Complex ring compound and pest arthropod control composition containing the same

Abstract

The present invention provides a compound having an excellent control effect against harmful arthropods. A compound represented by formula (I) or an N-oxide thereof has an excellent control effect against harmful arthropods. (In the formula, Z represents an oxygen atom or the like; G1 represents CR3a or the like; G2 represents CR3b or the like; G3 represents CR3c or the like; G4 represents CR3d or the like; A1 represents CR4a or the like; A2 represents CR4b or the like; A3 represents CR4c or the like; A4 represents CR4d or the like; A5 represents CR4e or the like; R1 represents a C1-C6 chain hydrocarbon group or the like; R2 represents a C1-C6 alkyl group or the like; R3a, R3b, R3c, and R3d are the same or different from one another, and each represents a C1-C6 chain hydrocarbon group or the like; R4a, R4b, R4c, R4d, and R4e are the same or different from one another, and each represents a C1-C6 chain hydrocarbon group or the like; and n represents 0, 1, or 2.)

Description

Technical Field

[0001] This application claims priority and the benefits thereof from Japanese Patent Application No. 2020-165684 filed on September 30, 2020, and Japanese Patent Application No. 2021-102389 filed on June 21, 2021, the entire contents of which are incorporated herein by reference. The present invention relates to a heterocyclic compound and a pest control composition containing the same.

Background Art

[0002] To date, various compounds have been studied for the purpose of controlling harmful arthropods. For example, Patent Document 1 describes that certain compounds have a pest control effect.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present invention is to provide a compound having excellent control efficacy against harmful arthropods.

Means for Solving the Problems

[0005] The present invention is as follows. 〔1〕 Formula (I)

Chemical Formula

[11] to the pest or the habitat of the pest. 〔13〕 A seed or vegetative reproductive organ holding an effective amount of a compound according to any one of [1] to [9] or an N-oxide thereof or an effective amount of the composition according to

[11] . 〔14〕 Formula (II)

Chemical formula

Advantages of the Invention

[0006] According to the present invention, harmful arthropods can be controlled.

Mode for Carrying Out the Invention

[0007] The substituents in the present invention will be described. The halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When the substituent is substituted with two or more halogen atoms or substituents, those halogen atoms or substituents may be the same or different from each other. The notation "CX-CY" in this specification means that the number of carbon atoms is from X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is from 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 1-ethyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group, and a 5-hexenyl group. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-ethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, and a 5-hexynyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. Examples of the alkenyloxy group include a 2-propenyloxy group, a 2-butenyloxy group, and a 5-hexenyloxy group. Examples of the alkynyloxy group include a 2-propynyloxy group, a 2-butynyloxy group, and a 5-hexynyloxy group.

[0008] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Examples of the cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0009] The 3- to 7-membered non-aromatic heterocyclic group represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxadinan ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiadinan ring, a thiomorpholine ring, or a 1,4-thiazepane ring. Examples of the 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E include the groups shown below. [Chemical formula] The 5- or 6-membered aromatic heterocyclic group represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group. The 5-membered aromatic heterocyclic group represents a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group, and the 6-membered aromatic heterocyclic group represents a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group. The 5- or 6-membered heterocyclic group represents a 5- or 6-membered aromatic heterocyclic group or a 5- or 6-membered non-aromatic heterocyclic group. Examples include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a pyrrolidinyl group, an imidazolinyl group, an imidazolidinyl group, a piperidinyl group, a tetrahydropyrimidinyl group, a hexahydropyrimidinyl group, a piperazinyl group, an oxazolidinyl group, an isoxazolidinyl group, a 1,3-oxazinanyl group, a morpholinyl group, a thiazolidinyl group, an isothiazolidinyl group, a 1,3-thiazinanyl group, and a thiomorpholinyl group. Examples of the (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms include a cyclopropylmethyl group, a (2-fluorocyclopropyl)methyl group, a cyclopropyl(fluoro)methyl group, and a (2-fluorocyclopropyl)(fluoro)methyl group. Examples of the phenyl C1-C3 alkyl group {wherein the phenyl moiety in the phenyl C1-C3 alkyl group may be substituted with one or more substituents selected from Group D} include a benzyl group, a 2-fluorobenzyl group, a 4-chlorobenzyl group, a 4-(trifluoromethyl)benzyl group, and a 2-[4-(trifluoromethyl)phenyl]ethyl group. Examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group. Examples of the alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group. Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group. Examples of the alkylamino group include a methylamino group, an ethylamino group, an isopropylamino group, and a hexylamino group. Examples of the dialkylamino group include a dimethylamino group, an ethylmethylamino group, an isopropylmethylamino group, and a dihexylamino group. Examples of the alkylcarbonyl group include an acetyl group, a propanoyl group, a 2-methylpropanoyl group, and a hexanoyl group. Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, and a pentyloxycarbonyl group.

[0010] R 4a 、R 4b 、R 4c 、R 4d 、and R 4e In the case of R 4a 、R 4b 、R 4c 、R 4d 、and R 4e ,the statement “provided that not all of R 1 、A 2 、A 3 、A 4 、and A 5 represent hydrogen atoms” means that the 6-membered ring containing A 4a 、R 4b 、R 4c 、R 4d 、and R 4e (i.e., a phenyl group or a 6-membered aromatic heterocyclic group) has one or more substituents, and it means that at least one of the existing R 1 、R 4a 、R 2 、R 4b 、and R 3 is not a hydrogen atom. For example, in a compound where A 4c is CR 4 ,A 4d is CR 5 ,A 4e is CR 4a 、R 4b 、R 4c 、R 4d, and R 4e Except when all of are hydrogen atoms, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is a nitrogen atom, and A 5 is CR 4e in the compound where is, R 4a , R 4b , R 4c , and R 4e Excluding the case where all of are hydrogen atoms. In other words, in formula (I) or formula (II), formula (I-P)

Chemical formula

[0011] Examples of the N-oxide of the compound represented by formula (I) include compounds represented by the following formula.

Chemical formula

[0012] The compound X and intermediate A of the present invention may have one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, and geometric isomers. The compound X and intermediate A of the present invention include each stereoisomer and a mixture of stereoisomers in any ratio.

[0013] The compound X of the present invention and the compound represented by formula (II) may form acid addition salts. Examples of the acid that forms the acid addition salt include inorganic acids such as hydrogen chloride, phosphoric acid, sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, p-toluenesulfonic acid. The acid addition salt can be obtained by mixing the compound X of the present invention or the compound represented by formula (II) with an acid.

[0014] Examples of the embodiment of the compound N of the present invention include the following compounds.

[0015] 〔Embodiment 1〕In the compound N of the present invention, R 1 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the group W, and when A 5 is CR 4e R 4e and R 1 may together form -NR 45 -CR 41 R 42 -#, R 41 and R 42 are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms or a hydrogen atom, and R 45 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the group X or a hydrogen atom. 〔Embodiment 2〕In the compound N of the present invention, when R 1 is a C1-C6 alkyl group and A 5 is CR 4e R 4e and R 1 may together form -NR 45 -CR 41 R 42 -#, R 41 , R 42 , and R 45 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 〔Embodiment 3〕In the compound N of the present invention, the combination of G 1 , G 2 , G 3 , and G 4 is G1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and the combination; G 1 is a nitrogen atom and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and the combination; G 1 is CR 3a and G 2 is a nitrogen atom and G 3 is CR 3c and G 4 is CR 3d and the combination; or G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom and G 4 is CR 3d and the combination, R 3a , R 3c and R 3d are each a hydrogen atom, R 3b is a C1-C6 alkyl group or a halogen atom which may be substituted with one or more halogen atoms. 〔Aspect 4〕In the compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c and R 3d are each a hydrogen atom, R 3bis a compound that is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect 5〕In the compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group that may be substituted with one or more halogen atoms or a halogen atom. 〔Aspect 6〕In the compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect 7〕In the compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3cand G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and a compound in which R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect 8〕In aspect 1, the combination of G 1 G 2 G 3 and G 4 is such that G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d ; a combination where G 1 is a nitrogen atom, G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d ; a combination where G 1 is CR 3a and G 2 is a nitrogen atom, G 3 is CR 3c and G 4 is CR 3d ; or a combination where G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom, G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and a compound in which R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect 9〕In aspect 2, the combination of G 1 G 2 G 3 and G 4 is such that G1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and the combination; G 1 is a nitrogen atom and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and the combination; G 1 is CR 3a and G 2 is a nitrogen atom and G 3 is CR 3c and G 4 is CR 3d and the combination; or G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom and G 4 is CR 3d and the combination, R 3a , R 3c and R 3d are each a hydrogen atom, R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect 10〕In aspect 1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c and R 3d are each a hydrogen atom, R 3bis a compound wherein the group is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect 11〕In aspect 2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a compound wherein the group is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect 12〕In aspect 1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a compound wherein the group is a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a halogen atom. 〔Aspect 13〕In aspect 2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3cand G 4 is a nitrogen atom or CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect 14〕In aspect 1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect 15〕In aspect 2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. [Aspect 16] In Aspect 1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and a compound in which R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. [Aspect 17] In Aspect 2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and a compound in which R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. [Aspect 18] In the compound N of the present invention, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 19] In the compound N of the present invention, a compound in which Z is an oxygen atom and R 2 is an ethyl group. [Aspect 20] In Aspect 1, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 21] In Aspect 2, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 22] In Aspect 3, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 23] In Aspect 4, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 24] In aspect 5, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 25] In aspect 6, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 26] In aspect 7, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 27] In aspect 8, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 28] In aspect 9, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 29] In aspect 10, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 30] In aspect 11, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 31] In aspect 12, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 32] In aspect 13, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 33] In aspect 14, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 34] In aspect 15, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 35] In aspect 16, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 36] In aspect 17, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect 37] In aspect 1, a compound in which Z is an oxygen atom and R 2 is an ethyl group. [Aspect 38] In aspect 2, a compound in which Z is an oxygen atom and R2 A compound in which R is an ethyl group. 〔Aspect 39〕In aspect 3, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 40〕In aspect 4, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 41〕In aspect 5, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 42〕In aspect 6, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 43〕In aspect 7, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 44〕In aspect 8, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 45〕In aspect 9, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 46〕In aspect 10, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 47〕In aspect 11, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 48〕In aspect 12, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 49〕In aspect 13, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 50〕In aspect 14, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 51〕In aspect 15, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 52〕In aspect 16, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. 〔Aspect 53〕In aspect 17, Z is an oxygen atom, and R 2 A compound in which R is an ethyl group. [Aspect 54] In any of Aspects 1 to 53 or the compound N of the present invention, A 1 , A 2 , A 3 , A 4 , and A 5 's combination, where A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e ; A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , A 5 is CR 4e ; or A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is a nitrogen atom, and the combination where R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is the combination where A 1 , A 2 , A 3 , A 4 , and A 5 are each CH; the combination where A 1 , A 2 , A 3 , and A 4 are each CH and A 5 is a nitrogen atom; the combination where A 1 , A 2 , A 3 , and A 5 are each CH and A 4 is a nitrogen atom; and the combination where A 1 , A 2 , A 4 , and A 5 are each CH and A 3 is a nitrogen atom, are excluded) is a compound. 〔Aspect 55〕In any of Aspects 1 to 53 or the compound N of the present invention, the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is such that A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , and A 5 is CR 4e ; the combination where A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , and A 5 is CR4e a combination that is; or A 1 is CR 4a and A is 2 is CR 4b and A is 3 is CR 4c and A is 4 is CR 4d and A is 5 a combination in which A is a nitrogen atom, R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are each a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is excluded from the combination where A 1 , A 2 , A 3 , A 4 , and A 5 are each CH; A 1 , A 2 , A 3 , and A 4 are each CH and A 5 is a nitrogen atom; A 1 , A 2 , A 3 , and A 5 are each CH and A 4 is a nitrogen atom; and the combination where A 1 , A 2 , A 4 , and A 5 are each CH and A 3 is a nitrogen atom is excluded) is a compound. 〔Aspect 56〕In any one of Aspects 1 to 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR4b and A 3 is CR 4c and A 4 is a nitrogen atom or CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is excluded from the combination where A 1 , A 2 , A 3 , A 4 , and A 5 are each CH; and the combination where A 1 , A 2 , A 3 , and A 5 are each CH and A 4 is a nitrogen atom). 〔Aspect 57〕In any of Aspect 1 to Aspect 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is a nitrogen atom or CR4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are each a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is excluded from the combination in which each of A 1 , A 2 , A 3 , A 4 , and A 5 is CH; and the combination in which each of A 1 , A 2 , A 3 , and A 5 is CH and A 4 is a nitrogen atom). 〔Aspect 58〕In any of Aspects 1 to 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4dis the same or different and is a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms). 〔Aspect 59〕In any of Aspects 1 to 53 or the compound N of the present invention, A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom, and the combination of R 4b , R 4c and R 4d is R 4bis a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 S(O) q R 41 is a cyano group, or a halogen atom, and R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 S(O) q R 41 is a cyano group, a halogen atom or a hydrogen atom; or R 4b is a hydrogen atom and R 4c is a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 S(O) q R 41 is a cyano group, or a halogen atom, and R 4da combination in which it is a hydrogen atom is a compound. 〔Aspect 60〕In any of Aspect 1 to Aspect 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that all of R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms) is a compound. 〔Aspect 61〕In any of Aspect 1 to Aspect 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom, and the combination of R 4b , R 4c and R 4d is R 4bis a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4c and R 4d are the same or different and are a combination of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom; or R 4b is a hydrogen atom, R 4c is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4d is a hydrogen atom is a compound [Aspect 62] In any of Aspect 1 to Aspect 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, R 4e is a halogen atom or a hydrogen atom, and the combination of R 4b , R 4c and R 4d is R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4cis a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4d is a hydrogen atom combination; R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4c is a hydrogen atom, R 4d is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom combination; R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4c and R 4d are each a hydrogen atom combination; or R 4b is a hydrogen atom, R 4c is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, R 4d is a hydrogen atom combination is a compound. [Aspect 63] In any of Aspect 1 to Aspect 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are each a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that not all of R 4b , R 4c , R 4d , and R 4e represent hydrogen atoms). A compound. [Aspect 64] In any of Aspects 1 to 53 or the compound N of the present invention, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are each a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 4e is a hydrogen atom (provided that not all of R 4b , R 4c , R 4d , and R 4e represent hydrogen atoms). A compound.

