WO2013191189A1

WO2013191189A1 - Fused heterocyclic compound

Info

Publication number: WO2013191189A1
Application number: PCT/JP2013/066768
Authority: WO
Inventors: 政樹 ▲高▼橋; 貴將田邊; 舞衣伊藤; 千枝清水; 吉彦野倉
Original assignee: 住友化学株式会社
Priority date: 2012-06-21
Filing date: 2013-06-12
Publication date: 2013-12-27

Abstract

This fused heterocyclic compound represented in formula (1) has excellent pest controlling effectiveness, and is useful as an active ingredient in pest control agents. (In the formula, A¹ represents -NR⁶-, an oxygen atom or a sulphur atom, R¹ represents a C1-C6 chain hydrocarbon group, etc., R², R³, R⁴, and R⁵ are the same or different and represent a C1-C6 chain hydrocarbon group, etc., optionally having one or more halogen atoms, R⁶ represents a C1-C6 chain hydrocarbon group, etc., R⁷ and R⁸ are the same or different and represent a C1-C6 chain hydrocarbon group, etc., and n represents 0, 1 or 2.)

Description

Fused heterocyclic compounds

The present invention relates to certain condensed heterocyclic compounds and their use for pest control.

WO 88/02367 describes fused heterocyclic compounds that can be used in pharmaceuticals.

The present invention provides a compound having an excellent control effect against pests and a method for controlling pests using the compound.
The present invention is as follows.
[1] Formula (1)

[Where:
A ¹ represents —NR ⁶ —, an oxygen atom or a sulfur atom,
R ¹ may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, or one or more atoms or groups selected from group Y. Represents a C3-C6 alicyclic hydrocarbon group,
R ² , R ³ , R ⁴ and R ⁵ are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, -OR ¹⁰ , -S (O) _m R ¹⁰ ^{^{_{^{, -NR 10 R 11, -CR 2}}}} R 10, -C (O) R 10, represents a cyano group, a nitro group, a halogen atom, an -SF ₅ or a hydrogen atom,
R ⁶ may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, and one or more atoms or groups selected from group Y. C3-C6 alicyclic hydrocarbon _group, -CO ² R 10, represents -C ^{(O) R 10} or a hydrogen atom,
R ⁷ and R ⁸ are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, -OR ¹⁰ , -S (O) _m R ¹⁰ , -S (O) ₂ NR ¹⁰ R ¹¹ , -NR ¹⁰ R ¹¹ , -NR ¹⁰ CO ₂ R ¹¹ , -NR ¹⁰ C (O) R ¹¹ , -CO ₂ R ¹⁰ , -C (O) R ¹⁰ , A cyano group, a nitro group, a halogen atom, —SF ₅ or a hydrogen atom;
R ⁹ is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , -C (O) R ^{10 represents} a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ¹⁰ and R ¹¹ are the same or different and each represents a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms,
m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, R ⁷ and R ⁸ do not simultaneously represent a hydrogen atom, and in —S (O) _m R ¹⁰ , when m is 1 or 2, R ¹⁰ does not represent a hydrogen atom.
Group X: C1-C6 alkoxy group optionally having one or more halogen atoms, C2-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms C2-C6 alkynyloxy group which may have one or more, C1-C6 alkylsulfanyl group which may have one or more halogen atoms, C1-C6 alkylsulfinyl group which may have one or more halogen atoms A C1-C6 alkylsulfonyl group which may have one or more halogen atoms, a C2-C6 alkylcarbonyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkoxycarbonyl group, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group The group consisting of fine-halogen atom.
Group Y: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of a C2-C6 alkenyloxy group optionally having one, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a hydroxy group and a halogen atom.
Group Z: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylsulfanyl group optionally having one or more, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 optionally having one or more halogen atoms Alkylsulfonyl group, C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylamino group optionally having one or more, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, and The group consisting of Toro group. ]
A condensed heterocyclic compound represented by the following (hereinafter referred to as the present compound).
[2] R ⁷ and R ⁸ are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, —OR ¹⁰ , —S (O) _m R ¹⁰ , halogen The compound of [1], which is an atom or a hydrogen atom.
[3] The compound according to [1] or [2], wherein R ⁹ is a hydrogen atom.
[4] R ¹ , R ⁴ and R ⁵ are the same or different and are a hydrogen atom or a halogen atom, and R ³ may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, The compound according to [1] to [3], which is —OR ¹⁰ , a halogen atom or a hydrogen atom.
[5] The compound according to [1] to [4], wherein A ¹ is —NR ⁶ —.
[6] A ¹ is —NR ⁶ —, and R ⁶ may be a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, or may have one or more halogen atoms. The compound according to [1] to [4], which is a good (C1-C6 alkoxy) C1-C6 alkyl group or a cyclopropyl group.
[7] The compound according to [1] to [4], wherein A ¹ is an oxygen atom.
[8] The compound according to [1] to [4], wherein A ¹ is a sulfur atom.
[9] A pest control composition comprising the compound according to any one of [1] to [8] and an inert carrier.
[10] A method for controlling pests, which comprises applying an effective amount of the compound according to any one of [1] to [8] to a pest or a pest habitat.

Examples of groups used in the description of the present specification will be described below.
In the present specification, the description of the Ca—Cb chain hydrocarbon group represents a linear or branched saturated or unsaturated hydrocarbon group having a to b carbon atoms.
The notation of the Ca—Cb alkyl group represents a linear or branched hydrocarbon group having a to b carbon atoms.
Examples of the “C1-C6 chain hydrocarbon group” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, and a hexyl group. A C1-C6 alkyl group such as, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl C2-C6 alkenyl groups such as 1-pentenyl group and 1-hexenyl group; and C2-C6 such as ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group and 1-hexynyl group An alkynyl group is mentioned.
The notation of the Ca-Cb alkenyl group refers to an unsaturated hydrocarbon group having one or more double bonds in the molecule, which is linear or branched having a carbon number of a to b. To express.
Examples of the “C2-C6 alkenyl group” include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3 -A butenyl group, 1-pentenyl group, and 1-hexenyl group are mentioned.
The notation of the Ca-Cb alkynyl group represents an unsaturated hydrocarbon group having a linear or branched chain structure having a to b carbon atoms and having one or more triple bonds in the molecule. .
Examples of the “C2-C6 alkynyl group” include ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group and 1-hexynyl group.
The notation of Ca—Cb alkoxy group represents a linear or branched alkyl-O— group having a to b carbon atoms.
Examples of the “C1-C6 alkoxy group” include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, neopentyloxy group and hexyl. An oxy group is mentioned.
The notation of the Ca-Cb alkenyloxy group is an alkenyl-O- group which is linear or branched having 1 to 2 carbon atoms and has one or more double bonds in the molecule. Represents.
Examples of the “C2-C6 alkenyloxy group” include a vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, 1-methylvinyloxy group, 2-methyl-1-propenyloxy group, 1-butenyloxy group, 2 -Butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group and 1-hexenyloxy group are mentioned.
The notation of a Ca-Cb alkynyloxy group is an alkynyl-O- group which is linear or branched having 1 to 2 carbon atoms and has one or more triple bonds in the molecule. To express.
Examples of the “C2-C6 alkynyloxy group” include ethynyloxy group, propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group and 1-hexynyloxy group.
The notation of the Ca—Cb alkylsulfanyl group represents a linear or branched alkyl-S— group having a to b carbon atoms.
Examples of the “C1-C6 alkylsulfanyl group” include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl group, and a hexylsulfanyl group.
The notation of the Ca—Cb alkylsulfinyl group represents a linear or branched alkyl-S (O) — group having a to b carbon atoms.
Examples of the “C1-C6 alkylsulfinyl group” include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, and a hexylsulfinyl group.
The notation of the Ca—Cb alkylsulfonyl group is linear or branched alkyl-S (O) having a to b carbon atoms.₂-Represents a group.
Examples of the “C1-C6 alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, and a hexylsulfonyl group.
The notation of Ca—Cb alkylcarbonyl group represents a linear or branched alkyl-C (O) — group having a to b carbon atoms.
Examples of the “C2-C6 alkylcarbonyl group” include an acetyl group, a propionyl group, a butyryl group, a pentanoyl group, and a hexanoyl group.
The notation of Ca—Cb alkoxycarbonyl group represents a linear or branched alkyl-O—C (O) — group having a to b carbon atoms.
Examples of the “C2-C6 alkoxycarbonyl group” include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, and a tert-butoxycarbonyl group.
The notation of the Ca—Cb alicyclic hydrocarbon group represents a cyclic non-aromatic hydrocarbon group having a to b carbon atoms.
Examples of the “C3-C6 alicyclic hydrocarbon group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a 2-cyclohexenyl group, and a 3-cyclohexenyl group.
The notation of Ca—Cb cycloalkyl group represents a cyclic alkyl group having a to b carbon atoms.
Examples of the “C3-C6 cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
The notation of Ca—Cb alkylamino group represents a linear or branched alkyl-NH— group having a to b carbon atoms.
Examples of the “C1-C6 alkylamino group” include a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, and a butylamino group.
The notation of the Ca-Cb dialkylamino group may be a linear or branched dialkylamino in which the number of carbon atoms of the alkyl group may be the same or different, and the total number of carbon atoms is a to b. Represents a group.
Examples of the “C2-C8 dialkylamino group” include a dimethylamino group, a diethylamino group, and a dipropylamino group.
The notation of the Ca-Cb alkoxyalkyl group may be the same or different from each other in the number of carbon atoms of the alkyl group, and a linear or branched alkyl group in which the total number of carbon atoms is a to b. Represents an O-alkyl group.
Examples of the “(C1-C6 alkoxy) C1-C6 alkyl group” include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, a 2- (methoxy) ethyl group, a 1- (ethoxy) ethyl group, 2 -(Ethoxy) ethyl group etc. are mentioned.
In the present specification, the expression “may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, those The atoms or groups selected from group X may be the same or different.
In the present specification, the expression “which may have one or more atoms or groups selected from group Y” means that when it has two or more atoms or groups selected from group Y, those The atoms or groups selected from group Y may be the same as or different from each other.
In the present specification, the expression “may have one or more atoms or groups selected from group Z” means that when it has two or more atoms or groups selected from group Z, those The atoms or groups selected from group Z may be the same or different from each other.
In the present specification, the expression “may have one or more halogen atoms”, when having two or more halogen atoms, may be the same or different from each other.
In the compound of the present invention, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
In the compound of the present invention, the notation of “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” is selected from group X in which a hydrogen atom bonded to a carbon atom is selected. A linear or branched hydrocarbon group having 1 to 6 carbon atoms, optionally substituted by an atom or group, wherein two or more atoms or groups selected from group X are When it has, the atom or group chosen from those group X may mutually be same or different.
Examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. , Sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, methoxymethyl group, ethoxymethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, tert-butoxy Methyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propoxyethyl group, 2-isopropoxyethyl group, 2-butoxyethyl group, 2-sec-butoxyethyl group, 2-tert-butoxyethyl group, Trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluor Ethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, methylsulfanylethyl group, ethylsulfanylethyl group, methylsulfinylethyl group, methylsulfonylethyl group, 2-hydroxyethyl group, cyclopropylmethyl group, A C1-C6 alkyl group optionally having one or more atoms or groups selected from group X such as 1-methylcyclopropylmethyl group, 2,2-difluorocyclopropylmethyl group; vinyl group, 1-propenyl Group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1-hexenyl group, 1,1 -Having at least one atom or group selected from group X such as difluoroallyl group and pentafluoroallyl group An optionally substituted C2-C6 alkenyl group; and an ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group, 4,4,4-trifluoro-2-butynyl group A C2-C6 alkynyl group which may have one or more atoms or groups selected from the group X such as, and the like, and is selected in the range of the respective designated number of carbon atoms.
In the compound of the present invention, the expression “C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y” indicates that the hydrogen atom bonded to the carbon atom is selected from group Y Represents a cyclic non-aromatic hydrocarbon group having 3 to 6 carbon atoms, optionally substituted by any atom or group having at least two atoms or groups selected from group Y The atoms or groups selected from those groups Y may be the same or different.
Examples of the “C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and 1-cyclohexenyl. Group, 2-cyclohexenyl group, 3-cyclohexenyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2-methoxycyclohexyl group, 3-methoxycyclohexyl group, 4-methoxycyclohexyl group, 1-fluorocyclohexyl group, 2-fluorocyclohexyl group, 3-fluorocyclohexyl group and 4-fluorocyclohexyl group are exemplified.
In the compound of the present invention, the expression “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” is a carbon atom in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a linear or branched hydrocarbon group having a number of 1 to 6, and when it has two or more halogen atoms, these halogen atoms may be the same or different from each other Good.
Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, tert-butyl, pentyl, neopentyl, hexyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoro C1-C6 alkyl group optionally having one or more halogen atoms such as ethyl group, heptafluoropropyl group, heptafluoroisopropyl group; vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl Group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl , A 1-hexenyl group, a 1,1-difluoroallyl group, a C2-C6 alkenyl group optionally having one or more halogen atoms such as a pentafluoroallyl group; and an ethynyl group, a propargyl group, a 2-butynyl group A C2-C6 alkynyl group optionally having one or more halogen atoms such as 3-butynyl group, 1-pentynyl group, 1-hexynyl group, 4,4,4-trifluoro-2-butynyl group, Each of which is selected for each specified number of carbon atoms.
In the compound of the present invention, the expression “phenyl group optionally having one or more atoms or groups selected from group Z” is arbitrarily selected depending on the atom or group selected from group Z in which a hydrogen atom bonded to a carbon atom is selected. A substituted phenyl group is represented, and at this time, when it has two or more atoms or groups selected from group Z, the atoms or groups selected from group Z may be the same as or different from each other.
Examples of the “phenyl group optionally having one or more atoms or groups selected from group Z” include a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, 2, 3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3, 4,5,6-pentafluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, -Trifluoromethylphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-trifluoromethylsulfanylphenyl group, 3-trifluoromethylsulfanylphenyl group, 4 -Trifluoromethylsulfanylphenyl group, 4-methoxycarbonylphenyl group, 4-nitrophenyl group, 4-cyanophenyl group, 4-methylaminophenyl group, 4-dimethylaminophenyl group, 4-methylsulfinylphenyl group, 4- Examples thereof include a methylsulfonylphenyl group, a 4-acetylphenyl group, and a 4-methoxycarbonylphenyl group.
In the compound of the present invention, the “heterocyclic group” represents a heterocyclic compound residue containing at least one nitrogen atom, oxygen atom and sulfur atom in addition to the carbon atom in the ring structure.
In the compounds of the present invention, the 5-membered heterocyclic group means a 5-membered aromatic heterocyclic group or a 5-membered non-aromatic heterocyclic group, and the 6-membered heterocyclic group means a 6-membered aromatic heterocyclic group. Or a 6-membered non-aromatic heterocyclic group is meant.
In the compound of the present invention, the “heterocyclic group” in the “5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” means nitrogen other than carbon atoms in the ring structure. Represents a heterocyclic compound residue containing at least one atom, oxygen atom and sulfur atom. At this time, when it has two or more atoms or groups selected from group Z, an atom selected from group Z Alternatively, the groups may be the same or different from each other. In the compound of the present invention, the “5- or 6-membered heterocyclic group” means a 5- or 6-membered aromatic heterocyclic group or a 5- or 6-membered non-aromatic heterocyclic group.
Examples of the “5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” include pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidine It may have one or more atoms or groups selected from the group Z such as -1-yl group, tetrahydrofuran-2-yl group, piperidyl group, morpholinyl group, thiomorpholinyl group, etc. Aromatic heterocyclic group; and 2-pyrrolyl group, 2-furyl group, 3-furyl group, 5-pyrazolyl group, 4-pyrazolyl group, 1-pyrrolyl group, 1-methyl-2-pyrrolyl group, 2-methylsulfanyl -1-pyrrolyl group, 2-methylsulfinyl-1-pyrrolyl group, 2-methylsulfonyl-1-pyrrolyl group, 2-methylamino-1-pyrrolyl group, 2-dimethylamino-1-pyrrole Group, 5-bromo-2-furyl group, 5-nitro-2-furyl group, 5-cyano-2-furyl group, 5-methoxy-2-furyl group, 5-acetyl-2-furyl group, 5- Methoxycarbonyl-2-furyl group, 2-methyl-3-furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl-3-furyl group, 5-methyl-2-thienyl group, 3- Methyl-2-thienyl group, 1-methyl-3-trifluoromethyl-5-pyrazolyl group, 5-chloro-1,3-dimethyl-4-pyrazolyl group, pyrazol-1-yl group, 3-chloro-pyrazole- 1-yl group, 3-bromopyrazol-1-yl group, 4-chloropyrazol-1-yl group, 4-bromopyrazol-1-yl group, imidazol-1-yl group, 1,2,4-triazole- 1-yl group, 3-chloro- , 2,4-triazol-1-yl group, 1,2,3,4-tetrazol-1-yl group, 1,2,3,5-tetrazol-1-yl group, 2-thienyl group, 3-thienyl Group, 3-trifluoromethyl-1,2,4-triazol-1-yl group, 4-trifluoromethylpyrazol-1-yl group, pyrazinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 2-pyridyl group 3-pyridyl group, 4-pyridyl group, 3-fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 6-fluoro-2-pyridyl group, 2-pyrimidinyl And may have one or more atoms or groups selected from group Z such as a group, 3-chloro-5-trifluoromethylpyridin-2-yl group, and 5-trifluoromethylpyridin-2-yl group. 5 young Alternatively, a 6-membered aromatic heterocyclic group can be mentioned.
Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” in the compound of the present invention include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, Examples thereof include a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.
Examples of the “C2-C6 alkenyloxy group optionally having one or more halogen atoms” in the compound of the present invention include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2-butenyloxy group, Examples include 3-butenyloxy group, 2-pentenyloxy group, 2-hexenyloxy group, 3,3-difluoroallyloxy group, and 3,3-dichloroallyloxy group.
Examples of the “C2-C6 alkynyloxy group optionally having one or more halogen atoms” in the compound of the present invention include a propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, Examples include 2-hexynyloxy group and 4,4,4-trifluoro-2-butynyloxy group.
Examples of the “C1-C6 alkylsulfanyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, and pentyl. Examples thereof include a sulfanyl group, a hexylsulfanyl group, a trifluoromethylsulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, and a pentafluoroethylsulfanyl group.
Examples of the “C1-C6 alkylsulfinyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, and pentyl. Examples thereof include a sulfinyl group, a hexylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, and a pentafluoroethylsulfinyl group.
Examples of the “C1-C6 alkylsulfonyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, and pentyl. Examples include a sulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, and a pentafluoroethylsulfonyl group.
In the compound of the present invention, examples of the C2-C6 alkylcarbonyl group which may have one or more halogen atoms include acetyl group, propionyl group, butyryl group, pentanoyl group, hexanoyl group and trifluoroacetyl group. It is done.
Examples of the “C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms” in the compound of the present invention include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, Examples thereof include a tert-butoxycarbonyl group and a 2,2,2-trifluoroethoxycarbonyl group.
Examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” in the compound of the present invention include a cyclopropyl group, a 2,2-difluorocyclopropyl group, and a 2,2-dichlorocyclopropyl group. 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
Examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a methylamino group, an ethylamino group, a 2,2,2-trifluoroethylamino group, propyl An amino group, an isopropylamino group, and a butylamino group are mentioned.
Examples of the “C2-C8 dialkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a dimethylamino group, a diethylamino group, and a bis (2,2,2-trifluoroethyl) amino group. And a dipropylamino group.
In the compound of the present invention, examples of the “(C1-C6 alkoxy) C1-C6 alkyl group optionally having one or more halogen atoms” include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, Examples include 2- (methoxy) ethyl group, 1- (ethoxy) ethyl group and 2- (ethoxy) ethyl group.
In the compound of the present invention, a “5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). The group may have one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups which may have an atom. ”For example, 2-pyrrolyl group, 2-furyl group, 3-furyl group, 5-pyrazolyl group, 4-pyrazolyl group, 1-pyrrolyl group, 1-methyl-2-pyrrolyl group, 5-bromo-2-furyl group, 5-methoxy-2-furyl group, 2-methyl -3-furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl-3-furyl group, 5-methyl-2-thienyl group, 3-methyl-2-thienyl group, 1-methyl- 3-trifluoromethyl-5 Pyrazolyl group, 5-chloro-1,3-dimethyl-4-pyrazolyl group, pyrazol-1-yl group, 3-chloro-pyrazol-1-yl group, 3-bromopyrazol-1-yl group, 4-chloropyrazole -1-yl group, 4-bromopyrazol-1-yl group, imidazol-1-yl group, 1,2,4-triazol-1-yl group, 3-chloro-1,2,4-triazole-1- Yl group, 1,2,3,4-tetrazol-1-yl group, 1,2,3,5-tetrazol-1-yl group, 2-thienyl group, 3-thienyl group, 3-trifluoromethyl-1 2,4-triazol-1-yl group, 4-trifluoromethylpyrazol-1-yl group, pyrazinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group Group, -Fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 6-fluoro-2-pyridyl group, 2-pyrimidinyl group, 3-chloro-5-trifluoromethylpyridine Examples include 2-yl group and 5-trifluoromethylpyridin-2-yl group.
In the compound of the present invention, “C1-C6 haloalkyl group” is represented by a linear or branched chain having 1 to 6 carbon atoms in which one or more hydrogen atoms bonded to carbon atoms are substituted with halogen atoms. In this case, when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
Examples of the “C1-C6 haloalkyl group” include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, and trichloromethyl. Group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group and heptafluoroisopropyl Groups.
In the present compound, examples of the “C1-C6 perfluoroalkyl group” include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.
In the compound of the present invention, “(C1-C6 alkoxy) C1-C6 alkyl group” is a C1-C6 alkyl group substituted with a C1-C6 alkoxy group. The carbon number is, for example, 2-6. A “(C1-C6 alkoxy) C1-C6 alkyl group” having this carbon number can be represented as a “C2-C6 alkoxyalkyl group”.
Examples of the compound of the present invention include the following compounds.
Formula (1-1)

