JP4679925B2 - Insecticide production method and production intermediate - Google Patents

Description

  The present invention relates to a method for producing a compound represented by the general formula (1) (Chemical formula 1) showing an excellent control effect as an insecticide and a production intermediate thereof.

[Wherein, A ₁ , A ₂ , A ₃ , A ₄ are each independently a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3- A C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group).
-E ₁ -Z ₁ -R ₄ (wherein E ₁ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3- C4 represents a haloalkynylene group,
R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group. A C3-C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
Z ₁ represents —O—, —S—, —SO—, —SO ₂ —, —C (═O) —, —C (═O) O—, —OC (═O) —, —N (R ₅ ) -, - C (= O ) N (R 5) -, - N (R 5) C (= O) - (R 5 is a hydrogen atom, C1-C4 alkyl group, C1-C4 alkylcarbonyl group, C1- A C4 haloalkylcarbonyl group and a C1-C4 alkoxycarbonyl group.). ),
—E ₂ —R ₆ — (wherein E ₂ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3-C4 haloalkynylene group). Group,
R ₆ is a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group). ) And
R ₂ and R ₃ are each independently a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group,
G ₁ , G ₂ and G ₃ are each independently an oxygen atom or a sulfur atom,
X may be the same or different, and may be a hydrogen atom, halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4. Substituted with haloalkylthio group, C1-C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, cyano group, nitro group, amino group, C1-C4 alkyl group An amino group that may be
n is an integer from 0 to 4,
R _a and R _b are each independently a fluorine atom or a C1-C4 perfluoroalkyl group,
Y ₁ , Y ₂ , Y ₄ and Y ₅ may be the same or different and are a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group. C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, pentafluorosulfanyl group, cyano group Represents a nitro group. (However, Y ₁ and Y ₅ do not represent hydrogen atoms at the same time.)]

  JP-A-11-511442 discloses a salicylic acid compound similar to the compound represented by formula (1) in the present invention, but this compound does not have a salicylic acid skeleton. In WO2003-22806, a compound similar to the compound represented by the general formula (1) in the present invention is described as a production intermediate, but there is no description about the activity against insects. J. et al. Org. Chem. 142 (1966) describes a compound similar to the compound represented by the general formula (1) in the present invention as a production intermediate, but does not describe any activity against insects. J. et al. Am. Chem. Soc. In 6382 (2000), a compound similar to the compound represented by the general formula (1) in the present invention is described as a production intermediate, but there is no description of activity against insects.

Japanese National Patent Publication No. 11-511442 WO2003-22806 J. et al. Org. Chem. 142 (1966) J. et al. Am. Chem. Soc. 6382 (2000)

An object of the present invention is to find a novel substance having insecticidal activity and to provide a production method and a production intermediate for producing the substance.

  The present inventors have found use as an insecticide because the compound represented by the general formula (1) is a compound not described in any literature and has a remarkably excellent insecticidal effect.

  Moreover, when manufacturing the compound represented by General formula (1), the compound represented by General formula (2) and General formula (3) which is a compound which is not described in literature is a useful manufacturing intermediate. I found it. As a result, the present invention has been completed.

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

[Wherein, A ₁ , A ₂ , A ₃ , A ₄ are each independently a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3- A C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group).
-E ₁ -Z ₁ -R ₄ (wherein E ₁ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3- C4 represents a haloalkynylene group,
R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group. A C3-C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
Z ₁ represents —O—, —S—, —SO—, —SO ₂ —, —C (═O) —, —C (═O) O—, —OC (═O) —, —N (R ₅ ) -, - C (= O ) N (R 5) -, - N (R 5) C (= O) - (R 5 is a hydrogen atom, C1-C4 alkyl group, C1-C4 alkylcarbonyl group, C1- A C4 haloalkylcarbonyl group and a C1-C4 alkoxycarbonyl group.). ),
-E ₂ -R ₆ (wherein E ₂ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3-C4 haloalkynylene group) Indicate
R ₆ may be a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, the same or different, a halogen atom, a C1-C6 alkyl group, a C1-C6 Haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group C1-C4 alkylcarbo Aryloxy group, a substituted phenyl group having one or more substituents selected from C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group). ) And
R ₂ and R ₃ are each independently a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group,
G ₁ , G ₂ and G ₃ are each independently an oxygen atom or a sulfur atom,
X may be the same or different, and may be a hydrogen atom, halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4. Substituted with haloalkylthio group, C1-C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, cyano group, nitro group, amino group, C1-C4 alkyl group An amino group that may be
n is an integer from 0 to 4,
R _a and R _b are each independently a fluorine atom or a C1-C4 perfluoroalkyl group,
R _c is a hydroxy group, —O—R _d (R _d is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group) Group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom,
Y ₁ , Y ₂ , Y ₄ and Y ₅ may be the same or different, and are a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group. C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, pentafluorosulfanyl group, cyano group Represents a nitro group (provided that Y ₁ and Y ₅ do not represent a hydrogen atom at the same time). ] The compound represented by this.
[2] General formula (3)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are [1 The same as described in the above.
[3] General formula (4)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₂ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ Represents the same as described in [1].) And a compound represented by the general formula (5)

(Wherein G ₁ , G ₂ and R ₁ are the same as those described in [1], and J represents a hydroxy group, a chlorine atom or a bromine atom). A process for producing a compound represented by the general formula (2) described in [1].
[4] General formula (6)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , (X) n are the same as those described in [1], J Represents the same as described in [3].) And a compound represented by the general formula (7)

(Wherein R ₃ , R _a , R _b , R _c , Y ₁ , Y ₂ , Y ₄ , Y ₅ are the same as those described in [1]). A process for producing a compound represented by the general formula (2) described in [1], wherein
[5] General formula (8)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , (X) n represents the same as described in [1], and J represents the same as described in [3]. And a compound represented by the general formula (9)

(In the formula, G ₂ and R ₁ are the same as those described in [1].) After reacting with the compound represented by [4], it is represented by the general formula (7) described in [4]. The compound of the general formula (2a)

(Where A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in [1].) To produce the compound represented by general formula (2) described in [1]. Method.
[6] General formula (10)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are [1 The compound represented by general formula (3) described in [2] is produced, wherein the compound represented by (2) is reacted with an isocyanating agent. Method.
[7] General formula (11)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are [1 The compound represented by general formula (3) described in [2] is produced by reacting the compound represented by (2) with a Curtius rearrangement agent. how to.

