JP2007099761A - Amide derivative and application method thereof as insecticide - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound exhibiting high insecticidal effect, and to provide an insecticide containing the compound. <P>SOLUTION: The compound is represented by general formula (1) [wherein, A<SB>1</SB>, A<SB>2</SB>, A<SB>3</SB>and A<SB>4</SB>are C, N or the like; Z is -C(=G<SB>1</SB>)Q<SB>1</SB>, -C(=G<SB>1</SB>)G<SB>2</SB>G<SB>3</SB>, -SO<SB>2</SB>Q<SB>1</SB>or -Q<SB>1</SB>; G<SB>3</SB>is O or the like; X is H, a halogen or the like; n is an integer of 0-4; Q<SB>2</SB>is phenyl, a heterocycle or the like; and R<SB>1</SB>and R<SB>2</SB>are a 1-4C alkoxycarbonyl or the like] and the insecticide contains the compound as an active ingredient. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to general formula (1)

{In the formula, A ₁ , A ₂ , A ₃ and A ₄ each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom, and Z represents —C (═G ₁ ) Q ₁ , —C ( = G ₁ ) G ₂ R ₃ , —SO ₂ Q ₁ or —Q ₁ (In the formula, G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom, and Q ₁ and R ₃ each independently Or an optionally substituted alkyl group, an optionally substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group; and G ₃ represents oxygen Represents an atom or a sulfur atom, X may be the same or different, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group, n represents an integer of 0 to 4, and Q ₂ represents Optionally substituted phenyl group, substituted Good naphthyl group, optionally substituted tetrahydronaphthyl radical or indicates an optionally substituted heterocyclic group,, R _1, R ₂ are each independently a hydrogen atom, an oxygen atom, a halogen atom, hydroxy group, Nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, may be substituted A good C2-C4 unsaturated alkyl group, an optionally substituted C1-C4 alkoxycarbonyl group, an optionally substituted C1-C4 alkenyloxycarbonyl group, an optionally substituted C1-C4 alkynyloxycarbonyl group, Optionally substituted phenoxycarbonyl group, optionally substituted 1-C4 alkylaminocarbonyl group, C1-C4 alkylcarbonyloxy group which may be substituted, benzoyl group which may be substituted, C1-C4 alkoxy group which may be substituted, C1 which may be substituted -C4 alkylthio group, C1-C4 alkylsulfinyl group which may be substituted, C1-C4 alkylsulfonyl group which may be substituted, benzenesulfonyl group which may be substituted, benzylsulfonyl group which may be substituted , An optionally substituted benzyl group, a substituted C1-C4 alkyl group, a substituted C1-C4 alkylcarbonyl group or —C (═O) C (═O) R ₇ (wherein R ₇ is a substituted group) And an optionally substituted alkyl group or an optionally substituted C1-C4 alkoxy group. ).
(However, R ₁ and R ₂ are both hydrogen atoms, both C1-C4 alkyl groups, both C1-C4 alkylcarbonyl groups, both C1-C4 haloalkylcarbonyl groups, a combination of hydrogen atoms and C1-C4 alkyl groups, hydrogen atoms, C1-C4 alkylcarbonyl group combination, hydrogen atom and C1-C4 haloalkylcarbonyl group combination, C1-C4 alkyl group and C1-C4 alkylcarbonyl group combination, C1-C4 alkyl group and C1-C4 haloalkylcarbonyl group combination Or a combination of a C1-C4 alkylcarbonyl group and a C1-C4 haloalkylcarbonyl group). } And a method for using the compound as an insecticide containing the compound as an active ingredient.

In WO 2005/21488 pamphlet and WO 2005/73165 pamphlet, description of a compound similar to the compound of the present invention is recognized, but it is clear that the compound is outside the scope of the claims of the present invention. is there.
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 use a compound represented by the general formula (1), an insecticide containing the compound as an active ingredient, and a combination of the compound and another insecticide and / or fungicide. It is to provide a method for controlling pests.

  As a result of intensive studies in order 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. The inventors have found a new use and have completed the present invention.

That is, the present invention is as follows.
[1] General formula (1) (Formula 2)

{In the formula, A ₁ , A ₂ , A ₃ and A ₄ each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom, and Z represents —C (═G ₁ ) Q ₁ , —C ( = G ₁ ) G ₂ R ₃ , —SO ₂ Q ₁ or —Q ₁ (In the formula, G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom, and Q ₁ and R ₃ each independently Or an optionally substituted alkyl group, an optionally substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group; and G ₃ represents oxygen Represents an atom or a sulfur atom, X may be the same or different, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group, n represents an integer of 0 to 4, and Q ₂ represents Optionally substituted phenyl group, substituted Good naphthyl group, optionally substituted tetrahydronaphthyl radical or indicates an optionally substituted heterocyclic group,, R _1, R ₂ are each independently a hydrogen atom, an oxygen atom, a halogen atom, hydroxy group, Nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, may be substituted A good C2-C4 unsaturated alkyl group, an optionally substituted C1-C4 alkoxycarbonyl group, an optionally substituted C1-C4 alkenyloxycarbonyl group, an optionally substituted C1-C4 alkynyloxycarbonyl group, Optionally substituted phenoxycarbonyl group, optionally substituted 1-C4 alkylaminocarbonyl group, C1-C4 alkylcarbonyloxy group which may be substituted, benzoyl group which may be substituted, C1-C4 alkoxy group which may be substituted, C1 which may be substituted -C4 alkylthio group, C1-C4 alkylsulfinyl group which may be substituted, C1-C4 alkylsulfonyl group which may be substituted, benzenesulfonyl group which may be substituted, benzylsulfonyl group which may be substituted , An optionally substituted benzyl group, a substituted C1-C4 alkyl group, a substituted C1-C4 alkylcarbonyl group or —C (═O) C (═O) R ₇ (wherein R ₇ is a substituted group) And an optionally substituted alkyl group or an optionally substituted C1-C4 alkoxy group. ).
(However, R ₁ and R ₂ are both hydrogen atoms, both C1-C4 alkyl groups, both C1-C4 alkylcarbonyl groups, both C1-C4 haloalkylcarbonyl groups, a combination of hydrogen atoms and C1-C4 alkyl groups, hydrogen atoms, C1-C4 alkylcarbonyl group combination, hydrogen atom and C1-C4 haloalkylcarbonyl group combination, C1-C4 alkyl group and C1-C4 alkylcarbonyl group combination, C1-C4 alkyl group and C1-C4 haloalkylcarbonyl group combination Or a combination of a C1-C4 alkylcarbonyl group and a C1-C4 haloalkylcarbonyl group.)}.

[2] In the general formula (1),
R ₁ and R ₂ are each independently a hydrogen atom, oxygen atom, halogen atom, hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, C1-C4 alkyl group, C1- C4-haloalkyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C1-C4 alkoxycarbonyl group , C1-C4 haloalkoxycarbonyl group, C1-C4 alkenyloxycarbonyl group, C1-C4 alkynyloxycarbonyl group, phenoxycarbonyl group, or the same or different, halogen atom, C1-C6 alkyl group, C1-C6 Haloalkyl group, C3-C8 Chloalkyl 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 Group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyl An oxy group, a substituted phenoxycarbonyl group having one or more substituents selected from a C1-C4 alkoxycarbonyl group, a C1-C4 alkylaminocarbonyl group, a C1-C4 haloalkylaminocarbonyl group, a C1-C4 alkylcarbonyl Nyloxy group, 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 halocyclo group Alkyl 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxy A substituted benzoyl group having one or more substituents selected from a sicarbonyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a benzyloxycarbonyl 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 haloalkylthio group , C1-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 C1-C4 halo A substituted benzyloxycarbonyl group having one or more substituents selected from an alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1- C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, benzenesulfonyl group, or 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 alkyls Finyl 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, C1-C4 haloalkyl A substituted benzenesulfonyl group having one or more substituents selected from a carbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a benzylsulfonyl 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 haloalkyl group O group, C1-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 alkyl A substituted benzylsulfonyl group having one or more substituents selected from a carbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl 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, C3-C8 halocycloalkyl group, C1-C6 al Alkoxy group, or indicates shown) C1-C6 haloalkoxy group, _(wherein, R 1, _{R 2} are both hydrogen atoms, both C1-C4 alkyl group, both C1-C4 alkyl group, both C1-C4 haloalkylcarbonyl group A combination of a hydrogen atom and a C1-C4 alkyl group, a combination of a hydrogen atom and a C1-C4 alkylcarbonyl group, a combination of a hydrogen atom and a C1-C4 haloalkylcarbonyl group, a combination of a C1-C4 alkyl group and a C1-C4 alkylcarbonyl group A combination of a C1-C4 alkyl group and a C1-C4 haloalkylcarbonyl group, or a combination of a C1-C4 alkylcarbonyl group and a C1-C4 haloalkylcarbonyl group),
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
Z is _{-C (= G 1) Q 1} , -C (= G 1) G 2 R 3, -SO 2 Q 1 or -Q ₁
(In the formula, G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
Q ₁ and R ₃ are each independently 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, C3 -C8 cycloalkyl group, C3-C8 halocycloalkyl group, phenyl 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 alkyl Sulfonyl group, C1-C6 haloalkylsulfonyl group, One or more selected from the following: a group, a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group A substituted phenyl group having a substituent, a naphthyl group, or 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 Haloalkylsulfoni 1 selected from a group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted naphthyl group and heterocyclic group having the above substituents (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group) 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)), or 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, a 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, pentafluoro A substituted heterocyclic group having one or more substituents selected from a sulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (wherein The heterocyclic group is pyridyl group Pyridine-N-oxide group, pyrimidinyl 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 is shown. ),
-E ₁ -Z ₁ -R ₄
Wherein 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, C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C8 cycloalkyl group. , C3-C8 halocycloalkyl group, phenyl 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 A substituent having one or more substituents selected from 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 Phenyl group, naphthyl group, or 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 tro 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 Substituted naphthyl group, heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group) Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group), or the same or different, Logen 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, pentafluorosulfanyl group, C1 -A substituted heterocyclic group having one or more substituents selected from a C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group. Group is pyridyl group, pyridine -N-oxide, pyrimidinyl, pyridazyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrole A 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
(Wherein 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 may be a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, the same or different, a halogen atom, a C1-C6 alkyl group, a 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group C1-C4 alkylcal A phenyl group, a substituted phenyl group having one or more substituents selected from a C1-C4 alkoxycarbonyl group, a naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1- C4 alkylcal A substituted naphthyl group having one or more substituents selected from a nyloxy group, a C1-C4 alkoxycarbonyl group, or a heterocyclic group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, Pyridazyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrole, imidazolyl, triazolyl, pyrazolyl Group, or a tetrazolyl 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, C1 -C6 Al Xi 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 1 or more selected from cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted heterocyclic groups having the following substituents (wherein the heterocyclic groups are pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyrani group) Le A xazolyl 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. ). ). ) And
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. A C1-C6 haloalkoxy group, a C1-C6 haloalkyl group optionally substituted with one or more hydroxyl groups, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group 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, pentafluorosulfur Nyl group, Fe Nyl 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 halo Alkoxy 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, phenyl group which may be substituted with pentafluorosulfanyl group, thienyl group, halogen atom which may be the same or different, C1-C6 alkyl group, C1-C6 haloalkyl group C3-C8 cycloal 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 , A C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxy group, or a thienyl group optionally substituted with a pentafluorosulfanyl group. A substituted phenyl group having one or more substituents, a naphthyl group, or 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 halocyclo Alkyl group, C1-C6 alkoxy Group, C1-C6 haloalkoxy group, C1-C6 haloalkyl group optionally substituted with one or more hydroxyl groups, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkyl group A substituted naphthyl group having at least one substituent selected from a sulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, and a pentafluorosulfanyl group, a heterocyclic group ( The heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group , Imidazolyl group, triazolyl Represents a ru group, a pyrazolyl group, or a tetrazolyl group. Or may be the same or different, and may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or one or more hydroxyl groups. C1-C6 haloalkyl 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 heterocyclic group having one or more substituents selected from a nitro group, a hydroxy group, and a pentafluorosulfanyl group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group) , Furyl group, thienyl group, oxazolyl group, isoxazolyl Oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolyl group, or tetrazolyl group.), Tetrahydronaphthalene group, or the same or different, halogen atom, C1-C6 alkyl Group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 haloalkyl group optionally substituted with one or more hydroxyl groups, C1-C6 alkylthio group, C1-C6 haloalkylthio group 1 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 substituent of the above,
The compound according to [1].

[3] In the general formula (1),
Z is _{-C (= G 1) Q 1} , -C (= G 1) G 3 R 3, -SO 2 Q 1 or -Q ₁
(In the formula, G ₁ and G ₃ each independently represent an oxygen atom or a sulfur atom,
R ₃ is 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, a C3- C8 halocycloalkyl group, phenyl 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, hydroxyl group Substituted phenyl having one or more substituents selected from Si group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Group, naphthyl group, or 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, Substituted naphthyl having one or more substituents selected from droxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Group, heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group) Group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group), or the same or different, 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, pentafluorosulfanyl group, C1-C4 A substituted heterocyclic group having one or more substituents selected from an alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (wherein the heterocyclic group is pyridyl Group, pyridine-N-oxide group , Pyrimidinyl 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, A triazolyl group, a pyrazolyl group, or a tetrazolyl group is shown. ),
-E ₁ -Z ₁ -R ₄
Wherein 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, C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C8 cycloalkyl group. , C3-C8 halocycloalkyl group, phenyl 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 A substituent having one or more substituents selected from 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 Phenyl group, naphthyl group, or 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 tro 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 Substituted naphthyl group or heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyrani group) Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group)), or the same or different Well, 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, pentafluorosulfanyl group , A substituted heterocyclic group having one or more substituents selected from a C1-C4 alkylcarbonyl group, 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, 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 is shown. ),
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. ),
-E ₂ -R ₆
(Wherein 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 may be 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, a C1-C6 alkyl group, a 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl Group, C1-C4 al A substituted phenyl group having one or more substituents selected from a kill carbonyloxy group, a C1-C4 alkoxycarbonyl group, a naphthyl group, or 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, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group , C1- A substituted naphthyl group having one or more substituents selected from a 4-alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a heterocyclic group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group) 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 , 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, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group. , C1- 6 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 1 selected from a group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted heterocyclic groups having the above substituents (the heterocyclic groups here are pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydro group) Pirani A benzoyl 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. ). )
Q ₁ is 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- C6-cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl Sulfinyl 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 alkylcarbonyloxy group, C1 -C4 alkoxycarbonyl group, acetylamino group, substituted phenyl group having one or more substituents which may be the same or different selected from phenyl group, heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine -N-oxide, pyrimidinyl, pyridazyl, pyrazyl, furyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, imidazolyl, triazolyl, pyrrole, pyrazolyl, or tetrazolyl 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 -C6 cycloalkyl group, C3-C6 halo A loalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, 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 alkylcarbonyloxy group, C1-C4 alkoxy A substituted heterocyclic group having one or more substituents which may be the same or different selected from a carbonyl group, an acetylamino group and a phenyl group (the heterocyclic group here is a pyridyl group, a pyridine-N-oxide group, Pyrimidinyl group, pyridazyl group, pyrazyl group, Lil group, a thienyl group, an oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group. ). ) And
Q ₂ represents the general formula (2)

Wherein Y ₁ and Y ₅ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl 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, a C1-C3 haloalkylsulfonyl group or a cyano group,, _{Y 3} is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group or a pentafluorosulfanyl group; Y ₂ and Y ₄ are each independently Hydrogen atom, halogen atom, Or a C1-C4 alkyl group.) Or a general formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl 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 or a cyano group, _{Y 8} is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group or a pentafluorosulfanyl group, Y ₇ is a hydrogen atom, a halogen atom Or a C1-C4 alkyl group Shown.) Represented by A compound according to claim 2.

