,2,2-trifluoro Ethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 3,3,3-trifluoro-n-propyl, 4,4,4-trifluoro-n-butyl, 1,1 , 1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 1,1,1,3,3,3 -Hexafluoro 2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-2-bromo- n-propyl, 1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, 3,3,4, 4,4-pentafluoro-2-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 3-fluoro-n-propyl, 3- A linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms, which may be the same or different, such as chloro-n-propyl and 3-bromo-n-propyl; Show.

  The “C2-C4 alkenyl group” refers to an alkenyl group having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, and 3-butenyl.

  The “C2-C6 alkenyl group” refers to an alkenyl group having 2 to 6 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, and 3-butenyl.

  Examples of the “C2-C4 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2- A double bond in the carbon chain substituted by one or more halogen atoms, which may be the same or different, such as propenyl, 4,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc. And a linear or branched alkenyl group having 2 to 4 carbon atoms.

  Examples of the “C2-C6 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2- Double bonds in carbon chains substituted by one or more halogen atoms, which may be the same or different, such as propenyl, 4,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc. And a linear or branched alkenyl group having 2 to 6 carbon atoms.

The “C2-C4 alkynyl group” is, for example, a linear or branched alkynyl group having 2 to 4 carbon atoms having a triple bond in a carbon chain such as propargyl or 1-butyn-3-yl. Show.
The “C2-C6 alkynyl group” means, for example, 2 to 6 carbon atoms having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc. Represents an alkynyl group.

  The “C2-C4 haloalkynyl group” means, for example, a linear or branched carbon atom having a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different. Four alkynyl groups are shown.

  The “C2-C6 haloalkynyl group” means, for example, a linear or branched carbon atom having a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. 6 alkenyl groups are shown.

  “C3-C8 cycloalkyl group” means, for example, a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl and the like. And a cycloalkyl group having 3 to 8 carbon atoms.

  “C3-C8 halocycloalkyl group” means, 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. A cycloalkyl group having 3 to 8 carbon atoms having a substituted cyclic structure is shown.

  The “C1-C3 alkoxy group” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy and the like.

  The “C1-C4 alkoxy group” is, for example, a linear or branched carbon atom such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, i-butyloxy, s-butyloxy, t-butyloxy, etc. A several 1-4 alkoxy group is shown.

  “C1-C6 alkoxy group” means, for example, a linear or branched carbon atom such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy and the like A 1-6 alkoxy group is shown.

  Examples of the “C1-C3 haloalkoxy group” include trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy. , 3-fluoro-n-propyloxy or the like, a linear or branched alkoxy group having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different.

  Examples of the “C1-C4 haloalkoxy group” include trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy. , 3-fluoro-n-propyloxy, 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy and the like, which may be substituted by one or more halogen atoms which may be the same or different Or a linear or branched alkoxy group having 1 to 4 carbon atoms.

  Examples of the “C1-C6 haloalkoxy group” include trifluoromethoxy, pentafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, heptafluoro-n-propyloxy, heptafluoro-i-propyloxy, 1, 1,2,3,3,3-hexafluoro-n-propyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2- A linear or branched haloalkoxy group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as chloroethoxy and 3-fluoro-n-propyloxy Show.

  The “C1-C3 alkylthio group” refers to a linear or branched alkylthio group having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like.

  Examples of the “C1-C4 alkylthio group” include linear chains such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio and the like. Or a branched alkylthio group having 1 to 4 carbon atoms.

  The “C1-C6 alkylthio group” is, for example, a linear or branched carbon atom number of 1 to 6 such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, t-butylthio and the like. Represents an alkylthio group.

  The “C1-C3 haloalkylthio group” is the same or different, for example, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, etc. A linear or branched alkylthio group having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be present.

  Examples of the “C1-C4 haloalkylthio group” include trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n- Linear or branched carbon atoms substituted by one or more halogen atoms, which may be the same or different, such as butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio, etc. 1-4 alkylthio groups are shown.

  Examples of the “C1-C6 haloalkylthio group” include trifluoromethylthio, pentafluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n—. 1 which may be the same or different, such as propylthio, heptafluoro-i-propylthio, 1,1,2,3,3,3-hexafluoro-n-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio A linear or branched alkylthio group having 1 to 6 carbon atoms substituted with the above halogen atom is shown.

  The “C1-C3 alkylsulfinyl group” is, for example, a linear or branched alkyl having 1 to 3 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like. A sulfinyl group;

  “C1-C4 alkylsulfinyl group” means, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl, t-butyl A linear or branched alkylsulfinyl group having 1 to 4 carbon atoms such as sulfinyl and cyclobutylsulfinyl is shown.

  “C1-C6 alkylsulfinyl group” means, for example, linear or branched chain such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, etc. An alkylsulfinyl group having 1 to 6 carbon atoms.

  Examples of the “C1-C3 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl and the like. A linear or branched alkylsulfinyl group having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different.

  Examples of the “C1-C4 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro A linear or branched alkylsulfinyl group having 1 to 4 carbon atoms substituted by one or more halogen atoms which may be the same or different, such as n-butylsulfinyl and nonafluoro-s-butylsulfinyl Indicates.

  Examples of the “C1-C6 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n. Identical or different such as -propylsulfinyl, heptafluoro-i-propylsulfinyl, 1,1,2,3,3,3-hexafluoro-n-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl Or a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, which may be substituted with one or more halogen atoms.

  The “C1-C3 alkylsulfonyl group” means, for example, a linear or branched carbon atom number 1 to 1 such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl, cyclopropylsulfonyl and the like. 3 alkylsulfonyl groups are shown.

  “C1-C4 alkylsulfonyl group” means, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, t-butyl A linear or branched alkylsulfonyl group having 1 to 4 carbon atoms such as sulfonyl and cyclopropylsulfonyl is shown.

  The “C1-C6 alkylsulfonyl group” is, for example, a linear or branched chain such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, etc. An alkylsulfonyl group having 1 to 6 carbon atoms.

  Examples of the “C1-C3 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl and the like. A linear or branched alkylsulfonyl group having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different.

  “C1-C4 haloalkylsulfonyl group” means, for example, trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro A linear or branched alkylsulfonyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as n-butylsulfonyl and nonafluoro-s-butylsulfonyl Indicates.

  Examples of the “C1-C6 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n. -Propylsulfonyl, 1,1,2,3,3,3-hexafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl and the like or different And a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms.

  The “C1-C4 alkylcarbonyl group” refers to a linear, branched or cyclic alkylcarbonyl group having 1 to 4 carbon atoms such as acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like.

  The “C1-C4 haloalkylcarbonyl group” is substituted with one or more halogen atoms which may be the same or different, such as trifluoroacetyl, pentafluoropropionyl, trichloroacetyl, chloroacetyl, bromoacetyl, 3-chloropropionyl, etc. Represents a linear or branched alkylcarbonyl group having 1 to 4 carbon atoms.

  The “C1-C4 alkylcarbonyloxy group” refers to a linear or branched alkylcarbonyloxy group having 1 to 4 carbon atoms such as acetoxy and propionyloxy.

  The “C1-C4 alkoxycarbonyl group” is, for example, a linear or branched alkoxycarbonyl group having 1 to 4 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl or the like.

  The “C1-C4 alkylene group” refers to a linear or branched alkylene group having 1 to 4 carbon atoms such as methylene, ethylene, propylene, dimethylmethylene, isobutylene and the like.

  The “C2-C4 alkenylene group” refers to, for example, a linear or branched alkenylene group having 2 to 4 carbon atoms having a double bond in the carbon chain.

  The “C2-C4 alkynylene group” refers to, for example, a linear or branched alkynylene group having 2 to 4 carbon atoms having a triple bond in the carbon chain.

  The “C1-C4 haloalkylene group” is, for example, a linear or branched chain substituted with one or more halogen atoms which may be the same or different, such as chloromethylene, chloroethylene, dichloromethylene, difluoromethylene and the like. An alkylene group having 1 to 4 carbon atoms is shown.

  “C2-C4 haloalkenylene group” means, for example, the number of linear or branched carbon atoms having a double bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. 2 to 4 alkynylene groups are shown.

  The “C2-C4 haloalkynylene group” is, for example, a linear or branched carbon atom having 2 to 3 carbon atoms having a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. Four alkynylene groups are shown.

  Examples of the “C1-C6 haloalkylsulfonyloxy group” include trifluoromethylsulfonyloxy, pentafluoroethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy, heptafluoro-n-propylsulfonyloxy, heptafluoro-i. Linear or branched carbon atoms substituted by one or more halogen atoms which may be the same or different, such as -propylsulfonyloxy, nonafluoro-n-butylsulfonyloxy, nonafluoro-s-butylsulfonyloxy 1-4 alkylsulfonyloxy groups are shown.

  The “C1-C4 haloalkoxycarbonyl group” may be the same or different, for example, chloromethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 3,3,3-trichloro-n-propyloxycarbonyl, etc. A linear or branched haloalkoxycarbonyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms is shown.

  The “C2-C4 alkenyloxycarbonyl group” means, for example, a carbon atom having a double bond in a carbon chain such as vinyloxycarbonyl, allyloxycarbonyl, 2-butenyloxycarbonyl, 3-butenyloxycarbonyl, etc. -4 alkenyloxycarbonyl groups are shown.

  The “C2-C4 alkynyloxycarbonyl group” means, for example, a linear or branched carbon atom number 2 having a triple bond in a carbon chain such as propargyloxycarbonyl, 1-butyn-3-yl-oxycarbonyl, etc. -4 alkynyloxycarbonyl groups are shown.

  “C1-C4 alkylaminocarbonyl group” means, for example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, i-propylaminocarbonyl, cyclopropylaminocarbonyl, n-butylaminocarbonyl, s-butylaminocarbonyl, A linear or branched alkylaminocarbonyl group having 1 to 4 carbon atoms such as i-butylaminocarbonyl and t-butylaminocarbonyl is shown.

