JP2010047478A - Pest control composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new pest control composition which can simultaneously control pests that can not or hardly be controlled by one of insecticides, miticides and fungicides. <P>SOLUTION: There is provided the pest control composition characterized by comprising a compound represented by general formula (1) or (5) (wherein: A<SB>1</SB>, A<SB>2</SB>, A<SB>3</SB>, A<SB>4</SB>are each C, N or oxidized N; R<SB>1</SB>, R<SB>2</SB>are each independently H, 1 to 4C alkyl, 1 to 4C alkylcarbonyl; G<SB>1</SB>, G<SB>2</SB>are each independently O or S; X groups are identically or differently H, halogen, 1 to 3C alkyl, or trifluoromethyl), and a known insecticide, a known miticide or a known fungicide as active ingredients. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

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

  The pamphlet of International Publication No. 2005/021488 and the pamphlet of International Publication No. 2005/073165 include descriptions of insecticides and their usage.

Further, International Publication No. 2003/008372 pamphlet, International Publication No. 2005/042474 pamphlet, and Pesticide Manual (Thirst Edition) describe insecticides, acaricides and fungicides.
International Publication No. 2005/021488 Pamphlet International Publication No. 2005/073165 Pamphlet International Publication No. 2003/008372 Pamphlet International Publication No. 2005/042474 Pamphlet The pestiside manual

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

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

  As a result of intensive studies to solve the above problems, the present inventors have obtained one or more compounds selected from compounds represented by the general formula (1) or the general formula (5), A combination of one or two or more compounds selected from known insecticides, known acaricides, or known fungicides has been found to efficiently control a plurality of pests, and the present invention has been completed. It is a thing.

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

{Wherein A ₁ , A ₂ , A ₃ , A ₄ each represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
R ₁ and R ₂ each independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, amino group, cyano group, nitro group, hydroxy group, C1-C4 alkyl Carbonyl group, C1-C4 haloalkylcal Nyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, One or more substituents selected from a C1-C4 alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group or a phenyl group, which may be the same or different. A substituted phenyl group having,
A carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, an anthracenyl group, or a norbornyl group);
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, amino group, cyano group, nitro group, hydroxy group, C1-C4 alkyl Carbonyl group, C1-C4 haloalkylcal Nyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, One or more substituents selected from a C1-C4 alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group or a phenyl group, which may be the same or different. A substituted carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, an anthracenyl group or a norbornyl group) ),
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, an acridinyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, amino group, cyano group, nitro group, hydroxy group, C1-C4 alkyl Carbonyl group, C1-C4 haloalkylcal Nyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, One or more substituents selected from a C1-C4 alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group or a phenyl group, which may be the same or different. Substituted heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group) Group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl Group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, acridinyl group or dihydropyranyl group. And
Q ₂ represents a carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group. Show)
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted carbocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The carbocyclic group here represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group.
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, benzimidazolyl group or dihydropyranyl group).
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is a pyrazinyl group, a pyridin-2-yl group, a pyridin-4-yl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, Oxadiazo Group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, Indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, benzoimidazolyl group or dihydropyranyl group are shown. ),
A C1-C6 alkyl group,
Halogen atom, 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 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 Haloa Killcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy A substituted C1-C6 alkyl group having one or more substituents which may be the same or different and selected from a group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group,
Group represented by general formula (2)

(Wherein Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Halogen atom, 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 haloalkylcarbonyl group, C1-C4 alkylcarbonyl Oxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 group Substituted C1-substituted by one or more substituents which may be the same or different and selected from a killsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group or an alkylsilyl group A C6 alkyl group,
C1-C6 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-C6 An alkoxy group, a C1-C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
A C1-C6 haloalkyl group optionally substituted by one or more hydroxyl groups,
A C1-C6 haloalkyl group optionally substituted with one or more C1-C6 haloalkyl groups,
A C1-C6 haloalkyl group optionally substituted with one or more alkoxy groups,
A C1-C6 haloalkyl group optionally substituted by one or more haloalkoxy groups,
A C1-C6 alkylthio group,
A C1-C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
A C1-C6 alkylsulfinyl group,
A C1-C6 haloalkylsulfinyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfinyl group,
A C1-C6 alkylsulfonyl group,
A C1-C6 haloalkylsulfonyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfonyl group,
C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group,
C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, cyano group, nitro group Group, hydroxy group, pentafluorosulfanyl group, carboxyl group, carbamoyl group, C1-C3 alkylaminocarbonyl group, phenylazo group, pyridyloxy group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted pyridyloxy group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group. However,
Y ₁ and Y ₅ may be the same or different,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1 In the case of -C3 haloalkylsulfonyl group or cyano group,
Except for the case where Y ₃ is a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group. ),
Or a group represented by the general formula (3)

(Wherein Y ₆ , Y ₇ , Y ₈ and Y ₉ may be the same or different,
Hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group A C3-C8 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, an optionally substituted C1-C6 haloalkyl group, or an optionally substituted alkoxy group. Good C1-C6 haloalkyl group, C1-C6 haloalkyl group optionally substituted with one or more haloalkoxy groups, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkyl Sulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloa Killsulfonyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, Cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group.
However, Y ₆ and Y ₉ may be the same or different, and are a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group. , A C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, or a cyano group, Y ₈ represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1- The case where it is a C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group is excluded. )
Indicates. } As an active ingredient, one or two or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides or known fungicides are contained. A pest control composition characterized by the above.

[2] The compound represented by the general formula (1) is represented by the general formula (1):
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ and Y ₅ may be the same or different,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, or a C1-C6 alkyl group,
Y ₃ is a trifluoromethyl group, a C1-C6 perfluoroalkoxy group, a pentafluorosulfanyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A -C6 haloalkylsulfinyl group, or
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A -C6 haloalkylsulfonyl group is shown. )
The pest control composition according to the above [1], which is a compound represented by the formula:

[3] The compound represented by the general formula (1) is a compound represented by the general formula (1):
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ is a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 haloalkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkoxycarbonyl group, a C1- C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, or halogen atom, 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 group Alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, arylsulfonyloxy A C1-C4 alkyl group substituted by one or more substituents, which may be the same or different, selected from a group, a pentafluorosulfanyl group or an alkylsilyl group,
Y ₅ is,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Y ₃ is a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group,
Trifluoromethyl group, C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfinyl group,
Or substituted with one or more substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A substituted C1-C6 haloalkylsulfonyl group is shown. )
The pest control composition according to the above [1], which is a compound represented by the formula:

[4] The compound represented by the general formula (1) is represented by the general formula (1):
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, Or a C1-C6 haloalkylsulfonyl group,
Y ₅ is,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Y ₃ represents a halogen atom. )
The pest control composition according to the above [1], which is a compound represented by the formula:

[5] The compound represented by the general formula (1) is a compound represented by the general formula (1):
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (4)

_(Wherein, Y 1, _{Y 5} may be the same or different,
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, nitro group,
Y ₂ and Y ₄ may be the same or different and each represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,
Ra represents a halogen atom or a hydroxy group,
Rb and Rc can each independently represent a halogen atom or a C1-C6 haloalkyl group, and at least one of Rb and Rc has at least one hydrogen atom, hydroxy group, chlorine atom, bromine atom, or iodine atom. Have )
The pest control composition according to the above [1], which is a compound represented by the formula:

[6]
In the general formula (1) R _1, at least one of R ₂ is a C1-C4 alkyl group, wherein [1] to pest control composition according to any one of [5].

[7]
General formula (5)

{Wherein A ₁ , A ₂ , A ₃ , A ₄ each represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
Z represents —N (R ₁ ) SO ₂ Q ₁ or —N (R ₁ ) Q ₁ ;
R ₁ and R ₂ each independently represent a hydrogen atom, a C1-C4 alkyl group, or a C1-C4 alkylcarbonyl group,
G ₁ represents an oxygen atom or a sulfur atom,
X may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, an amino group or a phenyl group ,
Carbocyclic group (the carbocyclic group here means a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group). ,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted carbocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The carbocyclic group here represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group.
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocycle having one or more substituents which may be the same or different and are selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, an amino group or a phenyl group Group (the heterocyclic group here is a pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, Thiazolyl, thiadiazolyl, pyrrole, imidazolyl, triazolyl, pyrazolyl, tetrazolyl, benzothiazolyl, benzoxazolyl, benzofuranyl, benzothiophenyl, quinolyl, isoquinolyl, indolyl, isoindolyl, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group).
Q ₂ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Carbocyclic group (the carbocyclic group here means a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group). ,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted carbocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The carbocyclic group here represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group.
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group).
A C1-C6 alkyl group,
Alternatively, a halogen atom, 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 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 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy Group, C1- 4-haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyl A substituted C1-C6 alkyl group having one or more substituents, which may be the same or different, selected from an oxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group. } As an active ingredient, one or two or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides or known fungicides are contained. A pest control composition characterized by the above.

[8] Known insecticide, known acaricide or known fungicide is azinephos methyl, acephate, isoxathion, isofenphos, ethione, etrimphos, oxydimethone methyl, oxydeprophos, quinalphos, chlorpyrifos, chlorpyrifosmethyl, chlorfenvinphos , Cyanophos, Dioxabenzophos, Dichlorvos, Disulfoton, Dimethylvinphos, Dimethoate, Sulprofos, Diazinon, Thiometone, Tetrachlorvinfos, Temefos, Tebupyrimfos, Terbufos, Nared, Bamidthione, Pyraclophos, Pyridafenthione, Pirimiphosmethyl, Fenitrothion, Fentione, Fentoate , Fencerfothion, Flupirazophos, Prothiophos, Propafos, Profenofos, Hoxime, Hosalon Phosmet, formothione, folate, malathion, mecarbam, mesulfenphos, methamidophos, metidathion, parathion, methylparathion, monocrotophos, trichlorphone, O-ethylphenyl-4-phosphinethiophosphinethiophosphinethiophosphinethiophosphinethiophosphine , Hosthiethane, phosphocarb, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate, etoprophos, alanicarb, aldicarb, isoprocarb, etiophencarb, carbaryl, carbosulfan, xylylcarb, thiodicarb Fenobucarb, furthiocarb, propoxyl, bendiocarb, benfuracarb, mesomil, metorcarb, 3,5-xylylmethylcarbamate, carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate, empentrin, cycloprothrin, cyhalothrin, cyhalothrin , Lambda siharthrin, cyfluthrin, beta cyfluthrin, cypermethrin, alpha cypermethrin, zeta cypermethrin, silafluophene, tetramethrin, tefluthrin, deltamethrin, tralomethrin, bifenthrin, phenothrin, fenvalerate, fenpropatoline, framethrin fluretrin Nate, fulvalinate, fulbrosine line , Permethrin, resmethrin, metofluthrin, dimefluthrin, profluthrin, etofenprox, cartap, thiocyclam, benzltape, acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid, thiamethoxam, nitenpyram, flufluzuron, flufluzuron, flufluzuron , Bistrifluron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyphenozide, diophenolan, cyromazine, pyriproxyfen, buprofezin, methoprene, hydroprene, quinoprene, triazamate, endo Chlorfenson, chlorbenzilate, dicophore, bromopropyrate, acetoprole, fipronil, etiprole, pyrethrin, rotenone, nicotine sulfate, abamectin, Bacillus thuringiensis, spinosad, acequinosyl, amidoflumet, amitraz, etoxazole, quinomethionate Fentedine, fenbutaine oxide, dienochlor, cyhexatin, spirodiclofen, spiromesifen, tetradiphone, tebufenpyrad, binapacryl, bifenazate, pyridaben, pyrimidifene, phenazaquin, phenothiocarb, fenpyroximate, fluacrylpyrim, fluazinam, flufenzine, propaltiazotine Body, milbemectin, le Phenuron, mecarbam, methiocarb, mevinphos, formethanate, halfenprox, azadirachtin, diafenthiuron, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate, chlorfenapyr, tolfenpyrad, pymetrozine, phenoxycarb, hydramethylnon , Hydroxypropyl starch, pyridalyl, flufenelim, flubendiamide, flonicamid, metaflumizone, repimectin, Tripropyrisocyclic, levamisole hydrochloride, morantel tartrate, dazomet, metam sodium,
General formula (AA)

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

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

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

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. The pesticidal composition according to any one of [1] to [7], which is a compound represented by the formula:

[9] Known insecticides, known acaricides or known fungicides are fenitrothion, fenthion, isoxathione, acephate, buprofezin, pyriproxyfen, silafluophene, dinotefuran, imidacloprid, etofenprox, halfenprox, thiamethoxam, clothianidin, acetamiprid, Nitenpyram, thiacloprid, benfuracarb, mesomil, fenobucarb, spinosad, pymetrozine, chromafenozide, lepimectin, fipronil,
General formula (AA)

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

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

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

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. ] The pest control composition as described in said [8] which is a compound represented by these.

[10]
Any one of said [1]-[9] characterized by containing 0.001-95 weight% of 1 or more types of compounds selected from a well-known insecticide, a well-known acaricide, or a well-known fungicide, respectively. A pest control composition as described in 1. above.

[11]
A method for controlling pests, which comprises applying the pest control composition according to [10] above to a pest or a habitat of the pest.

[12]
A method for preventing damage by pests, which comprises applying the pest control composition according to [10] to plant seeds.

[13]
A method for preventing damage by pests, which comprises contacting the plant pests with the pest control composition according to [10] above.

[14]
The prevention method according to [13], wherein the method of contacting the plant seed is spraying treatment, smearing treatment, dipping treatment, or powder coating treatment on the seed.

[15]
Plant seeds are corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper and rape seed, taro, potato, The prevention method according to the above [12], which is a potato, konjac seed, edible lily or tulip bulb.

[16]
The prevention method according to [15], wherein the plant seed is a transformed seed.

[17]
Plant seeds to which the pesticidal composition according to the above [10] is applied.

[18]
A method for preserving plant seeds, comprising applying the pest control composition according to the above [10] to plant seeds.

[19]
The preservation method according to the above [18], wherein the application method to the plant seed is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment or fumigation / smoke treatment.

[20]
A method for preserving a crop, which comprises applying the pest control composition according to the above [10] to a crop of an agricultural plant.

[21]
The storage method according to [20], wherein the application method to the harvested crop of the agricultural plant is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment, fumigation / smoke treatment, or pressure injection.

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

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

  Examples of the “C1-C3 alkyl group” include linear or branched alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, and cyclopropyl. As the “C1-C4 alkyl group”, in addition to the “C1-C3 alkyl group”, for example, n-butyl, s-butyl, i-butyl, t-butyl, etc. Examples of the “C1-C6 alkyl group” include “C1-C4 alkyl group”, for example, n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2- Examples thereof include linear or branched alkyl groups having 1 to 6 carbon atoms such as hexyl, 4-methyl-2-pentyl, and 3-methyl-n-pentyl.