[Where:
A^1aIs -NR^6a-Represents an oxygen atom or a sulfur atom,
R^1aIs a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms or 1 A C2-C6 alkenyl group which may have one or more halogen atoms, a C2 which may have one or more halogen atoms. -Represents a C6 alkynyl group or a cyclopropyl group,
R^2a, R^4aAnd R^5aAre the same or different and each represents a halogen atom or a hydrogen atom,
R^3aHas a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. A C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms may be present), -OR^20a(Where R^20aRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21a(Where R^21aRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), A cyano group, a nitro group, a halogen atom or a hydrogen atom,
R^6aHas a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. Represents a good C3-C6 alkynyl group,
R^8aIs a C1-C6 alkyl group optionally having one or more halogen atoms, -OR^22a(Where R^22aRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^23a(Where R^23aRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), -SF₅Or a halogen atom,
n represents 0, 1 or 2. ] The compound shown.
Formula (1-2)

[Where:
R^1bRepresents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group,
R^6bRepresents a methyl group or a propargyl group,
R^2b, R^4bAnd R^5bAre the same or different and each represents a halogen atom or a hydrogen atom,
R^3bIs a C1-C6 alkyl group optionally having one or more halogen atoms, -OR^20b(Where R^20bRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21b(Where R^21bRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom,
R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bRepresents a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bRepresents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF₅Or a halogen atom,
n represents 0, 1 or 2. ] The compound shown.
Formula (1-3)

[Where:
R^1bRepresents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group,
R^2b, R^4bAnd R^5bAre the same or different and each represents a halogen atom or a hydrogen atom,
R^3bIs a C1-C6 alkyl group optionally having one or more halogen atoms, -OR^20b(Where R^20bRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21b(Where R^21bRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom,
R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bRepresents a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bRepresents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF₅Or a halogen atom,
n represents 0, 1 or 2. ] The compound shown.
Formula (1-4)

[Where:
R^1bRepresents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group,
R^2b, R^4bAnd R^5bAre the same or different and each represents a halogen atom or a hydrogen atom,
R^3bIs a C1-C6 alkyl group optionally having one or more halogen atoms, -OR^20b(Where R^20bRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21b(Where R^21bRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom,
R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bRepresents a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bRepresents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF₅Or a halogen atom,
n represents 0, 1 or 2. ] The compound shown.
Formula (1-5)