  Examples of the “C1-C4 haloalkylaminocarbonyl group” include trifluoromethylaminocarbonyl, pentafluoroethylaminocarbonyl, heptafluoro-n-propylaminocarbonyl, heptafluoro-i-propylaminocarbonyl, 2,2-difluoroethylamino. Carbonyl, 2,2-dichloroethylaminocarbonyl, 1,3-difluoro-2-propylaminocarbonyl, 1,3-dichloro-2-propylaminocarbonyl, 1-chloro-3-fluoro-2-propylaminocarbonyl, 1 , 1,1-trifluoro-2-propyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,2-trichloroethylaminocarbonyl, 2,2,2-tribromoethylaminocarbonyl, 3,3 , 3-Trifluoro-n Propylaminocarbonyl, 4,4,4-trifluoro-n-butylaminocarbonyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3- Hexafluoro-2-chloro-2-propylaminocarbonyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propylaminocarbonyl, 1,1,2,3,3,3- Hexafluoro-2-chloro-n-propylaminocarbonyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propylaminocarbonyl, 1,1,2,3,3,3- Hexafluoro-1-bromo-2-propylaminocarbonyl, 2,2,3,3,3-pentafluoro-n-propylaminocarbonyl, 3,3,4,4,4-pentafluoro-2-butylaminocarbonyl Bonyl, nonafluoro-n-butylaminocarbonyl, nonafluoro-2-butylaminocarbonyl, 2-fluoroethylaminocarbonyl, 2-chloroethylaminocarbonyl, 2-bromoethylaminocarbonyl, 2-iodoethylaminocarbonyl, 3-fluoro- linear or branched chain substituted by one or more halogen atoms which may be the same or different, such as n-propylaminocarbonyl, 3-chloro-n-propylaminocarbonyl, 3-bromo-n-propylaminocarbonyl, etc. An alkylaminocarbonyl group having 1 to 4 carbon atoms.

  Examples of the “C1-C4 haloalkylcarbonyloxy group” include trifluoromethylcarbonyloxy, pentafluoroethylcarbonyloxy, heptafluoro-n-propylcarbonyloxy, heptafluoro-i-propylcarbonyloxy, 2,2-difluoroethylcarbonyl Oxy, 2,2-dichloroethylcarbonyloxy, 1,3-difluoro-2-propylcarbonyloxy, 1,3-dichloro-2-propylcarbonyloxy, 1-chloro-3-fluoro-2-propylcarbonyloxy, 1 , 1,1-trifluoro-2-propylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, 2,2,2-tribromoethylcarbonyloxy, 3, , 3,3- Lifluoro-n-propylcarbonyloxy, 4,4,4-trifluoro-n-butylcarbonyloxy, 1,1,1,3,3,3-hexafluoro-2-propylcarbonyloxy, 1,1,1, 3,3,3-hexafluoro-2-chloro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propylcarbonyloxy, 1,1,2,3 3,3-hexafluoro-2-chloro-n-propylcarbonyloxy, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propylcarbonyloxy, 1,1,2,3 3,3-hexafluoro-1-bromo-2-propylcarbonyloxy, 2,2,3,3,3-pentafluoro-n-propylcarbonyloxy, 3,3,4,4,4-pentafluoro-2 Butylcarbonyloxy, nonafluoro-n-butylcarbonyloxy, nonafluoro-2-butylcarbonyloxy, 2-fluoroethyl, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 3-fluoro- Linear or branched chain substituted by one or more halogen atoms which may be the same or different, such as n-propylcarbonyloxy, 3-chloro-n-propylcarbonyloxy, 3-bromo-n-propylcarbonyloxy An alkylcarbonyloxy group having 1 to 4 carbon atoms.

  Examples of the “C1-C4 alkoxy C1-C4 alkyl group” include methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, n-butyloxymethyl, i-butyloxymethyl, s-butyloxymethyl, t -Butyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, n-butyloxyethyl, i-butyloxyethyl, s-butyloxyethyl, t-butyloxyethyl, methoxy n-propyl, Linear chain such as ethoxy n-propyl, n-propyloxy n-propyl, isopropyloxy n-propyl, n-butyloxy n-propyl, i-butyloxy n-propyl, s-butyloxy n-propyl, t-butyloxy n-propyl Or branched carbon source The number indicates the 1-4 C1-C4 alkoxy C1-C4 alkyl group.

  Examples of the “C1-C4 haloalkoxy C1-C4 alkyl group” include trifluoromethoxymethyl, pentafluoroethoxymethyl, 1,1,2,2-tetrafluoroethoxymethyl, heptafluoro-n-propyloxymethyl, heptafluoro -I-propyloxymethyl, 1,1,2,3,3,3-hexafluoro-n-propyloxymethyl, 1,1,1,3,3,3-hexafluoro-2-propyloxymethyl, 2 2,2-trifluoroethoxymethyl, 2-chloroethoxymethyl, 3-fluoro-n-propyloxymethyl, trifluoromethoxyethyl, pentafluoroethoxyethyl, 1,1,2,2-tetrafluoroethoxyethyl, hepta Fluoro-n-propyloxyethyl, heptafluoro-i-propyloxy Chill, 1,1,2,3,3,3-hexafluoro-n-propyloxyethyl, 1,1,1,3,3,3-hexafluoro-2-propyloxyethyl, 2,2,2- Trifluoroethoxyethyl, 2-chloroethoxyethyl, 3-fluoro-n-propyloxyethyl, trifluoromethoxy n-propyl, pentafluoroethoxy n-propyl, 1,1,2,2-tetrafluoroethoxy n-propyl, Heptafluoro-n-propyloxy n-propyl, heptafluoro-i-propyloxy n-propyl, 1,1,2,3,3,3-hexafluoro-n-propyloxy n-propyl, 1,1,1 , 3,3,3-hexafluoro-2-propyloxy n-propyl, 2,2,2-trifluoroethoxy n-propyl, 2-chloroe 1 to 4 linear or branched carbon atoms substituted with one or more halogen atoms which may be the same or different, such as xyl-n-propyl, 3-fluoro-n-propyloxy n-propyl The haloalkoxy C1-C4 alkyl group of is shown.

  The compound represented by the general formula (1) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in the structural formula, and two or more optical isomers exist. In some cases, the present invention includes all of the optical isomers and mixtures containing them in an arbitrary ratio. In addition, the compound represented by the general formula (1) of the present invention may have two or more geometric isomers derived from a carbon-carbon double bond in the structural formula thereof. All geometric isomers and mixtures containing them in an arbitrary ratio are also included.

  Preferred substituents or atoms among the substituents in the compound represented by the general formula represented by the general formula (1) of the present invention are as follows.

G ₁ , G ₂ and G ₃ are preferably oxygen atoms.
Het is preferably a furyl group, a thienyl group, a thiazolyl group, or a pyrrolyl group.

As a preferred combination of A, E, and D, when any one of A, E, and D is a nitrogen atom, an oxygen atom, and a sulfur atom, the other two are carbon atoms, and any two of A, E, and D are When each of them is a nitrogen atom and an oxygen atom, the remaining one is a carbon atom, and particularly preferred combinations are E and D are carbon atoms, A is a sulfur atom, A and D are carbon atoms, E is an oxygen atom, E, A is a carbon atom, D is a nitrogen atom, E is a nitrogen atom, A is a sulfur atom, and D is a carbon atom.
X is preferably a hydrogen atom, a halogen atom, or a C1-C3 alkyl group, and more preferably a hydrogen atom, a fluorine atom, or a methyl group.
n is preferably 0, 1, or 2, and more preferably 0 or 1.

Q ₁ is preferably a phenyl group, or 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-C8 cycloalkyl group, C3-C8 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, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl Group, C1-C4 alkylcarbo A substituted phenyl group having one or more substituents which may be the same or different, selected from a nyloxy group, a C1-C4 alkoxycarbonyl group, and an acetylamino group;
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-C8 cyclo Alkyl group, C3-C8 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, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkyl Carbonyloxy group, C1-C Alkoxycarbonyl group, a pyridyl group having one or more same or different and have good substituents selected from acetylamino group,
More preferably,
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;
Pyridyl 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, It is a pyridyl group having 1 to 2 substituents which may be the same or different and selected from a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group.

Q ₂ is preferably a phenyl group which may be substituted or a heterocyclic group which may be substituted, and more preferably a substituted phenyl group represented by the general formula (3) or the general formula (4) or A substituted pyridyl group,
inside that,
Y ₁ and Y ₅ are preferably a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a methoxy group, and a tri group, respectively. A fluoromethoxy group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a cyano group,
Y ₆ and Y ₉ are chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-butyl group, methoxy group, trifluoromethoxy, respectively. Group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyano group,
Y ₂ , Y ₄ and Y ₇ are preferably a hydrogen atom, a halogen atom and a methyl group, more preferably a hydrogen atom,
Y _{3 and} Y ₈ are preferably trifluoromethyl group, pentafluoroethyl group, heptafluoro-n-propyl group, heptafluoro-i-propyl group, 1,1,1,3,3,3-hexafluoro- 2-chloro-2-propyl group, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl group, 1,1,2,3,3,3-hexafluoro-2- Chloro-n-propyl group, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl group, 1,1,2,3,3,3-hexafluoro-1-bromo- 2-propyl group, nonafluoro-n-butyl group, nonafluoro-2-butyl group, nonafluoro-i-butyl group,
Trifluoromethoxy group, pentafluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 1,1,1,3,3,3-hexafluoro-i-propyloxy group, heptafluoro-n-propyl Oxy group, heptafluoro-i-propyloxy group, 1,1,2,3,3,3-hexafluoro-n-propyloxy group, nonafluoro-2-butyloxy group, trifluoromethylthio group, pentafluoroethylthio group 1,1,2,2-tetrafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, 1,1,2,3,3,3-hexafluoro-n-propylthio group , Nonafluoro-n-butylthio group, nonafluoro-2-butylthio group, trifluoromethylsulfinyl group, pentafluoro Ethylsulfinyl group, 1,1,2,2-tetrafluoroethylsulfinyl group, heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, 1,1,2,3,3,3-hexafluoro -N-propylsulfinyl group, nonafluoro-n-butylsulfinyl group, nonafluoro-2-butylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, hepta Fluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, 1,1,2,3,3,3-hexafluoro-n-propylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2- A butylsulfonyl group, and Preferably, heptafluoro-i-propyl group, nonafluoro-2-butyl group, 1,1,2,3,3,3-hexafluoro-n-propyloxy group, 1,1,2,3,3, 3-hexafluoro-n-propylthio group, 1,1,2,3,3,3-hexafluoro-n-propylsulfinyl group, 1,1,2,3,3,3-hexafluoro-n-propylsulfonyl group It is a group.