  Examples of the “C1-C3 haloalkyl group” include 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-propi 1,1,1-trifluoro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1 , 3,3,3-hexafluoro-2-chloro-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl, heptafluoro-n-propyl, 1- 1 linear or branched carbon atom substituted with one or more halogen atoms which may be the same or different, such as bromo-1,1,2,3,3,3-hexafluoro-2-propyl To 3 alkyl groups, and examples of the “C1-C4 haloalkyl group” include 4-fluoro-n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl in addition to the “C1-C3 haloalkyl group”. And 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 ruthenium, and the “C1-C6 haloalkyl group”. In addition to the “C1-C4 haloalkyl group”, one or more halogen atoms which may be the same or different, for example, 6,6,6-trifluoro-n-hexyl, nonafluoro-n-butyl, nonafluoro-2-butyl and the like And a linear or branched alkyl group having 1 to 6 carbon atoms substituted by the above.

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

  Examples of the “C2-C4 alkynyl group” include a linear or branched chain having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc. An alkynyl group having 2 to 4 carbon atoms, and examples of the “C2-C4 haloalkynyl group” include a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. And a linear or branched alkenyl group having 2 to 4 carbon atoms.

  Examples of the “C3-C8 cycloalkyl group” include cycloalkyl groups having 3 to 8 carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, cycloheptyl and the like. Examples of the “C3-C8 halocycloalkyl group” include one or more which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like. And a cycloalkyl group having 3 to 8 carbon atoms having a cyclic structure substituted with a halogen atom.

  Examples of the “C1-C3 alkoxy group” include linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy, etc., and “C1-C4 Examples of the “alkoxy group” include 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”. Examples of the group include 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-hexafluoropropyl And 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 pyroxy, and the like, “C1-C4 haloalkoxy group” For example, 1,1,2,3,3,3-hexafluoro-n-propyloxy, 1,1,1,3,3,4,4, in addition to “C1-C3 haloalkoxy group” Examples thereof include a linear or branched haloalkoxy group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 4-octafluoro-2-butyloxy.

  Examples of the “C1-C3 alkylthio group” include linear or branched alkylthio groups having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, and cyclopropylthio. As the “C1-C4 alkylthio group”, in addition to the “C1-C3 alkylthio group”, for example, a linear or branched chain such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio, etc. Examples thereof include an alkylthio group having 1 to 4 carbon atoms. The “C1-C6 alkylthio group” includes, for example, a linear or branched chain such as n-pentylthio and n-hexylthio in addition to the “C1-C4 alkylthio group”. And an alkylthio group having 1 to 6 carbon atoms.

  Examples of the “C1-C3 haloalkylthio group” include trifluoromethylthio, pentafluoroethylthio, 2-fluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-. Substituted by one or more halogen atoms, which may be the same or different, such as propylthio, 1,1,2,2-tetrafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio Examples thereof include a linear or branched alkylthio group having 1 to 3 carbon atoms, and the “C1-C4 haloalkylthio group” includes, for example, nonafluoro-n-butylthio in addition to the “C1-C3 haloalkylthio group”. , Nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio or the like And a linear or branched alkylthio group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be present, and “C1-C6 haloalkylthio group” includes “C1-C4”. In addition to “haloalkylthio group”, for example, linear or branched carbon substituted by one or more halogen atoms which may be the same or different, such as perfluoro-n-pentylthio, perfluoro-n-hexylthio and the like Examples thereof include an alkylthio group having 1 to 6 atoms.

  Examples of the “C1-C3 alkylsulfinyl group” include linear or branched alkyl having 1 to 3 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like. Examples of the “C1-C6 alkylsulfinyl group” include “C1-C3 alkylsulfinyl group”, for example, n-butylsulfinyl, t-butylsulfinyl, n-pentylsulfinyl, n-hexylsulfinyl and the like. Examples thereof include a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms.

  Examples of the “C1-C3 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, 1 , 1,2,2-tetrafluoroethylsulfinyl, 1,1,2,3,3,3-hexafluoropropylsulfinyl, etc., a straight chain substituted with one or more halogen atoms which may be the same or different Or a branched alkyl sulfinyl group having 1 to 3 carbon atoms, and examples of the “C1-C6 haloalkylsulfinyl group” include, in addition to “C1-C3 haloalkylsulfinyl group”, for example, nonafluoro-n-butylsulfinyl, Nonafluoro-s- Substituted with one or more halogen atoms, which may be the same or different, such as tilsulfinyl, 4,4,4-trifluoro-n-butylsulfinyl, perfluoro-n-pentylsulfinyl, perfluoro-n-hexylsulfinyl, etc. And straight-chain or branched alkylsulfinyl groups having 1 to 6 carbon atoms.

  Examples of the “C1-C3 alkylsulfonyl group” include linear or branched alkyl having 1 to 3 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like. Examples of the “C1-C6 alkylsulfonyl group” include “C1-C3 alkylsulfonyl group”, for example, n-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl, n-hexylsulfonyl and the like. Examples thereof include a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms.

  Examples of the “C1-C3 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, 1 , 1,2,2-tetrafluoroethylsulfonyl, 1,1,2,3,3,3-hexafluoropropylsulfonyl, etc., a straight chain substituted by one or more halogen atoms which may be the same or different Or a branched alkylsulfonyl group having 1 to 3 carbon atoms, and examples of the “C1-C6 haloalkylsulfonyl group” include, in addition to the “C1-C3 haloalkylsulfonyl group”, for example, nonafluoro-n-butylsulfonyl, Nonafluoro-s-butylsulfonyl, 4,4 Linear or branched chain substituted by one or more halogen atoms which may be the same or different, such as 4-trifluoro-n-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-hexylsulfonyl, etc. And an alkylsulfonyl group having 1 to 6 carbon atoms.

  Examples of the “arylsulfonyloxy group” include phenylsulfonyloxy, p-toluenesulfonyloxy, 1-naphthylsulfonyloxy, 2-naphthylsulfonyloxy, anthrylsulfonyloxy, phenanthrylsulfonyloxy, acenaphthylenylsulfonyloxy and the like. And an arylsulfonyl group having 6 to 14 carbon atoms having an aromatic ring.

  Examples of the “C1-C4 alkylamino group” include linear, branched or cyclic carbon atoms such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino and the like. Examples of the “di-C1-C4 alkylamino group” include linear chains that may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino, and the like. And an amino group substituted with two alkyl groups having 1 to 4 carbon atoms in the form of a branched or branched chain.

  Examples of the “C1-C4 perfluoroalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i -Linear or branched alkyl groups having 1 to 4 carbon atoms, all substituted with fluorine atoms such as butyl, etc., and examples of the "C2-C6 perfluoroalkyl group" include pentafluoroethyl, Fluorine such as heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, undecafluoro-n-pentyl, tridecafluoro-n-hexyl Linear or branched carbon, all substituted by atoms Include child number 2-6 alkyl groups.

  Examples of the “C1-C6 perfluoroalkylthio group” include trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro- Examples thereof include linear or branched alkylthio groups having 1 to 6 carbon atoms which are 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. There are 6 alkylsulfinyl groups.

  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. Six alkylsulfonyl groups are mentioned.

  Examples of the “alkylsilyl group” include a linear or branched alkyl group having a silicon atom such as a methylsilyl group, a trimethylsilyl group, and an ethylsilyl group.

  The compound represented by the general formula (1) or the general formula (5) may contain one or more asymmetric carbon atoms or asymmetric centers in the structural formula, and two or more kinds of optical isomerism may occur. The compound represented by the general formula (1) or the general formula (5) includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio. . In addition, the compound represented by the general formula (1) or the general formula (5) may have two or more geometric isomers derived from a carbon-carbon double bond in the structural formula. The compound represented by the general formula (1) or the general formula (5) includes all geometric isomers and a mixture containing them in an arbitrary ratio.

  Examples of the compound represented by the general formula (1) or the general formula (5) include compounds having the following atoms or groups as preferable compounds.

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.

R ₁ is preferably a hydrogen atom or a C1-C4 alkyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.

R ₂ is preferably a hydrogen atom or a C1-C4 alkyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
G ₁ and G ₂ are preferably both oxygen atoms.
n is preferably 0, 1, or 2, and more preferably 0 or 1.

  X is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom.

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-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl Group, C1-C4 alkylcarbo A substituted phenyl group having one or more substituents which may be the same or different, selected from a nyloxy group, a C1-C4 alkoxycarbonyl group, and an acetylamino group;
Pyridyl group, or halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cyclo Alkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 alkyl Carbonyloxy group, C1-C Alkoxycarbonyl group, a substituted pyridyl group having one or more identical or different optionally be substituent selected from acetylamino group.

More preferably as Q _1,
Phenyl group,
Fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, A substituted phenyl group having 1 to 3 identical or different substituents selected from a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group, and a nitro group;
Pyridyl group,
Fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, A substituted pyridyl group having 1 to 2 substituents which may be the same or different and selected from a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group.

Q ₂ is preferably a substituted phenyl group or a substituted pyridyl group represented by the general formula (2), the general formula (3) or the general formula (4), and in the case of the general formula (2), (I)
Y ₁ and Y ₅ may preferably be the same or different, and may be a fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-butyl group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyano group,
Y ₂ and Y ₄ are preferably hydrogen atoms,
Y ₃ is preferably a trifluoromethyl group, a pentafluorosulfanyl group,
1,1,2,3,3,3-hexafluoropropoxy group, 2,2,2-trifluoro-1-trifluoromethylethoxy group, 2-trifluoromethoxy-1,1,2-trifluoroethoxy group 1,1,2,2-tetrafluoroethoxy group,
1,1,2,3,3,3-hexafluoropropylthio group, 2,2,2-trifluoro-1-trifluoromethylethylthio group, 2-trifluoromethoxy-1,1,2-trifluoro An ethylthio group, a 1,1,2,2-tetrafluoroethylthio group,
1,1,2,3,3,3-hexafluoropropylsulfinyl group, 2,2,2-trifluoro-1-trifluoromethylethylsulfinyl group, 2-trifluoromethoxy-1,1,2-trifluoro Ethylsulfinyl group, 1,1,2,2-tetrafluoroethylsulfinyl group,
1,1,2,3,3,3-hexafluoropropylsulfonyl group, 2,2,2-trifluoro-1-trifluoromethylethylsulfonyl group, 2-trifluoromethoxy-1,1,2-trifluoro An ethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group,
Or
(Ii)
Y ₁ is preferably
Hydroxymethyl group, methoxymethyl group, methylthiomethyl group, methylsulfinylmethyl group, methylsulfonylmethyl group, acetyl group, trifluoroacetyl group, acetoxy group, ethylcarbonyloxy group, trifluoroacetoxy group, methoxycarbonyl group, ethoxycarbonyl group Acetylamino group, trifluoroacetylamino group, methylsulfonyloxy group, trifluoromethylsulfonyloxy group,
Y ₅ is preferably a fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-butyl group, trifluoromethyl group, methylthio group. Group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyano group,
Y ₂ and Y ₄ are preferably hydrogen atoms,
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, trifluoromethyl group, 1,1,2, 3,3,3-hexafluoropropoxy group, 2,2,2-trifluoro-1-trifluoromethylethoxy group, 2-trifluoromethoxy-1,1,2-trifluoroethoxy group, 1,1,2 , 2-tetrafluoroethoxy group,
1,1,2,3,3,3-hexafluoropropylthio group, 2,2,2-trifluoro-1-trifluoromethylethylthio group, 2-trifluoromethoxy-1,1,2-trifluoro An ethylthio group, a 1,1,2,2-tetrafluoroethylthio group,
1,1,2,3,3,3-hexafluoropropylsulfinyl group, 2,2,2-trifluoro-1-trifluoromethylethylsulfinyl group, 2-trifluoromethoxy-1,1,2-trifluoro Ethylsulfinyl group, 1,1,2,2-tetrafluoroethylsulfinyl group,
1,1,2,3,3,3-hexafluoropropylsulfonyl group, 2,2,2-trifluoro-1-trifluoromethylethylsulfonyl group, 2-trifluoromethoxy-1,1,2-trifluoro An ethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group,
(Iii)
Y ₁ is preferably a trifluoromethoxy group, pentafluoroethyl group, trifluoromethylthio group, pentafluoroethylthio group, heptafluoropropylthio group, heptafluoroisopropylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group , Heptafluoropropylsulfinyl group, heptafluoroisopropylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoropropylsulfonyl group, heptafluoroisopropylsulfonyl group,
Y ₅ is preferably fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, trifluoromethoxy group, pentafluoroethyl group, trifluoromethylthio group, pentafluoroethylthio group, heptafluoropropylthio group , Heptafluoroisopropylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, heptafluoropropylsulfinyl group, heptafluoroisopropylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoropropylsulfonyl group, hepta A fluoroisopropylsulfonyl group,
Y ₂ and Y ₄ are preferably hydrogen atoms,
Y ₃ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom,
In the case of the general formula (4), Y ₁ and Y ₅ may be the same or different, and may be a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, i-propyl group, n-butyl group, 2-butyl group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyano group And
Y ₂ and Y ₄ are preferably hydrogen atoms,
It is preferable that Ra is a bromodifluoro group, Rb is a fluorine atom, Rc is a trifluoromethyl group, or Ra is a chlorodifluoro group, Rb is a hydroxy group, and Rc is a chlorodifluoromethyl group.

  Examples of the compound represented by the general formula (1) include the following compounds I to VIII. These compounds can be preferably used from the viewpoint of controlling effect.

(Compound I)
In general formula (1),
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ and Y ₅ may be the same or different,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, or a C1-C6 alkyl group,
Y ₃ is a trifluoromethyl group, a C1-C6 perfluoroalkoxy group, a pentafluorosulfanyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A -C6 haloalkylsulfinyl group, or
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A -C6 haloalkylsulfonyl group is shown. )
Compound I represented by:

(Compound II)
In general formula (1),
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ is a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 haloalkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkoxycarbonyl group, a C1- C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, or halogen atom, 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 group Alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, arylsulfonyloxy A C1-C4 alkyl group substituted by one or more substituents, which may be the same or different, selected from a group, a pentafluorosulfanyl group or an alkylsilyl group,
Y ₅ is,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Y ₃ is a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group,
Trifluoromethyl group, C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfinyl group,
Or substituted with one or more substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A substituted C1-C6 haloalkylsulfonyl group is shown. Compound II represented by

(Compound III)
In general formula (1),
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, Or a C1-C6 haloalkylsulfonyl group,
Y ₅ is,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Y ₃ represents a halogen atom. )
Compound III represented by

(Compound IV)
In general formula (1),
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (4)

_(Wherein, Y 1, _{Y 5} may be the same or different,
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, nitro group,
Y ₂ and Y ₄ may be the same or different and each represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,
Ra represents a halogen atom or a hydroxy group,
Rb and Rc can each independently represent a halogen atom or a C1-C6 haloalkyl group, and at least one of Rb and Rc has at least one hydrogen atom, hydroxy group, chlorine atom, bromine atom, or iodine atom. Have )
Compound IV represented by

(Compounds V to VIII)
Compounds V to VIII, wherein at least _one of R ₁ and R ₂ is a C1-C4 alkyl group in the compounds I to IV.