  [4] An insecticide containing the compound according to any one of [1] to [3] as an active ingredient.

  [5] An effective amount of the compound according to any one of [1] to [3] is treated on a target useful crop or soil in order to protect the useful crop from pests. How to use the drug.

  The compound of the present invention exhibits an excellent control effect as an insecticide at a low dose, and also has other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides, etc. Even when used in combination, an excellent control effect is exhibited.

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

  The “optionally substituted alkyl group” is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxy Carbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, may be substituted Good phenyl group, A benzyl group that may be substituted, a phenylcarbonyl group that may be substituted, a phenylamino group that may be substituted, or a heterocyclic group that may be substituted; A chain, branched or cyclic alkyl group is meant.

  The “optionally substituted phenyl group” may be the same or different, and is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 Haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkyl Amino group, a It means a phenyl group substituted with a tilamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or an optionally substituted heterocyclic group. .

  The “optionally substituted naphthyl group” may be the same or different and is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 Haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkyl Amino group, a It means a naphthyl group substituted with a tilamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or an optionally substituted heterocyclic group. .

  The “optionally substituted heterocyclic group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro 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, C1-C6 alkylcarbonyl group, C1- C6-haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 Alkylamino group, ace This means a heterocyclic group substituted by a ruamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or an optionally substituted heterocyclic group. To do.

  The “optionally substituted tetrahydronaphthyl group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro 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, C1-C6 alkylcarbonyl group, C1- C6-haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 Alkyl Mino group, optionally substituted phenyl group, optionally substituted phenylcarbonyl group, optionally substituted phenylamino group, optionally substituted heterocyclic group, which may be the same or different. Means a modified tetrahydronaphthyl group.

  The “optionally substituted C2-C4 unsaturated alkyl group” means a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group. Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Even if it is replaced Phenyl group, optionally substituted benzyl group, optionally substituted phenylcarbonyl group, optionally substituted phenylamino group, optionally substituted heterocyclic group, which may be the same or different. A substituted linear or branched C2-C4 alkenyl group or C2-C4 alkynyl group is shown.

  The “optionally substituted C1-C4 alkoxycarbonyl group” means a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, substituted Been The same or different phenyl group, optionally substituted benzyl group, optionally substituted phenylcarbonyl group, optionally substituted phenylamino group, and optionally substituted heterocyclic group Means a well-substituted linear, branched or cyclic alkoxycarbonyl group having 1 to 4 carbon atoms.

  The “optionally substituted C1-C4 alkenyloxycarbonyl group” means a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group. Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Replace The same or different phenyl group which may be substituted, benzyl group which may be substituted, phenylcarbonyl group which may be substituted, phenylamino group which may be substituted, or heterocyclic group which may be substituted A linear, branched or cyclic alkenyloxycarbonyl group having 1 to 4 carbon atoms may be substituted.

  The “optionally substituted C1-C4 alkynyloxycarbonyl group” means a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group. Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Replace The same or different phenyl group which may be substituted, benzyl group which may be substituted, phenylcarbonyl group which may be substituted, phenylamino group which may be substituted, or heterocyclic group which may be substituted A linear, branched or cyclic alkynyloxycarbonyl group having 1 to 4 carbon atoms may be substituted.

  The “optionally substituted phenoxycarbonyl group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro 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, C1-C6 alkylcarbonyl group, C1- C6-haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 Alkyl Mino group, optionally substituted phenyl group, optionally substituted phenylcarbonyl group, optionally substituted phenylamino group, optionally substituted heterocyclic group, which may be the same or different. Means a substituted phenoxycarbonyl group.

  The “optionally substituted C1-C4 alkylaminocarbonyl group” is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group. Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Replaced The same or different phenyl group which may be substituted, benzyl group which may be substituted, phenylcarbonyl group which may be substituted, phenylamino group which may be substituted, or heterocyclic group which may be substituted Or a linear, branched or cyclic alkylaminocarbonyl group having 1 to 4 carbon atoms, which is well substituted.

  The “optionally substituted C1-C4 alkylcarbonyloxy group” means a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group. Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Replaced The same or different phenyl group which may be substituted, benzyl group which may be substituted, phenylcarbonyl group which may be substituted, phenylamino group which may be substituted, or heterocyclic group which may be substituted Or a well-substituted linear, branched or cyclic saturated or unsaturated alkylcarbonyloxy group having 1 to 4 carbon atoms.

  The “optionally substituted benzoyl group” may be the same or different and is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 Haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkyl An amino group, A cetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or a benzoyl group substituted with an optionally substituted heterocyclic group. .

  The “optionally substituted C1-C4 alkoxy group” is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, substituted May be An aryl group, an optionally substituted benzyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, an optionally substituted heterocyclic group, which may be the same or different. Means a linear, branched or cyclic alkoxy group having 1 to 4 carbon atoms.

  The “optionally substituted C1-C4 alkylthio group” is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, substituted Can be Phenyl group, optionally substituted benzyl group, optionally substituted phenylcarbonyl group, optionally substituted phenylamino group, optionally substituted heterocyclic group, which may be the same or different Means a straight, branched or cyclic alkylthio group having 1 to 4 carbon atoms.

  The “optionally substituted C1-C4 alkylsulfinyl group” means a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, substituted Been The same or different phenyl group, optionally substituted benzyl group, optionally substituted phenylcarbonyl group, optionally substituted phenylamino group, optionally substituted heterocyclic group Or a well-substituted linear, branched or cyclic alkylsulfinyl group having 1 to 4 carbon atoms.

  The “optionally substituted C1-C4 alkylsulfonyl group” means a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, substituted Has been A phenyl group which may be substituted, a benzyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, or a heterocyclic group which may be substituted, which may be the same or different A well-substituted linear, branched or cyclic alkylsulfonyl group having 1 to 4 carbon atoms is meant.

  The “optionally substituted benzenesulfonyl group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro 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, C1-C6 alkylcarbonyl group, C1- C6-haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 Alkyria Benzene substituted with an aryl group, an acetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or an optionally substituted heterocyclic group A sulfonyl group is meant.

  The “optionally substituted benzylsulfonyl group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro 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, C1-C6 alkylcarbonyl group, C1- C6-haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 Alkyria Benzyl substituted with an aryl group, an acetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or an optionally substituted heterocyclic group A sulfonyl group is meant.

  “Substituted C1-C4 alkyl group” means halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, optionally substituted phenyl group Replaced A benzyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, a linear group which may be the same or different with an optionally substituted heterocyclic group, It means a branched or cyclic alkyl group having 1 to 4 carbon atoms.

  “Substituted C1-C4 alkylcarbonyl group” means halogen atom, hydroxy group, cyano group, nitro group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group. Group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group , C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, optionally substituted phenyl Group, A benzyl group that may be substituted, a phenylcarbonyl group that may be substituted, a phenylamino group that may be substituted, or a heterocyclic group that may be substituted; A chain, branched or cyclic alkylcarbonyl group having 1 to 4 carbon atoms is meant.

  The “optionally substituted benzyl group” may be the same or different and is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 Haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkyl Amino group, a It means a benzyl group substituted with a tilamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, or an optionally substituted heterocyclic group. .

  The “optionally substituted phenoxy group” may be the same or different, and is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro 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 alkylcarbonyl group, C1-C6 Haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkyl An amino group, A cetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group, a phenoxy group substituted by an optionally substituted heterocyclic group .

  The “C1-C3 alkyl group” means, for example, a linear or branched alkyl group having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl, etc., and “C1 "-C4 alkyl group" means a linear or branched carbon atom such as n-butyl, s-butyl, i-butyl, t-butyl, cyclopropylmethyl, etc. in addition to "C1-C3 alkyl group" A C1-C6 alkyl group refers to, for example, n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, in addition to the “C1-C4 alkyl group”. A linear or branched alkyl group having 1 to 6 carbon atoms such as 2-hexyl, 4-methyl-2-pentyl, and 3-methyl-n-pentyl is shown.

  “C1-C3 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-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, 1-bromo- One or more halogens which may be the same or different, such as 1,1,2,3,3,3-hexafluoro-2-propyl, 1,1,2,3,3,3-hexafluoro-1-propyl A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an atom is shown, and “C1-C4 haloalkyl group” means, for example, 4-fluoro in addition to “C1-C3 haloalkyl group” -N-butyl, nona A linear or branched alkyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as uro-n-butyl, nonafluoro-2-butyl, etc .; “C1-C6 haloalkyl group” is the same or different from “C1-C4 haloalkyl group”, for example, 6,6,6-trifluoro-n-hexyl, nonafluoro-n-butyl, nonafluoro-2-butyl, etc. Or a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms.

  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, 3-butenyl, etc. Examples of the “C4 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4 , 4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc., a straight chain having a double bond in a carbon chain substituted by one or more halogen atoms which may be the same or different Or a branched alkenyl group having 2 to 4 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. The “C2-C4 haloalkynyl group” means, for example, the number of linear or branched carbon atoms having a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different 2 to 4 alkynyl groups are shown.

  The “C3-C8 cycloalkyl group” is, for example, a cycloalkyl group having 3 to 8 carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, cycloheptyl and the like. The “C3-C8 halocycloalkyl group” is, for example, one or more 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 cyclic structure substituted by a halogen atom is shown.

  “C1-C3 alkoxy group” refers to, for example, a linear or branched alkoxy group having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy, etc. "Group" refers to a linear or branched alkoxy group having 1 to 4 carbon atoms such as 2-butyloxy in addition to "C1-C3 alkoxy group", and "C1-C3 haloalkoxy group" Is, for example, trifluoromethoxy, 1,1,2-trifluoroethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2- Chloroethoxy, 3-fluoro-n-propyloxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2,3,3,3-hexafluoropropyloxy, 1,1 A linear or branched haloalkoxy group having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 2-trifluoro-2-trifluoromethoxyethoxy; "C1-C4 haloalkoxy group" means, for example, 1,1,2,3,3,3-hexafluoro-n-propyloxy, 1,1,1 in addition to "C1-C3 haloalkoxy group" , 3,3,4,4,4-octafluoro-2-butyloxy, etc., which may be the same or different, each having 1 to 4 linear or branched carbon atoms substituted by one or more halogen atoms Haloalkoxy groups are shown.

  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. “C1-C4 alkylthio group” means, for example, linear or branched carbon such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio in addition to “C1-C3 alkylthio group”. An alkylthio group having 1 to 4 atoms is shown, and “C1-C3 haloalkylthio group” means, for example, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio. One or more halo, which may be the same or different, such as heptafluoro-i-propylthio Represents a straight-chain or branched alkylthio group having 1 to 3 carbon atoms substituted with a C atom, and the “C1-C4 haloalkylthio group” means, for example, in addition to the “C1-C3 haloalkylthio group” Linear or branched chain substituted with one or more halogen atoms which may be the same or different, such as nonafluoro-n-butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio An alkylthio group having 1 to 4 carbon atoms.

  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. Represents a sulfinyl group, and “C1-C3 haloalkylsulfinyl group” means, for example, trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i -Represents 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, such as -propylsulfinyl.

  The “C1-C3 alkylsulfonyl group” is, for example, a linear or branched alkyl having 1 to 3 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like. Represents a sulfonyl group, and the “C1-C3 haloalkylsulfonyl group” includes, for example, trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i. -Represents 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, such as -propylsulfonyl.

  “Arylsulfonyl group” means the number of carbon atoms having an aromatic ring such as phenylsulfonyl, p-toluenesulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl, acenaphthylenylsulfonyl, etc. 6 to 14 arylsulfonyl groups are shown.

  “C1-C4 alkylamino group” means, for example, a linear, branched or cyclic carbon atom such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino, etc. Represents an alkylamino group having a number of 1 to 4, and the “di-C1-C4 alkylamino group” may be the same or different linear chain such as dimethylamino, diethylamino, N-ethyl-N-methylamino, etc. Alternatively, it represents an amino group substituted with two branched alkyl groups having 1 to 4 carbon atoms.

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

  Examples of the “C1-C4 haloalkylcarbonyl group” include fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl, 2,2 , 3,3,3-pentafluoropropionyl and the like, a linear or branched alkylcarbonyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different.

  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.

  Examples of the “C1-C4 perfluoroalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i -Represents a linear or branched alkyl group having 1 to 4 carbon atoms, all substituted with fluorine atoms such as butyl, and the "C2-C6 perfluoroalkyl group" includes, for example, pentafluoroethyl, hepta Fluorine atoms such as fluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, undecafluoro-n-pentyl, tridecafluoro-n-hexyl Linear or branched carbon atoms, all substituted by It shows the alkyl group.

