Aryltetrahydropyridine compound and pest control agent

Abstract

The present invention relates to an aryltetrahydropyridine compound represented by formula (1) or a salt thereof. [In formula (1), Q represents Q-1, etc.; J represents J-1, etc.; G represents G-1, etc.; R1 represents a halo(C1-C6)alkyl, etc.; R2 represents a hydrogen atom, etc.; R3 represents a hydrogen atom, etc.; X represents an oxygen atom, etc.; Y represents an oxygen atom, etc.; and A1 represents a nitrogen atom, etc.]

Description

Aryltetrahydropyridine compounds and pest control agents

[0001] The present invention relates to novel aryltetrahydropyridine compounds and salts thereof, production intermediates thereof, and pest control agents, agricultural chemicals, control agents, insecticides or miticides, seed treatment agents and soil treatment agents each containing the compound and / or its salt as an active ingredient.

[0002] Certain aryltetrahydropyridine compounds are known to exhibit pesticidal activity (see, for example, Patent Documents 1 and 2).

[0003] International Publication No. 2021 / 261562 International Publication No. 2023 / 127806

[0004] However, long-term use of insecticides can lead to the emergence of pests and harmful organisms that have acquired resistance to existing insecticides, and therefore there is a constant demand for the development of new pesticides with excellent pest control effects.

[0005] The present inventors have conducted extensive research aimed at solving the above problems, and as a result have found that the novel aryltetrahydropyridine compounds according to the present invention, represented by the following formula (1), exhibit excellent pest control activity, particularly excellent insecticidal and acaricidal activity, and have thus completed the present invention.

[0006] That is, the present invention relates to an aryltetrahydropyridine compound represented by the following formula (1) or a salt thereof. Formula (1): [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-2 9, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56; Z１ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, halo (C ２ ~C ６ ) alkenyl, halo(C ２ ~C ６ ) alkynyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkoxy (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkenyloxy, halo(C ２ ~C ６ ) alkenyloxy, C ２ ~C ６ Alkynyloxy, halo(C ２ ~C ６ ) alkynyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, C ２ ~C ６ Alkenylthio, C ２ ~C ６ Alkenylsulfinyl, C ２ ~C ６ Alkenylsulfonyl, halo(C ２ ~C ６ ) alkenylthio, halo(C ２ ~C ６ ) alkenylsulfinyl, halo(C２ ~C ６ ) alkenylsulfonyl, C ２ ~C ６ Alkynylthio, C ２ ~C ６ Alkynylsulfinyl, C ２ ~C ６ Alkynylsulfonyl, halo(C ２ ~C ６ ) alkynylthio, halo(C ２ ~C ６ ) alkynylsulfinyl, halo(C ２ ~C ６ ) alkynylsulfonyl, —NH ２ , C １ ~C ６ Alkylamino, di(C １ ~C ６ ) alkylamino, halo(C １ ~C ６ ) alkylamino, dihalo (C １ ~C ６ ) alkylamino, formyl, carboxy, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, halo(C １ ~C ６ ) alkoxycarbonyl, C １ ~C ６ alkylaminocarbonyl, halo(C １ ~C ６ ) alkylaminocarbonyl, di(C １ ~C ６ ) alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkoxycarbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo(C １ ~C ６ ) alkylsulfonyloxy, —SO ３ H, C １ ~C ６Alkylaminosulfonyl, di(C １ ~C ６ ) alkylaminosulfonyl, —C(═NOR １２ ) R １３ , cyano or nitro; R １２ is a hydrogen atom or C １ ~C ６ represents alkyl, R １３ is a hydrogen atom or C １ ~C ６ represents alkyl; Z ３ is a hydrogen atom or C １ ~C ６ alkyl, J represents J-1 or J-2, A １ represents a nitrogen atom or CH, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G- 32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-4 7, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, halo (C ２ ~C ６ ) alkenyl, halo(C ２ ~C ６ ) alkynyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C１ ~C ６ Alkoxy (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkenyloxy, halo(C ２ ~C ６ ) alkenyloxy, C ２ ~C ６ Alkynyloxy, halo(C ２ ~C ６ ) alkynyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, C ２ ~C ６ Alkenylthio, C ２ ~C ６ Alkenylsulfinyl, C ２ ~C ６ Alkenylsulfonyl, halo(C ２ ~C ６ ) alkenylthio, halo(C ２ ~C ６ ) alkenylsulfinyl, halo(C ２ ~C ６ ) alkenylsulfonyl, C ２ ~C ６ Alkynylthio, C ２ ~C ６ Alkynylsulfinyl, C ２ ~C ６ Alkynylsulfonyl, halo(C ２ ~C ６ ) alkynylthio, halo(C ２ ~C ６ ) alkynylsulfinyl, halo(C ２ ~C ６ ) alkynylsulfonyl, —NH ２ , C １ ~C６ Alkylamino, di(C １ ~C ６ ) alkylamino, halo(C １ ~C ６ ) alkylamino, dihalo (C １ ~C ６ ) alkylamino, formyl, carboxy, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, halo(C １ ~C ６ ) alkoxycarbonyl, C １ ~C ６ alkylaminocarbonyl, halo(C １ ~C ６ ) alkylaminocarbonyl, di(C １ ~C ６ ) alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkoxycarbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo(C １ ~C ６ ) alkylsulfonyloxy, —SO ３ H, C １ ~C ６ Alkylaminosulfonyl, di(C １ ~C ６ ) alkylaminosulfonyl, —C(═NOR １４ ) R １５ , nitro or cyano; R １４ is a hydrogen atom or C １ ~C ６ represents alkyl, R １５ is a hydrogen atom or C １ ~C ６ represents alkyl; Z ４ is C １ ~C ６ represents alkyl, R １ represents a hydrogen atom, a halogen atom, a halo (C１ ~C ６ ) alkyl, C １ ~C ６ represents alkyl or cyano; R ２ is a hydrogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ cycloalkyl, —C(O)R ４ , -C(O)OR ５ , D-1, D-2 or D-3; R ４ is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkylcarbonyl, di(C １ ~C ６ ) alkylamino or R ６ (C １ ~C ６ ) alkyl, R ６ is a halogen atom, C １ ~C ６ Alkoxy, cyano, nitro, phenyl or R ８ represents phenyl substituted with ５ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R ８ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R ５ is C １ ~C６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, R ９ (C １ ~C ６ ) alkyl, phenyl or R １０ represents phenyl substituted with R ９ is a halogen atom, C １ ~C ６ Alkoxy, cyano, nitro, phenyl or R １１ represents phenyl substituted with R １０ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R １１ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R ３ is a hydrogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl or C １ ~C ６ represents an alkylcarbonyl, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, t5 represents an integer of 0, 1, 2, 3, 4 or 5, and t8 represents an integer of 0, 1, 2, 3 or 4.

[0007] The compounds of the present invention represented by formula (1) exhibit excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, and internal or external parasites of mammals or birds. Therefore, the present invention can provide novel aryltetrahydropyridine compounds or salts thereof that are useful as pest control agents, particularly as insecticides.

[0008] In the compound according to the present invention represented by formula (1) (hereinafter also referred to as "the compound of the present invention"), tautomers represented by the following formulas are considered to exist, and the compound of the present invention represented by formula (1) includes all tautomers or a mixture of tautomers containing all tautomers in any ratio.

[0009]

[0010] The compound of the present invention may exist as E- and Z-geometric isomers depending on the types of substituents, and the compound of the present invention includes a mixture containing these E-, Z-, or E- and Z-isomers in any ratio.

[0011] Furthermore, the compound of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and the compound of the present invention includes all optically active forms and racemic forms.

[0012] Furthermore, the compound of the present invention may have tautomers depending on the type of substituent, and the compound of the present invention includes all tautomers or a mixture of tautomers containing all tautomers in any ratio.

[0013] Furthermore, the compound of the present invention may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, and the compound of the present invention encompasses all rotational isomers or a mixture of diastereomers containing all rotational isomers in any ratio.

[0014] Among the compounds of the present invention, those which can be converted into salts by a conventional method include salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; aluminum salts; and quaternary ammonium salts such as tetramethylammonium salt, tetrabutylammonium salt, and benzyltrimethylammonium salt.

[0015] Next, specific examples of the substituents shown in this specification are shown below, where n- means normal, i- means iso, s- means secondary, and tert- means tertiary.

[0016] As used herein, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the term "halo" used herein also represents these halogen atoms.

[0017] In this specification, "C ａ ~C ｂ The term "alkyl" refers to a linear or branched hydrocarbon group having a to b carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl, each of which is selected within the range of the number of carbon atoms specified.

[0018] As used herein, "halo(C ａ ~C ｂThe expression "alkyl" refers to a linear or branched hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when the alkyl group is substituted with two or more halogen atoms, the halogen atoms may be the same or different from one another. Examples of the alkyl group include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-difluoro Specific examples include propyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1-(methyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, and the like, and the number of carbon atoms is selected within the range specified for each.

[0019] In this specification, "C ａ ~C ｂ The term "alkenyl" refers to a linear or branched unsaturated hydrocarbon group containing a to b carbon atoms and having one or more double bonds in the molecule, and specific examples thereof include vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, and 1,1-dimethyl-2-propenyl, and each of these groups is selected within the range of the number of carbon atoms specified.

[0020] As used herein, "halo(C ａ ~C ｂ The term "(a) alkenyl" refers to a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and one or more double bonds in the molecule, in which hydrogen atoms bonded to carbon atoms are optionally substituted with halogen atoms. In this case, when the alkenyl group is substituted with two or more halogen atoms, the halogen atoms may be the same or different. Specific examples include 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, 2,3,3-trichloro-2-propenyl, 1-(trifluoromethyl)ethenyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, and 3-chloro-4,4,4-trifluoro-2-butenyl, and the like, each of which is selected within the range of the number of carbon atoms specified for each.

[0021] In this specification, "C ａ ~C ｂ The term "alkynyl" refers to a linear or branched unsaturated hydrocarbon group containing a to b carbon atoms and having one or more triple bonds in the molecule, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl, each selected from within the range of the number of carbon atoms specified.

[0022] As used herein, "halo(C ａ ~C ｂThe term "alkynyl" refers to a linear or branched unsaturated hydrocarbon group having a to b carbon atoms, in which hydrogen atoms bonded to carbon atoms are optionally substituted with halogen atoms, and which has one or more triple bonds in the molecule. In this case, when the alkynyl group is substituted with two or more halogen atoms, the halogen atoms may be the same or different. Specific examples include 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, and 3-iodo-2-propynyl, and each group may be selected within the range of the number of carbon atoms specified.

[0023] In this specification, "C ａ ~C ｂ The term "alkoxy" represents an alkyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, and 2-ethylhexyloxy, and each group is selected within the range of the number of carbon atoms specified.

[0024] As used herein, "halo(C ａ ~C ｂ The notation of "(a) alkoxy" represents a haloalkyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropyloxy, and the like, each selected within the range of the specified number of carbon atoms.

[0025] In this specification, "C ａ ~C ｂ Alkoxy (C ｄ ~C ｅ The notation "alkoxy" refers to any C-alkoxy group having the above-mentioned meaning. ａ ~C ｂThe alkoxy group represents an alkoxy group having d to e carbon atoms in which a hydrogen atom bonded to the carbon atom is optionally substituted, and specific examples thereof include methoxymethoxy and 2-methoxyethoxy, each of which is selected within the range of the number of carbon atoms specified.

[0026] In this specification, "C ａ ~C ｂ The term "alkenyloxy" represents an alkenyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include 2-propenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, and 3-methyl-2-butenyloxy, each selected from the range of the number of carbon atoms specified.

[0027] As used herein, "halo(C ａ ~C ｂ The notation of "haloalkenyloxy" represents a haloalkenyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include 3,3-difluoroallyloxy and 3,3-dichloroallyloxy, and the number of carbon atoms is selected within the range specified for each group.

[0028] In this specification, "C ａ ~C ｂ The term "alkynyloxy" represents an alkynyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include ethynyloxy, propargyloxy, 2-butynyloxy, 1-pentynyloxy, and 1-hexynyloxy, each selected from the range of the number of carbon atoms specified.

[0029] As used herein, "halo(C ａ ~C ｂ The notation of ")alkynyloxy" represents a haloalkynyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, and 3-iodo-2-propynyloxy, and the like, each selected within the range of the number of carbon atoms specified.

[0030] In this specification, "C ａ ~C ｂThe term "alkylthio" represents an alkyl-S- group having a to b carbon atoms as defined above, and specific examples thereof include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio, each of which is selected within the range of the number of carbon atoms specified.

[0031] As used herein, "halo(C ａ ~C ｂ The notation of "(trifluoromethyl)alkylthio" represents a haloalkyl-S- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio, and nonafluorobutylthio, and the like are selected within the range of the number of carbon atoms specified for each group.

[0032] In this specification, "C ａ ~C ｂ The term "alkenylthio" represents an alkenyl-S- group having a to b carbon atoms as defined above, and specific examples thereof include 2-propenylthio, 2-butenylthio, 2-methyl-2-propenylthio, and 3-methyl-2-butenylthio, each selected from the range of the number of carbon atoms specified.

[0033] As used herein, "halo(C ａ ~C ｂThe notation of ")alkenylthio" represents a haloalkenyl-S- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 2-fluoro-2-propenylthio, 2-chloro-2-propenylthio, 3,3-difluoro-2-propenylthio, 3,3-dichloro-2-propenylthio, 2,3,3-trifluoro-2-propenylthio, 4,4-difluoro-3-butenylthio, and 3,4,4-trifluoro-3-butenylthio, and the like, each selected within the range of the specified number of carbon atoms.

[0034] In this specification, "C ａ ~C ｂ The term "alkynylthio" represents an alkynyl-S- group having a to b carbon atoms as defined above, and specific examples thereof include propynylthio, butynylthio, pentynylthio, and hexynylthio, each selected from the range of the number of carbon atoms specified.

[0035] As used herein, "halo(C ａ ~C ｂ The notation of ")alkynylthio" represents a haloalkynyl-S- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 3-chloro-2-propynylthio, 3-bromo-2-propynylthio, and 3-iodo-2-propynylthio, and the like, each selected from the range of the specified number of carbon atoms.

[0036] In this specification, "C ａ ~C ｂ The term "alkylsulfinyl" represents an alkyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl, and the like, selected within the range of the number of carbon atoms specified for each group.

[0037] As used herein, "halo(C ａ ~C ｂThe notation of "(1-(trifluoromethyl)alkylsulfinyl)" represents a haloalkyl-S(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl, nonafluorobutylsulfinyl, and the like, and is selected within the range of the number of carbon atoms specified for each group.

[0038] In this specification, "C ａ ~C ｂ The term "alkenylsulfinyl" represents an alkenyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include 2-propenylsulfinyl, 2-butenylsulfinyl, 2-methyl-2-propenylsulfinyl, and 3-methyl-2-butenylsulfinyl, each selected from the range of the number of carbon atoms specified.

[0039] As used herein, "halo(C ａ ~C ｂ The notation of "haloalkenylsulfinyl" represents a haloalkenyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include 2-fluoro-2-propenylsulfinyl, 2-chloro-2-propenylsulfinyl, 3,3-difluoro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4,4-difluoro-3-butenylsulfinyl, and 3,4,4-trifluoro-3-butenylsulfinyl, and the like, each selected within the range of the specified number of carbon atoms.

[0040] In this specification, "C ａ ~C ｂ The term "alkynylsulfinyl" represents an alkynyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include 2-propynylsulfinyl and 2-butynylsulfinyl, each selected from within the range of the number of carbon atoms specified.

[0041] As used herein, "halo(C ａ~C ｂ The notation of "haloalkynylsulfinyl" represents a haloalkynyl-S(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, and 3-iodo-2-propynylsulfinyl, and the like, each selected from within the range of the specified number of carbon atoms.

[0042] In this specification, "C ａ ~C ｂ The expression "alkylsulfonyl" means alkyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. ２ - group, and specific examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, etc., and each is selected within the range of the number of carbon atoms specified.

[0043] As used herein, "halo(C ａ ~C ｂ The expression "alkylsulfonyl" refers to the haloalkyl-SO 3 group having the above-mentioned meaning and containing a to b carbon atoms. ２ - group, and specific examples include difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trifluoroethylsulfonyl, and the like, and each is selected within the range of the number of carbon atoms specified.

[0044] In this specification, "C ａ ~C ｂ The expression "alkenylsulfonyl" means the alkenyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. ２ - group, and specific examples include 2-propenylsulfonyl, 2-butenylsulfonyl, 2-methyl-2-propenylsulfonyl, 3-methyl-2-butenylsulfonyl, etc., and each group is selected within the range of the number of carbon atoms specified.

[0045] As used herein, "halo(Cａ ~C ｂ The notation "haloalkenylsulfonyl" means the haloalkenyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. ２ - group, and specific examples include 2-fluoro-2-propenylsulfonyl, 2-chloro-2-propenylsulfonyl, 3,3-difluoro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl, and 3,4,4-trifluoro-3-butenylsulfonyl, and the number of carbon atoms is selected within the range specified for each group.

[0046] In this specification, "C ａ ~C ｂ The expression "alkynylsulfonyl" means an alkynyl-SO 3 group having the above-mentioned meaning and containing a to b carbon atoms. ２ Specific examples include 2-propynylsulfonyl and 2-butynylsulfonyl, and each is selected within the range of the number of carbon atoms specified.

[0047] As used herein, "halo(C ａ ~C ｂ The notation "alkynylsulfonyl" means haloalkynyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. ２ Specific examples include 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl, 3-iodo-2-propynylsulfonyl, and the like, and each is selected within the range of the number of carbon atoms specified.

[0048] In this specification, "C ａ ~C ｂ The term "alkylamino" refers to an amino group in which one of the hydrogen atoms is substituted with alkyl having a to b carbon atoms as defined above, and specific examples thereof include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino, each selected within the range of the number of carbon atoms specified.

[0049] As used herein, "halo(C ａ ~C ｂThe expression "a) alkylamino" represents an amino group in which one of the hydrogen atoms is substituted by haloalkyl having a to b carbon atoms as defined above, and specific examples thereof include 2,2,2-trifluoroethylamino, 2-chloro-2,2-difluoroethylamino, and 3,3,3-trifluoropropylamino, each selected within the range of the number of carbon atoms specified.

[0050] In this specification, "di(C ａ ~C ｂ The expression "alkylamino" refers to an amino group in which both hydrogen atoms are substituted with alkyl as defined above, which may be the same or different and have a to b carbon atoms. Specific examples include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., and the number of carbon atoms is selected within the range specified for each group.

[0051] As used herein, "dihalo(C ａ ~C ｂ The expression "(2,2,2-trifluoroethyl)amino" refers to an amino group in which both hydrogen atoms are substituted with haloalkyl as defined above, which may be the same or different and have a to b carbon atoms, and specific examples include bis(2,2,2-trifluoroethyl)amino, and the number of carbon atoms is selected within the range specified for each group.

[0052] In this specification, "C ａ ~C ｂ The term "cycloalkyl" refers to a cyclic saturated hydrocarbon group having a to b carbon atoms, which can form a single ring or multiple ring structures having 3 to 10 members. Each ring may be optionally substituted with alkyl within the specified range of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each of which is selected within the specified range of carbon atoms.

[0053] In this specification, "Cａ ~C ｂ The term "alkylcarbonyl" represents an alkyl-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanoyl, each of which is selected within the range of the number of carbon atoms specified.

[0054] As used herein, "halo(C ａ ~C ｂ The notation of "haloalkylcarbonyl" represents a haloalkyl-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, heptafluorobutanoyl, and 3-chloro-2,2-dimethylpropanoyl, and the like are selected within the range of the number of carbon atoms specified for each group.

[0055] In this specification, "C ａ ~C ｂ The term "alkoxycarbonyl" represents an alkyl-O-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl, and the number of carbon atoms is selected within the range specified for each group.

[0056] As used herein, "halo(C ａ ~C ｂThe notation of ")alkoxycarbonyl" represents a haloalkyl-O-C(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include chloromethoxycarbonyl, 2-chloroethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, and 2,2,2-trichloroethoxycarbonyl, and the like are selected within the range of the number of carbon atoms specified for each group.

[0057] In this specification, "C ａ ~C ｂ The term "alkylaminocarbonyl" represents a carbamoyl group in which one of the hydrogen atoms is substituted with alkyl having a to b carbon atoms as defined above, and specific examples thereof include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, and tert-butylcarbamoyl, each selected from the range of the number of carbon atoms specified.

[0058] As used herein, "halo(C ａ ~C ｂ The notation of ") alkylaminocarbonyl" represents a carbamoyl group in which one of the hydrogen atoms is substituted by the above-mentioned haloalkyl having a to b carbon atoms, and specific examples thereof include 2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluoroethylcarbamoyl, and 2,2,2-trifluoroethylcarbamoyl, and the like are selected within the range of the number of carbon atoms specified for each group.

[0059] In this specification, "di(C ａ ~C ｂ The expression "(a) alkylaminocarbonyl" represents a carbamoyl group in which both hydrogen atoms are substituted with alkyl as defined above, each of which may be the same or different and has a to b carbon atoms. Specific examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, and N,N-di(n-butyl)carbamoyl, and are selected within the range of the number of carbon atoms specified for each group.

[0060] In this specification, "C ａ ~C ｂ The term "alkylcarbonyloxy" refers to an alkyl-C(O)-O- group having a to b carbon atoms as defined above. Specific examples include acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, etc., and each group is selected within the range of the number of carbon atoms specified.

[0061] In this specification, "C ａ ~C ｂ The term "alkoxycarbonyloxy" represents an alkoxy-C(O)-O- group having a to b carbon atoms as defined above, and specific examples thereof include methoxycarbonyloxy, ethoxycarbonyloxy, i-butyloxycarbonyloxy, and tert-butyloxycarbonyloxy, and the like are selected within the range of the number of carbon atoms specified for each group.

[0062] In this specification, "C ａ ~C ｂ The term "alkylsulfonyloxy" represents an alkylsulfonyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, and i-propylsulfonyloxy, and the like are selected within the range of the number of carbon atoms specified for each group.

[0063] As used herein, "halo(C ａ ~C ｂ The notation of "haloalkylsulfonyloxy" represents a haloalkylsulfonyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include difluoromethylsulfonyloxy, trifluoromethylsulfonyloxy, chlorodifluoromethylsulfonyloxy, bromodifluoromethylsulfonyloxy, and the like, and each group is selected within the range of the number of carbon atoms specified.

[0064] In this specification, "C ａ ~C ｂThe term "alkylaminosulfonyl" refers to a sulfamoyl group in which one of the hydrogen atoms is substituted with alkyl having a to b carbon atoms as defined above, and specific examples thereof include methylsulfamoyl, ethylsulfamoyl, n-propylsulfamoyl, i-propylsulfamoyl, n-butylsulfamoyl, i-butylsulfamoyl, s-butylsulfamoyl, and tert-butylsulfamoyl, each selected within the range of the specified number of carbon atoms.

[0065] In this specification, "di(C ａ ~C ｂ The expression "(a) alkylaminosulfonyl" represents a sulfamoyl group in which both hydrogen atoms are substituted with alkyl as defined above, which may be the same or different and have a to b carbon atoms, and specific examples thereof include N,N-dimethylsulfamoyl, N-ethyl-N-methylsulfamoyl, N,N-diethylsulfamoyl, N,N-di(n-propyl)sulfamoyl, and N,N-di(n-butyl)sulfamoyl, and the like are selected within the range of the number of carbon atoms specified for each group.

[0066] In this specification, "C ａ ~C ｂ The term "cycloalkylcarbonyl" represents a cycloalkyl-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include cyclopropylcarbonyl, 2-methylcyclopropylcarbonyl, and cyclobutylcarbonyl, each selected from the range of the number of carbon atoms specified.

[0067] As used herein, "halo(C ａ ~C ｂ The notation of "halocycloalkylcarbonyl" represents a halocycloalkyl-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include 2,2-dichlorocyclopropylcarbonyl and 2,2-dichloro-1-methylcyclopropylcarbonyl, and the number of carbon atoms is selected within the range specified for each group.