  The compound represented by General formula (1) or General formula (5) can be manufactured by the method of the manufacturing methods 1-11 described below. Although the typical manufacturing method of the compound represented by General formula (1) or General formula (5) below is shown, a manufacturing method is not limited to the manufacturing method shown below.

In the general formula shown in the following production method, or Q ₂ is synonymous with Q ₂ in the [1] or general formula (2)

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

_{(Wherein, Y 6, Y 7, Y} 8, Y 9 have the same meanings as _{Y 6, Y 7, Y 8} , Y 9 in the [1].)
Indicates that

  Manufacturing method 1

(In General Formula (19) to General Formula (26), E represents —C (═G ₁ ) — or —SO ₂ —, and A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, in the above [1]. (It is synonymous with Q ₁ and Q ₂ , and L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group.)

1- (i): General formula (19) + General formula (20) → General formula (21)
By reacting the compound represented by the general formula (19) and the compound represented by the general formula (20) in a solvent or without a solvent, the compound represented by the general formula (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.

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

  On the other hand, the compound represented by the general formula (21) is produced by reacting the compound represented by the general formula (19) and the compound represented by the general formula (20) without using a halogenating agent. Is possible. For example, Chem. Ber. p. 788 (1970), that is, a method using a condensing agent using N, N′-dicyclohexylcarbodiimide by appropriately using an additive such as 1-hydroxybenzotriazole. Examples of other condensing agents used in this case include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1,1'-carbonylbis-1H-imidazole, and the like.

  In addition, as another method for producing the compound represented by the general formula (21), a mixed acid anhydride method using chloroformates can be shown. Am. Chem. Soc. 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 compound represented by the general formula (21) can be led to the compound represented by the general formula (22) by a reduction reaction. Examples of the reduction reaction include a method using a hydrogenation reaction and a method using a metal compound (for example, stannous chloride (anhydride), iron powder, zinc powder, etc.).

  In the former method, the reaction can be carried out in a suitable solvent, in the presence of a catalyst, under normal pressure or under pressure, and in a hydrogen atmosphere. Examples of the catalyst include a palladium catalyst such as palladium-carbon, a nickel catalyst such as Raney nickel, a cobalt catalyst, a ruthenium catalyst, a rhodium catalyst, a platinum catalyst, and the like. Examples of the solvent include water, alcohols such as methanol and ethanol, benzene, Aromatic hydrocarbons such as toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate can be used. The pressure is 0.1 to 10 MPa, the reaction temperature is −20 ° C. to the reflux temperature of the solvent to be used, and the reaction time is appropriately selected within the range of several minutes to 96 hours, and the compound of the general formula (22) is selected. It can be manufactured efficiently.

  The latter method is described in “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)
By reacting the compound represented by the general formula (22) and the compound represented by the general formula (23) in a solvent, the compound represented by the general formula (24) 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. Further, it can also be produced using the method using the condensing agent described in 1- (i) above or the mixed acid anhydride method.

1- (iv): General formula (24) + General formula (25) → General formula (26)
The compound represented by the general formula (26) can be produced by reacting the compound represented by the general formula (24) with the compound represented by the general formula (25) in a solvent or without a solvent. . Examples of the compound represented by the general formula (25) include alkyl halides such as methyl iodide, ethyl iodide and n-propyl bromide, and acyl halides such as acetyl chloride. In this step, a suitable base or solvent can be used, and as the base or solvent, those exemplified in the above 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of said 1- (i).

  Alternatively, instead of the compound represented by the general formula (25), an alkylating agent such as dimethyl sulfate or diethyl sulfate may be reacted with the compound represented by the general formula (24). It is possible to produce the compound represented by 26).

  Manufacturing method 2

(In General Formula (20), General Formula (23), and General Formula (27) to General Formula (30), E represents —C (═G ₁ ) — or —SO ₂ —, and A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G in the above [1]. ₂ , R ₁ , R ₂ , X, n, Q ₁ and Q ₂ , L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group, and Hal represents a halogen atom.)

2- (i): General formula (27) + General formula (23) → General formula (28)
By using the compound represented by the general formula (27) as a starting material and reacting with the compound represented by the general formula (23) according to the conditions described in the above 1- (i), the compound represented by the general formula (28) is obtained. 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) 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) above or the conditions using the mixed acid anhydride method. By making it, the compound represented by General formula (30) can be manufactured.

  Manufacturing method 3

(In General Formula (23) and General Formula (31) to General Formula (33), E represents —C (═G ₁ ) — or —SO ₂ —, and A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , R ₁ , R ₂ , X, n, in the above [1]. (It is synonymous with Q ₁ and Q ₂ , and L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group.)

3- (i): General formula (31) → General formula (32)
Synthesis 463 pages (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 in accordance with known conditions described in 829 (1984) and the like. Conditions such as the solvent and reaction temperature are not limited to those described in these documents.

3- (ii): General formula (32) + General formula (23)-> General formula (33)
A compound represented by the 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 the above 1- (i). Can be manufactured.

  Manufacturing method 4

(In General Formula (34) to General Formula (36), A ₁ , A ₂ , A ₃ , A ₄ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are A ₁ in the above [1]. _{, a 2, a 3, a} 4, R 1, R 2, X, n, the same meaning as _Q 1, Q _2.)
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 the above 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

(In General Formula (23) and General Formula (37) to General Formula (39), E represents —C (═G ₁ ) — or —SO ₂ —, and A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , R ₁ , R in the above [1]. ₂ , X, n, Q ₁ and Q ₂ , and L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group.

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, etc. can be shown besides ammonia.

5- (ii): General formula (38) + General formula (23)-> General formula (39)
A compound represented by general formula (39) by reacting a compound represented by general formula (38) with a compound represented by general formula (23) according to the conditions described in 1- (i) above. Can be manufactured.

  Manufacturing method 6

In (Formula (40) from the general formula _{(44-2), R 2, Y} 2, Y 4 has the same meaning as _{R 2, Y 2,} Y ₄ in the _{[1], Y 1, Y} 5 is Each independently represents a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, or an iodine atom, R _f represents a C1-C6 perfluoroalkyl group, and m represents 1, 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 compound (haloalkyl iodide) represented by the general formula (41) include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro iodide. -N-butyl, nonafluoro-2-butyl iodide, and the like can be used, and these may be appropriately used in the range of 1 to 10 times molar equivalents relative to the compound represented by the 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, and xylene are used. 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, the 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.

  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 or 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. As this method, 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 6- (iii) above, a compound represented by the general formula (44-2) (wherein at least _one of Y ₁ and Y ₅ always represents a methyl group) is produced. can do.

  Further, by appropriately selecting the method shown above using the compound represented by the general formula (43), the general formula (44), the general formula (43-2), or the general formula (44-2), It is possible to produce a compound represented by formula (1) or general formula (5).

By the same method, _Y 1 in the general formula _{(2), Y 2, Y} 4, Y 5 is C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl sulfinyl group, with C1-C6 perfluoroalkyl sulfonyl group A compound represented by a general formula (1) or general formula (5) can be produced.

  Manufacturing method 7

In (formula (41), the general formula (45), the general formula (46) and the general formula _(47), and R _2, Y 2, _{Y 4} is _R 2 in the _{[1], Y 2, Y} 4 Y ₁ and Y ₅ each represent a hydrogen atom, a methyl group, a chlorine atom, a bromine atom and an iodine atom, R _f represents a C1-C6 perfluoroalkyl group, and m represents 1 or 2. )
By using the compound represented by the general formula (45) as a starting material and following the production method 6, the compound represented by the general formula (47) can be produced, and the method shown above is appropriately selected. Thus, it is possible to produce a compound represented by the general formula (1) or the general formula (5).

By the same method, _Y 1 in the general formula _{(2), Y 2, Y} 4, Y 5 is C1-C6 perfluoroalkyl thio group, C1-C6 perfluoroalkyl sulfinyl group, with C1-C6 perfluoroalkyl sulfonyl group A compound represented by a general formula (1) or general formula (5) can be produced.

  Manufacturing method 8

(In General Formula (48) and General Formula (49), A ₁ , A ₂ , A ₃ , A ₄ , X, n, G ₂ , R ₂ , Q ₂ are A ₁ , A ₂ in the above [1]. , A ₃ , A ₄ , X, n, G ₂ , R ₂ , and Q ₂ .
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, propio Nitriles such as nitrile, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, 1,3-dimethyl 2-imidazolidinone, sulfolane, 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 reactive agent include alkyl halides such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide, allyl halides such as allyl iodide, odor, and the like. And propargyl halides such as propargyl halide, acyl halides such as acetyl chloride, acid anhydrides such as trifluoroacetic anhydride, and alkyl sulfates such as dimethyl sulfate and diethyl sulfate.

  These reactants may be appropriately selected or used as a solvent in the range of 1 to 5 molar equivalents relative to the compound represented by the general formula (48).

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

  Manufacturing method 9

(In General Formula (22) and General Formula (50), A ₁ , A ₂ , A ₃ , A ₄ , X, n, G ₂ , R ₁ , R ₂ , Q ₂ are A ₁ in the above [1]. , A ₂ , A ₃ , A ₄ , X, n, G ₂ , R ₁ , R ₂ , and Q ₂ .

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, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether Rusuruhokishido, alcohols such as methanol, ethanol, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more.

  Examples of the catalyst include palladium catalysts such as palladium-carbon 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 in the range of 1 to 100 atm. The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.

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

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

  Examples of the reducing agent include borohydrides such as sodium borohydride, sodium cyanoborohydride, and sodium 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)
A compound in which R ₁ is a methyl group in general formula (50) by reacting a compound represented by general formula (22) with a formylating agent in a solvent or without solvent and treating with a suitable additive Can be manufactured.

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

  Examples of the formylating agent include formic acid anhydrides such as formaldehyde, formic acid, fluoroformic acid, formyl (2,2-dimethylpropionic acid), formic acid esters such as phenyl formate, pentafluorobenzaldehyde, and oxazole. it can.

  Examples of the additive include inorganic acids such as sulfuric acid, organic acids such as formic acid, borohydrides such as sodium borohydride and sodium cyanoborohydride, boronic acid, lithium aluminum hydride, and the like.

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

  Manufacturing method 10

(In General Formula (22), General Formula (25), General Formula (51), General Formula (52), and General Formula (53), A ₁ , A ₂ , A ₃ , A ₄ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , Q ₂ are A ₁ , A ₂ , A ₃ , A ₄ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , Q _{2 in} [1]. Synonymous, Hal represents a halogen atom.)

10- (i): General formula (22) + General formula (51) → General formula (52)
Tetrahedron Letters 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 produced. 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)
A compound represented by the 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 the above 1- (iv). Can be manufactured.

  Manufacturing method 11

(Formula (20), the general formula (54), in the general formula (55) and the general formula _{(56), A 1, A} 2, A 3, A 4, G 2, R 1, R 2, X, n , Q ₁ , Q ₂ are the same as A ₁ , A ₂ , A ₃ , A ₄ , G ₂ , R ₁ , R ₂ , X, n, Q ₁ , Q _{2 in} [1], and Hal is Represents a halogen atom.)

11- (i): General formula (54) → General formula (55)
The compound represented by the general formula (55) can be produced by reacting the compound represented by the general formula (54) according to the conditions described in 2- (ii) above.

11- (ii): General formula (55) + General formula (20)-> General formula (56)
A compound represented by the 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 the above 1- (i). 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) above or the conditions using the mixed acid anhydride method. By making it, the compound represented by General formula (56) can be manufactured.

  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.

  In the following, Tables 1 to 4 show typical compounds represented by Formula (1) or Formula (5) having an insecticidal action, 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” represents a bromine atom, “I” represents an iodine atom, and “CF ₃ ” represents a trifluoromethyl group.
Formula (A)

一般式（Ｂ）

General formula (B)

一般式（Ｃ）

General formula (C)

Hereinafter, the physical property values of the compounds represented by the general formula (1) or the general formula (5) are shown in Table 5. The shift value of ¹ H-NMR shown here uses tetramethylsilane as an internal reference substance.

Physical properties of compound number 1-187
¹ H-NMR (CDCl ₃ ) δ3.54 (3H, s), 7.18-7.22 (2H, m), 7.27-7.30 (3H, m), 7.33-7.36 (1H, m), 7.42 (1H, t, J = 7.8Hz), 7.57 (1H, s), 7.67-7.70 (1H, m), 7.88 (1H, s), 8.02 (1H, d, J = 2.0Hz), 8.10 (1H, d, J = 2.0 Hz).

  Hereinafter, although the typical compound of the compound represented with General formula (CC) which has bactericidal action is shown in Table 6, this invention is not limited to these.

  In Table 6, Me represents a methyl group, i-Pr represents an isopropyl group, and t-Bu represents a tertiary butyl group.

  Table 7 below shows representative compounds represented by the general formula (DD) having a bactericidal action, but the present invention is not limited thereto.

  In Table 7, Me represents a methyl group, i-Pr represents an isopropyl group, and t-Bu represents a tertiary butyl group.

  Hereinafter, representative compounds of the compound represented by formula (AA) having an insecticidal action are shown in Table 8, but the present invention is not limited thereto.

  In Table 8, Me represents a methyl group, Cl represents a chloro group, and Br represents a bromo group.