  Examples of the “C1-C6 perfluoroalkylthio group” include trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro- A linear or branched alkylthio group having 1 to 6 carbon atoms which is all substituted with fluorine atoms such as i-butylthio, undecafluoro-n-pentylthio, tridecafluoro-n-hexylthio and the like.

  Examples of the “C1-C6 perfluoroalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2 1 to 1 carbon atoms in a straight or branched chain, all substituted by fluorine atoms such as -butylsulfinyl, nonafluoro-i-butylsulfinyl, undecafluoro-n-pentylsulfinyl, tridecafluoro-n-hexylsulfinyl, etc. 6 alkylsulfinyl groups are shown.

  Examples of the “C1-C6 perfluoroalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2 1 to 1 linear or branched carbon atoms, all substituted with fluorine atoms such as butylsulfonyl, nonafluoro-i-butylsulfonyl, undecafluoro-n-pentylsulfonyl, tridecafluoro-n-hexylsulfonyl, etc. 6 alkylsulfonyl groups are 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.

A ₁ , A ₂ , A ₃ , A ₄ are preferably A ₁ is a carbon atom, a nitrogen atom or an oxidized nitrogen atom, and at the same time A ₂ , A ₃ , A ₄ are all carbon atoms, more preferably _{is, a 1, a 2, a} 3, a 4 are all carbon atoms.
G ₁ is preferably an oxygen atom.
G ₂ is preferably an oxygen atom.
G ₃ is preferably an oxygen atom.
X is preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a fluorine atom.
n is preferably 0, 1, or 2, and more preferably 0 or 1.

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, a pyridyl group, or a halogen atom, C1-C4 alkyl group, C1 having one or more substituents which may be the same or different and selected from a nyloxy group, a C1-C4 alkoxycarbonyl group, and an acetylamino group -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 One or more same selected from di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, acetylamino group Or a pyridyl group having a substituent which may be different,
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 A substituted phenyl group having 1 to 3 identical or different substituents selected from trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, methylamino group, dimethylamino group, cyano group, and 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, trifluoromethyl A sulfinyl group, Trifluoromethyl sulfonyl group, a pyridyl group having a methyl amino group, dimethylamino group, a cyano group, 1 to 2 identical or different and have good substituents selected from nitro groups.

Q ₂ is preferably a phenyl group which may be substituted or a heterocyclic group which may be substituted, and more preferably a general formula (2) (Chemical formula 3) or a general formula (3) (Chemical formula 4). A substituted phenyl group or a substituted pyridyl group represented by:
Among them, Y ₁ and Y ₅ are preferably each independently a 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 group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyano group,
Y ₆ and Y ₉ are each 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, or a tri group. 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 ₂ , Y ₄ and Y ₇ are preferably each independently a hydrogen atom, a halogen atom or a methyl group, more preferably a hydrogen atom,
Y ₃ is preferably pentafluoroethyl group, heptafluoro-n-propyl group, heptafluoro-i-propyl group, nonafluoro-n-butyl group, nonafluoro-2-butyl group, nonafluoro-i-butyl group, trifluoro Methylthio group, pentafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, nonafluoro-n-butylthio group, nonafluoro-2-butylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group , Heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, nonafluoro-n-butylsulfinyl group, nonafluoro-2-butylsulfinyl group, trifluoromethylsulfonyl group, pentafluoro Roethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group, 1,1,2,2-tetrafluoroethoxy 1,1,1,3,3,3-hexafluoro-i-propyloxy group, 1,1,2,3,3,3-hexafluoro-1-propyloxy group, 1,1,2- A trifluoro-2-trifluoromethoxyethoxy group, a pentafluorosulfanyl group,
Y ₈ is preferably pentafluoroethyl group, heptafluoro-n-propyl group, heptafluoro-i-propyl group, nonafluoro-n-butyl group, nonafluoro-2-butyl group, nonafluoro-i-butyl group, trifluoro Methylthio group, pentafluoroethylthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, nonafluoro-n-butylthio group, nonafluoro-2-butylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group , Heptafluoro-n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, nonafluoro-n-butylsulfinyl group, nonafluoro-2-butylsulfinyl group, trifluoromethylsulfonyl group, pentafluoro Roethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoro-i-propylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group, pentafluoroethoxy group, 1,1,2, 2-tetrafluoroethoxy group, 1,1,1,3,3,3-hexafluoro-i-propyloxy group, 1,1,2,3,3,3-hexafluoro-1-propyloxy group, 1 1,2-trifluoro-2-trifluoromethoxyethoxy group.

Preferably, R ₁ and R ₂ are each independently a hydrogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, or an optionally substituted C2 -C4 unsaturated alkyl group, optionally substituted C1-C4 alkoxycarbonyl group, cyano group, substituted C1-C4 alkyl group or -C (= O) C (= O) R ₇ (wherein R ₇ represents an alkyl group which may be substituted or a C1-C4 alkoxy group which may be substituted.

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, more preferably an R _1, 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 -, - S -, - SO ₂ - shows a. ), _- E 2 -R ₆ (wherein, _{E 2} represents a C1-C4 alkyl group, _{R 6} is C3-C8 cycloalkyl, cyano, be the same or different and a halogen atom, C1-C6 A substituted phenyl group having one or more substituents selected from a haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, and a nitro group , A pyridyl group, a halogen atom, a 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 13 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.

In the general formula shown in the following production method, Q ₂ has the meaning described in [1], or the general formula (2)

(Wherein Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ have the same meaning as [3]),
Or general formula (3)

(In the formula, Y ₆ , Y ₇ , Y ₈ and Y ₉ have the same meaning as [3].)
Indicates that
Manufacturing method 1

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₁ , R ₂ , X, n, Q ₂ , Z have the same meaning as [1], L is a halogen atom, a hydroxy group Represents a functional group having a leaving ability such as

1- (i): General formula (19) + General formula (20) → General formula (21)
By reacting the m-nitro aromatic carboxylic acid derivative having a leaving group represented by the general formula (19) with the aromatic amine derivative represented by the general formula (20) in a solvent or without a solvent, the general formula An aromatic carboxylic acid amide derivative having a nitro group represented by (21) 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 (19).

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

  Among the compounds represented by the general formula (19), an aromatic carboxylic acid halide derivative can be easily produced from an aromatic carboxylic acid by a conventional method using a halogenating agent. 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 (21) from the m-nitro aromatic carboxylic acid derivative and the compound represented by the general formula (20) 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 (21), 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 (21) can be produced. Examples of the chloroformate used in this case include isobutyl chloroformate and isopropyl chloroformate. In addition to the chloroformates, diethylacetyl chloride, trimethylacetyl chloride and the like can be used.
Both the method using a condensing agent and the mixed acid anhydride method are not limited to the solvent, reaction temperature, and reaction time described in the above literature, and an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate. What is necessary is just to select suitably temperature and reaction time according to progress of reaction.

1- (ii): General formula (21) → General formula (22)
The aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be led to an aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) by a reduction reaction. Examples of the reduction reaction include a method using a hydrogenation reaction and a method using a metal compound (for example, stannous chloride (anhydride), iron powder, zinc powder, etc.).

  In the former method, the reaction can be carried out in a suitable solvent, in the presence of a catalyst, 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. It can be manufactured efficiently.

  As the latter method, “Organic Synthesis” Coll. Vol. III P.I. According to the conditions described in 453, a method of using stannous chloride (anhydride) as a metal compound can be exemplified.

1- (iii): General formula (22) + General formula (23) → General formula (24)
The present invention represented by the general formula (24) is obtained by reacting the aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) with the compound represented by the general formula (23) in a solvent. 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 (22). The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours. It can also be produced by the method using the condensing agent described in 1- (i) or the mixed acid anhydride method.

1- (iv): General formula (24) + General formula (25) → General formula (26)
By reacting the compound represented by the general formula (24) and the compound having a leaving group represented by the general formula (25) in a solvent or without a solvent, the present invention represented by the general formula (26) Compounds can be produced. Examples of the compound represented by the general formula (25) include substituted alkyl halides such as methyl iodide, ethyl iodide, n-propyl bromide, and chloromethyl methyl ether, and carboxyls 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 (25), an alkylating agent such as dimethyl sulfate or diethyl sulfate may be reacted with the compound represented by the general formula (24). It is possible to produce the compound represented by 26).
Manufacturing method 2

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₁ , R ₂ , X, n, Q ₂ , Z have the same meaning as [1], L is a halogen atom, a hydroxy group And the like, and Hal represents a halogen atom.

2- (i): General formula (27) + General formula (23) → General formula (28)
By using a carboxylic acid having an amino group represented by the general formula (27) as a starting material and reacting with a compound represented by the general formula (23) according to the conditions described in 1- (iii), the general formula ( The carboxylic acids represented by 28) can be produced.

2- (ii): General formula (28) → General formula (29)
The compound represented by the general formula (28) 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 (29) can be produced by a known ordinary method.

2- (iii): General formula (29) + General formula (20)-> General formula (30)
By reacting the compound represented by the general formula (29) and the compound represented by the general formula (20) according to the conditions described in 1- (i), the compound represented by the general formula (30) is obtained. Can be manufactured.

2- (iv): General formula (28) + General formula (20) → General formula (30)
The compound represented by the general formula (28) is reacted with the compound represented by the general formula (20) according to the conditions using the condensing agent described in 1- (i) or the conditions using the mixed acid anhydride method. Thus, the compound represented by the general formula (30) can be produced.
Manufacturing method 3

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , R ₁ , R ₂ , X, n, Q ₂ , Z have the same meaning as [1], L is a desorption of a halogen atom, a hydroxy group, etc. Represents a functional group having a desorption ability.)

3- (i): General formula (31) → General formula (32)
Synthesis p. 463 (1993) and Synthesis p. The compound represented by the general formula (32) can be produced by reacting the compound represented by the general formula (31) with a Lawson reagent according to known conditions described in 829 (1984). Conditions such as solvent and reaction temperature are not limited to those described in the literature.

3- (ii): General formula (32) + General formula (23)-> General formula (33)
By reacting the compound represented by the general formula (32) and the compound represented by the general formula (23) according to the conditions described in 1- (iii), the compound represented by the general formula (33) is obtained. Can be manufactured.
Manufacturing method 4

(Wherein, E is shown a -C ₍₌ G _{1) Q} 1 or _{-C (= G 1) G 2} R 3, A 1, A 2, A 3, A 4, R 1, R 2, R 3 , X, n, Q ₁ and Q ₂ have the same meaning as [1].
From the compound represented by the general formula (34), the compound represented by the general formula (35) and the general formula (36) 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 easily separated and purified by a known separation and purification technique such as silica gel column chromatography.
Manufacturing method 5

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₁ , R ₂ , X, n, Q ₂ , Z have the same meaning as [1], L is a halogen atom, a hydroxy group Represents a functional group having a leaving ability such as

5- (i): General formula (37) → General formula (38)
For example, J. et al. Org. Chem. p. 280 (1958), it is possible to carry out an amination reaction using ammonia to produce a compound represented by the general formula (38). 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- (ii): General formula (38) + General formula (23)-> General formula (39)
By reacting the compound represented by the general formula (38) and the compound represented by the general formula (23) according to the conditions described in 1- (iii), the compound represented by the general formula (39) is obtained. Can be manufactured.
Manufacturing method 6

(Wherein R ₂ represents the same meaning as [1], Y ₁ and Y ₅ represent a hydrogen atom, a methyl group, a chlorine atom, a bromine atom and an iodine atom, respectively, and Y ₂ and Y ₄ represent [3]. And R _f represents a C1-C6 perfluoroalkyl group, and m represents 1 or 2.)

6- (i): General formula (40) + General formula (41) → General formula (42)
J. et al. Fluorine Chem. p. 207 (1994), the aminothiophenol represented by the general formula (40) is reacted with the haloalkyl iodide represented by the general formula (41) to give the formula (42) Can be produced.

  Examples of the haloalkyl iodide represented by the general formula (41) include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro-n-iodide. Butyl, nonafluoroisobutyl iodide, etc. can be shown, These may be used suitably in the range of 1-10 times molar equivalent with respect to the compound represented by General formula (40).

  The solvent used in this step is not limited to the solvent described in the above-mentioned document, and any solvent may be used as long as it does not significantly inhibit the progress of this reaction. For example, aromatic solvents such as water, benzene, toluene, xylene, etc. Group hydrocarbons, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate Alcohols such as methanol and ethanol, ketones such as acetone, methyl isobutyl ketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, 1,3-dimethyl-2-imidazolidinone, Hexamethyl phosphate triami Can show inert solvent such as, these solvents may be used alone or as a mixture of two or more. A polar solvent is particularly preferable. 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.

6- (ii): General formula (42) → General formula (43)
By using an appropriate halogenating agent, a compound represented by the general formula (43) can be produced, for example, see Synth. Commun. p. 1261 (1989).

  Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, etc., and these are compounds represented by the general formula (42) What is necessary is just to use suitably in the range of 1-10 times molar equivalent with respect to.

  In this step, it is possible to use a solvent, but the solvent to be used is not limited to the solvent described in the above-mentioned document, and any solvent may be used as long as it does not significantly inhibit the progress of this reaction. For example, water, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, chain such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane Cyclic ethers, 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-imi Zorijinon, inert solvents such as hexamethylphosphoric triamide can show, these solvents may be used alone or as a mixture of two or more. A polar solvent is particularly preferable. 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.

6- (iii): General formula (43) → General formula (44)
By using an appropriate oxidizing agent, the compound represented by the general formula (44) can be produced, for example, see Tetrahedron Lett. p. 4955 (1994).

  Examples of the oxidizing agent include organic peracids such as m-chloroperbenzoic acid, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetroxide, acyl nitrate, iodine, bromine, N- Examples thereof include bromosuccinimide, iodosylbenzyl, t-butyl hypochlorite and the like.

  The solvent used in this step is not limited to the solvents described in the above documents, and any solvent may be used as long as it does not significantly inhibit the progress of this reaction. These solvents may be used alone or in combination of two or more. Can be used. A polar solvent is particularly preferable. 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.

6- (iv): General formula (43) → General formula (43-2)
By using an appropriate methylating agent, from the compound represented by the general formula (43) to the general formula (43-2) (wherein either Y ₁ or Y ₅ always represents a methyl group). It is possible to produce the compounds represented. In this step, for example, Tetrahedron Lett. p. The method described in 6237 (2000) can be shown.