[0068] In this specification, "R ６ (C ａ~C ｂ The notation "alkyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R ６ represents an alkyl group having the above-mentioned meaning and having a to b carbon atoms, which is partially or completely substituted with the following, and the number of carbon atoms is selected within the range specified for each group. ６ When two or more groups are present, the substituent R ６ may be the same or different from each other.

[0069] In this specification, "R ８ The notation "phenyl substituted with" means that any hydrogen atom attached to the carbon atom is substituted with one or more substituents R ８ In this case, the substituent R ８ When two or more groups are present, the substituent R ８ may be the same or different from each other.

[0070] In this specification, "R ９ (C ａ ~C ｂ The notation "alkyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R ９ represents an alkyl group having the above-mentioned meaning and having a to b carbon atoms, which is partially or completely substituted with the following, and the number of carbon atoms is selected within the range specified for each group. ９ When two or more groups are present, the substituent R ９ may be the same or different from each other.

[0071] In this specification, "R １０ The notation "phenyl substituted with" means that any hydrogen atom attached to the carbon atom is substituted with one or more substituents R １０ In this case, the substituent R １０ When two or more groups are present, the substituent R １０ may be the same or different from each other.

[0072] In this specification, "R １１ The notation "phenyl substituted with" means that any hydrogen atom attached to the carbon atom is substituted with one or more substituents R １１ In this case, the substituent R１１ When two or more groups are present, the substituent R １１ may be the same or different from each other.

[0073] Next, a method for producing the compound of the present invention represented by formula (1) will be described below. The compound of the present invention can be produced, for example, by the following method. Note that the following description is merely illustrative, and the compound of the present invention represented by formula (1) may also be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" will also be described as "compound (1) of the present invention," and "compound represented by formula (2)" will also be described as "compound (2)." Other compounds will also be described in a similar manner.

[0074] [Production Method 1] The compound (1) of the present invention can be produced by reacting the compound (2) with the compound (3). (In the formula, Ja represents Ja-1 or Ja-2, J, Q, G, X, Y, A １ , R １ , R ２ and R ３ represents the same meaning as above, Ga represents a halogen atom or the like, and Gb represents B(OH) ２ etc.)

[0075] The compound (1) of the present invention can be produced by reacting the compound (2) with the compound (3) in a solvent or without a solvent.

[0076] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include water, alcohol solvents such as methanol, ethanol, etc.; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, etc.; aromatic hydrocarbon solvents such as benzene, xylene, toluene, etc.; aliphatic hydrocarbon solvents such as pentane, hexane, cyclohexane, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichloroethane, etc.; nitrile solvents such as acetonitrile, propionitrile, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, etc.; dimethyl sulfoxide, and mixed solvents thereof.

[0077] The reaction can also be carried out using a base. Examples of bases that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2).

[0078] The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride dichloromethane adduct. The amount of the palladium catalyst used can be 0.005 to 20 equivalents per equivalent of compound (2).

[0079] The reaction can be carried out in the presence of a ligand, such as 1,1'-bis(diphenylphosphino)ferrocene, in an amount of 0.005 to 20 equivalents per equivalent of compound (2).

[0080] The reaction temperature can be set at any temperature between −78° C. and the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reactant and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0081] Compound (2) can be produced according to a known method known in the literature, for example, the method described in WO 2021 / 261562.

[0082] Some of the compounds (3) are known compounds, some of which are commercially available, and others can be prepared according to the synthetic methods of known compounds.

[0083] [Production Method 2] The compound (1) of the present invention can be produced by reacting the compound (4) with the compound (5).

[0084] (In the formula, J, Q, X, Y, R ２ and R ３ has the same meaning as above, and Qa is C １ ~C ６ represents alkoxy.)

[0085] The compound (1) of the present invention can be produced by reacting the compound (4) with the compound (5) in a solvent or without a solvent.

[0086] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include the solvents exemplified in Production Method 1.

[0087] The reaction can also be carried out using a base. Examples of bases that can be used include the bases exemplified in Production Method 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (4).

[0088] The reaction temperature can be set at any temperature between −78° C. and the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reactant and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0089] Compound (4) can be produced according to a known method known in the literature, for example, the method described in WO 2021 / 261562.

[0090] Some of the compounds (5) are known compounds, some of which are commercially available, and others can be prepared according to the synthetic methods of known compounds.

[0091] [Production Method 3] Among the compounds (1) of the present invention, compound (1a) in which J represents J-2 can be produced by reacting compound (6). (In the formula, Q, G, X, Y, R ２ and R ３ represents the same meaning as above.)

[0092] Compound (1a) can be produced by reacting compound (6) in a solvent or without a solvent.

[0093] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include the solvents exemplified in Production Method 1.

[0094] The reaction can also be carried out using a base. Examples of bases that can be used include the bases exemplified in Production Method 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (6).

[0095] The reaction temperature can be set at any temperature between −78° C. and the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reactant and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0096] The compound (6) used in Production Method 3 can be produced according to the following reaction scheme.

[0097] [Reaction Scheme 1] (In the formula, Q, G, X, Y, R ２ and R ３ has the same meaning as above, and Jb is C １ ~C ６ represents alkyl.)

[0098] [Production Step 1] Compound (9) can be reacted with compound (5) according to a known method known in the literature, for example, the method described in WO 2016 / 118611, to produce compound (8).

[0099] Some of the compounds (9) are known compounds, and some are commercially available. Others can be prepared by known methods described in the literature, for example, the method described in The Journal of Organic Chemistry, 2004, Vol. 69, pp. 130-141.

[0100] [Production Step 2] Compound (7) can be produced by reacting compound (8) according to a known method known in the literature, for example, the method described in The Journal of Organic Chemistry, 2006, Vol. 24, pages 9045-9050.

[0101] [Production Step 3] Compound (6) can be produced by reacting compound (7) with compound (10) according to a known method known in the literature, for example, the method described in Synthetic Communications, 2006, Vol. 36, pages 729-741.

[0102] Some of the compounds (10) are known compounds, and some are commercially available. Others can be prepared by known methods described in the literature, for example, the method described in Bioorganic & Medicinal Chemistry, 2018, Vol. 26, pp. 1713-1726.

[0103] In the reactions of Production Methods 1 to 3 and Reaction Scheme 1, the reaction mixture after completion of the reaction can be subjected to a conventional post-treatment such as direct concentration, dissolving in an organic solvent and washing with water followed by concentration, or pouring into ice water and extracting with an organic solvent followed by concentration, to obtain the target compound of the present invention. Furthermore, when purification becomes necessary, the compound can be separated and purified by any purification method such as recrystallization, column chromatography, thin-layer chromatography, or liquid chromatographic fractionation.

[0104] Examples of intermediates for producing the compounds of the present invention that can be produced by these methods include the compounds shown in Tables 1 to 6.

[0105] In the table, Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10 and Q-12a represent the following structures.

[0106]

[0107] In addition, the descriptions G-1, G-2, G-3 and G-7 in the table respectively represent the following structures.

[0108]

[0109] The numbers in the structural formulas above indicate the substituents (Z １ ) ｔ２ , (Z １ ) ｔ３ , (Z １ ) ｔ４ , (Z １ ) ｔ５ , (Z ２ ) ｔ４ or (Z ２ ) ｔ５ For example, in the table, "Q-1(4-F)" represents "4-fluorophenyl" and "Q-1" represents "phenyl."

[0110] [Table 1] ―――――― Q ―――――― Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH3) Q-1(4-CF3) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH3) Q-2(4-CF3) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH3) Q-3(4-CF3) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH3) Q-4(4-CF3) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH3) Q-6(4-CF3) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH3) Q-9(4-CF3) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH3) Q-10(3-CF3) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH3) Q-12a(4-CF3) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH3) Q-1(3-CF3) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH3) Q-1(2-CF3) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH3) Q-3(3-CF3) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH3) Q-3(5-CF3) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH3) Q-3(6-CF3) Q-4(3-F)Q-4(3-Cl), Q-4(3-Br), Q-4(3-I), Q-4(3-CN), Q-4(3-CH3), Q-4(3-CF3), Q-6(3-F), Q-6(3-Cl), Q-6(3-Br), Q-6(3-I), Q-6(3-CN), Q-6(3-CH3), Q-6(3-CF3), Q-9(3-F), Q-9(3-Cl), Q-9(3-Br), Q-9(3-I), Q-9(3-CN), Q-9(3-CH3), Q-9(3-CF3) ――――――

[0111] [Table 2] ―――――― Q ―――――― Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH3) Q-1(4-CF3) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH3) Q-2(4-CF3) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH3) Q-3(4-CF3) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH3) Q-4(4-CF3) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH3) Q-6(4-CF3) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH3) Q-9(4-CF3) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH3) Q-10(3-CF3) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH3) Q-12a(4-CF3) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH3) Q-1(3-CF3) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH3) Q-1(2-CF3) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH3) Q-3(3-CF3) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH3) Q-3(5-CF3) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH3) Q-3(6-CF3) Q-4(3-F)Q-4(3-Cl), Q-4(3-Br), Q-4(3-I), Q-4(3-CN), Q-4(3-CH3), Q-4(3-CF3), Q-6(3-F), Q-6(3-Cl), Q-6(3-Br), Q-6(3-I), Q-6(3-CN), Q-6(3-CH3), Q-6(3-CF3), Q-9(3-F), Q-9(3-Cl), Q-9(3-Br), Q-9(3-I), Q-9(3-CN), Q-9(3-CH3), Q-9(3-CF3) ――――――

[0112] [Table 3] ―――――― R 1 G 51 ―――――― H Cl, H Br, H I, F Cl, F Br, F I, Cl Cl, Cl Br, Cl I, CHF2 Cl, CHF2 Br, CHF2 I, CF3 Cl, CF3 Br, CF3 I ――――――

[0113] [Table 4] ―――――― G 51 ―――――― Cl, Br, I ――――――

[0114] [Table 5] ――――――――――― R 1G ――――――――――― Cl G-7 Cl G-1 Cl G-3 Cl G-2 Cl G-7(3-F) Cl G-7(4-F) Cl G-7(5-F) Cl G-7(6-F) Cl G-1(2-F) Cl G-1(4-F) Cl G-1(5-F) Cl G-1(6-F) Cl G-3(2-F) Cl G-3(3-F) Cl G-2(2-F) Cl G-2(3-F) Cl G-2(4-F) Cl G-2(2-F,4-F) Cl G-2(2-F,5-F) Cl G-7(3-Cl) Cl G-7(4-Cl) Cl G-7(5-Cl) Cl G-7(6-Cl) Cl G-1(2-Cl) Cl G-1(4-Cl) Cl G-1(5-Cl) Cl G-1(6-Cl) Cl G-3(2-Cl) Cl G-3(3-Cl) Cl G-2(2-Cl) Cl G-2(3-Cl) Cl G-2(4-Cl) Cl G-2(2-Cl,4-Cl) Cl G-2(2-Cl,5-Cl) Cl G-7(3-CH3) Cl G-7(4-CH3) Cl G-7(5-CH3) Cl G-7(6-CH3) Cl G-1(2-CH3) Cl G-1(4-CH3) Cl G-1(5-CH3) Cl G-1(6-CH3) Cl G-3(2-CH3) Cl G-3(3-CH3) Cl G-2(2-CH3) Cl G-2(3-CH3) Cl G-2(4-CH3) Cl G-2(2-CH3,4-CH3) Cl G-2(2-CH3,5-CH3) Cl G-7(3-CF3) Cl G-7(4-CF3) Cl G-7(5-CF3) Cl G-7(6-CF3) Cl G-1(2-CF3) Cl G-1(4-CF3) Cl G-1(5-CF3) Cl G-1(6-CF3) Cl G-3(2-CF3) Cl G-3(3-CF3) Cl G-2(2-CF3) Cl G-2(3-CF3) Cl G-2(4-CF3) Cl G-2(2-CF3,4-CF3) Cl G-2(2-CF3,5-CF3) CF3 G-7 CF3 G-1 CF3 G-3 CF3 G-2 CF3 G-7(3-F) CF3 G-7(4-F) CF3 G-7(5-F) CF3 G-7(6-F) CF3 G-1(2-F) CF3 G-1(4-F) CF3 G-1(5-F) CF3 G-1(6-F) CF3 G-3(2-F) CF3 G-3(3-F) CF3 G-2(2-F) CF3 G-2(3-F) CF3 G-2(4-F) CF3 G-2(2-F,4-F) CF3 G-2(2-F,5-F) CF3 G-7(3-Cl) CF3 G-7(4-Cl) CF3 G-7(5-Cl) CF3 G-7(6-Cl) CF3 G-1(2-Cl) CF3 G-1(4-Cl) CF3 G-1(5-Cl) CF3 G-1(6-Cl) CF3 G-3(2-Cl) CF3 G-3(3-Cl) CF3 G-2(2-Cl) CF3 G-2(3-Cl) CF3 G-2(4-Cl) CF3 G-2(2-Cl,4-Cl) CF3 G-2(2-Cl,5-Cl) CF3 G-7(3-CH3) CF3 G-7(4-CH3) CF3 G-7(5-CH3) CF3 G-7(6-CH3) CF3 G-1(2-CH3) CF3 G-1(4-CH3) CF3 G-1(5-CH3) CF3 G-1(6-CH3) CF3 G-3(2-CH3) CF3 G-3(3-CH3) CF3 G-2(2-CH3) CF3 G-2(3-CH3) CF3 G-2(4-CH3) CF3 G-2(2-CH3,4-CH3) CF3 G-2(2-CH3,5-CH3) CF3 G-7(3-CF3) CF3 G-7(4-CF3) CF3 G-7(5-CF3) CF3 G-7(6-CF3) CF3 G-1(2-CF3) CF3 G-1(4-CF3) CF3 G-1(5-CF3) CF3 G-1(6-CF3) CF3 G-3(2-CF3) CF3 G-3(3-CF3) CF3 G-2(2-CF3) CF3 G-2(3-CF3) CF3 G-2(4-CF3) CF3 G-2(2-CF3,4-CF3) CF3 G-2(2-CF3,5-CF3) ―――――――――――,

[0115] [Table 6] ―――――――― G ―――――――― G-7 G-1 G-3 G-2 G-7(3-F) G-7(4-F) G-7(5-F) G-7(6-F) G-1(2-F) G-1(4-F) G-1(5-F) G-1(6-F) G-3(2-F) G-3(3-F) G-2(2-F) G-2(3-F) G-2(4-F) G-2(2-F,4-F) G-2(2-F,5-F) G-7(3-Cl) G-7(4-Cl) G-7(5-Cl) G-7(6-Cl) G-1(2-Cl) G-1(4-Cl) G-1(5-Cl) G-1(6-Cl) G-3(2-Cl) G-3(3-Cl) G-2(2-Cl) G-2(3-Cl) G-2(4-Cl) G-2(2-Cl,4-Cl) G-2(2-Cl,5-Cl) G-7(3-CH3) G-7(4-CH3) G-7(5-CH3) G-7(6-CH3) G-1(2-CH3) G-1(4-CH3) G-1(5-CH3) G-1(6-CH3) G-3(2-CH3) G-3(3-CH3) G-2(2-CH3) G-2(3-CH3) G-2(4-CH3) G-2(2-CH3,4-CH3) G-2(2-CH3,5-CH3) G-7(3-CF3) G-7(4-CF3) G-7(5-CF3) G-7(6-CF3) G-1(2-CF3) G-1(4-CF3) G-1(5-CF3) G-1(6-CF3) G-3(2-CF3) G-3(3-CF3) G-2(2-CF3) G-2(3-CF3) G-2(4-CF3) G-2(2-CF3,4-CF3) G-2(2-CF3,5-CF3) ――――――――

[0116] The pest control agent in the present invention means a pest control agent that targets harmful arthropods in the fields of agriculture and horticulture or livestock and sanitation (endoparasites and ectoparasites of mammals or birds as livestock or pets, and sanitary pests and nuisance pests for household and commercial use).

[0117] Furthermore, the agricultural chemicals in the present invention refer to insecticides, acaricides, nematicides, herbicides, fungicides, and the like in the agricultural and horticultural fields.

[0118] In this specification, "sanitary pests" refers to harmful invertebrates that bite target animals, causing allergic symptoms such as severe pain, swelling, and itching, and in some cases, causing fatal anaphylactic shock, or that transmit serious diseases through blood-sucking, sometimes even leading to death; invertebrates that sometimes contaminate food with pathogens such as viruses, bacteria, and parasites through contact with food; invertebrates whose living organisms, carcasses, molted skins, and feces act as allergens, causing allergic diseases such as bronchial asthma, rhinitis, conjunctivitis, and atopic dermatitis; invertebrates that cause economic damage by eating food, clothing, and housing; and invertebrates that do not directly harm humans but cause discomfort by invading and invading their living environments. More specifically, these include ants that bite with their mandibles, hornets that sting with their poisonous stingers, mosquitoes and assassin bugs that suck blood through the skin, and termites that are omnivorous and damage buildings such as houses.

[0119] In this specification, nuisance pests refer to pests that do not directly harm humans in their living environment, but that cause discomfort and psychological harm due to their appearance or shape.

[0120] Specific examples of insects, mites, crustaceans, mollusks, nematodes, ectoparasites, and endoparasites that can be controlled using the compound of the present invention include, but are not limited to, the following organisms:

[0121] Pests include the following from the order Lepidoptera: Allium leafminer (Acrolepiopsis sapporensis), Yam leafminer (Acrolepiopsis suzukiella), Smaller tea tortrix (Adoxophyes honmai), Summer fruit tortrix (Adoxophyes orana fasciata), Fruit-piercing moth (Adris tyrannus), Sweet potato leafworm (Aedia leucomelas), Black cutworm (Agrotis ipsilon), Turnip moth (Agrotis segetum), Cotton leafworm (Alabama argillacea), Asiatic leafroller (Archips breviplicanus), and Apple tortrix (Agrotis segetum). tortrix (Archips fuscocupreanus), Oriental tussock moth (Artaxa subflava), Bamboo zygaenid (Artona martini), Japanese giant looper (Ascotis selenaria), Asiatic common looper (Autographa nigrisigna), Pear leaf miner (Bucculatrix pyrivorella), Tea leafroller (Caloptilia theivora), Peach fruit moth (Carposina sasakii), Rice stem borer (Chilo suppressalis), Rice leafroller (Cnaphalocrocis medinalis), Yellow peach moth (Conogethespunctiferalis), Carpenter moth (Cossus insularis), Threespotted plusia moth (Ctenoplusia agnata), Codling moth (Cydia pomonella), Pine moth (Dendrolimus spectabilis), Jananese hemlock caterpillar (Dendrolimus superans), Cucumber moth (Diaphania indica), Sugarcane borer (Diatraea saccharalis), Scarlet corn moth (Eilema fuscodorsalis), Scarlet corn moth (Eilema laevis), Lesser corn stalk borer (Elasmopalpus lignosellus), Grape berry moth (Endopiza viteana), Limabean pod borer (Etiella zinckenella), Japanese tussock moth (Euproctis piperita), Tea tussock moth (Euproctis pseudoconspersa), Japanese bamboo lappet moth (Euthrix albomaculata), Reed moth (Euthrix potatoria), Oriental lappet moth (Gastropacha orientalis), Mulberry pyralid (Glyphodes pyloalis), Plum fruit moth (Grapholita dimorpha), Pear fruit moth (Grapholita molesta), Sweet potato leaffolder (Helcystogramma triannulella), CottonBollworm (Helicoverpa armigera), Oriental tobacco budworm (Helicoverpa assulta), Corn earworm (Helicoverpa zea), Tobacco budworm (Heliothis virescens), Cabbage webworm (Hellula undalis), Oriental tea tortrix (Homona magnanima), Fall webworm moth (Hyphantria cunea), Pearlleaf worm (Illiberis pruni), Prunus bud moth (Illiberis rotundata), Oak moth (Quercus lasiocampid) (Kunugia undans), Mountain moth (Quercus lasiocampid) (Kunugia yamadai), Soybean pod borer (Leguminivora glycinivorella), Mulberry tiger moth (Lemyra imparilis), Gypsy moth (Lymantria dispar), Peach leafminer (Lyonetia clerkella), Silver leafminer (Lyonetia prunifoliella malinella), Cabbage armyworm (Mamestra brassicae), Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Manduca sexta), Soybean podworm (Matsumuraeses phaseoli), Oriental moth (Monema flavescens), Rice green caterpillar (Narangaaenescens), White-spotted tussock moth (Orgyia thyellina), Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Adzuki bean borer (Ostrinia scapulalis), Dark fruit-tree tortrix (Pandemis heparana), Bluegrass webworm (Parapediasia teterrella), Green cochlid (Parasa consocia), Broad-headed oak moth (Parasa lepida), Chinese cochlid (Parasa sinica), Straight swift (Parnara guttata), Pink bollworm Bollworm (Pectinophora gossypiella), Citrus leafminer (Phyllocnistis citrella), Apple leafminer (Phyllonorycter ringoniella), Large white (Pieris brassicae), Cabbage white butterfly (Pieris rapae crucivora), Diamondback moth (Plutella xylostella), Oriental armyworm (Pseudaletia separata), Soybean looper (Pseudoplusia includens), Swan moth (Sphrageidus similis), Lawn grass cutworm (Spodoptera depravata), Southern armyworm (Spodoptera eridania), Beet armyworm (Spodopteraexigua), Fall armyworm (Spodoptera frugiperda), Cotton leafworm (Spodoptera littoralis), Common cutworm (Spodoptera litura), Persimmon fruit moth (Stathmopoda masinissa), Peach tree borer (Synanthedon exitiosa), Cherry tree borer (Synanthedon hector), Red-necked long-eared moth (Toleria romanovi), Cabbage looper (Trichoplusia ni), etc. Coleoptera: Common bean weevil (Acanthoscelides obtectus), Cupreous chafer (Anomala cuprea), Soybean beetle beetle (Anomala rufocuprea), Asian long-horn beetle (Anoplophora glabripennis), White-spotted longicorn beetle (Anoplophora malasiaca), Boll weevil (Anthonomus grandis), Cucurbit leaf beetle (Aulacophora femoralis), Adzuki bean beetle (Callosobruchus chinensis), Flea beetle (Chaetocnema concinna), Sweet potato weevil (Cylas formicarius), Leaf beetle (Demotina fasciculata), Northern corn rootworm (Diabroticabarberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Rice plant weevil (Echinocnemus squameus), Mexican bee beetle (Epilachna varivestis), Large 28-spotted ladybird (Epilachna vigintioctomaculata), 28-spotted ladybird (Epilachna vigintioctopunctata), Epuraea domina, West Indian sweet potato weevil (Euscepes postfasciatus), Citrus flower chafer (Gametis jucunda), White-fringed beetle (Graphognatus leucoloma), Yellowish elongate chafer (Heptophylla picea), Alfalfa weevil (Hypera postica), Tobacco beetle (Lasioderma serricorne), Colorado potato beetle (Leptinotarsa ​​decemlineata), Rice water weevil (Lissohoptrus oryzophilus), Sweetpotato wireworm (Melanotus fortnumi), Sugarcane wireworm (Melanotus tamsuyensis), Pollen beetle (Meligethes aeneus), Japanese pine sawyerPine sawyer (Monochamus alternatus), Black vine weevil (Otiorhynchus sulcatus), Rice leaf beetle (Oulema oryzae), Rove beetle (Paederus fuscipes), Mustard leaf beetle (Phaedon cochleariae), Striped flea beetle (Phyllotreta striolata), Japanese beetle (Popillia japonica), Yellow-spotted longicorn beetle (Psacothea hilaris), Solanum flea beetle (Psylliodes angusticollis), Peach curculio (Rhynchites heros), Granary weevil (Sitophilus granarius), Maize weevil (Sitophilus zeamais), Hunting billbug (Sphenophorus venatus vestitus), Yellow mealworm (Tenebrio molitor), Red flour beetle (Tribolium castaneum), Grape borer (Xylotrechus pyrrhoderus), etc. Hymenoptera: Chestnut sawfly (Apethymus kuri), Large rose sawfly (Arge pagana), Cabbage sawfly (Athalia infumata), Turnip sawfly (Athalia rosae), Japanese carpenter Ant (Camponotus japonicus), chestnut gall waspWasp (Dryocosmus kuriphilus), Army ant (Eciton burchellii, E. schmitti), Argentine ant (Linepithema humile), Pharaoh ant (Monomorium pharaonis), Bulldog ant (Myrmecia spp.), European pine sawfly (Neodiprion sertifer), Fire ant (Solenopsis spp.), Asian giant hornet (Vespa mandarinia), Japanese yellow hornet (Vespa simillima), etc. Diptera: Yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus), Aedes species (Aedes spp.), Aedes taeniorhynchus, Rice leaf miner (Agromyza oryzae), Mexican fruit fly (Anastrepha ludens), African malaria mosquito (Anopheles gambiae), African malaria mosquito (Anopheles hyrcanus sinensis), Anopheles koreicus, Anopheles lesteri, Anopheles maculipennis, Anopheles spp., Soybean pod gall midge (Asphondylia yushimai), Atylotus spp., Melon fly (Bactroceracucurbitae), Oriental fruit fly (Bactrocera dorsalis), Queensland fruit fly (Bactrocera tryoni), Japanese orange fly (Bactrocera tsuneonis), Boophthora erythrocephala, Braula coeca, Braula spp., Calliphora erythrocephala, Calliphora lata, Calliphora spp., Bottle fly (Calliphora vicina), Mediterranean fruit fly (Ceratitis capitata), Pea leaf miner (Chromatomyia horticola), Old World screw-worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya megacephala), Chrysomya spp., Splayed deerfly (Chrysops caecutiens), Chrysops relictus, Chrysops spp., Deer fly (Chrysops suavis), Chrysozona pluvialis, New World screw-worm fly (Cochliomyia hominivorax), House mosquito (Culex pipiens molestus), House mosquito (Culex pipiens pallens), Culex quinquefasciatusquinquefasciatus), Culex tarsalis, Culex tritaeniorhynchus, Culex spp., Biting midge (Culicoides arakawae), Culicoides spp., Bot flies (Cuterebra spp.), Onion fly (Delia antiqua), Seed corn maggot (Delia platura), Human botfly (Dermatobia hominis), Japanese fruit fly (Drosophila suzukii), Eusimulium spp., Lesser house fly (Fannia canicularis), Fannia spp. spp.), Horse nose bot fly (Gasterophilus haemorrhoidalis), Gasterophilus inermis, Horse bot fly (Gasterophilus intestinalis), Throat bot fly (Gasterophilus nasalis), Gasterophilus nigricornis, Gasterophilus pecorum, Gasterophilus spp., Tsetse fly (Glossina morsitans, G. palpalis), Glossina spp., Horn fly (Haematobia irritans), Haematobia irritans exigua, Haematobia spp. spp.), Haematobia stimulans, Haematopota italicaitalic), Common horse fly (Haematopota pluvialis), Haematopota spp., Forest fly (Hippobosca equina), Hippobosca spp., Hippobosca variegate, Hybomitra ciurea, Hybomitra spp., Smaller rice leaf miner (Hydrellia griseola), Hydrotaea albipuncta, Sheep headfly (Hydrotaea irritans), Hydrotaea spp., Warble fly (Hypoderma bovis), Common cow fly Cattle grub (Hypoderma lineatum), Hypoderma spp., Black gnat (Leptoconops nipponensis), Lipoptena capreoli, Lipoptena cervi, Lipoptena spp., Cabbage leafminer (Liriomyza brassicae), Tomato leafminer (Liriomyza bryoniae), Stone leek leafminer (Liriomyza chinensis), Pea leafminer (Liriomyza huidobrensis), Tomato leafminer (Liriomyza sativae), Serpentine leafminer (Liriomyza trifolii), Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Luciliaillustris), Common green bottle fly (Lucilia sericata), Lucilia spp., Lutzomyia spp., Hessian fly (Mayetiola destructor), Sheep ked (Melophagus ovinus), Melophagus spp., Sweat fly (Morellia simplex), Morellia spp., Face fly (Musca autumnalis), Housefly (Musca domestica), Musca spp., Australian bush fly (Musca vetustissima), Odagmia ornate, Odagmia spp., Sheep nasal Bot fly (Oestrus ovis), Oestrus spp., Beet leaf miner (Pegomya cunicularia), Philipomyia spp., Phlebotomus longipalpis, Phlebotomus papatasi, Sandfly (Phlebotomus spp.), Black blow fly (Phormia regina), Yellow-legged fly (Prosimulium yezoensis), Northern blowfly (Protophormia terraenovae), Przhevalskiana silenus, Apple maggot (Rhagoletis pomonella), Rhinoestrus spp., Flesh fly fly (Sarcophaga carnaria), flesh fly (Sarcophagaperegrina), Sarcophaga spp., Black fly (Simulium ochraceum), Simulium reptans, Simulium spp., Orange wheat blossom midge (Sitodiplosis mosellana), Stable fly (Stomoxys calcitrans), Stomoxys spp., Tabanus atratus, Tabanus bromius, Greenhead horse fly (Tabanus nigrovittatus), Tabanus spodopterus, Tabanus spp., Tabanus sudeticus, Horse fly (Tabanus trigonus), Moth Hemiptera: green stink bug (Acrosternum hilare), pea aphid (Acyrthosiphon pisum), Camellia spiny whitefly (Aleurocanthus camelliae), orange spiny whitefly (Aleurocanthus spiniferus), Indian cotton leafhopper (Amrasca devastans), California red scale (Aonidiella aurantii), Cowpea aphidAphid (Aphis craccivora), Black bean aphid (Aphis fabae), Soybean aphid (Aphis glycines), Cotton aphid (Aphis gossypii), Green apple aphid (Aphis pomi), Spiraea aphid (Aphis spiraecola), Pale greenplant bug (Apolygus spinolae), Grape leafhopper (Arboridia apicalis), Foxglove aphid (Aulacorthum solani), Beardsley leafhopper (Balclutha saltuella), Silverleaf whitefly (Bemisia argentifolii), Sweetpotato Whitefly (Bemisia tabaci), True chinch bug (Blissus leucopterus), Leafcurl plum aphid (Brachycaudus helichrysi), Cabbage aphid (Brevicoryne brassicae), Oriental chinch bug (Cavelerius saccharivorus), Indian wax scale (Ceroplastes ceriferus), Red wax scale (Ceroplastes rubens), Walnut aphid (Chromaphis juglandicola), Bed bug (Cimex lectularius), Rice stink bug (Cletus punctiger), Citricola scale (Coccuspseudomagnoliarum), San jose scale (Comstockaspis perniciosa), Citrus whitefly (Dialeurodes citri), Asian citrus psyllid (Diaphorina citri), stinkbag (Dichelops furcatus), Russian wheat aphid (Diuraphis noxia), Sloe bug (Dolycoris baccarum), Giant margarodid scale (Drosicha corpulenta), Rosy apple aphid (Dysaphis plantaginea), Red cotton bug (Dysdercus cingulatus), Potato leafhopper (Empoasca fabae), persimmon leafhopper Empoasca nipponica (Empoasca nipponica), tea green leafhopper Empoasca onukii, bean's smaller green leafhopper Empoasca sakaii, grape leafhopper Epiacanthus stramineus, woolly apple aphid Eriosoma lanigerum, cabbage bug Eurydema rugosa, brown stink bug Euschistus servus, white-spotted spined bug Eysarcoris aeneus, large spiny white-spotted bug Eysarcoris lewisi (Eysarcoris lewisi), White-spotted stink bug (Eysarcoris ventralis), Tea leaf scaleScale (Fiorinia theae), Shield bug (Glaucias subpunctatus), Island fleahopper (Halticus insularis), Brown marmorated stink bug (Halyomorpha halys), Mealy plum aphid (Hyalopterus pruni), Cottony cushion scale (Icerya purchasi), Small brown planthopper (Laodelphax striatellus), Rice bug (Leptocorisa chinensis), Turnip aphid (Lipaphis erysimi), Western tarnished plant bug (Lygus hesperus), Tarnished plant bug (Lygus lineolaris), Potato aphid (Macrosiphum euphorbiae), Aster leafhopper (Macrosteles fascifrons), Grape leafhopper (Macrosteles striifrons), Sugarcane spittlebug (Mahanarva fimbriolata), Blackmargined aphid (Monellia caryella), Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Onion aphid (Neotoxoptera formosana), Green rice leafhopper (Nephotettix cincticeps), Eastern green stink bug (Nezaraantennata), Southern green stink bug (Nezara viridula), Brown rice planthopper (Nilaparvata lugens), Squash bug (Paradasynus spinosus), Cotton mealy bug (Phenacoccus solani), Redbanded stink bug (Piezodorus guildinii), Redbanded shield bug (Piezodorus hybneri), Citrus mealybug (Planococcus citri), Japanese mealybug (Planococcus kraunhiae), Brown-winged green bug (Plautia crossota), Peony scale (Pseudaonidia paeoniae), Cotton fleahopper (Pseudatomoscelis seriatus), Mulberry scale (Pseudaulacaspis pentagona), White peach scale (Pseudaulacaspis prunicola), Comstock mealybug (Pseudococcus comstocki), Grape mealybug (Pseudococcus maritimus), Pear psylla (Psylla pyrisuga), Blood-sucking bug (Rhodnius prolixus), Bird cherry-oat aphid (Rhopalosiphum padi), Rice root aphid (Rhopalosiphum rufiabdominalis), Rhopalid bug (Rhopalusmaculatus), Bean bug (Riptortus clavatus), Greenbug (Schizaphis graminum), Japanese black rice bug (Scotinophora lurida), Corn leaf aphid (Sitobion akebiae), English grain aphid (Sitobion avenae), White-backed rice planthopper (Sogatella furcifera), Rice stink bug (Stenodema sibiricum), Sorghum plant bug (Stenotus rubrovittatus), Azalea lace bug (Stephanitis pyrioides), Seed bug (Togo hemipterus), Black citrus aphid (Toxoptera aurantii), Brown citrus aphid (Toxoptera citricida), Greenhouse whitefly (Trialeurodes vaporariorum), Mexican kissing bug (Triatoma dimidiata), Brazilian kissing bug (Triatoma infestans), Rice leaf bug (Trigonotylus caelestialium), Citrus snow scale (Unaspis citri), Euonymus scale (Unaspis euonymi), Arrowhead scale (Unaspis yanonensis), Grape phylloxera (Viteus vitifolii), etc., Thysanoptera; Flower thripsOrthoptera: Australian plague locust (Chortoicetes terminifera), Oriental mole cricket (Gryllotalpa orientalis), Migratory locust (Migratory locust), etc. Locust (Locusta migratoria), Lesser paddy grasshopper (Oxya japonica), Rice grasshopper (Oxya yezoensis), Desert locust (Schistocerca gregaria), Emma field cricket (Teleogryllus emma), etc. Order Blattola: German cockroach (Blattella germanica), Formosan subterranean termite (Coptotermes formosanus), Daikoku dry-wood termite (Cryptotermes domesticus), Western dry-wood termite (Incisitermes minor), Black-winged subterranean termite (Odontotermesformosanus), American cockroach (Periplaneta americana), Smoky-brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), Japanese subterranean termite (Reticulitermes speratus), etc., Isoptera: Coptotermes formosanus (Coptotermes formosanus), Reticulitermes speratus (Reticulitermes speratus), Odontotermes formosanus (Odontotermes formosanus), etc., Acari: Cyclamen mite (Phytonemus pallidus), Broad mite (Polyphagotarsonemus latus), Tarsonemus bilobatus (Tarsonemus bilobatus), Chinese cabbage mite (Penthaleus erythrocephalus), Winter grain mite (Penthaleus major), Rice spider mite (Oligonychus shinkajii), Citrus red mite (Panonychus citri), Mulberry giant spider mite (Panonychus mori), European red mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), Two-spotted spider mite (Tetranychus urticae), Tea long-spotted rust mite (Acaphylla theavagrans), Tulip rust mite (DryBulb mite (Aceria tulipae), Tomato erineum mite (Aculops lycopersici), Pink citrus rust mite (Aculops pelekassi), Apple rust mite (Aculus schlechtendali), Pear rust mite (Eriophyes chibaensis), Citrus rust mite (Phyllocoptruta oleivora), Bulb mite (Rhizoglyphus robini), Mold mite (Tyrophagus putrescentiae), Spinach mite (Tyrophagus similis), Acarapis spp., Honey bee tracheal mite (Acarapis woodi), and Acarus spp. spp.), Lone star tick (Amblyomma americanum), Cayenne tick (Amblyomma cajennense), South African bont tick (Amblyomma hebraeum), Gulf coast tick (Amblyomma maculatum), Amblyomma spp., Tropical bont tick (Amblyomma variegatum), Fowl tick (Argas persicus), Pigeon tick (Argas reflexus), Argas spp., Blue cattle tick (Boophilus annulatus), Boophilus calceratus, African blue tick (Boophilusdecoloratus), Tropical cattle tick (Boophilus microplus), Boophilus spp., Caloglyphus spp., Chelacaropsis moorei, Cat tick (Cheyletiella blakei), Rabbit fur mite (Cheyletiella parasitovorax), Cheyletiella spp., Dog tick (Cheyletiella yasguri), Cheyletus eruditus, Stag beetle tick (Cheyletus malaccensis), Chorioptic mange mite (Chorioptes bovis), Chorioptes spp., Cytodites spp., and Demodex follicle Demodex mite (Demodex bovis), Demodex caballi, Dog follicle mite (Demodex canis), Demodex caprae, Cat follicle mite (Demodex cati), Demodex equi, Face mite (Demodex folliculorum), Demodex ovis, Demodex spp., Sarcoptes suis mite (Demodex suis), Winter tick (Dermacentor albipictus), Rocky Mountain wood tick (Dermacentor andersoni), Ornate sheep tick (Dermacentor marginatus), Meadow tick (Dermacentor pictus), Ornate dog ticktick (Dermacentor reticulatus), Dermacentor spp., American dog tick (Dermacentor variabilis), Poultry red mite (Dermanyssus gallinae), Dermacentor spp., American house dust mite (Dermatophagoides farina), House dust mite (Dermatophagoides pteronyssinus), Asian chigger (Eutrombicula wichmanni), Storage mite (Glycyphagus destructor), House itch mite (Glycyphagus domesticus), Haemaphysalis cinnabarina, Common rodent tick (Haemaphysalis concinna), Yellow dog tick tick (Haemaphysalis leachi), Bush tick (Haemaphysalis longicornis), Haemaphysalis otophila, Red sheep tick (Haemaphysalis punctate), Haemophysalis spp., House mite (Haplochthonius simplex), Trombiculid mite (Helenicula miyagawai), Tortoise tick (Hyalomma aegyptium), Hyalomma anatolicum, Bont-legged tick (Hyalomma marginatum), Hyalomma mauritanicus, Hyalomma spp.spp.), Small smooth bont-legged tick (Hyalomma transiens), Hypodectes spp., Dog tick (Ixodes canisuga), Hedgehog tick (Ixodes hexagonus), Australian paralysis tick (Ixodes holocyclus), Western black-legged tick (Ixodes pilosus), Castor bean tick (Ixodes ricinus), Karoo paralysis tick (Ixodes rubicundus), Deer tick (Ixodes scapularis), Ixodes spp., Knemidocoptes spp., Laminosioptes spp.), Leptotrombidium akamushi, Leptotrombidium pallida, Leptotrombidium scutellare, Listrophorus spp., Megninia cubitalis, Myobia spp., Neoschoengastia xerothermobia, Neotrombicula autumnalis, Neotrombicula desaleri, Notoedres cati, Notoedres spp., Ornithocheyletia spp., Soft tick tick (Ornithodorus moubata), Ornithodorus species (Ornithodorusspp.), Tropical fowl mite (Ornithonyssus bursa), Ornithonyssus spp., Northern fowl mite (Ornithonyssus sylviarum), Spinose ear tick (Otobius megnini), Otobius spp., Dog ear mite (Otodectes cynotis), Otodectes spp., Canine nasal mite (Pneumonyssoides caninum), Pneumonyssoides mange, Pneumonyssus spp., Pneumonyssus spp., Psorergates spp.), Psoroptic mite (Psoroptes communis), Rabbit ear mite (Psoroptes cuniculi), Psoroptes equi, Sheep scab mite (Psoroptes ovis), Psoroptes ovis, Psoroptes spp., Feather mite (Pterolichus obtusus), Pterolichus spp., Raillietia spp., Brown ear tick (Rhipicephalus appendiculatus), Brown ear tick (Rhipicephalus bursa), Rhipicephalus capensis, Asian blue tick tick (Rhipicephalus evertsi), Kennel tick (Rhipicephalussanguineus), Rhipicephalus spp., Rhipicephalus turanicus, Rhipicephalus zambeziensis, Sarcoptes bovis, Sarcoptes equi, Sarcoptes ovis, Sarcoptes rupicaprae (=S. caprae), Itch mite (Sarcoptes scabiei), Sarcoptes spp., Sarcoptes suis, Itch mite (Sarcoptis canis), Sternostoma spp., Trombicula akamushi, Trombicula spp., Cheese mites (Tyrophagus putrescentiae), Tyrophagus spp., Varroa mites (Varroa jacobsoni), Varroa spp., etc., Anoplurida: Short-nosed cattle louse (Haematopinus eurysternus), Tail switch louse (Haematopinus quadripertusus), Pig louse (Haematopinus spp.), Large pig louse (Haematopinus suis), Buffalo louse (Haematopinus tuberculatus), Rabbit louse (Haemodipsus ventricosus), Dog sucking louse (Linognathus setosus), Cattle louse (Linognathus spp.), Long-nosed cattle louse (Linognathusvituri), Head louse (Pediculus humanus), Pediculus spp., Mouse louse (Polyplax serratus), Crab louse (Pthirus pubis), Pthirus spp., Little blue cattle louse (Solenopotes capillatus), Solenopotes spp., etc.; Mallophaga: Goat biting louse (Bovicola caprae), Bovicola limbata, Sheep body louse (Bovicola ovis), Bovicola spp., Chicken head louse (Cuclotogaster heterographa), Cattle chewing louse (Damalinia bovis), Felicola spp., Cat louse (Felicola subrostrata), Brown chicken louse (Goniodes dissmilis), Fluff louse (Goniodes gallinae), Large hen louse (Goniodes gigas), Lepikentron ovis, Lepikentron spp., Wing louse (Lipeurus caponis), Body louse (Menacanthus cornutus), Small body louse (Menacanthus pallidulus), Menacanthus spp. spp.), Chicken body louse (Menacanthus stramineus), Chicken shaft louse (Menopongallinae), Menopon spp., Dog biting louse (Trichodectes canis), Animal biting louse (Trichodectes spp.), Werneckiella equi, Werneckiella spp., etc., Siphonaptera: Chicken flea (Ceratophyllus gallinae), Dog flea (Ctenocephalides canis), Cat flea (Ctenocephalides felis), Sticktight flea (Echidnophaga gallinacean), Human flea (Pulex irritans), Chigoe flea (Tunga penetrans), Oriental rat flea (Xenopsylla cheopis), etc., Other parasites include Monogenea: Benedenia epinepheli, Benedenia hoshinai, Benedenia sekii, Benedenia seriolae, Bivagina tai, sea louse (Caligus curtus), Caligus elongates, Caligus labaracis, Caligus longipedis, Caligus orientalis, Caligus teres, Dactylogyrus spp., Gyrodactylus spp. spp.), Heteraxine heterocerca, Heterobothrium okamotoi, Lamellodiscus spp., Copepods (Lepeophtheiruscuneifer, Lepeophtheirus hippoglossi, Lepeophtheirus pectoralis, salmon louse (Lepeophtheirus salmonis), Microcotyle sebastis, Microcotyle sebastisci, Neobenedenia, Neobenedenia congeri, Neobenedenia girellae, Neoheterobothrium hirame, Polystoma spp., Pseudocaligus fugu, Zeuxapta japonica, etc. Tapeworms (Cestoda): Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Bothridium spp., Cittotaenia spp., Davainea spp., Diorchis spp., Manson's tapeworm (Diphyllobothrium erinacei), fish tapeworm (Diphyllobothrium latum), Diphyllobothrium spp., Diphyllogonoporus spp., Diplopylidium spp., dog tapeworm (Dipylidium caninum), Dipylidium spp., dog tapeworm (Echinococcus granulosus), fox tapeworm (Echinococcusmultilocularis, Echinococcus spp., Echinocotyle spp., Echinolepsis spp., Hydatigera spp., Hymenolepis diminuta, Hymenolepis spp., Joyeuxiella spp., Ligura spp., Mesocestoides spp., Moniezia benedeni, Moniezia spp., Paranoplocephala spp., Raillietina spp., Schistocephalus spp., Spirometra spp. spp.), Stilesia spp., beef tapeworm (Taenia saginata), pork tapeworm (Taenia solium), Taenia spp.), cat tapeworm (Taenia taeniaeformis), Thysaniezia spp. spp.), Thysanosomsa spp., Trematoda; Austrobilharzia spp., Brachylaema spp., Calicophoron spp., Catatropis spp., liver fluke Chinese river fluke (Clonorchis) sinensis), Clonorchis spp., Collyriclum spp. spp.), Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp.spp.), Echinoparyphium spp., Echinostoma spp., Eurytrema coelomaticum, pancreas fluke (Eurytrema pancreaticum), Eurytrema spp., liver fluke (Fasciola gigantica), sheep liver fluke (Fasciola hepatica), Fasciola spp., Fasciolides spp., large intestinal fluke (Fasciolopsis bruski), Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp. spp.), Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Oriental lung fluke (Paragonimus westermani, Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosomahaematobium, Schistosoma japonicum, Schistosoma mansoni, Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp., etc., Nematoda: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Anisakis spp., Ascaridia galli, Ascaridia spp., Ascaris spp., Ascaris roundworm, Ascaris spp., suum, Aspiculuris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Cooperia oncophora intestinal worm, Cooperia spp., Crenosoma spp., Cyathostoma spp., Cyclocercus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Dirofilaria immitis), Dirofilaria spp., Dracunculus spp., Draschia spp., Elaphostrongylus spp., Enoplida spp., Enterobius spp., Filaroides spp.spp.), Filicollis spp., Globocephalus spp., Gnathostoma spp., Gongylonema spp., Gyalocephalus spp., Habronema spp., Barber's pole worm (Haemonchus contortus), Haemonchus spp., Heterakis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Macracanthorhynchus spp., Marshallagia spp., Metastrongylus spp. spp.), Micronema spp., Moniliformis spp., Muellerius spp., Nematodirus spp., Neostrongylus spp., Obeliscoides spp., Oeophagostomum dentatum, Oesophagodontus spp., Oesophagostomum radiatum, Oesophagostomum spp., Ollulanus spp., Onchocerca gibsoni, Onchocerca spp., Brown stomach worm (Ostertagia ostertagi), Ostertagia spp., Oxyuris spp., Parabronema spp., Paraacrenosoma spp., Parafilaria spp., Parafilaroides spp.spp.), Parascaris spp., Parelaphostrongylus spp., Passalurus spp., Physaloptera spp., Pneumostrongylus spp., Poteriostomum spp., Prostenorchis spp., Protostrongylus spp., Setaria spp., Spicocaulus spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp. spp.), Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichomosoides spp., Trichonema spp., Colubriformis ruminant nematode, Trichostrongylus spp., Trichuris spp., Triodontophorus spp., Uncinaria spp., Wuchereria spp., etc. Protozoa; Babesia spp. spp.), Eimeria acervulina, Eimeria bovis, Eimeria brunette, Eimeria maxima, Eimeria necatrixnecatrix), Eimeria ovinoidalis, Eimeria spp., Eimeria tenella, Entamoeba histolytica, Giardia spp., Histomanas spp., Plasmodium spp., Theileria spp., Toxoplasma spp., Trichomonadidae spp., Trypanosomsa cruzi, and the like.