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

  In the pest control composition of the present invention, known insecticides and acaricides that can be combined with the compound represented by the general formula (1) or the general formula (5) include, for example, azinphos-methyl. ), Acephate, isoxathion, isofenphos, ethion, etrimfos, oxydemeton-methyl, oxydeprofos, quinalphos, chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl, chlorfenvinphos, cyanophos, dioxabenzofos, dichlorvos, disulfoton, dimethylvinphos, Dimethoate, sulprofos, diazinon, thiomethone (t hiometon, tetrachlorvinphos, temephos, tebupirimfos, terbufos, nared, vamidion, pyraclofos, pyridaphenthion, pyrimiphenthionp methyl), fenitrothion, fenthion, phenthoate, fluprazofos, prothiofos, propaphos, profenofos, phoxim, phosalone, phosmet (phosalone) phosmet, formothion, phorate, malathion, mecarbam, mesulfenfos, metamidophos, methidathion, parathions, parathion-methyl, Monocrotophos, Trichlorfon, O-ethyl O-4-nitrophenyl phenylphosphonioate (EPN), isazofos, isamidofos, cadusafos, diamidafos, dilofenthion, ichlofenthion organophosphorus insecticides such as fenamiphos, fosthiazate, fosthietan, phosphocarb, O-4-dimethylsulfenylphenyl O, O-diethylphosphothiothioate (DSP), ethoprophos (ethoprophos), etc. Aldicarb, isoprocarb, ethiofencarb, carbaryl, carbosulfan, xylylcarb (xylylcarb), thiodicarb, pirimicarb, fenobucarb, furathiocarb, propoxur, bendiocarb, benfuracarb, befuracarb, metomyl, metolcarb Carbamate insecticides such as 3,5-xylylmethylcarbamate (XMC), carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate , Empenthrin, cycloprothrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin, Cypermethrin, a Facipermethrin (alpha-cypermethrin), zeta-cypermethrin (zeta-cypermethrin), silafluofen (silafluofen), tetramethrin (tetramethrin), tefluthrin, deltamethrin (deltamethrin), tralomethrin (bifenthrin), bifenthrin (bifenthrin (bifenthrin) phenothrin), fenvalerate, fenpropathrin, furamethrin, prarethrin, flucythrinate, fluvalinate, flubrocythrinate, permethrin ( synthetic pyrethroid insecticides such as permethrin), resmethrin, etofenprox, and various isomers thereof, nereistoxin insecticides such as cartap, thiocyclam, and bensultap Acetamiprid (acetamipri d), neonicotinoid insecticides such as imidacloprid, clothianidin, dinotefuran, thiacloprid, thiamethoxam, nitenpyram, chlorfluazuron, chlorfluazuron (diflubenzuron), teflubenzuron, triflumuron, novaluron, noviflumuron, bistrifluron, fluazuron, flucycloxuron, flufenoxuron , Hexaflumuron, lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyfenozide, diofenenolan, diofenolan, cyromazine, cyromazine iproxyfen), buprofezin, metoprene, hydroprene, kinoprene, triazamate and other insect growth regulators, endosulfan, chlorfenson, chlorbenzilate Organochlorine insecticides such as (chlorobenzilate), dicofol, bromopropylate, phenylpyrazole insecticides such as acetoprole, fipronil, ethiprole, pyrethrins (pyrethrins) Rotenone, nicotine sulfate, abamectin, bacillus thuringiensis (BT), insecticidal natural products such as spinosad, acequinocyl, amidoflumet, amitraz (amitraz), etoxazole, chinomethionat, kurofu Clofentezine, fenbutatin oxide, dienochlor, cyhexatin, spirodiclofen, spirodisifen, spiromesifen, tetradifon, tebufenpyrad, binapacryl , Bifenazate, pyridaben, pyrimidifen, fenazaquin, fenothiocarb, fenpyroximate, fluacrypyrim, fluazonam, fluinenam, fluzine , Propargite, benzomate, polynactins, milbemectin, lufenuron, mecarbam, methiocarb, mevinphos, halfenf Miticides such as halfenprox, azadirachtin, diafenthiuron, indoxacarb, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate (sodium oleate), chlorfenapyl, tolfenpyrad, pymetrozine, phenoxycarb, hydramethylnon, hydroxy propyl starch, pyridalyl, flufenerim ), Flubendiamide, flonicamid, metaflumizone, lepimectin, Tripyrolysocyanurate (TPIC), levamisol hydrochloride, morantel tartrate, metazome d, metazome d Examples thereof include sodium (metam-sodium), a compound represented by the general formula (AA), and a compound (BB).

  In the pest control composition of the present invention, examples of known fungicides that can be combined with the compound represented by formula (1) or formula (5) include triadimefon, hexaconazole, Propiconazole, ipconazole, prochloraz, triflumizole, tebconazole, epoxiconazole, difenoconazole, flusilazole, triazimenol triadimenol), cyproconazole, metconazole, fluquinconazole, bitertanol, tetraconazole, triticonazole, flutriafol, penconazole penconazole), diniconazole (diniconazole), Fenbuconazole, bromuconazole, imibenconazole, simeconazole, microbutanil, hymexazol, imazalil, furametpmid, furametpyr, furametpyr (etridiazole), oxpoconazole (oxpoconazole), oxpoconazole fumarate (oxpoconazole-fumarate), pefurazoate (pefurazoate), azole fungicides such as prothioconazole (prothioconazole), pyrifenox (pyrifenox), Pyrimidine fungicides such as fenarimol, nuarimol and bupirimate, ananilinopyrimidine fungicides such as mepanipyrim, cyprodinil and pyrimemethanil, metalaxyl, oxazixyl (oxadinil), benalaxyl Acylalanine fungicides such as (benalaxyl), benzimidazole fungicides such as thiophanate, thiophanate-methyl, benomyl, carbendazim, fuberidazole, thiabendazole , Dithiocarbamate fungicides such as mancozeb, propineb, propineb, zineb, metiram, maneb, ziram, thiram, organics such as chlorothalonil Chlorine fungicides, carboxamide fungicides such as ethaboxam, oxycarboxin, carboxin, flutolanil, silthiofam, mepronil, dimethomorph, phen Propidine (fenpropidin), fenpropimorph (spirpropamine), spiroxamine (spir oxamine), tridemorph (tridemorph), dodemorph, morpholine such as flumorph, azoxystrobin, kresoxim-methyl, metinominostrobin, orysastrobin , Fluoxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, picrostrobin and other strobilurin fungicides, iprodione , Procymidone, Vinclozolin, Chlozolinate, and other dicarboximide fungicides, flusulfamide, dazomet, methyl isothiocyanate, chloropicrin, metasulfocarb (methasulfocarb), hydroxy Soil fungicides such as isoxazole (hydroxyisoxazole), hydroxyisoxazole-potassium, echlomezole, 1,3-Dichloropropene (DD), metam-sodium, basic copper chloride (basic) copper chloride), basic copper sulfate, copper nonylphenol sulfonate, copper-oxinate, dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), anhydrous copper sulfate Copper fungicides such as (copper sulfate anhydride), copper sulfate, cupric hydroxide, inorganic sulfur, wettable sulfur, lime sulfur mixture (calcium polysulfide), zinc sulfate, fentin, sodium hydrogen carbonate, potassium hydrogen carbonate, hypochlorite Inorganic fungicides such as sodium hypochlorote, silver metal, edifenphos, tolclofos-methyl, fosetyl, iprobenfos, dinocap, pyrazophos ( organophosphorus fungicides such as pyrazophos, carpropamid, carpamide, fthalide, tricyclazole, pyroquilon, diclocymet, melanin biosynthesis inhibitor fungicides such as fenoxanil, Antibacterial fungicide such as kasugamycin, validamycin A, polyoxins, polyoxins, blastcidin-S, oxytetracycline, mildiomycin, streptomycin Natural product fungicides such as rape seed oil and machine oil, Carbamate fungicides such as benthiavalicarb-isopropyl, iprovalicarb, propamocarb, dietofencarb, fluorimide, fludioxonil, pyrrole such as fenpiclonil, Quinoline fungicides such as quinoxyfen and oxolinic acid, phthalimide / phthalonitrile fungicides such as chlorothalonil, captan and folpet, probenazole, acibenzoral S Plant activators that induce plant disease resistance such as methyl (acibenzolar-S-methyl) and thiadinil, cyflufenamid, fenhexamid, diflumetorim, metrafenone, picoben Pazobenzamide, proquinazid, famoxadone, cyazofamid, fenamidone, zoxamide, boscalid, cymoxanil, dithianon, nam Dichlorfluanid, triforine, isoprothiolane, ferimzone, diclomezine, tecloftalam, pencloncuron, quinomethionate, iminoate adine-imine , Iminoctadine-albesilate, ambam, polycarbamate, thiadiazin, chloroneb, nickel dimethyldithiocarbamate, guazatine, dodecylguanidine ), Kintozen ( quintozene), tolylfluanid, anilazine, nitrothal-isopropyl, fenitropan, dimethirimol, benthiazole, harpin protein, flumethover ( flumetover), mandipropamide, penthiopyrad, a compound represented by the general formula (CC), a compound represented by the general formula (DD), and the like. Some of the compounds listed above can take stereoisomers, but these isomers are also included in the present invention.

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

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

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

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

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

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

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

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

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

  Plant seeds refer to those that store nutrients for germination of young plants and are used for agricultural reproduction. For example, seeds such as corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, sweet pepper, rape, sweet potato , Seed seeds such as konjac, edible lily, bulbs such as tulips and seed balls such as raccoon. These plant seeds may be transformed. A transformed plant refers to a plant that has been created by artificially manipulating genes and the like and does not exist in nature. For example, soybean, corn, cotton, etc. imparted with herbicide resistance, rice, tobacco, etc. adapted to cold regions, corn, cotton, potato, etc., imparted with the ability to produce insecticides.

  The pest control composition of the present invention is generally used after being formulated in a convenient form for use according to a conventional formulation method for agricultural and horticultural drugs. That is, these are mixed in a suitable inert carrier, or if necessary, together with an auxiliary agent in a suitable ratio, dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and an appropriate dosage form, for example, , Suspensions, emulsions, solutions, wettable powders, granules, powders, tablets and the like.

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

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

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

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

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

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

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

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

  The following examples explain typical examples for producing the compound represented by the general formula (1) or the general formula (5) of the present invention, but are not limited thereto.

[Example 1-1]
Preparation of 5-amino-6-bromo-8-heptafluoroisopropylquinoline A solution of 1.21 g of 5-amino-8-heptafluoroisopropylquinoline in 5 ml of N, N-dimethylformamide was stirred in an ice water bath, 0.69 g of N-bromosuccinimide dissolved in 10 ml of N-dimethylformamide was added dropwise. After stirring for 1 hour in an ice-water bath and 4 hours at room temperature, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. The extract was washed twice with water, 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 → 4: 1) to obtain 1.09 g (yield 72%) of the title compound as a light brown solid.
¹ H-NMR (CDCl ₃ ) δ 4.98 (2H, broadcast-s), 7.43 (1H, dd, J = 3.9, 8.3 Hz), 8.08 (1H, d, J = 1) .0 Hz), 8.13 (1H, dd, J = 1.5, 8.3 Hz), 8.91 (1H, dd, J = 1.5, 3.9 Hz).

[Example 1-2]
Preparation of N- (6-bromo-8-heptafluoroisopropylquinolin-5-yl) 3-nitrobenzamide 0.47 g of 3-nitrobenzoyl chloride, 1.5 g of 5-amino-6-bromo-8-heptafluoroisopropylquinoline Was added to 5 ml of pyridine and stirred at room temperature. After 5 hours, ethyl acetate and 1N hydrochloric acid were added to the reaction solution, and the organic phase was separated and washed twice with water and three times with saturated aqueous sodium hydrogen carbonate. The residue obtained by distilling off the solvent under reduced pressure was dissolved in a mixed solvent of 8 ml of tetrahydrofuran and 2 ml of methanol, and stirred in an ice-water bath, 0.10 g of sodium hydroxide was added, and the mixture was stirred for 1 hour. Stir at room temperature for 4 hours. Ethyl acetate and water were added to the reaction solution, and the organic phase was separated and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to give 0.72 g (52% yield) of the title compound as a white amorphous Got as.
¹ H-NMR (CDCl ₃ ) δ 7.41 (1H, dd, J = 3.9, 8.3 Hz), 7.61 (1H, t, J = 7.8 Hz), 8.15 (1H, dd , J = 1.5, 8.3 Hz), 8.25 (1H, s), 8.28 (1H, d, J = 7.8 Hz), 8.39 (1H, d, J = 7.8 Hz) , 8.84 (1H, s), 8.87 (1H, s), 8.92 (1H, dd, J = 1.5, 3.9 Hz).

[Example 1-3]
Preparation of N- (6-bromo-8-heptafluoroisopropylquinolin-5-yl) 3-aminobenzamide N- (6-Bromo-8-heptafluoroisopropylquinolin-5-yl) 3-nitrobenzamide 0.70 g, 1 ml of concentrated hydrochloric acid was added to a solution of 0.98 g of stannous chloride (anhydrous) in 10 ml of EtOH, and the mixture was stirred at 60 ° C. for 1 hour. The reaction solution was poured into ice water, neutralized with potassium carbonate, and the precipitated insoluble material was removed by filtration using Celite. The insoluble material was washed with ethyl acetate, and the organic phase was separated from the filtrate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the precipitated solid was washed with hexane to obtain 0.56 g (yield 85%) of the title compound as a pale orange solid.
¹ H-NMR (DMSO-d6) δ 5.41 (2H, broadcast-s), 6.83 (1H, dd, J = 1.5, 9.3 Hz), 7.20-7.27 (3H, m), 7.76 (1H, dd, J = 4.4, 8.8 Hz), 8.40-8.43 (2H, m), 9.06 (1H, dd, J = 1.5, 4 .4 Hz), 10.58 (1 H, s).

[Example 1-4]
Preparation of N- (6-bromo-8-heptafluoroisopropylquinolin-5-yl) 3-[(2-fluorobenzoyl) amino] benzamide (Compound No. 1-304) N- (6-Bromo-8-heptafluoro Isopropylquinolin-5-yl) 0.15 g of 3-aminobenzamide and 0.03 g of pyridine were added to 5 ml of tetrahydrofuran and stirred at room temperature, and 0.05 g of 2-fluorobenzoyl 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 precipitated solid was washed with diisopropyl ether to give 0.17 g (yield 88%) of the title compound as a white solid. .
¹ H-NMR (DMSO-d ₆ ) δ 7.33-7.40 (2H, m), 7.57-7.63 (2H, m), 7.68-7.73 (1H, m), 7.77 (1H, dd, J = 3.9, 8.8 Hz), 7.90 (1H, d, J = 7.8 Hz), 8.03 (1H, d, J = 7.8 Hz), 8 .41-8.49 (3H, m), 9.08 (1H, dd, J = 1.5, 3.9 Hz), 10.70 (1H, s), 10.84 (1H, s).