[0016] [Aspect A1] Formula (IA) [Chemical formula] [In the formula, R 1Ais a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group W, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group U, a phenyl group which may be substituted with one or more substituents selected from group V, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group V, C(O)R 51 , C(O)OR 51 , or C(O)NR 51 R 52 represents, and other symbols represent the meanings as defined in [1]. A compound represented by []. [Aspect A2] In aspect A1, R 1A is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group W. [Aspect A3] In aspect A1, R 1A is a C1-C6 alkyl group. [Aspect A4] In aspect A1, the combination of G 1 , G 2 , G 3 , and G 4 is such that G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , and G 4 is a nitrogen atom or CR 3d ; the combination where G 1 is a nitrogen atom, G 2 is CR 3b , G 3 is CR 3c , and G 4 is CR 3d ; the combination where G 1 is CR 3a , G 2 is a nitrogen atom, G 3 is CR 3c , and G 4 is CR 3d ; or the combination where G 1 is CR 3a , G 2 is CR 3b , and G 3is a nitrogen atom, G 4 is CR 3d is a combination where R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A5〕In aspect A1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be optionally substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect A6〕In aspect A1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A7〕In aspect A1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3cand G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect A8〕In aspect A1, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A9〕In aspect A2, the combination of G 1 G 2 G 3 and G 4 is a combination where G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d ; a combination where G 1 is a nitrogen atom, G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d ; a combination where G 1 is CR 3a and G 2 is a nitrogen atom, G3 is CR 3c and G 4 is CR 3d and the combination where G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom, and G 4 is CR 3d and the combination where R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a halogen atom. 〔Aspect A10〕In aspect A3, the combination of G 1 , G 2 , G 3 , and G 4 is such that G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d ; the combination where G 1 is a nitrogen atom and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d ; the combination where G 1 is CR 3a and G 2 is a nitrogen atom and G 3 is CR 3c and G 4 is CR 3d ; or the combination where G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom and G 4 is CR 3d and R 3a , R 3c , and R 3dis a hydrogen atom, respectively, and R 3b is a compound in which the C1-C6 alkyl group or halogen atom may be substituted with one or more halogen atoms. 〔Aspect A11〕In Aspect A2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are hydrogen atoms, respectively, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect A12〕In Aspect A3, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are hydrogen atoms, respectively, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect A13〕In Aspect A2, G 1 is CR 3a and G 2 is CR 3b and G3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A14〕In aspect A3, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A15〕In aspect A2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be optionally substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect A16〕In aspect A3, G 1 is CR 3a and G 2 is CR 3b and G 3is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect A17〕In aspect A2, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A18〕In aspect A3, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. 〔Aspect A19〕In aspect A1, Z is an oxygen atom, and R 2 is a C1-C6 alkyl group. 〔Aspect A20〕In aspect A1, Z is an oxygen atom, and R 2A compound in which it is an ethyl group. 〔Aspect A21〕In aspect A2, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A22〕In aspect A3, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A23〕In aspect A4, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A24〕In aspect A5, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A25〕In aspect A6, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A26〕In aspect A7, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A27〕In aspect A8, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A28〕In aspect A9, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A29〕In aspect A10, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A30〕In aspect A11, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A31〕In aspect A12, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A32〕In aspect A13, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A33〕In aspect A14, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A34〕In aspect A15, a compound in which Z is an oxygen atom and R 2A compound in which it is a C1-C6 alkyl group. 〔Aspect A35〕In aspect A16, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A36〕In aspect A17, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A37〕In aspect A18, a compound in which Z is an oxygen atom and R 2 is a C1-C6 alkyl group. 〔Aspect A38〕In aspect A2, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A39〕In aspect A3, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A40〕In aspect A4, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A41〕In aspect A5, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A42〕In aspect A6, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A43〕In aspect A7, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A44〕In aspect A8, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A45〕In aspect A9, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A46〕In aspect A10, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A47〕In aspect A11, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A48〕In aspect A12, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A49〕In aspect A13, a compound in which Z is an oxygen atom and R2 A compound in which R is an ethyl group. 〔Aspect A50〕In aspect A14, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A51〕In aspect A15, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A52〕In aspect A16, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A53〕In aspect A17, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A54〕In aspect A18, a compound in which Z is an oxygen atom and R 2 is an ethyl group. 〔Aspect A55〕In any one of aspects A1 to A54, the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is such that A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , and A 5 is CR 4e ; A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , and A 5 is CR 4e ; or A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , and A 5 is a nitrogen atom, where R 4ais a hydrogen atom, and R 4b 、R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 、S(O) q R 41 、a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that the combination of A 1 、A 2 、A 3 、A 4 、and A 5 is the combination where A 1 、A 2 、A 3 、A 4 、and A 5 are each CH; the combination where A 1 、A 2 、A 3 、and A 4 are each CH and A 5 is a nitrogen atom; the combination where A 1 、A 2 、A 3 、and A 5 are each CH and A 4 is a nitrogen atom; and the combination where A 1 、A 2 、A 4 、and A 5 are each CH and A 3 is a nitrogen atom are excluded), a compound. 〔Aspect A56〕In any of Aspect A1 to Aspect A54, A 1 、A 2 、A 3 、A 4 、and A5 The combination of which is A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is a nitrogen atom or CR 4d and A 5 is CR 4e and the combination where A 1 is CR 4a and A 2 is CR 4b and A 3 is a nitrogen atom and A 4 is CR 4d and A 5 is CR 4e and the combination where A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is a nitrogen atom, and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is the combination where A 1 , A 2 , A 3 , A 4 , and A 5 are each CH; A 1 , A 2 , A 3 , and A 4are each CH, and A 5 is a nitrogen atom; A 1 , A 2 , A 3 , and A 5 are each CH, and A 4 is a nitrogen atom; and A 1 , A 2 , A 4 , and A 5 are each CH, and A 3 is a nitrogen atom (excluding the combination). 〔Aspect A57〕In any of Aspect A1 to Aspect A54, A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from Group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is the combination of A 1 , A 2 , A3 , A 4 , and A 5 where each of A is CH; and, A 1 , A 2 , A 3 , and A 5 where each of A is CH and A 4 is a nitrogen atom (excluding the combination where each of A is CH and A [Aspect A58] In any of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is a nitrogen atom or CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is the combination where each of A 1 , A 2 , A 3 , A 4 , and A 5 is CH; and, the combination where each of A 1 , A 2 , A 3 , and A 5 is CH and A 4 is a nitrogen atom is excluded) is a compound. [Aspect A59] In any of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms) is a compound. 〔Aspect A60〕In any of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom, and R 4b , R 4c and R 4d combination is R 4bis a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 、S(O) q R 41 、a cyano group, or a halogen atom, and R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 、S(O) q R 41 、a cyano group, a halogen atom or a hydrogen atom; or R 4b is a hydrogen atom and R 4c is a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 、S(O) q R 41 、a cyano group, or a halogen atom, and R 4da combination in which is a hydrogen atom is a compound. 〔Aspect A61〕In any one of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that not all of R 4b , R 4c , R 4d , and R 4e represent hydrogen atoms), is a compound. 〔Aspect A62〕In any one of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom, and the combination of R 4b , R 4c and R 4d is R 4bA C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c and R 4d are the same or different and are a combination of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom; or R 4b is a hydrogen atom, and R 4c is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4d is a hydrogen atom for the compound. [Aspect A63] In any of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom, and the combination of R 4b , R 4c and R 4d is R 4b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4cis a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4d is a hydrogen atom; R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c is a hydrogen atom, and R 4d is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom; R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c and R 4d are each a hydrogen atom; or R 4b is a hydrogen atom, and R 4c is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4d is a hydrogen atom is a compound. [Aspect A64] In any of Aspects A1 to A54, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR4c where A 4 is CR 4d where A 5 is CR 4e where R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are each a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms), a compound. 〔Aspect A65〕In any of Aspects A1 to A54, A 1 is CR 4a where A 2 is CR 4b where A 3 is CR 4c where A 4 is CR 4d where A 5 is CR 4e where R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are each a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 4e is a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms), a compound.

[0017] 〔Aspect B1〕A compound represented by formula (IB)

Chemical formula

[0018] 〔Aspect B50〕A compound represented by formula (IB)

Chemical formula

[0019] Examples of the compound represented by formula (II) (hereinafter also referred to as intermediate C) include the following compounds.

[0020] 〔Aspect C1〕In intermediate C, the combination of G 1 , G 2 , G 3 , and G 4 is such that G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , and G 4 is a nitrogen atom or CR 3d ; the combination where G 1 is a nitrogen atom, G 2 is CR 3b , G 3 is CR 3c , and G 4 is CR 3d ; the combination where G 1 is CR 3a , G 2 is a nitrogen atom, G 3 is CR 3c , and G 4 is CR 3d ; or G1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom, and G 4 is CR 3d and is a combination where R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a halogen atom. 〔Aspect C2〕In intermediate C, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. 〔Aspect C3〕In intermediate C, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a halogen atom. 〔Aspect C4〕In intermediate C, G 1 is CR3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom. [Aspect C5] In intermediate C, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a halogen atom. [Aspect C6] In intermediate C, Z is an oxygen atom, and R 2 is a C1-C6 alkyl group. [Aspect C7] In intermediate C, Z is an oxygen atom, and R 2 is an ethyl group. [Aspect C8] In aspect C1, Z is an oxygen atom, and R 2 is a C1-C6 alkyl group. [Aspect C9] In aspect C2, Z is an oxygen atom, and R 2 is a C1-C6 alkyl group. [Aspect C10] In aspect C3, Z is an oxygen atom, and R 2 is a C1-C6 alkyl group. [Aspect C11] In aspect C4, a compound wherein Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect C12] In aspect C5, a compound wherein Z is an oxygen atom and R 2 is a C1-C6 alkyl group. [Aspect C13] In aspect C1, a compound wherein Z is an oxygen atom and R 2 is an ethyl group. [Aspect C14] In aspect C2, a compound wherein Z is an oxygen atom and R 2 is an ethyl group. [Aspect C15] In aspect C3, a compound wherein Z is an oxygen atom and R 2 is an ethyl group. [Aspect C16] In aspect C4, a compound wherein Z is an oxygen atom and R 2 is an ethyl group. [Aspect C17] In aspect C5, a compound wherein Z is an oxygen atom and R 2 is an ethyl group. [Aspect C18] In any one of aspects C1 to C17 or intermediate C, the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is such that A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , and A 5 is CR 4e ; A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , and A 5 is CR 4e ; or A 1 is CR 4a , A 2 is CR 4b is CR3 is CR 4c and A 4 is CR 4d and A 5 is a combination where A is a nitrogen atom, R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is excluded from the combination where A 1 , A 2 , A 3 , A 4 , and A 5 are each CH; the combination where A 1 , A 2 , A 3 , and A 4 are each CH and A 5 is a nitrogen atom; the combination where A 1 , A 2 , A 3 , and A 5 are each CH and A 4 is a nitrogen atom; and the combination where A 1 , A 2 , A 4 , and A 5 are each CH and A 3 is a nitrogen atom). A compound. 〔Aspect C19〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 , A 2 , A 3 , A 4 , and A 5 's combination is such that A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e ; A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , A 5 is CR 4e ; or A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is a nitrogen atom, where R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is A 1 , A 2 , A 3 , A4 and A 5 in the combination where each is CH; A 1 A 2 A 3 and A 4 in the combination where each is CH and A 5 is a nitrogen atom; A 1 A 2 A 3 and A 5 in the combination where each is CH and A 4 is a nitrogen atom; and A 1 A 2 A 4 and A 5 in the combination where each is CH and A 3 is a nitrogen atom (excluding the combination). 〔Aspect C20〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is a nitrogen atom or CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from Group J}, OR 44 S(O) q R 41 a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that A1 , A 2 , A 3 , A 4 , and A 5 's combination is A 1 , A 2 , A 3 , A 4 , and A 5 is a combination where each is CH; and, A 1 , A 2 , A 3 , and A 5 are each CH, and A 4 is a nitrogen atom (excluding the combination). [Aspect C21] In any of Aspect C1 - Aspect C17 or Intermediate C, A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1 - C6 alkyl group optionally substituted with one or more halogen atoms, a C1 - C6 alkoxy group optionally substituted with one or more halogen atoms, a C1 - C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that the combination of A 1 , A 2 , A 3 , A 4 , and A 5 is a combination where each is CH; and, A 1 , A 2 , A 3 , A 4 , and A 5 are each CH; and, A 1 , A 2 , A 3 , and A 5 are each CH, and A 4A compound excluding the combination where it is a nitrogen atom. 〔Aspect C22〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from Group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (provided that all of R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms), a compound. 〔Aspect C23〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4eis a C1-C6 alkyl group, a halogen atom, or a hydrogen atom, and R 4b , R 4c and R 4d in combination are R 4b is a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 is a cyano group, or a halogen atom, and R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 is a cyano group, a halogen atom or a hydrogen atom; or R 4b is a hydrogen atom, and R 4cis a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, and the C3-C7 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may be substituted with one or more substituents selected from group J}, OR 44 , S(O) q R 41 , a cyano group, or a halogen atom, and R 4d is a combination in which is a hydrogen atom is a compound of 〔Aspect C24〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 is CR 4a , and A 2 is CR 4b , and A 3 is CR 4c , and A 4 is CR 4d , and A 5 is CR 4e , and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms) is a compound of 〔Aspect C25〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 is CR 4a , and A 2 is CR 4b is CR3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom, and R 4b , R 4c and R 4d in combination are R 4b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c and R 4d are the same or different and are a combination of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom; or R 4b is a hydrogen atom, R 4c is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4d is a hydrogen atom is a compound 〔Aspect C26〕In any of Aspect C1 to Aspect C17 or Intermediate C, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4eis a halogen atom or a hydrogen atom, and R 4b , R 4c and R 4d in combination are R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4d is a hydrogen atom; R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c is a hydrogen atom, and R 4d is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom; R 4b is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4c and R 4d are each a hydrogen atom; or R 4b is a hydrogen atom, and R 4cA C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a cyano group, or a halogen atom, and R 4d is a combination in which it is a hydrogen atom is a compound of. 〔Aspect C27〕In any one of Aspects C1 to C17 or Intermediate C, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 4e is a halogen atom or a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e do not all represent hydrogen atoms) is a compound. 〔Aspect C28〕In any one of Aspects C1 to C17 or Intermediate C, A 1 is CR 4a and A 2 is CR 4b and A 3 is CR 4c and A 4 is CR 4d and A 5 is CR 4e and R 4a is a hydrogen atom, and R 4b , R 4c and R 4dis a C1-C6 alkoxy group which may be the same or different and substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R 4e is a hydrogen atom (provided that R 4b , R 4c , R 4d , and R 4e are not all hydrogen atoms) is a compound.