[8] The compound represented by the general formula (3) described in [2] is reacted with the compound represented by the general formula (9) described in [5], [5 ] The method to manufacture the compound represented by general formula (2a) described in this.

[9] A compound represented by the general formula (2) described in [1] is reacted with a fluorinating agent, the general formula (1) (chemical formula 13)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in [1].).
[10] General formula (2b) (Formula 14)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in [1].) The compound represented by [1] represented by general formula (2c) is reacted with a halogenating agent. (Chemical 15)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in [1], and R _c ′ represents a chlorine atom or a bromine atom.)

  According to this invention, the compound represented by General formula (1) which shows the outstanding control effect as an insecticide can be manufactured.

The terms used in the present invention have the meanings described below in their definitions.

  “Halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. “N-” means normal, “i-” means iso, “s-” means secondary, and “t-” means tertiary. The notation "Ca-Cb (a, b represents an integer of 1 or more)" means, for example, that "C1-C6" has 1 to 6 carbon atoms, and "C3-C8 "Means 3 to 8 carbon atoms, and" C1-C4 "means 1 to 4 carbon atoms.

  The “C1-C6 alkyl group” is, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl. A linear or branched alkyl group having 1 to 6 carbon atoms such as 2-pentyl, n-hexyl, 3-methyl-n-pentyl and the like, and the “C1-C6 haloalkyl group” includes, for example, Trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 1,3-difluoro-2-propyl, 1,3- Dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,2,2-trifluoroethyl, 2 2,2-trichloroethyl, 2,2,2-tribromoethyl, 3,3,3-trifluoro-n-propyl, 4,4,4-trifluoro-n-butyl, 1,1,1,3 , 3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 1,1,1,3,3,3-hexafluoro- 2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-2-bromo- n-propyl, 1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, 3,3,4, 4,4-pentafluoro-2-butyl, nonafluoro-n-butyl, nonafluoro-2-buty , 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl and the like may be the same or different A linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms is shown.

  The “C2-C6 alkenyl group” refers to an alkenyl group having 2 to 6 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl, etc. Examples of the “C6 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4 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 1,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc. Or a branched alkenyl group having 2 to 6 carbon atoms.

  The “C2-C6 alkynyl group” means, for example, 2 to 6 carbon atoms having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc. The “C2-C6 haloalkynyl group” is, for example, a linear or branched chain having a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. An alkynyl group having 2 to 6 carbon atoms.

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

  “C1-C6 alkoxy group” means, for example, a linear or branched carbon atom such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy and the like A C1-C6 haloalkoxy group refers to, for example, trifluoromethoxy, pentafluoroethoxy, heptafluoro-n-propyloxy, heptafluoro-i-propyloxy, 1,1 , 1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 3-fluoro-n-propyloxy, etc., which may be the same or different 1 A linear or branched haloalkoxy group having 1 to 6 carbon atoms substituted with one or more halogen atoms is shown.

  The “C1-C6 alkylthio group” is, for example, a linear or branched carbon atom number of 1 to 6 such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, t-butylthio and the like. A “C1-C6 haloalkylthio group” means, for example, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i -Linear or branched alkylthio having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as -propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, etc. Indicates a group.

  “C1-C6 alkylsulfinyl group” means, for example, linear or branched chain such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, etc. An alkylsulfinyl group having 1 to 6 carbon atoms, and examples of the “C1-C6 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, hepta One or more halogen atoms, which may be the same or different, such as fluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, etc. Ri indicates a substituted linear or branched chain having 1 to 6 carbon atoms, an alkylsulfinyl group.

  The “C1-C6 alkylsulfonyl group” is, for example, a linear or branched chain such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, etc. A C1-C6 haloalkylsulfonyl group is, for example, trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, hepta Straight chain substituted by one or more halogen atoms which may be the same or different, such as fluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl and the like Or branched It shows a 1-6 alkylsulfonyl group carbon atoms.

  The “C1-C4 alkylcarbonyl group” is, for example, a linear, branched or cyclic alkylcarbonyl group having 1 to 4 carbon atoms such as acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl, etc. The “—C4 haloalkylcarbonyl group” is substituted by one or more halogen atoms which may be the same or different, such as trifluoroacetyl, pentafluoropropionyl, trichloroacetyl, chloroacetyl, bromoacetyl, 3-chloropropionyl, etc. A linear or branched alkylcarbonyl group having 1 to 4 carbon atoms is shown.

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

  “C1-C4 alkylcarbonyloxy group” means, for example, a linear or branched alkylcarbonyloxy group having 1 to 4 carbon atoms such as acetoxy, propionyloxy, etc., and “C1-C4 alkylsulfonyloxy group” "Represents a linear or branched alkylsulfonyloxy group having 1 to 4 carbon atoms such as methylsulfonyloxy, and" C1-C4 haloalkylsulfonyloxy group "means, for example, trifluoromethylsulfonyl A linear or branched alkylsulfonyloxy group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as oxy and pentafluoroethylsulfonyloxy.

  “C1-C4 alkylene group” means, for example, a linear or branched alkylene group having 1 to 4 carbon atoms such as methylene, ethylene, propylene, dimethylmethylene, isobutylene, etc., and “C2-C4 alkenylene group” "Represents a linear or branched alkenylene group having 2 to 4 carbon atoms having a double bond in the carbon chain, and" C3-C4 alkynylene group " A linear or branched alkynylene group having 3 to 4 carbon atoms having a triple bond is shown, and the “C1-C4 haloalkylene group” includes, for example, chloromethylene, chloroethylene, dichloromethylene, difluoromethylene, etc. A linear or branched alkylene group having 1 to 4 carbon atoms, which is substituted with one or more halogen atoms which may be the same or different, is shown.

  The “C2-C4 haloalkenylene group” is a linear or branched carbon atom having a double bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. Represents -4 alkynylene groups, and the “C3-C4 haloalkynylene group” is linear or branched having a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different. A chain-like alkynylene group having 3 to 4 carbon atoms is shown.

  The compounds represented by the general formula (2) and the general formula (3) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in the structural formula, and two or more thereof. However, the present invention includes all the optical isomers and a mixture containing them in an arbitrary ratio. In addition, the compounds represented by the general formula (2) and the general formula (3) of the present invention may include two or more geometric isomers derived from a carbon-carbon double bond in the structural formula. However, the present invention encompasses all geometric isomers and mixtures containing them in any proportion.