[Example 2-1]
Preparation of N- (4-heptafluoroisopropyl-2-methylsulfonylphenyl) -N-methyl 3-nitrobenzamide N dissolved in 5 ml of tetrahydrofuran was dissolved in 0.15 g of 60% sodium hydride in 5 ml of tetrahydrofuran. -(4-Heptafluoroisopropyl-2-methylsulfonylphenyl) 1.5 g of 3-nitrobenzamide was added dropwise at room temperature. After stirring for 30 minutes at room temperature, 0.94 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was added dropwise. Subsequently, after heating up to 70 degreeC and stirring for 12 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 0.98 g (yield 64%) of the title compound as a pale yellow solid.
¹ H-NMR (CDCl ₃ ) δ 3.21 (3H, s), 3.39 (3H, s), 7.64 (1H, d, J = 8.3 Hz), 7.73 (1H, t, J = 7.8 Hz), 8.03 (1H, d, J = 8.3 Hz), 8.07 (1H, d, J = 7.8 Hz), 8.38-8.41 (2H, m), 8.55 (1H, s).

[Example 2-2]
Preparation of N- (4-heptafluoroisopropyl-2-methylsulfophenyl) -N-methyl 3-aminobenzamide N- (4-Heptafluoroisopropyl-2-methylsulfonylphenyl) -N-methyl 3-nitrobenzamide 93 g and stannous chloride (anhydrous) 1.40 g were added to 20 ml of ethanol, and then 2 ml of concentrated hydrochloric acid was added dropwise. After the charging, the temperature was raised to 60 ° C., stirred for 1.5 hours, and the reaction solution was poured into ice water. The mixture was neutralized with potassium carbonate, ethyl acetate was added, and the precipitated insoluble material was filtered off using celite. The filtrate on celite was washed well with ethyl acetate. The organic phase of the filtrate was separated, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1). The title compound (0.82 g, yield 94%) was obtained as a colorless oil.
¹ H-NMR (CDCl ₃ ) δ 3.19 (3H, s), 3.39 (3H, s), 3.88 (2H, broad-s), 6.80 (1H, d, J = 7. 8 Hz), 6.96 (1 H, s), 7.04 (1 H, d, J = 7.8 Hz), 7.26 (1 H, t, J = 7.8 Hz), 7.60 (1 H, d, J = 7.8 Hz), 7.99 (1H, d, J = 7.8 Hz), 8.40 (1H, s).

[Example 2-3]
Preparation of N- (4-heptafluoroisopropyl-2-methylsulfonylphenyl) -N-methyl 3- (2-fluorobenzoylamino) benzamide (Compound No. 1-603) The title compound according to the conditions described in Example 1-4 Manufactured. White solid.
¹ H-NMR (CDCl ₃ ) δ 3.22 (3H, s), 3.42 (3H, s), 7.17-7.23 (1H, m), 7.29-7.35 (2H, m ), 7.49-7.57 (2H, m), 7.64 (1H, d, J = 8.3 Hz), 7.81-7.83 (1H, m), 8.00-8.10. (2H, m), 8.14-8.18 (1H, m), 8.41 (1H, s), 8.62 (1H, d, J = 15.1 Hz).

[Example 3-1]
Preparation of 3- (benzoylamino) benzoic acid To a solution of 1.37 g of 3-aminobenzoic acid and 0.4 g of sodium hydroxide in 50 ml of water, 1.41 g of benzoyl chloride and 0.4 g of sodium hydroxide were added in an ice bath. Were simultaneously added dropwise in 5 ml of water and stirred at room temperature for 6 hours. 1N Hydrochloric acid was added to bring the reaction solution to pH 1, and the precipitated solid was collected by filtration to give 1.92 g (yield 80%) of the title compound as a white solid.
¹ H-NMR (CDCl ₃ ) δ 7.40-7.56 (5H, m), 7.78 (1H, d, J = 7.8 Hz), 8.00 (2H, d, J = 8.3 Hz) 8.15 (1H, d, J = 7.8 Hz), 8.35 (1H, t, J = 2.0 Hz), 9.89 (1H, s).

[Example 3-2]
Production of 3- (benzoylamino) benzoic acid chloride 2 ml of thionyl chloride was added to a solution of 1.5 g of 3- (benzoylamino) benzoic acid suspended in 10 ml of toluene, and the mixture was stirred for 2 hours under reflux conditions. After returning to room temperature, the solvent was distilled off under reduced pressure to obtain 1.53 g (yield 95%) of the title compound as a white solid.
_{^{1 H-NMR (CDCl 3)}} δ7.51-7.62 (4H, m), 7.90 (2H, d, J = 7.3Hz), 7.93 (1H, s), 7.97 (1H , S), 8.15 (1H, dt, J = 1.0, 5.9 Hz), 8.28 (1H, t, J = 2.0 Hz).

[Example 3-3]
Preparation of N-benzothiazol-6-yl 3- (benzoylamino) benzamide (Compound No. 1-492) 6-Aminobenzothiazole 0.1 g and pyridine 0.1 g were added to tetrahydrofuran 5 ml, and the resulting solution was stirred at room temperature. 0.2 g of 3- (benzoylamino) benzoic acid 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) to give the title compound 0 Obtained .15 g (52% yield) as a white solid.
MS (APCI) = 374 (M + 1)

[Example 4-1]
Production of 2,6-difluoro-3-nitrobenzoic acid 0.73 g of 2,6-difluoro-3-nitrobenzonitrile was added to 5 ml of 90% aqueous sulfuric acid, and the mixture was stirred at 120 ° C. for 2 hours. After cooling to room temperature, 5 ml of an aqueous solution in which 21.9 g of sodium nitrite was dissolved was added, followed by stirring at 80 ° C. for 1 hour. After cooling to room temperature, the mixture was discharged onto ice and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate 100%) to obtain 1.80 g (yield 96%) of the title compound as a white solid.
IR (KBr, cm ⁻¹ ); 3098, 1720, 1625, 1545, 1477, 1353.

[Example 4-2]
Production of 3-amino-2,6-difluorobenzoic acid A solution of 2,6-difluoro-3-nitrobenzoic acid and 10% palladium-carbon in 10 ml of methanol was stirred at room temperature for 2 hours in a hydrogen atmosphere. After removing the catalyst by filtration, the solvent was distilled off under reduced pressure to obtain the title compound (yield 93%) as a white solid.

[Example 4-3]
Preparation of N- (4-heptafluoroisopropyl-2-methylphenyl) 3- (benzoylamino) -2,6-difluorobenzamide (Compound No. 1-601) Using 3-amino-2,6-difluorobenzoic acid 3- (Benzoylamino) -2,6-difluorobenzoic acid was prepared according to the conditions described in Example 3-1, and then 3- (benzoylamino) -2,6- according to the conditions described in Example 3-2. Difluorobenzoic acid chloride was prepared and the title compound was prepared according to the conditions described in Example 3-3 using 4-heptafluoroisopropyl-2-methylaniline.
¹ H-NMR (DMSO-d ₆ ) δ 2.37 (3H, s), 7.29-8.01 (10H, m), 10.3 (1H, s), 10.6 (1H, s).

[Example 5-1]
Preparation of 3- (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 3-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 0.38 g (yield 14%) of the title compound. .

[Example 5-2]
Preparation of 2,4,6-tribromo-3- (heptafluoro-n-propylthio) aniline To a solution of 0.38 g of 3- (heptafluoro-n-propylthio) aniline in 10 ml of N, N-dimethylformamide, -Charged 0.72 g of bromosuccinimide. 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. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 8: 1). Purification gave 0.61 g (89% yield) of the title compound as a red oil.
¹ H-NMR (CDCl ₃ ) δ 4.87 (2H, s), 7.83 (1H, s).

[Example 5-3]
Preparation of N- {2,4,6-tribromo-3- (heptafluoro-n-propylthio)} phenyl 3-nitrobenzamide 2,4,6-tribromo-3- (heptafluoro-n-propylthio) aniline 61 g of 3-nitrobenzoyl chloride 0.43 g was added to 20 ml of pyridine and stirred at 70 ° C. for 2 hours, and then ethyl acetate and water were added to the reaction solution. The organic phase was separated and 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 = 4: 1) to give the title compound 0.69 g (89% yield) was obtained as a white solid.
¹ H-NMR (CDCl ₃ ) δ 7.76 (1H, t, J = 7.8 Hz), 7.78 (1H, s), 8.15 (1H, s), 8.32 (1H, d, J = 7.8 Hz), 8.47-8.50 (1H, m), 8.79 (1H, s).

[Example 5-4]
Preparation of N- {2,4,6-tribromo-3- (heptafluoro-n-propylthio)} phenyl 3-aminobenzamide N- {2,4,6-tribromo-3- (heptafluoro-n-propylthio) } Phenyl 3-nitrobenzamide (0.69 g) and stannous chloride anhydride (0.60 g) were added to 20 ml of ethanol, and 1 ml of concentrated hydrochloric acid was added to the solution stirred at room temperature, followed by heating and stirring at 60 ° C. for 2 hours. 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, and the filtrate was collected. The residue obtained by distilling off the solvent under reduced pressure was washed with hexane to obtain 0.62 g (yield 94%) of the title compound as a white solid. It was.
¹ H-NMR (CDCl ₃ ) δ 3.89 (2H, s), 6.89 (1H, dt, J = 6.4, 2.4 Hz), 7.27-7.31 (3H, m), 7.64 (1H, s), 8.11 (1H, s).

[Example 5-5]
Preparation of N- (2,4,6-tribromo-3-heptafluoro-n-propylthio) phenyl 3- (2-chloropyridine-3-carbonylamino) benzamide (Compound No. 1-391) N- {2,4 , 6-Tribromo-3- (heptafluoro-n-propylthio)} phenyl 3-aminobenzamide (0.15 g) and pyridine (0.04 g) were added to 5 ml of tetrahydrofuran and stirred at room temperature, and 2-chloro dissolved in 1 ml of tetrahydrofuran. 0.05 g of nicotinic acid chloride 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) to give the title compound 0 Obtained .17 g (94% yield) as an oil.
¹ H-NMR (CDCl ₃ ) δ 7.44 (1H, dd, J = 4.9, 7.8 Hz), 7.57 (1H, t, J = 7.8 Hz), 7.79 (1H, d , J = 7.8 Hz), 7.87-7.91 (2H, m), 8.13 (1H, s), 8.23 (1H, dd, J = 2.0, 7.8 Hz), 8 .31 (1H, s), 8.42 (1H, s), 8.55 (1H, dd, J = 2.0, 4.9 Hz).

[Example 6-1]
Preparation of 5-nitro-2- (2,2,2-trifluoro-1-trifluoromethylethoxy) pyridine 2.45 g (61.2 mmol) of 60% sodium hydride was charged in 15 ml of tetrahydrofuran up to 5 ° C. After cooling, 10.1 g of 1,1,1,3,3,3-hexafluoro-2-propanol was added dropwise. After stirring at 5 ° C. for 30 minutes, 5.0 g of 2-chloro-5-nitropyridine dissolved in 10 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 3 hours. After standing at room temperature for 3 days, water was added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1) to give 8.4 g of the title compound as a yellow oil. (Yield 92%).
¹ H-NMR (CDCl ₃ ) δ 6.57 (1H, septet), 7.13 (1H, d, J = 8.8 Hz), 8.54 (1H, dd, J = 8.8, 2.9 Hz) , 9.09 (1H, d, J = 2.9 Hz).

[Example 6-2]
Preparation of 5-amino-2- (2,2,2-trifluoro-1-trifluoromethylethoxy) pyridine 5-nitro-2- (2,2,2-trifluoro-1-trifluoromethylethoxy) pyridine Was used to produce the title compound according to the conditions described in Example 2-2 (yield 97%).
¹ H-NMR (CDCl ₃ ) δ3.53 (2H, brs), 6.40 (1H, septet, J = 6.4 Hz), 6.77 (1H, d, J = 8.8 Hz), 7.09 (1H, dd, J = 2.9, 8.8 Hz), 7.60 (1H, d, J = 2.9 Hz).

[Example 6-3]
Preparation of 6-bromo-5-amino-2- (2,2,2-trifluoro-1-trifluoromethylethoxy) pyridine 5-amino-2- (2,2,2-trifluoro-1-trifluoro Methylethoxy) pyridine (2.0 g) was charged in N, N-dimethylformamide (15 ml), and N-bromosuccinic acid (1.36 g) was added at room temperature. After stirring at room temperature for 2 hours, ethyl acetate was added and washed with water. After drying over anhydrous magnesium sulfate, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1) to obtain 2.35 g of the title compound as an oil (yield: 90%).
¹ H-NMR (CDCl ₃ ) δ3.92 (2H, brs), 6.23 (1H, septet, J = 7.4 Hz), 6.77 (1H, d, J = 8.3 Hz), 7.12 (1H, d, J = 8.3 Hz).

[Example 6-4]
N- [2-Bromo-4- (2,2,2-trifluoro-1-trifluoromethylethoxy) -pyridin-3-yl] Preparation of 3-nitrobenzamide 6-Bromo-5-amino-2- ( The title compound was prepared using 2,2,2-trifluoro-1-trifluoromethylethoxy) pyridine according to the conditions described in Example 1-2 (yield: 92%).
¹ H-NMR (CDCl ₃ ) δ6.31 (1H, septet, J = 5.8 Hz), 7.06 (1H, d, J = 8.8 Hz), 7.77 (1H, t, J = 8. 3 Hz), 8.25-8.29 (2H, m), 8.47-8.50 (1H, m), 8.77-8.82 (2H, m).

[Example 6-5]
N- [2-Bromo-4- (2,2,2-trifluoro-1-trifluoromethylethoxy) -pyridin-3-yl] Preparation of 3-aminobenzamide N- [2-Bromo-4- (2 , 2,2-trifluoro-1-trifluoromethylethoxy) -pyridin-3-yl] The title compound was prepared according to the conditions described in Example 1-3 using 3-nitrobenzamide (yield: 81% ).
¹ H-NMR (CDCl ₃ ) δ 3.90 (2H, brs), 6.29 (1H, septet, J = 5.9 Hz), 6.88-6.91 (1H, m), 7.00 (1H , D, J = 8.8 Hz), 7.21-7.32 (3H, m), 8.23 (1H, brs), 8.85 (1H, d, J = 8.8 Hz).

[Example 6-6]
N- [2-Bromo-6- (2,2,2-trifluoro-1-trifluoromethylethoxy) -pyridin-3-yl] Preparation of 3- (benzoylamino) benzamide (Compound No. 1-387) N -[2-Bromo-6- (2,2,2-trifluoro-1-trifluoromethylethoxy) -pyridin-3-yl] Described in Example 1-4 using 3-aminobenzamide and benzoyl chloride. The title compound was prepared according to the conditions (yield: 76%).
¹ H-NMR (CDCl ₃ ) δ 6.30 (1H, septet, J = 6.8 Hz), 7.01 (1H, d, J = 8.8 Hz), 7.49-7.61 (4H, m) , 7.68 (1H, dd, J = 1.0, 7.8 Hz), 7.88-7.91 (2H, m), 7.96-8.01 (2H, m), 8.26 ( 1H, t, J = 1.9 Hz), 8.33 (1H, s), 8.81 (1H, d, J = 8.8 Hz).