R ₁ and R ₂ are preferably a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, an optionally substituted C2-C4 unsaturated alkyl group, or a substituted one. C1-C4 alkoxycarbonyl group, substituted C1-C4 alkyl group or C (═O) C (═O) R ₄ (wherein R ₄ may be an optionally substituted alkyl group or may be substituted) A good C1-C4 alkoxy group), and more preferably a hydrogen atom, a methyl group, an ethyl group, or an acetyl group.

R ₃ is preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group. , C3-C8 halocycloalkyl _group, -E 1 _-Z 1 -R ₄ (wherein, _{E 1} is C1-C4 alkylene group, C2-C4 alkenylene group, C2-C4 alkynylene group, C1-C4 haloalkylene group, A C2-C4 haloalkenylene group and a C3-C4 haloalkynylene group, wherein R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group. group, a C2-C6 haloalkynyl group, _{Z 1} is -O -, - S -, - SO -, - shows a - SO ₂ ), _- E 2 -R ₆ (wherein, _{E 2} is C1-C4 alkyl group, C2-C4 alkenyl group, C3-C4 alkynyl group, C1-C4 haloalkyl group, C2-C4 haloalkenyl group, C2-C4 halo An alkynyl group, wherein R ₆ is a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, or the same or different, a halogen atom, C1-C6 Alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1 -C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, A substituted phenyl group having one or more substituents selected from a R group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, pyridyl group or a halogen atom,, C1-C6 haloalkyl group, a.) indicating a substituent pyridyl group having one or more substituents selected from C1-C6 haloalkoxy group, preferably a more R _3, C1 -C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl, C3-C8 halocycloalkyl _group, -E 1 _-Z 1 -R ₄ (wherein, _{E 1} is C1-C4 alkylene group, C1- shows the C4 haloalkylene group, _{R 4} represents a C1-C6 alkyl group, _{Z 1} is -O -, - S -, - SO , -SO ₂ - shows the. ), _- E 2 -R ₆ (wherein,
E ₂ represents a C1-C4 alkyl group, R ₆ may be a C3-C8 cycloalkyl group, a cyano group, which may be the same or different, a halogen atom, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1- C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, substituted phenyl group having one or more substituents selected from cyano group, nitro group, pyridyl group, halogen atom, C1-C6 haloalkyl group , A substituted pyridyl group having one or more substituents selected from a C1-C6 haloalkoxy group, a thienyl group, and a tetrahydrofuryl group. ).
The compound represented by the general formula (1) can be produced by the production methods 1 to 10 described below. Although the typical manufacturing method of the compound of this invention is shown below and the manufacturing of the compound of this invention is possible by following it, a manufacturing method path | route is not limited to the manufacturing method shown below.
Manufacturing method 1

(In the formula, Het, G ₃ , R ₁ , R ₂ , X, n, Q ₂ and Z are the same as those in [1], and L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group. To express.)

1- (i): General formula (5) + General formula (6) → General formula (7)
By reacting the nitro group represented by the general formula (5) and the 5-membered heterocyclic derivative having a leaving group with the aromatic amine derivative represented by the general formula (6) in a solvent or without solvent, A 5-membered heterocyclic carboxylic acid amide derivative having a nitro group represented by the general formula (7) can be produced. In this step, a base can also 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 5 molar equivalents relative to the compound represented by the general formula (5).

  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.

  Among the compounds represented by the general formula (5), a 5-membered heterocyclic carboxylic acid halide derivative can be easily produced from a 5-membered heterocyclic carboxylic acid by a conventional method using a halogenating agent. Can do. Examples of the halogenating agent include halogenating agents such as thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride.

  On the other hand, it is possible to produce the compound represented by the general formula (7) from the 5-membered heterocyclic carboxylic acid and the compound represented by the general formula (6) without using a halogenating agent. As a method, for example, Chem. Ber. p. By following the method described in 788 (1970), a method using an additive such as 1-hydroxybenzotriazole and using a condensing agent using N, N'-dicyclohexylcarbodiimide can be shown. 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 (7), a mixed acid anhydride method using chloroformates can be shown. Am. Chem. Soc. p. By following the method described in 5012 (1967), the compound represented by the general formula (7) 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 (7) → General formula (8)
A 5-membered heterocyclic carboxylic acid amide derivative having a nitro group represented by the general formula (7) is converted into a 5-membered heterocyclic carboxylic acid having an amino group represented by the general formula (8) by a reduction reaction. Can lead to amide derivatives. 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, under normal pressure or under pressure, and in a hydrogen atmosphere. Examples of the catalyst include a palladium catalyst such as palladium-carbon, a nickel catalyst such as Raney nickel, a cobalt catalyst, a ruthenium catalyst, a rhodium catalyst, a platinum catalyst, and the like. Examples of the solvent include water, alcohols such as methanol and ethanol, benzene, Aromatic hydrocarbons such as toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate can be used. 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 (8) 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 (8) + General formula (9) → General formula (10)
By reacting the 5-membered heterocyclic carboxylic acid amide derivative represented by the general formula (8) with the compound represented by the general formula (9) in a solvent, the present invention represented by the general formula (10) Compounds can be produced. In this step, a base can also 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 5 molar equivalents relative to the compound represented by the general formula (8). 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 the method using the condensing agent described in 1- (i) or the mixed acid anhydride method.

1- (iv): General formula (10) + General formula (11) → General formula (1)
By reacting the compound represented by the general formula (10) and the compound having a leaving group represented by the general formula (11) in a solvent or without a solvent, the present invention represented by the general formula (1) Compounds can be produced. Examples of the compound represented by the general formula (11) include substituted alkyl halides such as methyl iodide, ethyl iodide, n-propyl bromide, and chloromethyl methyl ether, and carboxylic acids such as acetyl chloride, chloroacetyl chloride, and benzoyl chloride. Unsaturated alkyl halides such as acid halides, propargyl bromide, chloroformates such as methyl chloroformate, 2-chloroethyl chloroformate, phenyl chloroformate and benzyl chloroformate, and carbamate halides such as N, N-dimethylcarbamoyl chloride Sulfonic acid halides such as methanesulfonyl chloride, trifluoromethanesulfonyl chloride, tosylic acid chloride, chloroglyoxylic acid esters such as methyl chloroglyoxylate and ethyl chloroglyoxylate, chlorotrimethylsilane Alternatively, tert-butylchlorodimethylsilane and the like can be exemplified. In this step, an appropriate base or solvent can be used. As the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).

Alternatively, instead of the compound represented by the general formula (11), an alkylating agent such as dimethyl sulfate or diethyl sulfate can be reacted with the compound represented by the general formula (10). It is possible to produce the compound represented by 1).
Manufacturing method 2

(In the formula, Het, G ₃ , R ₁ , R ₂ , X, n, Q ₂ and Z are the same as those 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 halogen atom.)

2- (i): General formula (12) + General formula (9) → General formula (13)
By using a carboxylic acid having an amino group represented by the general formula (12) as a starting material and reacting with a compound represented by the general formula (9) according to the conditions described in 1- (iii), the general formula (9) 14) can be produced.

2- (ii): General formula (13) → General formula (14)
The compound represented by the general formula (13) is reacted with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride and the like. The compound represented by the general formula (14) can be produced by a known ordinary method.

2- (iii): General formula (14) + General formula (6) → General formula (1)
By reacting the compound represented by the general formula (15) and the compound represented by the general formula (6) according to the conditions described in 1- (i), the compound represented by the general formula (16) is obtained. Can be manufactured.

2- (iv): General formula (14) + General formula (6) → General formula (16)
The compound represented by the general formula (14) is reacted with the compound represented by the general formula (6) according to the conditions using the condensing agent described in 1- (i) or the conditions using the mixed acid anhydride method. Thus, the compound represented by the general formula (1) can be produced.
Manufacturing method 3

(In the formula, Het, R ₁ , R ₂ , X, n, Q ₂ and Z are the same as those in [1], and L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group.)

3- (i): General formula (15) → General formula (16)
Synthesis p. 463 (1993) and Synthesis p. The compound represented by the general formula (16) can be produced by reacting the compound represented by the general formula (15) with a Lawson reagent according to known conditions described in 829 (1984) and the like. Conditions such as solvent and reaction temperature are not limited to those described in the literature.

3- (ii): General formula (16) + General formula (9) → General formula (17)
By reacting the compound represented by the general formula (16) with the compound represented by the general formula (9) according to the conditions described in 1- (iii), the compound represented by the general formula (17) Can be manufactured.
Manufacturing method 4

(In the formula, E represents -Q ₁ or G ₂ R ₃ , and Het, R ₁ , R ₂ , R ₃ , X, n, Q ₁ , and Q ₂ represent the same as [1].)
From the compound represented by the general formula (18), the compound represented by the general formula (19) and the general formula (20) can be produced according to the conditions described in 3- (i). Conditions such as solvent and reaction temperature are not limited to those described in the literature. These two compounds can be separated and purified by a known separation and purification technique such as silica gel column chromatography.
Manufacturing method 5

(In the formula, Het, G ₃ , R ₁ , R ₂ , X, n, Q ₂ and Z are the same as those in [1], and L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group. To express.)

5- (i): General formula (21) → General formula (22)
The compound represented by the general formula (22) can be synthesized by diazotizing the compound represented by the general formula (21) and reacting a diazonium salt with a metal salt.

  The solvent used in both the reaction of diazotization and the reaction of a diazonium salt and a metal salt may be any solvent that does not significantly inhibit the progress of this reaction. For example, hydrochloric acid water, hydrobromic acid water, hydroiodic acid water , Acidic solvents such as sulfuric acid and trifluoroacetic acid, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, diethyl ether, dioxane, tetrahydrofuran, 1, 2 -Linear or cyclic ethers such as 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 can show inert solvent such non These solvents may be used alone or as a mixture of two or more. Examples of the diazotizing agent include diazotizing agents such as sodium nitrite, nitrosyl hydrogen sulfate, and alkyl nitrite. The amount of these used is 0 with respect to the compound represented by the general formula (23c). .5 to 50 equivalents may be selected as appropriate. The reaction temperature of diazotization can be carried out from −50 ° C. to the reflux temperature of the reaction solvent, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours.

As the metal salt to be added after the diazonium salt is formed, a metal salt such as cuprous chloride, cupric chloride, cuprous bromide, cupric bromide, potassium iodide can be used, and its use The amount may be appropriately selected from 0.5 to 50 equivalents relative to the compound represented by the general formula (21). The reaction temperature can be carried out from −50 ° C. to the reflux temperature of the reaction solvent, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours.
It is also possible to react by simultaneously adding a diazotizing agent, a metal salt and a solvent.