6- (v): General formula (43-2) → General formula (44-2)
By following the method described in Production Method 6- (iii), a compound represented by General Formula (44-2) (wherein _one of Y ₁ and Y ₅ always represents a methyl group) is produced. can do.

  Moreover, the manufacturing method shown by this invention is suitably selected using the aniline derivative represented by General formula (43), General formula (44), General formula (43-2), General formula (44-2). Thus, the compound of the present invention can be produced.

In the same manner, Y ₁ , Y ₂ , Y ₄ , and Y _{5 in the} general formula shown in Production Method 6 are a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, and a C1-C6 perfluoroalkylsulfonyl group. Can be produced.
Manufacturing method 7

(In the formula, R ₂ represents the same meaning as [1], Y ₁ and Y ₅ represent a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, and an iodine atom, respectively, and Y ₂ and Y ₄ represent [3]. And R _f represents a C1-C6 perfluoroalkyl group, and m represents 1 or 2.)
By following the production method 6 using the compound represented by the general formula (45) as a starting material, the aniline derivative represented by the general formula (47) can be produced, and the production method shown in the present invention is appropriately performed. By selection, it is possible to produce the compounds of the present invention.
In the same manner, Y ₁ , Y ₂ , Y ₄ and Y _{5 in the} general formula shown in Production Method 7 are a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group. Can be produced.
Manufacturing method 8

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , X, n, G ₃ , R ₂ , Q ₂ have the same meaning as [1].)
The compound represented by the general formula (48) can be produced by reacting the compound represented by the general formula (48) 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 within a range of 0.01 to 5 molar equivalents relative to the compound represented by the general formula (48), or may be used as a solvent.

  Examples of the reactant include substituted alkyl halides such as methyl iodide, ethyl iodide, n-propyl bromide, and chloromethyl methyl ether, carboxylic acid halides such as acetyl chloride, chloroacetyl chloride, and benzoyl chloride, and 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 (48).

The reaction temperature may be appropriately selected from −80 ° C. to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.
Manufacturing method 9

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , X, n, G ₃ , R ₁ , R ₂ , Q ₂ have the same meaning as [1].)

9- (i): General formula (22) → General formula (50)
The compound represented by the general formula (22) 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 (50). 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 to be used, and the reaction time may be appropriately selected within the range of several minutes to 96 hours.

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

9- (iii): General formula (22)-> General formula (50) (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 reducing agent, a compound in which R ₁ is a methyl group in the general formula (50) 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 reducing agent 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 10

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ have the same meaning as [1], and Hal represents a halogen atom. .)

10- (i): General formula (22) + General formula (51) → General formula (52)
Tetrahedron Lett. p. According to known conditions described in 3789 (1999) and the like, the compound represented by the general formula (22) is reacted with the compound represented by the general formula (51) to represent the general formula (52). Compounds can be made. Conditions such as solvent and reaction temperature are not limited to those described in the literature.

10- (ii): General formula (52) + General formula (25)-> General formula (53)
By reacting the compound represented by the general formula (52) and the compound represented by the general formula (25) according to the conditions described in 1- (iv), the compound represented by the general formula (53) is obtained. Can be manufactured.
Manufacturing method 11

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ have the same meaning as [1], and Hal represents a halogen atom. .)

11- (i): General formula (54) → General formula (55)
By reacting the compound represented by the general formula (55) with the conditions described in 2- (ii), the compound represented by the general formula (55) can be produced.

11- (ii): General formula (55) + General formula (20)-> General formula (56)
By reacting the compound represented by the general formula (55) and the compound represented by the general formula (20) according to the conditions described in 1- (i), the compound represented by the general formula (55) Can be manufactured.

11- (iii): General formula (54) + General formula (20)-> General formula (56)
The compound represented by the general formula (54) is reacted with the compound represented by the general formula (20) 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 (56) can be produced.
Manufacturing method 12

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₁ , R ₂ , X, n, Q ₂ , Z have the same meaning as [1].)
The compound represented by general formula (26) can be produced by reacting the compound represented by general formula (57) according to the conditions described in 1- (iv).
Also, Journal of Chemical Society Chemical Communications p. 270 (1988) and the like, by reacting the compound represented by the general formula (57) with nitronium tetrafluoroborate, R1 or R2 in the general formula (26) is a nitroso group. The compound was synthesized by Synthesis-Stuttgart p. And reacting the compound represented by the general formula (57) with ammonium nitrate according to known conditions described in 745 (1988) and the like, to produce a compound in which R1 or R2 in the general formula (26) 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 (57) with N-chlorosuccinimide or N-bromosuccinimide, R in the general formula (26) _A compound in which ₁ or R ₂ is a chlorine atom or a bromine atom can be produced. Conditions such as solvent and reaction temperature are not limited to those described in the literature.
Manufacturing method 13

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₂ , X, n, Q ₂ , Z have the same meaning as [1], L is a desorption of a halogen atom, a hydroxy group, etc. Indicates a functional group having desorption ability.)

13- (i): General formula (57) → General formula (58)
A compound represented by the general formula (58) by reacting the compound represented by the general formula (57) with ammonium thiocyanate or alkali metal thiocyanate according to, for example, the conditions described in JP-A-4-270260. Can be manufactured.

13- (ii): General formula (58) → General formula (59)
The compound represented by the general formula (58) is treated under alkaline conditions according to the conditions described in, for example, Organic Synthesis Vol. 31, page 19 (1951). Can be manufactured.

13- (iii): General formula (59) → General formula (60)
A compound represented by the general formula (60) is produced by reacting the compound represented by the general formula (59) with the compound represented by the general formula (23) according to the conditions described in 1- (iii). can do.

  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 7 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, "Ph" is used to represent each a phenyl group.

Below, the physical-property value of the compound represented by General formula (1) of this invention is shown. The shift value of ¹ H-NMR shown here uses tetramethylsilane as an internal reference substance.