[Example 7-1]
Preparation of N- (2-bromo-6-methyl-4-pivaloyloxyphenyl) 3-nitrobenzamide 2-methyl-4- (pivaloyloxy) aniline synthesized according to the method described in Tetrahedron 12263-12276 (1995) Was used to prepare 2-bromo-6-methyl-4- (pivaloyloxy) aniline according to the conditions described in Example 1-1 and the title compound was prepared according to the conditions described in 1-2 (yield: 52% ).
¹ H-NMR (CDCl ₃ ) δ 1.36 (9H, s), 2.36 (3H, s), 7.00 (1H, d, J = 2.0 Hz), 7.27 (1H, d, J = 2.0 Hz), 7.65 (1 H, br.), 7.74 (1 H, t, J = 8.3 Hz), 8.31 (1 H, dd, J = 1.5, 6.3 Hz) , 8.44-8.47 (1 H, m), 8.79 (1 H, t, J = 2.0 Hz).

[Example 7-2]
Preparation of N- (2-bromo-6-methyl-4-hydroxyphenyl) 3-aminobenzamide N- (2-bromo-6-methyl-4-pivaloyloxyphenyl) 3-nitrobenzamide and aqueous sodium hydroxide solution in methanol And stirred at 70 ° C. for 3 hours. The residue obtained by evaporating the solvent under reduced pressure was dissolved in ethyl acetate, washed with 2N aqueous hydrochloric acid solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. After the obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1), N- (2-bromo-6-methyl-4-hydroxyphenyl) 3-nitrobenzamide was obtained. The title compound was prepared according to the conditions described in Example 1-3 (97% yield).

[Example 7-3]
Production of N- (2-bromo-4-hydroxy-6-methyl-phenyl) 3- (benzoylamino) benzamide (Compound No. 1-484)
The title compound was prepared according to the conditions described in Example 1-4 using N- (2-bromo-6-methyl-4-hydroxyphenyl) 3-aminobenzamide (95% yield).
¹ H-NMR (DMSO-d ₆ ) δ 2.16 (3H, s), 6.72 (1H, d, J = 2.4 Hz), 6.94 (1H, d, J = 2.4 Hz), 7.50-7.63 (4H, m), 7.74 (1H, d, J = 8.3 Hz), 7.98-8.05 (3H, m), 8.32 (1H, s), 9.79 (1H, s), 9.81 (1H, s), 10.4 (1H, s).

[Example 7-4]
Production of N- (2-bromo-6-methyl-4-trifluoromethanesulfonyloxyphenyl) 3- (benzoylamino) benzamide (Compound No. 1-369)
N- (2-bromo-6-methyl-4-hydroxyphenyl) 3- (benzoylamino) benzamide (0.2 g) and trifluoromethanesulfonyl anhydride (0.14 g) were added to pyridine, and the mixture was stirred at 80 ° C. for 7 hours. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 0.08 g (yield 31%) of the title compound. .
¹ H-NMR (DMSO-d ₆ ) δ 2.32 (3H, s), 7.52-7.63 (5H, m), 7.76 (1H, d, J = 7.8 Hz), 7. 87 (1H, d, J = 2.7 Hz), 8.00 (2H, dd, J = 1.5, 7.8 Hz), 8.06 (1H, d, J = 7.8 Hz), 8.37 (1H, s), 10.18 (1H, s), 10.47 (1H, s).

[Example 7-5]
Preparation of N- [2-bromo-6-methyl-4- (p-toluenesulfonyloxy) phenyl] 3- (benzoylamino) benzamide (Compound No. 1-485)
N- (2-bromo-6-methyl-4-hydroxyphenyl) 3- (benzoylamino) benzamide 0.30 g, 1,1,1,3,3,3-hexafluoroisopropyl p-toluenesulfonate 0.23 g, 0.19 g of potassium carbonate and 0.03 g of 18-crown-6 ether were added to 5 ml of N, N-dimethylformamide and stirred at 70 ° C. for 6 hours. 100 ml of ethyl acetate was added and washed with water (50 ml × 2). The organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1). 05 g (yield 13%) was obtained.
1H NMR (CDCl ₃ ) δ 2.29 (3H, s), 2.48 (3H, s), 6.94 (1H, d, J = 2.9 Hz), 7.14 (1H, d, J = 2.9 Hz), 7.36 (2H, d, J = 8.3 Hz), 7.51-7.61 (5H, m), 7.71-7.77 (3H, m), 7.88- 7.92 (3H, m), 7.99 (1H, br.s), 8.28 (1H, s).

[Example 8-1]
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. The solution was filtered and the filtrate was collected. The solvent was distilled off under reduced pressure, and the resulting residue was washed with a mixed solvent of hexane-diisopropyl ether to give 26.0 g of the title compound (yield 85%). Was obtained as a white solid.
¹ H-NMR (CDCl ₃ ) δ 2.33 (6H, s), 7.37 (2H, s), 7.68 (1H, s), 7.72 (1H, t, J = 8.1 Hz) , 8.28 (1H, d, J = 8.1 Hz), 8.44 (1H, dd, J = 1.2, 8.1 Hz), 8.75 (1H, t, J = 1.2 Hz)

[Example 8-2]
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, and the filtrate was collected. The residue obtained by distilling off the solvent under reduced pressure was washed with hexane to obtain 0.44 g (yield 53%) of the title compound as a white solid. It was.
¹ H-NMR (CDCl ₃ ) δ 2.34 (6H, s), 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6H, m)

[Example 8-3]
N- [2,6-Dimethyl-4- (heptafluoroisopropyl) phenyl] Preparation of 3- (4-nitrophenylamino) benzamide (Compound No. 5-9) N- (2,6-Dimethyl-4-heptafluoro Isopropyl) phenyl 3-aminobenzamide 0.3 g, 4-bromonitrobenzene 0.18 g, 9,9-dimethyl-4,5-bis (diphenylphosphino) xanthene 21 mg, cesium carbonate 0.29 g were charged in a reaction vessel. The mixture was stirred at room temperature for 15 minutes under a nitrogen stream. After charging 6 mg of palladium acetate, the mixture was reacted at 90 ° C. for 6 hours under a nitrogen atmosphere. After cooling to room temperature, ethyl acetate was charged and washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1 → 8: 2 → 2: 1). 0.16 g (yield 74%) of the compound was obtained as yellow crystals.
¹ H-NMR (CDCl ₃ ) δ 2.36 (6H, s), 6.50 (1H, brs), 7.02 (2H, d, J = 8.7 Hz), 7.38 (2H, s), 7.42 (1H, s), 7.46 (1H, d, J = 7.8 Hz), 7.53 (1H, t, J = 7.8 Hz), 7.60 (1H, d, J = 7 .8 Hz), 7.91 (1H, brs), 8.19 (2H, d, J = 8.7 Hz).

[Example 9-1]
N- [3-[(2,6-Dimethyl-4-heptafluoroisopropylphenyl) aminocarbonyl] phenyl] Production of 4-chlorobenzenesulfonamide (Compound No. 4-6) N produced in Example 8-2. -(2,6-Dimethyl-4-heptafluoroisopropyl) phenyl 3-aminobenzamide (0.30 g) was added to pyridine (5 ml), and 4-chlorobenzenesulfonyl chloride (0.16 g) was charged and stirred at room temperature for 2 hours. . Then, ethyl acetate was added and then poured into ice water. The aqueous phase was acidified using concentrated hydrochloric acid, the organic phase was separated, washed twice with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to give 0.30 g (yield 70%) of the title compound as a white amorphous product. Got as.
_{^{1 H-NMR (CDCl 3)}} δ 2.29 (6H, s), 7.32-7.39 (6H, m), 7.58-7.66 (6H, m).

[Example 10-1]
Preparation of 4- (1,1,2,3,3,3-hexafluoropropoxy) -nitrobenzene To a solution of 4.63 g of p-nitrophenol and 0.56 g of potassium hydroxide in 100 ml of N, N-dimethylformamide Then, after hexafluoropropene was blown at room temperature, the mixture was stirred at 50 ° C. for 1 hour. Next, ethyl acetate and water were added, and the organic phase was separated. The organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 20: 1) to give 3.81 g of the title compound (yield 42 %) As a yellow oil.
¹ H-NMR (CDCl ₃ ) δ 5.06 (1H, ddt, J = 44.0, 11.2, 5.2 Hz), 7.39 (2H, d, J = 8.8 Hz), 8.30 (2H, d, J = 8.8 Hz).

[Example 10-2]
Preparation of 4- (1,1,2,3,3,3-hexafluoropropoxy) -aniline Example 1 using 4- (1,1,2,3,3,3-hexafluoropropoxy) -nitrobenzene The title compound was obtained as an oil according to the conditions described in -3.
¹ H-NMR (CDCl ₃ ) δ 3.69 (2H, brs), 4.96 (1H, dddd, J = 44.0, 11.2, 11.2, 5.6 Hz), 6.64 (2H , D, J = 8.8 Hz), 6.98 (2H, d, J = 8.8 Hz).

[Example 10-3]
Preparation of 2,6-dibromo-4- (1,1,2,3,3,3-hexafluoropropoxy) -aniline 2 equivalents of N-bromosuccinimide were used under the conditions described in Example 1-1. The title compound was thus obtained as an oil.
¹ H-NMR (CDCl ₃ ) δ 4.51 (2H, brs), 4.96 (1H, dddd, J = 44.0, 11.2, 11.2, 6.0 Hz), 7.30 (2H , S).

[Example 10-4]
Preparation of N- (2,6-dibromo-4- (1,1,2,3,3,3-hexafluoropropoxy) phenyl) 3-nitrobenzamide The title compound was prepared according to the conditions described in Example 1-2. Obtained as a solid.
¹ H-NMR (CDCl ₃ ) δ 5.01 (1H, brd, J = 44.0 Hz), 7.52 (1H, s), 7.57-7.78 (2H, m), 8.13 ( 1H, d, J = 7.6 Hz), 8.32-8.38 (2H, m), 8.65 (1H, s).

[Example 10-5]
Preparation of N- (2,6-dibromo-4- (1,1,2,3,3,3-hexafluoropropoxy) phenyl) 3-aminobenzamide The title compound was prepared according to the conditions described in Example 1-3. Obtained as a solid.
¹ H-NMR (DMSO-d ₆ ) δ 5.18 (2H, brs), 6.26 (1H, brd, J = 44.0 Hz), 6.80 (1H, d, J = 6.4 Hz), 7.14 (2H, t, J = 7.6 Hz), 7.20 (1H, s), 7.63 (2H, s), 10.14 (1H, s).

[Example 10-6]
N- (2,6-dibromo-4- (1,1,2,3,3,3-hexafluoropropoxy) phenyl) 3-[(2-fluorobenzoyl) amino] benzamide (Compound No. 2-8) Production The title compound was obtained as amorphous according to the conditions described in Example 1-4.
¹ H-NMR (CDCl ₃ ) δ 5.01 (1H, brd, J = 44.0 Hz), 7.23 (2H, d, J = 8.0 Hz), 7.42 (4H, t, J = 7 .2 Hz), 7.52-7.55 (6H, m), 7.65 (2H, d, J = 7.6 Hz), 7.82 (4H, d, J = 8.0 Hz), 8.02 (2H, s), 8.25 (2H, s).
Next, typical preparation examples of the present invention are shown, but the present invention is not limited thereto. In the preparation examples, “parts” means “parts by weight”.

[Formulation Example 1]
2 parts of Compound 1-187, 10 parts of probenazole, 0.5 part of wetting agent (trade name Airol CT-1 manufactured by Toho Chemical Industry Co., Ltd.), 3 parts of binder (manufactured by Nippon Synthetic Chemical Co., Ltd., Gohsenol) , 15 parts talc (trade name Victorylite manufactured by Katsumiyama Mining Co., Ltd.) and 71.5 parts clay (trade name SP manufactured by Katsuyama Co., Ltd., trade name SP) are mixed, and after addition, extrusion granulator Molded with. The obtained molded product was dried and then sized to obtain granules.

[Formulation Example 2]
2 parts of compound 1-187, 5 parts of orisatrobin, 0.5 parts of wetting agent (trade name Airol CT-1 manufactured by Toho Chemical Industry Co., Ltd.), binder (made by Daiichi Kogyo Seiyaku Co., Ltd., trade name cellogen ) 3 parts, 15 parts of talc (trade name Victorylite, manufactured by Katsumiyama Mining Co., Ltd.) and 74.5 parts of clay (trade name SP, manufactured by Katsuyama Industrial Co., Ltd.), mixed and extruded, and then extruded. Molded with a granulator. The obtained molded product was dried and then sized to obtain granules.

[Formulation Example 3]
0.5 part of compound 2-167, 0.2 part of kasugamycin monohydrochloride, 0.3 part of flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles C), clay (manufactured by Asahi Minesue Co., Ltd., trade name) 50 parts of O-4410) and 49 parts of calcium carbonate (product name NN # 200, manufactured by Nitto Flour Industry Co., Ltd.) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 4]
0.5 part of Compound 1-187, 1.0 part of tricyclazole, 0.3 part of a flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles A), clay (manufactured by Asahi Mineral Co., Ltd., trade name O-4410 ) 50 parts, 48.2 parts of calcium carbonate (manufactured by Nitto Flour Chemical Co., Ltd., trade name NN # 200) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 5]
0.5 parts of compound 1-306, 2.0 parts of flutolanil, 0.3 part of a flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles A), clay (manufactured by Asahi Minesue Co., Ltd., trade name O-4410) ) 50 parts, 47.2 parts of calcium carbonate (manufactured by Nitto Flour Chemical Co., Ltd., trade name NN # 200) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 6]
0.5 part of Compound 2-167, 0.3 part of fursulfamide, 0.3 part of a flocculant (manufactured by Sankyo Co., Ltd., trade name Doriles A), clay (manufactured by Asahi Minesue Co., Ltd., trade name O-4410) ) 50 parts, 48.9 parts calcium carbonate (manufactured by Nitto Flour Chemical Co., Ltd., trade name Doreres A) were mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 7]
Compound 1-187 0.5 parts, Fenitrothion 3.0 parts, flocculant (manufactured by Sankyo Co., Ltd., Doreres A) 0.3 parts, amorphous hydrous silicate (Degussa Japan Co., Ltd., trade name Carplex) # 80D) 2.0 parts, clay (made by Asahi-Kou Sue Co., Ltd., trade name O-4410) 50 parts, calcium carbonate (made by Nitto Flour Chemical Co., Ltd., trade name NN # 200) 44.2 parts The mixture was mixed and pulverized with a pin mill to obtain a powder.