[0122] Furthermore, the compounds of the present invention are also effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, and pyrethroid compounds.

[0123] That is, the compound of the present invention can effectively control pests belonging to the order Collembola, Dictyoptera (Bockroaches), Orthoptera (Orthoptera), Termitida, Thysanoptera (Thysanoptera), Hemiptera (Hemiptera and Cicadellida), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Flea Bugs), and Phthiraptera, as well as crustaceans such as Lepidoptera, Cyprinodontida, and Cyclopida, as well as mites, gastropods, cestodes, trematodes, nematodes, and protozoa, even at low concentrations.

[0124] On the other hand, the compound of the present invention has an extremely useful feature of having almost no adverse effect on mammals, fish, crustaceans, and beneficial insects (useful insects such as honeybees and bumblebees, and natural enemies such as aster wasps, oil wasps, parasitic flies, oreochromis orbicularis, and phytoseiid mites).

[0125] When using the compound of the present invention, it is usually mixed with a suitable solid or liquid carrier, and if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, antifoaming agents, preservatives, antidegradants, etc. may be added to prepare a formulation of any dosage form, such as a soluble concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granules, water-soluble granules, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule tablet, emulsifiable gel, etc. From the viewpoint of labor saving and improved safety, the formulation of any of the above dosage forms can also be enclosed in a water-soluble package such as a water-soluble capsule or a water-soluble film bag.

[0126] Examples of solid carriers include natural minerals such as quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite, metahaloysite, kibushi clay, gairome clay, pottery stone, ziglite, allophane, shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, and diatomaceous earth; calcined products of natural minerals such as calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay, and calcined diatomaceous earth; magnesium carbonate, calcium carbonate, sodium carbonate, Examples of suitable inorganic salts include sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, and potassium chloride; sugars such as glucose, fructose, sucrose, and lactose; polysaccharides such as starch, powdered cellulose, and dextrin; organic substances such as urea, urea derivatives, benzoic acid, and salts of benzoic acid; plants such as wood flour, cork powder, corn cobs, walnut shells, and tobacco stalks; fly ash, white carbon (e.g., hydrated synthetic silica, anhydrous synthetic silica, hydrated synthetic silicate, etc.), and fertilizers.

[0127] Examples of the liquid carrier include xylene, alkyl (C ９ or C １０ etc.) benzene, phenylxylylethane, alkyl (C １ or C ３aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin, naphthene, etc.; mixtures of aromatic and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropyl alcohol, cyclohexanol, phenoxyethanol, benzyl alcohol, etc.; polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol; ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone, and γ-butyrolactone; esters such as fatty acid methyl esters, dialkyl succinate esters, dialkyl glutamate esters, dialkyl adipate esters, and dialkyl phthalate esters; N-alkyl(C １ , C ８ or C １２ acid amides such as pyrrolidone; oils and fats such as soybean oil, linseed oil, rapeseed oil, palm oil, cottonseed oil, castor oil; dimethyl sulfoxide, water; and the like.

[0128] These solid carriers and liquid carriers may be used alone or in combination of two or more.

[0129] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono- or di-)phenyl ethers, polyoxyethylene (mono-, di-, or tri-)styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono- or di-)esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol, and alkyl glycosides; alkyl sulfate ester salts, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene anionic surfactants such as alkyl phenyl ether sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, polyoxyethylene alkyl ether sulfates or phosphate ester salts, polyoxyethylene (mono- or di-) alkyl phenyl ether sulfates or phosphate ester salts, polyoxyethylene (mono-, di-, or tri-) styryl phenyl ether sulfates or phosphate ester salts, polycarboxylates (for example, polyacrylates, polymaleates, copolymers of maleic acid and olefins, etc.), and polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid type and betaine type; silicone-based surfactants; and fluorine-based surfactants.

[0130] The content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by mass per 100 parts by mass of the formulation of the present invention. These surfactants may be used alone or in combination of two or more.

[0131] The dosage of the compound of the present invention varies depending on the application site, application time, application method, cultivated crop, etc., but usually, an amount of the active ingredient of about 0.005 to 50 kg per hectare (ha) is appropriate.

[0132] On the other hand, when the compound of the present invention is used to control internal or external parasites in mammals and birds as livestock and pets, an effective amount of the compound of the present invention can be administered together with formulation additives by oral administration; parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); transdermal administration such as immersion, spraying, bathing, washing, pouring-on, spotting-on, dusting, etc.; nasal administration; etc. The compound of the present invention can also be administered by a molded product using a strip, plate, band, collar, ear mark, limb band, marking device, etc.

[0133] For administration, the compound of the present invention can be prepared in any dosage form suitable for the administration route.

[0134] When the compound of the present invention is used to eliminate external or internal parasites, the preferred dosage of the compound (1) of the present invention as the active ingredient depends on the type of target parasite to be controlled, the species of target animal to be administered, the method of administration, etc., but is usually 0.01 to 100 mg / kg, preferably 0.01 to 50 mg / kg, of the body weight of the target animal to be administered. In particular, the dosage for dogs may vary depending on the type or age of the target dog or the ectoparasite to be controlled, but is usually 1 to 5000 mg / kg, preferably 1 to 100 mg / kg, of the live body weight of the target dog.

[0135] When administering the compound of the present invention to eliminate external or internal parasites, the administration interval will depend on the type of target parasite to be controlled, the species of target animal to be administered, the administration method, etc., but can usually be set arbitrarily in the range of once every day to once every year, preferably once every week to once every six months, more preferably every day (24 hours), every month, once every month, once every two months, once every three months, or once every six months.

[0136] Furthermore, when the compound of the present invention is used to control ectoparasites in dogs, the timing of administration of the compound of the present invention to dogs can be, for example, 30 minutes before the start of feeding or 120 minutes after the end of feeding. Here, 30 minutes before the start of feeding and 120 minutes after the end of feeding are based on the act of eating food given to the dog for the purpose of nutritional intake. For example, if a dog's feeding time is 20 minutes, the specified time is based on the act of eating, and is a total of 170 minutes from 30 minutes before the start of feeding to 120 minutes after the end of feeding. This also includes cases where feeding is temporarily interrupted during feeding and then resumed after oral administration of the compound of the present invention. In this specification, "feeding" refers to the act of an animal eating food.

[0137] Generally, the number of times a dog is fed per day varies depending on the breed, age, and habits of the dog, but is usually 3 to 4 times a day for dogs under six months old, 2 to 3 times a day for dogs between six months and one year old, 2 to 3 times a day for adult dogs about 1 to 5 years old, and 2 to 3 times a day for dogs 6 years old or older. In the present invention, "feeding" means the act of eating for the purpose of taking in nutrients, and does not include the act of feeding food or the like for the purpose of so-called dog discipline or training.

[0138] The dosage forms that may be prepared include solid preparations such as powders, granules, wettable powders, pellets, tablets, boli, capsules, and molded products containing the active compound; liquid preparations such as injectable solutions, oral solutions, and solutions for application on the skin or into body cavities; solution preparations such as pour-on preparations, spot-on preparations, flowable preparations, and emulsions; and semi-solid preparations such as ointments and gels.

[0139] Dosage forms for oral administration of the compound of the present invention include, for example, solid preparations such as tablets, chewables, capsules, pills, boluses, granules, and powders; semi-solid preparations such as pastes and gels; and liquid preparations such as drinks.

[0140] Furthermore, examples of dosage forms for transdermal administration include solid preparations such as powders; semi-solid preparations such as creams, ointments, pastes, and gels; and liquid preparations such as sprays, aerosols, solutions and emulsions, suspensions, and lotions.

[0141] Furthermore, dosage forms for administration by injection include, for example, liquid preparations such as solutions and emulsions and suspensions, and dosage forms for administration via the nose include, for example, liquid preparations such as aerosols.

[0142] Furthermore, examples of the formulation for spraying in animal rearing environments such as livestock barns include solid preparations such as wettable powders, dusts, and granules; and liquid preparations such as emulsions and suspension concentrates.

[0143] However, the formulations used in the parasite control agent of the present invention are not limited to these dosage forms.

[0144] The solid preparation can be administered orally as it is, or diluted with water and used by transdermal administration or by spraying in the animal rearing environment such as a livestock barn.

[0145] A solid preparation for oral administration can be prepared by mixing the compound (1) of the present invention or a salt thereof with one or more excipients and binders suitable for oral administration, and further, if necessary, physiologically acceptable additives such as lubricants, disintegrants, dyes, pigments, etc., and molding the mixture into a desired shape.

[0146] Examples of excipients and binders include sugars or sugar derivatives such as lactose, sucrose, mannitol, and sorbitol; starches such as corn starch, wheat starch, rice starch, and potato starch; celluloses or cellulose derivatives such as methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, and hydroxypropylmethyl cellulose; proteins or protein derivatives such as zein and gelatin; and synthetic polymer compounds such as honey, gum arabic paste, polyvinyl alcohol, and polyvinylpyrrolidone.

[0147] Examples of lubricants include magnesium stearate, and examples of disintegrants include cellulose, agar, alginic acid, cross-linked polyvinylpyrrolidinone, carbonates, and the like.

[0148] Furthermore, among solid preparations used for oral administration, particularly in the case of solid preparations such as chewable preparations, additives are also used to impart a taste, texture, and flavor preferred by the animal to which the preparation is administered, but the carriers and additives used in solid preparations of parasite control compositions are not limited to these.

[0149] The liquid preparation can be administered transdermally or by injection as is, or can be mixed with feed and administered orally, diluted with water and administered orally or transdermally, or sprayed in the animal rearing environment such as a livestock barn.

[0150] Injectable solutions can be administered intravenously, intramuscularly, or subcutaneously. Injectable solutions can be prepared by dissolving the active compound in a suitable solvent and adding, if necessary, additives such as solubilizers, acids, bases, buffer salts, antioxidants, and protective agents.

[0151] Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone, and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.

[0152] Examples of the solubilizing agent include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

[0153] Examples of the protecting agent include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, and n-butanol.

[0154] Oral liquid preparations can be administered directly or after dilution, and can be prepared in the same manner as injectable liquid preparations.

[0155] Flowables, emulsions, etc. can be administered directly or diluted, transdermally, or by environmental treatment.

[0156] Solutions for use on the skin can be administered by dropping, spreading, rubbing, spraying, sprinkling, or by application by immersion (dipping, bathing, or washing). These solutions can be prepared in the same way as solutions for injection.

[0157] Pour-on and spot-on preparations are dropped or sprayed onto a limited area of ​​the skin, allowing the active compound to penetrate the skin and act systemically.

[0158] Drops and drops can be prepared by dissolving, suspending, or emulsifying the active ingredient in a suitable skin-compatible solvent or solvent mixture, and, if necessary, adding auxiliary agents such as surfactants, colorants, absorption promoters, antioxidants, light stabilizers, adhesives, etc.

[0159] Suitable solvents include water, alkanols, glycols, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF (N,N-dimethylformamide), liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone, or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.

[0160] Absorption promoters include DMSO (dimethyl sulfoxide), isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides, fatty alcohols, and the like.

[0161] Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol, and the like.

[0162] Emulsifiable concentrates can be administered orally, transdermally, or by injection. Emulsifiable concentrates can be prepared by dissolving the active ingredient in a hydrophobic or hydrophilic phase, and homogenizing the solution with a solvent for another phase using an appropriate emulsifier, and, if necessary, with auxiliary agents such as colorants, absorption promoters, protectants, antioxidants, light-blocking agents, and thickeners.

[0163] Examples of the hydrophobic phase (oil) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglycerides, ethyl stearate, di-n-butyl adipate, hexyl laurate, dipropylene glycol pelargonate, esters of branched short-chain fatty acids with saturated fatty acids having a chain length of C16 to C18, isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols having a chain length of C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, and oleyl alcohol.

[0164] The hydrophilic phase includes water, propylene glycol, glycerin, sorbitol, and the like.

[0165] Examples of the emulsifier include nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinate, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate, and alkylphenol polyglycol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfate ether, and monoethanolamine salts of mono / dialkyl polyglycol orthophosphate esters; and cationic surfactants such as cetyltrimethylammonium chloride.

[0166] Other adjuvants include carboxymethylcellulose, methylcellulose, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, copolymers of maleic anhydride, polyethylene glycol, waxes, colloidal silica, and the like.

[0167] Semisolid preparations can be administered by painting or spreading on the skin or by introducing into body cavities. Gels can be prepared by adding to the solutions prepared as above for injectable solutions sufficient thickener to produce a clear material with an ointment-like consistency.

[0168] Next, formulation examples using the compound of the present invention are shown. However, the formulation examples of formulations containing the compound of the present invention are not limited to these. In the following formulation examples, "parts" means parts by mass.

[0169] [Wettable powder] Compound of the present invention 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts As the others, for example, an anti-caking agent, an anti-decomposition agent and the like can be mentioned.

[0170] [Emulsifiable concentrate] Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts As the other ingredients, for example, a spreading agent, a decomposition inhibitor, etc. may be mentioned.

[0171] [Suspension Agent] Compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts As the other agents, for example, antifreeze agents, thickeners and the like can be mentioned.

[0172] [Water Dispersible Granules] Compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts As the others, for example, binders, antidecomposition agents and the like can be mentioned.

[0173] [Liquid Formulation] Compound of the present invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts As the other ingredients, for example, an antifreeze agent, a spreading agent, etc. may be mentioned.

[0174] [Granules] Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts As the other ingredients, for example, a binder, a decomposition inhibitor and the like can be mentioned.

[0175] [Dust] Compound of the present invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-5 parts As the others, for example, anti-drift agents, anti-decomposition agents and the like can be mentioned.

[0176] Next, specific examples of formulations containing the compound of the present invention as an active ingredient will be shown, but the present invention is not limited to these. Note that Compound No. 1-001 of the present invention shown below means N-(4-fluorophenyl)-6-[3-(6-fluoropyridin-3-yl)-4-(trifluoromethyl)phenyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide, which is described in Synthesis Example 1 below.

[0177] [Formulation Example 1] Wettable powder Compound No. 1-001 of the present invention 20 parts Pyrophyllite 74 parts Sorpol 5039 4 parts (trade name of Toho Chemical Industry Co., Ltd., a mixture of a nonionic surfactant and an anionic surfactant) Carplex #80D 2 parts (trade name of Shionogi & Co., Ltd., synthetic hydrous silica) The above ingredients are uniformly mixed and pulverized to prepare a wettable powder.

[0178] [Formulation Example 2] Emulsifiable concentrate Compound No. 1-001 of the present invention 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Sorpol 2680 5 parts (trade name of Toho Chemical Industry Co., Ltd., a mixture of a nonionic surfactant and an anionic surfactant) The above ingredients are mixed uniformly to prepare an emulsion.

[0179] Formulation Example 3 Suspension agent Compound No. 1-001 of the present invention 25 parts Agrisol S-710 10 parts (trade name of Kao Corporation, nonionic surfactant) Lunox 1000C 0.5 parts (trade name of Toho Chemical Industry Co., Ltd., anionic surfactant) Xanthan gum 0.2 parts Water 64.3 parts The above ingredients are uniformly mixed and then wet-pulverized to obtain a suspension agent.

[0180] Formulation Example 4: Water Dispersible Granule Compound of the present invention No. 1-001 75 parts Hitenol NE-15 5 parts (trade name, Dai-ichi Kogyo Seiyaku Co., Ltd., anionic surfactant) Vanilex N 10 parts (trade name, Nippon Paper Industries Co., Ltd., anionic surfactant) Carplex #80D 10 parts (trade name, synthetic hydrous silica, Shionogi & Co., Ltd.) The above ingredients are uniformly mixed and pulverized, and then a small amount of water is added and the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give a water dispersible granule.

[0181] Formulation Example 5 Granules Compound of the present invention No. 1-001 5 parts Bentonite 50 parts Talc 45 parts After the above ingredients are uniformly mixed and pulverized, a small amount of water is added and the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give granules.

[0182] Formulation Example 6: Dust Compound of the present invention No. 1-001 3 parts Carplex #80D 0.5 parts (Shionogi & Co., Ltd. trade name, synthetic hydrous silica) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and pulverized to prepare a dust. When used, the above formulation is diluted 1 to 10,000 times with water, or sprayed directly without dilution.

[0183] Formulation Example 7 Wettable Powder Preparation Compound No. 1-001 of the present invention 25 parts Sodium diisobutylnaphthalenesulfonate 1 part Calcium n-dodecylbenzenesulfonate 10 parts Alkylaryl polyglycol ether 12 parts Sodium salt of naphthalenesulfonic acid formalin condensate 3 parts Emulsion-type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts

[0184] Formulation Example 8: Water-soluble thickener preparation Compound No. 1-001 of the present invention 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-propanol 36.5 parts

[0185] Formulation Example 9: Spray liquid Compound of the present invention No. 1-001 2 parts Dimethyl sulfoxide 10 parts 2-propanol 35 parts Acetone 53 parts

[0186] Formulation Example 10: Liquid preparation for transdermal administration Compound No. 1-001 of the present invention 5 parts Hexylene glycol 50 parts 2-propanol 45 parts

[0187] Formulation Example 11: Liquid preparation for transdermal administration Compound No. 1-001 of the present invention 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts

[0188] Formulation Example 12: Liquid preparation for transdermal administration (dropping) Compound of the present invention No. 1-001 2 parts Light liquid paraffin 98 parts

[0189] Formulation Example 13: Liquid preparation for transdermal administration (dropping): Compound No. 1-001 of the present invention 2 parts, Light liquid paraffin 58 parts, Olive oil 30 parts, O.D.O 9 parts (product name of Nisshin Oillio Group, medium-chain fatty acid oil), Shin-Etsu Silicone 1 part

[0190] Furthermore, when the compound of the present invention is used as an agricultural chemical or veterinary drug, it may be mixed with other chemicals at the time of formulation or application, if necessary. By applying the compound in a mixed state, costs can be reduced by reducing the amount of chemicals applied, and the control spectrum can be expanded and a higher pest control effect can be achieved by the synergistic action of the mixed chemicals. In this case, it is also possible to combine the compound with multiple known chemicals at the same time.

[0191] For example, types of pesticides that can be mixed with the compound of the present invention include compounds described in The Pesticide Manual, 18th Edition, 2018 and The Pesticide Manual, 19th Edition, 2021. Specific examples of the common names of antiparasitic drugs and antibiotics that can be mixed and used as veterinary drugs are as follows, but are not necessarily limited to these.

[0192] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, Bacillus thuringiensis thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin smethrin), bistrifluron, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionate, chlorantraniliprole, chlorethoxyfos,Chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin halothrin), cyhexatin (cyhexatine), cypermethrin (cypermethrin), cyphenothrin (cyphenothrin), cyproflanilide (cyproflanilide), cyromazine (cyromazine), deltamethrin (deltamethrin), diacloden (diacloden), diafenthiuron (diafenthiuron), diazinon (diazinon), dichlorvos (dichlorvos), dichloromezotiaz (dicloromezotiaz), Dicofol (dicofol), dienochlor (dienochlor), diflovidadin (diflovidazin), diflubenzuron (diflubenzuron), dimefluthrin (dimefluthrin), dimethoate (dimethoate), dimethylvinphos (dimethylvinphos), dimpropyridaz (dimpropyridaz), dinotefuran (dinotefuran), diofenolan (diofenolan), disulfoton (disulfoton), DNOC (DNOC),d-T-80-phthalthrin, emamectin benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethifencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, Rubendiamide (flubendiamide), fluchlordiniliprole (fluchlorodiniliprole), flucycloxuron (flucycloxuron), flucythrinate (flucythrinate), flufenerim (flufenerim), flufenoxuron (flufenoxuron), flufenprox (flufenprox), flufiprole (flufiprole), fluhexafon (fluhexafon), flumethrin (flumethrin), flupentiofenox (flupentiofenox), flupyradifurone (flupyradifurone), flupyrimin (flupyrimin),Flupyroxystrobin, fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide halofenozide), heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloceram ocycloseram), isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, ledprona, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide bromide), metofluthrin,Milbemectin, momfluorothrin, monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb ), pirimiphos-methyl, praziquantel, profenofos, profluthrin, propaphos, propargite, prothiofos, protrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole afluprole), pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spidoxamat, spinetoram,Spinosad (spinosad), spirobudifen (spirobudifen), spirodiclofen (spirodiclofen), spiromesifen (spiromesifen), spiropidione (spiropidion), spirotetramate (spirotetramat), spiromesifen (spyromesifen), sulfiflumin (sulfiflumin), sulfotep (sulfotep), sulfoxaflor (sulfoxaflor), sulprofos (sulprofos), tau-fluvalinate (tau-fluvalinate), tebufenozide (tebfenozide), tebufenpyrad (tebufenpyrad), teflubenzuron (teflubenzuron), tefluthrin (tefluthorin), terbufos (terbufos), tetrachlorantraniliprole (tetrachlorantraniliprole), tetrachlorvinphos (tetrachlorvinphos), tetramethrin (tetramethrin), Tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, thioantraniliprole, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, zeta-cypermethrin and the like.

[0193] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide polysulfide), benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorph, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture mixture), boscalid (boscalid), bromoconazole (bromoconazole), bupirimate (bupirimate), buthiobate (buthiobate), butylamine (butylamine), lime sulfur mixture (calcium polysulfide), captafol (captafol), captan (captan), carbamorph (carbamorph), carbendazim (carbendazim), carboxin (carboxin), carpropamid (carpropamid), carvone (carvone), cheshunt mixture (cheshunt mixture), chinomethionate (chinomethionat),Chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloroinconazide, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate chromate), coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetate acid), dichlobentiazox, dichlofluanid, diclone, dichlorophen, dichlozoline, diclobutrazol,Diclocymet (diclocymet), diclomezine (diclomezine), dicloran (dicloran), diethofencarb (diethofencarb), difenoconazole (difenoconazole), diflumetorim (diflumetorim), dimethirimol (dimethirimol), dimethomorph (dimethomorph), dimoxystrobin (dimoxystrobin), diniconazole (diniconazole), diniconazole-M (diniconazole-M), Dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbone, diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon n), DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etri diazole (etridiazole), famoxadone (famoxadone), fenamidone (fenamidone), fenaminosulf (fenaminosulf), phenaminestrobin (fenaminstrobin), fenapanil (fenapanil), fenarimol (fenarimol), fenbuconazole (fenbuconazole), fenfuram (fenfuram), fenhexamid (fenhexamid), fenitropan (fenitropan), fenoxanil (fenoxanil),Fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, flubeneteram, fludioxonil ioxonil), flufenoxadiazam (flufenoxadiazam), flufenoxystrobin (flufenoxystrobin), fluindapyr (fluindapyr), flumetylsulforim (flumetylsulforim), flumetover (flumetover), flumorph (flumorph), fluopicolide (fluopicolide), fluopimomide (fluopimomide), fluopyram (fluopyram), fluoroimide (fluoroimide), fluoto Rimazole (fluotrimazole), fluoxapiprolin (fluoxapiprolin), fluoxastrobin (fluoxastrobin), fluoxytioconazole (fluoxytioconazole), fluquinconazole (fluquinconazole), flusilazole (flusilazole), flusulfamide (flusulfamide), flutolanil (flutolanil), flutianil (flutianil), flutriafol (flutriafol), fluxapyroxad (fluxapyroxad), folpet (folpet), fosetyl - aluminum (fosetyl-aluminium), fthalide (fthalide), fuberidazole (fuberidazole), furalaxyl (furalaxyl), furametpyr (furametpyr), furcarbanil (furcarbanil), fluconazole (furconazole), fluconazole - cis (furconazole-cis), flumecyclox (furmecyclox), furophanate (furophanate),Glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, oxyquinoline sulfate (8-hydroxyquinoline sulfate), hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isofetamide, isoflucypram, isotianil, isoprothiolane isoprothiolane), isopyrazam (isopyrazam), isovaledione (isovaledione), kasugamycin (kasugamycin), kresoxim-methyl (kresoxim-methyl), laminarin (laminarin), mancopper (mancopper), mancozeb (mancozeb), mandestrobin (mandestrobin), mandipropamid (mandipropamid), maneb (maneb), mebenil (mebenil), mecarbinzid (mecarbinzid), mefentrifluconazole (mefentrifluconazole), mepanipyrim (mepanipyrim), mepronil (mepronil), meptyldinocap (meptyldinocap), metalaxyl (metalaxyl), metalaxyl -M (metalaxyl-M), metam (metam),metarylpicoxamid, metazoxolone, metconazole, methasulfocarb, metofuroxam, methyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, organic nickel (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxyquinoline copper, oxpoconazole fumarate fumarate), oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, orthophenylphenol (2-phenylphenol), phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxin-D, potassium azide,Potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride), propiconazole, propineb, proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoin, pyraziflumid pyraziflumid), pyridaclomethyl (pyridachlometyl), pyridinitril (pyridinitril), pyriophenone (pyriofenone), pyrisoxazole (pyrisoxazole), pyroxychlor (pyroxychlor), pyroxyfur (pyroxyfur), quinacetol - sulfate (quinacetol-sulfate), quinazamid (quinazamid), quinconazole (quinconazole), quinoxyfen (quinoxyfen), quinofumelin (quinofumelin), quintozene (quintozene), rabenzazole (rabenzazole), salicylanilide (salicylanilide), seboctylamine (seboctylamine), sedaxane (sedaxane), silthiofam (silthiofam), simeconazole (simeconazole), sodium hydrogen carbonate (sodium hydrogen carbonate),Sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tefloctalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate e), thiophanate-methyl, thiuram, tiadinil, tioximid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide oxide), trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zalilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide,Shiitake mycelium extract and shiitake fruiting body extract, etc.