[0021] Next, the method for producing the compound X of the present invention will be described.

[0022] Production Method 1 The compound represented by the formula (I-b) (hereinafter referred to as compound (I-b)) or the compound represented by the formula (I-c) (hereinafter referred to as compound (I-c)) can be produced by reacting the compound represented by the formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent.

Chemical formula

[0023] First, the method for producing compound (I-b) from compound (I-a) will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of these. Examples of the oxidizing agent used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be added as necessary. Examples of the base used in the reaction include sodium carbonate. When a base is used in the reaction, the base is usually used in a proportion of 0.01 to 1 mole per 1 mole of compound (I-a). Examples of the catalyst used in the reaction include tungstic acid and sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mole per 1 mole of compound (I-a). In the reaction, the oxidizing agent is usually used in a proportion of 1 to 1.2 moles per 1 mole of compound (I-a). 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, water is added to the reaction mixture, and the mixture is extracted with an organic solvent. The organic layer is washed, if necessary, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium hydrogen carbonate). Compound (I-b) can be obtained by drying and concentrating the organic layer.

[0024] Next, a method for producing compound (I-c) from compound (I-b) will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of these. Examples of the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be added as necessary. Examples of the base used in the reaction include sodium carbonate. When a base is used in the reaction, the base is usually used in a proportion of 0.01 to 1 mole per 1 mole of compound (I-b). Examples of the catalyst used in the reaction include sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mole per 1 mole of compound (I-b). In the reaction, the oxidizing agent is usually used in a proportion of 1 to 2 moles per 1 mole of compound (I-b). 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, water is added to the reaction mixture, and the mixture is extracted with an organic solvent. The organic layer is washed, if necessary, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium hydrogen carbonate). The compound (I-c) can be obtained by drying and concentrating this organic layer.

[0025] Also, the compound (I-c) can be produced in a one-pot, one-step reaction by reacting the compound (I-a) with an oxidizing agent. The reaction can be carried out by using the oxidizing agent in a ratio of usually 2 to 5 moles per 1 mole of the compound (I-a), according to the method for producing the compound (I-c) from the compound (I-b).

[0026] Production Method 2 The compound represented by the formula (I-1-A) (hereinafter referred to as the compound (I-1-A)) can be produced by reacting the compound represented by the formula (M1-1-A) (hereinafter referred to as the compound (M1-1-A)) with the compound represented by the formula (M2-1) (hereinafter referred to as the compound (M2-1)) in the presence of a condensing agent. [Chemical formula] [In the formula, R A represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group W, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group U, a phenyl group which may be substituted with one or more substituents selected from group V, or a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group V, and the other symbols have the same meanings as described above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers (hereinafter referred to as ether compounds) such as tetrahydrofuran (hereinafter referred to as THF), methyl tert-butyl ether (hereinafter referred to as MTBE); halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic hydrocarbon compounds); esters such as ethyl acetate and butyl acetate (hereinafter referred to as ester compounds); nitriles; aprotic polar solvents such as N-methylpyrrolidone (hereinafter referred to as NMP), N,N-dimethylformamide (hereinafter referred to as DMF), and dimethyl sulfoxide (hereinafter referred to as DMSO) (hereinafter referred to as aprotic polar solvents); nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine, and quinoline (hereinafter referred to as nitrogen-containing aromatic compounds), and mixtures of two or more of these. Examples of the condensing agent used in the reaction include carbodiimide compounds such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide. A catalyst can be used in the reaction as needed. Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole. When a catalyst is used in the reaction, it is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M1-1-A). A base can be used in the reaction as needed. Examples of the base used in the reaction include organic bases (hereinafter referred to as organic base compounds) such as triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine. When a base is used in the reaction, it is usually used in a proportion of 1 to 2 mol relative to 1 mol of the compound (M1-1-A). In the reaction, relative to 1 mol of the compound (M1-1-A), the compound (M2-1) is usually used in a proportion of 1 to 2 mol, and the condensing agent is usually used in a proportion of 1 to 2 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 12 hours. After the reaction is completed, water is added to the reaction mixture, and extraction is carried out with an organic solvent. The organic layer is dried and concentrated, and other post-treatment operations are performed to obtain the compound (I-1-A). Compound (M2-1) is a commercially available compound or can be produced using known methods.

[0027] Production Method 3 Compound (I-1-A) can also be produced by reacting compound (M1-1-A) with a compound represented by formula (M2-2) (hereinafter referred to as compound (M2-2)).

Chemical formula

[0028] Production Method 4 The compound represented by the formula (I-2-B) (hereinafter referred to as compound (I-2-B)) can be produced by reacting the compound represented by the formula (II) (hereinafter referred to as compound (II)) with the compound represented by the formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of a base.

Chemical formula

[0029] Production Method 5 The compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting the compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2)) with the compound represented by formula (M2-3) (hereinafter referred to as compound (M2-3)).

Chemical formula

[0030] V 1 When V is a fluorine atom, compound (I-1) can be produced by reacting compound (M1-2) with compound (M2-3) in the presence of a base. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of these. Examples of the base used in the reaction include alkali metal carbonates and alkali metal hydrides. In the reaction, compound (M2-3) is usually used in a ratio of 0.8 to 1.2 moles and the base is usually used in a ratio of 1 to 2 moles per 1 mole of compound (M1-2). The reaction temperature is usually in the range of 0 to 200 °C. The reaction time is usually in the range of 0.5 to 24 hours. After the reaction is completed, water is added to the reaction mixture, and extraction is carried out with an organic solvent. Compound (I-1) can be obtained by performing post-treatment operations such as drying and concentrating the organic layer.

[0031] V 1 When V is a chlorine atom, a bromine atom or an iodine atom, compound (I-1) can be produced by reacting compound (M1-2) with compound (M2-3) in the presence of a base and a copper catalyst or a palladium catalyst. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of these. Examples of the base used in the reaction include alkali metal carbonates; phosphates such as trisodium phosphate and tripotassium phosphate; alkali metal hydrides; organic bases; and cyclic amines such as 1,4-diazabicyclo[2,2,2]octane and diazabicycloundecene. Examples of the copper catalyst used in the reaction include copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, etc. When a copper catalyst is used in the reaction, the copper catalyst is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M1-2). Examples of the palladium catalyst used in the reaction include palladium(II) acetate, tris(dibenzylideneacetone)dipalladium(0), etc. When a palladium catalyst is used in the reaction, the palladium catalyst is usually used in a proportion of 0.01 to 0.2 mol relative to 1 mol of the compound (M1-2). A ligand can be used in the reaction as necessary. Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, triphenylphosphine, 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, etc. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M1-2). In the reaction, relative to 1 mol of the compound (M1-2), the compound (M2-3) is usually used in a proportion of 0.8 to 1.2 mol, and the base is usually used in a proportion of 1 to 2 mol. The reaction temperature is usually in the range of 0 to 200 °C. The reaction time is usually in the range of 0.5 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-1). In the compound (M2-3), R 1 is R A or R B The compound can be a commercially available compound or can be produced using a known method.

[0032] Production Method 6 Compound (I-a) can be produced according to the following scheme. [Chemical formula] [In the formula, X a represents a chlorine atom, a bromine atom or an iodine atom, X b represents SR 2 or a hydrogen atom, and the other symbols have the same meanings as described above.]

[0033] First, the process of producing the compound represented by formula (M3-1) (hereinafter referred to as compound (M3-1)) from the compound represented by formula (III-1) (hereinafter referred to as compound (III-1)) (hereinafter referred to as step 6-A) will be described. Compound (M3-1) can be produced by reacting compound (III-1) with a halogenating agent. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, etc. In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 moles per 1 mole of compound (III-1). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is completed, water is added to the reaction mixture, and extraction is carried out with an organic solvent. Compound (M3-1) can be obtained by performing post-treatment operations such as drying and concentrating the organic layer.

[0034] Next, the process of producing compound (I-a) from compound (M3-1) will be described. Compound (I-a) can be produced by reacting compound (M3-1) with the compound represented by formula (R-2) (hereinafter referred to as compound (R-2)) in the presence of a metal catalyst and a base. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of these. Examples of the metal catalyst used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate, etc.; nickel catalysts such as bis(cyclooctadiene)nickel(0), nickel(II) chloride, etc.; and copper catalysts such as copper(I) iodide, copper(I) chloride, etc. Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. A ligand can also be used in the reaction. Examples of the ligand include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, etc. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mol per 1 mol of the compound (M3-1). In the reaction, the compound (R-2) is usually used in a ratio of 1 to 20 mol, the metal catalyst is usually used in a ratio of 0.01 to 0.5 mol, and the base is usually used in a ratio of 0.1 to 5 mol per 1 mol of the compound (M3-1). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to obtain the compound (I-a). The compound (R-2) is known or can be produced according to known methods.

[0035] Next, the process for producing compound (I-a) from compound (III-1) will be described. Compound (I-a) can also be produced by reacting compound (III-1) with a compound represented by formula (R-3) (hereinafter referred to as compound (R-3)) in the presence of a halogenating agent. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of these. Examples of the halogenating agent include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, potassium iodide, and the like. An oxidizing agent can be used in the reaction as needed. Examples of the oxidizing agent used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, DMSO, and the like. When an oxidizing agent is used in the reaction, the oxidizing agent is usually used in a ratio of 1 to 20 moles per 1 mole of compound (III-1). In the reaction, compound (R-3) is usually used in a ratio of 0.5 to 10 moles and the halogenating agent is usually used in a ratio of 0.05 to 10 moles per 1 mole of compound (III-1). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, water is added to the reaction mixture, and extraction is carried out with an organic solvent. Compound (I-a) can be obtained by performing post-treatment operations such as drying and concentrating the organic layer. Compound (R-3) is known or can be produced according to known methods.

[0036] Production Method 7 The compound represented by formula (I-S) (hereinafter referred to as compound (I-S)) can be produced by reacting compound (I-1) with a sulfurizing agent.

Chemical formula

[0037] Production Method 8 The compound represented by the formula (II-S) (hereinafter referred to as compound (II-S)) can be produced by reacting the compound (II-O) with a sulfurizing agent.

Chemical formula

[0038] Production Method 9 The compound represented by the formula (I-3-H) (hereinafter referred to as compound (I-3-H)) can be produced by reacting the compound represented by the formula (M4-1) (hereinafter referred to as compound (M4-1)) with a reducing agent.

Chemical formula

[0039] Production Method 10 The compound represented by the formula (I-3-C) can be produced by reacting the compound (I-3-H) with the compound represented by the formula (R-4) (hereinafter referred to as the compound (R-4)) in the presence of a base.

Chemical formula

[0040] Production Method 11 The N-oxide of the compound represented by the formula (I) can be produced by reacting the compound represented by the formula (I) with an oxidizing agent. The reaction can be carried out, for example, according to the methods described in Production Method 1, U.S. Patent Application Publication No. 2018 / 0009778, or International Publication No. 2016 / 121970.

[0041] The manufacturing method of the production intermediate will be described below.

[0042] Reference Manufacturing Method 1 The compound represented by formula (M1-1-D) (hereinafter referred to as compound (M1-1-D)) can be produced by reacting the compound represented by formula (M1-3) (hereinafter referred to as compound (M1-3)) with the compound represented by formula (R-5) (hereinafter referred to as compound (R-5)) in the presence of a base. [Chemical formula] [In the formula, R D represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group W, or a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group U, and the other symbols represent the same meanings as described above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. In the reaction, compound (R-5) is usually used in a ratio of 1 to 5 moles and the base is usually used in a ratio of 1 to 2 moles per 1 mole of compound (M1-3). 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 the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to obtain compound (M1-1-D).

[0043] Reference Manufacturing Method 2 Compound (M1-1-A) can be produced by reacting the compound represented by formula (M1-2-2) (hereinafter referred to as compound (M1-2-2)) with the compound represented by formula (R-6) (hereinafter referred to as compound (R-6)). [Chemical formula] [wherein, X d represents a fluorine atom or a chlorine atom, and the other symbols represent the same meanings as described above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include aprotic polar solvents, alcohols, and mixtures of two or more of these. A base can be used in the reaction as necessary. Examples of the base used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 5 moles per 1 mole of the compound (M1-2-2). In the reaction, the compound (R-6) is usually used in a proportion of 1 to 100 moles per 1 mole of the compound (M1-2-2). The reaction temperature is usually in the range of 25°C to 200°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to obtain the compound (M1-1-A). The compound (R-6) is a commercially available compound or can be produced using known methods.

[0044] Reference Production Method 3 The compound (M1-3) can be produced by reacting the compound (M1-2-2) with ammonia.

Chemical formula

[0045] Reference Production Method 4 The compound represented by the formula (M1-2b) and the compound represented by the formula (M1-2c) can be produced by reacting the compound represented by the formula (M1-2a) (hereinafter referred to as the compound (M1-2a)) with an oxidizing agent. Further, the compound represented by the formula (M1-2c) can also be produced by reacting the compound represented by the formula (M1-2b) with an oxidizing agent. [Chemical formula] [In the formula, the symbols have the same meanings as described above.] These reactions can be carried out according to Production Method 1.

[0046] Reference Production Method 5 The compound (M1-2a) can be produced according to the following scheme. [Chemical formula] [In the formula, the symbols have the same meanings as described above.]

[0047] These reactions can be carried out according to Production Method 6. The compound represented by formula (M1-4) (hereinafter referred to as compound (M1-4)) is known or can be produced according to the methods described in WO 2015 / 157093, WO 2016 / 109706, Organic & Biomolecular Chemistry, 2017, 15, 4199., and European Journal of Medicinal Chemistry, 2016, 123, 916., etc.

[0048] Reference Production Method 6 Compound (II-O) can be produced by reacting compound (M1-3) with compound (M2-1) or compound (M2-2).

Chemical formula

[0049] Reference Production Method 7 The compound represented by formula (M3-1-A) can be produced by reacting the compound represented by formula (M1-6-A) (hereinafter referred to as compound (M1-6-A)) with compound (M2-1) or compound (M2-2).

Chemical formula

[0050] Reference Production Method 8 The compound represented by formula (M1-6-D) (hereinafter referred to as compound (M1-6-D)) can be produced according to the following scheme.

Chemical formula

[0051] First, a method for producing the compound represented by formula (M1-7) (hereinafter referred to as compound (M1-7)) will be described. Compound (M1-7) can be produced by reacting the compound represented by formula (M1-5) (hereinafter referred to as compound (M1-5)) with ammonia. The reaction can be carried out by using compound (M1-5) instead of compound (M1-2-2) and according to Reference Production Method 3.