5- (ii): General formula (22) → General formula (23)
The compound represented by the general formula (22) is reacted with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride and the like. The compound represented by the general formula (23) can be produced by a known ordinary method.

5- (iii): General formula (23) → General formula (24)
By reacting the compound represented by the general formula (23) and the compound represented by the general formula (6) according to the conditions described in 1- (i), the compound represented by the general formula (24) is obtained. Can be manufactured.

5- (IV): General formula (24) → General formula (25)
For example, J. et al. Org. Chem. p. 280 (1958), it is possible to produce a compound represented by the general formula (25) by carrying out an amination reaction using ammonia. It is not limited to those described, and an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate, and the reaction temperature and the reaction time may be appropriately selected according to the progress of the reaction. Moreover, as an aminating agent, methylamine, ethylamine, hydroxylamine, O-methylhydroxylamine, etc. can be shown besides ammonia.

5- (V): General formula (25) + General formula (9) → General formula (1)
By reacting the compound represented by the general formula (25) and the compound represented by the general formula (9) according to the conditions described in 1- (iii), the compound represented by the general formula (1) Can be manufactured.
Manufacturing method 6

(In the formula, Het, X, n, G ₃ , R ₂ and Q ₂ are the same as those in [1], and M represents a nitro group or a halogen atom.)
The compound represented by the general formula (26) can be produced by reacting the compound represented by the general formula (26) with a reactant in a solvent using a base.

  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, Nitriles such as propionitrile, 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, dimethyl sulfoxide, can indicate a solvent such as water, 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 hydrogen carbonate 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 or used as a solvent in the range of 0.01 to 5 molar equivalents relative to the compound represented by the general formula (26).

  Examples of the reactive agent include substituted alkyl halides such as methyl iodide, ethyl iodide, n-propyl bromide, chloromethyl methyl ether, carboxylic acid halides such as acetyl chloride, chloroacetyl chloride, and benzoyl chloride, propargyl bromide Unsaturated alkyl halides such as methyl chloroformate, 2-chloroethyl chloroformate, phenyl chloroformate, chloroformates such as benzyl chloroformate, carbamic acid halides such as N, N-dimethylcarbamoyl chloride, methanesulfonyl chloride, Sulfonic acid halides such as trifluoromethanesulfonyl chloride and tosylic acid chloride, chloroglyoxylic acid esters such as methyl chloroglyoxylate and ethyl chloroglyoxylate, chlorotrimethylsilane or tert And the like can be exemplified butylchlorodimethylsilane.

  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 (26).

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 7

(In the formula, Het, X, n, G ₃ , R ₁ , R ₂ and Q ₂ are the same as those in [1].)

7- (i): General formula (8) → General formula (28)
The compound represented by the general formula (8) is reacted with an aldehyde or a ketone in a solvent, a catalyst is added, and the reaction is performed in a hydrogen atmosphere to produce the compound represented by the general formula (28). 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, Nitriles such as propionitrile, 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 and palladium hydroxide-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 1 to 100 atm.

  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.

7- (ii): General formula (8) → General formula (28) (Alternative method 1)
The compound represented by general formula (50) can be produced by reacting the compound represented by general formula (22) with an aldehyde or ketone in a solvent and treating the reducing agent.

  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, Nitriles such as propionitrile, 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 triacetate borohydride.

  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.

7- (iii): General formula (8)-> General formula (28) (alternative method 2)
By reacting the compound represented by the general formula (22) with a formylating agent in a solvent or without a solvent and treating the additive, a compound in which R ₁ is a methyl group in the general formula (28) is produced. can do.

  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, Nitriles such as propionitrile, 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, oxazole and the like. 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 to be used, and the reaction time may be appropriately selected within the range of several minutes to 96 hours.
Manufacturing method 8

(In the formula, Het, G ₃ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are the same as [1], and Hal is a halogen atom.)

8- (i): General formula (8) + General formula (29) → General formula (30)
Tetrahedron Lett. p. In accordance with known conditions described in 3789 (1999), the compound represented by the general formula (8) is reacted with the compound represented by the general formula (29). Compounds can be produced. Conditions such as solvent and reaction temperature are not limited to those described in the literature.

8- (ii): General formula (30) + General formula (11) → General formula (31)
By reacting the compound represented by the general formula (30) and the compound represented by the general formula (11) according to the conditions described in 1- (iv), the compound represented by the general formula (31) is obtained. Can be manufactured.
Manufacturing method 9

(In the formula, Het, G ₃ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are the same as [1], and Hal is a halogen atom.)
9- (i): General formula (32) → General formula (33)
By reacting the compound represented by the general formula (33) according to the conditions described in 2- (ii), the compound represented by the general formula (33) can be produced.

9- (ii): General formula (33) + General formula (6) → General formula (34)
By reacting the compound represented by the general formula (33) and the compound represented by the general formula (6) according to the conditions described in 1- (i), the compound represented by the general formula (34) is obtained. Can be manufactured.

9- (iii): General formula (32) + General formula (6)-> General formula (34)
The compound represented by the general formula (34) is reacted with the compound represented by the general formula (6) according to the conditions using the condensing agent described in 1- (i) or the conditions using the mixed acid anhydride method. Thus, the compound represented by the general formula (34) can be produced.
Manufacturing method 10

(In the formula, Het, G ₃ , R ₁ , R ₂ , X, n, Q ₂ and Z are the same as those in [1].)
By reacting the compound represented by the general formula (35) according to the conditions described in 1- (iv), the compound represented by the general formula (1) can be produced.

Also, Journal of Chemical Society Chemical Communications p. 270 (1988) and the like, by reacting the compound represented by the general formula (35) with nitronium tetrafluoroborate, R ₁ or R ₂ in the general formula (1) is a nitroso group. The compound which is: Synthesis-Stuttgart p. The compound represented by general formula (35) is reacted with ammonium nitrate according to known conditions described in 745 (1988) and the like to produce a compound in which R ₁ or R ₂ in general formula (1) is a nitro group can do. Conditions such as solvent and reaction temperature are not limited to those described in the literature.
Heterocycles p. 159 (1988) and the like, by reacting the compound represented by the general formula (35) with N-chlorosuccinimide or N-bromosuccinimide, R in the general formula (1) _A compound in which ₁ or R ₂ is a chlorine atom or a bromine atom can be produced.

  In all the production methods shown above, the target product may be isolated from the reaction system according to a conventional method after completion of the reaction. If necessary, it can be purified by recrystallization, column chromatography, distillation or the like. can do. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

  Hereinafter, Tables 1 to 30 show typical compounds represented by the general formula (1) which are active ingredients of the insecticide of the present invention, but the present invention is not limited thereto. .

In the table, “n-” represents normal, “Me” represents a methyl group, “Et” represents an ethyl group, “n-Pr” represents a normal propyl group, “i-Pr” represents an 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” represents an oxygen atom, “S” represents a sulfur atom, “C” represents a carbon atom, “N” represents a nitrogen atom, “F” represents a fluorine atom, “Cl” represents a chlorine atom, “Br” is a bromine atom, “I” is an iodine atom, “CF ₃ ” is a trifluoromethyl group, “MeS” is a methylthio group, “MeSO” is a methylsulfinyl group, and “MeSO ₂ ” is methyl. sulfonyl group, "MeO" a methoxy group, an "NH _2" is an amino group The "MeNH" represents a methyl group, "Me 2 _N" is a dimethylamino group, "OH" is a hydroxy group, and represents respectively.

Table 31 shows the physical property values of the compounds of the present invention. Unless otherwise indicated, the shift value of ¹ H-NMR shown here uses tetramethylsilane as an internal reference substance, and “J” indicates a binding constant.

  The insecticide containing the compound represented by the general formula (1) of the present invention as an active ingredient is a variety of agricultural, forestry, horticultural, stored grain pests, sanitary pests or nematodes that harms paddy rice, fruit trees, vegetables, other crops, flowers, etc. It is suitable for pest control such as, and has an insecticidal effect against these pests. Examples of such pests include the following. Urophore (Diaphania indica), Chamonaki (Homona magnanima), Hyellulla undalis, Adoxophyes orana fasciata, Adoxophyes sp., Adoxophyes sp. (Carposina niponensis), Apple cinchoi (Grapholita inopinata), Pepper moth (Op) , Appleoptia zachrysa, Phyllonorycter ringoniella, Spulerrina astaurota, Swallowtail butterfly (Papilio xuthus), Pieris rapae crucivora, Heliothis armigmon a xylostella, Argyresthia conjugella, Carposina niponensis, Chilo suppressalis, Cnaphalocrocis medinalis, Ephestia elutella, Glyphodes aga (Glyphodes aga) incertulas, Parnara guttata, Pseudaletia separata, Sesamia inferens, Mamestra brassicae, Spodoptera litura, Sguaoptagro segetum, Autographa nigrisigna, Trichoplusia ni, Lepidoptera, Macrosteles fascifrons, Nephotettix cincticeps, Nilaparvata Soga tella furcifera), citrus lice (Diaphorina citri), Aleurolobus taonabae, silver leaf white lice (Bermisia argentifolii), tobacco whitefly (Bemisia tabaci), on-site whitefly (Trialeurodes vaporarios), erysamphidia phi gossypii), snowy aphid (Aphis Citricola), peach aphid (Myzus persicae), horned beetle (Ceroplastes ceriferus), stag beetle (Pseudococcus Comstocki), stag beetle (Planococcus kraunhiae moth) Pseudaonidia duplex, Pterudaonidia duplex (Comstockaspis perniciosa), Paramecium beetle (Unaspis yanonensis), Chabaenokamushi (Plautia Stali), Hemiyomorpha mista (Haliyomorpha mista), rea Poppy japonica, Lasioderma serricorne, Lyctusbrunneus, Epilachna vigintioctopunctata, Callosobruchus chinensis, Listriseres (Anthonomus grandis grandis), rice weevil (Lissorhoptrus oryzophilus), cucumber beetle (Aulacophora femoralis), rice beetle (Oulema oryzae), horned beetle (Phyllotreta striolata), pine beetle (Tomicus piniperem) varivestis, corn root worms (Diabrotica sp.), Psacothea hilaris, Coleoptera pests such as Anoplophora malasiaca; Onion fly (Delia antiqua), fly fly (Delia platura), soybean sand fly (Asphondylia sp.), House fly (Musca domestica), winged fly (Chromatomyia horticola), bean wing fly (Liriomyza trifolii), leaf moth (Liriomyza trifolii) Diptera pests such as pipiens, Pratylenchus coffeae, Nepalese nematode (Pratylenchus sp.), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus seminymouse (pytrans) Nestled pests such as Aphelenchus avenae and Aphelenchoides ritzemabosi, Thrips palmi, Thrips palmi Thrips flavus), Negia Miuma (Thrips tabaci) Thysanoptera, such as the German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Kobaneinago (Oxya yezoensis) Orthoptera pests such as.