[0194] Nematicides: aldoxycarb, benclothiaz, cadusafos, cyclobutrifluram, DBCP, diclofenthion, DSP, ethoprophos, fenamiphos, fensulfothion, fluazaindolizine, fluensulfone, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos, oxamyl, thionazin, tioxazafen, trifluenfuronate, and the like.

[0195] Parasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin fluthrin), zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, Pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos , ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenocarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,Tigolaner (tigolaner), esafoxolaner (esafoxolaner), modoflaner (modoflaner), umifoxolaner (umifoxolaner), mivorilaner (mivorilaner), avermectin (avermectin), ivermectin (ivermectin), doramectin (doramectin), eprinomectin (eprinomectin), madeuramycin (maduramycin), milbemycin (milbemycin), milbemycin oxime (milbemycin oxime), moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide), emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsomine dihydrochloride,metronidazole, methylidine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, and triclabendazole, etc.

[0196] Antibiotics: amoxicillin, ampicillin, cefapirin, cefazolin sodium, cefquinome, ceftiofur, penicillin, chlortetracycline, oxytetracycline, danofloxacin, difloxacin, oxolinic acid acid), enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, norfloxacin, ofloxacin, orbifloxacin, valnemulin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, tylosin acetate isovalerate, tylosin phosphate, tulathromycin, ketoconazole, miconazole nitrate nitrate and clavulanic acid, etc.

[0197] The compounds of the present invention have excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, and internal or external parasites of mammals or birds, and also exhibit sufficient control effects against pests that have acquired resistance to existing insecticides. Furthermore, they have almost no adverse effects on mammals, fish, and beneficial insects, and are low-residual and have a low environmental impact. Therefore, the present invention can provide a useful novel pest control agent.

[0198] In light of the above, embodiments of the present invention relate to the following [1] to

[83] . [1] Formula (1): [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-2 9, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56; Z １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, halo (C ２ ~C ６ ) alkenyl, halo(C ２ ~C ６ ) alkynyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkoxy (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkenyloxy, halo(C ２ ~C ６ ) alkenyloxy, C ２ ~C ６ Alkynyloxy, halo(C ２ ~C ６ ) alkynyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C１ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, C ２ ~C ６ Alkenylthio, C ２ ~C ６ Alkenylsulfinyl, C ２ ~C ６ Alkenylsulfonyl, halo(C ２ ~C ６ ) alkenylthio, halo(C ２ ~C ６ ) alkenylsulfinyl, halo(C ２ ~C ６ ) alkenylsulfonyl, C ２ ~C ６ Alkynylthio, C ２ ~C ６ Alkynylsulfinyl, C ２ ~C ６ Alkynylsulfonyl, halo(C ２ ~C ６ ) alkynylthio, halo(C ２ ~C ６ ) alkynylsulfinyl, halo(C ２ ~C ６ ) alkynylsulfonyl, —NH ２ , C １ ~C ６ Alkylamino, di(C １ ~C ６ ) alkylamino, halo(C １ ~C ６ ) alkylamino, dihalo (C １ ~C ６ ) alkylamino, formyl, carboxy, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, halo(C １ ~C ６) alkoxycarbonyl, C １ ~C ６ alkylaminocarbonyl, halo(C １ ~C ６ ) alkylaminocarbonyl, di(C １ ~C ６ ) alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkoxycarbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo(C １ ~C ６ ) alkylsulfonyloxy, —SO ３ H, C １ ~C ６ Alkylaminosulfonyl, di(C １ ~C ６ ) alkylaminosulfonyl, —C(═NOR １２ ) R １３ , cyano or nitro; R １２ is a hydrogen atom or C １ ~C ６ represents alkyl, R １３ is a hydrogen atom or C １ ~C ６ represents alkyl; Z ３ is a hydrogen atom or C １ ~C ６ alkyl, J represents J-1 or J-2, A １represents a nitrogen atom or CH, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G- 32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-4 7, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, halo (C ２ ~C ６ ) alkenyl, halo(C ２ ~C ６ ) alkynyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkoxy (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkenyloxy, halo(C ２ ~C ６ ) alkenyloxy, C ２ ~C ６ Alkynyloxy, halo(C ２ ~C ６ ) alkynyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, C ２ ~C ６ Alkenylthio, C ２ ~C ６ Alkenylsulfinyl, C ２ ~C ６ Alkenylsulfonyl, halo(C ２ ~C ６ ) alkenylthio, halo(C ２ ~C ６ ) alkenylsulfinyl, halo(C ２ ~C ６ ) alkenylsulfonyl, C ２ ~C ６ Alkynylthio, C ２ ~C ６ Alkynylsulfinyl, C ２ ~C ６ Alkynylsulfonyl, halo(C ２ ~C ６ ) alkynylthio, halo(C ２ ~C ６ ) alkynylsulfinyl, halo(C ２ ~C ６ ) alkynylsulfonyl, —NH ２ , C １ ~C ６ Alkylamino, di(C １ ~C ６ ) alkylamino, halo(C １ ~C ６ ) alkylamino, dihalo (C １ ~C ６ ) alkylamino, formyl, carboxy, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, halo(C １ ~C ６ ) alkoxycarbonyl, C １~C ６ alkylaminocarbonyl, halo(C １ ~C ６ ) alkylaminocarbonyl, di(C １ ~C ６ ) alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkoxycarbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo(C １ ~C ６ ) alkylsulfonyloxy, —SO ３ H, C １ ~C ６ Alkylaminosulfonyl, di(C １ ~C ６ ) alkylaminosulfonyl, —C(═NOR １４ ) R １５ , nitro or cyano; R １４ is a hydrogen atom or C １ ~C ６ represents alkyl, R １５ is a hydrogen atom or C １ ~C ６ represents alkyl; Z ４ is C １ ~C ６ represents alkyl, R １ represents a hydrogen atom, a halogen atom, a halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkyl or cyano; R ２ is a hydrogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ cycloalkyl, —C(O)R ４ , -C(O)OR ５ , D-1, D-2 or D-3; R ４ is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkylcarbonyl, di(C １ ~C ６ ) alkylamino or R ６ (C １ ~C ６ ) alkyl, R ６ is a halogen atom, C １ ~C ６ Alkoxy, cyano, nitro, phenyl or R ８ represents phenyl substituted with ５ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R ８ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R ５ is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, R ９ (C １ ~C ６ ) alkyl, phenyl or R １０ represents phenyl substituted with R ９ is a halogen atom, C １ ~C ６ Alkoxy, cyano, nitro, phenyl or R １１ represents phenyl substituted with R １０ is a halogen atom, C１ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R １１ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy, cyano or nitro; R ３ is a hydrogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl or C １ ~C ６ [2] A represents an alkylcarbonyl, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, t5 represents an integer of 0, 1, 2, 3, 4 or 5, and t8 represents an integer of 0, 1, 2, 3 or 4. [2] A １ [3] The aryltetrahydropyridine compound or salt thereof according to the above [1], wherein Z represents a nitrogen atom. １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, —NH ２ , C １ ~C ６ Alkylamino, di(C １ ~C ６ ) alkylamino, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ ) alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ represents alkylsulfonyloxy, cyano or nitro; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, halo (C ２ ~C ６ ) alkenyl, halo(C ２ ~C ６ ) alkynyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, —NH ２ , C １ ~C ６ Alkylamino, di(C １ ~C ６ ) alkylamino, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ ) alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylsulfonyloxy, —C(═NOR １４ ) R １５ , nitro or cyano; Z ５ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ２ is a hydrogen atom, -C(O)R ４ , -C(O)OR ５ , D-1, D-2 or D-3; R ３represents a hydrogen atom; Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52 or Q-54; G is G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G- 16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30 [4] J represents J-1, and A represents G-31, G-32, G-33, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-54, G-55, or G-57, or a salt thereof. １[5] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [3], wherein J represents a nitrogen atom. [6] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [3], wherein J represents J-2. [6] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [5], wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55, or G-57. [7] Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52; Z １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６represents alkylaminocarbonyl, hydroxy, cyano or nitro, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40, Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ ) alkylamino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, hydroxy, -C(=NOR １４ ) R １５ , nitro or cyano; R １４ is C １ ~C ６ represents alkyl, R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ２ is a hydrogen atom, -C(O)R ４ , -C(O)OR ５ , D-1, D-2 or D-3; R ４ is C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkylcarbonyl or R ６ (C１ ~C ６ ) alkyl, R ６ is a halogen atom or C １ ~C ６ represents alkoxy; Z ５ is C １ ~C ６ represents alkyl, R ５ is C １ ~C ６ Alkyl or C ２ ~C ６ represents alkenyl, R ３ represents a hydrogen atom, X represents an oxygen atom. [8] The aryl tetrahydropyridine compound or a salt thereof according to the above [1], wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40. [9] Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, or Q-45, and Z １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ represents alkoxycarbonyl, cyano or nitro; Z ３ is C １ ~C ６ represents alkyl; Z ２ is a halogen atom, C１ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６

[10] The aryltetrahydropyridine compound or a salt thereof according to the above [8], wherein J represents J-1, and A represents alkylsulfonyl, hydroxy, nitro, or cyano. １ represents a nitrogen atom; Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-12, Q-13, Q-14 or Q-22; G represents G-1, G-3, G-4 or G-5; Z ２ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) represents alkoxy or nitro, R ２ represents a hydrogen atom or —C(O)OR ５ represents R ５ is C １ ~C ６

[11] The aryltetrahydropyridine compound or a salt thereof according to the above [9], wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12, and Z represents an alkyl group, and Y represents an oxygen atom. １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, cyano or nitro; G represents G-1 or G-3; Z ２ is a halogen atom, C １ ~C ６ Alkyl or halo(C１ ~C ６ ) alkyl, R １ is a halogen atom or halo(C １ ~C ６ ) alkyl, R ２

[12] The aryltetrahydropyridine compound or a salt thereof according to the above

[10] , wherein J represents J-2, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, Q-12, Q-20, Q-29 or Q-45, and Z １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ G represents G-1, G-3, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40; Z ２ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６

[13] The aryltetrahydropyridine compound or a salt thereof according to the above

[11] , wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, or Q-12, and Z represents alkylsulfonyl or hydroxy. １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, cyano or nitro; G represents G-1, G-3 or G-7; Z ２is a halogen atom, C １ ~C ６ Alkyl or halo(C １ ~C ６ ) alkyl, R ２

[14] The aryl tetrahydropyridine compound or salt thereof according to the above [1] to [6], wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-11, Q-14, Q-15, Q-16, Q-17, or Q-18.

[15] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [8], wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-11, or Q-14.

[16] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to

[13] , wherein Q represents Q-1.

[17] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [6], wherein Q represents Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-14, Q-15, Q-16, Q-17, or Q-18.

[18] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [9], wherein Q represents Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, or Q-14.

[19] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [6], wherein Q represents Q-9, Q-10, Q-12, Q-13, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52, or Q-54.

[20] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [8], wherein Q represents Q-9, Q-12, Q-13, Q-20, Q-22, Q-31, Q-45, or Q-52.

[21] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [6], wherein Q represents Q-12, Q-30, Q-31, Q-32, Q-33, Q-40, Q-45, Q-47, Q-49, Q-52, Q-55, or Q-56.

[22] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [8], wherein Q represents Q-31, Q-45, or Q-52.

[23] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [6], wherein Q represents Q-9, Q-13, Q-25, Q-26, Q-27, Q-29, Q-39, Q-42, Q-44, Q-46, Q-51, or Q-54.

[24] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [8], wherein Q represents Q-9 or Q-13.

[25] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [6], wherein Q represents Q-10, Q-19, Q-20, Q-21, Q-22, Q-23, Q-38, Q-41, Q-43, or Q-50.

[26] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [8], wherein Q represents Q-10, Q-20, or Q-22.

[27] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [8], wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, or Q-12.

[28] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to

[13] , wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, or Q-12.

[29] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to

[13] , wherein Q represents Q-1, Q-2, Q-3, Q-4, or Q-6.

[30] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [8], wherein Q represents Q-9, Q-10, or Q-12.

[31] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to

[13] , wherein Q represents Q-9 or Q-12.

[32] Z. １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, halo (C２ ~C ６ ) alkenyl, halo(C ２ ~C ６ ) alkynyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkoxy (C １ ~C ６ ) alkoxy, C ２ ~C ６ Alkenyloxy, halo(C ２ ~C ６ ) alkenyloxy, C ２ ~C ６ Alkynyloxy, halo(C ２ ~C ６ ) alkynyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, C ２ ~C ６ Alkenylthio, C ２ ~C ６ Alkenylsulfinyl, C ２ ~C ６ Alkenylsulfonyl, halo(C ２ ~C ６ ) alkenylthio, halo(C ２ ~C ６ ) alkenylsulfinyl, halo(C ２ ~C ６ ) alkenylsulfonyl, C ２ ~C ６ Alkynylthio, C ２ ~C ６ Alkynylsulfinyl, C ２ ~C ６ Alkynylsulfonyl, halo(C ２~C ６ ) alkynylthio, halo(C ２ ~C ６ ) alkynylsulfinyl, halo(C ２ ~C ６

[33] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [2] and

[14] to

[31] , wherein Z represents alkynylsulfonyl, cyano, or nitro. １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, —NH ２ , C １ ~C ６ Alkylamino, di(C １ ~C ６ ) alkylamino, halo(C １ ~C ６ ) alkylamino, dihalo (C １ ~C ６ ) alkylamino, formyl, carboxy, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, halo(C １ ~C ６ ) alkoxycarbonyl, C １ ~C ６ alkylaminocarbonyl, halo(C １ ~C ６ ) alkylaminocarbonyl, di(C １ ~C ６

[34] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to [2] and

[14] to

[31] , wherein Z represents alkylaminocarbonyl, cyano, or nitro. １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６

[35] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to

[13] , wherein Z represents alkyl, cyano, or nitro. １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６

[36] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[13] , wherein Z represents alkyl or cyano. ３ is C １ ~C ６

[37] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[35] above, wherein Z represents alkyl. ３

[38] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[35] , wherein G represents a hydrogen atom. , G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61.

[39] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [2] and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-6, G-7, G-8, G-11, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61.

[40] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [6] and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-7, G-11, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-32, G-34, G-35, G-36, G-37, G-38, G-47, G-48, G-50, G-53, G-55, or G-57.

[41] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [5], [7], and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-6, G-7, G-8, G-11, G-17, or G-19.

[42] The aryl tetrahydropyridine compound or a salt thereof according to any one of the above [1] to [9] and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-7, G-11, G-17, or G-19.

[43] The aryl tetrahydropyridine compound or a salt thereof according to any one of the above [1] to [9],

[12] , and

[14] to

[37] , wherein G represents G-1, G-3, G-7, G-11, G-17, or G-19.

[44] The aryl tetrahydropyridine compound or a salt thereof according to any one of the above [1] to [5] and

[14] to

[37] , wherein G represents G-1, G-2, G-3, G-5, G-7, G-11, G-17, G-18, G-19, G-20, G-21, G-22, G-23, or G-24.

[45] The aryl tetrahydropyridine compound or a salt thereof according to any one of the above [1] to [7] and

[14] to

[37] , wherein G represents G-1, G-2, G-3, G-5, G-7, G-11, G-17, or G-19.

[46] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [9] and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-7, G-11, G-17, or G-19.

[47] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [9],

[12] , and

[14] to

[37] , wherein G represents G-1, G-3, G-7, G-11, G-17, or G-19.

[48] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to [9],

[12] , and

[14] to

[37] , wherein G represents G-1, G-3, or G-7.

[49] The aryl tetrahydropyridine compound or salt thereof according to any one of the above [1] to

[37] , wherein G represents G-1 or G-3.

[50] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[49] , wherein t1 represents an integer of 0, t2 represents an integer of 0, t3 represents an integer of 0 or 1, t4 represents an integer of 0, 1 or 2, and t5 represents an integer of 0 or 1.

[51] Q represents Q-2, Q-3, Q-4, Q-6, Q-9, Q-12 or Q-14, and Z. １ is a halogen atom or C １ ~C６ represents alkyl; Z ３ is C １ represents alkyl, J represents J-1 or J-2, １ represents a nitrogen atom; G represents G-1, G-3 or G-7; Z ２ represents a halogen atom; １ is a halogen atom or halo(C １ ~C ６ ) alkyl, R ２ represents a hydrogen atom; ３ represents a hydrogen atom, X represents an oxygen atom, Y represents an oxygen atom, t2 represents an integer of 0, and t4 represents an integer of 0, 1, or 2.

[52] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[50] , wherein Q represents Q-2, Q-3, Q-4, Q-6, Q-9, or Q-12, and Z １ is a halogen atom or C １ ~C ６ represents alkyl; Z ３ is C １ represents alkyl, J represents J-1, A １ represents a nitrogen atom, G represents G-1 or G-3, Z ２ represents a halogen atom; １ is a halogen atom or halo(C １ ~C ６ ) alkyl, R ２ represents a hydrogen atom; ３ represents a hydrogen atom, X represents an oxygen atom, Y represents an oxygen atom, t2 represents an integer of 0, and t4 represents an integer of 0, 1, or 2.

[53] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[50] , wherein Q represents Q-2, Q-3, Q-4, Q-6, Q-9, or Q-12, and Z １ is a halogen atom or C １ ~C ６ represents alkyl; Z ３ is C １ J represents J-2; G represents G-1 or G-3; Z２ represents a halogen atom; １ is a halogen atom or halo(C １ ~C ６ ) alkyl, R ２ represents a hydrogen atom; ３ represents a hydrogen atom, X represents an oxygen atom, Y represents an oxygen atom, t2 represents an integer of 0, and t4 represents an integer of 0, 1, or 2.

[54] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[53] , wherein R represents a hydrogen atom, X represents an oxygen atom, Y represents an oxygen atom, t2 represents an integer of 0, and t4 represents an integer of 0, 1, or 2.

[55] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[53] , wherein R １ is a halogen atom or halo(C １ ~C ６

[56] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to

[54] , wherein R represents alkyl. ２ is a hydrogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, —C(O)R ４ or -C(O)OR ５ represents R ４ is C １ ~C ６ represents alkyl, R ５ is C １ ~C ６

[57] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to

[50] , wherein R represents alkyl. ２ is a hydrogen atom or C １ ~C ６

[58] The aryltetrahydropyridine compound or a salt thereof according to the above

[56] , wherein R represents alkyl. ２

[59] The aryltetrahydropyridine compound or salt thereof according to the above

[57] , wherein R represents a hydrogen atom. ３

[60] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to

[59] , wherein X represents an oxygen atom, and Y represents an oxygen atom.

[61] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to

[59] , wherein X represents an oxygen atom, and Y represents an oxygen atom.

[62] The aryltetrahydropyridine compound or salt thereof according to any one of the above [1] to

[59] , wherein X represents an oxygen atom, and Y represents an oxygen atom. [In the formula, Q represents Q-1, Q-2, Q-3 or Q-4, Z １ represents a halogen atom, halo(C １ ~C ６ ) alkyl or cyano; G represents G-1; Z ２ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkoxy or cyano; R １ is a halogen atom or halo(C １ ~C ６ ) alkyl, R ２ represents a hydrogen atom; ３ represents a hydrogen atom; １ represents a nitrogen atom or CH, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5. ] or a salt thereof.

[62] Q represents Q-1, Z １ represents a halogen atom; Z ２ is a halogen atom or C １ ~C ６

[63] An aryltetrahydropyridine compound or a salt thereof according to the above

[61] , wherein X represents an oxygen atom, Y represents an oxygen atom, t4 represents an integer of 1, and t5 represents an integer of 1.

[63] An aryltetrahydropyridine compound or a salt thereof according to the above

[61] , [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6 or Q-7, Z１ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio or cyano; G represents G-1, G-2, G-3, G-4, G-5 or G-6; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, nitro or cyano; R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ２ is a hydrogen atom, C １ ~C ６ Alkyl or C ２ ~C ６ represents alkynyl, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, １represents a nitrogen atom or CH, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.

[64] An aryltetrahydropyridine compound or a salt thereof represented by the following formula: １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio or cyano; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, nitro or cyano; R ２ represents a hydrogen atom; ３

[65] The aryltetrahydropyridine compound or salt thereof according to the above

[63] , wherein X represents an oxygen atom, and Y represents an oxygen atom. [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, or Q-8, Z １ is a halogen atom, C １~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio or cyano, J represents J-1 or J-2, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8 or G-9; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, nitro or cyano; R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ２ is a hydrogen atom, C １ ~C ６ Alkyl or C ２ ~C ６ represents alkynyl, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, １represents a nitrogen atom or CH, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.

[66] An aryltetrahydropyridine compound or a salt thereof, １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio or cyano; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, nitro or cyano; R ２ represents a hydrogen atom; ３

[67] The aryltetrahydropyridine compound or salt thereof according to the above

[65] , wherein X represents an oxygen atom, and Y represents an oxygen atom. [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 or Q-9, Z １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, cyano or nitro, J represents J-1 or J-2, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8 or G-9; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, nitro or cyano; R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ２ is a hydrogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkynyl or C １ ~C ６represents an alkoxycarbonyl; R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, １ represents a nitrogen atom or CH, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.

[68] An aryltetrahydropyridine compound or a salt thereof, １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio or cyano; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, nitro or cyano; R ２ represents a hydrogen atom; ３

[69] The aryltetrahydropyridine compound or salt thereof according to the above

[67] , wherein X represents an oxygen atom, and Y represents an oxygen atom. [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12 or Q-13, Z １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, hydroxy, cyano or nitro, J represents J-1 or J-2, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16 or G-17; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C１ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, hydroxy, nitro or cyano; R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ２ is a hydrogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, —C(O)R ４ or -C(O)OR ５ represents R ４ is C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkylcarbonyl or R ６ (C ａ ~C ｂ ) alkyl, R ６ is a halogen atom or C １ ~C ６ represents alkoxy, R ５ is C １ ~C ６ Alkyl or C ２ ~C ６ represents alkenyl, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, １ represents a nitrogen atom or CH, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.

[70] An aryltetrahydropyridine compound or a salt thereof, ２ is a halogen atom, C １ ~C ６Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ represents alkylcarbonyl, hydroxy, nitro or cyano; R ２ is a hydrogen atom, -C(O)R ４ or -C(O)OR ５ represents R ３ represents a hydrogen atom, X represents an oxygen atom, and Y represents an oxygen atom.