  Moreover, the compound represented by the general formula (1) which is the object of the present invention is a novel compound having insecticidal activity. That is, the compound represented by the general formula (1) is a compound having a remarkable control effect against pests that damage paddy field crops, field crops, fruit trees, vegetables, other crops, and flower buds.

  Examples of pests to which the compound represented by the general formula (1) can be applied include, for example, diaphania indica, Homagna magnaima, Hellula undalis, apple wolfberry or adoxyphysica. Japanese red spider (Adoxophyces sp.), Japanese red spider black spider (Archips fuscocuppreanus), Japanese peach (Garphinopinus), Japanese stag beetle (Graphophrita inopinata), Japanese sardine (Grapholita sina Wahimehamaki (Olethreutes mori), mandarin orange leafminer (Phyllocnistis citrella), Kakinohetamushiga (Stathmopoda masinissa), Chanohosoga (Caloptilia theivora), apple moth subfraction (Caloptilia zachrysa), the apple leaf miner (Phyllonorycter ringoniella), Nashihosoga (Spulerrina astaurota), swallowtail butterfly (Papilio xuthus) , White butterfly (Pieris rapae curicivora), Heliothis armigera, codling moth (Lapsey resia pomonella) xylostella), apple Hime sink Lee (Argyresthia conjugella), rice stem borer (Chilo suppressalis), leaf roller (Cnaphalocrocis medinalis), tea moth (Ephestia elutella), Kuwanomeiga (Glyphodes pyloalis), Itten giant moth (Scirpophaga incertulas), parnara guttata (Parnara guttata ), Ayuyoto (Pseudaletia separata), Sonemia inferens, Myostraga (Mamestra brassicae), Spodoptera litura (Spodoptera litura) podoptera exigua), black cutworm (Agrotis ipsilon), Kaburayaga (Agrotis segetum), Tamanagin'uwaba (Autographa nigrisigna), Trichoplusia ni (Trichoplusia ni) lepidopteran pests such as, lid Ten leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), Japanese brown planthopper (Laodelfax striatellus), white-tailed planthopper (Sogataella furcifera), citrus leaf lice (Diaphorina citri), grape whitefly (Aleurolobus) ae), silver leaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), Onitsu aphia moss (Triaureodes vapariirum), larvae aphid (Lipaphis erythrum) Myzus persicae, hornworm (Ceroplasts ceriferus), stag beetle (Pseudococcus commnocki), stag beetle (Pranococcus kraunhiae), stag beetle (Panthococcus kraunhiae) ii), Pseudaonidia duplex, pesticide bug (Comstockcaspis perniciosa), papidae (Unaspis yanonisis), hemipoda reptilis (Platia staphylococci) (Anomala rubocupurea), beetle (Popilia japonica), tobacco beetle (Lasioderma serricorne), Lyctusbrunius, Lyctusbrunitius (Epitocina) hus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), Inemizusoumushi (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), Inedorooimushi (Oulema oryzae), Kisujinomihamushi (Phyllotreta striolata), pine Bark beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican beetle (Epilachna varivestis), cornle Toworms (Diabrotica sp. ), Psakothea hilaris, Anophora la la e) Flyfly (Asphondylia sp.), Housefly (Musca domestica), winged fly (Chromatomyia horticola), leafhopper (Liriomyza trifolipi), eggplant fly (Zirimolypi) Which dipterous pests, Pratylenchus coffeae, Pratylenchus sp., Potato cyst neus (Globodera rostisolens), Meloidogyne pneumoniae Pesticides such as nephews (Aphelenchus avenae) and nephews (Aphelenchoides ritzemabosi), Thrips palmi (Trips palmii), and Franklinccilialli rtothrips dorsalis), yellow thrips (thrips), thrips tabaci, etc. It is done.

  The compounds represented by the general formula (2) and the general formula (3) are production intermediates of the compound represented by the general formula (1), that is, the general formula (2) (chemical formula 16) is

[Wherein, A ₁ , A ₂ , A ₃ , A ₄ are each independently a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3- A C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group).
-E ₁ -Z ₁ -R ₄ (wherein E ₁ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3- C4 represents a haloalkynylene group,
R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group. A C3-C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
Z ₁ represents —O—, —S—, —SO—, —SO ₂ —, —C (═O) —, —C (═O) O—, —OC (═O) —, —N (R ₅ ) -, - C (= O ) N (R 5) -, - N (R 5) C (= O) - (R 5 is a hydrogen atom, C1-C4 alkyl group, C1-C4 alkylcarbonyl group, C1- A C4 haloalkylcarbonyl group and a C1-C4 alkoxycarbonyl group.). ),
-E ₂ -R ₆ (wherein E ₂ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3-C4 haloalkynylene group) Indicate
R ₆ is a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group). ) And
R ₂ and R ₃ are each independently a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group,
G ₁ , G ₂ and G ₃ are each independently an oxygen atom or a sulfur atom,
X may be the same or different, and may be a hydrogen atom, halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4. Substituted with haloalkylthio group, C1-C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, cyano group, nitro group, amino group, C1-C4 alkyl group An amino group that may be
n is an integer from 0 to 4,
R _a and R _b are each independently a fluorine atom or a C1-C4 perfluoroalkyl group,
R _c is a hydroxy group, —O—R _d (R _d is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group) Group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom,
Y ₁ , Y ₂ , Y ₄ and Y ₅ may be the same or different, and are a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group. C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, pentafluorosulfanyl group, cyano group Represents a nitro group (provided that Y ₁ and Y ₅ do not represent a hydrogen atom at the same time). And a compound represented by
The compound represented by the general formula (3) (chemical formula 17) is

[Wherein, A ₁ , A ₂ , A ₃ , A ₄ are each independently a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₃ is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group,
G ₃ is an oxygen atom or a sulfur atom,
X may be the same or different, and may be a hydrogen atom, halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4. Substituted with haloalkylthio group, C1-C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, cyano group, nitro group, amino group, C1-C4 alkyl group An amino group that may be
n is an integer from 0 to 4,
R _a and R _b each represent a fluorine atom or a C1-C4 perfluoroalkyl group,
R _c is a hydroxy group, —O—R _d (R _d is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C3 alkylcarbonyl group) Group or a C1-C3 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom,
Y ₁ , Y ₂ , Y ₄ and Y ₅ may be the same or different, and are a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group. C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, pentafluorosulfanyl group, cyano group Represents a nitro group (provided that Y ₁ and Y ₅ do not represent a hydrogen atom at the same time). It is a compound represented by this.