  The insecticide containing the compound represented by the general formula (1) of the present invention as an active ingredient is a remarkable control against the pests that damage paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers. Paddy fields such as paddy fields, fields, fruit trees, vegetables, other crops, flower buds, etc., at the time when the occurrence of pests is confirmed or when the occurrence is confirmed, in accordance with the time when the occurrence of pests is expected. The effect as an insecticide of the present invention can be obtained by treating the leaves and soil.

  In general, the insecticide of the present invention is formulated and used in a form convenient for use in accordance with a conventional formulation method for agricultural and horticultural drugs. That is, the compound represented by the general formula (1) is dissolved, separated, suspended, mixed, impregnated by mixing these in an appropriate inert carrier or in an appropriate ratio together with auxiliary agents as necessary. What is necessary is just to adsorb | suck or adhere and to formulate and use for an appropriate dosage form, for example, a suspension agent, an emulsion, a liquid agent, a wettable powder, a granule, a powder agent, a tablet.

  The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid inert carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, Tobacco stem powder, walnut shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllide) Etc.), silicas (for example, diatomaceous earth, silica sand, mica, white carbon (a synthetic high-dispersion silicic acid called hydrous finely divided silicon or hydrous silicic acid, and some products contain calcium silicate as a main component)), activated carbon, sulfur powder , Pumice, calcined diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, ammonium sulfate, phosphorous, ammonium nitrate Urea, chemical fertilizers such as salts depreciation, etc. can be mentioned compost, which are used alone or in the form of a mixture of two or more.

  The material that can be a liquid inert carrier is selected from those having solvent ability itself, and those that can disperse an active ingredient compound with the aid of an auxiliary agent without having solvent ability. As examples, the following carriers can be exemplified, but these are 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, etc.), 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, etc.), aromatic Hydrocarbons ( For example, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, etc.), esters (eg, ethyl acetate, butyl acetate, ethyl propionate, phthalic acid) Diisobutyl, dibutyl phthalate, dioctyl phthalate, etc.), amides (eg, dimethylformamide, diethylformamide, dimethylacetamide, etc.) and nitriles (eg, acetonitrile, etc.).

  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 the active ingredient compound, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene Can show surfactants such as ethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher alcohol sulfate it can.

  Further, for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and / or binding, the following exemplified adjuvants can be used, such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, Adjuvants such as polyvinyl alcohol, pine oil, coconut oil, bentonite, xanthan gum and 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 compound represented by the general formula (1) 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-methylphenol), phenol derivatives such as BHA (butylhydroxyanisole), bisphenol derivatives, arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, phenetidine and acetone condensates, or benzophenone series By adding an appropriate amount of the compounds as a stabilizer, a more stable composition can be obtained.

  The amount of the active ingredient of the compound represented by the general formula (1) of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, 10 to 90% by weight for wettable powders, and granules. 0.1 to 20% by weight and 10 to 90% by weight for flowable preparations. 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.

  Applying an effective amount for disease control in the form of a pest control or a place where the occurrence of the pest is unfavorable, as it is or to be appropriately diluted or suspended in water to control various pests Use it. The amount used varies depending on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. It is preferable to use at a concentration of 0.0001 to 5000 ppm, preferably 0.01 to 1000 ppm. Moreover, the application amount per 10a is generally 1 to 300 g as an active ingredient.

  The insecticide containing the compound represented by the general formula (1) of the present invention as an active ingredient is various agricultural and forestry, horticulture, stored grain pests, sanitary pests or lines that individually harm paddy rice, fruit trees, vegetables, other crops and flowers. It may be used for pest control such as insects, but in addition, in order to obtain a more excellent control effect against the control of a wide variety of pests that occur at the same time, one of other insecticides and / or fungicides A combination of the above may also be used.

  When the compound represented by the general formula (1) of the present invention is used in combination with one or more other insecticides and / or fungicides, the compound represented by the general formula (1) and other insecticides are used. And / or may be used as a mixed composition of fungicides, or may be used by mixing the compound represented by the general formula (1) with other insecticides and / or fungicides during agrochemical treatment. .

  In addition, the compound represented by the general formula (1) is 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 composition can also be expected to have an additive effect or a synergistic effect.

  The following examples explain typical examples of the present invention, but the present invention is not limited thereto.

[Example 1]
Preparation of 5-benzamide-N-{(2,6-dimethyl-4-heptafluoroisopropyl) phenyl} furan-2-carboxylic acid amide (Compound No. 4-1)

[Example 1-1]
Production of N-{(2,6-dimethyl-4-heptafluoroisopropyl) phenyl} -2-nitrofuran-5-carboxylic acid amide 2.5 g of 5-nitrofuran-2-carboxylic acid and 0.1 g of DMF in 15 ml of toluene The mixture was charged with 2.32 g of thionyl chloride, heated at 80 ° C. for 1 hour, and then reacted under reflux for 2 hours. The solvent was distilled off under reduced pressure to obtain a crude acid chloride.

2.18 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 1.48 g of pyridine were charged in 25 ml of THF, and the crude acid chloride obtained above was dissolved in 5 ml of THF and added. After stirring at room temperature for 2 hours, ethyl acetate was charged, washed successively with 5% aqueous hydrochloric acid and saturated aqueous sodium bicarbonate, and dried 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 = 10: 1 → 8: 2) to obtain 5.2 g of the desired product as a solid (yield). Rate 85% vs. aniline).
¹ H NMR (CDCl ₃ ) δ 2.36 (6H, s), 7.37 (2H, s), 7.41 (1H, d, J = 3.7Hz), 7.45 (1H, d, J = 3.7Hz), 7.87 (1H , brs).

[Example 1-2]
Preparation of 2-amino-N-{(2,6-dimethyl-4-heptafluoroisopropyl) phenyl} furan-5-carboxylic acid amide N-{(2,6-dimethyl-4-heptafluoroisopropyl) phenyl}- 2-Nitrofuran-5-carboxylic acid amide (1.11 g) and 10% palladium carbon (0.1 g) were charged into dioxane (20 ml), and a hydrogenation reaction was performed at room temperature and normal pressure for 3 hours. After purging with nitrogen, palladium carbon was filtered. The filtrate was used in the next reaction without further purification.

[Example 1-3]
5-Benzamide-N-{(2,6-dimethyl-4-heptafluoroisopropyl) phenyl} furan-2-carboxylic acid amide (Compound No. 4-1) Preparation of the dioxane solution obtained in Example 1-2 To half the amount, 5 ml of THF and 90 mg of pyridine were added. Next, 0.15 g of benzoyl chloride mixed with 1 ml of THF was added dropwise and stirred at room temperature for 5 hours. To the reaction solution was added 20 ml of ethyl acetate, and the mixture was washed successively with 5% aqueous hydrochloric acid solution and saturated aqueous sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 2) to obtain 0.15 g (yield 17%, vs. nitro form) of the desired product as a brown solid.
¹ H-NMR (DMSO-d ₆ ) δ 2.29 (6H, s), 6.63 (1H, d, J = 3.4 Hz), 7.44 (2H, s), 7.48-7.56 (3H, m), 7.60-7.64 ( 1H, m), 8.02-8.05 (2H, m), 9.75 (1H, s), 11.78 (1H, s).

[Example 2]
Preparation of 5- [N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] carbamoyl] furan-2-yl-carbamic acid 2,2,2-trichloroethyl ester (Compound No. 4-66) To half of the dioxane solution obtained in Example 1-2, 0.21 g of pyridine and 0.22 g of 2,2,2-trichloroethyl chloroformate were added and stirred for 1 hour. After charging 20 ml of ethyl acetate, it was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1 → 6: 4) to obtain 0.11 g of the desired product as an amorphous product (yield). Rate 18% vs. nitro).
¹ H NMR (CDCl ₃ ) δ2.26 (6H, s), 4.98 (2H, s), 6.29 (1H, d, J = 3.6Hz), 7.35-7.43 (3H, m), 9.70 (1H, s) , 11.4 (1H, brs).

[Example 3]
Preparation of 5- [N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] carbamoyl] thiophen-2-yl-carbamic acid 2,2,2-trichloroethyl ester (Compound No. 1-66)

[Example 3-1]
Preparation of a mixture consisting of 5-nitrothiophene-2-carboxylic acid ethyl ester and 4-nitrothiophene-2-carboxylic acid ethyl ester 12 ml of concentrated nitric acid was cooled to 5 ° C., and 12 ml of concentrated sulfuric acid was added dropwise. While maintaining the internal temperature at 10 ° C. or lower, 5.07 g of ethyl thiophene-2-carboxylate was added dropwise over 30 minutes, followed by stirring at room temperature for 2 hours. After discharging into ice water, the precipitated solid was filtered. The obtained solid was dissolved in ethyl acetate and washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting solid was washed with hexane to give 5-nitrothiophene-2-carboxylic acid ethyl ester and 4-nitrothiophene-2- 4.03 g of a mixture consisting of carboxylic acid ethyl ester was obtained. The mixing ratio of 5-nitrothiophene-2-carboxylic acid ethyl ester and 4-nitrothiophene-2-carboxylic acid ethyl ester was 1: 1.

[Example 3-2]
Preparation of a mixture consisting of 5-nitrothiophene-2-carboxylic acid and 4-nitrothiophene-2-carboxylic acid The ratio of 5-nitrothiophene-2-carboxylic acid ethyl ester to 4-nitrothiophene-2-carboxylic acid ethyl ester is A mixture of 1: 1 (4.03 g) and sodium hydroxide (1.6 g) were added to a mixture of water (15 ml) and methanol (15 ml), and the mixture was stirred at room temperature for 2 hours. After draining water, the pH was adjusted to 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to give 5-nitrothiophene-2-carboxylic acid and 4-nitrothiophene. 0.26 g of a mixture consisting of 2-carboxylic acid was obtained. The mixing ratio of 5-nitrothiophene-2-carboxylic acid and 4-nitrothiophene-2-carboxylic acid was 1: 3.