[71] An aryltetrahydropyridine compound or a salt thereof according to the above

[69] , wherein [In the formula, J represents J-1 or J-2, A １ represents a nitrogen atom; G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40; Z ２ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６) alkylamino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, hydroxy, -C(=NOR １４ ) R １５ , nitro or cyano; R １４ is C １ ~C ６ represents alkyl, R １５ is a hydrogen atom or C １ ~C ６ represents alkyl; Z ４ is C １ ~C ６ represents alkyl, R １ represents a hydrogen atom, a halogen atom, or a halo(C １ ~C ６ ) alkyl, R ５１ is C １ ~C ６

[72] J represents J-1, G represents G-1, G-2 or G-3, Z represents an alkyl, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.

[73] A compound according to any one of [1] to

[72] , wherein J represents J-1, G represents G-1, G-2 or G-3, Z represents an alkyl, t3 represents an integer of 0, 1 or 2, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5. ２ is a halogen atom or C １ ~C ６ represents alkyl, R １ is a halogen atom or halo(C １ ~C ６

[73] An intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to the above

[71] , wherein R represents an alkyl group represented by the formula (1-2): [In the formula, R ５２ is a hydrogen atom or C １ ~C ６ represents alkyl, R ２ is a hydrogen atom, -C(O)R ４ or -C(O)OR ５ represents R ４ is C １ ~C ６represents alkyl, R ５ is C １ ~C ６ Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52; Z １ is a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylthio, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ represents alkylaminocarbonyl, hydroxy, cyano or nitro; Z ３ is a hydrogen atom or C １ ~C ６

[74] Q represents Q-1, Q-2, Q-3, Q-4, Q-6 or Q-9, Z represents an alkyl, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.

[75] Q represents Q-1, Q-2, Q-3, Q-4, Q-6 or Q-9, Z represents an alkyl, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5. １is a halogen atom, C １ ~C ６ represents alkyl or cyano; R ２ represents a hydrogen atom or —C(O)OR ５

[75] A production intermediate of the aryl tetrahydropyridine compound or salt thereof according to the above

[73] , which represents:

[76] A pest control agent containing, as an active ingredient, one or more selected from the aryl tetrahydropyridine compounds and salts thereof according to any one of the above [1] to

[70] .

[77] An agent for controlling endo- or ectoparasites of mammals or birds, which contains, as an active ingredient, one or more selected from the aryl tetrahydropyridine compounds and salts thereof according to any one of the above [1] to

[70] .

[78] The control agent according to the above

[77] , wherein the ectoparasite is of the order Siphonaptera or the order Acarina.

[79] An insecticide or acaricide containing, as an active ingredient, one or more aryltetrahydropyridine compounds selected from the aryltetrahydropyridine compounds and salts thereof described in any one of [1] to

[70] above.

[80] A seed treatment agent containing, as an active ingredient, one or more aryltetrahydropyridine compounds selected from the aryltetrahydropyridine compounds and salts thereof described in any one of [1] to

[70] above.

[81] The seed treatment agent according to

[80] above, in which the seed treatment is carried out by a dipping treatment.

[82] A soil treatment agent containing, as an active ingredient, one or more aryltetrahydropyridine compounds selected from the aryltetrahydropyridine compounds described in any one of [1] to

[70] above.

[83] The soil treatment agent according to

[82] above, in which the soil treatment is carried out by a soil drench treatment.

[0199] The present invention will be explained in more detail below by describing examples of synthesis and testing of the compounds of the present invention, but the present invention is not limited to these examples.

[0200] The medium pressure preparative liquid chromatography described in the synthesis examples was carried out using a medium pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).

[0201] In addition, the proton nuclear magnetic resonance spectrum described below (hereinafter, １ The chemical shift values ​​of H-NMR are expressed as Me as a standard substance. ４ Using Si (tetramethylsilane), measurements were carried out in a deuterated chloroform solvent at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). １ The symbols in the H-NMR chemical shift values ​​have the following meanings: s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, brs: broad singlet

[0202] Synthesis Example 1: Synthesis of N-(4-fluorophenyl)-6-[3-(6-fluoropyridin-3-yl)-4-(trifluoromethyl)phenyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (Compound of the Invention No. 1-001) To a mixed solution of 94 mg of 6-[3-bromo-4(trifluoromethyl)phenyl]-N-(4-fluorophenyl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide, 1.6 ml of 1,4-dioxane, and 0.4 ml of water, 42 mg of 2-fluoropyridine-5-boronic acid, 83 mg of potassium carbonate, and 16 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride dichloromethane adduct were added, and the mixture was stirred at 90° C. for 5 hours under a nitrogen atmosphere. After the reaction was completed, 5 ml of 1 mol / l hydrochloric acid was added, and the mixture was extracted with ethyl acetate (5 ml x 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by medium-pressure preparative liquid chromatography [n-hexane:ethyl acetate = gradient from 100:0 to 0:100 (volume ratio, the same applies hereinafter)] to obtain 31 mg of the target product as a white solid. Melting point: 200-202°C 1H-NMR (300MHz):δ11.5-12.0(m, 1H), 8.18(brs, 1H), 7.85(d, J=8.7Hz, 1H), 7.65-7.8(m, 1H), 7.4-7.65(m, 4H), 7.33(brs, 1H), 6.95-7.1(m, 3H), 5.45-5.7(m, 1H), 4.8-5.0(m, 1H), 2.75-3.0(m, 2H).

[0203] Synthesis Example 2: Synthesis of 6'-chloro-N-(4-chlorophenyl)-6''-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3''-terpyridine]-5-carboxamide (Invention Compound No. 2-035) To a mixed solution of 100 mg of ethyl 6'-chloro-6''-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3''-terpyridine]-5-carboxylate and 0.7 ml of 1,4-dioxane, 32 mg of 4-chloroaniline was added and stirred at 80°C for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The resulting residue was washed with a mixed solution of ethyl acetate:n-hexane=1:2 to obtain 41 mg of the target product as a pale brown solid. Melting point: 199-201°C 1 H-NMR (300MHz):δ11.6(brs, 1H), 8.48(brs, 1H), 8.29(brs, 1H), 7.85-8.0(m, 1H), 7.65-7.8(m, 1H), 7.4-7.6(m, 2H), 7.25-7.35(m, 2H), 7.05-7.15(m, 2H), 5.3-5.8(m, 1H), 4.85-4.95(m, 1H), 2.7-3.05(m, 2H).

[0204] Synthesis Example 3: Synthesis of N-(5-fluoropyridin-2-yl)-6-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (Invention Compound No. 3-036) To a mixed solution of 50 mg of 6-(((2-fluoroisonicotinimidamido)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide and 1.7 ml of toluene, 17 mg of triethylamine was added, and the mixture was stirred at 110°C for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 5 ml of 1 mol / l hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate (5 ml x 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. 1 ml of N,N-dimethylformamide, 3 ml of water, and 1 ml of 1 mol / l hydrochloric acid were added to the obtained residue. The precipitated solid was collected by filtration to obtain 39 mg of the target product as a white solid. Melting point: 159-161°C

[0205] The synthesis examples of the intermediates used in Synthesis Example 2 for the compounds of the present invention are described below.

[0206] Intermediate Synthesis Example 1: Synthesis of ethyl 6'-chloro-6"-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3"-terpyridine]-5-carboxylate Step 1: Synthesis of ethyl 3-(5-bromo-6-chloropyridin-3-yl)-3-(3-ethoxy-3-oxopropanamido)propanoate To a mixed solution of 13 g of ethyl 3-amino-3-(5-bromo-6-chloropyridin-3-yl)propanoate, 142 ml of ethyl acetate, 7.2 g of sodium bicarbonate, and 142 ml of water, 6.7 g of ethyl malonyl chloride was added at 0°C. After completion of the reaction, the resulting organic layer was dehydrated and dried over saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 18 g of the target product as a brown oil. 1H-NMR (300MHz); δ8.3-8.4(m, 2H), 7.9-7.95(m, 1H), 5.35-5.5(m, 1H), 4.24(q, J=7.2Hz, 2H), 4.13(q, J=7.2Hz, 2H), 3.36(brs, 2H), 2.89(d, J=5.7Hz, 2H), 1.31(t, J=7.2Hz, 3H), 1.20(t, J=7.2Hz, 3H).

[0207] Step 2: Synthesis of ethyl 5'-bromo-6'-chloro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3'-bipyridine]-5-carboxylate. To a mixed solution of 22 g of ethyl 3-(5-bromo-6-chloropyridin-3-yl)-3-(3-ethoxy-3-oxopropanamido)propanoate and 94 ml of dehydrated ethanol, 2.0 g of sodium hydride [manufactured by Yoneyama Pharmaceutical Co., Ltd., product name: sodium hydride, oily (approximately 63% by mass), purity: 57.5-67.5%, product code 03414] was added and stirred at 55°C for 5 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off under reduced pressure. 150 ml of dipropyl ether was added to the resulting residue, and the mixture was extracted with 150 ml of water. To the resulting aqueous layer, 35% by mass hydrochloric acid was added until the pH reached 2, and the mixture was extracted with a mixed solution of ethyl acetate:tetrahydrofuran = 9:1 (150 ml x 3 times). The resulting organic layer was dehydrated and dried over saturated brine and anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 16 g of the target product as a brown solid. Melting point: 124-126°C 1 H-NMR (400MHz); δ8.36(d, J=2.0Hz, 1H), 7.98(d, J=2.4Hz, 1H), 6.00(brs, 1H), 4.7-4.8(m, 1H), 4.35-4.5(m, 2H), 2.7-3.05(m, 2H), 1.40(t, J=7.2Hz, 3H).

[0208] Step 3: Preparation of ethyl 6'-chloro-6"-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3"-terpyridine]-5-carboxylate To a mixed solution of 5.6 g of ethyl 5'-bromo-6'-chloro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3'-bipyridine]-5-carboxylate, 40 ml of 1,4-dioxane, and 10 ml of water, 1.9 g of 2-fluoropyridine-5-boronic acid, 9.5 g of tripotassium phosphate, and 606 mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct were added, and the mixture was stirred at 55°C for 2 hours under a nitrogen atmosphere. After completion of the reaction, 200 ml of diisopropyl ether was added, and the mixture was extracted with a mixed solution of 10 g of potassium carbonate and 74 ml of water. To the resulting aqueous layer, 35% by mass hydrochloric acid was added until the pH reached 2, and the mixture was extracted with ethyl acetate (150 ml x 3 times). The resulting organic layer was dehydrated and dried over saturated brine and anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was washed with a mixed solution of ethanol:diisopropyl ether = 1:2, yielding 2.0 g of the target product as a light brown solid. Melting point: 178-180°C 1 H-NMR (400MHz); δ8.47(d, J=2.4Hz, 1H), 8.30(brs, 1H), 7.9-8.0(m, 1H), 7.71(d, J=2.0Hz, 1H), 7.05-7.1(m, 1H), 5.70(brs, 1H), 4.8-4.9(m, 2H), 4.35-4.5(m, 2H), 2.7-3.05(m, 2H), 1.40(t, J=7.2Hz, 3H).

[0209] The synthesis examples of the intermediates used in Synthesis Example 3 for the compounds of the present invention are described below.

[0210] Intermediate Synthesis Example 2: Synthesis of 6-(((2-fluoroisonicotinimidamido)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide Step 1: Synthesis of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate To a mixed solution of 18.3 g of di-tert-butyl 4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 60 ml of acetonitrile, 4.0 g of imidazole and 6.6 g of 1,1′-carbonyldiimidazole were added, and the mixture was stirred at 85° C. for 30 minutes. After cooling to room temperature, 6.6 g of 5-fluoropyridin-2-amine was added and stirred for 18 hours. 350 ml of diisopropyl ether was added, and the mixture was stirred at 0°C for 1.5 hours, and the precipitated solid was collected by filtration. The obtained solid was washed with a mixed solution of acetonitrile:diisopropyl ether = 1:5, to obtain 26.3 g of the target product as a pale red solid. Melting point: 152-154°C

[0211] Step 2: Synthesis of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid To a mixed solution of 15.4 g of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 70 ml of dichloromethane, 50 ml of trifluoroacetic acid was added and stirred at room temperature for 25 hours. 140 ml of toluene was added and the solvent was distilled off under reduced pressure. 100 ml of toluene was added and the solvent was distilled off under reduced pressure. 100 ml of toluene was added and the solvent was distilled off under reduced pressure. 100 ml of chloroform was added and the solid was collected by filtration. The obtained solid was washed with chloroform to obtain 14.6 g of the target product as a white solid. Melting point: 223-225°C

[0212] Step 3: Synthesis of 6-(((2-fluoroisonicotinimidamide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide To a mixed solution of 100 mg of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid, 55 mg of 2-fluoro-N-hydroxyisonicotinimidamide, and 4 ml of N,N-dimethylformamide, 72 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5 mg of 1-hydroxy-7-azabenzotriazole were added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 12 ml of water and 1 ml of 1 mol / l hydrochloric acid were added, and the precipitated solid was collected by filtration. The resulting solid was washed with water to obtain 80 mg of the target product as a white solid. Melting point: 146-148°C

[0213] The compounds of the present invention and their synthetic intermediates can be synthesized according to the above-mentioned synthetic methods and synthetic examples. Examples of aryltetrahydropyridine compounds synthesized in the same manner as in Synthetic Examples 1 to 3 are shown in Tables 7 to 12, but the aryltetrahydropyridine compounds of the present invention are not limited to these. Examples of synthetic intermediates synthesized in the same manner as in Intermediate Synthetic Examples 1 and 2 are shown in Tables 13 to 15, but the synthetic intermediates of the present invention are not limited to these.

[0214] In addition, in the table, Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12a, Q-12b, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31a, Q-45a and Q-52a each represent the following structures.

[0215]

[0216] In addition, in the table, G-1, G-2, G-3, G-4, G-5, G-6a, G-7, G-8a, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 and G-40 each represent the following structures.

[0217]

[0218] In addition, the descriptions D-1, D-2 and D-3 in the table respectively represent the following structures.

[0219] The numbers in the structural formulas above indicate the substituents (Z １ ) ｔ１ , (Z １ ) ｔ２ , (Z １ ) ｔ３ , (Z １ ) ｔ４ , (Z １ ) ｔ５ , (Z ２ ) ｔ２ , (Z ２ ) ｔ３ , (Z ２ ) ｔ４ , (Z ２ ) ｔ５ , (Z ５ ) ｔ３ , (Z ５ ) ｔ５ or (Z ５ ) ｔ８ For example, in the table, "Q-1(4-F)" represents "4-fluorophenyl", "G-2" represents "phenyl", and "G-1(2-OCH ３ , 4-OCH ３ ) stands for "2,6-dimethoxypyridin-3-yl".

[0220] In the table, "i-Bu" represents an isobutyl group, and "c-Pr" represents a cyclopropyl group.

[0221] Furthermore, "m.p." represents the melting point (unit: °C), and the notation "*1" indicates that the compound is an oily or resinous compound with no melting point. Furthermore, in the melting point descriptions in the tables, ">" indicates that the melting point of the compound is higher than the temperature indicated; for example, the notation ">300" means that the compound did not melt at 300°C.

[0222] [Table 7] ―――――――――――――――――――――――― No. R 1Q G m.p.(℃) ―――――――――――――――――――――――――― 1-001 CF3 Q-1(4-F) G-1(4-F) 200-202 1-002 CF3 Q-1(4-F) G-1(5-F) 188-190 1-003 CF3 Q-1(4-F) G-1(4-OCH3) 95-97 1-004 CF3 Q-1(4-F) G-2 96-98 1-005 CF3 Q-1(4-F) G-2(2-F) 177-179 1-006 CF3 Q-1(4-F) G-2(3-F) 157-159 1-007 CF3 Q-1(4-F) G-2(4-F) 176-178 1-008 CF3 Q-1(4-F) G-2(2-SCH3) 195-197 1-009 CF3 Q-1(4-F) G-2(4-SCH3) 121-123 1-010 CF3 Q-1(4-F) G-2(2-COCH3) 181-183 1-011 CF3 Q-1(4-F) G-2(3-COCH3) 159-161 1-012 CF3 Q-1(4-F) G-2(4-COCH3) 176-178 1-013 CF3 Q-1(4-F) G-1 232-234 1-014 CF3 Q-1(4-F) G-3 176-178 1-015 CF3 Q-1(4-F) G-4 174-176 1-016 CF3 Q-1(4-F) G-2(2-OCH3) 187-189 1-017 CF3 Q-1(4-F) G-2(3-OCH3) 137-139 1-018 CF3 Q-1(4-F) G-2(4-OCH3) 174-176 1-019 CF3 Q-1(4-F)G-2(4-SO2CH3) 204-206 1-020 CF3 Q-1(4-F) G-1(2-OCH3,4-OCH3) 177-179 1-021 CF3 Q-1(4-F) G-1(4-CF3) 199-200 1-022 CF3 Q-1(4-F) G-2(3-CN) 164-166 1-023 CF3 Q-1(4-F) G-2(4-CN) 209-211 1-024 CF3 Q-1(4-F) G-1(4-CN) 226-228 ――――――――――――――――――――――――――