  Among the compounds represented by the above general formula (2) and general formula (3), preferred substituents or atoms are as follows.

R ₁ is preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group. , C3-C8 halocycloalkyl group, -E ₁ -Z ₁ -R ₄ (wherein, E ₁ is C1-C4 alkylene group, C2-C4 alkenylene group, C3-C4 alkynylene group, C1-C4 haloalkylene group, A C2-C4 haloalkenylene group and a C3-C4 haloalkynylene group, wherein R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group. group, a C2-C6 haloalkynyl group, Z ₁ is -O -, - S -, - SO -, - SO 2 - shows _{a), -. E 2 -R 6} ( wherein, E ₂ C1-C4 alkyl group, C2-C4 alkenyl group, C3-C4 alkynyl group, C1-C4 haloalkyl group, C2-C4 haloalkenyl group, a C3-C4 haloalkynyl group, R ₆ is C3-C8 cycloalkyl, C3-C8 halocycloalkyl group, cyano group, nitro group, hydroxy group, phenyl group, which 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, hydroxy group, C1-C4 alkylcal Nyl group, C1-C4 haloalkylcarbonyl group, C1-C4 alkylcarbonyloxy group, substituted phenyl group having one or more substituents selected from C1-C4 alkoxycarbonyl group, pyridyl group, halogen atom, C1-C6 haloalkyl group , A substituted pyridyl group having one or more substituents selected from C1-C6 haloalkoxy groups, and more preferably R ₁ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, -E ₁ -Z ₁ -R ₄ (wherein, E ₁ is C1-C4 alkylene group, a C1-C4 haloalkylene group, R ₄ is C1 —C6 alkyl group, and Z ₁ represents —O—, —S—, —SO—, —SO ₂ —. ), - E ₂ -R ₆ (wherein, E ₂ represents a C1-C4 alkyl group, R ₆ is C3-C8 cycloalkyl, cyano, be the same or different and a halogen atom, C1-C6 A substituted phenyl group having one or more substituents selected from a haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, and a nitro group , A pyridyl group, a halogen atom, a C1-C6 haloalkyl group, a substituted pyridyl group having one or more substituents selected from a C1-C6 haloalkoxy group, a thienyl group, and a tetrahydrofuran group.

R ₂ and R ₃ are preferably each independently a hydrogen atom or a C1-C4 alkyl group, more preferably a hydrogen atom, a methyl group, or an ethyl group.

R _a and R _b are preferably each independently a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group, or a heptafluoro-n-propyl group, and more preferably a fluorine atom, a trifluoromethyl group, a penta It is a fluoroethyl group.

R _c is preferably a hydroxy group, chlorine atom, bromine atom, iodine atom, methoxy group, ethoxy group, methylsulfonyloxy group, trifluoromethylsulfonyloxy group, phenylsulfonyloxy group, p-toluenesulfonyloxy group, acetoxy group , A trifluoroacetoxy group, more preferably a hydroxy group, a chlorine atom, or a bromine atom.

R _c ′ is preferably a hydroxy group.

R _c ″ is preferably a chlorine atom or a bromine atom.

G ₁ , G ₂ , and G ₃ are preferably each independently an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

  J is preferably a hydroxy group, a chlorine atom or a bromine atom, more preferably a chlorine atom.

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

n is preferably 0 or 1.
Y ₁ and Y ₅ are preferably independently of each other a hydrogen atom, a C1-C4 alkyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, or a trifluoromethyl group. , A trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, and a cyano group, and it is more preferable that the hydrogen atom is not shown at the same time.
Y ₂ and Y ₄ are preferably hydrogen atoms,
A ₁ is preferably a carbon atom, a nitrogen atom or an oxidized nitrogen atom
A ₂ , A ₃ and A ₄ are preferably carbon atoms.

  The compound represented by the general formula (2) can be produced by the production methods 1 to 4, 7 and 9 described below.

  Production method 1 (Formula 18) is a method for producing a compound represented by the general formula (2) by the following production method.

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , J, R ₁ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as described above, and R ₂ ′ represents a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, and a C1-C4 haloalkylcarbonyl group.)

1- (i) Step of General Formula (12) → General Formula (13) in Production Method 1 m-Nitrobenzoyl chloride derivative represented by general formula (12) and aromatic amine represented by general formula (7) By reacting the derivative in a solvent, a benzoic acid amide derivative represented by the general formula (13) can be produced. In this step, a base can also be used. The solvent used is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, Chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl isobutyl ketone and cyclohexanone, dimethylformamide, dimethylacetamide, etc. Amides, nitriles such as acetonitrile, and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents may be used alone or in admixture of two or more. Can do. 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 (10). The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected from a few minutes to 96 hours. The m-nitrobenzoyl chloride derivative represented by the general formula (12) can be easily produced from an m-nitrobenzoic acid derivative by a conventional method using a halogenating agent. Examples of the halogenating agent include halogenating agents such as thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride. Alternatively, as a method for producing the compound represented by the general formula (13) from the m-nitrobenzoic acid derivative and the compound represented by the general formula (7) without using a halogenating agent, for example, Chem. Ber. By following the method described on page 788 (1970), an additive such as 1-hydroxybenzotriazole can be used as appropriate, and a method using a condensing agent using N, N′-dicyclohexylcarbodiimide can be shown. Examples of other condensing agents include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide and 1,1′-carbonylbis-1H-imidazole. A mixed acid anhydride method using chloroformates can also be shown. Am. Chem. Soc. It can be produced by following the method described on page 5012 (1967). Examples of chloroformates include isobutyl chloroformate and isopropyl chloroformate. In addition to chloroformates, diethylacetyl chloride, trimethylacetyl chloride and the like can be illustrated. 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) Step of General Formula (13) → General Formula (10) in Production Method 1 A benzoic acid amide derivative having a nitro group represented by General Formula (13) is converted into General Formula (10) by a reduction reaction. To a benzoic acid amide derivative having an amino group represented by Examples of the reduction reaction include a method using a hydrogenation reaction and a method using stannous chloride (anhydride). The former is in a solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere. The reaction can be performed. 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 reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent to be used, and the reaction time may be appropriately selected from a few minutes to 96 hours. The latter is not limited to the conditions, but for example, see “Organic Synthesis” Coll. Vol. III By using the conditions described on page 453, the compound of the general formula (10) can be produced.