[Example 3-3]
N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -4-nitrothiophene-2-carboxylic acid amide and N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -5 -Production of nitrothiophene-2-carboxylic acid amide A mixture of 5-nitrothiophene-2-carboxylic acid and 4-nitrothiophene-2-carboxylic acid (mixing ratio 1: 3) 0.25 g was charged in 5 ml of toluene. , 1 drop of DMF and 0.5 ml of thionyl chloride were added, and the mixture was stirred for 1 hour under reflux. After cooling to room temperature, the solvent was distilled off under reduced pressure to obtain a crude acid chloride. 2,6-Dimethyl-4-heptafluoroisopropylaniline (0.41 g) and pyridine (0.23 g) were charged in 5 ml of THF, and the acid chloride obtained above was added thereto, followed by stirring for 1 hour. Ethyl acetate was added, and the mixture was washed successively with water, 5% aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1 → 6: 4), and N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -5. 90 mg of nitrothiophene-2-carboxylic acid amide and 0.19 g of N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -4-nitrothiophene-2-carboxylic acid amide were obtained as solids, respectively. It was.
N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -5-nitrothiophene-2-carboxylic acid amide: ¹ H NMR (CDCl ₃ ) δ 2.35 (6H, s), 7.37 (2H , s), 7.42 (1H, brs), 7.57 (1H, d, J = 4.4Hz), 7.93 (1H, d, J = 4.4Hz).
N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -4-nitrothiophene-2-carboxylic acid amide: ¹ H NMR (CDCl ₃ ) δ2.34 (6H, s), 7.37 (2H , s), 7.52 (1H, brs), 8.15 (1H, d, J = 1.2Hz), 8.51 (1H, d, J = 1.2Hz).

[Example 3-4]
Preparation of 5-amino-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiophene-2-carboxylic acid amide N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl]- 0.09 g of 5-nitrothiophene-2-carboxylic acid amide and 0.19 g of tin (II) chloride were charged into 3 ml of methanol, 3 ml of concentrated hydrochloric acid was added, and the mixture was stirred at 60 ° C. for 2 hours. After cooling to room temperature, the mixture was neutralized with an aqueous potassium carbonate solution, and the precipitated solid was filtered. After extraction with ethyl acetate, it was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was directly used in the next reaction.

[Example 3-5]
Preparation of 5- [N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] carbamoyl] thiophen-2-yl-carbamic acid 2,2,2-trichloroethyl ester (Compound No. 1-66) After adding 47 mg of pyridine and 3 ml of THF to the residue obtained in Example 3-4, 46 mg of 2,2,2-trichloroethyl chloroformate was added and stirred at room temperature for 1 hour. After discharging into water, the mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 8: 2 → 6: 4) to obtain 40 mg of the desired product as a solid (yield 34). % Vs. nitro).
¹ H NMR (CDCl ₃ ) δ2.34 (6H, s), 4.86 (2H, s), 6.69 (1H, brs), 7.12 (1H, brs), 7.34 (2H, s), 7.52 (1H, brs) , 7.78 (1H, brs).

[Example 4]
Preparation of 2- [N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] carbamoyl] thiophen-3-yl-carbamic acid 2,2,2-trichloroethyl ester (Compound No. 3-66)

[Example 4-1] Preparation of 4-amino-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiophene-2-carboxylic acid amide N-[( 2,9-dimethyl-4-heptafluoroisopropyl) phenyl] -4-nitrothiophene-2-carboxylic acid amide (0.19 g) and tin (II) chloride (0.33 g) were charged in ethanol (4 ml), and concentrated hydrochloric acid (4 ml) was added. The mixture was stirred at 60 ° C. for 2 hours. After cooling to room temperature, the mixture was neutralized with an aqueous potassium carbonate solution, and the precipitated solid was filtered. After extraction with ethyl acetate, it was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 7: 3 → 3: 7) to obtain 0.14 g of the desired product as a solid (yield 80%).

[Example 4-2]
Preparation of 2- [N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] carbamoyl] thiophen-4-yl-carbamic acid 2,2,2-trichloroethyl ester (Compound No. 3-66) 4 -Amino-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiophene-2-carboxylic acid amide 0.14 g and pyridine 54 mg were charged in 3 ml of THF, and 2,2,2-trichlorochloroformate was charged. 80 mg of ethyl was added and stirred at room temperature for 1 hour. After discharging into water, the mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 8: 2 → 7: 3) to obtain 0.1 g of the desired product as an amorphous product (yield). Rate 50%).
¹ H NMR (CDCl ₃ ) δ 2.35 (6H, s), 4.85 (2H, s), 7.22 (1H, brs), 7.28 (1H, brs), 7.35 (2H, s), 7.41 (1H, s) , 7.46 (1H, s).

[Example 5]
Preparation of 2-benzamide-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiophene-4-carboxylic acid amide (Compound No. 2-1)

[Example 5-1]
Preparation of N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -2-nitrothiophene-4-carboxylic acid amide 1.0 g of 2-nitrothiophene-4-carboxylic acid was charged into 10 ml of toluene. , 0.1 g of DMF and 0.89 g of thionyl chloride were added, and the mixture was stirred for 1 hour under reflux. After cooling to room temperature, the solvent and excess thionyl chloride were distilled off under reduced pressure to obtain crude acid chloride. 1,48 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 0.62 g of pyridine were charged in 10 ml of THF, the previously obtained acid chromatography was added, and the mixture was stirred for 1 hour. Ethyl acetate was added, and the mixture was washed successively with water, 5% aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1 → 7: 3) to obtain 1.7 g of the desired product as a white solid (73% yield, aniline). .

[Example 5-2]
Preparation of 2-amino-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiophene-2-carboxylic acid amide N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl]- 0.54 g of 2-nitrothiophene-4-carboxylic acid amide and 0.94 g of tin (II) chloride were charged into 6 ml of methanol, 6 ml of concentrated hydrochloric acid was added, and the mixture was stirred at 60 ° C. for 2 hours. After cooling to room temperature, water was added and the reaction solution was neutralized with potassium carbonate. After charging ethyl acetate, the mixture was filtered through Celite, and the organic layer was dried over anhydrous magnesium sulfate. Anhydrous sodium sulfate was filtered, and the filtrate was used for the next reaction as it was.

[Example 5-3]
Preparation of 2-benzamide-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiophene-4-carboxylic acid amide (Compound No. 2-1) Half of the solution obtained in Example 5-2 To the mixture, 0.10 g of pyridine and 87 mg of benzoyl chloride were added and stirred for 1 hour. After charging ethyl acetate, it was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1 → 7: 3) to obtain 0.11 g of the desired product as an amorphous product (yield). Rate 35% vs. nitro).
¹ H-NMR (DMSO-d ₆ ) δ 2.36 (6H, s), 7.33 (2H, s), 7.45-7.60 (3H, m), 7.75 (1H, s), 7.79 (1H, d, J = 1.5 Hz), 8.05 (2H, d, J = 7.3Hz), 9.52 (1H, s), 11.5 (1H, broad-s).

[Example 6]
Preparation of 4- [N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] carbamoyl] thiophen-2-yl-carbamic acid 2,2,2-trichloroethyl ester (Compound No. 2-66) To half the amount of the solution obtained in Example 5-2, 0.10 g of pyridine and 0.13 g of 2,2,2-trichloroethyl chloroformate were added and stirred for 1 hour. After charging ethyl acetate, it was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1 → 7: 3) to obtain 0.12 g of the desired product as an amorphous product (yield). Rate 33% vs. nitro).
¹ H NMR (CDCl ₃ ) δ2.37 (6H, s), 4.87 (2H, s), 7.11 (1H, brs), 7.17 (1H, brs), 7.35 (2H, s), 7.49 (1H, brs) , 7.56 (1H, brs).

[Example 7]
Preparation of N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -2- (N-methylbenzamido) thiazole-5-carboxylic acid amide (Compound No. 10-13)

[Example 7-1]
Preparation of 2-aminothiazole-5-carboxylic acid 5.0 g (29.1 mmol) of 2-aminothiazole-5-carboxylic acid ethyl ester is suspended in 40 ml of water, charged with 2.32 g of NaOH, Stir for hours. After heating at 50 ° C. for 2 hours, the mixture was cooled to room temperature and concentrated hydrochloric acid was added to adjust the pH to about 1. The precipitated solid was collected by filtration to obtain 3.76 g of the desired product as a solid (yield: 90%).

[Example 7-2]
Preparation of 2-chlorothiazole-5-carboxylic acid After charging 3.5 ml of 2-aminothiazole-5-carboxylic acid and 4.90 g of copper (II) chloride into 50 ml of acetonitrile, and adding 3.70 g of isoamyl nitrite , And stirred at 70 ° C. for 2 hours. After cooling to room temperature, the solid content was filtered, and the solvent was distilled off from the filtrate under reduced pressure. The obtained residue was dissolved in ethyl acetate and washed successively with 5% aqueous hydrochloric acid and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was sludged with hexane to obtain 3.3 g of the desired product as a solid (yield: 83%).

[Example 7-3]
2-Chloro-N- [2,6-dimethyl-4-heptafluoroisopropyl] phenyl] Preparation of thiazole-5-carboxylic acid amide 1.0 g of 2-chlorothiazole-5-carboxylic acid, 1 drop of DMF in 10 ml of toluene After charging, 0.87 g of thionyl chloride was added, and the mixture was stirred for 2 hours under reflux. Although it melt | dissolved gradually at this time, the solid substance remained. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was suspended in 5 ml of THF to obtain Liquid A. Liquid A was added to 8 ml of THF in which 1.5 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 0.45 g of pyridine were dissolved, and the mixture was stirred at room temperature for 2 hours. After discharging into water, the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (N-hexane: ethyl acetate = 10: 1 → 7: 3) to obtain 1.3 g of the desired product as a solid (yield). Rate: 49%).
¹ H-NMR (CDCl ₃ ) δ 2.31 (6H, s), 7.35 (2H, s), 8.08 (1H, s).