[Formulation Example 8]
5 parts of compound 1-306, 10 parts of imidacloprid, 1.5 parts of wetting / dispersing agent (trade name Solpol 3074, manufactured by Toho Chemical Industry Co., Ltd.), dispersing agent (trade name, Demol N, manufactured by Kao Corporation) 2 .5 parts, 0.08 part of thickener (Rhodia Nikka Co., Ltd., trade name Road Pole) and 80.92 parts of water were mixed, pulverized with a wet pulverizer and filtered to obtain a flowable agent. Obtained.

[Formulation Example 9]
10 parts of compound 2-167, 15 parts of pyridaben, 2.5 parts of wetting / dispersing agent (trade name Solpol 3074, manufactured by Toho Chemical Industry Co., Ltd.), dispersing agent (trade name, Demol N, manufactured by Kao Corporation) 3 0.0 part, a thickener (Rhodia Nikka Co., Ltd., trade name Road Pole) 0.08 part and water 69.42 parts were mixed, then pulverized with a wet pulverizer and filtered to obtain a flowable agent. Obtained.

[Formulation Example 10]
10 parts of Compound 1-187, 5 parts of chlorfenapyr, 1.5 parts of wetting / dispersing agent (trade name Solpol 3074, manufactured by Toho Chemical Industry Co., Ltd.), dispersing agent (trade name, Demol N, manufactured by Kao Corporation) 2 .5 parts, 0.08 part of thickener (Rhodia Nikka Co., Ltd., trade name Road Pole) and 80.92 parts of water were mixed, pulverized with a wet pulverizer and filtered to obtain a flowable agent. Obtained.

[Formulation Example 11]
10 parts of compound 1-306, 20 parts of buprofezin, 1.5 parts of wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.5 parts of dispersant (trade name Emar, manufactured by Kao Corporation) Then, 2.0 parts of a dispersant (trade name Demol N, manufactured by Kao Corporation) and 64 parts of diatomaceous earth were mixed and then pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 12]
10 parts of compound 2-167, 20 parts of pymetrozine, 1.5 parts of a wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.5 parts of a dispersant (trade name Emar, manufactured by Kao Corporation) Then, 2.0 parts of a dispersant (trade name Demol N, manufactured by Kao Corporation) and 64 parts of diatomaceous earth were mixed and then pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 13]
10 parts of compound 1-187, 5 parts of fipronil, 2.0 parts of a wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.0 parts of a dispersant (trade name Emar, manufactured by Kao Corporation) Then, 2.0 parts of a dispersant (trade name Demol N, manufactured by Kao Corporation) and 79 parts of diatomaceous earth were mixed and then pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 14]
30 parts of isoxathion, 2.0 parts of a dispersant (trade name Solpol 7290P, manufactured by Toho Chemical Industry Co., Ltd.) and 25 parts of amorphous hydrous silicic acid (trade name Carplex # 80D, manufactured by Degussa Japan Co., Ltd.) were mixed. Thereafter, 10 parts of Compound 1-306, 1.5 parts of a wetting agent (trade name Solpol 5050, manufactured by Toho Chemical Industry Co., Ltd.), 2.0 parts of a dispersant (trade name Emar, manufactured by Kao Corporation), dispersed After mixing 2.0 parts of an agent (trade name Demol N, manufactured by Kao Corporation) and 27.5 parts of diatomaceous earth, the mixture was pulverized with a jet mill to obtain a wettable powder.

[Formulation Example 15]
5 parts of compound 2-167, 5 parts of dinotefuran, 2.0 parts of a wetting agent (manufactured by Toho Chemical Industry Co., Ltd., Solpol 5050), 2.0 parts of a dispersant (trade name Emar, manufactured by Kao Corporation), and After mixing 86 parts of diatomaceous earth, the mixture was pulverized with a jet mill to obtain a wettable powder.

  Furthermore, in order to clarify that the pest control composition of the present invention has an excellent pest control effect, test examples are shown below, but the present invention is not limited thereto.

[Test Example 1]
Insecticidal test for peach aphids 8 cm in diameter and 8 cm in height, planted eggplant (variety: Senryo 2), and bred the peach aphid, then sprayed the medicinal solution diluted to a predetermined concentration on the foliage. . After air drying, the pot was left in the greenhouse, and after 5 days of spraying, the number of aphids parasitic on each eggplant was investigated, and the control rate was calculated according to the following criteria (1 ward 1 pot 2 continuous system).
Control rate = 100 − {(Ta × Cb) / (Tb × Ca)} × 100
Table 9 shows the results of the number of parasites after spraying in the treated group Tb: the number of parasites before spraying in the treated group Ca: the number of parasites after spraying in the untreated group Cb: the number of parasites before spraying in the untreated group.

[Test Example 2]
Insecticidal test for resistant cotton aphids After planting cucumbers (variety: Sagamihanjiro) in a plastic pot with a diameter of 8 cm and a height of 8 cm, and breeding resistant cotton aphids, a medicinal solution diluted to a prescribed concentration is applied to the foliage. Sufficiently sprayed. After air drying, the pot was left in the greenhouse, and after 5 days of spraying, the number of aphids parasitic on each cucumber was investigated, and the control rate was calculated according to the following criteria (1 ward 1 pot 2 continuous system).
Control rate = 100 − {(Ta × Cb) / (Tb × Ca)} × 100
Table 10 shows the results of the number of parasites after spraying in the treated group Tb: the number of parasites before spraying in the treated group Ca: the number of parasites after spraying in the untreated group Cb: the number of parasites before spraying in the untreated group.

[Test Example 3]
Insecticidal test for Japanese brown planthopper A chemical solution diluted to a prescribed concentration is sprayed on rice seedlings (variety: Koshihikari), air-dried, and placed in a glass test tube with a diameter of 3 cm and a height of 10 cm together with 10 Japanese rice planters. Cotton plug was put on. The number of survivors 6 days after the treatment was investigated, and the death rate was calculated (2 units per 10 wards in 1 ward). The results are shown in Table 11.

[Test Example 4]
Insecticidal test against a spider mite A plastic cup with a diameter of 8 cm is filled with water, a lid with a hole with a diameter of 1 cm is placed, absorbent cotton is placed on the top of the lid, and the absorbent cotton is constantly dampened by capillarity by suspending it in the water. I made it. A leaf disk having a diameter of 2 cm was prepared from green kidney leaves and placed on the absorbent cotton, and 4 adult females of the spider mite were inoculated there. On the next day, the female adults were removed, the number of eggs laid was examined, and a chemical solution prepared to a predetermined concentration was sprayed using a vertical sprayer. After spraying, it was placed in a constant temperature room at 25 ° C., and the number of hatched larvae surviving on the leaf disk was investigated 6 days after spraying, and the hatched larvae rate was calculated (1 drug, 1 concentration, 2 consecutive). The results are shown in Table 12.

[Test Example 5]
The rice plant (variety: Nihonbare) cultivated in the rice seedling box by the application of paddy rice seedling box was treated with 50 g of the granule per box and transplanted to Honda. As for the control effect on Japanese brown planthopper, the number of parasites was investigated for 30 strains in each group 40 days and 60 days after transplantation, and as for the control effect on corn borer, the number of damaged leaves was investigated for 100 strains in each group 50 days after transplantation, and the rate of damaged leaves was calculated. The results are shown in Table 13.

[Test Example 6]
Insecticidal test against mung beetle larvae Cut cabbage leaves for 30 seconds in a chemical solution diluted to a prescribed concentration, air-dried, put into a plastic container with a diameter of 9 cm, inoculate 10 mites of 2 maturity larvae, and kept static in a constant temperature room at 25 ° C. I put it. Six days after the treatment, the number of surviving insects was examined, and the death rate was calculated (2 units per 10 wards in 1 ward). The results are shown in Table 14.

[Test Example 7]
Nika-meiga insecticidal test and rice blast control test using rice seedling box application After treatment of rice (variety: Koshihikari) grown in a seedling box with a prescribed amount of granules, 4 plants are transplanted in 1 / 5000a pots for 4 pots. did. 14 days after the treatment of 2 pots, the stems and leaves were cut out and placed in a plastic cup (diameter 10 cm, height 10 cm) together with 10 second instar larvae, and the mortality was investigated 4 days later (two-running system). The other 2 pots were placed in an artificial weather chamber (setting conditions: 25 ° C., 12 hours light / dark cycle) 30 days after the treatment, and spray-inoculated with a rice blast spore suspension. The weather chamber was kept at high humidity, and after 7 days, the number of blast spots was investigated, and the control value was calculated by the following formula (two continuous systems). The results are shown in Table 15.
Control value = (1−number of lesions in treated area / number of lesions in untreated area) × 100

[Test Example 8]
Paddy rice Ichimongiseseri and blast control test Rice powder (variety: Koshihikari) 70 days after transplanting (mid-May) was sprayed with a powder at a predetermined concentration. Prior to spraying, the leaves that had been parasitic on Ichimongiseseri were removed, and the number of insects was examined for 100 strains in each group 20 days after spraying. In addition, an affected seedling of blast disease was placed in the center of each ward 10 days before spraying, and after 30 days of spraying, the number of ear blasting ears was investigated for 20 strains in each ward, and the control value was calculated by the following formula. The results are shown in Table 16.
Degree of damage a: Onset of head neck b: Onset of branch infarction 1/3 or more c: Onset of inferior branch infarction 1/3 Injury = attack rate of a + onset rate of b × 0.66 + onset rate of c × 0.26
Control value = (1-Damage level of treated area / Damage level of untreated area) x 100

[Test Example 9]
Paddy rice Ichimon dissemination and blight control test Rice (variety: Koshihikari) 70 days after transplanting (mid-May) was sprayed with a predetermined amount of powder. Prior to spraying, the leaves that had been parasitic on Ichimongiseseri were removed, and the number of insects was examined for 100 strains in each group 20 days after spraying. Further, rice plant blight fungus cultivated in a bran medium 7 days before spraying was inoculated to the plant origin, and 30 days after spraying, the pathogenic strain was investigated for 100 strains in each ward, and the pathogenic strain rate was calculated. The results are shown in Table 17.

[Test Example 10]
A pear pear and scab control test A 17-year-old pear (variety: Hosui) was sprayed with a sufficient amount of a drug prepared at a predetermined concentration (early June). Forty days after spraying, the number of fruits damaged by Nashihimeshinki was investigated for all fruits in the ward, and the rate of damage was calculated. Further, on the 14th day after spraying, the occurrence of scab was investigated for any 200 leaves in the ward according to the degree, and the severity was calculated by the following formula. The results are shown in Table 18.
Disease severity = Σ (number of diseased leaves by degree × index) × 100 / (number of leaves surveyed × 5)
Index: (0: No disease, 1: 1 to 3 lesions, 3: 4 to 7 lesions, 5: 8 or more lesions)

[Test Example 11]
Cucumber urine borer insecticidal test and powdery mildew control test A sufficient amount of the drug prepared at a predetermined concentration was sprayed on cucumber (variety: Sagamihanjiro) cultivated in a greenhouse. Seven days after spraying, one leaf was cut out and put into a plastic cup (diameter 10 cm, height 10 cm) together with 5 2nd instar larvae, and the mortality was investigated 4 days later. In addition, powdery mildew on the diseased leaves of cucumber that had been diseased one day after spraying was uniformly inoculated with a paint brush and inoculated 10 days later. The area occupied by lesions per cucumber leaf was examined according to the following index, and the control value was calculated from the average disease severity in each section using the following formula (two-line system). The results are shown in Table 19.
Disease severity 0: No lesion
1: lesion area is 5% or less
2: The lesion area is 6-25%
3: The lesion area is 26-50%
4: The lesion area is 51% or more Control value = (1−average disease severity in treated area / average disease severity in untreated area) × 100

[Test Example 12]
Test of controlling cabbage and root-knot disease by soil treatment of cabbage Planted cabbage (variety: four seasons) cultivated with cell seedlings with a prescribed amount of powder mixed with soil. Seven days after the treatment, the number of strains damaged by Cabrayaga was investigated and the rate of damaged strains was calculated. In addition, 60 days after the treatment, the strain was extracted, and the occurrence of root-knot disease was investigated according to the degree. The results are shown in Table 20.
Disease severity 0: Does not recognize root-knot formation
1: The root hump grows on less than 1-25% of the root system
2: The root humps grow on less than 25-50% of the root system
3: Root bumps grow on less than 50-75% of the root system
4: Root humps grow on roots of 75% or more of the whole root system Control value = (1−average disease severity in treated area / average disease severity in untreated area) × 100

[Test Example 13]
Rice blast control effect
A predetermined amount of wettable powder and a commercially available seed fungicide (Trihumine wettable powder) were each soaked for 48 hours in naturally infected rice fir (variety: Koshihikari). After soaking (15 ° C., 3 days) and germination (30 ° C., 24 hours), seeds treated with chemicals and seeds not treated with chemicals were sown 100 times per pot in plastic pots. And grown in a greenhouse. After 20 days of cultivation, all seedlings were examined for the presence of disease with the naked eye, and the diseased seedling rate was calculated. The presence or absence of phytotoxicity was also examined with the naked eye. The results are shown in Table 21.
Disease seedling rate = (number of diseased seedlings / total number of surveyed seedlings) × 100

[Test Example 14]
Control effect on sugar beet flea beetle A predetermined amount of wettable powder was treated with a seed dressing machine (chemical injection in a rotating drum).
After 45 days of treatment, the degree of damage caused by the flea beetle was indexed and the control rate was calculated.
The presence or absence of phytotoxicity was also examined with the naked eye.
The results are shown in Table 22.
The degree of damage and the index are as follows: Index 0: No damage, Index 1: Less damage
Index 2: Medium degree of food damage, Index 3: High degree of food damage Control rate = 100 − ((1 × index 1 number of food damage + 2 × number of food damages of index 2 + 3 × index 3 number of food damages) / 3 × total number of surveys × 100)

[Test Example 15]
Control effect against Azuki beetle
A flowable agent of a predetermined dose was applied to 1 kg of azuki bean seeds by 5, 10, 20 ml. After air drying, a part was transferred to a 9 cm waist high petri dish and left in a constant temperature room at 25 ° C. After treatment 2 and 3 months, 10 male and female adult weevil were released per waist-high petri dish (5-regulation). Two days after the release, the number of dead insects and the number of eggs laid on azuki bean were examined, and the death rate was calculated. The presence or absence of phytotoxicity was also examined with the naked eye.
The results are shown in Table 23.
Death rate = (Number of dead insects in the treatment area / 50) x 100