1- (iii) Step of General Formula (10) → General Formula (4a) in Production Method 1 The compound represented by general formula (10) is converted to a general formula (10) by using an aldehyde or a ketone under reducing reaction conditions. The compound represented by 4a) can be produced. Examples of the reduction reaction conditions include a method using a hydrogenation reaction and a method using sodium borohydride.

  In the former, any solvent may be used as long as it does not significantly inhibit the progress of this reaction. For example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene and toluene, diethyl Ethers such as ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; Amides such as dimethylformamide and dimethylacetamide; Nitriles such as acetonitrile and propionitrile; Ketones such as acetone, methyl isobutyl ketone and cyclohexanone , Esters such as ethyl acetate and butyl acetate, alcohols such as methanol, ethanol, n-propanol and i-propanol, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide, water, etc. Can indicate medium, these solvents may be mixed and used alone or in combination.

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

  Examples of the aldehyde include aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and bromoacetaldehyde.

  Examples of the ketone 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 appropriately selected from a few minutes to 96 hours.

  In the latter case, the solvent may be any solvent that does not significantly inhibit the progress of this reaction. For example, aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, methanol, ethanol, 1-propanol, 2-propanol And the like, solvents such as 1,3-dimethyl-2-imidazolidinone, water and the like can be used, and these solvents can be used alone or in admixture of two or more.

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

  Examples of the aldehyde include aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and bromoacetaldehyde.

  Examples of the ketone 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 appropriately selected from a few minutes to 96 hours.

1- (iv) Step of General Formula (4a) or General Formula (10) → General Formula (2) in Production Method 1 In the solvent, the compound represented by general formula (4a) or general formula (10) A base is added if necessary, a condensing agent is added if necessary, and a compound represented by the general formula (2) is produced by reacting with the compound represented by the general formula (5). Can do.

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

  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, Examples thereof include phosphates 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 the like.

  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 (4a) or the general formula (10), or may be used as a solvent.

  Examples of the condensing agent include N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1,1′-carbonylbis-1H-imidazole, and 1,1′-oxalyldiimidazole. And additives such as 1-hydroxybenzotriazole may be used as appropriate.

  These condensing agents may be appropriately selected and used within a range of 0.01 to 5 times molar equivalent to the compound represented by the general formula (4a) or the general formula (10).

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

  Production method 2 (Formula 19) is a method for producing a compound represented by the general formula (2), which is a compound of the present invention, from a readily available m-aminobenzoic acid ester derivative represented by the general formula (14). It is.

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , J, R ₁ , R ₂ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as described above, and R represents a lower alkyl group.)

2- (i) Process of General Formula (14) → General Formula (15) in Production Method 2 Benzoamide Derivative Having an Amino Group Represented by General Formula (14) and Compound Represented by General Formula (5) A compound represented by the general formula (15) can be produced by reacting (for example, chloroformates, chlorothioformates, chlorodiformate thioesters, etc.) in a solvent. In this step, a base can also be used. Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, and diethyl ether. , Linear or cyclic ethers such as dioxane, tetrahydrofuran and 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl isobutyl ketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide , Nitriles such as acetonitrile, and inert solvents such as 1,3-dimethyl-2-imidazolidinone, and these solvents can be used alone or in admixture of two or more. 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 (14). The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected from a few minutes to 96 hours.

2- (ii) Step of General Formula (15) → General Formula (16) in Production Method 2 Alkali hydroxide metal such as sodium hydroxide and potassium hydroxide, Alkali earth metal such as calcium hydroxide, The compound represented by the general formula (16) can be produced by a hydrolysis reaction according to a conventional method using inorganic acids such as hydrochloric acid and sulfuric acid.

2- (iii) General formula (16) in production method 2 → step of general formula (2) General formula (12) in production method 1 General formula (12) General formula (12) By performing a condensation reaction between the compound represented by (16) and the compound represented by the general formula (7), the compound of the present invention represented by the general formula (2) can be produced. Further, the general formula (16) is converted into a general formula (17) using a halogenating agent.

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , J, R ₁ , R ₂ , (X) n represents the same as above, Hal represents a fluorine atom, A compound represented by general formula (2) is produced, and then amidated with a compound represented by general formula (7) to produce a compound represented by general formula (2). You can also The reaction in the halogenation step and the amidation step can be carried out according to the method described in the step of the general formula (12) → general formula (13) of production method 1.

  The following production method 3 (Chemical Formula 21) produces a thioamide compound that is a compound represented by the general formula (2d), which is a compound of the present invention, from a compound represented by the general formula (4b) using a Lawson reagent. Is the method.

(Wherein G ₁ , G ₂ , R ₁ , R ₂ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are the same as above. Show.)

3- (i) Process of general formula (4b) → general formula (4c) in production method 3 Manufacturing by following the conditions described in Synthesis page 463 (1993), Synthesis page 829 (1984), etc. However, the conditions such as the solvent are not limited to those described in the literature.

3- (ii) Step of General Formula (4c) → General Formula (2d) in Production Method 3 Production using compound represented by general formula (5) (for example, chloroformate or chlorothioformate) The compound of the present invention represented by the general formula (2d) can be produced by appropriately selecting from the reaction conditions shown in the step of the general formula (4a) or the general formula (10) → the general formula (2) of the method 1. Is possible.

  Production Method 4 (Chemical Formula 22) uses 3-isocyanate benzoic acid chlorides represented by general formula (18) as starting materials, alcohols and thiols represented by general formula (9), and general formula (7 ) In order to produce the compound of the present invention represented by the general formula (2a). This method is described in J. Org. Org. Chem. The method is described on page 142 (1966).

(In the formula, G ₂ , R ₁ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are the same as described above.)
Process of general formula (18) → general formula (2a) in production method 4

  In this step, the reaction can be carried out in a solvent. Examples of usable solvents include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, and dioxane. Chain, cyclic ethers such as tetrahydrofuran and 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl isobutyl ketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, Nitriles such as acetonitrile and inert solvents such as 1,3-dimethyl-2-imidazolidinone can be used, and these solvents can be used alone or in admixture of two or more. Moreover, the progress of the reaction may be accelerated by adding a base. In addition to the bases described in the literature, organic bases such as triethylamine, pyridine and 4-dimethylaminopyridine, inorganic bases such as potassium carbonate, etc. Can be shown. These bases may be appropriately selected and used within a range of 0.01 to 5 times molar equivalent to the compound represented by the general formula (18). The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected from a few minutes to 96 hours.