[Where:
R^1bRepresents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group,
R^60bRepresents a hydrogen atom or a (C1-C6 alkoxy) C1-C6 alkyl group optionally having one or more halogen atoms,
R^3bIs a C1-C6 alkyl group optionally having one or more halogen atoms, -OR^20b(Where R^20bRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21b(Where R^21bRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom,
R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bRepresents a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bRepresents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF₅Or a halogen atom,
n represents 0, 1 or 2. ] The compound shown.
In equation (1), A¹-NR⁶A compound that is-.
In equation (1), A¹In which is an oxygen atom.
In equation (1), A¹In which is a sulfur atom.
In equation (1), A¹-NR⁶-, An oxygen atom or a sulfur atom, and R⁶Is a C1-C6 chain hydrocarbon group, (C1-C6 alkoxy) C1-C6 alkyl group, cyclopropyl group or hydrogen atom which may have one or more halogen atoms.
In equation (1), A¹-NR⁶-, An oxygen atom or a sulfur atom, and R⁶Is a C1-C6 chain hydrocarbon group, (C1-C6 alkoxy) C1-C6 alkyl group or cyclopropyl group optionally having one or more halogen atoms.
In equation (1), A¹-NR⁶-, An oxygen atom or a sulfur atom, and R⁶Is a C1-C6 alkyl group.
In equation (1), A¹-NR⁶-, An oxygen atom or a sulfur atom, and R⁶Is a methyl group, ethyl group, propyl group, isopropyl group, methoxymethyl group, ethoxymethyl group or cyclopropyl group.
In equation (1), A¹-NR⁶-, An oxygen atom or a sulfur atom, and R⁶Is a methyl group.
In equation (1), A¹-NR⁶-, An oxygen atom or a sulfur atom, and R⁶In which is a hydrogen atom.
In equation (1), A¹-NR⁶-And R⁶C1-C6 chain hydrocarbon group which may have one or more halogen atoms, (C1-C6 alkoxy) C1-C6 alkyl group or cyclopropyl which may have one or more halogen atoms A compound that is a group.
In equation (1), A¹-NR⁶-And R⁶Is a C1-C6 alkyl group.
In equation (1), A¹-NR⁶-And R⁶Is a methyl group, ethyl group, propyl group, isopropyl group, methoxymethyl group, ethoxymethyl group, cyclopropyl group or hydrogen atom.
In equation (1), A¹-NR⁶-And R⁶Is a methyl group, ethyl group, propyl group, isopropyl group, methoxymethyl group, ethoxymethyl group or cyclopropyl group.
In equation (1), A¹-NR⁶-And R⁶Is a methyl group.
In equation (1), A¹-NR⁶-And R⁶In which is a methyl group or a hydrogen atom.
In equation (1), A¹-NR⁶-And R⁶In which is a hydrogen atom.
In equation (1), A¹-NR⁶-And R⁸In which is a methoxymethyl group, an ethoxymethyl group or a hydrogen atom.
In equation (1), R¹Is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X.
In equation (1), R¹Is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms.
In equation (1), R¹Is a C1-C6 chain hydrocarbon group optionally having one or more fluorine atoms.
In equation (1), R¹Is a C1-C6 chain hydrocarbon group.
In equation (1), R¹Is a C1-C6 alkyl group.
In equation (1), R¹Is a C1-C3 alkyl group.
In equation (1), R¹Is a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y.
In equation (1), R¹Is a C3-C6 alicyclic hydrocarbon group.
In equation (1), R¹In which is a cyclopropyl group, a cyclobutyl group or a cyclopentyl group.
In equation (1), R¹Is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, cyclopropylmethyl, cyclopropyl, trifluoromethyl, 2,2,2-tri A compound that is a fluoroethyl group.
In equation (1), R¹Is a methyl group, an ethyl group, a cyclopropyl group, a cyclopropylmethyl group or a propyl group.
In equation (1), R¹In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
In equation (1), R¹Is an ethyl group or a cyclopropylmethyl group.
In equation (1), R¹Is a methyl group.
In equation (1), R¹Is an ethyl group.
In equation (1), R¹Is a propyl group.
In equation (1), R¹In which is an isopropyl group.
In equation (1), R¹Is a cyclopropyl group.
In equation (1), R¹Is a cyclopropylmethyl group.
In equation (1), R¹In which is a trifluoromethyl group.
In equation (1), R¹Is a 2,2,2-trifluoroethyl group.
In equation (1), R², R³, R⁴And R⁵Are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, -OR¹⁰, -S (O) mR¹⁰, -C (O) R¹⁰, -CO₂R¹⁰, -NR¹⁰R¹¹, Formyl group, cyano group, nitro group, halogen atom or hydrogen atom, R¹⁰And R¹¹Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
In equation (1), R², R³, R⁴And R⁵In which is a hydrogen atom.
In equation (1), R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom, and R³C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR¹⁰, -S (O)_mR¹⁰, -C (O) R¹⁰, -CO₂R¹⁰, -NR¹⁰R¹¹An aldehyde group, a cyano group, a nitro group, a halogen atom or a hydrogen atom, and R¹⁰And R¹¹Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
In equation (1), R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom, and R³C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR¹⁰A halogen atom or a hydrogen atom, R¹⁰Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more halogen atoms.
In equation (1), R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom, and R³Is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom.
In equation (1), R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom, and R³Is a methyl group, ethyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR¹⁰A halogen atom or a hydrogen atom, R¹⁰Is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³Is a methyl group, ethyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³Is a methyl group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³Is an ethyl group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is a trifluoromethyl group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³Is a pentafluoroethyl group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is a heptafluoropropyl group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is a trifluoromethoxy group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is a fluorine atom.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is a chlorine atom.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is a bromine atom.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³In which is an iodine atom.
In equation (1), R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom, and R³, A phenyl group which may have one or more atoms or groups selected from group Z, a 5-membered heterocyclic group which may have one or more atoms or groups selected from group Z, group Z A compound which is a 6-membered heterocyclic group optionally having one or more atoms or groups selected.
In equation (1), R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom, and R³Is a phenyl group optionally having one or more halogen atoms or a C1-C3 alkyl group optionally having one or more halogen atoms, or one or more halogen atoms or one or more halogen atoms. A compound which is a 5- or 6-membered heterocyclic group which may have a C1-C3 alkyl group which may have.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³Is a 2-pyridyl group, 2-pyrimidinyl group, 3-chloro-2-pyridyl group or 3-chloro-5-trifluoromethyl-2-pyridyl group.
In equation (1), R², R⁴And R⁵Is a hydrogen atom and R³Is 2-pyridyl group, 2-pyrimidinyl group, 3-chloro-2-pyridyl group, 3-chloro-5-trifluoromethyl-2-pyridyl group, methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl Group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, fluorine atom, chlorine atom or bromine atom.
In equation (1), R¹Is an ethyl group and R², R³, R⁴And R⁵In which is a hydrogen atom.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³Is a methyl group.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³In which is a trifluoromethyl group.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³Is a pentafluoroethyl group.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³In which is a heptafluoropropyl group.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³Is a 2-pyrimidinyl group.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³In which is a trifluoromethoxy group.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³In which is a chlorine atom.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³In which is a bromine atom.
In equation (1), R¹Is an ethyl group and R², R⁴And R⁵Is a hydrogen atom and R³In which is an iodine atom.
In equation (1), R⁷And R⁸Are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, -OR¹⁰, -S (O)_mR¹⁰, -NR¹⁰R¹¹, -CO₂R¹⁰, -C (O) R¹⁰, A cyano group, a nitro group, a halogen atom or a hydrogen atom, R¹⁰And R¹¹Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
In equation (1), R⁷And R⁸Are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, -OR¹⁰, -S (O)_mR¹⁰A halogen atom or a hydrogen atom, R¹⁰Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more halogen atoms.
In equation (1), R⁷And R⁸Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
In equation (1), R⁷And R⁸Are the same or different, trifluoromethyl group, difluoromethyl group, fluoromethyl group, pentafluoroethyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl A compound which is a group, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom.
In equation (1), R⁸C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR¹¹, -S (O)_mR¹¹Or a halogen atom and R⁷Is a hydrogen atom and R¹¹Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more halogen atoms.
In equation (1), R⁸Is a C1-C6 chain hydrocarbon group having one or more halogen atoms, and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a C1-C6 chain hydrocarbon group having one or more fluorine atoms, and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a C1-C3 alkyl group having one or more fluorine atoms, and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a C1-C3 alkoxy group having one or more fluorine atoms, and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1- having one or more fluorine atoms. A C3 alkylsulfonyl group, R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a halogen atom and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkyl having one or more fluorine atoms A sulfanyl group, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a trifluoromethyl group, pentafluoroethyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, bromine atom or iodine atom, R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a bromine atom and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is an iodine atom and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a trifluoromethyl group and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a pentafluoroethyl group and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a trifluoromethoxy group and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a trifluoromethylsulfanyl group and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a trifluoromethylsulfinyl group and R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a trifluoromethylsulfonyl group, R⁷In which is a hydrogen atom.
In equation (1), R⁸Is a heptafluoroisopropyl group and R⁷In which is a hydrogen atom.
In equation (1), R⁸-SF₅And R⁷In which is a hydrogen atom.
In equation (1), R⁹In which is a hydrogen atom.
A compound in which n is 0 in formula (1).
A compound in which n is 1 in the formula (1).
A compound in which n is 2 in the formula (1).
A compound in which m is 0 in formula (1).
In the formula (1), a compound wherein m is 1.
In the formula (1), a compound wherein m is 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R⁶Is a C1-C6 alkyl group,
R¹Is a C1-C3 alkyl group or cyclopropyl group optionally having one or more fluorine atoms,
R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom,
R³C1-C3 alkyl group optionally having one or more fluorine atoms, 5- or 6-membered heterocyclic group, C1-C3 alkoxy group optionally having one or more fluorine atoms, a halogen atom or A hydrogen atom,
R⁸Is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkyl having one or more fluorine atoms A sulfanyl group, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom,
R⁷Is a hydrogen atom,
R⁹In which is a hydrogen atom.
In equation (1),
A¹-NR⁶−
R⁶Is a C1-C6 alkyl group,
R¹Is a C1-C3 alkyl group or cyclopropyl group optionally having one or more fluorine atoms,
R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom,
R³Is a C1-C3 alkyl group which may have one or more fluorine atoms, a C1-C3 alkoxy group which may have one or more fluorine atoms, a 5- or 6-membered heterocyclic group, a halogen atom or A hydrogen atom,
R⁸Is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkyl having one or more fluorine atoms A sulfanyl group, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom,
R⁷Is a hydrogen atom,
R⁹In which is a hydrogen atom.
In equation (1),
A¹-NR⁶−
R⁶Is a methyl group, an ethyl group, a propyl group or an isopropyl group,
R¹Is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group,
R², R⁴And R⁵Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom,
R³Is methyl, ethyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, trifluoromethoxy, 2-pyrimidinyl, fluorine, chlorine, bromine An atom or a hydrogen atom,
R⁸Is a trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, chlorine atom, bromine atom or An iodine atom,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹Is a sulfur atom,
R¹Is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group,
R², R⁴And R⁵Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom,
R³Is methyl, ethyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, trifluoromethoxy, 2-pyrimidinyl, fluorine, chlorine, bromine An atom or a hydrogen atom,
R⁸Is a trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, chlorine atom, bromine atom or An iodine atom,
R⁷Is a hydrogen atom,
R⁹In which is a hydrogen atom.
In equation (1),
A¹Is an oxygen atom,
R¹Is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group,
R², R⁴And R⁵Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom,
R³Is methyl, ethyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, trifluoromethoxy, 2-pyrimidinyl, fluorine, chlorine, bromine An atom or a hydrogen atom,
R⁸Is a trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, chlorine atom, bromine atom or An iodine atom,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R⁶Is a C1-C6 alkyl group,
R¹Is a C1-C3 alkyl group or cyclopropyl group optionally having one or more fluorine atoms,
R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom,
R³C1-C3 alkyl group optionally having one or more fluorine atoms, 5- or 6-membered heterocyclic group, C1-C3 alkoxy group optionally having one or more fluorine atoms, a halogen atom or A hydrogen atom,
R⁸C1-C3 alkyl group having one or more fluorine atoms, C1-C3 alkylsulfanyl group having one or more fluorine atoms, or C1-C3 having one or more fluorine atoms An alkylsulfonyl group,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound in which n is 0, 1 or 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R¹Is an ethyl group or a cyclopropyl group,
R², R⁴And R⁵Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom,
R³Is a methyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, trifluoromethoxy group, 2-pyrimidinyl group, fluorine atom, chlorine atom, bromine atom or hydrogen atom,
R⁸Is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylsulfanyl group or a trifluoromethylsulfonyl group,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R⁶Is a C1-C6 alkyl group,
R¹Is a C1-C3 alkyl group optionally having one or more fluorine atoms,
R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom,
R³Is a C1-C3 alkyl group which may have one or more fluorine atoms or a hydrogen atom,
R⁸Is a C1-C3 alkyl group having one or more fluorine atoms or a C1-C3 alkylsulfonyl group having one or more fluorine atoms,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R⁶Is a C1-C3 alkyl group,
R¹Is a C1-C3 alkyl group optionally having one or more fluorine atoms,
R²Is a halogen atom or a hydrogen atom,
R³Is a C1-C3 alkyl group which may have one or more fluorine atoms or a hydrogen atom,
R⁴And R⁵Is a hydrogen atom,
R⁸Is a C1-C3 alkyl group having one or more fluorine atoms or a C1-C3 alkylsulfonyl group having one or more fluorine atoms,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R¹Is an ethyl group,
R²Is a chlorine atom or a hydrogen atom,
R³Is a trifluoromethyl group or a hydrogen atom,
R⁴And R⁵Is a hydrogen atom,
R⁸Is a trifluoromethyl group, a pentafluoroethyl group or a trifluoromethylsulfonyl group,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶−
R⁶Is a C1-C6 alkyl group,
R¹Is a C1-C3 alkyl group optionally having one or more fluorine atoms,
R², R⁴And R⁵Are the same or different and are a halogen atom or a hydrogen atom,
R³Is a C1-C3 alkyl group having one or more fluorine atoms or a hydrogen atom,
R⁸Is a C1-C3 alkyl group having one or more fluorine atoms,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶−
R⁶Is a C1-C3 alkyl group,
R¹Is a C1-C3 alkyl group optionally having one or more fluorine atoms,
R²Is a halogen atom or a hydrogen atom,
R³Is a C1-C3 alkyl group having one or more fluorine atoms or a hydrogen atom,
R⁴And R⁵Is a hydrogen atom,
R⁸Is a C1-C3 alkyl group having one or more fluorine atoms,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In equation (1),
A¹-NR⁶-, An oxygen atom or a sulfur atom,
R¹Is an ethyl group,
R²Is a chlorine atom or a hydrogen atom,
R³Is a trifluoromethyl group or a hydrogen atom,
R⁴And R⁵Is a hydrogen atom,
R⁸Is a trifluoromethyl group,
R⁷Is a hydrogen atom,
R⁹Is a hydrogen atom,
A compound wherein n is 2.
In Formula (1-1), A^1a-NR^6aA compound that is-.
In Formula (1-1), A^1aIn which is an oxygen atom.
In Formula (1-1), A^1aIn which is a sulfur atom.
In formula (1-1), R^1aC1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms or 1 And a compound which may have one or more C1-C3 alkyl groups).
In formula (1-1), R^1aIs a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group has one or more halogen atoms or one or more C1-C3 alkyl groups). A compound that is).
In formula (1-1), R^1aIs a C2-C6 alkyl group, a C1-C6 haloalkyl group or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group has one or more halogen atoms or one or more C1-C3 alkyl groups). Compound).
In formula (1-1), R^1aIs a methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group or cyclopropylmethyl group.
In formula (1-1), R^1aIn which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
In formula (1-1), R^1aIs an ethyl group or a cyclopropylmethyl group. In formula (1-1), R^1aIs a C1-C6 alkyl group.
In formula (1-1), R^1aIn which is a C2-C6 alkyl group.
In formula (1-1), R^1aIs a C1-C3 alkyl group.
In formula (1-1), R^1aIs an ethyl group.
In formula (1-1), R^2a, R^4aAnd R^5aAre the same or different and are a halogen atom or a hydrogen atom.
In formula (1-1), R^2a, R^4aAnd R^5aAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-1), R^2a, R^4aAnd R^5aAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-1), R^4aAnd R^5aIs a hydrogen atom and R^2aIn which is a chlorine atom.
In formula (1-1), R^2a, R^4aAnd R^5aAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-1), R^2a, R^4aAnd R^5aAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-1), R^4aAnd R^5aIs a hydrogen atom and R^2aIn which is a chlorine atom.
In formula (1-1), R^2a, R^4aAnd R^5aIn which is a hydrogen atom.
In formula (1-1), R^3aHas a C1-C6 alkyl group which may have one or more halogen atoms, a C2-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. C2-C6 alkynyl group, pyridyl group (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 optionally having a halogen atom) One or more atoms or substituents selected from the group consisting of alkoxy groups may be present.), A pyrimidinyl group (wherein the pyrimidinyl group may have a halogen atom or a halogen atom) It may have one or more atoms or substituents selected from the group consisting of a C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom. R^20a(Where R^20aIs a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21a(Where R^21aIs a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2. ), A compound which is a halogen atom or a hydrogen atom.
In formula (1-1), R^3aC 1 -C 6 alkyl group optionally having one or more halogen atoms, —OR^20a(Where R^20aRepresents a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O)_mR^21a(Where R^21aRepresents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), A pyrimidinyl group, a halogen atom or a hydrogen atom.
In formula (1-1), R^3aIs methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, pentafluoroethyl (-CF₂CF₃), Heptafluoropropyl group (-CF₂CF₂CF₃), -CF (CF₃)₂, -CF₂CF₂CF₂CF₃, A trifluoromethoxy group (-OCF₃), -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, 2-pyridyl group, 5-trifluoromethyl-2-pyridyl group, 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom.
In formula (1-1), R^3aAre methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -CF₂CF₂CF₂CF₃, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, 2-pyrimidinyl group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
In formula (1-1), R^3aTrifluoromethyl group, ethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -OCF₃, 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
In formula (1-1), R^3aIn which is a trifluoromethyl group or a hydrogen atom.
In formula (1-1), R^8aIs a C1-C6 haloalkyl group, -OR^22a(Where R^22aIs a C1-C6 haloalkyl group. ), -S (O)_mR^23a(Where R^23aIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF₅Or a compound which is a halogen atom.
In formula (1-1), R^8aIs a C1-C6 haloalkyl group, -OR^22a(Where R^22aIs a C1-C6 haloalkyl group. ), -S (O)_mR^23a(Where R^23aIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ) Or -SF₅A compound that is
In formula (1-1), R^8aIs a C1-C6 haloalkyl group, -OR^22a(Where R^22aIs a C1-C6 haloalkyl group. ), -S (O)_mR^23a(Where R^23aIs a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
In formula (1-1), R^8aIs a C1-C6 haloalkyl group, -OR^22a(Where R^22aIs a C1-C6 haloalkyl group. ) Or -S (O)_mR^23a(Where R^23aIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
In formula (1-1), R^8aIs a C1-C6 perfluoroalkyl group, -OR^22a(Where R^22aIs a C1-C6 perfluoroalkyl group. ) Or -S (O)_mR^23a(Where R^23aIs a C1-C6 perfluoroalkyl group. ).
In formula (1-1), R^8aIs a trifluoromethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, SF₅, A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
In formula (1-1), R^8aIs a trifluoromethyl group, -CF₂CF₃, -SCF₃Or -S (O)₂CF₃A compound that is
In formula (1-1), R^8aIs a trifluoromethyl group.
In Formula (1-1), A^1a-NR^6a-And R^6aHas a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, or one or more halogen atoms. A compound which is a good C3-C6 alkynyl group.
In Formula (1-1), A^1a-NR^6a-And R^6aIs a methyl group, ethyl group, propyl group, allyl group or propargyl group.
In Formula (1-1), A^1a-NR^6a-And R^6aIn which is a methyl group or a propargyl group.
In formula (1-2), R^1bIn which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
In the formula (1-2), R^1bIs an ethyl group.
In formula (1-2), R^2b, R^4bAnd R^5bAre the same or different and are a halogen atom or a hydrogen atom.
In formula (1-2), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-2), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-2), R^4bAnd R^5bIs a hydrogen atom and R^2bIn which is a chlorine atom.
In formula (1-2), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-2), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-2), R^4bAnd R^5bIs a hydrogen atom and R^2bIn which is a chlorine atom.
In formula (1-2), R^2b, R^4bAnd R^5bIn which is a hydrogen atom.
In formula (1-2), R^3bAre methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -CF₂CF₂CF₂CF₃, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, 2-pyrimidinyl group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
In formula (1-2), R^3bTrifluoromethyl group, ethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -OCF₃, 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
In formula (1-2), R^3bTrifluoromethyl group, ethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -OCF₃, A 2-pyrimidinyl group, a fluorine atom, a bromine atom or a hydrogen atom.
In formula (1-2), R^3bIn which is a trifluoromethyl group or a hydrogen atom.
In formula (1-2), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF₅Or a compound which is a halogen atom.
In formula (1-2), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ) Or -SF₅A compound that is
In formula (1-2), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
In formula (1-2), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
In formula (1-2), R^8bIs a C1-C6 perfluoroalkyl group, -OR^22b(Where R^22bIs a C1-C6 perfluoroalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 perfluoroalkyl group. ).
In formula (1-2), R^8bIs a trifluoromethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, SF₅, A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
In formula (1-2), R^8bIs a trifluoromethyl group, -CF₂CF₃, -SCF₃Or -S (O)₂CF₃A compound that is
In the formula (1-2), a compound wherein n is 2.
In formula (1-3), R^1bIn which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
In the formula (1-3), R^1bIs an ethyl group.
In formula (1-3), R^2b, R^4bAnd R^5bAre the same or different and are a halogen atom or a hydrogen atom.
In formula (1-3), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-3), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-3), R^4bAnd R^5bIs a hydrogen atom and R^2bIn which is a chlorine atom.
In formula (1-3), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-3), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-3), R^4bAnd R^5bIs a hydrogen atom and R^2bIn which is a chlorine atom.
In formula (1-3), R^2b, R^4bAnd R^5bIn which is a hydrogen atom.
In formula (1-3), R^3bAre methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -CF₂CF₂CF₂CF₃, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, 2-pyrimidinyl group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
In formula (1-3), R^3bTrifluoromethyl group, ethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -OCF₃, 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
In formula (1-3), R^3bIn which is a trifluoromethyl group, a chlorine atom or a hydrogen atom.
In formula (1-3), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF₅Or a compound which is a halogen atom.
In formula (1-3), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ) Or -SF₅A compound that is
In formula (1-3), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
In formula (1-3), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
In formula (1-3), R^8bIs a C1-C6 perfluoroalkyl group, -OR^22b(Where R^22bIs a C1-C6 perfluoroalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 perfluoroalkyl group. ).
In formula (1-3), R^8bIs a trifluoromethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, SF₅, A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
In formula (1-3), R^8bIs a trifluoromethyl group, -CF₂CF₃, -SCF₃Or -S (O)₂CF₃A compound that is
In formula (1-3), R^8bIs a trifluoromethyl group, -CF₂CF₃Or -S (O)₂CF₃A compound that is
In the formula (1-3), a compound wherein n is 2.
In formula (1-4), R^1bIn which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
In the formula (1-4), R^1bIs an ethyl group.
In formula (1-4), R^2b, R^4bAnd R^5bAre the same or different and are a halogen atom or a hydrogen atom.
In formula (1-4), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-4), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-4), R^4bAnd R^5bIs a hydrogen atom and R^2bIn which is a chlorine atom.
In formula (1-4), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
In formula (1-4), R^2b, R^4bAnd R^5bAre the same or different and are a chlorine atom or a hydrogen atom.
In formula (1-4), R^4bAnd R^5bIs a hydrogen atom and R^2bIn which is a chlorine atom.
In formula (1-4), R^2b, R^4bAnd R^5bIn which is a hydrogen atom.
In formula (1-4), R^3bAre methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, fluoromethyl, difluoromethyl, trifluoromethyl, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -CF₂CF₂CF₂CF₃, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, A fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom.
In formula (1-4), R^3bTrifluoromethyl group, ethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -OCF₃, 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
In formula (1-4), R^3bIs a trifluoromethyl group.
In formula (1-4), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF₅Or a compound which is a halogen atom.
In formula (1-4), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ) Or -SF₅A compound that is
In formula (1-4), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
In formula (1-4), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
In formula (1-4), R^8bIs a C1-C6 perfluoroalkyl group, -OR^22b(Where R^22bIs a C1-C6 perfluoroalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 perfluoroalkyl group. ).
In formula (1-4), R^8bIs a trifluoromethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, SF₅, A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
In formula (1-4), R^8bIs a trifluoromethyl group, -CF₂CF₃, -SCF₃Or -S (O)₂CF₃A compound that is
In the formula (1-4), a compound wherein n is 2.
In formula (1-5), R^1bIn which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
In formula (1-5), R^1bIs an ethyl group.
In formula (1-5), R^3bAre methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, fluoromethyl, difluoromethyl, trifluoromethyl, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -CF₂CF₂CF₂CF₃, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, A fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom.
In formula (1-5), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF₅Or a compound which is a halogen atom.
In formula (1-5), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ) Or -SF₅A compound that is
In formula (1-5), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ), -S (O)_mR^23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
In formula (1-5), R^8bIs a C1-C6 haloalkyl group, -OR^22b(Where R^22bIs a C1-C6 haloalkyl group. ) Or -S (O)_m ^R23b(Where R^23bIs a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
In formula (1-5), R^8bIs a C1-C6 perfluoroalkyl group, -OR^22b(Where R^22bIs a C1-C6 perfluoroalkyl group. ) Or -S (O)_mR^23b(Where R^23bIs a C1-C6 perfluoroalkyl group. ).
In formula (1-5), R^8bIs a trifluoromethyl group, -CF₂CF₃, -CF₂CF₂CF₃, -CF (CF₃)₂, -OCF₃, -OCF₂CF₃, -SCF₃, -S (O) CF₃, -S (O)₂CF₃, -SCF₂CF₃, -S (O) CF₂CF₃, -S (O)₂CF₂CF₃, SF₅, A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
In formula (1-5), R^60bIs a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group.
Next, a method for producing the compound of the present invention will be described.
The compound of the present invention and the intermediate compound can be produced, for example, by the following (Production Method 1) to (Production Method 15).
(Production method 1)
This invention compound (1-n2) whose n is 2 in Formula (1) can be manufactured by oxidizing an intermediate compound (P1) with an oxidizing agent.