The pests in the present invention mean pests in the fields of agriculture and horticulture or livestock and sanitation. The insecticide containing the compound represented by the general formula (1) of the present invention as an active ingredient includes various agricultural and forestry, horticulture, stored grain pests, hygiene pests or nematodes that harm rice plants, fruit trees, vegetables, other crops, and florets. For example, as Lepidoptera, bat moth (Endoclyta excrescens), yellow bat (Endoclyta sinensis), white bat (Palpifer sect. Adoxophys orana fascita), Chanococ spider, Adoxophies sp., Apples spruce (Archips brevipicanus), Midarekacmon Maki (Archips fuscocupreanus), Kakumonhamaki (Archips xylosteanus), Igusashinmushiga (Bactra furfurana), bombardier Baha'i Iroha Maki (Cnephasia cinereipalpana), Kurimiga (Cydia kurokoi), chestnut green sink bur (Eucoenogenes aestuosa), apple co-sink Lee (Grapholita inopinata), Nashihimeshinsukoi (Grapholita molesta), Chamonaki (Homona magnanima), Ooshima Toumaki (Hoshinoa adumbrata), Beansinkigaiga (Leguminivora glycinivorella), Azuki Aya uraeses azukivora), Daizusayamushiga (Matsumuraeses falcana), beans Hime Saya insect moth (Matsumuraeses phaseoli), Kuwahimehamaki (Olethreutes mori), apples high Iroha Maki (Spilonota lechriaspis), apple white Hime moth (Spilonota ocellana), grapes bombardier moth (Eupoecillia ambiguella) , Phylonidosa mesotypa, Artemisia pelvis, Cydia pomonella, Endopiza vitabina, Endopiza vitabina a sp. ), Oominoga (Eumeta japonica), Chaminoga (Eumeta minuscula), carvings (Nemapogon granellus), clothes moth (Tinea translucens), Nashichibiga (Bucculatrix pyrivorella), Momohamoguriga (Lyonetia clerkella), Gin Mont leafminer (Lyonetia prunifoliella), Mamehosoga (Caloptilia soyella ), Chalothosiga (Caloptilia zeivosa), Oyster hosoga (Choptipes diospyrosella), Kinmonhosoga (Phyllonolycter lingonella), Nashihoso (Spulerina astaurota), mandarin orange leafminer (Phyllocnistis citrella), grape leafminer (Phyllocnistis toparcha), Negikoga (Acrolepiopsis sapporensis), yam Koga (Acrolepiopsis suzukiella), diamondback moth (Plutella xylostella), apple Hime sink Lee (Argyresthia conjugella), grapes Sukashiba ( Parathrene regalis, Cosca shiba (Synanthedon vector), Kakinogetamashiga (Stathampoda masinissa), Japanese peach moth (Bracchia triannuella), Cotton bug (Pec) tinophora gossypiella), potato moth (Phthorimaea operculella), peach fruit moth (Carposina niponensis), apple moth black bar (Illiberis pruni), Kuroshitaaoiraga (Latoia sinica), monema flavescens (Monema flavescens), Nashiiraga (Narosoideus flavidorsalis), Aoiraga (Parasa consocia), Himekuroiraga (Scopelodes contracus), Chilo supresalis, Cnaphalocros medinalis, Conogethes puniferiferis , Cotton moth (Diaphania indica), pear moth (Ectomyelois pyrivorella), yellow moth (Ephestia elutella), ephestia kuehima ti Euzophera batogensis), Glyphodes piloalis, Hamelula undalis, Marasmia deigula, Maruca testula, a furnacalis), Azukinomeiga (Ostrinia scapulalis), Fukinomeiga (Ostrinia zaguliaevi), Shibatsutoga (Parapediasia teterrella), Ukon'nomeiga (Pleuroptya ruralis), Indian meal moth (Plodia interpunctella), Sankameiga (Scirpophaga incertulas), parnara guttata (Parnara guttata), Papilio Helenus, Papilio machaon hipporates, Papilio xutus, Monk butterfly (Colias erate poliographus), Papilio butterfly (Pia) ris rapae crucivora), lampides boeticus (Lampides boeticus), Plum Eda Shakti (Angerona prunaria), mugwort Eda Shakti (Ascotis selenaria), Tobi Mont giant Eda Shakti (Biston robustum), Umeedashaku (Cystidia couaggaria), pine moth (Dendrolimus spectabilis), lackey moth (Malacosoma neutria testacea, apple calcare (Odonestis pruni japonensis), hawk moth (Cephonodes hylas), grape sparrow (Acosmerix castanea), clover killer whale (Clostera anacha) ta), kelp killer whale pike (Clostera anastomosis), Mont black killer whale pike (Phalera flavescens), giant Tobi Mont killer whale pike (Phalerodonta manleyi), killer whale pike moth (Stauropus fagi persimilis), Arna Pseudoconspersa (Euproctis pseudoconspersa), Monshirodokuga (Euproctis similis), tussock (Euproctis subflava), Japanese gypsy moth (Lymantria dispar), Japanese cynomolgus moth (Orgyia thyella), Hyphantria cunea, Spirosoma imparilis (Apisoma imparilis) thoplusia agnata), Nakajiroshitaba (Aedia leucomelas), black cutworm (Agrotis ipsilon), Kaburayaga (Agrotis segetum), Wataakakiriba (Anomis flava), Akakiriba (Anomis mesogona), Tamanagin'uwaba (Autographa nigrisigna), Trichoplusia ni (Trichoplusia ni), tobacco budworm ( Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Crested squirrel (Heliothis maritima), Sweet moth (Mamestra brassicae), Butterfly moth (Narranga aescens), Pepper ia separata), Ineyotou (Sesamia inferens), Sujikiriyotou (Spodoptera depravata), beet armyworm (Spodoptera exigua), common cutworm (Spodoptera litura), Ringokenmon (Triaena intermedia), Nashikenmon (Viminia rumicis), Shiromon'yaga (Xestia c-nigrum) and the like, semi As Heteroptera of Hemoptera, Marker bug (Megacopta punctatissimum), Murano beetle (Carpocoris purpureipennis), Spotted beetle (Dolicorumae, E. coli) urydema pulchrum), longer (Eurydema rugosum), Mar Shirahoshi stink bug (Eysarcoris guttiger), giant thorns Shirahoshi bug (Eysarcoris lewisi), thorns Shirahoshi bug (Eysarcoris parvus), Shirahoshi stink bug (Eysarcoris ventralis), Tsuyaaokamemushi (Glaucias subpunctatus), Akasuji Stink bugs (Graphosoma rubrolineatum), Japanese winged bugs (Halyomorpha mistata), Japanese stink bug (Laginotomus elongatas), Red-headed bug (Nezara antenata), Minamia var. , Beet bug (Piezodorus hybneri), Plautia crossota green bug (Plautia stali), rice black bug (Scotinophara lurida), Iwasaki stink bug (Starioides iwasakii), nightshade stink bug (Acanthocoris sordidus), giant spiders helicopter stink bug (Anacanthocoris striicornis), bombardier Hari bug (Cletus puntigger), tiger spider beetle (Cletus trigonus), gossip beetle (Molipteryx fulginosa), beetle spider beetle (Leptocorisa acuta), spider helicopter (Leptocolisae Helico beetle (Leptocorisa oratorius), Hosoheli beetle (Riptortus clavatus), Red beetle beetle (Aeschynteles maculatas), Scarlet beetle (Sorca), Eurasian beetle (Liorhyssus hyalinus) , White-tailed goose bugs (Pachybrachius luridus), black-headed bugs (Paromius exguus),
Toba hemipterus,
Red Hoshi stink bug (Dysdercus cingulatus), Princess red-spotted stink bug (Dysdercus poecilus), Kikugunbai (Galeatus spinifrons), Yanagigunbai (Metasalis populi), Kusugunbai (Stephanitis fasciicarina), Nashigunbai (Stephanitis nashi), Tsutsujigunbai (Stephanitis pyrioides), Himegunbai (Uhlerites debile, walnut grass (Uhlerites latius), bearded turtle (Adelphocoris lineolatus), spotted tiger beetle (Adelphocoris triannulatus), core turtle turtle ( polygus lucorum), blacktip reef shark Blue Kasumi turtle (Apolygus spinolai), red Hoshi Kasumi turtle (Creontiades pallidifer), tobacco Miridae (Cyrtopeltis tennuis), giant black Tobi Miridae (Ectometopterus micantulus), Black Kite Kasumi turtle (Halticiellus insularis), apple black Kasumi turtle (Heterocordylus flavipes) , Yellow turtle (Lygus disponsi), madara kasumika turtle (Lygus saundersi), sugar beet turtle (Orthotylus flavosparsus), wheat turtle (Stenodema calcaratum), futasu Kasumikame (Stenotus binotatus), red streaks Kasumi turtle (Stenotus rubrovittatus), mouse Mont green Miridae (Taylorilygus pallidulus), Trigonotylus caelestialium (Trigonotylus coelestialium), etc., as the Orthoptera (Homoptera), large brown cicada (Graptopsaltria nigrofuscata), Maekiawafuki (Aphrophora costalis ), Pine awafuki (Aphrophora flavipes), grape awafuki (Aphrophora vitis), himefutentenaga wafuki (Clovia punctata), hosoawafuki (Philaenus spumarius), tsumaga Green leafhopper (Bothrogonia japonica), Green leafhopper (Cicellaella viridis), White leafhopper (Cofana spectra), Red leafhopper (Aguriahana baibei), apicalis, Edwardsiana flavescens, Edwardsiana roseae, Empoasca abietis, Empoasca ai brufa), mandarin orange leafhopper (Zyginella citri), lid Ten leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), cross di leafhopper (Nephotettix nigropictus), Taiwan green rice leafhopper (Nephotettix virescens), apple spotted leafhopper (Orientus ishidai), Inazuma leafhopper (Recilia dorsalis), Sorhoanus tritici, Swanusetettix subfusculus, Laodelfax straitellas, Niraparka ata lugens, sugarcane planta (Numata muiri), corn planter (Peregrinus maidori) turkey (Perkinsiella sachacharida), white planthopper (Satella furcifera) Calophya nigridorsalis, Diaphorina citri, Yamasaki lice, Psylla aetii, Psylla pallet, Psylla citrus ca), Apple Whale (Psylla mary), Black Apple Whale (Psylla maryvorella), Psylla pyrisuga, Psylla tobirae, Psylla tobirae (Tr) Aleurocanthus spiniferus), Grape whitefly (Aureurobus taonabae), Tobacco whitefly (Bemisia tabaci), Citrus whitefly (Dialeuroes citria), Onitsunairafira genifolii), grape aphid (Viteus vitifolii), apple aphid (Aphidungis mary), apple pea beetle (Eriosoma lanigerum), sugar beetle (Geoica lucifuga), aphid Aphids (Aphis crancivora), Yanagia aramushi (Aphis farinos yanagicola), Cotton aphids (Aphis gossypii), Potato aphids (Aulacorthum solani), Wheat aphids chrysi), radish aphid (Brevicoryne brassicae), Tulip phylloxera (Dysaphis tulipae), birch cotton butterbur spotted aphid (Euceraphis punctipennis), Momoko butterbur aphid (Hyalopterus pruni), fake radish aphid (Lipaphis erysimi), chrysanthemum Princess aphid (Macrosiphoniella sanborni ), Tulip mustard aphid (Macrosiphum euphorbiae), Broad bean aphid (Megoura crassicauda), Nasikovia aphid (Melanafis siphonella), Apple aphid (Myzus mum) alysuctus, aphid aphid (Myzus mumecola), peach aphid (Myzus persicae), Nephipharumia (Neotoxoptera formosale), euchoemaria aphid (Ovatus malicolens) Rhibopodophyllum rubiabdominalis, Sapphis piria, Schizophis pilicola, Aphidia aphidia on ibarae), Komi can aphid (Toxoptera aurantii), mandarin orange black aphid (Toxoptera citricidus), peach Cobb aphid (Tuberocephalus momonis), Taiwan aphid (Uroleucon formosanum), wheat green aphid (Schizaphis graminum), giant straw sandals scale insects (Drosicha corpulenta ), Icerya purchasi, Matsumotokona scale insect (Crisicoccus matsumotoi), Pine tree scale insect (Crisicoccus pinii), Pseudococcidae (Dysmicoccus wistis) Na scale insects (Planococcus citri), mealybug (Planococcus kraunhiae), mandarin orange Hime mealybugs (Pseudococcus citriculus), mulberry mealybugs (Pseudococcus comstocki), Tsunoroumushi (Ceroplastes ceriferus), Rubiroumushi (Ceroplastes rubens), mandarin orange Hirata scale insects (Coccus discrepans ), Japanese scale insects (Coccus hesperidum), Japanese citrus scales (Coccus pseudomagnoliarum), scallops (Ericerus pela), Japanese caterpillars (Lecanium c) rni), chanochaeta scales (Lecanium persicae), citrus scales (Pulvinaria aurantii), citrus scales (Pulvinaria citricola), stag beetles (Pulvinaria) , Aonidiella aurantii, Aonidiella citrina, Aspidiotus destructor, Aspidiotus hederae, Aphidius Chrysomphalus ficus), no circle scale insects (Comstockaspis perniciosa), black Kata Mar scale insects (Duplaspidiotus claviger), mandarin orange persimmon scale insects (Lepidosaphes beckii), apple oyster scale insects (Lepidosaphes ulmi), no white Naga scale insects (Lopholeucaspis japonica), no black Hoshi scale insects (Parlatoreopsis pyri), Camellia camellia (Parlatoria camelliae), Paramecium aphid (Parlatoria theae), Paramecium scale (Parlatoria ziziphi), Harannagaga Musi (Pinnaspis aspidistrae), mandarin orange circle scale insects (Pseudaonidia duplex), living room Le scale insects (Pseudaonidia paeoniae), white peach scale (Pseudaulacaspis pentagona), plum white scale insects (Pseudaulacaspis prunicola), Yano yanonensis (Unaspis yanonensis), etc., Coleoptera ( COLEOPTERA, Adoretus tenuimaculatus, Douganebubui (Anomala cuprea), Amanala rufucuprea,
Flower chafer (Eucetonia pilifera), Blue flower chafer (Eucetonia roelofsi), Nagachakogane (Heptophylla picea), Kofukikogane (Melolontha japonica), beetles (Mimela splendens), core Oh flower chafer (Oxycetonia jucunda), Japanese beetle (Popillia japonica), varied carpet beetle (Anthrenus verbasci ), Himetsuobushimushi (Attagenus unicoloror japonicus), Tobacco beetle (Lasiderma sericorne), Lyctus bruneus, Carpophilus dim idiatus), clear Keshikisui (Carpophilus hemipterus), giant beetle, Epilachna vigintioctopunctata (Epilachna vigintioctomaculata), the beetle, Epilachna vigintioctopunctata (Epilachna vigintioctopunctata), bean beetle (Epilachna varivestis), Hime mealworm (Alphitobius laevigatus), mealworm (Neatus picipes), hime Polerus ratzeburgi, Paleosus subdepressus, Tenebrio molitor, Tribolium cass taneum), Hirata red flour beetle (Tribolium confusum), beans Beetle (Epicauta gorhami), key sawyer (Aeolesthes chrysothrix), Gomadarakamikiri (Anoplophora malasiaca), Japanese pine sawyer (Monochamus alternatus), Kiboshi beetle (Psacothea hilaris), grapes tiger beetle (Xylotrechus pyrrhoderus), Xytrocera globosa, common bean weevil (Acanthoscelides obectus), Azuki beetle (Callosobruchus chinensis), Japanese beetle llosobruchus maculatus), cucurbit leaf beetle (Aulacophora femoralis), Tenebrio monkey beetle (Basilepta balyi), Kamenokohamushi (Cassida nebulosa), Ten site bi potato beetle (Chaetocnema concinna), Imosaruhamushi (Colasposoma dauricum), A person who spotted neck Naga leaf beetle (Crioceris quatuordecimpunctata), rice Root beetle (Donacia provosti), Luri potato beetle (Linaeidea aenea), Klebion beetle (Luperomorpha tunabrosa), Medicia nigrobilineata, Inedro oem Oulema oryzae), Anthrenus key spring monkey Beetle (Pagria signata), daikon leaf beetle (Phaedon brassicae), Kisujinomihamushi (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa decemlineata), corn rootworm such (Diabrotica sp. ), Plum vest Li weevil (Involvulus cupreus), peach vest Li weevil (Rhynchites heros), sweet potato weevil (Cylas formicarius), apple weevil (Anthonomus pomorum), die consulting weevil (Ceuthorhynchidius albosuturalis), chestnut weevil (Curculio sikkimensis), rice weevil (Echinocnemus squameus), potato weevil (Eusepes postfasciatus), hornworm weevil (Hypera nigrirostris), alfalfa weevil (Hypera posticca), rice weevil weevil rus oryzophilus), vegetable weevil (Listroderes costirostris), apple pea leaf weevil (Phyllobius armatus), Chibi pea leaf weevil (Sitona japonicus), boll weevil (Anthonomus grandis), co-maize weevil (Sitophilus oryzae), maize weevil (Sitophilus zeamais), grass reed weevil ( Sphenophrus venatus vestitus, pinewood beetle (Tomicus piniperda), etc., and the thrips (THYSANOPTERA), the phoenix thrips (Anaphotrips obscurus), and manicatus), tea Roh black thrips (Dendrothrips minowai), Hirazuhanaazamiuma (Frankliniella intonsa), lily flower thrips (Frankliniella lilivora), Croton thrips (Heliothrips haemorrhoidalis), Cosmos thrips (Microcephalothrips abdominalis), soybean thrips (Mycterothrips glycines), mulberry thrips (Pseudodendrothrips mori), Chinese thrips (Sirtotrips dorsalis), Acabia thrips (Selenothrips rubroincinctus), Rice thrips (Stenchaetothrips biformis), leek black thrips (Thrips alliorum), loquat Hana thrips (Thrips coloratus), Yellow Hana thrips (Thrips flavus), Hana thrips (Thrips hawaiiensis), Japanese black Hana thrips (Thrips nigropilosus), Thrips palmi (Thrips palmi ), Citrus black thrips (Franklinella occidentalis), soybean thrips (Thrips setosus), gladiolus thrips (Thrips simplex), thrips tha p atus), Sina Kedah thrips (Haplothrips chinensis), Hana Kedah thrips (Haplothrips kurdjumovi), clover Kedah thrips (Haplothrips niger), CHILLY tailed Kedah thrips (Leeuwenia pasanii), box Kedah thrips (Liothrips floridensis), Yuri Nokuda thrips (Liothrips vaneeckei ), Littotrips pasaniae, Pontocyclops diospyrosi, etc., such as ORTHOPTERA, Periplaneta amberica laneta furiginosa), Periplaneta japonica, German cockroach (Blatella gerapia), Japanese cockroach (Blatella lituricolis), White cockroach ), Locust (Oxya hyla intrichata), locust (Oxya yezoensis), locust grasshopper (Locusta migratoria), etc.,
As for Diptera, Dipera aino, Candida agrestis, Asphondylia sp., D cucurbitae, D , cherry Leaf Spot fruit fly (Rhacochlaena japonica), Inemigiwabae (Hydrellia griseola), rice click Kimi Giwa fly (Hydrellia sasakii), cherry fruit fly (Drosophila suzukii), Inekimoguribae Chlorops oryzae), Mugikimoguribae (Meromyza nigriv ntris), (Agromyza oryzae), the pea (Chromatomyia horticola), eggplant leafminer (Liriomyza bryoniae), green onion leafminer (Liriomyza chinensis), legume leafminer (Liriomyza trifolii), tomato leafminer (Liriomyza sativae), reed Gros leafminer (Liriomyza huidobrensis), Onion flies (Delica antiqua), Delia platura, sugar beet flies (Pegomya unicularia), Black flies (Pormia regina), Musca domespica C piens pallens), Anopheles sinensis (Anopheles sinensis), Aedes albopictus (Aedes albopictus), etc. Culex pipiens (Culex pipiens molestus), as Hymenoptera (Hymenoptera), Nihon turnip sawfly (Athalia japonica), Kaburahabachi (Athalia rosae ruficornis), Ringohabachi (Arge mali ), Arrange pagana, Dryokosmus kuriphilus, Formica japonica, etc., and Acarina (Acarina), Polyphagotarsonemus lala teneotarsonemus pallidus), Microstegium vimineum dust mites (Tarsonemus waitei), Shiramidani (Pyemotes ventricosus), Mugidani (Penthaleus major), grapes Hime spider mite (Brevipalpus lewisi), Chanohimehadani (Brevipalpus obovatus), Pineapple Princess spider mite (Dolichotetranychus floridanus), Kakihimehadani (Tenuipalpus zhizhilashviliae) , Spider spider mite (Brevipalpus phoenicis), Spider spider mite (Tuckerella pavoniformis), Clover spider mite (Bryobia praeiosa) , False clover mites (Bryobia rubrioculus), Anzuhadani (Eotetranychus boreus), Michinokuhadani (Eotetranychus geniculatus), Kurihadani (Eotetranychus pruni), Kono white spider mites (Eotetranychus sexmanaculatus), Smith spider mites (Eotetranychus smithi), Kurumihadani (Eotetranychus uncatus), Suginohadani (Oligonychus hondonensis), Crimson spider mite (Oligonychus ilicis), Larix spider mite (Oligonychus karamatus), Citrus spider mite (Panonychus citri), apple Mites (Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus), kanzawai (Tetranychus kanzawai), two-spotted spider mite (Tetranychus urticae), cherry spider mites (Tetranychus viennensis), tea Roh Naga rust mite (Acaphylla theae), Tulip rust mite (Aceria tulipae), mandarin orange rust mite ( Aculops pelekassi, Acarus fockeii, Acarus schlettendali, Calacarus carinatis, Calabitrimus viti Mite (Epitrimerus pyri), false pear rust mite (Eriophyes chibaensis), Ashibutokonadani (Acarus siro), Mugikonadani (Aleuroglyphus ovatus), the bulb mite, Rhizoglyphus (Rhizoglyphus robini), Tyrophagus (Tyrophagus putrescentiae), house dust mite (Ornithonyssus bacoti), red mites (Leptotrombidium akamushi) , Leptotrophidum scutellaris, Leptotrophium pallidum, etc.,
As Hari nematode eyes (TYLENCHIDA), bentgrass nematode (Anguina agrostis), wheat Tsubu nematode (Anguina tritici), Imogusaresenchuu (Ditylenchus destructor), Nami Ish click nematodes (Tylenchorhynchus claytoni), Martin Ish click nematodes (Tylenchorhynchus martini), Ish click nematodes ( Tylencherhynchus sp.), Hirschmanniella imamuri, Hineschmanniella oryzae, Southern nematode (Pratylenchus coffe) Run Negu Saleh nematode (Pratylenchus convallariae), chrysanthemum Negu Saleh nematode (Pratylenchus fallax), tea Negu Saleh nematode (Pratylenchus loosi), wheat Negu Saleh nematode (Pratylenchus neglectus), Northern Negu Saleh nematode (Pratylenchus penetrans), Negu Saleh nematode (Pratylenchus sp.) , Helicotylenchus dihystera, Helicotylenchus erythrinae, Helicotylenchus sp., Hopollaimus sp. Rotynchulus reniformis, Brachyrum nematode (Scutellonema brachyurum), Barley avenae, Cactodera cisto phde, C Cyst nematode (Heterodera elacista), soybean cyst nematode (Heterodera glycines), clover cyst nematode (Heterodera trifolii), arenaria root-knot nematode (Meloidyne arenaria), camellias Chu (Meloidogyne camelliae), grass root-knot nematode (Meloidogyne graminis), northern root-knot nematode (Meloidogyne hapla), sweet potato root-knot nematode (Meloidogyne incognita), root-knot nematode (Meloidogyne sp. ), Tylenchulus semipenetrans, Aphelenchus avenae, etc., as DORYLAIMIDA, Longidorus martinid, us. Nematode (Xiphinema americanum), Eurasian nematode (Xiphinema sp.), Trichoderus sp., And the like (THYSANURA), tica), termites (ISOPTERA), Cyptotermes domesticus, Cyptotermes formosanus, ReticultermesPetatus, Odontotermes As a flea (SIPHONAPTERA), as a flea (Ctenocephalides canis), etc., as a lice (ANOPLURA), as a head lice (Pediculus humanus humanus), etc. ) As a geji (Thereronema tubeculata), etc., as an arthropod double leg class (DIPLOPODA), as a scallop (Oxidus gracilis), as a mollusc (MOLLUSCA), as against a slug (Incilaria bilineata), etc. It is what you have.