  The compound represented by the general formula (3) can be produced by the production methods 5 and 6 described below.

  Production Method 5 (Chemical Formula 23) is a method for producing the compound of the present invention represented by General Formula (3) from the compound represented by General Formula (10) described in Production Method 1.

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are the same as above. Indicates the same thing.)

  In this step, an isocyanating agent is used, and “Organic Synthesis” Coll. Vol. II The compound represented by the general formula (3) is produced by the method described on page 453. The isocyanating agent referred to in the present invention is a reaction agent that converts an amino group into an isocyanato group, and examples thereof include phosgene, phosgene dimer, triphosgene, and oxalyl chloride. In this step, a solvent may be used as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, dichloromethane, chloroform, Halogenated hydrocarbons such as carbon chloride, linear or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, acetone, methyl isobutyl ketone, cyclohexanone, etc. Ketones, amides such as dimethylformamide, dimethylacetamide and the like, nitriles such as acetonitrile, and inert solvents such as 1,3-dimethyl-2-imidazolidinone. The above can be mixed and used. The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected from a few minutes to 96 hours.

  The isocyanate compound represented by the general formula (3), which is the compound of the present invention, is reacted with the isophthaloyl chloride derivative represented by the general formula (19) and C1-C6 lower alcohols, and then the general formula (7 ), And then using the Curtius rearrangement agent for the compound represented by the general formula (11) obtained by hydrolysis reaction, the method described in Macromolecules, page 1046 (1998). It can be produced by following the production method 6 (Chemical Formula 24) using a sequential Curtius rearrangement (Curtius rearrangement) reaction.

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are the same as above. R ′ represents a lower alkyl group or a benzyl group.)

  The Curtius rearrangement agent referred to in the present invention is a reaction agent that contributes to a series of reactions for converting a carboxyl group into an isocyanato group. Generally, after a carboxyl group is converted to a chloroformyl group, sodium azide is reacted. Convert to isocyanato group.

  In this step, a solvent may be used. Examples of usable solvents include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, diethyl ether, dioxane, Chain or cyclic ethers such as tetrahydrofuran and 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl isobutyl ketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, acetonitrile Inert solvents such as nitriles such as 1,3-dimethyl-2-imidazolidinone, and the like can be used alone or in admixture of two or more. The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected from a few minutes to 96 hours. In producing the compound represented by the general formula (3), alcohols used include ethanol, propanol, benzyl alcohol and the like. In the ester decomposition, a hydrolysis reaction or catalytic hydrogen by a conventional method is used. A reduction reaction can be shown.

  From the compound represented by the general formula (3) which is the compound of the present invention, the compound represented by the general formula (2a) which is the compound of the present invention can be produced according to Production Method 7 (Chemical Formula 25).

_{(Wherein, A 1, A 2, A} 3, A 4, G 1, G 2, G 3, R 1, R 3, R a, R b, R c, (X) n, Y 1, Y 2 , Y ₄ and Y ₅ are the same as above.)

  Using the compounds represented by the alcohols and thiols represented by the general formula (9), the compound of the present invention represented by the general formula (2a) is appropriately selected from the reaction conditions shown in the production method 4. It is possible to manufacture.

  From the compound represented by the general formula (2), the compound represented by the general formula (1) can be produced according to the production method 8 (Chemical Formula 26).

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as above.)

  In this step, the compound represented by the general formula (1) can be produced by reacting the compound represented by the general formula (2) with a fluorinating agent in a solvent or without a solvent. In this step, an additive can also be used.

  Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, chloroform, and the like. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, Nitriles such as propionitrile, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide, water and other solvents can be used, and these solvents are used alone or in combination of two or more. be able to.

  As the fluorinating agent, 1,1,2,2-tetrafluoroethyldiethylamine, 2-chloro-1,2,2-trifluoroethyldiethylamine, trifluorodiphenylphosphorane, difluorotriphenylphosphorane, fluoroformate esters, Sulfur tetrafluoride, potassium fluoride, potassium hydrogen fluoride, cesium fluoride, rubidium fluoride, sodium fluoride, lithium fluoride, antimony fluoride (III), antimony fluoride (V), zinc fluoride, fluoride Cobalt, lead fluoride, copper fluoride, mercury fluoride (II), silver fluoride, silver fluoroborate, thallium fluoride (I), molybdenum fluoride (VI), arsenic fluoride (III), bromine fluoride, Selenium tetrafluoride, tris (dimethylamino) sulfonium difluorotrimethylsilicate, sodium hexa Fluorosilicate, quaternary ammonium fluoride, (2-chloroethyl) diethylamine, diethylaminosulfur trifluoride, morpholinosulfur trifluoride, silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid, hydrogen fluoride pyridine complex, fluorine Hydrogen fluoride triethylamine complex, hydrogen fluoride salts, bis (2-methoxyethyl) aminosulfur trifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone, iodine pentafluoride, tris (diethylamino) phosphonium Examples include -2,2,3,3,4,4-hexafluoro-cyclobutane ylide, triethylammonium hexafluorocyclobutane ylide, and hexafluoropropene. These fluorinating agents can be used alone or in admixture of two or more. These fluorinating agents may be used in the range of 1 to 10-fold molar equivalent with respect to the compound represented by the general formula (2), or appropriately selected as a solvent.

  Examples of additives include crown ethers such as 18-crown-6, phase transfer catalysts such as tetraphenylphosphonium salts, non-base salts such as calcium fluoride and calcium chloride, metal oxides such as mercury oxide, An ion exchange resin or the like can be shown, and these additives can be used not only in the reaction system but also as a pretreatment agent for the fluorinating agent.

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

  From the compound represented by the general formula (2b) which is the compound of the present invention, the compound represented by the general formula (2c) which is the compound of the present invention can be produced according to the following production method 9 (Chemical Formula 27). .

(Where A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , R _c ′, (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as above.)

  The compound represented by the general formula (2b) can be produced by reacting the compound represented by the general formula (2b) with a halogenating agent in a solvent or without a solvent. In this step, an appropriate additive can be used.