[0052] Next, a method for producing compound (M1-6-D) will be described. Compound (M1-6-D) can be produced by reacting compound (M1-7) with compound (R-5) in the presence of a base. The reaction can be carried out by using compound (M1-7) instead of compound (M1-3) and according to Reference Production Method 1.

[0053] Reference Production Method 9 Compound (M1-6-A) can be produced according to the following scheme.

Chemical formula

[0054] First, a method for producing the compound represented by formula (M1-8-A) (hereinafter referred to as compound (M1-8-A)) will be described. Compound (M1-8-A) can be produced by reacting compound (M1-4) with compound (R-6). The reaction can be carried out by using compound (M1-4) instead of compound (M1-2-2) and according to Reference Production Method 2.

[0055] Next, a method for producing compound (M1-6-A) will be described. Compound (M1-6-A) can be produced by reacting compound (M1-8-A) with a halogenating agent. The reaction can be carried out by using compound (M1-8-A) instead of compound (III-1) and following the procedure of Step 6-A in Production Method 6.

[0056] Reference Production Method 10 The compound represented by formula (M3-1-B) (hereinafter referred to as compound (M3-1-B)) can be produced according to the following scheme.

Chemical formula

[0057] First, the production method of the compound represented by formula (M3-2) (hereinafter referred to as compound (M3-2)) will be described. Compound (M3-2) can be produced by reacting compound (M1-7) with compound (M2-1) or compound (M2-2). These reactions can be carried out by using compound (M1-7) instead of compound (M1-1-A) and following Production Method 2 or Production Method 3.

[0058] Next, the production method of compound (M3-1-B) will be described. Compound (M3-1-B) can be produced by reacting compound (M3-2) with compound (R-1) in the presence of a base. The reaction can be carried out by using compound (M3-2) instead of compound (II) and following Production Method 4.

[0059] Reference Production Method 11 The compound represented by formula (III-1-A) (hereinafter referred to as compound (III-1-A)) can be produced according to the following scheme.

Chemical formula

[0060] Reference Production Method 12 The compound represented by formula (III-1-B) (hereinafter referred to as compound (III-1-B)) can be produced according to the following scheme.

Chemical formula

[0061] First, the production method of the compound represented by formula (III-2-B) (hereinafter referred to as compound (III-2-B)) will be described. Compound (III-2-B) can be produced by reacting the compound represented by formula (M1-9) (hereinafter referred to as compound (M1-9)) with compound (M2-1) or compound (M2-2). These reactions can be carried out according to Production Method 2 or Production Method 3 using compound (M1-9) instead of compound (M1-1-A).

[0062] Next, the production method of compound (III-1-B) will be described. Compound (III-1-B) can be produced by reacting compound (III-2-B) with compound (R-1) in the presence of a base. The reaction can be carried out according to Production Method 4 using compound (III-2-B) instead of compound (II).

[0063] Reference Production Method 13 Compound (M1-9) can be produced by reacting compound (M1-4) with ammonia.

Chemical formula

[0064] Reference Production Method 14 The compound represented by formula (III-1-P) (hereinafter referred to as compound (III-1-P)) can be produced by reacting the compound represented by formula (M2-3-P) (hereinafter referred to as compound (M2-3-P)) with compound (M1-4).

Chemical formula

[0065] Reference Production Method 15 Compound (M4-1) can be produced according to the following scheme.

Chemical formula

[0066] First, the production method of the compound represented by formula (M5) (hereinafter referred to as compound (M5)) will be described. Compound (M5) can be produced by reacting the compound represented by formula (M6) (hereinafter referred to as compound (M6)) with compound (M1-3). The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. A base may be used in the reaction as necessary. Examples of the base include organic bases. When a base is used in the reaction, the base is usually used in a ratio of 1 to 5 moles per 1 mole of compound (M6). For the reaction, compound (M1-3) is usually used in a ratio of 1 to 5 moles per 1 mole of compound (M6). The reaction temperature is usually in the range of 0°C to 150°C. The reaction time is usually in the range of 0.5 to 12 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 concentrating the organic layer are performed to obtain compound (M5). Compound (M6) can be produced, for example, according to the method described in Journal of Biological Chemistry, 2016, 291, 14146.

[0067] Next, a method for producing compound (M4-1) from compound (M5) will be described. Compound (M4-1) can be produced by reacting compound (M5) with a compound represented by formula (R-7) (hereinafter referred to as compound (R-7)). The reaction is usually carried out in a solvent or in the absence of a solvent. Examples of the solvent include ethers, aromatic hydrocarbons, halogenated hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. For the reaction, compound (R-7) is usually used in a ratio of 1 to 50 moles per 1 mole of compound (M5). For the reaction, an acid or a base may be used as necessary. Examples of the acid used in the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid. When an acid is used in the reaction, the acid is usually used in a ratio of 0.01 to 5 moles per 1 mole of compound (M5). Examples of the base used in the reaction include organic bases. When a base is used in the reaction, the base is usually used in a ratio of 1 to 5 moles per 1 mole of compound (M5). The reaction temperature is usually in the range of 0°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours. After completion of the reaction, water is added to the reaction mixture, followed by post-treatment operations such as extraction with an organic solvent, drying of the organic layer, and concentration, whereby compound (M4-1) can be obtained. Compound (R-7) is a commercially available compound or can be produced using known methods.

[0068] Also, compound (M4-1) can be produced in a one-step reaction (one-pot) by reacting compound (M6), compound (M1-3), and compound (R-7). The reaction can be carried out according to the method for producing compound (M4-1) from compound (M5), using compound (M1-3) usually in a ratio of 1 to 5 moles and compound (R-7) usually in a ratio of 1 to 50 moles per 1 mole of compound (M6).

[0069] Reference Production Method 16 Compound (M2-3-P) can be produced by reacting a compound represented by formula (M7) (hereinafter referred to as compound (M7)) and a compound represented by formula (R-8) (hereinafter referred to as compound (R-8)).

Chemical formula

[0070] The compound of the present invention or the compound X of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as this component) selected from the group consisting of the following group (a), group (b), group (c), and group (d). The above-mentioned mixing or combined use means using the compound of the present invention or the compound X of the present invention and this component simultaneously, separately, or at intervals of time. When the compound of the present invention or the compound X of the present invention and this component are used simultaneously, the compound of the present invention or the compound X of the present invention and this component may be contained in separate formulations, or may be contained in one formulation. One aspect of the present invention is a composition containing one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound of the present invention. One aspect of the present invention is a composition (hereinafter referred to as composition A) containing one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound X of the present invention.

[0071] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel antagonists (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor antagonist modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multi-site inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport system complexes I, II, III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients. These are described in the classification based on the mode of action of IRAC.

[0072] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These are described in the classification based on the mode of action of FRAC.

[0073] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).

[0074] Group (d) is a group of repellent components.

[0075] Examples of the combination of the present component and the compound X of the present invention are described below. For example, alanycarb + SX means the combination of alanycarb and SX. Note that the abbreviation SX means any one of the compound X of the present invention selected from the compound groups SX1 to SX2299 described in the examples. Also, all the present components described below are known components and can be obtained from commercially available formulations or produced by known methods. When the present component is a microorganism, it can also be obtained from a microorganism depository institution. The numbers in parentheses represent CAS RN (registered trademark).

[0076] The combination of the present component of the above group (a) and the compound X of the present invention: Abamectin + SX, Acephate + SX, Acequinocyl + SX, Acetamiprid + SX, Acetoprole + SX, Acrinathrin + SX, Acynonapyr + SX, Afidopyropen + SX, Afoxolaner + SX, Alanycarb + SX, Aldicarb + SX, Allethrin + SX, Alpha-cypermethrin + SX, Alpha-endosulfan + SX, Aluminium phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX,Bistrifluron + SX, Borax + SX, Boric acid + SX, Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium phosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chloropicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chromafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanamycin A + SX, Coumaphos + SX, Cryolite + SX, Cyanophos + SX, Cyantraniliprole + SX, Cyclaniliprole + SX,Cyclobutrifluram + SX, Cycloprothrin + SX, Cycloxaprid + SX, Cyenopyrafen + SX, Cyetpyrafen + SX, Cyflumetofen + SX, Cyfluthrin + SX, Cyhalodiamide + SX, Cyhalothrin + SX, Cyhexatin + SX, Cypermethrin + SX, Cyphenothrin + SX, Cyproflanilide + SX, Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-methyl + SX, Diafenthiuron + SX, Diazinon + SX, Dichlorvos + SX, Dicloromezotiaz + SX, Dicofol + SX, Dicrotophos + SX, Diflovidazin + SX, Diflubenzuron + SX, Dimefluthrin + SX, Dimethoate + SX, Dimethylvinphos + SX, Dimpropyridaz + SX, Dinotefuran + SX, Disodium octaborate + SX, Disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, Doramectin + SX,Dried leaves of Dryopteris filix-mas + SX, Emamectin-benzoate + SX, Empenthrin + SX, Endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, Epsilon-metofluthrin + SX, Epsilon-momfluorothrin + SX, Esfenvalerate + SX, Ethiofencarb + SX, Ethion + SX, Ethiprole + SX, Ethoprophos + SX, Etofenprox + SX, Etoxazole + SX, Extract of Artemisia absinthium + SX, Extract of Azadirachta indica + SX, Extract of Cassia nigricans + SX, Extract of clitoria ternatea + SX, Extract of Symphytum officinale + SX, Extract or simulated blend of Chenopodium ambrosioides + SX, Extract of Tanacetum vulgare + SX, Extract of Urtica dioica + SX, Extract of Viscum album + SX, Famphur + SX, Fenamiphos + SX, Fenazaquin + SX,fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX,Gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, Halfenprox + SX, Halofenozide + SX, Heptafluthrin + SX, Heptenophos + SX, Hexaflumuron + SX, Hexythiazox + SX, Potassium salt of hop beta acid + SX, Hydramethylnon + SX, Hydroprene + SX, Imicyafos + SX, Imidacloprid + SX, Imidaclothiz + SX, Imiprothrin + SX, Indazapyroxamet + SX, Indoxacarb + SX, Isocycloseram + SX, Isofenphos + SX, Isoprocarb + SX, Isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, Isoxathion + SX, Ivermectin + SX, Kadethrin + SX, Kappa-tefluthrin + SX, Kappa-bifenthrin + SX, Kinoprene + SX, Lambda-cyhalothrin + SX, Lenoremycin + SX, Lepimectin + SX, Lime sulfur + SX,Lotilaner + SX, Lufenuron + SX, Machine oil + SX, Malathion + SX, Mecarbam + SX, Meperfluthrin + SX, Metaflumizone + SX, Metam + SX, Methamidophos + SX, Methidathion + SX, Methiocarb + SX, Methomyl + SX, Methoprene + SX, Methoxychlor + SX, Methoxyfenozide + SX, Methyl bromide + SX, Metofluthrin + SX, Metolcarb + SX, Metoxadiazone + SX, Mevinphos + SX, Milbemectin + SX, Milbemycin oxime + SX, Momfluorothrin + SX, Monocrotophos + SX, Moxidectin + SX, Naled + SX, Nicofluprole + SX, Nicotine + SX, Nicotine-sulfate + SX, Nitenpyram + SX, Novaluron + SX, Noviflumuron + SX, Oil of the seeds of Chenopodium anthelminticum + SX, Omethoate + SX, Oxamyl + SX, Oxazosulfyl + SX,Oxydemeton-methyl + SX, Parathion + SX, Parathion-methyl + SX, Permethrin + SX, Phenothrin + SX, Phenthoate + SX, Phorate + SX, Phosalone + SX, Phosmet + SX, Phosphamidon + SX, Phosphine + SX, Phoxim + SX, Pirimicarb + SX, Pirimiphos-methyl + SX, Prallethrin + SX, Profenofos + SX, Profluthrin + SX, Propargite + SX, Propetamphos + SX, Propoxur + SX, Propylene glycol alginate + SX, Prothiofos + SX, Pyflubumide + SX, Pymetrozine + SX, Pyraclofos + SX, Pyrethrins + SX, Pyridaben + SX, Pyridalyl + SX, Pyridaphenthion + SX, Pyrifluquinazone + SX, Pyrimidifen + SX, Pyriminostrobin + SX, Pyriprole + SX, Pyriproxyfen + SX, Quinalphos + SX, Resmethrin + SX, Rotenone + SX,Ryanodine + SX, Sarolaner + SX, Selamectin + SX, Sigma-cypermethrin + SX, Silafluofen + SX, Sodium borate + SX, Sodium metaborate + SX, Spidoxamat + SX, Spinetoram + SX, Spinosad + SX, Spirodiclofen + SX, Spiromesifen + SX, Spiropidion + SX, Spirotetramat + SX, Sulfluramid + SX, Sulfotep + SX, Sulfoxaflor + SX, Sulfur + SX, Sulfuryl fluoride + SX, Tartar emetic + SX, Tau-fluvalinate + SX, Tebufenozide + SX, Tebufenpyrad + SX, Tebupirimfos + SX, Teflubenzuron + SX, Tefluthrin + SX, Temephos + SX, Terbufos + SX, Terpene constituents of the extract of chenopodium ambrosioides near ambrosioides + SX, Tetrachlorantraniliprole + SX, Tetrachlorvinphos + SX, Tetradifon + SX, Tetramethrin + SX, Tetramethylfluthrin + SX, Tetraniliprole + SX, Theta-cypermethrin + SX, Thiacloprid + SX, Thiamethoxam + SX, Thiocyclam + SX, Thiodicarb + SX, Thiofanox + SX, Thiometon + SX, Thiosultap-disodium + SX,Thiosultap-monosodium + SX, Tioxazafen + SX, Tolfenpyrad + SX, Tralomethrin + SX, Transfluthrin + SX, Triazamate + SX, Triazophos + SX, Trichlorfon + SX, Triflumezopyrim + SX, Triflumuron + SX, Trimethacarb + SX, Tyclopyrazoflor + SX, Vamidothion + SX, Wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, Xylylcarb + SX, Zeta-cypermethrin + SX, Zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX,(2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX,7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT crop protein Cry1A.105 + SX, BT crop protein Cry2Ab + SX, BT crop protein Vip3A + SX, BT crop protein mCry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulosis virus strain BV-0001 + SX, Anticarsia gemmatalis mNPV + SX,Autographa californica multiple nucleopolyhedrovirus (Autographa californica mNPV) + SX, Cydia pomonella granulovirus strain V15 (Cydia pomonella GV strain V15) + SX, Cydia pomonella granulovirus strain V22 (Cydia pomonella GV strain V22) + SX, Cryptophlebia leucotreta granulovirus (Cryptophlebia leucotreta GV) + SX, Dendrolimus punctatus cytoplasmic polyhedrosis virus (Dendrolimus punctatus cypovirus) + SX, Helicoverpa armigera nucleopolyhedrovirus strain BV-0003 (Helicoverpa armigera NPV strain BV-0003) + SX, Helicoverpa zea nucleopolyhedrovirus (Helicoverpa zea NPV) + SX, Lymantria dispar nucleopolyhedrovirus (Lymantria dispar NPV) + SX, Mamestra brassicae nucleopolyhedrovirus (Mamestra brassicae NPV) + SX, Mamestra configurata nucleopolyhedrovirus (Mamestra configurata NPV) + SX, Neodiprion abietis nucleopolyhedrovirus (Neodiprion abietis NPV) + SX, Neodiprion lecontei nucleopolyhedrovirus (Neodiprion lecontei NPV) + SX, Neodiprion sertifer nucleopolyhedrovirus (Neodiprion sertifer NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrovirus (Orgyia pseudotsugata NPV) + SX, Pieris rapae granulovirus (Pieris rapae GV) + SX, Plodia interpunctella granulovirus (Plodia interpunctella GV) + SX, Spodoptera exigua multiple nucleopolyhedrovirus (Spodoptera exigua mNPV) + SX,Spodoptera littoralis multiple nucleopolyhedrovirus (Spodoptera littoralis mNPV) + SX, Spodoptera litura nucleopolyhedrovirus (Spodoptera litura NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus sphaericus Serotype strain H5a5b + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX,Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306) + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX,Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX,Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,