  The insecticide containing the compound represented by the general formula (1) of the present invention as an active ingredient is pest control as it is, or appropriately diluted with water or suspended in order to control various pests. Effective for plants that are expected to generate pests.For example, for pests occurring in fruit trees, cereals, vegetables, etc. , Seed dressing, seed treatment such as calper treatment, soil full-layer treatment, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dressing, rice box treatment, water surface application, etc. It is also possible to use it by absorbing it from the root by treating it in the same manner. In addition, it can be applied to nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection. Furthermore, for example, in addition to spraying on stored grain pests, house pests, sanitary pests, forest pests, etc., they can also be used for application to house building materials, smoke, baits and the like.

  The insecticide containing the compound represented by the general formula (1) of the present invention as an active ingredient is generally used in a form convenient for use according to a conventional method for preparation in agricultural and horticultural medicine. is there. That is, these are mixed in a suitable inert carrier, or if necessary, together with an auxiliary agent in a suitable ratio, dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and an appropriate dosage form, for example, , Suspensions, emulsions, solutions, wettable powders, granules, powders, tablets and the like.

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

  Examples of insecticides, acaricides, and nematicides that can be combined with the compound represented by the general formula (1) of the present invention include azinephos-methyl, acephate, isoxathion, and isoxathion. ), Isofenphos, ethifos, etrimfos, oxydemethon-methyl, oxydeprofos, quinalphos, chlorpyrifolysylchlorphosphine ), Chlorfenvinphos, cyanophos ), Dioxabenzofos, dichlorvos, disulfoton, dimethylvinphos, dimethoate, sulprofos, diazinoni, croton, thiomethon Tetrachlorvinphos, temephos, tebupyrimfos, terbufos, nared, bamidothion, pyraclofos, pyridafenthion (py) pirimiphos-methyl), fenitrothion (fenitothion), fenthion (fenthion), phentoate (flupyrazofos), prothiofos (prothiophos), propofos Phosmet, formothion, formate, malathion, mecarbam, mesulfenfos, methamidophos, metidathion, metidathion Lathiones, parathion-methyl, monocrotophos, trichlorfon, EPN, isazofos, isamifos, isodafos, cadamifos, cadamifos Organic phosphorus insecticides such as thionazine, fenamiphos, fothiazate, fosthietane, phosphocarb, DSP, ethoprophos, anyanicarb arb), aldicarb, isoprocarb, ethiofencarb, carbaryl, carbosulfan, xylylcarb, thiocarb, thicarb Furathiocarb, propoxur, bendiocarb, benfurcarb, methomyl, metocarb, XMC, carbofuran, carbofuran carbamate insecticides such as ycarb) and oxamyl, acrinathrin, allethrin, esfenvalerate, empentrin, cycloprothrin, haloprothrin, haloprothrin, haloprothrin Cyhalothrin, lambda-cyhalthrin, cyfluthrin, beta-cyfluthrin, cypermethrin, alpha cyperthrin (Zeta-cypermethrin), silafluophene (silafluofen), tetramethrin (tetramethrin), tefluthrin (deltamethrin), tralomethrin (trafenthrin), bifenthrin (bifenthrin) (Fenpropathrin), furamethrin, praretrin, flucitrinate, fluvalinate, flubrocylinate, permethrin Synthetic pyrethroid insecticides such as permethrin, resmethrin, etofenprox, and various isomers thereof, cartap, thiocyclam, benzultap insecticides such as benzultap , Acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid, thiamethoxam, thimethnam ), Diflubenzuron, teflubenzuron, triflumuron, novaluron, novifluuron, fluzuron, fluzuron, flutriuron, flutriuron (Flufenoxuron), hexaflumuron, lufenuron, chromafenozide, tebufenozide, halofenozide, methyfenodif de), diophenolan, cyromazine, pyriproxyfen, buprofezin, methoprene, hydroprene, insects, quinoprene, kinoprene, kinoprene , Organochlorine insecticides such as endosulfan, endosulfan, chlorfenson, chlorbenzilate, dicofol, bromopropyrate, acetoprole, fipronil , Ethiprole Phenylpyrazole insecticides such as ethiprole, pyrethrins, rotenone, nicotine sulfate, abamectin, BT agents, spinosad and other insecticidal natural products such as acequinol , Amidoflumet, amitraz, etoxazole, quinomethionate, clofentezine, fenbutatin oxide, diexol spir diclofen, spiromesifen, tetradifon, tebufenpyrad, fenacryl, bifenacrate, bifenazate, biidafate, pyridaben Fenpyroximate, fluacrylpyrim, fluazinam, flufenzine, hexythiazox, propargite, benzomate zomate, polynactin complex, milbemectin, lufenuron, mecarbam, methiocarb, mevinphos, mefenphos, and halfenproxicide (Azadirachtin), diafenthiuron, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate, chlorate Tolfylpyrad, pymetrozine, phenoxycarb, hydramethylnon (di), fluidyl (fluidyl), fluoridyl (fluidyl), fluoridyl (fluidyl). flonicamid, metaflumizole, repimectin, TPIC (tripropropylisocyanate), albendazole, oxybendazole, oxfendazole dazole, trichlamide, fensulfothion, fenbendazole, levamisole hydrochloride, morantel tartrate, sodium damet et al. , Compounds represented by the general formula (A) and the general formula (B).

  Examples of fungicides that can be combined with the compound represented by the general formula (1) of the present invention include triadimefon, hexaconazole, propiconazole, ipconazole, and prochloraz ( prochloraz), triflumizole, tebuconazole, epoxiconazole, difenoconazole, flusilazole, flusilazole. The Quinconazole, bittertanol, tetraconazole, triticonazole, flutriazole, penconazole, penconazole, penconazole, penconazole, penconazole, peniconazole, penconazole, peniconazole. Conmazole, imibenconazole, simconazole, microbutanil, hymexazole, imaretyl, furamil, p Ruthamide, etridiazole, oxpoconazole, oxpoconazole-fumarate, pefurazoate, petrozoazole, prothiazole p Pyrimidine fungicides such as phenifenox, fenarimol, nuarimol, bupirimate, mepanipyrim, cyprodinil, pyridinyl, pyrimethanil, pyrimethanil Metalaxyl (metala Acylalanine fungicides such as xyl), oxadilil, benalaxyl, thiophanate, thiophanate-methyl, benomyl, carbendazizol (carbendizole), carbendazizol (carbendizole) Benzimidazole fungicides such as thiabendazole, bactericidals such as manzeb, propineb, zineb, methylram, maneb, ziram, thiuram Agents, chlorothalonil, etc. Organochlorine fungicides, carboxamide fungicides such as ethaboxam, oxycarboxin, carboxin, flutolanil, silthiofam, mepronil, dimethomol Morpholine fungicides such as fenpropidin, fenpropimorph, spiroxamine, tridemorph, dodemorph, flumorph, and azoxystrobine kresoxim-me hyl), methinostrobin, oryastrostrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin, piroclostrobin (pyrobrostrobin) Strobilurin fungicides such as (picoxyxybin), iprodione, procymidone, vinclozolin, croclozolinate and other dicarboximide fungicides, flusulfammidet, flusulfamdomet Methyl isothiocyanate, chloropicrin, metasulfocarb, hydroxyisoxazole, hydroxyisoxazole, p-hydroxy-dazole Soil fungicides such as 3-dichloropropene and metham-sodium, basic copper chloride, basic copper sulfate, copper nonylphenolate sulfur sulfite Copper disinfectants such as copper-oxidate, DBEDC, anhydrous copper sulfate (copper sulfate anhydride), copper sulfate pentahydrate, copper hydroxide, inorganic sulfur, Wet sulfur, calcium sulfate, zinc sulfate, fentin, sodium hydrogen carbonate, potassium hydrogen suboxide Inorganic fungicides such as sodium chlorate and silver metal, Organophoric fungicides such as fenfos, tolclofos-methyl, fosetyl, iprobenfos, dinocap, pyrazophos, and carpropamide (carpropalide) Melanin biosynthesis inhibitor fungicides such as tricyclazole, pyroquilon, diclocymet, phenoxanil, kasugamycin, validamycin validamicin Gin S (bl antibiotics such as stcidin-S), oxytetracycline, mildiomycin, streptomycin, rapeseed oil, natural oils such as machine oil, and machine oil Carbamate fungicides such as benthiavalcarb-isopropyl, iprovalicarb, propamocarb, diethofenil, fluorimide, fluorimide Fungicide, quinoxyfen, quinolinic fungicides such as oxolinic acid, chlorothalonil, captan, phthalimide / phthalonitrile fungicides such as folpet, probenazole (Probenazole), acibenzoral S-methyl, tiadinil and other plant activators that induce disease resistance of plants, cyflufenamide, fenhexamide, diflumetrim, diflumetrim Metraphenone, picobenamide (picoben) amide), proquinazide, famoxadone, cyazofamid, fenamidone, zoxamide, boscalid, mosadil Dichrofluidid, triforine, isoprothiolane, ferrimzone, diclomezine, teclophthalam, pencylthionate, quincyclothione, quincyclone ionate), iminoctadin acetate (iminoctadin-triacetate), iminoctaine albecylate (iminoctadine-albesilate), ambam amobam, polycarbamate, i thidiachine, thidiazin Guazatine, dodecylguanidine-acetate, quintozene, tolylfluanid, anilazine, nitrotal-isopropyl Fenitoropan (fenitropan), Jimechirimoru (dimethirimol), Bench azole (benthiazole), harpin protein (harpin protein), Furumetoba (flumetover), Mandy prop bromide (mandipropamide), penthiopyrad (penthiopyrad), and the like. Some of the compounds listed above can take stereoisomers, but these isomers are also included in the present invention.

  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 to the above insecticides and fungicides, the compound represented by the general formula (1) is mixed with herbicides, fertilizers, soil conditioners, plant growth regulators and other plant protective agents and materials, and further effective. Can be made, and a composition that can 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 1-1]
Production of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide 20.0 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine were added to 100 ml of tetrahydrofuran at room temperature. To the stirred solution, 13.0 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran was slowly added dropwise. After stirring at room temperature for 10 hours, ethyl acetate and water were added to the reaction solution. After performing the liquid separation operation, the organic phase was separated and dried over anhydrous magnesium sulfate. This solution is filtered, the filtrate is collected, and the solvent is distilled off under reduced pressure. The residue obtained is washed with a mixed solvent of hexane-diisopropyl ether to obtain 26.0 g of the desired product (yield 85%). Was obtained as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 2.33 (6H, s), 7.37 (2H, s), 7.68 (1H, s), 7.72 (1H, t, J = 8. 1 Hz), 8.28 (1 H, d, J = 8.1 Hz), 8.44 (1 H, dd, J = 1.2, 8.1 Hz), 8.75 (1 H, t, J = 1.2 Hz) )

[Example 1-2]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-aminobenzamide 0.90 g of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide, stannous chloride To a solution obtained by adding 1.56 g of anhydride to 25 ml of ethanol and stirring at room temperature, 2 ml of concentrated hydrochloric acid was added and stirred at 60 ° C. for 1 hour. After returning to room temperature, the reaction solution was poured into water and neutralized with potassium carbonate. Ethyl acetate was added and the insoluble material was removed by filtration. The organic phase was separated and dried over anhydrous magnesium sulfate. The solution was filtered, the filtrate was collected, and the residue obtained by distilling off the solvent under reduced pressure was washed with n-hexane to give 0.44 g (yield 53%) of the desired product as a white solid. Got as.
¹ H-NMR (CDCl ₃ , ppm) δ 2.34 (6H, s), 3.87 (2H, broadcast), 6.86-6.89 (1H, m), 7.20-7.35 ( 6H, m)

[Example 1-3]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (benzoylamino) benzamide N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-aminobenzamide 0.25 g, pyridine 0.09 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran was added dropwise to a solution of 0.06 g added to 5 ml of tetrahydrofuran and stirred at room temperature. After stirring at room temperature for 1 hour, ethyl acetate and 1N hydrochloric acid were added, and the organic phase was separated. The organic phase was washed once with saturated aqueous sodium hydrogen carbonate and then dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, the solvent was distilled off under reduced pressure, and the precipitated solid was washed with diisopropyl ether to obtain 0.29 g (yield 92%) of the desired product as a white solid. .
¹ H-NMR (DMSO-d ₆ , ppm) δ 2.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d , J = 7.8 Hz), 7.98-8.01 (2H, m), 8.12 (1H, d, J = 7.3 Hz), 8.34 (1H, s), 8.87 (1H) , S), 9.66 (1H, s).