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

  Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, Rydon reagents, methanesulfonyl chloride, p-toluenesulfonyl chloride, benzene. Sulfonyl halides such as sulfonyl chloride, sulfonium halides, sulfonate esters, chlorine, bromine, iodine, hypohalite esters, N-halogenamines, hydrogen chloride, hydrogen bromide, sodium bromide, odor Potassium chloride, cyanuric chloride, 1,3-dichloro-1,2,4-triazole, titanium (IV) chloride, vanadium (IV) chloride, arsenic (III), N, N-diethyl-1,2,2- Trichlorovinylamine, trichloroacetonitrile, sodium chloride, ammonium bromide, N chloride N- dimethyl chloroformate mini um bromide N, N- dimethyl chloroformate mini um, N, N- dimethylformamide, may indicate the like dichloride N, N- dimethyl phosphoamidine.

  Examples of additives include metal salts such as zinc chloride and lithium bromide, phase transfer catalysts, organic bases such as hexamethylphosphoric triamide, inorganic acids such as sulfuric acid, N, N-dimethylformamide and the like. it can.

  These halogenating agents may be appropriately selected within the range of 0.01 to 10-fold molar equivalents relative to the compound represented by the general formula (2b), or may be used as a solvent.

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

  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, but may be purified by operations such as recrystallization, column chromatography, and distillation as necessary. it can. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

  Tables 1 and 2 below show typical compounds represented by the general formula (2) and the general formula (3) which are the compounds of the present invention, but the present invention is not limited to these. Absent.

  Moreover, although the compound represented by General formula (1) which shows the outstanding control effect as an insecticide obtained by the manufacturing method of this invention at Table 3 is shown, this invention is not limited to these.

  In the table, “n-” represents normal, “i-” represents iso, “Me” represents a methyl group, “H” represents a hydrogen atom, “O” represents an oxygen atom, and “S” represents sulfur. “C” is a carbon atom, “N” is a nitrogen atom, “F” is a fluorine atom, “Cl” is a chlorine atom, “Br” is a bromine atom, “CF3” is trifluoromethyl. “C2F5” represents a pentafluoroethyl group, “OH” represents a hydroxy group, and “N—O” represents an N-oxide group.

  Moreover, each symbol of R1, R2, R3, Ra, Rb, Rc, A1, G1, G3, Y1, Y2, Y4, Y5, (X) n described in Table 1 is a substitution of the general formula (2). Each symbol of R3, Ra, Rb, Rc, A1, G3, Y1, Y2, Y4, Y5, (X) n described in Table 2 represents a substituent of the general formula (3). Each symbol of R1, R2, R3, Ra, Rb, Rc, A1, G1, G3, Y1, Y2, Y4, Y5, (X) n described in Table 3 is represented by the general formula (2). Represents a substituent. In Tables 1 to 3, the number before the substituent in the column of (X) n indicates the substitution position. For example, H in the column indicates that all substituents at the 2-position, 4-position, 5-position and 6-position are hydrogen atoms, and 2-F is substituted with a fluorine atom at the 2-position, and the other 4-position, The substitution positions at the 5th and 6th positions are hydrogen atoms.

Hereinafter, Table 4 shows physical property values of the compound represented by the general formula (1) which is a pest control agent obtained by the production method of the present invention. The ¹ H-NMR shift values shown here use tetramethylsilane as an internal reference substance and deuterated chloroform as a solvent unless otherwise specified.

  The following examples illustrate the invention in more detail, but the invention is not limited thereto.

N- [2,6-dimethyl-4- (1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl) phenyl] 3- (2,2,2-trichloroethoxycarbonylamino ) Preparation of benzamide (Compound No. 1) 2,6-Dimethyl-4- (1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl) aniline (1.80 g, 6. 27 (mmol) and pyridine (0.50 g, 6.30 mmol) in THF (20 ml) were added 3- (2,2,2-trichloroethoxycarbonylamino) benzoic acid chloride (2.00 g, 6.04 mmol), Stir at room temperature. After diluted with ethyl acetate and washed with 1N aqueous sodium hydroxide solution and 1N aqueous hydrochloric acid solution, the solvent was distilled off and purified by column chromatography (silica gel, hexane / ethyl acetate = 4/1) to give the title compound ( 5.07 mmol, 84%). ¹ H-NMR (CDCl ₃ ) δ 2.31 (6H, s), 3.99 (1H, s), 4.85 (2H, s), 7.15 (1H, br-s), 7.45- 7.51 (4H, m), 7.64-7.66 (2H, m), 8.01 (1H, s)

N- [2,6-dimethyl-4- (2-chloro-1,1,1,3,3,3-hexafluoro-2-propyl) phenyl] 3- (2,2,2-trichloroethoxycarbonylamino ) Preparation of benzamide (Compound No. 6) N- [2,6-Dimethyl-4- (1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl) phenyl] 3- ( Pyridine (0.01 g) was added to a mixture of 2,2,2-trichloroethoxycarbonylamino) benzamide (1.0 g, 1.72 mmol) and thionyl chloride (2 ml), and the mixture was refluxed for 4 hours. Concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane / ethyl acetate = 9/1 → 4/1) to obtain the title compound (1.46 mmol, 85%). ¹ H-NMR (CDCl ₃ ) δ 2.32 (6H, s), 4.84 (2H, s), 7.22 (1H, s), 7.47-7.54 (4H, m), 7 .56 (1H, s), 7.64 (1H, d, J = 7.8 Hz), 8.04 (1H, s). MS (APCI) = 600.91 (M + 2)

N- [2,6-dimethyl-4- (1,1,1,2,3,3,3-heptafluoro-2-propyl) phenyl] 3- (2,2,2-trichloroethoxycarbonylamino) benzamide Production of (Compound No. 95) N- [2,6-dimethyl-4- (2-chloro-1,1,1,3,3,3-hexafluoro-2-propyl) phenyl] 3- (2, To a DMF solution (10 ml) of 2,2-trichloroethoxycarbonylamino) benzamide (0.11 g, 0.18 mmol) was added potassium fluoride (0.10 g, 1.72 mmol), and the mixture was stirred at room temperature for 3 hours. The solvent was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with water, concentrated, and purified by column chromatography (silica gel, hexane / ethyl acetate = 4/1) to give the title compound (0.14 mmol). 78%). ¹ H-NMR (CDCl ₃ ) δ 2.33 (6H, s), 4.84 (2H, s), 7.29 (1H, br), 7.35 (2H, s), 7.47 (1H) , T, J = 7.8 Hz), 7.58 (1H, s), 7.64-7.66 (2H, m), 8.04 (1H, s)

  The insecticide containing the compound represented by the general formula (1) in the present invention as an active ingredient is a variety of agricultural, forestry, horticultural, stored grain pests, sanitary pests or lines that damage rice, fruit trees, vegetables, other crops, and florets. Suitable for pest control such as insects.