Claims (21)

General formula (1)

{Wherein A ₁ , A ₂ , A ₃ , A ₄ each represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
R ₁ and R ₂ each independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, amino group, cyano group, nitro group, hydroxy group, C1-C4 alkyl Carbonyl group, C1-C4 haloalkylcal Nyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, One or more substituents selected from a C1-C4 alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group or a phenyl group, which may be the same or different. A substituted phenyl group having,
A carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, an anthracenyl group, or a norbornyl group);
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, amino group, cyano group, nitro group, hydroxy group, C1-C4 alkyl Carbonyl group, C1-C4 haloalkylcal Nyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, One or more substituents selected from a C1-C4 alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group or a phenyl group, which may be the same or different. A substituted carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, an anthracenyl group or a norbornyl group) ),
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, an acridinyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, amino group, cyano group, nitro group, hydroxy group, C1-C4 alkyl Carbonyl group, C1-C4 haloalkylcal Nyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, One or more substituents selected from a C1-C4 alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group or a phenyl group, which may be the same or different. Substituted heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group) Group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl Group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, acridinyl group or dihydropyranyl group. And
Q ₂ represents a carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group. Show)
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted carbocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The carbocyclic group here represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group.
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, benzimidazolyl group or dihydropyranyl group).
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is a pyrazinyl group, a pyridin-2-yl group, a pyridin-4-yl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, Oxadiazo Group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, Indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, benzoimidazolyl group or dihydropyranyl group are shown. ),
A C1-C6 alkyl group,
Halogen atom, 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 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 Haloa Killcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy A substituted C1-C6 alkyl group having one or more substituents which may be the same or different and selected from a group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group,
Group represented by general formula (2)

(Wherein Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Halogen atom, 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 haloalkylcarbonyl group, C1-C4 alkylcarbonyl Oxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 group Substituted C1-substituted by one or more substituents which may be the same or different and selected from a killsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group or an alkylsilyl group A C6 alkyl group,
C1-C6 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-C6 An alkoxy group, a C1-C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
A C1-C6 haloalkyl group optionally substituted by one or more hydroxyl groups,
A C1-C6 haloalkyl group optionally substituted with one or more C1-C6 haloalkyl groups,
A C1-C6 haloalkyl group optionally substituted with one or more alkoxy groups,
A C1-C6 haloalkyl group optionally substituted by one or more haloalkoxy groups,
A C1-C6 alkylthio group,
A C1-C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
A C1-C6 alkylsulfinyl group,
A C1-C6 haloalkylsulfinyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfinyl group,
A C1-C6 alkylsulfonyl group,
A C1-C6 haloalkylsulfonyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfonyl group,
C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group,
C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, cyano group, nitro group Group, hydroxy group, pentafluorosulfanyl group, carboxyl group, carbamoyl group, C1-C3 alkylaminocarbonyl group, phenylazo group, pyridyloxy group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted pyridyloxy group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group. However,
Y ₁ and Y ₅ may be the same or different,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1 In the case of -C3 haloalkylsulfonyl group or cyano group,
Except for the case where Y ₃ is a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group. ),
Or a group represented by the general formula (3)

(Wherein Y ₆ , Y ₇ , Y ₈ and Y ₉ may be the same or different,
Hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group A C3-C8 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, an optionally substituted C1-C6 haloalkyl group, or an optionally substituted alkoxy group. Good C1-C6 haloalkyl group, C1-C6 haloalkyl group optionally substituted with one or more haloalkoxy groups, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkyl Sulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloa Killsulfonyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, Cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group.
However, Y ₆ and Y ₉ may be the same or different, and are a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group. , A C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, or a cyano group, Y ₈ represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1- The case where it is a C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, or a C1-C6 perfluoroalkylsulfonyl group is excluded. )
Indicates. } As an active ingredient, one or two or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides or known fungicides are contained. A pest control composition characterized by the above. In the general formula (1), the compound represented by the general formula (1)
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ and Y ₅ may be the same or different,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, or a C1-C6 alkyl group,
Y ₃ is a trifluoromethyl group, a C1-C6 perfluoroalkoxy group, a pentafluorosulfanyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A -C6 haloalkylsulfinyl group, or
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A -C6 haloalkylsulfonyl group is shown. )
The pest control composition according to claim 1, which is a compound represented by: In the general formula (1), the compound represented by the general formula (1)
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ is a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 haloalkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkoxycarbonyl group, a C1- C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, or halogen atom, 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 group Alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, arylsulfonyloxy A C1-C4 alkyl group substituted by one or more substituents, which may be the same or different, selected from a group, a pentafluorosulfanyl group or an alkylsilyl group,
Y ₅ is,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Y ₃ is a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group, a C1-C6 perfluoroalkylsulfonyl group,
Trifluoromethyl group, C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkoxy group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylthio group,
Substituted C1 substituted by one or more substituents, which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group -C6 haloalkylsulfinyl group,
Or substituted with one or more substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group A substituted C1-C6 haloalkylsulfonyl group is shown. )
The pest control composition according to claim 1, which is a compound represented by: In the general formula (1), the compound represented by the general formula (1)
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (2)

(Where
Y ₁ is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, Or a C1-C6 haloalkylsulfonyl group,
Y ₅ is,
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- A C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, or a nitro group;
Y ₂ and Y ₄ may be the same or different,
A hydrogen atom, a halogen atom, a C1-C6 alkyl group,
Y ₃ represents a halogen atom. )
The pest control composition according to claim 1, which is a compound represented by: In the general formula (1), the compound represented by the general formula (1)
A ₁ represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
A ₂ , A ₃ and A ₄ represent carbon atoms,
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C4 alkyl group,
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or A dihydropyranyl group).
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, Or a dihydropyranyl group).
Q ₂ represents the general formula (4)

_(Wherein, Y 1, _{Y 5} may be the same or different,
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, nitro group,
Y ₂ and Y ₄ may be the same or different and each represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,
Ra represents a halogen atom or a hydroxy group,
Rb and Rc can each independently represent a halogen atom or a C1-C6 haloalkyl group, and at least one of Rb and Rc has at least one hydrogen atom, hydroxy group, chlorine atom, bromine atom, or iodine atom. Have )
The pest control composition according to claim 1, which is a compound represented by: The pest control composition according to any one of claims 1 to 5, wherein in the general formula (1), at least _one of R ₁ and R ₂ is a C1-C4 alkyl group. General formula (5)

{Wherein A ₁ , A ₂ , A ₃ , A ₄ each represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
Z represents —N (R ₁ ) SO ₂ Q ₁ or —N (R ₁ ) Q ₁ ;
R ₁ and R ₂ each independently represent a hydrogen atom, a C1-C4 alkyl group, or a C1-C4 alkylcarbonyl group,
G ₁ represents an oxygen atom or a sulfur atom,
X may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or a trifluoromethyl group,
n represents an integer of 0 to 4,
Q ₁ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, an amino group or a phenyl group ,
Carbocyclic group (the carbocyclic group here means a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group). ,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted carbocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The carbocyclic group here represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group.
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Or
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocycle having one or more substituents which may be the same or different and are selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, an amino group or a phenyl group Group (the heterocyclic group here is a pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, Thiazolyl, thiadiazolyl, pyrrole, imidazolyl, triazolyl, pyrazolyl, tetrazolyl, benzothiazolyl, benzoxazolyl, benzofuranyl, benzothiophenyl, quinolyl, isoquinolyl, indolyl, isoindolyl, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group).
Q ₂ is a phenyl group,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group;
Carbocyclic group (the carbocyclic group here means a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group). ,
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted carbocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The carbocyclic group here represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9-oxofluorenyl group, an adamantanyl group, or a norbornyl group.
Heterocyclic group (the heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group) Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H -Represents an isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a tetrahydropyranyl group, or a dihydropyranyl group.
Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl 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, A C1-C4 haloalkylcarbonyl group, 1-C4 alkylcarbonyloxy group, C1-C4 haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 A substituted heterocyclic group having one or more substituents which may be the same or different and selected from an alkylsulfonyloxy group, a C1-C4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group ( The heterocyclic group here is pyrazinyl group, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazo group. Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1H-isoindolyl group, 2,3-dihydro-benzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydropyranyl group).
A C1-C6 alkyl group,
Alternatively, a halogen atom, 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 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 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy Group, C1- 4-haloalkylcarbonyloxy group, C1-C4 alkoxycarbonyl group, C1-C4 haloalkoxycarbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkylcarbonylamino group, C1-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyl A substituted C1-C6 alkyl group having one or more substituents, which may be the same or different, selected from an oxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, or a phenyl group. } As an active ingredient, one or two or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides or known fungicides are contained. A pest control composition characterized by the above. Known insecticides, known acaricides or known fungicides are azinephos methyl, acephate, isoxathion, isofenphos, etion, etrimphos, oxydimethone methyl, oxydeprophos, quinalphos, chlorpyrifos, chlorpyrifosmethyl, chlorfenvinphos, cyanophos, Dioxabenzophos, dichlorvos, disulfoton, dimethylvinphos, dimethoate, sulprophos, diazinon, thiometone, tetrachlorbinphos, temefos, tebupyrimfos, terbufos, nared, bamidthione, pyraclofos, pyridafenthione, pyrimifosmethyl, fenitrothion, fenthion, fentoate, fentolfofo Thion, Flupyrazophos, Prothiophos, Propafos, Profenofos, Hoxime, Hosalon, Ho Met, formothion, folate, malathion, mecarbam, mesulfenphos, methamidophos, metidathion, parathion, methylparathion, monocrotophos, trichlorfone, O-ethylphenyl-4-phosphonothiothio, isazophosthiothiphosfothathionophos , Hosthiethane, phosphocarb, O-4-dimethylsulfamoylphenyl O, O-diethylphosphothioate, etoprophos, alanicarb, aldicarb, isoprocarb, etiophencarb, carbaryl, carbosulfan, xylcarb, pyricarb, pyricarb Nobucarb, furthiocarb, propoxyl, bendiocarb, benfuracarb, mesomil, metorcarb, 3,5-xylylmethylcarbamate, carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate, pentrin, cyclohalothrin, cyhalothrin, cyhalothrin , Lambda siharthrin, cyfluthrin, beta cyfluthrin, cypermethrin, alpha cypermethrin, zeta cypermethrin, silafluophene, tetramethrin, tefluthrin, deltamethrin, tralomethrin, bifenthrin, phenothrin, fenvalerate, fenpropatoline, framethrin fluretrin Nates, fulvalinates, flubrosinates , Permethrin, Resmethrin, Metofluthrin, Dimefluthrin, Profluthrin, Etofenprox, Cartap, Thiocyclam, Benzlutap, Acetamiprid, Imidacloprid, Clothianidin, Dinotefuran, Thiacloprid, Thiamethoxam, Nitenpyram, Flufluzuron, Flufluzuron Bistrifluron, fluazuron, flucycloxuron, flufenoxuron, hexaflumulone, lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyphenozide, diophenolan, cyromazine, pyriproxyfen, buprofezin, methoprene, hydroprene, quinoprene, triazamate, endosulfan The Rufenson, chlorbenzilate, dicophore, bromopropyrate, acetoprole, fipronil, etiprole, pyrethrin, rotenone, nicotine sulfate, abamectin, Bacillus thuringiensis, spinosad, acequinosyl, amideflumet, amitraz, etoxazole, quinomethionate, clofentezine , Phenbutadium oxide, dienochlor, cyhexatin, spirodiclofen, spiromesifen, tetradiphone, tebufenpyrad, binapacryl, bifenazate, pyridaben, pyrimidifene, phenazaquin, phenothiocarb, fenpyroximate, fluacrylimine, fluazinam, flufenzine, polyhexinactin, polyhexinactin Milbemectin, Ruff Nuron, mecarbam, methiocarb, mevinphos, formethanate, halfenprox, azadirachtin, diafenthiuron, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate, chlorfenapyr, tolfenpyrad, pymetrozine, phenoxycarb, hydramethylnon , Hydroxypropyl starch, pyridalyl, flufenelim, flubendiamide, flonicamid, metaflumizone, repimectin, tripropyrisocyclic, levamisole hydrochloride, morantel tartrate, dazomet, metam sodium,
General formula (AA)

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

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

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

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. ] The pest control composition of any one of Claims 1-7 which is a compound represented by these. Known insecticides, known acaricides or known fungicides are fenitrothion, fenthion, isoxathione, acephate, buprofezin, pyriproxyfen, silafluophene, dinotefuran, imidacloprid, etofenprox, halfenprox, thiamethoxam, clothianidin, acetamiprid, nitenpyram, thiacloprid , Benfuracarb, Mesomil, Fenobucarb, Spinosad, Pymetrozine, Chromafenozide, Lepimectin, Fipronil,
General formula (AA)

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

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

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

[Wherein R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R22 and R27 each represent a hydrogen atom, R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R25 and R26 each represent a hydrogen atom, and R28 represents an aryl group or a heterocyclic ring. Represents. ] The pest control composition of Claim 8 which is a compound represented by this. 10. One to one compound selected from a known insecticide, a known acaricide, or a known fungicide is contained in an amount of 0.001 to 95% by weight, respectively. Pest control composition. A pest control method comprising applying the pest control composition according to claim 10 to a pest or a habitat of the pest. A method for preventing damage by pests, which comprises applying the pest control composition according to claim 10 to plant seeds. A method for preventing damage by pests, comprising bringing the plant pest control composition into contact with plant seeds. The prevention method according to claim 13, wherein the method of contacting the plant seed is a spraying treatment, a smearing treatment, a dipping treatment or a powder coating treatment on the seed. Plant seeds are corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper and rape seed, taro, potato, The prevention method according to claim 12, which is a potato, konjac seed, edible lily or tulip bulb. The prevention method according to claim 15, wherein the plant seed is a transformed seed. A plant seed to which the pesticidal composition according to claim 10 is applied. A method for preserving plant seeds, comprising applying the pest control composition according to claim 10 to plant seeds. The preservation method according to claim 18, wherein the application method to the plant seed is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment or fumigation / smoke treatment. A method for preserving a crop, comprising applying the pest control composition according to claim 10 to a crop of an agricultural plant. 21. The storage method according to claim 20, wherein the application method to the harvest of the agricultural plant is spraying, smearing, coating, dipping, powdering, fumigation / smoke treatment, or pressure injection.