[Example 7-4]
Preparation of 2-methylamino-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiazole-5-carboxylic acid amide 2-Chloro-N- [2,6-dimethyl-4-heptafluoroisopropyl ] Phenyl] Thiazole-5-carboxylic acid amide (1.0 g) was charged into acetonitrile (10 ml), 40% methylamine methanol solution (1.0 g, 13.1 mmol) was added, and the mixture was stirred at 60 ° C. for 3 hours. 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 → 1: 1) to obtain 0.63 g of the desired product as a solid (yield). 63%).
¹ H-NMR (CDCl ₃ ) δ 2.32 (6H, s), 3.01 (3H, s), 5.94 (1H, broad-s), 7.00 (1H, broad-s), 7.33 (2H, s), 7.72 ( 1H, broad-s).

[Example 7-5]
Preparation of N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -2- (N-methylbenzamido) thiazole-5-carboxylic acid amide (Compound No. 10-13) 2-Methylamino-N- [(2,6-Dimethyl-4-heptafluoroisopropyl) phenyl] thiazole-5-carboxylic acid amide (0.20 g) and pyridine (73 mg) were charged in THF (3 ml), benzoyl chloride (72 mg) was added, and the mixture was stirred at room temperature for 30 minutes. . After stirring at 50 ° C. for 2 hours, 0.15 g of benzoyl chloride was added, and the mixture was stirred at 50 ° C. for 4 hours. After cooling to room temperature, ethyl acetate was added and washed with saturated aqueous sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1 → 1: 1) to obtain 0.23 g of the desired product as a solid (yield: 92%).
¹ H-NMR (CDCl ₃ ) δ 2.35 (6H, s), 3.72 (3H, s), 7.20 (1H, broad-s), 7.35 (2H, s), 7.50-7.58 (5H, m), 8.21 ( 1H, broad-s).

[Example 8]
Preparation of N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -2- (N-methylbenzamido) thiazole-4-carboxylic acid amide (Compound No. 11-13)

[Example 8-1]
Preparation of 2-aminothiazole-4-carboxylic acid 5.0 g of 2-amino-thiazole-4-carboxylic acid ethyl ester was charged in 50 ml of water, and 2.32 g of sodium hydroxide was added, followed by stirring at room temperature for 3 hours. did. After adjusting to pH 1 with concentrated hydrochloric acid, the precipitated crystals were filtered and dried under reduced pressure to obtain 4.28 g of the desired product as a solid (yield 100%).

[Example 8-2]
Production of 2-chlorothiazole-4-carboxylic acid 3.78 g of 2-aminothiazole-4-carboxylic acid was suspended in a mixed solution of 70 ml of concentrated hydrochloric acid and 40 ml of dioxane, and cooled to 0 ° C. Sodium nitrite (2.72 g) was dissolved in 10 ml of water and added dropwise while maintaining the internal temperature at 5 ° C. or lower. After stirring at 0 to 5 ° C. for 1 hour, 3.86 g of copper (I) chloride was charged in portions, stirred at room temperature for 8 hours, and allowed to stand at room temperature for 3 days. After charging water, the mixture was extracted 3 times with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was sludged with hexane to obtain 1.20 g of the desired product as a solid (yield: 28%).
¹ H-NMR (DMSO-d ₆ ) δ 8.44 (1H, s), 13.3 (1H, broad-s).

[Example 8-3]
2-Chloro-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] Preparation of thiazole-4-carboxylic acid amide 1.10 g of 2-chlorothiazole-4-carboxylic acid was charged into 10 ml of toluene. After adding 1 drop of DMF and 1.20 g of thionyl chloride, the mixture was stirred at 80 ° C. for 1 hour and at 100 ° C. for 1 hour. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was sludged with hexane to obtain 1.10 g of an acid chloride as a white solid. To 5 ml of THF in which 0.60 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 0.25 g of pyridine were dissolved, 0.42 g of the previously synthesized acid chloride was added and stirred at room temperature for 1 hour. After charging ethyl acetate, the mixture was washed with 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was sludged with hexane to obtain 0.61 g of the desired product as a solid (yield: 68%).
¹ H-NMR (CDCl ₃ ) δ 2.35 (6H, s), 7.35 (2H, s), 8.14 (1H, s), 8.53 (1H, broad-s).

[Example 8-3]
Preparation of 2-methylamino-N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiazole-4-carboxylic acid amide 2-chloro-N-[(2,6-dimethyl-4-heptafluoro Isopropyl) phenyl] thiazole-4-carboxylic acid amide 0.90 g was charged with 5 ml of 40% methylamine methanol solution and left at room temperature for 3 days. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (N-hexane: ethyl acetate = 8: 2 → 1: 1) to obtain 0.62 g of the desired product as a solid. (Yield: 69%).
¹ H-NMR (CDCl ₃ ) δ 2.35 (6H, s), 4.12 (3H, d, J = 5.3), 5.11 (1H, d, J = 5.3), 7.33 (2H, s), 7.45 (1H, s ), 8.61 (1H, broad-s).

[Example 8-4]
Preparation of N-[(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] -2- (N-methylbenzamido) thiazole-4-carboxylic acid amide (Compound No. 11-13) 2-Methylamino-N- [(2,6-dimethyl-4-heptafluoroisopropyl) phenyl] thiazole-4-carboxylic acid amide 0.28 g, pyridine 0.10 g was charged in THF 5 ml, benzoyl chloride 0.098 g was charged at room temperature. For 30 minutes and then at 50 ° C. for 2 hours. 0.20 g of benzoyl chloride was added, and the mixture was stirred at 50 ° C. for 2 hours. After cooling to room temperature, ethyl acetate was added, followed by washing with a saturated aqueous sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (N-hexane: ethyl acetate = 10: 1 → 3: 1) to obtain 0.23 g of the desired product as a solid (yield: 66%).
¹ H-NMR (CDCl ₃ ) δ 2.38 (6H, s), 3.72 (3H, s), 7.36 (2H, s), 7.50-7.61 (5H, m), 8.00 (1H, s), 8.69 (1H, broad-s).

[Example 9]
Production of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-4-benzamido-1-methyl-1H-pyrrole-2-carboxylic acid amide (Compound No. 9-1)

[Example 9-1]
Preparation of ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate 3 ethyl 4-nitropyrrole-2-carboxylate dissolved in 10 ml of DMF in a solution of 0.78 g of 60% sodium hydride in 10 ml of DMF 0.0 g was added dropwise. After stirring at room temperature for 1 hour, 2.77 g of methyl iodide dissolved in 5 ml of DMF was added dropwise. After further stirring for 3 hours at room temperature, the reaction solution was charged with ethyl acetate and then with water. The organic phase was separated, washed once with water, and dried over anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1 → 2: 1) to give 2.50 g of the desired product (yield 77%). ) Was obtained as a white solid.
¹ H-NMR (CDCl ₃ ) δ 1.37 (3H, t, J = 7.3Hz), 3.99 (3H, s), 4.32 (2H, q, J = 7.3Hz), 7.42 (1H, d, J = 2.0Hz ), 7.59 (1H, d, J = 2.0Hz).

[Example 9-2]
Production of 1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid 2.50 g of ethyl 1-methyl-4-nitropyrrole-2-carboxylate was added to a mixed solvent of 10 ml of THF and 10 ml of water and stirred at 5 ° C. did. Next, 0.76 g (18.9 mmol) of sodium hydroxide was charged, and the mixture was returned to room temperature and stirred for 6 hours. Ethyl acetate was added to the reaction solution, the aqueous phase was separated, and adjusted to pH 1 with 2N hydrochloric acid. The precipitated solid was collected by filtration and dried at 50 ° C. under reduced pressure to obtain 2.01 g of the desired product as a white solid (yield 94%).
¹ H-NMR (DMSO-d ₆ ) δ 3.92 (3H, s), 7.26 (1H, d, J = 2.0 Hz), 8.23 (1H, d, J = 2.0 Hz), 13.16 (1H, broad).

[Example 9-3]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid amide 1-methyl-4-nitro-1H-pyrrolecarboxylic acid 1 0.0 g and 0.1 ml of DMF in 10 ml of toluene were charged with 3.0 g of thionyl chloride and stirred at 90 ° C. for 1.5 hours. The residue obtained by concentrating the reaction solution under reduced pressure was dissolved in 5 ml of THF, and dropped into a solution obtained by adding 1.70 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 0.56 g of pyridine to 15 ml of THF. did. After stirring at 70 ° C. for 5 hours, the temperature was returned to room temperature, and ethyl acetate and 1N hydrochloric acid were added to separate the organic phase. The extract was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to obtain 1.76 g of the desired product as a white solid (yield 72%).
¹ H-NMR (DMSO-d ₆ ) δ 2.28 (6H, s), 3.93 (3H, s), 7.43 (2H, s), 7.67 (1H, d, J = 2.0 Hz), 8.25 (1H, d, J = 2.0Hz), 9.89 (1H, s).

[Example 9-4]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-4-amino-1-methyl-1H-pyrrole-2-carboxylic acid amide N- (2,6-dimethyl-4-heptafluoroisopropyl ) 1.60 g (3.62 mmol) of phenyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid amide 0.1 g of 10% Pd-C is added to 20 ml of methanol, and hydrogenation reaction is performed at room temperature and normal pressure. went. After removing the catalyst by filtration, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 4) to give 0.61 g of the desired product in brown. Obtained as an oil (41% yield).
¹ H-NMR (CDCl ₃ ) δ 2.32 (6H, s), 2.98 (2H, broad), 3.85 (3H, s), 6.32 (1H, s), 6.37 (1H, d, J = 2.0Hz), 7.13 (1H, s), 7.32 (2H, s).

[Example 9-5]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-4-benzamido-1-methyl-1H-pyrrole-2-carboxylic acid amide (Compound No. 9-1) N- (2,6- To a solution of 0.20 g of dimethyl-4-heptafluoroisopropyl) phenyl 4-amino-1-methyl-1H-pyrrole-2-carboxylic acid amide and 0.05 g of pyridine in 5 ml of THF, 68 mg of benzoyl chloride is added at room temperature. Stir for 2 hours. Ethyl acetate and 1N hydrochloric acid were added to the reaction solution to separate the organic phase. The extract was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 2) to obtain 0.13 g of the desired product as a light brown amorphous (yield 52%).
¹ H-NMR (CDCl ₃ ) δ 2.33 (6H, s), 3.94 (3H, s), 6.92 (1H, broad), 7.16 (1H, s), 7.28 (1H, d, J = 1.5Hz), 7.34 (2H, s), 7.46-7.57 (3H, m), 7.82-7.86 (3H, m).