[Wherein the symbols have the same meaning as in formula (1). ]
The oxidation reaction is usually performed in the presence of a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent include m-chloroperbenzoic acid and hydrogen peroxide.
The reaction can be carried out in the presence of a catalyst as necessary. Examples of the catalyst include sodium tungstate.
In the reaction, when n is 0 in the intermediate compound (P1), the oxidant is usually 3 to 10 moles and the catalyst is usually 0.01 to 0. Used in a proportion of 5 moles. When n is 1 in the intermediate compound (P1), the oxidizing agent is usually in a proportion of 2 to 10 mol and the catalyst is usually in a proportion of 0.01 to 0.5 mol with respect to 1 mol of the intermediate compound (P1). Used. When n is 2 in the intermediate compound (P1), the oxidizing agent is usually in a proportion of 1 to 10 mol and the catalyst is usually in a proportion of 0.01 to 0.5 mol with respect to 1 mol of the intermediate compound (P1). Used.
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The compound (1-n2) of the present invention can be isolated by performing post-treatment operations such as concentration. The isolated present compound (1-n2) can be further purified by chromatography, recrystallization and the like.
(Production method 2)
The compound of the present invention in which n is 1 or 2 in formula (1) can be produced by oxidizing the compound of the present invention in which n is 0.

[Wherein the symbols have the same meaning as in formula (1). ]
This invention compound (1-n1) whose n is 1 in Formula (1) can be manufactured by oxidizing this invention compound (1-n0) whose n is 0 with an oxidizing agent.
The oxidation reaction is usually performed in the presence of a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent include sodium periodate and m-chloroperbenzoic acid.
In this reaction, an oxidizing agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the compound (1-n0) of the present invention. Preferably, the oxidizing agent is used in an amount of 1 to 1.2 mol per 1 mol of the compound (1-n0) of the present invention.
The reaction temperature is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The compound (1-n1) of the present invention can be isolated by performing post-treatment operations such as concentration. The isolated compound (1-n1) of the present invention can be further purified by chromatography, recrystallization and the like.
This invention compound (1-n2) whose n is 2 in Formula (1) can be manufactured by oxidizing this invention compound (1-n1) whose n is 1 with an oxidizing agent.
The oxidation reaction is usually performed in the presence of a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent include m-chloroperbenzoic acid and hydrogen peroxide.
In the reaction, the oxidizing agent is usually used at a ratio of 1 to 4 moles with respect to 1 mole of the compound (1-n1) of the present invention. Preferably, the oxidizing agent is used in a ratio of 1 to 2 moles relative to 1 mole of the compound (1-n1) of the present invention.
The reaction temperature is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The compound (1-n2) of the present invention can be isolated by performing post-treatment operations such as concentration. The compound (1-n2) of the present invention can be further purified by chromatography, recrystallization and the like.
In addition, the compound (1-n2) of the present invention in which n is 2 in the formula (1) can be converted into a one-step reaction (one-pot) by oxidizing the compound (1-n0) of the present invention in which n is 0 with an oxidizing agent. Can be manufactured.
The oxidation reaction is usually performed in the presence of a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent include m-chloroperbenzoic acid and hydrogen peroxide.
The reaction can be carried out in the presence of a catalyst as necessary. Examples of the catalyst include sodium tungstate.
In the reaction, with respect to 1 mole of the compound (1-n0) of the present invention, the oxidizing agent is usually used at a ratio of 2 to 5 moles, and the catalyst is usually used at a ratio of 0.01 to 0.5 moles. Preferably, the oxidizing agent is used in a ratio of 2 to 3 moles with respect to 1 mole of the compound (1-n0) of the present invention.
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, and dried. The compound (1-n2) of the present invention can be isolated by post-treatment such as concentration. The isolated present compound (1-n2) can be further purified by chromatography, recrystallization and the like.
(Production method 3)
Intermediate compound (M6-N0) can be produced by oxidizing intermediate compound (M6) with an oxidizing agent. Further, the compound (1-n0) of the present invention in which n is 0 in the formula (1) is produced by reacting the obtained intermediate compound (M6-N0) with the compound (M7) in the presence of a base. be able to.

[Wherein V²Represents a halogen atom, and the other symbols have the same meaning as in formula (1). ]
Intermediate compound (M6-N0) can be produced by oxidizing intermediate compound (M6).
The oxidation reaction is usually performed in the presence of a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent include m-chloroperbenzoic acid and hydrogen peroxide.
The reaction can be carried out in the presence of a catalyst as necessary. Examples of the catalyst include sodium tungstate.
In the reaction, with respect to 1 mol of the intermediate compound (M6), the oxidizing agent is usually used in a proportion of 1 to 10 mol, and the catalyst is usually used in a proportion of 0.01 to 0.5 mol.
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the intermediate compound (M6-N0) can be isolated. The isolated intermediate compound (M6-N0) can be further purified by chromatography, recrystallization and the like.
By reacting the intermediate compound (M6-N0) and the compound (M7) in the presence of a base, the compound (1-n0) of the present invention in which n is 0 in the formula (1) can be produced.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like. Aprotic polar solvents, water and mixtures thereof.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
In the reaction, the compound (M7) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M6-N0).
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (1-n0) of the present invention in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. it can. The isolated compound of the present invention (1-n0) in which n is 0 can be further purified by chromatography, recrystallization and the like.
In the reaction, V²Is preferably a fluorine atom or a chlorine atom.
(Production Method 4)
The intermediate compound (P1) is obtained by reacting the intermediate compound (M1) with the intermediate compound (M2) or the intermediate compound (M18) to produce the intermediate compound (M3). It can be produced by intramolecular condensation (cyclization) of (M3).