[0223] [Table 8] ―――――――――――――――――――――――――――― No. R 1Q G m.p.(℃) ―――――――――――――――――――――――――――― 2-001 Cl Q-1(4-F) G-1(4-F) 210-212 2-002 H Q-1(4-F) G-2(2-CF3) 212-216 2-003 H Q-1(4-F) G-2(3-CF3) 175-177 2-004 H Q-1(4-F) G-2(4-CF3) 191-193 2-005 H Q-1(4-F) G-1(4-F) 236-238 2-006 H Q-1(4-F) G-1(4-OCHF2) 200-202 2-007 H Q-1(4-F) G-1(4-OCH2CH2CH3) 187-189 2-008 Cl Q-2(4-F) G-1(4-F) 131-133 2-009 Cl Q-3(4-F) G-1(4-F) 174-176 2-010 Cl Q-2(4-Cl) G-1(4-F) 169-171 2-011 Cl Q-4(4-Cl) G-1(4-F) 223-225 2-012 Cl Q-2(4-CF3) G-1(4-F) 197-199 2-013 Cl Q-2(4-CN) G-1(4-F) 105-107 2-014 Cl Q-1(4-F) G-1(4-OCH3) 172-174 2-015 Cl Q-1(4-SO2CH3) G-1(4-OCH3) 186-188 2-016 Cl Q-2(4-F) G-1(4-OCH3) 189-192 2-017 Cl Q-2(4-Cl) G-1(4-OCH3) 201-204 2-018 Cl Q-3(4-F)G-6a 139-141 2-019 Cl Q-3(4-F) G-1 176-178 2-020 Cl Q-3(4-F) G-3 174-176 2-021 Cl Q-3(4-F) G-4 131-134 2-022 Cl Q-3(4-F) G-1(2-OCH3) 129-131 2-023 Cl Q-2(4-F) G-1 144-147 2-024 Cl Q-2(4-F) G-5 164-166 2-025 Cl Q-2(4-F) G-1(2-OCH3) 138-140 2-026 Cl Q-7(4-CF3) G-1(4-F) 197-199 2-027 Cl Q-2(4-F) G-2(4-F) 186-188 2-028 Cl Q-2(4-F) G-1(5-F) 124-126 2-029 Cl Q-2(4-F) G-1(5-OCH3) 117-119 2-030 Cl Q-3(4-F) G-2(4-F) 162-164 2-031 Cl Q-3(4-F) G-3(3-OCH3) 169-171 2-032 Cl Q-3(4-F) G-2 122-124 2-033 Cl Q-2(4-F) G-1(6-OCH3) 164-166 2-034 Cl Q-3(4-F) G-1(2-F) 161-163 2-035 Cl Q-1(4-Cl) G-1(4-F) 199-201 2-036 Cl Q-1(4-Br) G-1(4-F) 202-204 2-037 ClQ-1(4-CF3) G-1(4-F) 202-204 2-038 Cl Q-1(4-SCF3) G-1(4-F) 196-198 2-039 Cl Q-1(4-SCH3) G-1(4-F) 174-176 2-040 Cl Q-1(3-F,4-F) G-1(4-F) 142-144 2-041 Cl Q-1(2-F,4-F) G-1(4-F) 167-169 2-042 Cl Q-1(4-F) G-1(4-Cl) 234-236 2-043 Cl Q-1(4-SOCH3) G-1(4-Cl) 237-239 2-044 Cl Q-3(4-CN) G-1(4-Cl) 199-201 2-045 Cl Q-4(4-Cl) G-1(4-Cl) 209-211 2-046 Cl Q-5(4-Cl) G-1(4-Cl) 206-208 2-047 Cl Q-3(4-Cl) G-3 194-196 2-048 Cl Q-2(4-Cl) G-1(5-F) 224-226 2-049 Cl Q-3(4-F) G-1(5-F) 192-194 2-050 Cl Q-4(4-Br) G-1(5-F) 240-242 2-051 Cl Q-6(4-CF3) G-1(5-F) 195-197 2-052 Cl Q-5(4-Cl) G-1(5-F) 201-203 2-053 Cl Q-2(4-Br) G-1(5-F) 224-226 2-054 Cl Q-2(4-CF3) G-1(5-F) 185-187 2-055 Cl Q-2(4-CN) G-1(5-F) 237-239 2-056Cl Q-3(4-CF3) G-1(5-F) 205-207 2-057 Cl Q-3(4-CN) G-1(5-F) 246-248 2-058 Cl Q-1(4-F) G-1(5-F) 231-233 2-059 Cl Q-4(4-CF3) G-1(5-F) 135-137 2-060 Cl Q-6(4-Cl) G-1(5-F) 220-222 2-061 Cl Q-6(4-Br) G-1(5-F) 217-219 2-062 Cl Q-1(4-CH3) G-1(4-F) 219-221 2-063 Cl Q-3(4-CH3) G-1(4-F) 171-173 2-064 Cl Q-3(4-Cl) G-2(4-CH2CH3) 174-176 2-065 Cl Q-3(4-Cl) G-2(4-CH=CH2) 149-151 2-066 Cl Q-3(4-Cl) G-2(4-COCH3) 187-189 2-067 Cl Q-3(4-Cl) G-2(3-CH3) 161-163 2-068 Cl Q-3(4-Cl) G-2(3-OCH3) 112-114 2-069 Cl Q-3(4-Cl) G-2(3-COCH3) 131-133 2-070 Cl Q-1(4-CN) G-2(4-F) 205-207 2-071 Cl Q-1(4-CN) G-1(5-F) 160-162 2-072 Cl Q-1(4-CN) G-1(4-OCH3) 177-179 2-073 Cl Q-7(4-CF3) G-2(4-F) 185-187 2-074 Cl Q-7(4-CF3) G-1(5-F)246-248 2-075 Cl Q-7(4-CF3) G-1(4-OCH3) 222-224 2-076 Cl Q-3(4-Cl) G-1(4-NO2) 204-206 2-077 Cl Q-3(4-Cl) G-2(4-OCH3) 122-124 2-078 Cl Q-3(4-Cl) G-2(4-SCH3) 122-124 2-079 Cl Q-3(4-Cl) G-2(4-CN) 139-141 2-080 Cl Q-3(4-Cl) G-2(3-F) 182-184 2-081 Cl Q-3(4-Cl) G-2(3-SCH3) 150-152 2-082 Cl Q-3(4-Cl) G-2 129-131 2-083 Cl Q-1(4-CN) G-1(4-F) 197-199 2-084 Cl Q-3(4-Cl) G-1(4-F) 205-207 2-085 Cl Q-4(4-Br) G-1(4-F) 215-217 2-086 Cl Q-3(4-F,6-F) G-1(4-F) 207-209 2-087 Cl Q-6(4-Cl) G-1(4-F) 190-192 2-088 Cl Q-3(4-CN) G-1(4-F) 195-197 2-089 Cl Q-1(4-F) G-2 222-224 2-090 Cl Q-1(4-CN) G-2 220-222 2-091 Cl Q-2(4-F) G-2 205-207 2-092 Cl Q-2(4-Cl) G-2 229-231 2-093 Cl Q-2(4-CN) G-2174-176 2-094 Cl Q-3(4-CN) G-2 171-173 2-095 Cl Q-4(4-Cl) G-2 217-219 2-096 Cl Q-3 G-1(4-F) 99-101 2-097 Cl Q-2(4-CN) G-1 222-224 2-098 Cl Q-4(4-Cl) G-1 186-188 2-099 Cl Q-4(4-Br) G-1 234-236 2-100 Cl Q-6(4-Cl) G-1 237-239 2-101 Cl Q-8 G-1(4-F) 121-123 2-102 Cl Q-2(4-OCH3) G-1(4-F) 136-138 2-103 Cl Q-3(4-F,6-Cl) G-1(4-F) 129-131 2-104 Cl Q-3(4-F,6-CH3) G-1(4-F) 159-161 2-105 Cl Q-2(2-F,4-CH3) G-1(4-F) 211-213 2-106 Cl Q-2(2-CH3,4-F) G-1(4-F) 110-112 2-107 Cl Q-3(4-F,5-CH3) G-1(4-F) 181-183 2-108 Cl Q-3(3-CH3,4-F) G-1(4-F) 208-210 2-109 Cl Q-2(2-F,4-F) G-1(4-F) 200-201 2-110 Cl Q-3(4-Cl,6-Cl) G-1(4-F) 138-140 2-111 Cl Q-3(4-Cl,6-F) G-1(4-F) 186-188 2-112 Cl Q-3(4-CH3,6-F) G-1(4-F) 151-1532-113 Cl Q-1(4-F) G-3(3-F) 228-230 2-114 Cl Q-2(4-F) G-3(3-F) 186-188 2-115 Cl Q-3(4-F) G-3(3-F) 208-210 2-116 Cl Q-2(2-CN,4-Cl) G-1(4-F) 209-211 2-117 Cl Q-2(4-Cl,6-OCH3) G-1(4-F) 201-203 2-118 Cl Q-2(2-OCH3,4-Cl) G-1(4-F) 129-131 2-119 Cl Q-2(4-CH3) G-1(4-F) 161-163 2-120 Cl Q-6(4-CH3) G-1(4-F) 97-99 2-121 Cl Q-1(4-OCF3) G-1(4-F) 214-216 2-122 Cl Q-3(4-CF3,6-F) G-1(4-F) 177-179 2-123 Cl Q-6(4-Br) G-1(4-F) 186-188 2-124 Cl Q-2(4-F,5-CH3) G-1(4-F) 181-183 2-125 Cl Q-2(4-F,6-CH3) G-1(4-F) 187-189 2-126 Cl Q-2(4-Cl,5-Cl) G-1(4-F) 169-171 2-127 Cl Q-3(4-Cl,6-CN) G-1(4-F) 182-184 2-128 Cl Q-2(2-Cl,4-Cl) G-1(4-F) 211-213 2-129 Cl Q-2(4-Cl,5-CH3) G-1(4-F) 156-158 2-130 Cl Q-3(4-Cl,6-CH3) G-1(4-F) 177-179 2-131 Cl Q-4(4-Cl,6-Cl) G-1(4-F) 186-188 2-132 ClQ-3(3-F,4-Br) G-1(4-F) 171-173 2-133 Cl Q-4 G-1(4-F) 146-148 2-134 Cl Q-6 G-1(4-F) 151-153 2-135 Cl Q-9 G-1(4-F) 199-201 2-136 Cl Q-3(5-F) G-1(4-F) 124-126 2-137 Cl Q-2(5-F) G-1(4-F) 226-228 2-138 Cl Q-3(4-Br,6-F) G-1(4-F) 159-161 2-139 Cl Q-2(4-Br,5-F) G-1(4-F) 219-221 2-140 Cl Q-3(4-Br,5-F) G-1(4-F) 218-220 2-141 Cl Q-3(3-F) G-1(4-F) 187-189 2-142 Cl Q-3(6-F) G-1(4-F) 181-183 2-143 Cl Q-4(4-CN) G-1(4-F) 169-171 2-144 Cl Q-3(4-Br) G-1(4-F) 206-208 2-145 Cl Q-3(4-CF3) G-1(4-F) 209-211 2-146 Cl Q-2(4-F) G-1(5-Cl) 122-124 2-147 Cl Q-4 G-1(5-Cl) 172-174 2-148 Cl Q-4 G-1(5-CH3) 191-193 2-149 Cl Q-4 G-1(4-CH3) 191-193 2-150 Cl Q-3(3-Cl) G-1(4-F) 187-189 2-151 Cl Q-3(3-CH3)G-1(4-F) 197-199 2-152 Cl Q-3(4-NO2) G-1(4-F) 202-204 2-153 Cl Q-3(5-CH3) G-1(4-F) 107-109 2-154 Cl Q-9(4-CH3) G-1(4-F) 207-209 2-155 Cl Q-2(4-Cl) G-3(3-F) 191-193 2-156 Cl Q-3(4-Cl) G-3(3-F) 180-182 2-157 Cl Q-3 G-3(3-F) 201-203 2-158 Cl Q-1(4-CN) G-3(3-F) 219-221 2-159 Cl Q-3(4-CN) G-3(3-F) 221-223 2-160 Cl Q-3(4-F,6-F) G-3(3-F) 199-201 2-161 Cl Q-4 G-3(3-F) 205-207 2-162 Cl Q-3(4-CH3) G-3(3-F) 192-194 2-163 Cl Q-3(4-Cl,6-F) G-3(3-F) 183-185 2-164 Cl Q-9 G-3(3-F) 212-214 2-165 Cl Q-6(4-Cl) G-3(3-F) 199-201 2-166 Cl Q-3(6-F) G-3(3-F) 202-204 2-167 CF3 Q-3(4-F) G-1(4-F) 178-180 2-168 CF3 Q-2(4-F) G-1(4-F) 174-176 2-169 CF3 Q-3(4-Cl) G-1(4-F) 191-193 2-170 CF3 Q-2(4-Cl) G-1(4-F)131-132 2-171 CF3 Q-3(4-CH3) G-1(4-F) 111-113 2-172 CF3 Q-12a G-1(4-F) 191-193 2-173 CF3 Q-9(4-CH3) G-1(4-F) 199-201 2-174 CF3 Q-9(4-Cl) G-1(4-F) 159-161 2-175 CF3 Q-4(4-Cl) G-1(4-F) 204-206 2-176 CF3 Q-4 G-1(4-F) 194-196 2-177 CF3 Q-3(4-Br) G-1(4-F) 186-188 2-178 CF3 Q-1(4-F) G-1(4-F) 201-203 2-179 CF3 Q-3(4-CF3) G-1(4-F) 204-206 2-180 CF3 Q-6(4-Cl) G-1(4-F) 182-184 2-181 CF3 Q-3(4-Cl,6-F) G-1(4-F) 181-183 2-182 CF3 Q-3(4-F,6-F) G-1(4-F) 199-201 2-183 CF3 Q-1(4-CN) G-1(4-F) 172-174 2-184 CF3 Q-9 G-1(4-F) 199-201 2-185 CF3 Q-13(4-CH3) G-1(4-F) 191-193 2-186 Cl Q-3(4-F) G-3(3-Cl) 162-164 2-187 Cl Q-3(4-Cl) G-3(3-Cl) 124-126 2-188 Cl Q-4(4-Cl) G-3(3-Cl) 131-133 2-189 Cl Q-2(4-Cl) G-3(3-Cl) 171-1732-190 Cl Q-3 G-3(3-Cl) 142-144 2-191 CF3 Q-3(4-F) G-3(3-F) 169-171 2-192 CF3 Q-2(4-F) G-3(3-F) 149-151 2-193 CF3 Q-3(4-Cl) G-3(3-F) 112-114 2-194 CF3 Q-2(4-Cl) G-3(3-F) 136-138 2-195 CF3 Q-3(4-CH3) G-3(3-F) 116-118 2-196 CF3 Q-12a G-3(3-F) 101-103 2-197 CF3 Q-9(4-CH3) G-3(3-F) 111-113 2-198 CF3 Q-4(4-Cl) G-3(3-F) 154-156 2-199 CF3 Q-3 G-3(3-F) 151-153 2-200 CF3 Q-3 G-1(4-F) 136-138 2-201 CF3 Q-4 G-3(3-F) 157-159 2-202 CF3 Q-3(4-Br) G-3(3-F) 174-176 2-203 CF3 Q-1(4-F) G-3(3-F) 172-174 2-204 CF3 Q-3(4-CF3) G-3(3-F) 116-118 2-205 CF3 Q-6(4-Cl) G-3(3-F) 141-143 2-206 CF3 Q-3(4-Cl,6-F) G-3(3-F) 154-156 2-207 CF3 Q-3(4-F,6-F) G-3(3-F) 159-161 2-208 CF3 Q-1(4-CN) G-3(3-F) 144-146 2-209 CF3Q-9 G-3(3-F) 114-116 2-210 CF3 Q-13(4-CH3) G-3(3-F) 168-170 2-211 CF3 Q-3(3-F) G-3(3-F) 149-151 2-212 CF3 Q-3(6-F) G-3(3-F) 99-101 2-213 CF3 Q-3(4-CN) G-3(3-F) 112-114 2-214 CF3 Q-2(4-CN) G-3(3-F) 122-124 2-215 CF3 Q-2(4-CF3) G-3(3-F) 112-114 2-216 CF3 Q-4(4-Br) G-3(3-F) 177-179 2-217 CF3 Q-6(4-Br) G-3(3-F) 144-146 2-218 CF3 Q-1(4-CH3) G-3(3-F) 187-189 2-219 CF3 Q-3(3-Cl) G-3(3-F) 164-166 2-220 Cl Q-3(4-Cl) G-2(4-F) 146-148 2-221 Cl Q-2(4-Cl) G-2(4-F) 199-201 2-222 Cl Q-3(4-CH3) G-2(4-F) 162-164 2-223 Cl Q-12a G-2(4-F) 107-109 2-224 Cl Q-9(4-CH3) G-2(4-F) 156-158 2-225 Cl Q-4(4-Cl) G-2(4-F) 156-158 2-226 Cl Q-3 G-2(4-F) 141-143 2-227 Cl Q-4 G-2(4-F) 132-134 2-228 Cl Q-3(4-CN)G-2(4-F) 122-124 2-229 Cl Q-1(4-F) G-2(4-F) 187-189 2-230 Cl Q-3(4-CF3) G-2(4-F) 164-166 2-231 Cl Q-6(4-Cl) G-2(4-F) 171-173 2-232 Cl Q-3(4-Cl,6-F) G-2(4-F) 174-176 2-233 Cl Q-2(4-CN) G-2(4-F) 200-202 2-234 Cl Q-2(4-CF3) G-2(4-F) 181-183 2-235 Cl Q-9 G-2(4-F) 154-156 2-236 Cl Q-13(4-CH3) G-2(4-F) 184-186 2-237 Cl Q-11 G-2(4-F) 161-163 2-238 Cl Q-6 G-2(4-F) 127-129 2-239 Cl Q-13 G-2(4-F) 146-148 2-240 Cl Q-10(3-CH3) G-2(4-F) 172-174 2-241 Cl Q-1(4-OH) G-2(4-F) 129-131 2-242 Cl Q-1(4-CH=CH2) G-2(4-F) 182-184 2-243 Cl Q-1(4-C≡CH) G-2(4-F) 164-166 2-244 CF3 Q-3(4-F) G-2(4-F) 111-113 2-245 CF3 Q-3(4-F) G-2(4-OCH3) 167-169 2-246 CF3 Q-3(4-F) G-2(3-F) 159-161 2-247 CF3 Q-3(4-F)G-2(3-OCH3) 144-146 2-248 CF3 Q-3(4-F) G-2(2-CH3) 176-178 2-249 CF3 Q-3(4-F) G-2(2-F) 216-218 2-250 CF3 Q-3(4-F) G-2(2-OCH3) 174-176 2-251 CF3 Q-3(4-F) G-1 136-138 2-252 Cl Q-3(4-F) G-2(3-CH3) 176-178 2-253 Cl Q-2(4-F) G-2(3-CH3) 179-181 2-254 Cl Q-2(4-Cl) G-2(3-CH3) 201-203 2-255 Cl Q-3(4-CH3) G-2(3-CH3) 179-181 2-256 Cl Q-12a G-2(3-CH3) 171-173 2-257 Cl Q-9(4-CH3) G-2(3-CH3) 207-209 2-258 Cl Q-1(4-OCH3) G-2(3-CH3) 202-204 2-259 Cl Q-4(4-Cl) G-2(3-CH3) 196-198 2-260 Cl Q-3 G-2(3-CH3) 111-113 2-261 Cl Q-4 G-2(3-CH3) 181-183 2-262 Cl Q-3(4-CN) G-2(3-CH3) 179-181 2-263 Cl Q-1(4-F) G-2(3-CH3) 202-204 2-264 Cl Q-6(4-Cl) G-2(3-CH3) 174-176 2-265 Cl Q-3(4-Cl,6-F) G-2(3-CH3) 181-1832-266 Cl Q-2(4-CN) G-2(3-CH3) 189-191 2-267 Cl Q-2(4-CF3) G-2(3-CH3) 204-206 2-268 Cl Q-9 G-2(3-CH3) 197-199 2-269 Cl Q-1(4-CN) G-2(3-CH3) 172-174 2-270 Cl Q-11 G-2(3-CH3) 152-154 2-271 Cl Q-6 G-2(3-CH3) 126-128 2-272 Cl Q-3(3-CH3) G-2(3-CH3) 179-181 2-273 Cl Q-3(5-CH3) G-2(3-CH3) 182-184 2-274 Cl Q-2(2-Cl) G-2(3-CH3) 187-189 2-275 Cl Q-2(2-F) G-2(3-CH3) 164-166 2-276 Cl Q-3(3-Cl) G-2(3-CH3) 191-193 2-277 Cl Q-3(3-F) G-2(3-CH3) 186-188 2-278 Cl Q-3(4-NO2) G-2(3-CH3) 187-189 2-279 Cl Q-1(4-NO2) G-2(3-CH3) 172-174 2-280 Cl Q-1(4-C≡CH) G-2(3-CH3) 169-171 2-281 Cl Q-6(3-Cl) G-2(3-CH3) 147-149 2-282 Cl Q-1(4-CH3) G-2(3-CH3) 186-188 2-283 Cl Q-8(3-Cl) G-2(3-CH3) 137-139 2-284 Cl Q-1(3-SCH3)G-2(3-CH3) 191-193 2-285 Cl Q-1(3-SO2CH3) G-2(3-CH3) 156-158 2-286 Cl Q-22 G-1(4-F) *1 2-287 Cl Q-2 G-1(4-F) *1 2-288 Cl Q-14 G-1(4-F) *1 2-289 Cl Q-5 G-1(4-F) *1 2-290 Cl Q-31a G-2(4-F) 139-140 2-291 Cl Q-52a G-2(4-F) 152-154 2-292 Cl Q-1(4-C(O)OCH3) G-2(4-F) 194-196 2-293 Cl Q-1(4-C(O)OH) G-2(4-F) 231-233 2-294 Cl Q-1(4-C(O)N(H)CH3) G-2(4-F) 212-214 2-295 Cl Q-1(4-C(O)CH3) G-2(4-F) 211-213 2-296 Cl Q-1(4-C(O)OC(CH3)3) G-2(4-F) 156-158 2-297 CF3 Q-3(4-F) G-3(3-CF3) 129-131 2-298 CF3 Q-3(4-F) G-3(3-CH3) 206-208 2-299 Cl Q-3(4-CF3) G-3(3-F) 182-184 2-300 Cl Q-4(4-Cl) G-3(3-F) 172-174 2-301 Cl Q-2(4-CN) G-3(3-F) 216-218 2-302 Cl Q-3(3-CH3) G-3(3-F)207 - 209 2 - 303 Cl Q - 3(4 - Br) G - 3(3 - F) 191 - 193 2 - 304 Cl Q - 4(4 - Br) G - 3(3 - F) 154 - 156 2 - 305 Cl Q - 3(3 - F) G - 3(3 - F) 209 - 211 ――――――――――――――――――――――――――――