  Next, although the formulation example containing the compound represented by General formula (1) of this invention as an active ingredient is shown, this invention is not limited to these. In the preparation examples, “parts” means “parts by weight”.

[Formulation Example 1]
An emulsion was obtained by uniformly stirring and mixing 20 parts of the present compound represented by the general formula (1), 10 parts of Solpol 355S (manufactured by Toho Chemical Co., Ltd., surfactant) and 70 parts of xylene.

[Formulation Example 2]
10 parts of the compound of the present invention represented by the general formula (1), 2 parts of sodium alkylnaphthalene sulfonate, 1 part of sodium lignin sulfonate, 5 parts of white carbon, 82 parts of diatomaceous earth are uniformly stirred and mixed to obtain a wettable powder. Got.

[Formulation Example 3]
The compound of the present invention represented by the general formula (1) 0.3 part and white carbon 0.3 part are uniformly mixed, and 99.2 parts of clay and 0.2 part of Doreles A (Sankyo) are added to make uniform. To obtain a powder.

[Formulation Example 4]
The compound of the present invention represented by the general formula (1), 2 parts of white carbon, 2 parts of white carbon, 2 parts of sodium lignin sulfonate, 94 parts of bentonite are uniformly ground and mixed, then added with water, kneaded, granulated and dried. To obtain granules.

[Formulation Example 5]
After thoroughly stirring and mixing 20 parts of the compound of the present invention represented by the general formula (1) and 5 parts of a 20% aqueous solution of polyvinyl alcohol, 75 parts of a 0.8% aqueous solution of xanthan gum is added and mixed again by stirring. Got.
Furthermore, in order to clarify that the compound represented by the general formula (1) of the present invention has excellent insecticidal activity, test examples are shown below, but the present invention is not limited thereto.

[Test Example 1]
Insecticidal test against Spodoptera litura Cabbage leaf pieces were immersed for 30 seconds in a chemical solution in which a test compound was diluted to a predetermined concentration and air-dried. The sample was left in a constant temperature room at 25 ° C., and the number of live and dead insects was examined after 6 days. It was done in two lanes in 1 ward and 5 animals.
As a result, at 1000 ppm, compound numbers 2-1, 2-66, 4-1, 9-1, 9-7, 9-66, 11-14, 11-16, 11-19, 11-33, 11- 42 and 11-66 showed a death rate of 70% or more.

[Test Example 2]
Insecticidal test against black moth (Plutella xylostella) Cabbage leaf pieces were immersed for 30 seconds in a chemical solution obtained by diluting a test compound to a predetermined concentration, air-dried, and placed in a 7 cm polyethylene cup to release second-instar larvae. The sample was left in a constant temperature room at 25 ° C., and the number of live and dead insects was examined after 6 days. It was done in two lanes in 1 ward and 5 animals.
As a result, at 1000 ppm, 2-1, 2-66, 4-1, 9-1, 9-7, 9-66, 11-14, 11-16, 11-19, 11-33, 11-42, 11-66 showed a death rate of 70% or more.

Claims (5)

General formula (1)

{In the formula, Het is a 5-membered aromatic heterocyclic group (herein, the aromatic 5-membered heterocyclic group is pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, A thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a furyl group, a thienyl group, an oxadiazolyl group and a triazolyl group).
Z is _{-C (= G 1) Q 1} , -C (= G 1) G 2 R 3, -SO 2 Q 1 or -Q _{1 (wherein, G 1,} G ₂ represents an oxygen atom or a sulfur atom ,
Q ₁ and R ₃ are C1-C6 alkyl groups,
A C1-C6 haloalkyl group,
A C2-C6 alkenyl group,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group,
A C2-C6 haloalkynyl group,
A C3-C8 cycloalkyl group,
A C3-C8 halocycloalkyl group,
A phenyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement Fe Group,
A naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement naphth Group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, An oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group), or the same or different, a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 halo An alkylthio group, 1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, A substituted heterocyclic group having one or more substituents selected from a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (wherein the heterocyclic group is a pyridyl group, pyridine- N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl Group, thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group.),
-E ₁ -Z ₁ -R ₄
(Where
E ₁ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C2-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group,
R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group,
A C3-C8 cycloalkyl group,
A C3-C8 halocycloalkyl group,
A phenyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement Fe Group,
A naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement naphth Group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, An oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group), or the same or different, a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 halo An alkylthio group, 1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, A substituted heterocyclic group having one or more substituents selected from a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group is shown (the heterocyclic group here is a pyridyl group, Pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiyl Zoriru group, thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a tetrazolyl group.),
Z ₁ represents —O—, —S—, —SO—, —SO ₂ —, —C (═O) —, —C (═O) O—, —OC (═O) —, —N (R ₅ ) -, - C (= O ) N (R 5) -, or _{-N (R 5) C (=} O) - (R 5 is a hydrogen atom, C1-C4 alkyl groups, C1-C4 alkylcarbonyl groups, C1 -Represents a C4 haloalkylcarbonyl group or a C1-C4 alkoxycarbonyl group. ),
Or _-E 2 -R ₆
(Where
E ₂ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C2-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group,
R ₆ is a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,
A cyano group,
Nitro group,
A hydroxy group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, Or complex Group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group) , Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group).
Alternatively, they may be the same or different and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group. Group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy Substituted heterocyclic ring having one or more substituents selected from a group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group Group (where Heterocyclic groups are pyridyl, pyridine-N-oxide, pyrimidinyl, pyrazinyl, pyridazyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, oxazolyl, isoxazolyl, oxadiazolyl Group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, or tetrazolyl group). ) And
G ₃ represents an oxygen atom or a sulfur atom,
X may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group,
n represents an integer of 0 to 3,
Q ₂ may be a phenyl group, or may be the same or different, and may be a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group. C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1 -C6 haloalkylsulfonyloxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, phenyl group, the same or different, halogen atom, C1 -C6 Alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 haloalkylsulfonyloxy group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group A phenyl group, a thienyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, C1-C6 alkoxy group C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1- A substituted phenyl group having one or more substituents selected from a thienyl group optionally substituted with a C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxy group, and a pentafluorosulfanyl group,
A naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group A substituted naphthyl group having one or more substituents selected from a group, a hydroxy group, and a pentafluorosulfanyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, C1 -C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkyl Sul A substituted heterocyclic group having one or more substituents selected from a nyl group, a cyano group, a nitro group, a hydroxy group, and a pentafluorosulfanyl group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group) , Pyrimidinyl group, pyrazinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolyl group, or tetrazolyl group. ,
Tetrahydronaphthalene group,
Alternatively, they may be the same or different, and may be a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, One or more substitutions selected from C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group A tetrahydronaphthalene group having a group,
R ₁ and R ₂ are each a hydrogen atom, oxygen atom, halogen atom, hydroxy group, cyano group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group,
A C1-C4 alkyl group,
A C1-C4 alkylcarbonyl group,
A C1-C4 haloalkylcarbonyl group,
A C2-C4 alkenyl group,
A C2-C4 haloalkenyl group,
A C2-C4 alkynyl group,
A C2-C4 haloalkynyl group,
A C1-C4 alkoxycarbonyl group,
A C1-C4 haloalkoxycarbonyl group,
A C2-C4 alkenyloxycarbonyl group,
A C2-C4 alkynyloxycarbonyl group,
Phenoxycarbonyl group, which may be the same or different, may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, One or more substituents selected from a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group Yes Substituted phenoxycarbonyl group that,
A C1-C4 alkylaminocarbonyl group,
A C1-C4 haloalkylaminocarbonyl group,
A C1-C4 alkylcarbonyloxy group,
A C1-C4 haloalkylcarbonyloxy group,
Benzoyl group, which may be the same or different, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1- C6-haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group 1 or more substituents selected from a group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Replacement Benzoyl group,
A C1-C4 alkoxy group,
A C1-C4 haloalkoxy group,
A benzyloxycarbonyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group One or more substituents selected from nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted benzyloxycarbonyl group having,
A C1-C4 alkylthio group,
A C1-C4 haloalkylthio group,
A C1-C4 alkylsulfinyl group,
A C1-C4 haloalkylsulfinyl group,
A C1-C4 alkylsulfonyl group,
A C1-C4 haloalkylsulfonyl group,
Benzenesulfonyl group, which may be the same or different, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, One or more substituents selected from a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group Have Substituted benzenesulfonyl group,
Benzylsulfonyl group, which may be the same or different, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, One or more substituents selected from a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group Have Substituted benzylsulfonyl group,
A C1-C4 alkoxy C1-C4 alkyl group,
A C1-C4 haloalkoxy C1-C4 alkyl group,
Or C (= O) C (= O) R ₇ (wherein R ₇ is a C1-C6 alkyl group,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group,
A C3-C8 halocycloalkyl group,
A C1-C6 alkoxy group,
Or a C1-C6 haloalkoxy group). }
A compound represented by The compound represented by the general formula (1) is represented by the following general formula (2)

(In the formula, A, E, and D independently represent a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and X, n, R ₁ , R ₂ , G ₃ , Z, and Q ₂ have the same meaning as described above. The compound of Claim 1 represented by this. In the general formula (2), Z is —C (= G ₁ ) Q ₁ , —C (= G ₁ ) G ₂ R ₃ , and Q ₂ is the general formula (3) (Chemical Formula 3)

(Wherein Y ₁ and Y ₅ may be the same or different and are each a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group). Group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, cyano group, Y ₃ is a C1-C6 haloalkyl group , A C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, and a C1-C6 haloalkylsulfonyl group, Y ₂ and Y ₄ represent a hydrogen atom, a halogen atom, and a C1-C4 alkyl group. ) Or the general formula (4)

(Wherein Y ₆ and Y ₉ may be the same or different and are each a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group). Group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, cyano group, Y ₈ is a C1-C6 haloalkyl group , C1-C4 haloalkoxy group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, _{Y 7} represents a hydrogen atom, a halogen atom, in.) showing the C1-C4 alkyl group The compound of claim 2 represented.   The compound according to claim 3, wherein, in the general formula (2), A is a sulfur atom, E is a nitrogen atom, D is a carbon atom, or A and E are carbon atoms, and D is a nitrogen atom.   An insecticide comprising the compound according to any one of claims 1 to 4 as an active ingredient.