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M3) can be produced by reacting intermediate compound (M1) and intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence of a solvent. Examples of the solvent include 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as THF), ethers such as tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Halogenated hydrocarbons such as toluene, benzene, xylene and the like, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, and N, N-dimethylformamide (hereinafter referred to as DMF). ), N-methylpyrrolidone (hereinafter referred to as NMP), 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide (hereinafter referred to as DMSO), and the like, pyridine, quinoline and the like Examples thereof include nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the condensing agent include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as EDCI hydrochloride) and 1,3-dicyclohexylcarbodiimide.
The reaction can be carried out by adding a catalyst as necessary. Examples of the catalyst include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).
In the reaction, with respect to 1 mol of the intermediate compound (M1), the intermediate compound (M2) is usually in a proportion of 0.5 to 2 mol, the condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually in an amount of 0.8. It is used at a ratio of 01 to 1 mol.
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M3) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M3) can be further purified by recrystallization, chromatography or the like.
The intermediate compound (M3) can be produced by reacting the intermediate compound (M1) with the intermediate compound (M18).
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene. Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
The reaction can be carried out by adding a base as necessary. Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. .
In the reaction, the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M1).
The reaction temperature is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M3) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (M3) can be further purified by chromatography, recrystallization and the like.
Intermediate compound (P1) can be produced by intramolecular condensation (cyclization) of intermediate compound (M3).
The reaction is usually performed in the presence of a solvent. Examples of the solvent include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, toluene, and the like. , Aromatic hydrocarbons such as benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone and DMSO Examples thereof include polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
In this reaction, a condensing agent, an acid or a base can be used as necessary.
Examples of the condensing agent include EDCI hydrochloride, a mixture of triphenylphosphine and a base and carbon tetrachloride or carbon tetrabromide, and a mixture of azodiesters such as triphenylphosphine and diethyl azodicarboxylate.
Examples of the acid include sulfonic acids such as paratoluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
Examples of the base include pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU), and 1,5-diazabicyclo [4.3. 0] -5-nonene, nitrogen-containing heterocyclic compounds, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as tripotassium phosphate, potassium carbonate and sodium hydride.
In the reaction, with respect to 1 mol of the intermediate compound (M3), when a condensing agent is used, the ratio of the condensing agent is usually 1 to 5 mol, and when an acid is used, the acid is usually 0.1 mol to 5 mol. When using a mole ratio or base, the base is usually used in a ratio of 1 to 5 moles.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (P1) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (P1) can be further purified by recrystallization, chromatography or the like.
Intermediate compound (P1) can be produced in a one-step reaction (one pot) by reacting intermediate compound (M1) and intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence of a solvent. Examples of the solvent include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, Aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone and DMSO Polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
Examples of the condensing agent include carbodiimides such as EDCI hydrochloride and 1,3-dicyclohexylcarbodiimide.
The reaction can be carried out by adding a catalyst as necessary. Examples of the catalyst include 1-hydroxybenzotriazole.
In the reaction, with respect to 1 mol of the intermediate compound (M1), the intermediate compound (M2) is usually 0.5 to 2 mol, the condensing agent is usually 1 to 5 mol, and the catalyst is usually 0.1. It is used at a ratio of 01 to 1 mol.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (P1) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (P1) can be further purified by recrystallization, chromatography or the like.
The intermediate compound (P1) can be produced in a one-step reaction (one pot) by reacting the intermediate compound (M1) with the intermediate compound (M18).
The reaction is performed in the presence or absence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene. Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
The reaction can be carried out by adding a base as necessary. Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. .
In the reaction, the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M1).
The reaction temperature is usually in the range of 20 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (P1) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (P1) can be further purified by chromatography, recrystallization and the like.
(Production method 5)
An intermediate compound (M14) is reacted with the intermediate compound (M2) or the intermediate compound (M18) to produce an intermediate compound (M14). By reacting with¹Intermediate compound (P1) in which is a sulfur atom (hereinafter referred to as intermediate compound (P20)) can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M14) can be produced by reacting intermediate compound (M9) with intermediate compound (M2).
The reaction is performed in the presence or absence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene. Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and nitrogen-containing aromatic compounds such as pyridine and quinoline And mixtures thereof.
Examples of the condensing agent include EDCI hydrochloride, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, the intermediate compound (M2) is usually used in a proportion of 1 to 3 mol and the condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the intermediate compound (M9).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M14) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (M14) can be further purified by chromatography, recrystallization and the like.
The intermediate compound (M14) can be produced by reacting the intermediate compound (M9) with the intermediate compound (M18).
The reaction is performed in the presence or absence of a solvent. A base can be added as necessary.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene. Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and nitrogen-containing aromatic compounds such as pyridine and quinoline And mixtures thereof.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. .
In the reaction, the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the intermediate compound (M9).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M14) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (M14) can be further purified by chromatography, recrystallization and the like.
Intermediate compound (P20) can be produced by reacting intermediate compound (M14) with a sulfurizing agent.
The reaction is performed in the presence or absence of a solvent.
Examples of the solvent include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, and diglyme, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Aromatic hydrocarbons such as toluene, benzene and xylene, nitriles such as acetonitrile, nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine and quinoline, and mixtures thereof.
Examples of the sulfurizing agent include niline pentasulfide, Lawesson's reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide), and the like.
In the reaction, the sulfurizing agent is usually used in a ratio of 1 mol to 3 mol with respect to 1 mol of the intermediate compound (M14).
The reaction temperature is usually in the range of 0 ° C. to 200 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (P20) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (P20) can be further purified by recrystallization, chromatography or the like.
(Production method 6)
Intermediate compound (P1) can be produced by reacting intermediate compound (M1) and intermediate compound (M4) in the presence of an oxidizing agent.

[Wherein the symbols have the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent include alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether, THF and tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Halogenated hydrocarbons, aromatic hydrocarbons such as toluene, benzene, xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2-imidazolide Non-protic polar solvents such as non-DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
The reaction can be carried out by adding an acid if necessary. Examples of the acid include sulfonic acids such as paratoluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
The reaction can be carried out by adding sulfite as necessary. Examples of the sulfites include sulfites such as sodium bisulfite and sodium disulfite.
Examples of the oxidizing agent include oxygen, copper (II) chloride, and DDQ.
In this reaction, the intermediate compound (M4) is usually in a proportion of 1 to 2 mol, the acid is usually in a proportion of 0.1 to 2 mol, and the sulfite is usually in a proportion of 1 to 1 mol of the intermediate compound (M1). The proportion of 5 moles and the oxidizing agent are usually used in a proportion of 1 to 5 moles.
The reaction temperature is usually in the range of 0 to 200 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (P1) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (P1) can be further purified by recrystallization, chromatography or the like.
(Production method 7)
Intermediate compound (P1-n0) can be produced by reacting intermediate compound (M6) with compound (M7) in the presence of a base.

[Wherein V²Represents a halogen atom, and the other symbols have the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like. Aprotic polar solvents, water and mixtures thereof.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
In the reaction, the compound (M7) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M6).
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, an intermediate compound (P1-n0) in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. it can. The isolated intermediate compound (P1-n0) in which n is 0 can be further purified by chromatography, recrystallization, and the like.
In the reaction, V²Is preferably a fluorine atom or a chlorine atom.
(Production method 8)
The intermediate compound (M20) is reacted with the intermediate compound (M19) or the intermediate compound (M39) to produce the intermediate compound (M20), and then the intramolecular mixture of the obtained intermediate compound (M20) The intermediate compound (M6) can be produced by condensation (cyclization).

[Wherein V²Represents a halogen atom, and the other symbols have the same meaning as in formula (1). ]
Intermediate compound (M20) can be produced according to the method of production method 4, using intermediate compound (M19) instead of intermediate compound (M2).
Intermediate compound (M20) can be produced according to the method of production method 4, using intermediate compound (M39) instead of intermediate compound (M18).
Intermediate compound (M6) can be produced according to the method of production method 4, using intermediate compound (M20) instead of intermediate compound (M3).
Alternatively, the intermediate compound (M6) can be produced in a one-step reaction (one pot) according to the production method 4 using the intermediate compound (M19) instead of the intermediate compound (M2).
Alternatively, the intermediate compound (M39) can be used in place of the intermediate compound (M2), and the intermediate compound (M6) can be produced in a one-step reaction (one pot) according to the production method 4.
In the reaction, V²Is preferably a fluorine atom or a chlorine atom.
(Production method 9)
Intermediate compound (M3) can be produced by reacting intermediate compound (M20) with compound (M7). The intermediate compound (P1-n0) can be produced by intramolecular condensation (cyclization) of the obtained intermediate compound (M3).

[Wherein V²Represents a halogen atom, and the other symbols have the same meaning as in formula (1)]
Intermediate compound (M3) in which n is 0 can be produced according to the method of production method 7, using intermediate compound (M20) instead of intermediate compound (M6).
Intermediate compound (P1-n0) can be produced according to the method of production method 4, using intermediate compound (M3) in which n is 0 instead of intermediate compound (M3).
Further, the intermediate compound (M20) is used instead of the intermediate compound (M6), and the intermediate compound (P1-n0) in which n is 0 is reacted in a one-step reaction (one pot) according to the method of Production Method 7. It can also be manufactured.
In the reaction, V²Is preferably a fluorine atom or a chlorine atom.
(Production method 10)
A¹By reacting intermediate compound (P2) in which is —NH— with compound (M10) in the presence of a base, A¹-NR⁶Intermediate compound (P3) which is'-can be produced.

[Wherein R⁶′ Is R in the formula (1)⁶And L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and other symbols are represented by the formula (1) Represents the same meaning. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like. Aprotic polar solvents and mixtures thereof.
Examples of the base include hydrides of alkali metals and alkaline earth metals such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine.
In the reaction, the compound (M10) is usually used in a proportion of 1 to 5 mol and the base is usually used in a proportion of 1 to 3 mol with respect to 1 mol of the intermediate compound (P2).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (P3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated intermediate compound (P3) can be further purified by chromatography, recrystallization and the like.
(Production method 11)
Intermediate compound (M30) can be nitrated, or intermediate compound (M33) can be reacted with compound (M28) to produce intermediate compound (M30). By reducing the intermediate compound (M30) obtained here, A¹-NR⁶An intermediate compound (M1) that is-can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M30) can be produced by reacting intermediate compound (M33) and compound (M28) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like. Aprotic polar solvents and mixtures thereof.
The reaction can be carried out by adding a base as necessary. Examples of the base include alkali metal hydrides such as sodium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and pyridine, 4-dimethylaminopyridine. And nitrogen-containing aromatic compounds.
In the reaction, with respect to 1 mol of the intermediate compound (M33), the compound (M28) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 0 to 10 mol.
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
Intermediate compound (M30) can be produced by reacting intermediate compound (M29) with a nitrating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
Examples of the nitrating agent include concentrated nitric acid.
In this reaction, the nitrating agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the intermediate compound (M29).
The reaction temperature is usually in the range of -10 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. . The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
A¹-NR⁶The intermediate compound (M1) which is-can be produced by reacting the intermediate compound (M30) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in a hydrogen atmosphere at 1 to 100 atmospheres, usually in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water, and mixtures thereof. Is mentioned.
Examples of the hydrogenation catalyst include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In this reaction, hydrogen is usually used in a proportion of 3 mol to excess and hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the intermediate compound (M30).
The reaction can be performed by adding an acid, a base or the like, if necessary. Examples of the acid include acetic acid and hydrochloric acid, and examples of the base include tertiary amines such as triethylamine, magnesium oxide and the like.
The reaction temperature is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is filtered, extracted with an organic solvent as necessary, and the organic layer is dried and concentrated to perform post-treatment operations such as A.¹-NR⁶The intermediate compound (M1) which is-can be isolated. Isolated A¹-NR⁶The intermediate compound (M1) which is-can be further purified by chromatography, recrystallization and the like.
In addition, the intermediate compound (M30) is prepared by acetylating the intermediate compound (M29) to produce the intermediate compound (M29 ′), and then nitration of the obtained intermediate compound (M29 ′). It can also be produced by producing ') and hydrolyzing the obtained intermediate compound (M30').

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M29 ') can be produced by reacting intermediate compound (M29) with an acylating agent.
The reaction is usually performed in the presence of a solvent or using an acylating agent as a solvent.
Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, DMSO and mixtures thereof.
Examples of the acylating agent used in the reaction include acetic anhydride and paraacetoxynitrobenzene.
The reaction can be carried out by adding a base as necessary. Examples of the base include tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In this reaction, the acetylating agent is usually used in a proportion of 1 mol or more and the base is usually used in a proportion of 0.1 to 10 mol with respect to 1 mol of the intermediate compound (M29).
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (M29 ') can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M29 ') can be further purified by chromatography, recrystallization and the like.
An intermediate compound (M30 ′) is produced by nitration of the intermediate compound (M29 ′) according to the production method 11 using the intermediate compound (M29 ′) instead of the intermediate compound (M29). be able to.
Intermediate compound (M30) can be produced by hydrolyzing intermediate compound (M30 ') in the presence of an acid or a base.
When hydrolyzing with an acid, the reaction is usually carried out using an acid aqueous solution as a solvent.
Examples of the acid include mineral acids such as hydrochloric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and a mixture thereof.
Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and hydrazine.
In the reaction, the base is usually used at a ratio of 1 to 10 mol per 1 mol of the intermediate compound (M30 ′).
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate solution (M30) is isolated by performing post-treatment operations such as acidification of the reaction solution, extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
(Production method 12)
After the intermediate compound (M35) was produced by brominating the intermediate compound (M29), the resulting intermediate compound (M35) was aminated to produce A¹-NR⁶An intermediate compound (M1) that is-can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M35) can be produced by reacting intermediate compound (M29) with a brominating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include water, acetic acid, ethers such as 1,4-dioxane, diethyl ether, and THF, esters such as ethyl acetate and butyl acetate, and halogens such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane. Hydrocarbons, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, DMSO and mixtures thereof.
Examples of the brominating agent include N-bromosuccinimide and bromine.
The brominating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the intermediate compound (M29).
The reaction temperature is usually in the range of −10 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M35) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M35) can be further purified by recrystallization, chromatography or the like.
A¹-NR⁷The intermediate compound (M1) that is − can be produced by reacting the intermediate compound (M35) with an aminating agent in the presence of copper or a copper compound.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include alcohols such as water, methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether and THF, esters such as ethyl acetate and butyl acetate, dichloromethane, chloroform, carbon tetrachloride, 1, Examples thereof include halogenated hydrocarbons such as 2-dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
Examples of the aminating agent include ammonia, aqueous ammonia and lithium amide.
Examples of the copper compound include copper iodide (I), copper oxide (I), copper oxide (II), acetylacetone copper (II), copper acetate (II), copper sulfate (II) and the like.
The reaction can be carried out by adding a ligand as necessary. Examples of the ligand include acetylacetone, salen, and phenanthroline.
The reaction can be carried out by adding a base as necessary. Examples of the base include pyridine, picoline, 2,6-lutidine, DBU, nitrogen-containing heterocyclic compounds such as 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N-ethyldiisopropylamine and the like. Inorganic bases such as tertiary amines, tripotassium phosphate, potassium carbonate, cesium carbonate, sodium hydroxide and the like can be mentioned.
The aminating agent is usually used in a proportion of 1 to 5 mol, and copper or a copper compound is usually used in a proportion of 0.02 to 0.5 mol per 1 mol of the intermediate compound (M35). Is usually used in a proportion of 0.02 to 2 mol, and the base is usually used in a proportion of 1 to 5 mol.
The reaction temperature is usually in the range of 30 to 200 ° C., and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. By collecting the solid obtained by filtration¹-NR⁷The intermediate compound (M1) which is-can be isolated. Isolated A¹-NR⁷The intermediate compound (M1) which is-can be further purified by recrystallization, chromatography or the like.
(Production method 13)
After the intermediate compound (M32) is produced by nitration of the intermediate compound (M31), the intermediate compound (M32) thus obtained is reduced to reduce A in formula (M1).¹Intermediate compound (M1) in which is an oxygen atom can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M32) can be produced according to the method of production method 11 using intermediate compound (M31) instead of intermediate compound (M29).
Substituting the intermediate compound (M32) for the intermediate compound (M30), A¹Intermediate compound (M1) in which is an oxygen atom can be produced.
(Production method 14)
In the formula (M1), an intermediate compound (M34) is produced by reacting the intermediate compound (M33) with a sulfurizing agent, and then the obtained intermediate compound (M34) is reacted with a reducing agent. A¹Intermediate compound (M1) in which is a sulfur atom can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M34) can be produced by reacting intermediate compound (M33) with thiourea in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include alcohols such as methanol and ethanol, water, and a mixture thereof.
Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In this reaction, thiourea is usually used in a proportion of 0.5 to 3 mol and a base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M33).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, an intermediate compound (M34) can be isolated by performing post-treatment operations such as addition of an acid to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. . The isolated intermediate compound (M34) can also be purified by chromatography, recrystallization and the like.
A¹The intermediate compound (M1) in which is a sulfur atom can be produced by reacting the intermediate compound (M34) with a reducing agent.
The reduction reaction can be performed, for example, in the presence of a reducing agent; an acid such as hydrochloric acid or acetic acid; and water.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, DMF, NMP, and DMSO. And aprotic polar solvents such as and mixtures thereof.
Examples of the reducing agent include metal powder such as iron powder and zinc powder, and tin dichloride.
In the reaction, metal powder or tin dichloride is usually used at a ratio of 3 to 10 mol with respect to 1 mol of the intermediate compound (M34).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer.¹The intermediate compound (M1) in which is a sulfur atom can be isolated. Isolated A¹The intermediate compound (M1) in which is a sulfur atom can also be purified by chromatography, recrystallization and the like.
(Production method 15)
R⁸An intermediate compound (P7) in which is a C1-C6 perfluoroalkyl group is R⁸Can be produced by reacting the intermediate compound (P4) in which is a halogen atom with the compound (M11) or the compound (M11 ′) in the presence of copper or a copper compound.