[0077] Combination of the present component of group (b) and the compound X of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin-S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chitin + SX, chloroinconazide + SX, chloroneb + SX, chlorothalonil + SX,Chlozolinate + SX, Colletochlorin B + SX, Copper(II) acetate + SX, Copper(II) hydroxide + SX, Copper oxychloride + SX, Copper(II) sulfate + SX, Coumoxystrobin + SX, Cyazofamid + SX, Cyflufenamid + SX, Cymoxanil + SX, Cyproconazole + SX, Cyprodinil + SX, Dichlobentiazox + SX, Dichlofluanid + SX, Diclocymet + SX, Diclomezine + SX, Dicloran + SX, Diethofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + SX, Dimethirimol + SX, Dimethomorph + SX, Dimoxystrobin + SX, Diniconazole + SX, Diniconazole-M + SX, Dinocap + SX, Dipotassium hydrogenphosphite + SX, Dipymetitrone + SX, Dithianon + SX, Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX,Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epoxiconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Extract of Melaleuca alternifolia + SX, Extract of Reynoutria sachalinensis + SX, Extract of the cotyledons of lupine plantlets ("BLAD") + SX, Extract of Allium sativum + SX, Extract of Equisetum arvense + SX, Extract of Tropaeolum majus + SX, Famoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Fenfuram + SX, Fenhexamid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentin acetate + SX, Fentin chloride + SX,Fentin hydroxide + SX, Ferbam + SX, Ferimzone + SX, Florylpicoxamid + SX, Fluazinam + SX, Flubeneteram + SX, Fludioxonil + SX, Flufenoxadiazam + SX, Flufenoxystrobin + SX, Fluindapyr + SX, Flumetylsulforim + SX, Flumorph + SX, Fluopicolide + SX, Fluopyram + SX, Fluopimomide + SX, Fluoroimide + SX, Fluoxapiprolin + SX, Fluoxastrobin + SX, Fluoxytioconazole + SX, Fluquinconazole + SX, Flusilazole + SX, Flusulfamide + SX, Flutianil + SX, Flutolanil + SX, Flutriafol + SX, Fluxapyroxad + SX, Folpet + SX, Fosetyl + SX, Fosetyl-aluminium + SX, Fuberidazole + SX, Furalaxyl + SX, Furametpyr + SX, Guazatine + SX, Hexaconazole + SX, Hymexazole + SX,Imazalil + SX, Imibenconazole + SX, Iminoctadine + SX, Iminoctadine triacetate + SX, Inpyrfluxam + SX, Iodocarb + SX, Ipconazole + SX, Ipfentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX, Iprovalicarb + SX, Isofetamid + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Leaves and bark of Quercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metarylpicoxamid + SX, Metconazole + SX, Methasulfocarb + SX, Metiram + SX,Metominostrobin + SX, Metrafenone + SX, Methyltetraprole + SX, Myclobutanil + SX, Naftifine + SX, Nuarimol + SX, Octhilinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX, Oxathiapiprolin + SX, Oxine - copper + SX, Oxolinic acid + SX, Oxpoconazole + SX, Oxpoconazole fumarate + SX, Oxycarboxin + SX, Oxytetracycline + SX, Pefurazoate + SX, Penconazole + SX, Pencycuron + SX, Penflufen + SX, Penthiopyrad + SX, Phenamacril + SX, Phosphorous acid + SX, Phthalide + SX, Picarbutrazox + SX, Picoxystrobin + SX, Piperalin + SX, Polyoxins + SX, Potassium hydrogencarbonate + SX, Potassium dihydrogenphosphite + SX, Probenazole + SX, Prochloraz + SX, Procymidone + SX,Propamidine + SX, Propamocarb + SX, Propiconazole + SX, Propineb + SX, Proquinazid + SX, Prothiocarb + SX, Prothioconazole + SX, Pydiflumetofen + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyraoxystrobin + SX, Pyrapropoyne + SX, Pyraziflumid + SX, Pyrazophos + SX, Pyribencarb + SX, Pyributicarb + SX, Pyridachlometyl + SX, Pyrifenox + SX, Pyrimethanil + SX, Pyrimorph + SX, Pyriofenone + SX, Pyrisoxazole + SX, Pyroquilon + SX, Quillaja extract + SX, Quinconazole + SX, Quinofumelin + SX, Quinoxyfen + SX, Quintozene + SX, Saponins of Chenopodium quinoa + SX, Seboctylamine + SX, Sedaxane + SX, Silthiofam + SX, Simeconazole + SX, Sodium hydrogencarbonate + SX,Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, Thifluzamide + SX, Thiophanate + SX, Thiophanate-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX, Tolclofos-methyl + SX, Tolfenpyrad + SX, Tolprocarb + SX, Tolylfluanid + SX, Triadimefon + SX, Triadimenol + SX, Triazoxide + SX, Triclopyricarb + SX, Tricyclazole + SX, Tridemorph + SX, Trifloxystrobin + SX, Triflumizole + SX, Triforine + SX, Triticonazole + SX, Validamycin + SX, Valifenalate + SX, Vinclozolin + SX, Yellow mustard powder + SX, Zinc thiazole + SX, Zineb + SX, Ziram + SX,Zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N, '-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,(3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,(1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX,Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX,Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX,Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX,Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,

[0078] Combination of the main component of the above group (c) and the compound X of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX,Decan-1-ol + SX, Dichlorprop + SX, Dikegulac + SX, Dimethipin + SX, Diquat + SX, Ethephon + SX, Ethychlozate + SX, Flumetralin + SX, Flurprimidol + SX, Forchlorfenuron + SX, Formononetin + SX, Gibberellin A + SX, Gibberellin A3 + SX, Inabenfide + SX, Kinetin + SX, Lipochitooligosaccharide SP104 + SX, Maleic hydrazide + SX, Mefluidide + SX, Mepiquat-chloride + SX, Oxidized glutathione + SX, Paclobutrazol + SX, Pendimethalin + SX, Prohexadione-calcium + SX, Prohydrojasmon + SX, Pyraflufen-ethyl + SX, Sintofen + SX, Sodium 1-naphthaleneacetate + SX, Sodium cyanate + SX, Thidiazuron + SX, Triapenthenol + SX, Tribufos + SX, Trinexapac-ethyl + SX, Uniconazole-P + SX,2-(Naphthalen-1-yl)acetamide + SX, [4-Oxo-4-(2-phenylethyl)amino]butyric acid + SX, Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-Chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX, Bradyrhizobium japonicum USDA 110 + SX,Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX。,

[0079] Combination of the present component of group (d) and the compound X of the present invention: Anthraquinone + SX, Deet + SX, Icaridin + SX。

[0080] The ratio of the compound X of the present invention to the present component is not particularly limited, but examples of the weight ratio (compound X of the present invention: present component) include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0081] The compound X of the present invention is effective against harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks. Examples of harmful arthropods, harmful nematodes, and harmful mollusks include the following.

[0082] Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus; Cicadellidae such as Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Cofana spectra, Amrasca biguttula biguttula; Aphrophoridae such as Philaenus spumarius; Cercopidae such as Mahanarva posticata, Mahanarva fimbriolataAphididae such as Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzus persicae, Brachycaudus helichrysi, Brevicoryne brassicae, Dysaphis plantaginea (rosy apple aphid), Lipaphis erysimi, Macrosiphum euphorbiae, Aulacorthum solani, Nasonovia ribisnigri, Rhopalosiphum padi, Rhopalosiphum maidis, Toxoptera citricida, Hyalopterus pruni, Melanaphis sacchari, Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, Sitobion avenae (English grain aphid), etc.; Phylloxeridae such as Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, etc.Adelgidae such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae; Pentatomidae such as Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, Euschistus heros, Piezodorus guildinii, Oebalus pugnax, Dichelops melacanthus; Cydnidae such as Scaptocoris castanea; Alydidae such as Riptortus clavatus, Leptocorisa chinensis, Leptocorisa acuta; Coreidae such as Cletus punctiger, Leptoglossus australis; Lygaeidae such as Cavelerius saccharivorus, Togo hemipterus, Blissus leucopterus;Miridae such as Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, Lygus lineolaris, etc.; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Pealius euryae, etc.; Diaspididae such as Abgrallaspis cyanophylli, Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, Unaspis citri, etc.; Coccidae such as Ceroplastes rubens, etc.; Margarodidae such as Icerya purchasi, Icerya seychellarum, etc.Pseudococcidae such as Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, Brevennia rehi, etc.; Psyllidae such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Cacopsylla pyricola, etc.; Tingidae such as Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, etc.; Cimicidae such as Cimex lectularius, Cimex hemipterus, etc.; Cicadidae such as Quesada gigas, etc.; Reduviidae such as Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, Rhodonius prolixus, etc.

[0083] Lepidoptera: Crambidae such as Chilo suppressalis, Chilo polychrysus, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis, Hellula undalis, Herpetogramma luctuosale, Parapediasia teterrellus, Nymphula depunctalis, Diatraea saccharalis, Leucinodes orbonalis, etc.; Pyralidae such as Elasmopalpus lignosellus, Plodia interpunctella, Euzophera batangensis, Cadra cautella, etc.Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Autographa nigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis spp. such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Anticarsia gemmatalis, Alabama argillacea, Noctuidae such as Hydraecia immanis; Pieridae such as Pieris rapae;Tortricidae such as Grapholita molesta, Grapholita dimorpha, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema, Citripestis sagittiferella, Lobesia botrana, etc.; Gracillariidae such as Caloptilia theivora, Phyllonorycter ringoniella, etc.; Carposinidae such as Carposina sasakii, etc.; Lyonetiidae such as Leucoptera coffeella, Lyonetia clerkella, Lyonetia prunifoliella, etc.; Lymantriidae such as Lymantria spp. like Lymantria dispar, Euproctis spp. like Euproctis pseudoconspersa, etc.; Plutellidae such as Plutella xylostella, etc.Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Tuta absoluta; Arctiidae such as Hyphantria cunea; Castniidae such as Telchin licus; Cossidae such as Cossus insularis; Geometridae such as Ascotis selenaria; Limacodidae such as Parasa lepida; Stathmopodidae such as Stathmopoda masinissa; Sphingidae such as Acherontia lachesis; Sesiidae such as Nokona feralis, Synanthedon hector, Synanthedon tenuis; Hesperiidae such as Parnara guttata; Tineidae such as Tinea translucens, Tineola bisselliella.;

[0084] Order Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, Scirtothrips perseae, etc.; Phlaeothripidae such as Haplothrips aculeatus, etc.

[0085] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, Pegomya cunicularia, etc.; Ulidiidae such as Tetanops myopaeformis, etc.; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, Chromatomyia horticola, etc.; Chloropidae such as Chlorops oryzae, etc.; Tephritidae such as Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rhacochlaena japonica, etc.; Ephydridae such as Hydrellia griseola, Hydrellia philippina, Hydrellia sasakii, etc.; Drosophilidae such as Drosophila suzukii, Drosophila melanogaster, etc.; Phoridae such as Megaselia spiracularis, etc.; Psychodidae such as Clogmia albipunctata, etc.; Sciaridae such as Bradysia difformis, etc.Cecidomyiidae such as Hessian fly (Mayetiola destructor), rice gall midge (Orseolia oryzae); Diopsidae such as Diopsis macrophthalma; Glossinidae such as Glossina palpalis, Glossina morsitans; Simuliidae such as Simulium japonicum, Simulium damnosum; Phlebotominae; Tipulidae such as Tipula aino, common crane fly (Tipula oleracea), European crane fly (Tipula paludosa); Culicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus; Simuliidae such as Prosimulium yezoensis, Simulium ornatum; Tabanidae such as Tabanus trigonusMuscidae such as Musca domestica, Muscina stabulans, Stomoxys calcitrans, Haematobia irritans, etc.; Calliphoridae; Sarcophagidae; Chironomidae such as Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai, etc.; Fannidae;

[0086] Coleoptera: Diabrotica spp. (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae)), banded cucumber beetle (Diabrotica balteata), cucumber beetle (Diabrotica speciosa), etc., bean leaf beetle (Cerotoma trifurcata), cereal leaf beetle (Oulema melanopus), flea beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata), cabbage flea beetle (Phyllotreta cruciferae), Western black flea beetle (Phyllotreta pusilla), cabbage stem flea beetle (Psylliodes chrysocephala), hop flea beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flea beetle (Chaetocnema pulicaria), sweet potato flea beetle (Chaetocnema confinis), potato flea beetle (Epitrix cucumeris), rice hispa (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-spotted leaf beetle (Laccoptera quadrimaculata), tobacco flea beetle (Epitrix hirtipennis), etc. of Chrysomelidae; seed corn beetle (Stenolophus lecontei), slender seed corn beetle (Clivina impressifrons), etc. of Carabidae;Scarabaeidae such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophylla picea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp., Phyllophaga spp. such as Phyllophaga crinita, Diloboderus spp. such as Diloboderus abderus; Anthriibidae such as Araecerus coffeae; Aponidae such as Cylas formicarius; Bruchidae such as Zabrotes subfasciatus; Scolytidae such as Tomicus piniperda, Hypothenemus hampei;Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Sitophilus oryzae, Sitophilus granarius, Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineaticollis, Anthonomus grandis, Sphenophorus venatus, Sphenophorus callosus, Sternechus subsignatus, Sphenophorus levis, Scepticus griseus, Scepticus uniformis, Aracanthus spp. such as Aracanthus mourei, Curculionidae such as Eutinobothrus brasiliensis; Tenebrionidae such as Tribolium castaneum, Tribolium confusum, Alphitobius diaperinus; Coccinellidae such as Epilachna vigintioctopunctata; Bostrychidae such as Lyctus brunneus, Rhizopertha dominica; Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungiiClick beetles (Elateridae) such as Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., etc.; rove beetles (Staphylinidae) such as Paederus fuscipes, etc.; skin beetles (Dermestidae) such as Anthrenus verbasci, Dermestes maculates, Trogoderma granarium, etc.; cigarette beetles (Anobiidae) such as Lasioderma serricorne, Stegobium paniceum, etc.; flat grain beetles (Laemophloeidae) such as Cryptolestes ferrugineus, etc.; sawtoothed grain beetles (Silvanidae) such as Oryzaephilus surinamensis, etc., and pollen beetles (Nitidulidae) such as Brassicogethes aeneus, etc.