  In order to clarify that the compound represented by the general formula (1) in the present invention has excellent insecticidal activity, test examples are shown below, but the present invention is not limited thereto.

Test Example 1 Insecticidal test against Spodoptera litura Cabbage leaf pieces were immersed for 30 seconds in a chemical solution diluted with a predetermined concentration of the test compound, air-dried, put into a 7 cm polyethylene cup, and second-instar larvae of Spodoptera litura were released. The sample was left in a constant temperature room at 25 ° C., and the number of live and dead insects was examined after 3 days. It was done in two lanes in 1 ward and 5 animals.

  As a result, at 1000 ppm, Compound No. 95, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127 The compound showed a mortality rate of 70% or more.

Test Example 2 Insecticidal test against black moth (Plutella xylostella) Cabbage leaf pieces were immersed for 30 seconds in a chemical solution in which a test compound was diluted to a predetermined concentration and air-dried. The sample was left in a constant temperature room at 25 ° C., and the number of live and dead insects was examined after 3 days. It was done in two lanes in 1 ward and 5 animals.

  As a result, at 1000 ppm, Compound No. 95, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127 The compound showed a mortality rate of 70% or more.

Claims (10)

General formula (2)

[Wherein, A ₁ , A ₂ , A ₃ , A ₄ are each independently a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
R ₁ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3- A C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group).
-E ₁ -Z ₁ -R ₄ (wherein E ₁ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3- C4 represents a haloalkynylene group,
R ₄ is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group. A C3-C8 halocycloalkyl group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
Z ₁ represents —O—, —S—, —SO—, —SO ₂ —, —C (═O) —, —C (═O) O—, —OC (═O) —, —N (R ₅ ) -, - C (= O ) N (R 5) -, - N (R 5) C (= O) - (R 5 is a hydrogen atom, C1-C4 alkyl group, C1-C4 alkylcarbonyl group, C1- A C4 haloalkylcarbonyl group and a C1-C4 alkoxycarbonyl group.). ),
-E ₂ -R ₆ (wherein E ₂ is a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, a C3-C4 haloalkynylene group) Indicate
R ₆ is a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group,
Phenyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted phenyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
A naphthyl group,
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted naphthyl group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group,
Heterocyclic group (the heterocyclic group here is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, Isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group).
May be the same or different, and may be a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, nitro group, hydroxy group A substituted heterocyclic group having one or more substituents selected from a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group (Heterocycle here Is a pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group Group, thiadiazolyl group, pyrrole group, imidazolyl group, triazolyl group, pyrazolyl group and tetrazolyl group). ) And
R ₂ and R ₃ are each independently a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group,
G ₁ , G ₂ and G ₃ are each independently an oxygen atom or a sulfur atom,
X may be the same or different, and may be a hydrogen atom, halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4. Substituted with haloalkylthio group, C1-C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, cyano group, nitro group, amino group, C1-C4 alkyl group An amino group that may be
n is an integer from 0 to 4,
R _a and R _b are each independently a fluorine atom or a C1-C4 perfluoroalkyl group,
R _c is a hydroxy group, —O—R _d (R _d is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group) Group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom,
Y ₁ , Y ₂ , Y ₄ and Y ₅ may be the same or different, and are a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group. C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, pentafluorosulfanyl group, cyano group Represents a nitro group (provided that Y ₁ and Y ₅ do not represent a hydrogen atom at the same time). ] The compound represented by this. General formula (3)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are claims) 1 is the same as described in 1.). General formula (4)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₂ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ Represents the same as described in claim 1) and a compound represented by the general formula (5)

(Wherein G ₁ , G ₂ and R ₁ are the same as those described in claim 1, and J represents a hydroxy group, a chlorine atom or a bromine atom). A process for producing a compound represented by the general formula (2) according to claim 1. General formula (6)

(In the formula, A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , (X) n are the same as those described in claim 1; Represents the same as described in claim 3.) and a compound represented by the general formula (7)

(Wherein R ₃ , R _a , R _b , R _c , Y ₁ , Y ₂ , Y ₄ , Y ₅ are the same as those described in claim 1). A method for producing a compound represented by the general formula (2) according to claim 1, wherein: General formula (8)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , (X) n represents the same as described in claim 1, and J represents the same as described in claim 3. And a compound represented by the general formula (9)

(In the formula, G ₂ and R ₁ are the same as those described in claim 1), and then reacted with the compound represented by general formula (7) described in claim 4. The compound of the general formula (2a)

(Where A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in claim 1). A compound represented by general formula (2) described in claim 1 is produced. Method. General formula (10)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are claims) The compound represented by the general formula (3) according to claim 2 is produced by reacting the compound represented by (1) with an isocyanating agent. Method. Formula (11) (Formula 11)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₃ , R ₃ , R _a , R _b , R _c , (X) n, Y ₁ , Y ₂ , Y ₄ , Y ₅ are claims) The compound represented by general formula (3) according to claim 2 is produced by reacting the compound represented by (1) with a Curtius rearrangement agent. how to.   The compound represented by the general formula (3) described in claim 2 and the compound represented by the general formula (9) described in claim 5 are reacted. A method for producing a compound represented by the general formula (2a). A compound represented by the general formula (2) according to claim 1 is reacted with a fluorinating agent.

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in claim 1). Formula (2b) (Formula 13)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , (X) n, Y ₁ , Y ₂ , Y ₄ and Y ₅ are the same as those described in claim 1), wherein the compound according to claim 1 is reacted with a halogenating agent. (Chemical formula 14)

(Wherein A ₁ , A ₂ , A ₃ , A ₄ , G ₁ , G ₂ , G ₃ , R ₁ , R ₂ , R ₃ , R _a , R _b , (X) n, Y ₁ , Y ₂ , Y _4, Y ₅ have the same meanings as described in claim 1, R _c 'is a method for producing a compound represented by a chlorine atom or a bromine atom.).