[Wherein V¹Represents a halogen atom, Rf represents a C1-C6 perfluoroalkyl group, and other symbols have the same meanings as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent include aromatic hydrocarbons such as toluene and xylene, aprotic polar solvents such as DMF, NMP, and DMSO, and mixtures thereof.
Examples of the copper compound include copper (I) iodide.
When the compound (M11) is used in the reaction, the compound (M11) is usually used in a proportion of 1 to 10 mol and the copper compound is usually used in a proportion of 0.5 to 10 mol with respect to 1 mol of the intermediate compound (P4). It is done.
The reaction temperature is usually in the range of 100 to 200 ° C. The reaction time is usually in the range of 0.5 to 48 hours.
In the case of using the compound (M11 ′) in the reaction, potassium fluoride may be added. The compound (M11 ′) is usually in a proportion of 1 to 10 mol, copper or copper compound is usually in a proportion of 0.1 to 10 mol, and potassium fluoride is usually in a proportion of 0.1 to 1 mol of the intermediate compound (P4). Used in a proportion of 5 moles.
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 48 hours.
After completion of the reaction, the intermediate compound (P7) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated intermediate compound (P7) can be further purified by chromatography, recrystallization and the like.
In the reaction, V¹As for, a bromine atom and an iodine atom are preferable.
Next, specific examples of the compound of the present invention are shown below.
Formula (1)

R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination of the compounds described in [Table 1] to [Table 14].

(In the above [Table 1] to [Table 14], Me represents a methyl group, Et represents an ethyl group, Pr represents an n-propyl group, iPr represents an isopropyl group, and tBu represents a tert-butyl group. And CycPr represents a cyclopropyl group.)
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a pentafluoroethyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a heptafluoroisopropyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethoxy group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfanyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfinyl group and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹, And n are the combinations described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a trifluoromethylsulfonyl group, R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And compounds in which n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹, And n are the combinations described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹, And n are the combinations described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is a bromine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸Is an iodine atom and R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R², R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a fluorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a fluorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a fluorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a fluorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a chlorine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a chlorine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a chlorine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a chlorine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a bromine atom and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a bromine atom and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a bromine atom and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a bromine atom and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a methyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a methyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a methyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a methyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is an ethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is an ethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is an ethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is an ethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R²Is a trifluoromethyl group and R³, R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁴Is a trifluoromethyl group and R², R³, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R⁵Is a trifluoromethyl group and R², R³, R⁴, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a pentafluoroethyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a heptafluoropropyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a trifluoromethoxy group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 3-chloro-2-pyridyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³Is a 2-pyrimidinyl group and R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
In formula (1), R³-SF₅And R², R⁴, R⁵, R⁷And R⁹Is a hydrogen atom and R⁸-SF₅And R¹, A¹And n is a combination described in [Table 1] to [Table 14].
Examples of pests for which the compounds of the present invention are effective include harmful arthropods and nematodes such as harmful insects and harmful mites. Specific examples of such pests include the following.
Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper such as leafhoppers (Empoascaonukii) Cotton aphids (Aphis gossypii), peach aphids (Myus persicae), radish aphids (Brevicorine brassicae), aphis spiraecola, tulip beetle aphids ( Acrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat leaf aphids (Rhopalosiphum padi), citrus aphids (Toxoptera citricidus), peach beetles, peach beetles, etc. Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorisa chinensis), bark beetle (Eysarcoris parvus), winged beetle (Halyomorpha mista) Whitefly species such as svaporiarum, Tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), Alecananthus spiniferus (Aleurocanthus sphinferus), citri), Ruby Roe beetle (Ceroplastes rubens), Iceria scale insect (Icerya purchasi), Fujino scale insect (Pranococcus kraunhiae), Swan scale scale (Pseudococcus longis) is), scale insects such as Pseudauracapaspis pentagona, bed bugs, bed bugs such as bed bugs (Cimex electrarius), and whales.
Lepidopterous pests: Chilo suppressalis, Sankaiga (
Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Pyralidae such as Shibatsutoga (Pediasia teterrellus), common cutworm ( Spodoptera litura, Spodoptera exigua, Ayuyoto (Pseudaletia separata), Miostra brassicae, Amantisipsilon , Tamanagin'uwaba (Plusia nigrisigna), Trichoplusia spp., Heliothis spp., Noctuidae such Helicoverpa spp such as white butterfly such as cabbage butterfly (Pieris rapae), Adokisofiesu genus, oriental fruit moth (Grapholita molesta), soybean pod borer, Leguminivora glycinivorella (Leguminivora glycinivorella), Azukisayamushiga (Matsumuraeses azukivora ), Apple wolfberry (Adoxophies orana fascita), tea wolfberry (Adoxophys honmai.), Chamonaki (Homona magnanima), midipakkumon makupuri (Archipsfus coprus) Species such as Cydia pomonella, Chanohosaga, Phyllonolycter lingoneella, etc. Stag beetles, Sugas such as Plutella xylostella, cotton moths such as Pectinophora gossypiella potato (Phthromeaea perculella), and white-spotted tigers, Hirokosukoga such as Koiga (Tineola bisselliella).
Thrips of the order Thrips thrips (Frankliniella occidentalis), Thrips parmi, etc.
Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomids, house flies (Musca domestica), house flies (Muscina stabulans), etc., black flies, sphagnum flies, fly flies, leaf fly (Delia platura), tiger flies Guribae (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, fruit flies such as Megaselia spiracularis, Clogmial etc. Et acids, sciaridae acids, blackfly acids, Abu such as gadfly (Tabanus trigonus), keds acids and stable flies such.
Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Azuki beetle (Callosobruchuys chiensis), weevil (Echinocnemus squarius) Weevil such as Anthonymus grandis, Sphenophorus venatus, Tenebrio molitor, Tribolium stachyum Leaf beetles such as Phyllotreta striolata, Colorado potato beetle (Leptinotarsa decemlineata), Japanese pine beetle (Anthrenus verbasci), Harajiro tsuka beetle worms , Shibamushi (Lasiderma serricorne) and other species, Epilacuna (Epilacna vigintioctopuncta) and other species, Lyctus brunneus and pine , Longhorn beetles such as Anoprophora malasacia, click beetles (Agriotes spp.), And the long-horned beetle (Paederus fuscipes).
Pterodoptera: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Red-bellied lion (Oxya yezoensis), Lobster (Oxya japonica), and crickets.
Lepidoptera: Cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mud mines (Xenopsylla cheopeis) and the like.
Anoplura: body louse (Pediculus humanus corporis), head lice (Pediculus humanus humanus), crab louse (Phthirus pubis), Ushijirami (Haematopinus eurysternus), Hitsujijirami (Dalmalinia ovis), Butajirami (Haematopinus suis), Inujirami (Linognathus setosus) and the like.
White-eye pests: sheep lice (Dalmalinia ovis), cattle lice (Dalmalinia bovis), chicken lice (Menopon gallinae), dog lice (Trichodictes canis), cat lice, etc.
Hymenoptera: Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Ants such as Argentine ants (Linepithema humile), wasps such as wasps, scallops, and wasps such as wasp (Athalia rosae) and Japanese bee (Athalia japonica).
Nematodes: rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematode (Globodera rostochiensis), southern nematode crested pea (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus).
Cockroach pests: German cockroach (Blatella germanica), Black cockroach (Periplaneta fuliginosa), Cockroach cockroach (Periplaneta americana), Periplaneta brunat (Brunetella brunet)
Termite pests: Yamato termites (Reticulitermes pertus), termites (Coptothermes formosanus), American termites minor (Incitermites minor), Dikokite termites (Crypt)
otermes domesticus), Taiwan termites (Odontotermes formosanus), Kou Shun termite (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Katan termites (Glyptotermes fuscus), Kodama termites (Glyptotermes kodamai), comb Moto termites ( Glypoptermes kushimensis, White termites (Hodotermopsis japonica), Kushwei termites (Coptothermes guangzhoensis), Amami termites (Reticul) termes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis), Nitobe termites (Pericapritermes nitobei), warrior termites (Sinocapritermes
Mushae) et al.
Mite order pests: Tick spider mites (Tetranychus urticae), Tick spider mites (Tetranychus kanzawai), citrus spider mite (Pananychus citri), mite spider mite (Panthonychus ulmi), prickly mite pistols, citrus urticae Tomato rust mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple rust ticles ndali) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), American dog ticks (Dermentertor variabilis), Yamato ticks (Ixodes ovatus), Schulz ticks (Ixodes persulcatus), Black legged ticks (Ixodes scapularis), American Kiramada (Amblyomma americanum), Boophilus microplus (Boophilus microplus), ticks such as Rhipicephalus sanguineus (Rhipicephalus sanguineus), Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), D. farinae (Dermatophagoides farinae), Dermatophagoides pteronyssinus (Dermatophagoides leopard mites, such as Ptrynyssnus, Cheletus eruditus, Scarlet ticks (Cheeletus malaccensis), Scarlet ticks (Cheeletus moor) ei), claw mites such as Cheyletiella yasguri, mites such as mite mites (Octoectes cynotis), mites mites such as mites, mites such as mites, mite mites such as mite, mite mites such as mites Bacoti, Ornithonysus sylvairum, cucumbers such as Dermanysussus gallinae, tsutsugamushi such as Leptotrombidium akamushi, and cepper hasseltii) spiders such as such.
Lip and leg class: Geuji (Thereuonema hilgendorfi), Tobizukade (Scoopendra subspinepes), etc.
Double leg class: Yakuyasu (Oxidus gracilis), Akadesde (Nedyopus tambanus), etc.
Isopods: Armadillium vulgare, etc.
Gastropoda: Limax marginatus, Limax flavus, etc.
The pest control agent of the present invention contains the compound of the present invention and an inert carrier. The pest control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and a surfactant or other formulation adjuvant is added as necessary. Emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poisonous baits, resin formulations, shampoos, pastes, foams, carbon dioxide formulations, It is formulated into tablets. These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate) Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
Examples of liquid carriers include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons. (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyrate) Nitriles), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).
Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
Other formulation adjuvants include sticking agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.
The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.). The pest control method of the present invention is usually used in the form of the pest control agent of the present invention.
When using the pest control agent of the present invention for pest control in the agricultural field, the application rate is 10,000 m.²The amount of the compound of the present invention is usually 1 to 10,000 g. When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm. Agents, powders, etc. are usually applied as they are.
These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit cultivated soil. You may process to soil.
Also, it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
When using the pest control agent of the present invention to control pests living in the house, the application amount is 1 m when treated on the surface.²The amount of the compound of the present invention per unit is usually 0.01 to 1000 mg. When processing in a space, the processing space is 1 m.³The amount of the present compound per unit is usually 0.01 to 500 mg. When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm. Apply aerosols, smoke, poisonous bait, etc. as they are.
When the harmful arthropod control agent of the present invention is used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals. As a specific method of use, for the purpose of systemic suppression, for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression. In this case, for example, an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag. The amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.
The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American boofish, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: apples, pears, Japanese pears, quince, quince, etc., nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (citrus mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, blue whale, etc.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, Curcas, safflower, Amanasuna, switchgrass, Miscanthus, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.), ornamental plants .
“Crop” includes genetically modified crops.
The pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are shown below.
Active ingredient of insecticide
(1) Organophosphorus compounds
Acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyphos, chlorfenvinphos, chlorpyriphos , Cyanophos (CYAP), diazinon, DCIP (dichroodiisopropyl ether), diclofenthion (ECP), dichlorvos (DDVP), dimethoate (dimeth) ate), dimethylvinphos, disulfoton, EPN, ethion, ethophos, etrimfos, fenthion (MPP), fenitrothion (m) , Formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion, TP nocrotophos, nared (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pirimiphos-methyl (ent), pyridafenidone quinalphos, phentoate (PAP), profenofos, propopafos, prothiophos, prochlorfos, salithion, sulprophos, sulprofos s), temephos, tetrachlorvinphos, terbufos, thiomethon, trichlorphon (DEP), bamidithion, folate, c and fos
(2) Carbamate compounds
Aranicarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfane, cloethocarb, cloethocarb , Phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), methocarb, methomyl, methocarb C, oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), and aldicarb (aldicarb).
(3) Pyrethroid compound
Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyfluthrin (cy). ), Deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinato e), flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praretrin resmethrin), sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, tetramethrin. Phenothrin, cyphenothrin, alpha-cypermethrin, zeta-permethrin, lambda-cyhalothrin, gammacyhalothrin, gammacyhalothrin, gammacyhalothrin (Furamethrin), tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)- (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl -3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- Prop-1-enylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2- Methyl-1-propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3 -(2-Cyano-1-propenyl) cyclopropanecarboxylate.
(4) Nereistoxin compounds
Cartap, bensultap, thiocyclam, monosultap, and bisultap.
(5) Neonicotinoid compounds
Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothidin and clothidin.
(6) Benzoylurea compound
Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and triazuron.
(7) Phenylpyrazole compound
Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
(8) Bt toxin
Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds
Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds
Aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.
(11) Other active insecticide ingredients
Machine oil, nicotine-sulfate; avermectin, bromopropyrate, buprofezin, chlorophenyl, cirphenyl, cirphenyl, cirophaneyl ), DD (1,3-Dichloropropene), emamectin-benzoate, phenazaquin, flupyrazofos, hydroprene, methoprene, methoprene xacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyl, flusidul, pyrosyl triazamate, fulvendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen, calcium, calcium Chlordane, DDT, DSP, fluphenerim, flonicamid, flurifenfen, formatenate, metham-ammonium, metam sodium Methyl bromide, Potassium oleate, Protrifen bute, Spiromesifen, Sulfoxaflor, Sulfur, et alflumione Tetramat (spirotetramat) ), Pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, cyantraniliprole,
Following formula (K)

[In the formula, R¹⁰⁰Represents a chlorine, bromine or trifluoromethyl group, R²⁰⁰Represents a chlorine, bromine or methyl group, R³⁰⁰Represents a chlorine, bromine or cyano group. ]
And a compound represented by
The following formula (L)