[Example 1-4]
Production of N- (2,6-dimethyl-4-heptafluoroisopropyl) -N-methoxycarbonylphenyl 3- (N-benzoyl-N-methoxycarbonyl-amino) benzamide (Compound No. 1-1)
A solution of 0.04 g of 60% sodium hydride suspended in 5 ml of DMF was charged dropwise with 0.20 g of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (benzoylamino) benzamide at room temperature. did. After stirring for 30 minutes at room temperature, 0.08 g of methyl chloroformate was charged. Subsequently, after stirring at room temperature for 4 hours, ethyl acetate and water were added to the reaction solution. The organic phase was separated, washed once with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 8: 1) to obtain 0.06 g (yield 25%) of the desired product as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 2.31 (6H, s), 3.67 (3H, s), 3.70 (3H, s), 7.36 (2H, s), 7.43 -7.56 (5H, m), 7.61 (1H, s), 7.68-7.74 (3H, m).

[Example 2-1]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl 3-nitrobenzamide A solution of 0.18 g of 60% sodium hydride suspended in 15 ml of tetrahydrofuran was dissolved in 5 ml of tetrahydrofuran. 2.0 g of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide was added dropwise at room temperature. After stirring for 30 minutes at room temperature, 0.65 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was added dropwise. Subsequently, after heating up to 50 degreeC and stirring for 4 hours, it returned to room temperature and added ethyl acetate and water to the reaction solution. The organic phase was separated, washed once with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to obtain 1.73 g (yield 84%) of the desired product as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 2.31 (6H, s), 3.38 (3H, s), 7.27 (2H, s), 7.37 (1H, t, J = 7.8 Hz) ), 7.62-7.65 (1 H, m), 8.05 (1 H, t, J = 2.0 Hz), 8.11-8.14 (1 H, m).

[Example 2-2]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl 3-aminobenzamide N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl 3-nitrobenzamide A solution prepared by adding 1.50 g, 0.15 g of 10% palladium-carbon to 20 ml of methanol was stirred for 2 hours under a hydrogen atmosphere under normal pressure. After removing the catalyst by filtration, the solvent was distilled off under reduced pressure. Next, the precipitated solid was washed with n-hexane to obtain 1.24 g (yield 88%) of the target product as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 2.27 (6H, s), 3.31 (3H, s), 3.80 (2H, broadcast), 6.40-6.43 (1H, m), 6.54-6.58 (1H, m), 6.71 (1H, t, J = 2.0 Hz), 6.76-6.86 (1H, m), 7.22 (2H, s).

[Example 2-3]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl 3- (methoxycarbonylamino) benzamide N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl The title product was prepared according to the conditions described in Example 1-3 using 3-aminobenzamide and methyl chloroformate. White solid.
¹ H-NMR (CDCl ₃ , ppm) δ 2.25 (6H, s), 3.31 (3H, s), 3.70 (3H, s), 6.49 (1H, s), 6.88 (1H, d, J = 7.8 Hz), 7.03 (1H, t, J = 7.8 Hz), 7.19 (2H, s), 7.34-7.35 (2H, m).

[Example 2-4]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl 3- (N-benzoyl-N-methoxycarbonylamino) benzamide (Compound No. 1-7)
N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl-N-methyl 3- (methoxycarbonylamino) benzamide and benzoyl chloride were used to produce the title product according to the conditions described in Example 1-4. did. Oily substance.
¹ H-NMR (CDCl ₃ , ppm) δ 2.22 (6H, s), 3.31 (3H, s), 3.63 (3H, s), 7.10 (1H, t, J = 7. 8Hz), 7.16-7.22 (3H, m), 7.34-7.43 (6H, m), 7.62 (1H, s).

[Example 3-1]
Preparation of N-benzyl-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide 0.50 g of (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide was added dropwise at room temperature. After stirring for 1 hour at room temperature, 0.20 g of benzyl bromide dissolved in 5 ml of tetrahydrofuran was added dropwise. Subsequently, after heating up to 50 degreeC and stirring for 4 hours, it returned to room temperature and added ethyl acetate and water to the reaction solution. The organic phase was separated, washed once with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was washed with diisopropyl ether to give the desired product (0.33 g, yield 55%) as a white solid.

[Example 3-2]
Preparation of N-benzyl-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (benzoylamino) benzamide N-benzyl-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3 The title product was prepared according to the method described in Examples 1-2 and 1-3 using nitrobenzamide and benzoyl chloride.

[Example 3-3]
Preparation of N-benzyl-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- [N-propargyl-N- (2-fluorobenzoyl) amino] benzamide N-benzyl-N- (2,6 -Dimethyl-4-heptafluoroisopropyl) phenyl 3- (benzoylamino) benzamide and propargyl bromide were used to produce the title product according to the method described in Example 2-1.

[Example 3-4]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- [N-propargyl-N- (benzoyl) amino] benzamide (Compound No. 1-174)
N-benzyl-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- [N-propyn-2-yl-N- (2-fluorobenzoyl) amino] benzamide 0.30 g, 10% palladium- A solution obtained by adding 0.10 g of carbon to 10 ml of methanol was stirred at 45 ° C. in a hydrogen atmosphere for 6 hours. After removing the catalyst by filtration, the solvent was distilled off under reduced pressure. Subsequently, the obtained residue was purified by silica gel (Fuji Silysia Chemical NH silica) column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 0.09 g (yield 35%) of the target product as a white solid. Obtained.
¹ H-NMR (CDCl ₃ , ppm) δ 2.22 (6H, s), 2.24 (1H, t, J = 2.4 Hz), 4.73 (2H, d, J = 2.4 Hz), 7.00-7.45 (9H, m), 7.80-7.95 (2H, m), 9.91 (1H, s).

[Example 4-1]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (methylamino) benzamide 20 ml of 98% sulfuric acid was stirred at room temperature and N- (2,6-dimethyl-4-heptafluoroisopropyl) 3.0 g of phenyl 3-aminobenzamide was added. After stirring for 15 minutes, 10 ml of 37% aqueous formaldehyde solution was added dropwise over 2 hours so as to maintain 35 ° C. The solution was transferred to 100 ml of ice water and extracted with ethyl acetate (50 ml × 3 times). The organic phase was washed with 1N aqueous sodium hydroxide solution (100 ml × 2 times), dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (n-hexane: acetic acid). Purification with ethyl = 4: 1) gave 2.7 g (yield 88%) of the desired product as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 2.35 (6H, s), 2.91 (3H, s), 6.82 (1H, d, J = 7.3 Hz), 7.18-7.52 (7H, m).

[Example 4-2]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- [N-benzoyl-N-methyl-amino] benzamide N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- The title product was prepared using (methylamino) benzamide and benzoyl chloride according to the conditions described in Example 1-3. White solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ 2.20 (6H, s), 3.45 (3H, s), 7.23-7.30 (5H, m), 7.43-7.45 (4H, m), 7.73-7.76 (2H, m), 9.88 (1H, s).

[Example 4-3]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) -N-methoxycarbonyl-phenyl 3- (N-methyl-N-benzoyl-amino) benzamide (Compound No. 1-46)
N- (2,6-Dimethyl-4-heptafluoroisopropyl) phenyl 3- (N-methyl-N-benzoyl-amino) benzamide and methyl chloroformate according to the conditions described in Example 2-1 The thing was manufactured.
¹ H-NMR (CDCl ₃ , ppm) δ 2.21 (6H, s), 3.54 (3H, s), 3.65 (3H, s), 7.19-7.25 (3H, m) , 7.28-7.38 (7H, m), 7.48 (1H, d, J = 7.8 Hz).

[Example 5-1]
Preparation of 4- (heptafluoro-n-propylthio) aniline 5.91 g of 1-iodoheptafluoro-n-propane was added to 20 ml of an acetonitrile solution of 1.25 g of 4-aminothiophenol and 1.11 g of triethylamine. Stir for hours. After diluting with ether, it was washed with 1N aqueous sodium hydroxide solution and purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to obtain 1.85 g (yield 63%) of the desired product. .
¹ H-NMR (CDCl ₃ , ppm) δ 3.95 (2H, s), 6.66 (2H, d, J = 8.8 Hz), 7.40 (2H, d, J = 8.8 Hz).

[Example 5-2]
Preparation of 2,6-dibromo-4- (heptafluoro-n-propylthio) aniline To a solution of 0.77 g of 4- (heptafluoro-n-propylthio) aniline in 15 ml of N, N-dimethylformamide was added N-bromosuccinate. 0.98 g of acid imide was charged. After stirring at 60 ° C. for 2 hours, ether and water were added to separate the organic phase. The organic phase was washed twice with water and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 9: 1). Purification gave 1.19 g (yield 100%) of the desired product as a red oil.
¹ H-NMR (CDCl ₃ , ppm) δ 4.98 (2H, broadcast-s), 7.66 (2H, s).

[Example 5-3]
2. Preparation of N- {2,6-dibromo-4- (heptafluoro-n-propylthio)} phenyl 2-chloro-3-nitrobenzamide 2,6-dibromo-4- (heptafluoro-n-propylthio) aniline To a solution obtained by adding 6 g to 15 ml of pyridine and stirring at room temperature, 2-chloro-3-nitrobenzoyl chloride prepared from 5.0 g of 2-chloro-3-nitrobenzoic acid and 3.3 g of thionyl chloride was added. After stirring at 60 ° C. for 4 hours, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in ethyl acetate and washed with 1N hydrochloric acid aqueous solution and 1N sodium hydroxide aqueous solution. The residue obtained by evaporating the solvent under reduced pressure was dissolved in 15 ml of methanol, 1.0 g of sodium hydroxide was added, and the mixture was stirred at room temperature. After diluting with ethyl acetate, it was washed with 1N aqueous sodium hydroxide solution and purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1 → 2: 1) to give 1.7 g of the desired product (yield 33). %).
¹ H-NMR (CDCl ₃ , ppm) δ 7.58 (1H, t, J = 7.8 Hz), 7.63 (1H, s), 7.92 (1H, dd, J = 1.5, 7 .8 Hz), 7.98 (2H, s), 7.99 (1H, s).

[Example 5-4]
Preparation of N- {2,6-dibromo-4- (heptafluoro-n-propylthio)} phenyl 3-amino-2-chloro-benzamide N- {2,6-dibromo-4- (heptafluoro-n-propylthio) )} Phenyl 2-Chloro-3-nitrobenzamide was used to produce the title product according to the conditions described in Example 1-2.
¹ H-NMR (CDCl ₃ , ppm) δ 4.29 (2H, s), 6.91 (1H, dd, J = 2.5, 7.3 Hz), 7.16-7.22 (2H, m ), 7.52 (1H, s), 7.94 (2H, s).

[Example 5-5]
Preparation of N- (2,6-dibromo-4-heptafluoro-n-propylthio) phenyl 3- (bis (benzoyl) amino) -2-chloro-benzamide (Compound No. 5-27)
N- {2,6-dibromo-4- (heptafluoro-n-propylthio)} phenyl 3-amino-2-chloro-benzamide (0.11 g) and pyridine (0.02 g) were added to tetrahydrofuran (5 ml) and the resulting solution was stirred at room temperature. 0.03 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran was added dropwise. After stirring at room temperature for 1 hour, ethyl acetate and 1N hydrochloric acid were added, and the organic phase was separated. The organic phase was washed once with saturated aqueous sodium hydrogen carbonate and then dried over anhydrous magnesium sulfate. The solution was filtered, the filtrate was collected, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1). 0.04 g (29% yield) was obtained as a white solid.
¹ H-NMR (CDCl ₃ , ppm) δ 7.25-7.31 (3H, m), 7.38 (1H, t, J = 8.3 Hz), 7.52 to 7.56 (3H, m ), 7.62 (1H, t, J = 7.3 Hz), 7.72 (2H, d, J = 7.3 Hz), 7.91 (2H, d, J = 7.3 Hz), 7.92 (2H, s), 8.56 (1H, s), 8.63 (1H, d, J = 7.8 Hz).

[Example 6-1]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (thioureido) benzamide N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-prepared in Example 1-2 Aminobenzamide (2.04 g) was added to a mixed solvent of 15 ml of xylene and 0.3 ml of water and stirred at room temperature. Next, 0.5 g of sodium thiocyanate and 0.3 ml of concentrated hydrochloric acid were added, and the mixture was stirred at 90 ° C. for 2 hours. On the way, 0.3 ml of concentrated hydrochloric acid was added twice. After returning to room temperature, ethyl acetate and water were added to separate the organic phase, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 1.26 g (yield 54%) of the desired product as a white solid.
¹ H-NMR (DMSO-d ₆ , ppm) δ 2.28 (6H, s), 7.44 (2H, s), 7.50 (1H, d, J = 7.8 Hz), 7.71- 7.75 (2H, m), 7.96 (1H, s), 9.89 (1H, s), 9.95 (1H, s).

[Example 6-2]
Preparation of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (cyanoamino) benzamide 0.50 g of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (thioureido) benzamide 0.6 g of potassium hydroxide was added to a mixed solvent of 15 ml of water and 7 ml of dioxane, and stirred at 110 ° C. Next, 0.45 g of lead acetate trihydrate was charged. After stirring at 110 ° C. for 5 minutes, the mixture was bathed in ice and the resulting precipitate was filtered off. After acetic acid was added to the filtrate for neutralization, the resulting precipitate was collected by filtration and washed with diisopropyl ether to obtain 0.40 g (yield 85%) of the desired product.
¹ H-NMR (DMSO-d ₆ , ppm) δ 2.28 (6H, s), 7.19 (1H, d, J = 8.3 Hz), 7.44 (2H, s), 7.52- 7.56 (2H, m), 7.68 (1H, d, J = 8.3 Hz), 10.05 (1H, s), 10.46 (1H, s).