[0087] Orthoptera: Acrididae such as Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina, Anacridium melanorhodon, Calliptamus italicus, Melanoplus differentialis, Melanoplus bivittatus, Melanoplus sanguinipes, Melanoplus femurrubrum, Camnula pellucida, Schistocerca gregaria, Gastrimargus musicus, Austracris guttulosa, Oxya yezoensis, Oxya japonica, Patanga succincta; Gryllotalpidae such as Gryllotalpa orientalis; Gryllidae such as Acheta domestica, Teleogryllus emma; Tettigoniidae such as Anabrus simplex.

[0088] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp. such as Atta capiguara, Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monommorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes and other Camponotus spp., Pogonomyrmex occidentalis and other Pogonomyrmex spp., Wasmania auropunctata and other Wasmania spp., Anoplolepis gracilipes and other Formicidae; Vespidae such as Vespa mandarinia, Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae; Siricidae such as Urocerus gigas; Bethylidae.

[0089] Order Blattodea: Family Ectobiidae such as Blattella germanica; Family Blattidae such as Periplaneta fuliginosa, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Blatta orientalis; Family Termitidae such as Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans.

[0090] Order Siphonaptera: Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Echidnophaga gallinacea, etc.; Hectopsyllidae such as Tunga penetrans, etc.; Ceratophyllidae such as Nosopsyllus fasciatus, etc.

[0091] Psocodea: Pediculidae such as Pediculus humanus capitis; Pthiridae such as Pthirus pubis; Haematopinidae such as Haematopinus eurysternus, Haematopinus suis; Linognathidae such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicoliidae such as Bovicola bovis, Bovicola ovis, Bovicola breviceps, Damalinia forficula, Werneckiella spp.; Trichodectidae such as Trichodectes canis, Felicola subrostratus; Menoponidae such as Menopon gallinae, Menacanthus stramineus, Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelididae such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, Liposcelis entomophila.

[0092] Thysanura: Lepismatidae such as Ctenolepisma villosa and Lepisma saccharina.

[0093] Acari: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligonychus spp.; Eriophyidae such as Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus, etc. of the family Ixodidae; Argas persicus, Ornithodoros hermsi, Ornithodoros turicata, etc. of the family Argasidae; Tyrophagus putrescentiae, Tyrophagus similis, etc. of the family Acaridae; Dermatophagoides farinae, Dermatophagoides pteronyssinus, etc. of the family Pyroglyphidae;Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, Cheyletiella yasguri, etc.; Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp., etc.; Sarcoptidae such as Notoedres cati, Notoedres muris, Sarcoptes scabiei, etc.; Listrophoridae such as Listrophorus gibbus; Dermanyssidae such as Dermanyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum, Ornithonyssus bacoti, etc., Varroidae such as Varroa jacobsoni, etc., Demodicidae such as Demodex canis, Demodex cati, etc., Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium scutellare, etc.

[0094] Order Araneae: Eutichuridae such as Cheiracanthium japonicum; Theridiidae such as Latrodectus hasseltii. Order Polydesmida: Family Paradoxosomatidae such as Oxidus gracilis and Nedyopus tambanus. Order Isopoda: Family Armadillidiidae such as Armadillidium vulgare. Class Chilopoda: Family Scutigeridae such as Thereuonema hilgendorfi; Family Scolopendridae such as Scolopendra subspinipes; Family Ethopolyidae such as Bothropolys rugosus. Class Gastropoda: Family Limacidae such as Limax marginatus and Limax flavus; Family Philomycidae such as Meghimatium bilineatum; Family Ampullariidae such as Pomacea canaliculata; Family Lymnaeidae such as Austropeplea ollula.

[0095] Nematodes: Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, Radopholus similis; Heteroderidae such as Meloidogyne javanica, Meloidogyne incognita, guava root - knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, Globodera rostochiensis, Globodera pallida; Hoplolaimidae such as Rotylenchulus reniformis; Anguinidae such as Nothotylenchus acris, Ditylenchus dipsaci; Tylenchulidae such as Tylenchulus semipenetrans; Longidoridae such as Xiphinema index; Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus.

[0096] Harmful arthropods such as harmful insects and harmful mites, harmful mollusks, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes that have developed reduced drug sensitivity or drug resistance to insecticides, acaricides, molluscicides, or nematicides.

[0097] As a method for controlling harmful arthropods of the present invention, an effective amount of the compound of the present invention, the compound X of the present invention, or the composition A is applied directly to harmful arthropods and / or to the habitats (plants, soil, indoors, animals, etc.) of harmful arthropods. Examples of the method for controlling harmful arthropods of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

[0098] The compound of the present invention, the compound X of the present invention, or the composition A is usually mixed with an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier and a surfactant, and if necessary, formulation aids such as a binder, a dispersant, and a stabilizer are added to prepare an aqueous suspension formulation, an oily suspension formulation, an oil formulation, an emulsion, an emulsion formulation, a microemulsion formulation, a microcapsule formulation, a wettable powder, a granule wettable powder, a powder, a granule, a tablet, an aerosol, a resin formulation, etc. It can be formulated and used not only in these formulations but also in the dosage forms described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers - 271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259 - 2517. These formulations usually contain the compound of the present invention, the compound X of the present invention, or the composition A in a weight ratio of 0.0001 to 99%.

[0099] Examples of the solid carrier include clays (such as pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granular materials of chemical fertilizers (such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (such as polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0100] Examples of the liquid carrier include water, alcohols (such as ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (such as acetone, cyclohexanone, etc.), aromatic hydrocarbons (such as xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (such as hexane, cyclohexane, etc.), esters (such as ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (such as acetonitrile, etc.), ethers (such as ethylene glycol dimethyl ether, etc.), amides (such as N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (such as dimethyl sulfoxide, etc.), lactams (such as N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (such as oleic acid, etc.), and vegetable oils (such as soybean oil, etc.).

[0101] Examples of the gaseous carrier include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0102] Examples of the surfactant include nonionic surfactants (such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, etc.) and anionic surfactants (such as alkyl sulfonate, alkyl aryl sulfonate, alkyl sulfate, etc.). Specifically, Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark), etc. are included.

[0103] Examples of other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc. Specifically, for example, polysaccharides (such as starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (such as polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, and dibutylhydroxytoluene are included.

[0104] In the present invention, examples of the plant include the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0105] The vegetative reproductive organ means a part of a plant such as the root, stem, leaf, etc., which has the ability to grow when separated from the main body and placed in the soil. Examples of vegetative reproductive organs include tuberous root, creeping root, bulb, corm (or solid bulb), tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. Note that stolons are sometimes called runners, propagules are also called bulbils, and can be divided into broad buds and bulbils. Vine cutting means the shoots (a general term for leaves and stems) of sweet potatoes and yams, etc. Bulbs, corms, tubers, rhizomes, cane cuttings, rhizophores, or tuberous roots are collectively called bulbs. The cultivation of potatoes begins by planting tubers in the soil, and the tubers used are generally called seed tubers.

[0106] As a method for controlling harmful arthropods by applying an effective amount of the compound of the present invention, the compound X of the present invention, or the composition A to soil, for example, there are methods of applying an effective amount of the compound of the present invention, the compound X of the present invention, or the composition A to the soil before or after planting a plant, methods of applying an effective amount of the compound of the present invention, the compound X of the present invention, or the composition A to the rhizosphere of a crop to be protected from damage such as feeding by harmful arthropods, and methods of allowing an effective amount of the compound of the present invention, the compound X of the present invention, or the composition A to penetrate and migrate into the plant body from the roots or the like to control harmful arthropods that feed on the plant. More specifically, for example, hole treatment (hole spraying, hole treatment soil mixing), base treatment (base spraying, base soil mixing, base irrigation, post-seedling base treatment), furrow treatment (furrow spraying, furrow soil mixing), ridging treatment (ridging spraying, ridging soil mixing, in-season ridging spraying), ridging treatment at sowing (ridging spraying at sowing, ridging soil mixing at sowing), overall treatment (overall soil spraying, overall soil mixing), side ridging treatment, water surface treatment (water surface application, water surface application after flooding), and other soil spraying treatments (in-season granule foliar spraying, spraying under the canopy or around the main trunk, soil surface spraying, soil surface mixing, hole sowing spraying, ridge surface spraying, inter-plant spraying), and other irrigation treatments (soil irrigation, seedling irrigation, chemical solution injection treatment, ground-level irrigation, chemical drip irrigation, chemigation), seedling box treatment (seedling box spraying, seedling box irrigation, seedling box chemical solution flooding), seedling tray treatment (seedling tray spraying, seedling tray irrigation, seedling tray chemical solution flooding), seedbed treatment (seedbed spraying, seedbed irrigation, flooded seedling substitute seedbed spraying, seedling dipping), bed soil mixing treatment (bed soil mixing, pre-sowing bed soil mixing, spraying before covering soil at sowing, spraying after covering soil at sowing, covering soil mixing), and other treatments (soil mixing with soil heaped up, hoeing in, topsoil mixing, soil mixing at the rain runoff part, planting position treatment, granule inflorescence spraying, paste fertilizer mixing).

[0107] Examples of seed treatment include treating the seeds or vegetative reproductive organs with the compound of the present invention, compound X of the present invention, or composition A. Specifically, for example, a spraying treatment in which a suspension of the compound of the present invention, compound X of the present invention, or composition A is atomized and sprayed onto the seed surface or the vegetative reproductive organ surface; a coating treatment in which the compound of the present invention, compound X of the present invention, or composition A is applied to the seeds or vegetative reproductive organs; a dipping treatment in which the seeds or vegetative reproductive organs are immersed in a chemical solution of the compound of the present invention, compound X of the present invention, or composition A for a certain period of time; and a method of coating the seeds or vegetative reproductive organs with a carrier containing the compound of the present invention, compound X of the present invention, or composition A (film coating treatment, pellet coating treatment, etc.). Examples of the above-mentioned vegetative reproductive organs include seed tubers in particular. When treating seeds or vegetative reproductive organs with composition A, composition A can be treated as a single formulation on the seeds or vegetative reproductive organs, or can be treated on the seeds or vegetative reproductive organs in multiple separate times as different multiple formulations. Examples of the method of treating composition A in multiple separate times as different multiple formulations include, for example, a method of treating with a formulation containing only the compound of the present invention or compound X of the present invention as the active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this component; and a method of treating with a formulation containing the compound of the present invention or compound X of the present invention and this component as the active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing a component other than the treated this component. The seeds or vegetative reproductive organs holding the compound of the present invention, compound X of the present invention, or composition A in the present invention mean those in a state where the compound of the present invention, compound X of the present invention, or composition A is attached to the surface of the seeds or vegetative reproductive organs. For the above-mentioned seeds or vegetative reproductive organs holding the compound of the present invention, compound X of the present invention, or composition A, materials other than the compound of the present invention, compound X of the present invention, or composition A may be attached before and after the compound of the present invention, compound X of the present invention, or composition A is attached to the seeds or vegetative reproductive organs. In addition, when the composition A adheres to the surface of the seed or vegetative reproductive organ as a layer, the layer may consist of one layer or multiple layers. When it consists of multiple layers, each layer may be a layer containing one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer not containing active ingredients. The seeds or vegetative reproductive organs holding the compound of the present invention, the compound X of the present invention or the composition A can be obtained, for example, by applying a formulation containing the compound of the present invention, the compound X of the present invention or the composition A to the seeds or vegetative reproductive organs by the above-described seed treatment method.

[0108] When the compound of the present invention, the compound X of the present invention or the composition A is used for controlling harmful arthropods in the agricultural field, the application rate is usually 1 to 10,000 g in terms of the amount of the compound of the present invention or the compound X of the present invention per 10,000 m 2 When treating seeds or vegetative reproductive organs, the amount of the compound of the present invention or the compound X of the present invention is usually applied in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproductive organs. When the compound of the present invention, the compound X of the present invention or the composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm and applied, and granules, powders, etc. are usually applied as they are.

[0109] In addition, the compound X of the present invention or the composition A can also be treated by methods such as winding a resin formulation processed into a sheet or string around a crop, stretching it near the crop, or laying it on the soil at the base of the plant.

[0110] When the compound of the present invention, the compound X of the present invention or the composition A is used for controlling harmful arthropods inhabiting indoors, the application rate is usually 0.01 to 1000 mg in terms of the amount of the compound of the present invention or the compound X of the present invention per 1 m of the treatment area when treating the surface, and when treating the space, it is per 1 m of the treatment space 2 When treating the space, it is usually 0.01 to 1000 mg in terms of the amount of the compound of the present invention or the compound X of the present invention per 1 m of the treatment space 3The amount of the compound of the present invention or Compound X of the present invention is usually 0.01 to 500 mg. When the compound of the present invention, Compound X of the present invention or Composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water and applied so that the active ingredient concentration becomes 0.1 to 10,000 ppm, and oils, aerosol agents, fumigants, bait agents, etc. are applied as they are.

[0111] When the compound of the present invention, Compound X of the present invention or Composition A is used for controlling external parasites of livestock such as cows, horses, pigs, sheep, goats, chickens, etc. and small animals such as dogs, cats, rats, mice, etc., it can be used for animals by a method known in veterinary medicine. As specific usage methods, for the purpose of systemic suppression, it is administered, for example, by tablets, incorporation into feed, suppositories, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and for the purpose of non-systemic suppression, for example, an oil or aqueous liquid is sprayed, pour-on treatment or spot-on treatment is performed, the animal is washed with a shampoo formulation or a resin formulation is made into a collar or ear tag and attached to the animal, etc. The amount of the compound of the present invention or Compound X of the present invention when administered to an animal is usually in the range of 0.1 to 1000 mg per 1 kg of the animal's body weight.