[In the formula, R¹⁰⁰⁰Represents chlorine, bromine or iodine. ]
A compound represented by
Active ingredient of acaricide
Acequinosyl, amitraz, benzoximate, bifenaate, phenisobromolate, chinomethionate, BS chlorbenzylate, chlorbenzylate (Clofenetine), cyflumethofen (cyflumetofen), kelsen (dicofol: dicofol), etoxazole (etoxazole), fenbutatin oxide (fenbutatincarb), fenothiocarb (fenothiocarb), fenpyroximate x ), Fluacrylpyrim (fluproxyfen), hexythiazox, propargite (BPPS), polynactin complex (polynatide), pyridabene (pyridenephen) tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cienopyrafen.
Active ingredient of nematicide
DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imicyafos.
Active ingredient of fungicide
Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Dibuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole (triflumizole) raconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bittertanol, bittertanol Azole bactericidal compounds such as flutriafol; cyclic amine bactericidal compounds such as fenpropimorph, tridemorph, fenpropidin; carbendezim, benomylzol, benomylzole benzimidazole bactericidal compounds such as azole and thiophanate-methyl; procymidone; cyprodinil; pyrimethanil; diethofencarb; Iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; fludioxonil; Diphlofluidid; folpet; cresoxime-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin (roxinostrobin); Pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamidon; famoxadon f; famoxadon f; one); zoxamide; ethaboxam; amisulbrom; iprovalicalcarb; (Metrofenone); fluopiran; bixafen; cyflufenamid; proquinazid; isotianil and isothianil (isotianil).
Active ingredient of herbicide
(1) Phenoxy fatty acid herbicidal compound
2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide.
(2) Benzoic acid herbicidal compound
2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compound
Diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, leuthuron, methabendron (Daimuron), and methyl-daimuron.
(4) Triazine herbicidal compound
Atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimetamethrin, promethine, romethrin, promethine, romethrin. And indaziflam.
(5) Bipyridinium herbicidal compound
Paraquat and diquat.
(6) Hydroxybenzonitrile herbicidal compound
Bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compound
Pendimethalin, prodiamine, and trifluralin.
(8) Organic phosphorus herbicidal compound
Amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glucosinate Vialaphos.
(9) Carbamate herbicidal compounds
Di-allate, tri-allate, EPTC, butyrate, bentiocarb, esprocarb, molinate, dimepiperate, swep (Chlorpropham), phenmedifam, phenisopham, pyributicalb, and ashlam.
(10) Acid amide herbicidal compound
Propanil, propyzamide, bromobutide, and etobenzanide.
(11) Chloroacetanilide herbicidal compound
Acetochlor, alachlor, butachlor, dimethenamide, dipachenol, metazachlor, metolachlor, retilachlor, retilachlor And petoxamide.
(12) Diphenyl ether herbicidal compound
Acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxynil, and acloniphen.
(13) Cyclic imide herbicidal compound
Oxadiazone, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, flurochlorac-pentyl, flumioxazine (flumifluaflufen) Ethyl (pyraflufen-ethyl), oxadialgyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfenazone, benzfendizone, benzfendizone Le (saflufenacil).
(14) Pyrazole herbicidal compound
Benzofenap, pyrazolate, pyrazoxifene, topramzone, and pyrasulfotole.
(15) Triketone herbicidal compound
Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compound
Clodinahop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fluodihopbutyl Xylohop-methyl, quizalofop-ethyl, metamihop.
(17) Trione oxime herbicidal compound
Alloxydim-sodium, cetoxydim, butroxydim, clesodim, cloproxidim, cyclohexyloxym, teproloxydim ).
(18) Sulfonylurea herbicidal compound
Chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, tribenuron-methyl trisulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron-methylsulfuronyl-methylsulfate (Amidosulfuron), cinosulfuron (imazosulfuron), rimsulfuron (rimsulfuron), halosulfuron-methyl, prosulfuron (methylsulfuron), methulsulfuron (methylsulfuron) triflusulfuron-methyl), flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azimsulfuron (uronmsulfuron) , Ethoxysulfuron, oxasulfuron, sodium iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methylsulfuron-trisulfuron ), Tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.
(19) Imidazolinone herbicidal compound
Imazametabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, thimapyr, and imazepi.
(20) Sulfonamide herbicidal compound
Flumetslam, metosulam, dicloslam, floraslam, chloranthram-methyl, penoxslam, and pyroxslam pyl
(21) Pyrimidinyloxybenzoic acid herbicidal compound
Pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid, pyriftalid, pyriftalid, pyriftalid, pyriftalid, pyriftalid, pyriftalid, pyriftalid, pyriftalid, pyrifaltid
(22) Other herbicidal compounds
Bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmetirin, p Diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (thiopyr), thiazopyr (thiazopyr), flucarbazone-sodium (propoxycarbazonefenecenafenecename) ), Flufenacet, fentrazamide, fenfenazamide, caffentrol, indanophan, oxadichromefone, fluidate, frenacet, frenacet , Flurtamone, diflufenican, picolinafen, beflubutamide, clomazone, amikacarbazole, pinoxaden den), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl), amino cyclo Pila crawl (aminocyclopyrachlor), type phen carbazone (ipfencarbazone), and Mechiozorin (methiozolin).
Active ingredient of plant growth regulator
Hymexazole, paclobutrazol, uniconazole-P, inabenfide, prohexadione-calcium, abiglycinyl, aviglycine , Abscisic acid, indolebutyric acid, ethiclozate, etephon, cloxyfonac, chlormequat, dichlorprop di, dichlorprop Phosphorus (gibbellellins), prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, calcium peroxide calcide -Chloride) and 4-CPA (4-chlorophenetic acid).
Active ingredient of synergist
Piperonyl butoxide (seperex), sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide (MGK 264), N -Decriimidazole (N-decylimidazole), WARF-anti-resistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH₃I), t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a reference manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples.
First, a manufacture example is shown about manufacture of this invention compound.
Production Example 1 (1)
To a mixture of 3.43 g of 3-chloroanthranilic acid and 20 ml of 1 mol / l hydrochloric acid, 1.38 g of sodium nitrite was added little by little at room temperature and stirred for 10 minutes. The reaction mixture was added dropwise to a separately prepared mixture of 5.65 g of potassium butylxanthate and 20 ml of water at room temperature and stirred for 1 hour. After adding 20 ml of 3N sodium hydroxide aqueous solution and 2.9 ml of diethyl sulfate, the temperature was raised to 100 ° C., and the mixture was stirred for 1 hour while heating under reflux. To the reaction mixture cooled to room temperature, 12 mol / l hydrochloric acid was added dropwise under ice cooling. The precipitated solid was filtered and dried under reduced pressure.
After adding 10 ml of 3N sodium hydroxide aqueous solution, 10 ml of ethanol and 6.86 g of ethyl iodide to the obtained solid, the temperature was raised to 80 ° C. and stirred for 2 hours while heating under reflux. To the reaction mixture cooled to room temperature, 12 mol / l hydrochloric acid was added dropwise under ice cooling, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.79 g of 3-chloro-2-ethylsulfanylbenzoic acid.
3-Chloro-2-ethylsulfanylbenzoic acid

¹ H-NMR (CDCl ₃ ) δ: 8.10-8.05 (1H, m), 7.68 (1H, dd), 7.43 (1H, t), 3.00 (2H, q), 1.26 (3H, t)
Production Example 1 (2)
N ² - methyl-5-trifluoromethyl-pyridine-2,3-diamine 1.14 g, 3- chloro-2-ethylsulfanyl-benzoic acid 1.56 g, a mixture of EDCI hydrochloride 1.02g and pyridine 12 ml, heated to reflux Stir down for 3 hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3-chloro-2-ethylsulfanyl-N- (2-methylamino-5-trifluoromethylpyridin-3-yl) -benzamide.
3-Chloro-2-ethylsulfanyl-N- (2-methylamino-5-trifluoromethylpyridin-3-yl) -benzamide

¹ H-NMR (CDCl ₃ ) δ: 8.39-8.38 (1H, m), 7.80 (1H, brs), 7.70-7.68 (1H, m), 7.67-7 .61 (2H, m), 7.44-7.39 (1H, m), 5.80 (1H, brs), 3.10-3.07 (3H, m), 3.00 (2H, q ), 1.26 (3H, t)
Production Example 1 (3)
A mixture of 3-chloro-2-ethylsulfanyl-N- (2-methylamino-5-trifluoromethylpyridin-3-yl) -benzamide, 3.82 g of tripotassium phosphate and 12 mL of DMSO was added at 150 ° C. for 1 hour and 165 Stir for 2 hours at ° C. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-chloro-2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. 96 g was obtained.
2- (3-Chloro-2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.32-8.30 (1H, m), 7.71 (1H, dd), 7.48-7 .42 (2H, m), 3.73 (3H, s), 2.73 (2H, q), 1.05 (3H, t)
Production Example 1 (4)
To a mixture of 0.72 g of 2- (3-chloro-2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 10 ml of chloroform, -After adding 0.66 g of chloroperbenzoic acid (purity 69-75%), it heated up to room temperature and stirred for 20 minutes. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted twice with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-chloro-2-ethylsulfinylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. 67 g was obtained.
2- (3-Chloro-2-ethylsulfinylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.25 (1H, d), 7.64 (1H, dd), 7.58 (1H, t), 7.39 ( 1H, dd), 3.71 (3H, s), 3.60-3.49 (1H, m), 3.33-3.23 (1H, m), 1.33 (3H, t)
Production Example 1 (5)
A mixture of 0.48 g of 2- (3-chloro-2-ethylsulfinylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 12 ml of acetic acid was heated and stirred at 80 ° C. Then, 6 ml of 30% hydrogen peroxide water was added dropwise thereto. The mixture was heated to 100 ° C. and stirred for 3 hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-chloro-2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 4- 0.13 g of oxide (hereinafter referred to as the present compound 1) was obtained.
Compound 1 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, s), 7.89 (1H, s), 7.85 (1H, dd), 7.73 (1H, t), 7.42 ( 1H, dd), 4.18 (3H, s), 3.59-3.39 (2H, m), 1.34 (3H, t)
Production Example 2 (1)
A mixture of 5,37 g of N ² -methyl-5-trifluoromethylpyridine-2,3-diamine, 6.92 g of 2-fluoro-4-trifluoromethylbenzaldehyde, 3.75 g of sodium hydrogen sulfite and 30 ml of DMF at 150 ° C. Stirred under reflux for hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-fluoro-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 7 .83 g was obtained.
2- (2-Fluoro-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, d), 8.35 (1H, d), 7.91 (1H, t), 7.67 (1H, d), 7.59 ( 1H, d), 3.92 (3H, d) Production Example 2 (2)
To a mixture of 0.35 g of ethyl mercaptan sodium salt (80%) and 9 ml of DMF was added 2- (2-fluoro-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [ 4,5-b] DMF solution of 1.0 g of pyridine was dropped, and then the mixture was warmed to room temperature and stirred at room temperature for 30 minutes. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. 1.10 g was obtained.
2- (2-Ethylsulfanyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.75-8.73 (1H, m), 8.35-8.33 (1H, m), 7.70-7.68 (1H, m), 7 .62-7.56 (2H, m), 3.79 (3H, s), 2.95 (2H, q), 1.28 (3H, t)
Production Example 2 (3)
A mixture of 0.80 g of 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 10 ml of chloroform was cooled with water. After adding 0.67 g of 3-chloroperbenzoic acid (purity 65% or more), it heated up to room temperature and stirred for 30 minutes. Thereafter, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted twice with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. 0.26 g was obtained.
2- (2-Ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.51-8.49 (1H, m), 8.31-8.30 (1H, m), 8 .12-8.09 (1H, m), 7.74 (1H, d), 3.74 (3H, s), 3.48 (2H, q), 1.29 (3H, t)
Production Example 2 (3)
2- (2-ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 1.5 g, 3-chloroperbenzoic acid (purity 65 A mixture of 2.47 g or more and 8 ml of chloroform was refluxed for 8 hours, and 1.65 g of 3-chloroperbenzoic acid (purity 65% or more) was added, and the mixture was further refluxed for 4 hours. A 10% aqueous sodium thiosulfate solution was poured into the cooled reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 2- (2-ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl. 638 mg of 3H-imidazo [4,5-b] pyridine 4-oxide (hereinafter referred to as the present compound 2) was obtained.
Compound 2 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, s), 8.47 (1H, s), 8.12 (1H, d), 7.91 (1H, s), 7.72 ( 1H, d), 4.16 (3H, s), 3.50-3.38 (2H, m), 1.30 (3H, t)
Production Example 3 (1)
A mixture of 1.0 g of N ² -methyl-5-trifluoromethylpyridine-2,3-diamine, 0.96 g of 2-ethylsulfanylbenzaldehyde, 1.80 g of sodium hydrogen sulfite and 10 ml of DMF was heated and stirred at 160 ° C. for 5 hours. . The reaction mixture was ice-cooled, water was added, and the precipitated crystals were collected by filtration, and washed with water and then hexane. The obtained crystals were dried under reduced pressure to obtain 1.09 g of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine.
2- (2-Ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.72-8.70 (1H, m), 8.33-8.31 (1H, m), 7.56-7.49 (2H, m), 7 .47-7.43 (1H, m), 7.39-7.34 (1H, m), 3.77 (3H, s), 2.87 (2H, q), 1.24 (3H, t )
Production Example 3 (2)
2-Chloroperbenzoic acid was added to a mixture of 0.25 g of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 3 ml of chloroform under ice cooling. After adding 0.43 g (purity 65% or more), the mixture was warmed to room temperature and stirred for 1 hour. Chloroform was added to the reaction mixture under ice-cooling, saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with hexane and then methyl-tert-butyl ether to give 2- (2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. 27 g was obtained.
2- (2-Ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine

¹ H-NMR (CDCl ₃ ) δ: 8.75-8.73 (1H, m), 8.29-8.27 (1H, m), 8.25-8.21 (1H, m), 7 .87-7.79 (2H, m), 7.58-7.55 (1H, m), 3.72 (3H, s), 3.42 (2H, q), 1.26 (3H, t )
Production Example 3 (3)
2- (2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 2.44 g, 3-chloroperbenzoic acid (purity 65% or more) 3.04 g , 4,4′-thiobis (6-tert-butyl-m-cresol) 0.05 g and chloroform 20 ml were refluxed for 2 hours, and 1.5 g of 3-chloroperbenzoic acid (purity 65% or more) was added. Thereafter, the mixture was further refluxed for 6 hours. A 10% aqueous sodium thiosulfate solution was poured into the cooled reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 4-oxide (hereinafter, This is referred to as the present compound 3.) 0.87 g was obtained.
Compound 3 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, s), 8.25-8.20 (1H, m), 7.91-7.89 (1H, m), 7.88-7 .82 (2H, m), 7.57-7.52 (1H, m), 4.14 (3H, s), 3.54-3.25 (2H, m), 1.27 (3H, t )
Production Example 4
A mixture of 0.11 g of 2- (2-ethylsulfonylphenyl) -6-trifluoromethyloxazolo [5,4-b] pyridine, 0.69 g of 3-chloroperbenzoic acid (purity 65% or more) and 3 ml of chloroform Refluxed for 5 hours. A 10% aqueous sodium thiosulfate solution was poured into the cooled reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonylphenyl) -6-trifluoromethyloxazolo [5,4-b] pyridine 4-oxide (hereinafter referred to as the present compound 28). .) 0.01 g was obtained.
Compound 28 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, s), 8.27 (1H, dd), 8.04 (1H, dd), 7.97 (1H, s), 7.92- 7.85 (2H, m), 3.76 (2H, q), 1.44 (3H, t).
The compounds described in the above production examples and the compounds produced by the production methods according to the methods described in the above production examples are shown in the table.
The compound represented by Formula (1).