[Example 6-3]
Production of N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- [N ′-(2,2,2-trichloroethoxycarbonyl-N′-cyano) amino] benzamide (Compound No. 2-208)
Follow the conditions described in Example 1-3 using N- (2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3- (cyanoamino) benzamide and 2,2,2-trichloroethyl chloroformate as starting materials. Thus, the target product was produced.
¹ H-NMR (CDCl ₃ , ppm) δ 2.35 (6H, s), 4.96 (2H, s), 7.37 (2H, s), 7.42 (1H, s), 7.67 (1H, t, J = 7.8 Hz), 7.73 (1H, d, J = 7.8 Hz), 7.97 (1H, d, J = 7.8 Hz), 8.08 (1H, s) .
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 1-1, 1-7, 1-23, 1-46, 1-50, 1-52, 1-53, 1-55, 1-173, 1-174, 1- 206, 1-207, 1-208, 1-420, 1-424, 1-426, 1-427, 2-208, 2-209, 2-263, 2-264, 4-32 are 70% or more. The death rate was shown.

[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, compound numbers 1-1, 1-7, 1-23, 1-46, 1-50, 1-52, 1-53, 1-55, 1-420, 1-424, 1- 426, 2-263, 2-264, 4-32 showed a death rate of 70% or more.

[Test Example 3]
Insecticidal test against Japanese brown planthopper (Laodelfax straellatus) Acetone solution diluted with a predetermined concentration of a test compound was sprayed on rice seedlings and air-dried, and then 10 Japanese brown planthoppers were used. All drugs were used as the drug substance. The sample was left in a constant temperature room at 25 ° C., and the number of living insects was examined 6 days after the treatment. It was carried out by 10 animals in 1 ward.
As a result, at 1000 ppm, Compound Nos. 1-23, 1-53, 1-174, 2-209, 4-32 showed a death rate of 70% or more.

Claims (5)

General formula (1)

{In the formula, A ₁ , A ₂ , A ₃ and A ₄ each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom, and Z represents —C (═G ₁ ) Q ₁ , —C ( = G ₁ ) G ₂ R ₃ , —SO ₂ Q ₁ or —Q ₁ (In the formula, G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom, and Q ₁ and R ₃ each independently Or an optionally substituted alkyl group, an optionally substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group; and G ₃ represents oxygen Represents an atom or a sulfur atom, X may be the same or different, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group, n represents an integer of 0 to 4, and Q ₂ represents Optionally substituted phenyl group, substituted Good naphthyl group, optionally substituted tetrahydronaphthyl radical or indicates an optionally substituted heterocyclic group,, R _1, R ₂ are each independently a hydrogen atom, an oxygen atom, a halogen atom, hydroxy group, Nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, may be substituted A good C2-C4 unsaturated alkyl group, an optionally substituted C1-C4 alkoxycarbonyl group, an optionally substituted C1-C4 alkenyloxycarbonyl group, an optionally substituted C1-C4 alkynyloxycarbonyl group, Optionally substituted phenoxycarbonyl group, optionally substituted 1-C4 alkylaminocarbonyl group, C1-C4 alkylcarbonyloxy group which may be substituted, benzoyl group which may be substituted, C1-C4 alkoxy group which may be substituted, C1 which may be substituted -C4 alkylthio group, C1-C4 alkylsulfinyl group which may be substituted, C1-C4 alkylsulfonyl group which may be substituted, benzenesulfonyl group which may be substituted, benzylsulfonyl group which may be substituted , An optionally substituted benzyl group, a substituted C1-C4 alkyl group, a substituted C1-C4 alkylcarbonyl group or —C (═O) C (═O) R ₇ (wherein R ₇ is a substituted group) And an optionally substituted alkyl group or an optionally substituted C1-C4 alkoxy group. Wherein R ₁ and R ₂ are both hydrogen atoms, both C1-C4 alkyl groups, both C1-C4 alkylcarbonyl groups, both C1-C4 haloalkylcarbonyl groups, a combination of hydrogen atoms and C1-C4 alkyl groups, Combination of hydrogen atom and C1-C4 alkylcarbonyl group, combination of hydrogen atom and C1-C4 haloalkylcarbonyl group, combination of C1-C4 alkyl group and C1-C4 alkylcarbonyl group, C1-C4 alkyl group and C1-C4 haloalkylcarbonyl A combination of groups, or a combination of a C1-C4 alkylcarbonyl group and a C1-C4 haloalkylcarbonyl group.)}. In general formula (1),
R ₁ and R ₂ are each independently a hydrogen atom, oxygen atom, halogen atom, hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, C1-C4 alkyl group, C1- C4-haloalkyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C1-C4 alkoxycarbonyl group , C1-C4 haloalkoxycarbonyl group, C1-C4 alkenyloxycarbonyl group, C1-C4 alkynyloxycarbonyl group, phenoxycarbonyl group, or the same or different, halogen atom, C1-C6 alkyl group, C1-C6 Haloalkyl group, C3-C8 Chloalkyl 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 Group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyl An oxy group, a substituted phenoxycarbonyl group having one or more substituents selected from a C1-C4 alkoxycarbonyl group, a C1-C4 alkylaminocarbonyl group, a C1-C4 haloalkylaminocarbonyl group, a C1-C4 alkylcarbonyl Nyloxy group, 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 halocyclo group Alkyl 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxy A substituted benzoyl group having one or more substituents selected from a sicarbonyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a benzyloxycarbonyl 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 haloalkylthio group , C1-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 C1-C4 halo A substituted benzyloxycarbonyl group having one or more substituents selected from an alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1- C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, benzenesulfonyl group, or 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 alkyls Finyl 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, C1-C4 haloalkyl A substituted benzenesulfonyl group having one or more substituents selected from a carbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a benzylsulfonyl 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 haloalkyl group O group, C1-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 alkyl A substituted benzylsulfonyl group having one or more substituents selected from a carbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl 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, C3-C8 halocycloalkyl group, C1-C6 al Alkoxy group, or indicates shown) C1-C6 haloalkoxy group, _(wherein, R 1, _{R 2} are both hydrogen atoms, both C1-C4 alkyl group, both C1-C4 alkyl group, both C1-C4 haloalkylcarbonyl group A combination of a hydrogen atom and a C1-C4 alkyl group, a combination of a hydrogen atom and a C1-C4 alkylcarbonyl group, a combination of a hydrogen atom and a C1-C4 haloalkylcarbonyl group, a combination of a C1-C4 alkyl group and a C1-C4 alkylcarbonyl group A combination of a C1-C4 alkyl group and a C1-C4 haloalkylcarbonyl group, or a combination of a C1-C4 alkylcarbonyl group and a C1-C4 haloalkylcarbonyl group),
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
Z is _{-C (= G 1) Q 1} , -C (= G 1) G 2 R 3, -SO 2 Q 1 or -Q ₁
(In the formula, G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
Q ₁ and R ₃ are each independently 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, C3 -C8 cycloalkyl group, C3-C8 halocycloalkyl group, phenyl 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 alkyl Sulfonyl group, C1-C6 haloalkylsulfonyl group, One or more selected from the following: a group, a nitro group, a hydroxy group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group A substituted phenyl group having a substituent, a naphthyl group, or 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 Haloalkylsulfoni 1 selected from a group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted naphthyl group and heterocyclic group having the above substituents (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group) 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)), or 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, a 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, pentafluoro A substituted heterocyclic group having one or more substituents selected from a sulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (wherein The heterocyclic group is pyridyl group Pyridine-N-oxide group, pyrimidinyl 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 is shown. ),
-E ₁ -Z ₁ -R ₄
Wherein 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, C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C8 cycloalkyl group. , C3-C8 halocycloalkyl group, phenyl 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 A substituent having one or more substituents selected from 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 Phenyl group, naphthyl group, or 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 tro 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 Substituted naphthyl group, heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group) Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group), or the same or different, Logen 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, pentafluorosulfanyl group, C1 -A substituted heterocyclic group having one or more substituents selected from a C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group. Group is pyridyl group, pyridine -N-oxide, pyrimidinyl, pyridazyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrole A 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
(Wherein 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 may be a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, the same or different, a halogen atom, a C1-C6 alkyl group, a 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group C1-C4 alkylcal A phenyl group, a substituted phenyl group having one or more substituents selected from a C1-C4 alkoxycarbonyl group, a naphthyl group, which may be the same or different, a halogen atom, a C1-C6 alkyl group, a 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1- C4 alkylcal A substituted naphthyl group having one or more substituents selected from a nyloxy group, a C1-C4 alkoxycarbonyl group, or a heterocyclic group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, Pyridazyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrole, imidazolyl, triazolyl, pyrazolyl Group, or a tetrazolyl 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, C1 -C6 Al Xi 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 1 or more selected from cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted heterocyclic groups having the following substituents (wherein the heterocyclic groups are pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyrani group) Le A xazolyl 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. ). ). ) And
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. A C1-C6 haloalkoxy group, a C1-C6 haloalkyl group optionally substituted with one or more hydroxyl groups, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group 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, pentafluorosulfur Nyl group, Fe Nyl 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 halo Alkoxy 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, phenyl group which may be substituted with pentafluorosulfanyl group, thienyl group, halogen atom which may be the same or different, C1-C6 alkyl group, C1-C6 haloalkyl group C3-C8 cycloal 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 , A C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxy group, or a thienyl group optionally substituted with a pentafluorosulfanyl group. A substituted phenyl group having one or more substituents, a naphthyl group, or 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 halocyclo Alkyl group, C1-C6 alkoxy Group, C1-C6 haloalkoxy group, C1-C6 haloalkyl group optionally substituted with one or more hydroxyl groups, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkyl group A substituted naphthyl group having at least one substituent selected from a sulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, and a pentafluorosulfanyl group, a heterocyclic group ( The heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group , Imidazolyl group, triazolyl Represents a ru group, a pyrazolyl group, or a tetrazolyl group. Or may be the same or different, and may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or one or more hydroxyl groups. C1-C6 haloalkyl 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 heterocyclic group having one or more substituents selected from a nitro group, a hydroxy group, and a pentafluorosulfanyl group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group) , Furyl group, thienyl group, oxazolyl group, isoxazolyl Oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolyl group, or tetrazolyl group.), Tetrahydronaphthalene group, or the same or different, halogen atom, C1-C6 alkyl Group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 haloalkyl group optionally substituted with one or more hydroxyl groups, C1-C6 alkylthio group, C1-C6 haloalkylthio group 1 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 substituent of the above,
The compound of claim 1. In general formula (1),
Z is _{-C (= G 1) Q 1} , -C (= G 1) G 3 R 3, -SO 2 Q 1 or -Q ₁
(In the formula, G ₁ and G ₃ each independently represent an oxygen atom or a sulfur atom,
R ₃ is 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, a C3- C8 halocycloalkyl group, phenyl 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, hydroxyl group Substituted phenyl having one or more substituents selected from Si group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Group, naphthyl group, or 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, Substituted naphthyl having one or more substituents selected from droxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Group, heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group) Group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group), or the same or different, 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, pentafluorosulfanyl group, C1-C4 A substituted heterocyclic group having one or more substituents selected from an alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (wherein the heterocyclic group is pyridyl Group, pyridine-N-oxide group , Pyrimidinyl 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, A triazolyl group, a pyrazolyl group, or a tetrazolyl group is shown. ),
-E ₁ -Z ₁ -R ₄
Wherein 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, C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C8 cycloalkyl group. , C3-C8 halocycloalkyl group, phenyl 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 A substituent having one or more substituents selected from 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 Phenyl group, naphthyl group, or 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 tro 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 Substituted naphthyl group or heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyrani group) Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group or tetrazolyl group)), or the same or different Well, 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, pentafluorosulfanyl group , A substituted heterocyclic group having one or more substituents selected from a C1-C4 alkylcarbonyl group, 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, 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 is shown. ),
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. ),
-E ₂ -R ₆
(Wherein 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 may be 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, a C1-C6 alkyl group, a 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, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl Group, C1-C4 al A substituted phenyl group having one or more substituents selected from a kill carbonyloxy group, a C1-C4 alkoxycarbonyl group, a naphthyl group, or 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, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group , C1- A substituted naphthyl group having one or more substituents selected from a 4-alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a heterocyclic group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group) 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 , 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, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group. , C1- 6 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 1 selected from a group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 alkoxycarbonyl group Substituted heterocyclic groups having the above substituents (the heterocyclic groups here are pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydro group) Pirani A benzoyl 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. ). )
Q ₁ is 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- C6-cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl Sulfinyl 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 alkylcarbonyloxy group, C1 -C4 alkoxycarbonyl group, acetylamino group, substituted phenyl group having one or more substituents which may be the same or different selected from phenyl group, heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine -N-oxide, pyrimidinyl, pyridazyl, pyrazyl, furyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, imidazolyl, triazolyl, pyrrole, pyrazolyl, or tetrazolyl 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 -C6 cycloalkyl group, C3-C6 halo A loalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, 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 alkylcarbonyloxy group, C1-C4 alkoxy A substituted heterocyclic group having one or more substituents which may be the same or different selected from a carbonyl group, an acetylamino group and a phenyl group (the heterocyclic group here is a pyridyl group, a pyridine-N-oxide group, Pyrimidinyl group, pyridazyl group, pyrazyl group, Lil group, a thienyl group, an oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group. ). ) And
Q ₂ represents the general formula (2)

Wherein Y ₁ and Y ₅ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl 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, a C1-C3 haloalkylsulfonyl group or a cyano group,, _{Y 3} is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group or a pentafluorosulfanyl group; Y ₂ and Y ₄ are each independently Hydrogen atom, halogen atom, Or a C1-C4 alkyl group.) Or a general formula (3)

Wherein Y ₆ and Y ₉ are each independently a halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl 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 or a cyano group, _{Y 8} is C1-C4 haloalkoxy group, A C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group or a pentafluorosulfanyl group, Y ₇ is a hydrogen atom, a halogen atom Or a C1-C4 alkyl group Shown.) Represented by A compound according to claim 2.   An insecticide comprising the compound according to any one of claims 1 to 3 as an active ingredient.   Use of a drug characterized in that an effective amount of the compound according to any one of claims 1 to 3 is treated on a target useful crop or soil in order to protect the useful crop from pests. Method.