[0112] The compound of the present invention, Compound X of the present invention or Composition A can be used as a controlling agent for harmful arthropods in agricultural fields such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0113] Maize (dent, flint, soft, pop, waxy, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, glutinous barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oats type, spring oats type), sorghum, cotton (upland variety, pima variety), soybean (fully mature seed harvest variety, edamame variety, green forage variety, each indeterminate growth type, determinate growth type, semi-determinate growth type), peanut, buckwheat, sugar beet (for sugar production, for feed, root vegetable, leaf vegetable, for fuel), rapeseed (winter rapeseed type, spring rapeseed type), sunflower (for oil extraction, for food, for ornamental purposes), sugarcane, tobacco, tea tree, mulberry, Solanaceae vegetables (eggplant, tomato, pepper, chili pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard spinach, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), Alliaceae vegetables (green onion, onion, garlic, asparagus, etc.), Apiaceae vegetables (carrot, parsley, celery, American lovage, etc.), Amaranthaceae vegetables (spinach, red amaranth, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, pome fruits (apple, pear, Japanese pear, Chinese pear, quince, membrillo, etc.), stone fruits (peach, plum, nectarine, Japanese apricot, apricot, anzu, prune, etc.), citrus fruits (satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, fig, olive, loquat, banana, coffee, date palm, coconut palm, ornamental plants, forest plants, grasses,Forage grasses.

[0114] The above plants are not particularly limited as long as they are commonly cultivated varieties. The above plants also include plants that can be produced by natural crossbreeding, plants that can occur by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants imparted with resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants capable of synthesizing selective toxins known in the genus Bacillus such as Bacillus thuringiensis; and plants capable of imparting specific insecticidal activity by synthesizing gene fragments partially matching endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect body.

Examples

[0115] Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, test examples, etc., but the present invention is not limited only to these examples. In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, t-Bu represents a tert-butyl group, C2F5 represents a perfluoroethyl group, c-Pr represents a cyclopropyl group, Bn represents a benzyl group, Ph represents a phenyl group, Py2 represents a 2-pyridyl group, Py3 represents a 3-pyridyl group, and Py4 represents a 4-pyridyl group. When c-Pr, Ph, Py2, Py3, and Py4 have substituents, the substituents are described together with the substitution positions in front of the symbols. For example, 1-CN-c-Pr represents a 1-cyanocyclopropyl group, 3,4-F2-Ph represents a 3,4-difluorophenyl group, 2-C2F5-Ph represents a 2-(perfluoroethyl)phenyl group, 4-SO2CF3-Ph represents a 4-(trifluoromethanesulfonyl)phenyl group, 3,4-(OCF3)2-Ph represents a 3,4-bis(trifluoromethoxy)phenyl group, 3-SCF3-4-OCF3-Ph represents a 3-[(trifluoromethyl)thio]-4-(trifluoromethoxy)phenyl group, and 4-CF3-Py2 represents a 4-(trifluoromethyl)-2-pyridyl group.

[0116] First, production examples of the compound X of the present invention and its production intermediates are shown.

[0117] When the physical property values of the compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [M-H] - and the retention time (hereinafter referred to as RT) are described. The conditions for liquid chromatography (hereinafter referred to as LC) are as follows.

[0118] [LC Conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemical Substances Evaluation and Research Institute, Incorporated Administrative Agency) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% aqueous formic acid solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Gradient condition: Perform liquid delivery with the concentration gradient described in [Table LC1].

[0119] [Table 1]

[0120] Reference Production Example 1 To a mixture of 1.1 g of 6-bromo-3-(ethylthio)imidazo[1,2-a]pyridin-2-amine (hereinafter referred to as Intermediate Z) produced by the method described in International Publication No. 2018 / 052136 and 8 mL of THF, 0.83 g of 4-(trifluoromethyl)benzoyl chloride was added, followed by addition of 1.1 mL of triethylamine, and the mixture was stirred at room temperature for 30 minutes. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.4 g of Intermediate 1 represented by the following formula. [Chemical Formula] Intermediate 1: 1 1H-NMR (CDCl3) δ: 9.39 (1H, s), 8.52 (1H, s), 8.07 (2H, d), 7.79 (2H, d), 7.57 (1H, d), 7.47 (1H, d), 2.75 (2H, q), 1.24 (3H, t).

[0121] Reference Production Example 2 A mixture of 6.12 g of Intermediate Z, 5.0 g of 3-(trifluoromethylthio)benzoic acid, 0.55 g of 4-(dimethylamino)pyridine, 50 mL of pyridine, and 6.47 g of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride was stirred at 100 °C for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 6.57 g of Intermediate 2 represented by the following formula. [Chemical Formula] Intermediate 2: 11H-NMR (CDCl3) δ: 8.56 - 8.53 (2H, m), 8.24 (1H, s), 8.10 (1H, d), 7.87 (1H, d), 7.60 (1H, t), 7.54 (1H, d), 7.39 (1H, d), 2.77 (2H, q), 1.25 (3H, t).

[0122] Reference Production Example 2-1 The compounds produced according to Reference Production Example 2 and their physical property values are shown below. Formula (A-1)

Chemical Structure

[0123]

Table 2

[0124] In the compound represented by formula (A-1), A 2 、A 3 、A 4 、A 5 、G 4 and R 3b is a compound in which the combination of is any of the combinations described in [Table AA-1].

[0125]

Table 3

[0126] Reference Production Example 3 To a mixture of 500 mg of Intermediate 1 and 5 mL of chloroform, 830 mg of mCPBA (purity 70%, containing 30% water) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. To the resulting mixture, saturated aqueous sodium hydrogen carbonate solution and aqueous sodium thiosulfate solution were added successively, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 260 mg of Intermediate 26.

Chemical Structure

[0127] Reference Production Example 3-1 The compounds produced according to Reference Production Example 3 and their physical property values are shown below. Formula (A-2) [Chemical Formula] In the compound represented by, A 2 , A 3 , A 4 , A 5 , and R 3b A compound in which the combination of is any of the combinations described in [Table A-2].

[0128] [Table 4] Intermediate 27: 1 H-NMR (CDCl3) δ: 9.78 (1H, s), 8.80 - 8.76 (1H, m), 8.27 (1H, s), 8.07 (1H, d), 7.89 (1H, d), 7.72 (1H, d), 7.64 - 7.57 (2H, m), 3.33 (2H, q), 1.36 (3H, t). Intermediate 28: 1 H-NMR (CDCl3) δ: 9.80 (1H, s), 8.77 (1H, s), 8.02 (2H, d), 7.81 (2H, d), 7.72 (1H, d), 7.59 (1H, d), 3.32 (2H, q), 1.36 (3H, t). Intermediate 29: 1 H-NMR (CDCl3) δ: 10.09 (1H, s), 8.84 - 8.82 (1H, m), 8.36 (1H, t), 7.73 (1H, d), 7.61 - 7.58 (2H, m), 7.49 (1H, d), 3.32 (2H, q), 1.37 (3H, t). Intermediate 42: 11H-NMR (CDCl3) δ: 9.83 (1H, s), 8.86 (1H, s), 8.10 (2H, d), 7.80 (2H, d), 7.71 (1H, dd), 7.62 (1H, d), 3.31 (2H, q), 1.36 (3H, t).

[0129] Reference Production Example 4 To a mixture of 3.00 g of 4-(trifluoromethyl)anthranilic acid and 22 mL of THF, a mixture of 1.52 g of triphosgene and 15 mL of THF was added dropwise under ice cooling. The resulting mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 3.30 g of Intermediate 30 represented by the following formula.

Chemical formula

[0130] Reference Production Example 4-1 The compound produced according to Reference Production Example 4 and its physical property values are shown below.

Chemical formula

[0131] Reference Production Example 5 To a mixture of 300 mg of Intermediate Z300 and 4 mL of THF, 2.2 mL of potassium bis(trimethylsilyl)amide (1 mol / L THF solution) was added dropwise at -78 °C under a nitrogen atmosphere, and the mixture was stirred for 30 minutes. To the resulting mixture, a mixture of 254 mg of Intermediate 30 and 4 mL of THF was added, and the mixture was stirred at room temperature for 30 minutes. An aqueous saturated ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Hexane was added to the obtained residue, and the precipitated solid was filtered. The obtained solid was washed with hexane and dried under reduced pressure to obtain 491 mg of Intermediate 32 represented by the following formula.

Chemical formula

[0132] Reference Production Example 5-1 The compounds produced according to Reference Production Example 5 and their physical property values are shown below.

Chemical formula

[0133]

Chemical formula

[0134] Reference Production Example 6 A mixture of 491 mg of Intermediate 32 and 11 mL of triethyl orthoformate was stirred at 100 °C for 1 hour. The resulting mixture was allowed to cool to room temperature and concentrated under reduced pressure. The obtained solid was washed with hexane to obtain 447 mg of Intermediate 35 represented by the following formula.

Chemical formula

[0135] Reference Production Example 6-1 The compound produced according to Reference Production Example 6 and its physical property values are shown below.

Chemical formula

[0136]

Chemical formula

[0137] Reference Production Example 7 The compound produced according to Reference Production Example 3 and its physical property values are shown below.

Chemical Structure

[0138]

Chemical Structure

[0139]

Chemical Structure

[0140] Production Example 1 To a mixture of 1.2 g of Intermediate 1, 0.88 g of cesium carbonate and 6 mL of DMF, 0.51 mL of methyl iodide was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Water was added to the obtained mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane:ethyl acetate = 1:1) to obtain 810 mg of Compound 1 of the present invention.

Chemical formula

[0141] Production Example 1-1 The compounds produced according to Production Example 1 and their physical property values are shown below. Formula (B-1)

Chemical formula

[0142]

Table 5

[0143] In the compound represented by formula (B-1), A 2 , A 3 , A 4 , A 5 , G 4 , R 1 , R 3b and a compound in which the combination of n is any combination described in [Table C-1].

[0144]

Table 6

[0145] Production Example 1 - 2 The compounds produced according to Reference Production Example 3 and their physical property values are shown below. Formula (B - 2)

Chemical formula

[0146]

Table 7

[0147]

Table 8

[0148] Production Example 2 A mixture of 370 mg of Intermediate 2, 580 mg of cesium carbonate, 200 μL of 2-iodopropane and 10 mL of DMF was stirred at 50 °C for 8 hours. Water was added to the obtained mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 5 mL of chloroform was added to the obtained residue, and 400 mg of mCPBA (purity 70%, containing 30% water) was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution were sequentially added to the obtained mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 110 mg of Compound 34 of the present invention.

Chemical Structure

[0149] Production Example 3 To a mixture of 300 mg of Intermediate 38 and 6 mL of THF, 45 mg of sodium borohydride and 0.5 mL of methanol were sequentially added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Water was added to the resulting mixture under ice-cooling, and the precipitated solid was filtered. The obtained solid was washed with water and dried under reduced pressure to obtain 240 mg of Compound 59 of the present invention represented by the following formula. [Chemical formula] Compound 59 of the present invention: 1 H-NMR (CDCl3) δ: 9.02 - 9.01 (1H, m), 8.13 (1H, d), 7.59 - 7.56 (2H, m), 7.18 (1H, d), 7.08 (1H, s), 5.19 (2H, d), 4.77 (1H, br s), 3.64 (2H, q), 1.45 (3H, t).

[0150] Production Example 3-1 The compounds produced according to Production Example 3 and their physical property values are shown below. [Chemical formula] Compound 60 of the present invention: 1 H-NMR (CDCl3) δ: 9.01 - 9.01 (1H, m), 8.28 (1H, s), 7.57 - 7.54 (3H, m), 6.83 (1H, d), 5.21 (2H, d), 5.01 (1H, br s), 3.67 (2H, q), 1.47 (3H, t).

[0151] [Chemical formula] Compound 61 of the present invention: 11H-NMR (CDCl3) δ: 9.09 - 9.09 (1H, m), 7.87 (1H, d), 7.67 (1H, dd), 7.45 (1H, dd), 7.23 - 7.20 (1H, m), 6.81 (1H, d), 5.14 (2H, d), 4.80 (1H, br s), 3.65 (2H, q), 1.47 - 1.43 (3H, m).

[0152] Production Example 4 To a mixture of 150 mg of the compound 60 of the present invention and 3 mL of DMF, 0.2 mL of methyl iodide and 83 mg of potassium carbonate were sequentially added at room temperature, and the mixture was stirred at 80 °C for 16 hours. The resulting mixture was allowed to cool to room temperature, and water was added. The precipitated solid was filtered, and the obtained solid was washed with water and dried under reduced pressure to obtain 102 mg of the compound 62 of the present invention represented by the following formula. [Chemical Formula] Compound 62 of the present invention: 1 1H-NMR (CDCl3) δ: 9.01 (1H, s), 8.30 (1H, d), 7.67 (1H, d), 7.59 - 7.56 (2H, m), 6.84 (1H, d), 5.07 (2H, s), 3.69 (2H, q), 3.07 (3H, s), 1.48 (3H, t).

[0153] Production Example 4-1 The compounds produced according to Production Example 4 and their physical property values are shown below. [Chemical Formula] Compound 63 of the present invention: 1 1H-NMR (CDCl3) δ: 9.01 (1H, s), 8.31 (1H, d), 7.64 (1H, d), 7.58 - 7.57 (2H, m), 6.89 (1H, d), 5.14 (2H, s), 3.68 (2H, q), 3.57 (2H, q), 1.47 (3H, t), 1.28 (3H, t).

[0154] Production Example 5 A mixture of 0.49 g of Compound 7 of the present invention, 260 mg of cyclopropylboronic acid, 150 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), 640 mg of tripotassium phosphate, 4 mL of toluene, and 0.4 mL of water was stirred at 110 °C for 2 hours. After allowing the resulting mixture to cool to room temperature, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (ethyl acetate:hexane = 1:1) to obtain 400 mg of Compound 11 of the present invention represented by the following formula.

Chemical formula

[0155] Production Example 5-1 The compounds produced according to Production Example 5 and their physical property values are shown below.

Chemical formula

[0156]

Chemical formula

[0157] Next, examples of the compound X of the present invention produced according to either the production examples described in the examples or the production methods described in this specification are shown below.

[0158] Formula (L-1) [Chemical formula] In the compound represented by (hereinafter referred to as compound (L-1)), n is 0, R 1 is a methyl group, R 3b is a hydrogen atom, R 3c is a hydrogen atom, and T is a substituent described in any of [Table L1] to [Table L11] (hereinafter referred to as compound group SX1).