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , R ⁸ , R ⁹ , A ¹ and n in the formula represent the combinations described in the following [Table 15] to [Table 16]. .

Next, the formulation example of this invention compound is shown. The part in a formulation example represents a weight part.
Formulation Example 1
10 parts of any one of the compounds 1 to 28 of the present invention are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate And mix to obtain each emulsion.
Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of the compounds 1 to 28 of the present invention are added and mixed. Get a wettable powder.
Formulation Example 3
1 part of the synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed with 2 parts of any one of the compounds 1 to 28 of the present invention. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
Formulation Example 4
1 part of any one of the compounds 1 to 28 of the present invention is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of PAP and 93.7 parts of fubasami clay are added to this, and the mixture is thoroughly stirred and mixed. Acetone is removed by evaporation to obtain each powder.
Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of any one of the compounds 1 to 28 of the present invention, and 55 parts of water are mixed and wet pulverized. Each flowable agent is obtained by finely pulverizing with.
Formulation Example 6
0.1 part of any one of the compounds 1 to 28 of the present invention is dissolved in 5 parts of xylene and 5 parts of trichloroethane and mixed with 89.9 parts of deodorized kerosene to obtain each oil agent.
Formulation Example 7
10 mg of any one of the compounds 1 to 28 of the present invention is dissolved in 0.5 ml of acetone, and this solution is treated with 5 g of animal solid feed powder (solid feed powder CE-2 for breeding breeding, Nippon Claire Co., Ltd.). And mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.
Formulation Example 8
0.1 part of any one of the compounds 1 to 28 of the present invention, 49.9 parts of neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled and shaken. Finally, an oil aerosol is obtained by mounting the actuator.
Formulation Example 9
Any one of the compounds of the present invention 1-28 0.6 part, BHT (2,6-di-tert-butyl-4-methylphenol) 0.01 part, xylene 5 parts, deodorized kerosene 3.39 parts and emulsifier {Atomos 300 (registered trademark of Atmos Chemical)} 1 part mixed and dissolved and 50 parts distilled water are filled into an aerosol container, and after attaching a valve, 40 parts of propellant (LPG) is added through the valve. Pressurize to obtain an aqueous aerosol.
Formulation Example 10
0.1 g of any one of the compounds 1 to 28 of the present invention is dissolved in 2 ml of propylene glycol and impregnated into a porous ceramic plate having a size of 4.0 × 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke. .
Formulation Example 11
Any 5 parts of the present compounds 1-28 and 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT WD301, manufactured by Sumitomo Chemical Co., Ltd.) are hermetically sealed. A kneader (manufactured by Moriyama Seisakusho) is melt-kneaded, and the obtained kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
Formulation Example 12
5 parts of any of the compounds 1 to 28 of the present invention and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die. A rod-shaped molded body having a length of 15 cm and a diameter of 3 mm is obtained.
Formulation Example 13
100 mg of any of the present compounds 1-28, lactose 68.75 mg, corn starch 237.5 mg, microcrystalline cellulose 43.75 mg, polyvinylpyrrolidone 18.75 mg, sodium carboxymethyl starch 28.75 mg, and magnesium stearate 2. 5 mg is mixed and the resulting mixture is compressed to an appropriate size to obtain tablets.
Formulation Example 14
25 mg of any of the present compounds 1-28, lactose 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is filled into a hard shell gelatin capsule or hydroxypropylmethylcellulose capsule And a capsule is obtained.
Formulation Example 15
Any one of the present compounds 1-28, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, Veegum K (Vanderbilt Co.) 100 mg, flavor 35 mg, and coloring Distilled water is added to 500 mg of the preparation so that the final volume is 100 ml, and mixed to obtain a suspension for oral administration.
Formulation Example 16
Any 5 parts of the compounds 1 to 28 of the present invention are dissolved in 5 parts of polysorbate 85, 3 parts of benzyl alcohol and 30 parts of propylene glycol, and phosphoric acid is added so that the pH of this solution is 6.0 to 6.5. After adding the salt buffer, water is added until the whole becomes 100 parts to obtain a solution for oral administration.
Formulation Example 17
5 parts of aluminum distearate is dispersed by heating in 57 parts of fractionated coconut oil and 3 parts of polysorbate 85. 25 parts of saccharin is dispersed in an oily vehicle obtained by cooling this to room temperature. To this, 10 parts of any one of the compounds 1 to 28 of the present invention are added to obtain a paste preparation for oral administration.
Formulation Example 18
Any 5 parts of the compounds 1 to 28 of the present invention are mixed with 95 parts of limestone powder, and granules for oral administration are obtained using a wet granulation method.
Formulation Example 19
Any 5 parts of the present compounds 1 to 28 are dissolved in 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is mixed therewith to obtain a spot-on solution.
Formulation Example 20
Any 10 parts of the compounds 1 to 28 of the present invention are dissolved in 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed therewith to obtain a pour-on solution.
Formulation Example 21
60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol are added to 0.5 parts of any of the present compounds 1 to 28, and sufficient until a uniform solution is obtained. After stirring and mixing, 19.5 parts of water is added and further stirred and mixed to obtain a shampoo agent of a uniform solution.
Formulation Example 22
0.15 parts of any of the compounds 1 to 28 of the present invention, 95 parts of animal feed, and 4.85 parts of a mixture comprising dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) are sufficiently stirred and mixed. Get a feed premix.
Formulation Example 23
7.2 g of any of the present compounds 1 to 28 and 92.8 g of Phosco S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C., poured into a suppository form, cooled and solidified, and suppository. Get.
Next, the pest control effect of the compound of the present invention is shown by test examples.
Test example 1
Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
On the other hand, about 30 cotton aphids were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups and left for 1 day. The seedlings were sprayed with 20 ml of the test chemical solution.
Six days after spraying, the number of live cotton aphids that parasitized on the leaves of the cucumber was examined, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula have the following meanings.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 1 to 3 of the present invention.
Test example 2
Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
On the other hand, cucumber seedlings planted in plastic cups (second true leaf development stage) were irrigated with 5 ml of the test chemical solution and kept in a greenhouse at 25 ° C. for 7 days. After inoculating 30 cotton aphids (all stages) on the cucumber leaf surface and keeping it in the greenhouse for 6 days, the number of live cotton aphids parasitized on the cucumber leaf was investigated. Asked.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula have the following meanings.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 1 to 3 of the present invention.
Test example 3
The preparation of Compound 3 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the brown planthopper were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthopper infested with rice was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula have the following meanings.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, a control value of 90% or more was shown in the treatment section using the test chemical solution of the present compound 3.
Test example 4
Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
On the other hand, 5 ml of the test drug solution was irrigated to rice seedlings planted in plastic cups (2 weeks after sowing, in the second leaf development stage) and kept in a 25 ° C. greenhouse for 7 days. After releasing 20 3-4 instar larvae of the green planthopper and keeping it in the greenhouse for 6 days, the number of living brown planthoppers parasitized on the rice leaves was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula have the following meanings.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 1 to 3 of the present invention.
Test Example 5
Formulations 2 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
On the other hand, adult white tobacco larvae were released on tomato seedlings (third real leaf development stage) planted in polyethylene cups and allowed to lay eggs for about 72 hours. The tomato seedlings were kept in a greenhouse for 8 days, and the test chemical solution was sprayed at a rate of 20 ml / cup onto the larvae hatched from the delivered eggs, and kept in the greenhouse at 25 ° C. Seven days later, the number of surviving larvae on the tomato leaves was examined, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula have the following meanings.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 2 to 3 of the present invention.
Test Example 6
Formulations 2 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
On the other hand, the test chemical solution was sprayed at a rate of 20 mL / cup on a three-leaf cabbage planted in a polyethylene cup. After the drug solution was dried, the stems and leaves were cut out and placed in a 50 mL cup, 5 of the second-ordered larvae were released, and the lid was capped. After storing at 25 ° C., the number of live insects was counted after 5 days, and the death rate was calculated from the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100
As a result, the mortality rate was 80% or more in the treatment group using the test chemical solutions of the compounds 2 to 3 of the present invention.
Test Example 7
Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration would be 500 ppm to prepare a test spray solution.
On the other hand, apples were planted in plastic cups and grown until the seventh and eighth true leaves developed. The apple was sprayed with the test chemical at a rate of 20 mL / cup. After the chemical solution was dried, 60 first-instar larvae of apple cockerel were released, the bottom was hollowed out, and the plastic cup with filter paper was placed upside down. Seven days later, the number of surviving insects was counted, and the death rate was calculated from the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100
As a result, a mortality rate of 90% or more was shown in the treatment group of the test chemical solutions of the compounds 1 to 3 of the present invention.
Test Example 8
The preparation of Compound 2 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as food. Ten female fly (Musca domestica) females were released into the polyethylene cup and capped. After 24 hours, the life-and-death of the house fly was investigated to determine the death rate.
As a result, in the treatment with Compound 2 of the present invention, a mortality rate of 100% was shown.
Test Example 9
Each formulation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as food. Two adult male German cockroaches (Blattala germanica) are released into the polyethylene cup and covered. After 6 days, investigate the life and death of German cockroaches and determine the death rate.
As a result, a sufficient death rate can be obtained by treatment with the compound of the present invention.
Test Example 10
The preparation of Compound 2 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
0.7 ml of the test chemical solution was added to 100 ml of ion-exchanged water (active ingredient concentration 3.5 ppm). Twenty dead larvae of Culex pipiens parallels were released into the liquid, and the viability was investigated one day later to determine the mortality rate.
As a result, the treatment with Compound 2 of the present invention showed a mortality rate of 91% or more.
Test Example 11
2 mg of the compound of the present invention is weighed into a screw tube (Marume No. 5; 27 × 55 mm), 0.2 mL of acetone is added, and the solution is covered and dissolved. The screw tube is rotated and inverted to coat the chemical solution so that the entire inner wall is uniform. After removing the lid and allowing it to air dry for about 2 hours, 5 groups of non-blood-sucking young ticks (Haemaphysalis longicornis) are released and covered. Two days later, the number of lethals is investigated, and the death rate is calculated using the following formula.
Death rate (%) = 100 x (number of dead ticks / number of test ticks)
As a result, a sufficient death rate can be obtained by treatment with the compound of the present invention.

The compound of the present invention has a control effect against pests and is useful as an active ingredient of a pest control agent.

Claims

Formula (1)

[Where:
A 1 represents —NR 6 —, an oxygen atom or a sulfur atom,
R 1 may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, or one or more atoms or groups selected from group Y. Represents a C3-C6 alicyclic hydrocarbon group,
R 2 , R 3 , R 4 and R 5 are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, -OR 10 , -S (O) m R 10 , -NR 10 R 11 , -CO 2 R 10 , -C (O) R 10 , a cyano group, a nitro group, a halogen atom, -SF 5 or a hydrogen atom,
R 6 may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, and one or more atoms or groups selected from group Y. C3-C6 alicyclic hydrocarbon group, -CO 2 R 10, represents -C (O) R 10 or a hydrogen atom,
R 7 and R 8 are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, -OR 10 , -S (O) m R 10 , -S (O) 2 NR 10 R 11 , -NR 10 R 11 , -NR 10 CO 2 R 11 , -NR 10 C (O) R 11 , -CO 2 R 10 , -C (O) R 10 , A cyano group, a nitro group, a halogen atom, —SF 5 or a hydrogen atom;
R 9 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR 10 , —S (O) m R 10 , —NR 10 R 11 , —CO 2 R 10 , -C (O) R 10 represents a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R 10 and R 11 are the same or different and each represents a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms,
m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, R 7 and R 8 do not simultaneously represent a hydrogen atom, and in —S (O) m R 10 , when m is 1 or 2, R 10 does not represent a hydrogen atom.
Group X: C1-C6 alkoxy group optionally having one or more halogen atoms, C2-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms C2-C6 alkynyloxy group which may have one or more, C1-C6 alkylsulfanyl group which may have one or more halogen atoms, C1-C6 alkylsulfinyl group which may have one or more halogen atoms A C1-C6 alkylsulfonyl group which may have one or more halogen atoms, a C2-C6 alkylcarbonyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkoxycarbonyl group, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group The group consisting of fine-halogen atom.
Group Y: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of a C2-C6 alkenyloxy group optionally having one, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a hydroxy group and a halogen atom.
Group Z: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylsulfanyl group optionally having one or more, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 optionally having one or more halogen atoms Alkylsulfonyl group, C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylamino group optionally having one or more, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, and The group consisting of Toro group. ]
A condensed heterocyclic compound represented by
R 7 and R 8 are the same or different and each may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, —OR 10 , —S (O) m R 10 , halogen atom or hydrogen The condensed heterocyclic compound according to claim 1, which is an atom.
The condensed heterocyclic compound according to claim 1, wherein R 9 is a hydrogen atom.
R 2 , R 4 and R 5 are the same or different and are a hydrogen atom or a halogen atom, and R 3 may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, —OR 10 The condensed heterocyclic compound according to claim 1, which is a halogen atom or a hydrogen atom.
The fused heterocyclic compound according to any one of claims 1 to 4, wherein A 1 is -NR 6- .
A 1 is —NR 6 —, and R 6 may be a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, and may have one or more halogen atoms (C1 The condensed heterocyclic compound according to any one of claims 1 to 4, which is a -C6 alkoxy) C1-C6 alkyl group or a cyclopropyl group.
The fused heterocyclic compound according to any one of claims 1 to 4, wherein A 1 is an oxygen atom.
The condensed heterocyclic compound according to any one of claims 1 to 4, wherein A 1 is a sulfur atom.
A pest control composition comprising the fused heterocyclic compound according to any one of claims 1 to 8 and an inert carrier.
A method for controlling pests, which comprises applying an effective amount of the fused heterocyclic compound according to any one of claims 1 to 8 to pests or habitats of pests.