[0159] [Table 9]

[0160] [Table 10] TIFF0007704770000074.tif44164

[0161] [Table 11]

[0162] [Table 12]

[0163]

Table 13

Claims

1. Formula (I) 【Chemical 1】 〔wherein Z represents an oxygen atom or a sulfur atom, R １ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group W, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group U, a phenyl group which may be substituted with one or more substituents selected from group V, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group V, C(O)R ５１ , C(O)OR ５１ , or C(O)NR ５１ R ５２ and represents R ５１ and R ５２ are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group V, a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from Group V, or a hydrogen atom, R ２ represents a C1-C6 alkyl group, a cyclopropyl group, or a cyclopropylmethyl group, which may be substituted with one or more halogen atoms, n represents 0, 1 or 2, G １ represents a nitrogen atom or CR ３ａ and G ２ represents a nitrogen atom or CR ３ｂ and G ３ represents a nitrogen atom or CR ３ｃ and G ４ represents a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｂ , R ３ｃ and R ３ｄ are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group E, a phenyl group optionally substituted with one or more substituents selected from group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H, OR １２ , N.R. １１ R １２ , N.R. １１ａ R １２ａ , N.R. ２４ N.R. １１ R １２ , N.R. ２４ OR １１ , N.R. １１ C(O)R １３ , N.R. ２４ N.R. １１ C(O)R １３ , N.R. １１ C(O)OR １４ , N.R. ２４ N.R. １１ C(O)OR １４ , N.R. １１ C(O)NR ３１ R ３２ , N.R. ２４ N.R. １１ C(O)NR ３１ R ３２ , N=CHNR ３１ R ３２ , N=S(O) ｐ R １５ R １６ , C(O)R １３ , C(O)OR １７ , C(O)NR ３１ R ３２ , C(O)NR １１ S (O) ２ R ２３ , C.R. ３０ = NOR １７ , N.R. １１ CR ２４ = NOR １７ , S(O) ｍ R ２３ , represents a cyano group, a nitro group, a hydrogen atom, or a halogen atom, p represents 0 or 1, m represents 0, 1 or 2, R ３０ is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, OR ３５ , NR ３６ R ３７ , or a hydrogen atom, and R ３５ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, R １７ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, or a hydrogen atom, R １１ , R ２４ , R ３６ and R ３７ are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a hydrogen atom, R １２ is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, a C3-C7 cycloalkenyl group which may be substituted with one or more substituents selected from group J, a phenyl group which may be substituted with one or more substituents selected from group D, a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group D, a hydrogen atom, or S(O) ２ R ２３ represents, R ２３ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from Group D, R １１ａ and R １２ａ together with the nitrogen atom to which they are attached, form a 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group E R １３ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, or a hydrogen atom, and R １４ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may be substituted with one or more substituents selected from Group D}, R １５ and R １６ are the same or different and each represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, R ３１ represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R ３２ is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, S(O) ２ R ２３ , or represents a hydrogen atom, A １ represents a nitrogen atom or CR ４ａ and A ２ represents a nitrogen atom or CR ４ｂ and A ３ represents a nitrogen atom or CR ４ｃ and A ４ represents a nitrogen atom or CR ４ｄ and A ５ represents a nitrogen atom or CR ４ｅ (provided that not all of A ２ , A ３ and A ４ represent nitrogen atoms). R ４ａ and R ４ｅ are the same or different and are each independently a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group Y, a phenyl group optionally substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group optionally substituted with one or more substituents selected from group Z, OR ４４ , S(O) ｋ R ４１ , S(O) ２ NR ４１ R ４２ , NR ４１ R ４３ , NR ４１ C(O)R ４２ , NR ４１ C(O)OR ４２ , NR ４１ S(O) ２ R ４３ , C(O)R ４１ , C(O)OR ４１ , C(O)NR ４１ R ４２ , CR ４２ =NOR ４１ , represent a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom, A ５ is CR ４ｅ in the case where, R ４ｅ and R １ together form -NR ４５ -CR ４１ R ４２ -# may be formed {# represents the bonding position with the nitrogen atom to which R １ is bonded}, R ４ｂ 、R ４ｃ and R ４ｄ are the same or different and may be a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group Y, a phenyl group optionally substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group optionally substituted with one or more substituents selected from group Z, OR ４４ , S(O) ｑ R ４１ , S(O) ２ NR ４１ R ４２ , NR ４１ R ４２ , NR ４１ C(O)R ４２ , NR ４１ C(O)OR ４２ , NR ４１ S(O) ２ R ４３ , C(O)R ４１ , C(O)OR ４１ , C(O)NR ４１ R ４２ , CR ４２ =NOR ４１ , a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom (provided that not all of the existing R ４ａ , R ４ｂ , R ４ｃ , R ４ｄ , and R ４ｅ represent hydrogen atoms), k represents 0, 1 or 2 q represents 0, 1 or 2, R ４１ and R ４２ are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group Z, or a hydrogen atom, R ４３ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group Z, or a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group Z, R ４４ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, R ４５ is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group W ２ , a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group Y, a phenyl group which may be substituted with one or more substituents selected from group Z, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group Z, C(O)R ４６ , C(O)OR ４６ , C(O)NR ４６ R ４７ , or represents a hydrogen atom, R ４６ and R ４７ are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group Z, or a hydrogen atom. Group B: a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom. Group C: a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, and a halogen atom. Group D: a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR ２１ , NR ２１ R ２２ , C(O)R ２１ , OC(O)R ２１ , C(O)OR ２１ , a cyano group, a nitro group, and a group consisting of halogen atoms. R ２１ and R ２２ represent a C1-C6 alkyl group which may be the same or different and which may be substituted by one or more halogen atoms. Group E: a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group. Group F: a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from Group C, an amino group, NHR ２１ , NRR ２１ R ２２ , a group consisting of a halogen atom and a cyano group. Group H: a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, OR １０ , NR ９ R １０ , C(O)R １０ , C(O)NR ９ R １０ , OC(O)R ９ , OC(O)OR ９ , NR １０ C(O)R ９ , NR １０ C(O)OR ９ , C(O)OR １０ , the group consisting of a halogen atom, a nitro group, a cyano group, and an amino group. R ９ represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, R １０ represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. Group J: a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group. Group U: a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, and a halogen atom. Group V: a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylamino group which may be substituted with one or more halogen atoms, a di(C1-C6 alkyl which may be substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. Group W: a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group Z, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group Z, a hydroxy group, a cyano group, and a halogen atom. Group X: A C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom. Group Y: A C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, and a halogen atom. Group Z: A C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl optionally substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. Group W ２ : A C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group Z, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group Z, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom.] The compound represented by or its N-oxide.

2. R ４５ is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group X, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group Y, a phenyl group which may be substituted with one or more substituents selected from group Z, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group Z, C(O)R ４６ , C(O)OR ４６ , C(O)NR ４６ R ４７ , or a hydrogen atom, the compound or its N-oxide according to claim 1.

3. G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ The compound or its N-oxide according to claim 1 or claim 2

4. A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is a nitrogen atom or CR ４ｃ and A ４ is a nitrogen atom or CR ４ｄ and A ５ is a nitrogen atom or CR ４ｅ The compound according to any one of claims 1 to 3 or an N-oxide thereof.

5. A １ 、 A ２ 、 A ３ 、 A ４ and A ５ 's combination is A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is CR ４ｃ and A ４ is CR ４ｄ and A ５ is CR ４ｅ a combination; A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is a nitrogen atom, and A ４ is CR ４ｄ and A ５ is CR ４ｅ a combination; A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is CR ４ｃ and A ４ is a nitrogen atom, and A ５ is CR ４ｅ is a combination; or A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is CR ４ｃ and A ４ is CR ４ｄ and A ５ is a combination in which A is a nitrogen atom, the compound according to any one of claims 1 to 3 or an N-oxide thereof.

6. A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is CR ４ｃ and A ４ is CR ４ｄ and A ５ is CR ４ｅ is, a compound according to any one of claims 1 to 3 or an N-oxide thereof.

7. G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and A １ is CR ４ａ and A ２ is CR ４ｂ and A ３ is CR ４ｃ and A ４ is CR ４ｄ and A ５ is CR ４ｅ is the compound or its N-oxide according to claim 1 or claim 2.

8. R ２ The compound or its N-oxide according to any one of claims 1 to 7, wherein R is an ethyl group.

9. The compound according to any one of Claims 1 to 8 or its N-oxide, wherein Z is an oxygen atom.

10. A pest arthropod control composition containing the compound according to any one of Claims 1 to 9 or an N-oxide thereof.

11. A composition containing one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound according to any one of Claims 1 to 9 or an N-oxide thereof: Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient; Group (b): a bactericidal active ingredient; Group (c): a plant growth regulating ingredient; Group (d): a repellent ingredient.

12. A method for controlling pest arthropods, which comprises applying an effective amount of the compound according to any one of Claims 1 to 9 or an N-oxide thereof or an effective amount of the composition according to Claim 11 to the pest arthropods or the habitat of the pest arthropods (however, excluding a method for treating humans).

13. Seeds or vegetative reproductive organs holding an effective amount of the compound according to any one of Claims 1 to 9 or an N-oxide thereof or an effective amount of the composition according to Claim 11.

14. Formula (II) 【Chemical 2】 〔In the formula, Z represents an oxygen atom or a sulfur atom, R ２ represents a C1-C6 alkyl group, a cyclopropyl group, or a cyclopropylmethyl group which may be substituted with one or more halogen atoms, n represents 0, 1 or 2, G １ represents a nitrogen atom or CR ３ａ and G ２ represents a nitrogen atom or CR ３ｂ and G ３ represents a nitrogen atom or CR ３ｃ and G ４ represents a nitrogen atom or CR ３ｄ and R ３ａ 、R ３ｂ 、R ３ｃ and R ３ｄ are the same or different and may be substituted with one or more substituents selected from Group B, a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group E, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from Group H, a phenyl group which may be substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group H, OR １２ 、NR １１ R １２ 、NR １１ａ R １２ａ 、NR ２４ NR １１ R １２ 、NR ２４ OR １１ 、NR １１ C(O)R １３ 、NR ２４ NR １１ C(O)R １３ 、NR １１ C(O)OR １４ 、NR ２４ NR １１ C(O)OR １４ 、NR １１ C(O)NR ３１ R ３２ 、NR ２４ NR １１ C(O)NR ３１ R ３２ 、N=CHNR ３１ R ３２ 、N=S(O) ｐ R １５ R １６ 、C(O)R １３ 、C(O)OR １７ 、C(O)NR ３１ R ３２ 、C(O)NR １１ S(O) ２ R ２３ 、CR ３０ =NOR １７ 、NR １１ CR ２４ =NOR １７ 、S(O) ｍ R ２３ , represents a cyano group, a nitro group, a hydrogen atom, or a halogen atom, p represents 0 or 1, m represents 0, 1 or 2, R ３０ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, OR ３５ , NR ３６ R ３７ , or a hydrogen atom, and R ３５ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, R １７ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, or a hydrogen atom, R １１ 、R ２４ 、R ３６ and R ３７ are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a hydrogen atom, R １２ is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, a C3-C7 cycloalkenyl group which may be substituted with one or more substituents selected from group J, a phenyl group which may be substituted with one or more substituents selected from group D, a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group D, a hydrogen atom, or S(O) ２ R ２３ represents, R ２３ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from Group D, R １１ａ and R １２ａ together with the nitrogen atom to which they are attached, form a 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group E, R １３ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, or a hydrogen atom, R １４ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may be substituted with one or more substituents selected from Group D}, R １５ and R １６ which are the same or different and each represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, R ３１ represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R ３２ is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, S(O) ２ R ２３ , or represents a hydrogen atom, A １ represents a nitrogen atom or CR ４ａ and A ２ represents a nitrogen atom or CR ４ｂ and A ３ represents a nitrogen atom or CR ４ｃ and A ４ represents a nitrogen atom or CR ４ｄ and A ５ represents a nitrogen atom or CR ４ｅ (provided that not all of A ２ , A ３ and A ４ represent nitrogen atoms). R ４ａ and R ４ｅ are the same or different and are each independently a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group X, a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from group Y, a phenyl group which may be substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group Z, OR ４４ 、S(O) ｋ R ４１ 、S(O) ２ NR ４１ R ４２ 、NR ４１ R ４３ 、NR ４１ C(O)R ４２ 、NR ４１ C(O)OR ４２ 、NR ４１ S(O) ２ R ４３ 、C(O)R ４１ 、C(O)OR ４１ 、C(O)NR ４１ R ４２ 、CR ４２ =NOR ４１ 、represent a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom, R ４ｂ 、R ４ｃ and R ４ｄ are the same or different and may be a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group Y, a phenyl group optionally substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group optionally substituted with one or more substituents selected from group Z, OR ４４ , S(O) ｑ R ４１ , S(O) ２ NR ４１ R ４２ , NR ４１ R ４２ , NR ４１ C(O)R ４２ , NR ４１ C(O)OR ４２ , NR ４１ S(O) ２ R ４３ , C(O)R ４１ , C(O)OR ４１ , C(O)NR ４１ R ４２ , CR ４２ =NOR ４１ , a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom (provided that not all of the existing R ４ａ , R ４ｂ , R ４ｃ , R ４ｄ , and R ４ｅ represent hydrogen atoms), k represents 0, 1 or 2 q represents 0, 1 or 2, R ４１ and R ４２ are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group Z, a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group Z, or a hydrogen atom, R ４３ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group Z, or a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group Z, R ４４ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. Group B: a group consisting of a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom. Group C: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, and a halogen atom. Group D: a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR ２１ , NR ２１ R ２２ , C(O)R ２１ , OC(O)R ２１ , C(O)OR ２１ , a cyano group, a nitro group, and a group consisting of halogen atoms R ２１ and R ２２ are the same or different and each represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms. Group E: A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group. Group F: a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from Group C, an amino group, NHR ２１ , NR ２１ R ２２ , a group consisting of a halogen atom and a cyano group. Group H: a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, OR １０ , NR ９ R １０ , C(O)R １０ , C(O)NR ９ R １０ , OC(O)R ９ , OC(O)OR ９ , NR １０ C(O)R ９ , NR １０ C(O)OR ９ , C(O)OR １０ , the group consisting of a halogen atom, a nitro group, a cyano group, and an amino group. R ９ represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, R １０ represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. Group J: A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group. Group X: A C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom. Group Y: A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, and a halogen atom. Group Z: a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylamino group which may be substituted with one or more halogen atoms, a di(C1-C6 alkyl which may be substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. The compound represented by the formula or a salt thereof.

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