[0224] [Table 9] ―――――――――――――――――――――――――――― No. Q G m.p.(℃) ―――――――――――――――――――――――――――― 3-001 Q-1(4-F) G-2 200-202 3-002 Q-1(4-F) G-2(2-CF3) 177-179 3-003 Q-1(4-F) G-2(4-Cl) 228-230 3-004 Q-1(4-F) G-2(4-CF3) 217-219 3-005 Q-1(4-F) G-2(3-CF3) 181-183 3-006 Q-1(4-F) G-7 206-208 3-007 Q-1(4-F) G-1 207-209 3-008 Q-1(4-F) G-2(4-SO2CH3) 226-228 3-009 Q-1(4-F) G-7(4-F) 201-203 3-010 Q-1(4-F) G-2(4-F) 228-230 3-011 Q-1(4-F) G-2(3-F) 221-223 3-012 Q-1(4-F) G-2(2-F) 207-209 3-013 Q-1(4-F) G-6a(2-Cl) 238-240 3-014 Q-1(4-F) G-8a 230-232 3-015 Q-1(4-F) G-1(4-Cl) 230-232 3-016 Q-1(4-F) G-1(4-F) 216-218 3-017 Q-2(4-Cl) G-2 230-232 3-018Q-2(4-Cl) G-2(3-F) 225-227 3-019 Q-2(4-Cl) G-2(2-F) 229-231 3-020 Q-1(4-F) G-7(3-F) 222-224 3-021 Q-1(4-F) G-1(5-F) 208-210 3-022 Q-1(4-F) G-3(3-F) 216-218 3-023 Q-1(4-F) G-7(6-F) 215-217 3-024 Q-1(4-F) G-9(5-Br) 210-212 3-025 Q-1(4-F) G-7(5-F) 193-195 3-026 Q-1(4-F) G-2(2-F,5-F) 241-243 3-027 Q-1(4-F) G-2(3-F,4-F) 212-214 3-028 Q-1(4-F) G-2(3-Br) 199-201 3-029 Q-1(4-F) G-2(3-Cl) 208-210 3-030 Q-1(4-F) G-2(3-CH3) 191-193 3-031 Q-1(4-F) G-3 239-241 3-032 Q-2(4-F) G-1(4-F) 228-230 3-033 Q-1(4-F) G-2(2-F,3-F) 242-244 3-034 Q-1(4-F) G-2(3-F,5-F) 219-221 3-035 Q-3(4-F) G-1(4-F) 214-216 3-036 Q-3(4-F) G-3(3-F) 159-161 3-037 Q-2(4-F)G-3(3-F) 216-218 3-038 Q-2(4-F) G-3 229-231 3-039 Q-3(4-F) G-7(3-F) 187-189 3-040 Q-3(4-F) G-7(6-F) 189-191 3-041 Q-3(4-F) G-7(5-F) 206-208 3-042 Q-3(4-F) G-7(4-F) 169-171 3-043 Q-3(4-F) G-6a(2-Cl) 181-183 3-044 Q-3(4-F) G-3 197-199 3-045 Q-3(4-F) G-7 207-209 3-046 Q-2(4-F) G-7(3-F) 191-193 3-047 Q-2(4-F) G-7(6-F) 197-199 3-048 Q-2(4-F) G-6a(2-Cl) 222-224 3-049 Q-3(4-F) G-2(2-F,3-F) 192-194 3-050 Q-3(4-F) G-2(2-F,5-F) 207-209 3-051 Q-3(4-F) G-2(3-Br) 197-199 3-052 Q-3(4-F) G-2(3-Cl) 199-201 3-053 Q-3(4-F) G-2(3-CH3) 194-196 3-054 Q-3(4-F) G-1(4-Cl) 241-243 3-055 Q-3(4-F) G-2 187-189 3-056 Q-3(4-F) G-2(4-F)177-179 3-057 Q-3(4-F) G-2(3-F) 191-193 3-058 Q-3(4-F) G-2(2-F) 196-198 3-059 Q-3(4-F) G-2(3-F,5-F) 186-187 3-060 Q-2(4-Cl) G-3(3-F) 217-221 3-061 Q-3(4-F) G-3(3-CH3) 101-103 3-062 Q-3(4-F) G-2(3-F,4-F) 194-196 3-063 Q-3(4-F) G-2(2-F,4-F) 192-194 3-064 Q-3(4-F) G-3(2-F) 204-206 3-065 Q-3 G-3(3-F) 194-196 3-066 Q-4(4-Br) G-3(3-F) 199-201 3-067 Q-6(4-Cl) G-3(3-F) 199-201 3-068 Q-3(4-Br) G-3(3-F) 221-223 3-069 Q-3(4-Cl) G-3(3-F) 209-211 3-070 Q-2(4-CN) G-3(3-F) 231-233 3-071 Q-1(4-CN) G-3(3-F) 203-205 3-072 Q-3(4-CN) G-3(3-F) 97-99 3-073 Q-3(4-F,6-F) G-3(3-F) 97-99 3-074 Q-1(4-Cl) G-3(3-F) 209-211 3-075 Q-4 G-3(3-F) 167-1693-076 Q-4(4-Cl) G-3(3-F) 187-189 3-077 Q-3(4-Cl,6-F) G-3(3-F) 131-133 3-078 Q-3(4-CF3) G-3(3-F) 129-131 3-079 Q-2(4-Cl) G-1(4-F) 224-226 3-080 Q-2(4-Cl) G-2(4-F) 241-243 3-081 Q-2(4-F) G-7(4-F) 198-200 3-082 Q-2(4-F) G-2(4-F) 224-226 3-083 Q-3(4-F) G-1(5-F) 189-191 3-084 Q-3(4-F) G-2(3-CF3) 184-186 3-085 Q-3(4-F) G-8a 207-209 3-086 Q-3(4-F) G-9(5-Br) 144-146 3-087 Q-3(4-F) G-1(4-CH3) 232-234 3-088 Q-3(4-F) G-10 185-187 3-089 Q-1(4-F) G-3(3-CH3) 207-209 3-090 Q-1(4-F) G-3(3-Cl) 196-198 3-091 Q-3(4-F) G-11 217-219 3-092 Q-3(4-F) G-12 209-211 3-093 Q-3(4-F) G-13 212-214 3-094 Q-3(4-F) G-13(3-CH3) 211-212 3-095Q-3(4-F) G-14 207-209 3-096 Q-3(4-F) G-15 199-201 3-097 Q-3(4-F) G-16 211-212 3-098 Q-3(4-F) G-3(3-Cl) 174-177 3-099 Q-3(4-F) G-3(3-OH) 201-203 3-100 Q-3(4-F) G-3(3-OCH3) 144-146 3-101 Q-3(4-F) G-1(4-OH) 214-216 3-102 Q-3(4-Cl) G-1(4-F) 182-184 3-103 Q-3 G-1(4-F) 184-186 3-104 Q-3(4-CH3) G-1(4-F) 185-187 3-105 Q-9(4-CH3) G-1(4-F) 208-210 3-106 Q-1(2-F,4-Cl) G-3(3-F) 182-184 3-107 Q-1(3-F,4-F) G-3(3-F) 174-176 3-108 Q-1(3-F,5-F) G-3(3-F) 212-214 3-109 Q-1(4-F) G-9 222-224 3-110 Q-3(4-F) G-9 218-220 3-111 Q-1(4-F) G-17 226-228 3-112 Q-3(4-F) G-17 219-221 3-113 Q-3(4-F) G-6a(2-Cl,5-CH3) 159-161 3-114 Q-3(4-F)G-6a(2-Cl,5-Cl) 171-173 3-115 Q-1(4-F) G-6a(2-Cl,5-Cl) 199-201 3-116 Q-2(4-OCH3) G-3(3-F) 202-204 3-117 Q-1(4-F) G-2(4-N(CH3)2) 222-225 3-118 Q-3(4-F) G-2(4-N(CH3)2) 219-220 3-119 Q-3(4-F) G-7(3-CH3) 208-210 3-120 Q-1(3-Cl,4-NO2) G-3(3-F) 279-281 3-121 Q-20(3-CH3) G-3(3-F) 298-300 3-122 Q-12a G-3(3-F) 201-203 3-123 Q-45a G-3(3-F) 209-211 3-124 Q-3(4-F) G-2(3-C(=NOCH3)H) 184-186 3-125 Q-3(4-F) G-2(3-C(=NOCH3)CH3) 211-213 3-126 Q-2 G-3(3-F) 191-193 3-127 Q-3(4-CH3) G-2(4-F) 182-184 3-128 Q-3(4-CH3) G-2(3-F) 167-169 3-129 Q-3(4-CH3) G-2(2-F) 157-159 3-130 Q-3(4-F) G-1(5-CH3) 229-231 3-131 Q-1(4-F) G-2(2-F,4-F) 213-215 3-132 Q-3 G-2(2-F,4-F)196-198 3-133 Q-3(4-F) G-3(3-CF3) 209-211 3-134 Q-3(4-F) G-19 196-198 3-135 Q-3(4-F) G-6a(5-Cl) 186-188 3-136 Q-4(4-Cl) G-6a(2-Cl,5-CH3) 179-181 3-137 Q-3(4-F) G-2(4-OCH3) 199-201 3-138 Q-3(4-F) G-2(3-F,4-F,5-F) 214-216 3-139 Q-3(4-F) G-2(2-F,4-F,5-F) 222-224 3-140 Q-3(4-F) G-2(2-Cl,4-F) 162-164 3-141 Q-3(4-F) G-2(3-Cl,4-F) 197-199 3-142 Q-3(4-F) G-2(2-F,4-Cl) 201-203 3-143 Q-3(4-F) G-2(2-F,6-Cl) 189-191 3-144 Q-3(4-F) G-2(2-F,4-F,6-F) 181-183 3-145 Q-3(4-F) G-2(3-F,4-Cl) 194-196 3-146 Q-3(4-F) G-2(3-Br,4-F) 199-201 3-147 Q-3(4-F) G-7(4-Cl,6-Cl) 192-194 3-148 Q-3(4-F) G-7(4-CF3,6-Cl) 177-179 3-149 Q-3(4-F) G-1(4-CF3) 197-199 3-150 Q-3(4-CH3) G-3 >300 3-151Q-3(4-CH3) G-1 238-240 3-152 Q-3(4-CH3) G-7 203-205 3-153 Q-3(4-F) G-7(5-CH3) 194-196 3-154 Q-12a G-2(2-F,4-F) 92-94 3-155 Q-3(4-Cl) G-2(2-F,4-F) 206-208 3-156 Q-2(4-F) G-2(2-F,4-F) 216-218 3-157 Q-1(2-F,4-F) G-2(2-F,4-F) 221-223 3-158 Q-3 G-6a(2-Cl) 196-198 3-159 Q-3(4-F) G-6a(2-Cl,5-CF3) 79-81 3-160 Q-3(4-F) G-6a(5-CF3) 79-81 3-161 Q-1(3-F,4-F) G-2(2-F,4-F) 229-231 3-162 Q-1(4-CN) G-3(3-CH3) 194-196 3-163 Q-3(5-CH3) G-3(3-F) 181-183 3-164 Q-3(4-F) G-3(3-Br) 181-183 3-165 Q-3(4-CH3) G-3(3-F) *1 3-166 Q-1(2-F,6-F) G-3(3-F) *1 3-167 Q-3(4-CH3) G-17 233-235 3-168 Q-3(4-CH3) G-9 191-193 3-169 Q-3(4-CH3)G-3(3-Cl) 187-189 3-170 Q-3 G-6a(2-Cl,5-Cl) 167-169 3-171 Q-9 G-6a(2-Cl,5-Cl) 202-204 3-172 Q-3(4-Cl,6-F) G-3(3-CH3) 174-176 3-173 Q-4(4-Cl) G-3(3-CH3) 206-208 3-174 Q-3(3-CH3) G-2(2-F,4-F) 192-194 3-175 Q-3(5-CH3) G-2(2-F,4-F) 174-176 3-176 Q-3(4-CH3) G-3(3-CH3) 117-119 3-177 Q-2 G-2(2-F,4-F) 189-191 3-178 Q-3(4-CH3) G-2(2-F,4-F) 209-211 3-179 Q-3(4-OCH3) G-3(3-F) 201-203 3-180 Q-3(4-Cl) G-2(3-F) 196-198 3-181 Q-3(4-Cl) G-3 221-223 3-182 Q-3(4-Cl) G-7 197-199 3-183 Q-3(4-Cl) G-3(3-Cl) 169-171 3-184 Q-3 G-2(4-F) 192-194 3-185 Q-3 G-2(3-F) 152-154 3-186 Q-3 G-2(2-F) 162-164 3-187 Q-3G-3(3-Cl) 177-179 3-188 Q-3(4-F) G-2(3-NO2) 174-176 3-189 Q-3(4-F) G-2(4-CN) 224-226 3-190 Q-3(4-F) G-2(3-OCH3) 171-173 3-191 Q-3(4-F) G-2(3-OCF3) 164-166 3-192 Q-3(4-F) G-2(3-CN) 211-213 3-193 Q-3(4-F) G-2(3-C(O)OCH2CH3) 184-186 3-194 Q-3(3-F) G-3(3-F) 218-220 3-195 Q-3(3-F) G-3(3-CH3) 197-199 3-196 Q-3(3-F) G-2(2-F,4-F) 207-209 3-197 Q-3(3-F) G-3(3-Cl) 201-203 3-198 Q-9 G-3(3-CH3) 226-228 3-199 Q-3(5-F) G-2(2-F,4-F) 182-184 3-200 Q-12b G-3(3-F) 151-153 3-201 Q-12a(4-CH3) G-3(3-F) 214-216 3-202 Q-12a G-2(4-F) 189-191 3-203 Q-12a G-2(3-F) 174-176 3-204 Q-12a G-1(4-F) 169-171 3-205Q-12a G-3(3-Cl) 186-188 3-206 Q-12a G-3(3-CH3) 164-166 3-207 Q-12a G-2(3-F,4-F) 181-183 3-208 Q-12a G-6a(2-Cl,5-Cl) *1 3-209 Q-1(4-CN) G-3(3-Cl) 182-184 3-210 Q-1(4-CN) G-1(4-F) 235-236 3-211 Q-2(4-Cl) G-3 222-224 3-212 Q-3(4-F) G-20 218-220 3-213 Q-2(4-F) G-3(3-CF3) 189-191 3-214 Q-2(4-Cl) G-3(3-CF3) 179-181 3-215 Q-12a G-3(3-CF3) 211-213 3-216 Q-2(4-F) G-3(3-Cl) 172-174 3-217 Q-2(4-F) G-3(3-CH3) 211-213 3-218 Q-3(4-F) G-16(3-Cl) 239-241 3-219 Q-3(3-CH3) G-3(3-Cl) 201-203 3-220 Q-3(3-CH3) G-3(3-CH3) 192-194 3-221 Q-3(3-CH3) G-1(4-F) 202-204 3-222 Q-3(3-CF3) G-3(3-F) 177-179 3-223Q-3 G-3(3-CF3) 199-201 3-224 Q-1(4-F) G-3(3-CF3) 184-186 3-225 Q-4(4-Cl) G-3(3-CF3) 190-192 3-226 Q-9 G-3(3-CF3) 202-204 3-227 Q-3(4-F) G-28 211-213 3-228 Q-2(4-Cl) G-3(3-Cl) 187-189 3-229 Q-3(4-Br) G-3 236-238 3-230 Q-3(4-Br) G-1 241-243 3-231 Q-3(4-Br) G-7 217-219 3-232 Q-3(4-Br) G-3(3-Cl) 191-193 3-233 Q-3(3-Br) G-1(4-F) 184-186 3-234 Q-3(4-F) G-9(4-Cl) 209-211 3-235 Q-3(4-F) G-9(2-Cl) 202-204 3-236 Q-3(5-F) G-3(3-Cl) 199-201 3-237 Q-3(3-F) G-1(4-F) 191-193 3-238 Q-3(6-F) G-3(3-F) 162-164 3-239 Q-3(6-F) G-3(3-Cl) 176-178 3-240 Q-3(6-F) G-3(3-CH3) 181-183 3-241 Q-3(6-F)G-1(4-F) 196-198 3-242 Q-12a(4-Br) G-3(3-F) 229-231 3-243 Q-12a(4-CF3) G-3(3-F) 206-208 3-244 Q-3(4-F) G-15(4-CF3) 215-217 3-245 Q-9 G-3(3-Cl) 246-248 3-246 Q-9 G-3(3-F) 255-257 3-247 Q-9 G-1(4-F) 220-221 3-248 Q-1(2-F,3-Cl) G-3(3-F) 241-243 3-249 Q-3(3-OCH3) G-3(3-F) 187-189 3-250 Q-3(3-C(O)OCH3) G-3(3-F) 201-203 3-251 Q-12a(4-Br) G-3(3-CH3) 212-214 3-252 Q-12a(4-Br) G-1(4-F) 219-221 3-253 Q-3(4-F) G-40 177-179 3-254 Q-3(4-F) G-28(4-Cl,5-Cl) 184-186 3-255 Q-3(4-F) G-11(3-Cl) 184-186 3-256 Q-3(4-F) G-11(6-Cl) 191-193 3-257 Q-4 G-1(4-F) 162-164 3-258 Q-4 G-3(3-Cl) 197-199 3-259 Q-4G-3(3-CH3) 226-228 3-260 Q-4 G-3(3-CF3) 204-206 3-261 Q-4 G-7(4-F) 201-203 3-262 Q-4 G-28(4-Cl,5-Cl) 194-195 3-263 Q-3 G-28(4-Cl,5-Cl) 211-213 3-264 Q-3(4-F) G-16(3-CF3) 206-208 3-265 Q-3(4-F) G-27 203-206 3-266 Q-1(2-CH3,4-CH3) G-3(3-F) 217-219 3-267 Q-1(3-Cl,4-CH3) G-3(3-F) 203-205 3-268 Q-4(4-Cl) G-3(3-Cl) 148-150 3-269 Q-4(4-Cl) G-1(4-F) 187-189 3-270 Q-3(4-Cl,6-F) G-3(3-Cl) 143-145 3-271 Q-3(4-Cl,6-F) G-1(4-F) 170-172 3-272 Q-1(3-F,4-F) G-3(3-Cl) 189-191 3-273 Q-1(3-F,4-F) G-3(3-CH3) 110-112 3-274 Q-1(3-F,4-F) G-1(4-F) 122-124 3-275 Q-12a(4-CF3) G-3(3-CH3) 119-121 3-276 Q-12a(4-CF3) G-1(4-F) 164-166 3-277Q-3(4-F) G-3(3-SCH3) 201-203 3-278 Q-3(4-F) G-3(3-S(O)CH3) 179-181 3-279 Q-3(4-F) G-3(3-S(O)2CH3) 209-211 3-280 Q-4(4-CH3) G-3(3-F) 149-151 3-281 Q-3(3-F) G-3(3-CF3) 130-132 3-282 Q-3(5-F) G-3(3-CF3) 136-139 3-283 Q-3(3-CH3) G-3(3-CF3) 164-166 3-284 Q-3(4-CH3) G-3(3-CF3) 151-153 3-285 Q-3(6-F) G-3(3-CF3) 61-63 3-286 Q-3 G-3(3-CH3) 161-163 3-287 Q-9(3-CH3) G-3(3-F) 144-146 3-288 Q-9(3-CH3) G-3(3-Cl) 140-142 3-289 Q-9(3-CH3) G-3(3-CH3) 156-158 3-290 Q-9(3-CH3) G-1(4-F) 158-160 3-291 Q-29(3-CH2CH3) G-3(3-F) 136-138 3-292 Q-3(4-Cl,6-F) G-3(3-CF3) 88-91 3-293 Q-3(4-F) G-18 198-200 3-294 Q-10(3-CH3)G-3(3-F) 204-206 ―――――――――――――――――――――――――――――――

[0225] [Table 10] ―――――――――――――――――――――――――――――― No. R 1 Q GR 2 mp(℃) ――――――――――――――――――――――――――――――――― 4-001 Cl Q-3(4-F) G-1(4-F) C(O)OCH2CH3 117-119 ――――――――――――――――――――――――――――――

[0226] [Table 11] ――――――――――――――――――――――――――――― No. Q GR 2m.p.(℃) ―――――――――――――――――――――――――――― 5-001 Q-3(4-F) G-3(3-F) C(O)OCH2CH3 *1 5-002 Q-3(4-F) G-3(3-F) C(O)i-Bu *1 5-003 Q-3(4-F) G-3(3-F) C(O)c-Pr 121-123 5-004 Q-3(4-F) G-3(3-F) C(O)CH2OCH3 *1 5-005 Q-3(4-F) G-3(3-F) C(O)OCH3 *1 5-006 Q-3(4-F) G-3(3-F) C(O)C(O)CH2CH3 137-139 5-007 Q-3(4-F) G-3(3-F) C(O)OCH2CH=CH2 148-150 5-008 Q-3(4-F) G-3(3-F) C(O)CH3 190-192 5-009 Q-3(4-F) G-3(3-F) C(O)CH2CF3 204-206 5-010 Q-2(4-F) G-3(3-F) C(O)OCH3 83-85 5-011 Q-2(4-F) G-3(3-F) C(O)CH2OCH3 86-88 5-012 Q-2(4-F) G-3(3-F) C(O)CH3 *1 5-013 Q-3(4-F) G-3(3-F) D-1(2-CH3) 188-191 5-014 Q-3(4-F) G-3(3-F) D-2 *1 5-015 Q-3(4-F) G-3(3-F) D-3 *1 5-016 Q-2(4-F) G-3(3-F) D-3 113-115 ――――――――――――――――――――――――――――

[0227] [Table 12] ―――――――――――――――――――――――――――― No. Q G m.p.(℃) ―――――――――――――――――――――――――――― 6-001 Q-2(4-Cl) G-3(3-F) 196-198 6-002 Q-3(4-F) G-3(3-F) 200-202 6-003 Q-3(4-F) G-2(4-F) 181-182 6-004 Q-3(4-F) G-2(2-F,4-F) 169-172 6-005 Q-3(4-F) G-3(3-CH3) 191-192 ――――――――――――――――――――――――――――

[0228] [Table 13] ――――――――――――――― No. Q m.p.(℃) ――――――――――――――― i1-001 Q-1 i1-002 Q-1(4-F) 151-153 i1-003 Q-1(4-Cl) i1-004 Q-1(4-Br) i1-005 Q-1(4-I) i1-006 Q-1(4-CN) 161-163 i1-007 Q-1(4-CH3) i1-008 Q-1(4-CF3) i1-009 Q-2 i1-010 Q-2(4-F) 144-146 i1-011 Q-2(4-Cl) 172-174 i1-012 Q-2(4-Br) i1-013 Q-2(4-I) i1-014 Q-2(4-CN) i1-015 Q-2(4-CH3) i1-016 Q-2(4-CF3) i1-017 Q-3 154-156 i1-018 Q-3(4-F) 152-154 i1-019 Q-3(4-Cl) 182-184 i1-020 Q-3(4-Br) 186-188 i1-021 Q-3(4-I) i1-022 Q-3(4-CN) i1-023 Q-3(4-CH3) 167-169 i1-024 Q-3(4-CF3) i1-025 Q-4 146-148 i1-026 Q-4(4-F) i1-027 Q-4(4-Cl) 174-176 i1-028 Q-4(4-Br) 164-166 i1-029 Q-4(4-I) i1-030 Q-4(4-CN) i1-031 Q-4(4-CH3) i1-032 Q-4(4-CF3) i1-033 Q-6 i1-034 Q-6(4-F) i1-035 Q-6(4-Cl) 154-156 i1-036 Q-6(4-Br) i1-037 Q-6(4-I) i1-038 Q-6(4-CN)i1-039 Q-6(4-CH3) i1-040 Q-6(4-CF3) i1-041 Q-9 182-184 i1-042 Q-9(4-F) i1-043 Q-9(4-Cl) 186-188 i1-044 Q-9(4-Br) 166-168 i1-045 Q-9(4-I) i1-046 Q-9(4-CN) i1-047 Q-9(4-CH3) i1-048 Q-9(4-CF3) ―――――――――――――――

[0229] [Table 14] ――――――――――――――― No. Q m.p.(℃) ――――――――――――――― i2-002 Q-1(4-F) 205-207 i2-006 Q-1(4-CN) 246-248 i2-010 Q-2(4-F) 186-188 i2-011 Q-2(4-Cl) 243-245 i2-017 Q-3 171-173 i2-018 Q-3(4-F) 211-213 i2-019 Q-3(4-Cl) 199-201 i2-020 Q-3(4-Br) 191-193 i2-023 Q-3(4-CH3) 174-176 i2-025 Q-4 224-226 i2-027 Q-4(4-Cl) 222-224 i2-041 Q-9 206-208 ―――――――――――――――

[0230] [Table 15] ―――――――――――――――――――― No. R1 G mp(℃) ―――――――――――――――――――― i5-003 Cl G-3 181-183 i5-004 Cl G-2 162-164 i5-010 Cl G-1(4-F) 178-180 i5-014 Cl G-3(3-F) 184-186 i5-017 Cl G-2(4-F) 159-161 i5-029 Cl G-3(3-Cl) 174-176 i5-040 Cl G-1(4-CH3) 196-198 i5-044 Cl G-3(3-CH3) 182-184 i5-078 CF3 G-3(3-F) 159-161 ――――――――――――――――――

[0231] Among the compounds of the present invention, compounds for which the melting point is not described １ The H-NMR data are shown in Table 16. The proton nuclear magnetic resonance spectrum (hereinafter referred to as １ The chemical shift values ​​of H-NMR are expressed as Me as a standard substance. ４ Using Si (tetramethylsilane), measurements were made at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). １ The symbols in the H-NMR chemical shift values ​​have the following meanings, and the notation "*2" indicates that no signal corresponding to OH or NH protons was observed: s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, brs: broad singlet

[0232] [Table 16] ------------------------------------------------------------------ No. 1H-NMR (Me4Si) ―――――――――――――――――――――――――――――――――― 2-286 (400MHz, DMSO-d6, *2):δ12.4(brs, 1H), 8.50(brs, 1H), 8.40(brs, 1H), 8.25-8.15(m, 1H), 8.10-8.00(m, 1H), 7.92(brs, 1H), 7.40-7.30(m, 2H), 7.20-7.10(m, 1H), 5.15-4.90(m, 2H), 2.60-3.1(m, 1H). 2-287 (400MHz, DMSO-d6):δ12.1 and 11.9(brs, 1H), 8.7-8.8(m, 2H), 8.5-8.6(brs, 1H), 8.4-8.5(m, 1H), 8.3-8.4(m, 1H), 8.2-8.3(m, 1H), 8.05-8.15(m, 1H), 7.95-8.05(m, 1H), 7.35-7.45(m, 2H), 4.9-5.1(m, 1H), 2.8-3.2(m, 2H). 2-288 (400MHz, DMSO-d6):δ12.4(brs, 1H), 8.9-9.0(m, 1H), 8.7-8.9(brs, 1H), 8.5-8.6(m, 1H), 8.4(brs, 2H), 8.15-8.3(m, 1H), 8.05-8.15(m, 1H), 7.5-7.7(m, 2H), 7.3-7.4(m, 1H), 4.85-4.95(m, 1H), 2.8-3.0(m, 2H). 2-289 (400MHz, DMSO-d6, *2):δ9.68(brs, 1H), 9.02(brs, 1H), 8.5-8.6(m, 2H), 8.4-8.5(m, 1H), 8.2-8.35(m, 2H), 8.1(brs, 1H), 7.7-7.8(m, 1H), 7.35-7.45(m, 1H), 5.05(brs, 1H), 2.8-3.2(m, 2H). 3-165 (400MHz, CDCl3):δ12.1(brs, 1H), 8.77(brs, 1H), 8.47(d, J=4.8Hz, 1H), 8.17(brs, 1H), 7.8-7.95(m, 1H), 7.6-7.7(m, 2H), 7.0-7.15(m, 1H), 5.25-5.55(m, 1H), 3.0-3.1(m, 2H) , 2.07(s, 3H). 3-166 (400MHz, CDCl3):δ10.9(brs, 1H), 8.35-8.5(m, 2H), 7.8-7.95(m, 2H), 7.6-7.7(m, 2H), 6.9-7.1(m, 1H), 5.1-5.2(m, 1H), 3.0-3.3(m, 2H). 3-208 (300MHz, DMSO-d6, *2): 11.90-12.06(m, 1H), 9.63-8.68(m, 1H), 7.67(brs, 1H), 6.39-6.52(m, 1H), 5.23-5.55(m, 1H), 3.91(s, 3H), 3.80(s, 3H), 3.56(dd, J=17.7, 7.5Hz, 1H), 2.86-3.15(m, 1H). 5-001 (400MHz, CDCl3, *2):δ11.7(brs, 1H), 8.37(d, J=5.2Hz, 1H), 8.23(d, J=3.2Hz, 1H), 8.04(dd, J=13.2, 4.0Hz, 1H), 7.8-7.85(m, 1H), 7.57(brs, 1H), 7.4-7.5(m, 1H), 6.0-6.1(m, 1H), 4.46(q, J=7.2Hz, 2H) , 3.45-3.55(m, 1H), 3.25-3.35(m, 1H), 1.43(t, J=7.2Hz, 3H). 5-002 (400MHz, CDCl3, *2):δ11.7(brs, 1H), 8.36(d, J=5.2Hz, 1H), 8.25(d, J=3.2Hz, 1H), 8.08(dd, J=9.2, 4.0Hz, 1H), 7.75-7.85(m, 1H), 7.55(brs, 1H), 7.4-7.5(m, 1H), 6.3-6.4(m, 1H), 3.39(d, J=4.4Hz, 2H) , 3.1-3.2(m, 1H), 2.8-2.9(m, 1H), 2.15-2.25(m, 1H), 1.06(d, J=6.8Hz, 3H), 1.0(d, J=6.8Hz, 3H). 5-004 (400MHz, CDCl3, *2):δ11.5(brs, 1H), 8.37(d, J=5.2Hz, 1H), 8.25(d, J=2.8Hz, 1H), 8.07(dd, J=9.2, 4.0Hz, 1H), 7.75-7.85(m, 1H), 7.55(brs, 1H), 7.4-7.5(m, 1H), 6.4-6.45(m, 1H), 4.92(d, J=18Hz, 1H) , 4.66(d, J=18Hz, 1H), 3.54(s, 3H) , 3.43(d, J=4.4Hz, 2H). 5-005 (400MHz, CDCl3, *2):δ11.7(brs, 1H), 8.37(d, J=5.2Hz, 1H), 8.21(d, J=2.4Hz, 1H), 8.0-8.1(m, 1H), 7.8-7.85(m, 1H), 7.55-7.65(m, 1H), 7.4-7.5(m, 1H), 6.06(dd, J=6.4, 1.6Hz, 1H), 4.02(s, 3H) , 3.4-3.55(m 1H), 3.3-3.4(m, 1H). 5-012 (400MHz, CDCl3, *2):δ11.4(brs, 1H), 8.35-8.45(m, 2H), 8.05-8.15(m, 1H), 7.8-7.85(m, 1H), 7.55-7.6(m, 1H), 6.9-7.0(m, 1H), 6.3-6.4(m, 1H), 3.41(d, J=4.0Hz, 2H), 2.73(s, 3H). 5-014 (400MHz, CDCl3, *2):δ11.5(brs, 1H), 8.37(d, J=5.2Hz, 1H), 8.25(d, J=2.8Hz, 1H), 8.07(dd, J=9.2, 4.0Hz, 1H), 7.75-7.85(m, 1H), 7.55(brs, 1H), 7.4-7.5(m, 1H), 6.4-6.45(m, 1H), 3.65-3.75(m, 4H) , 3.25-3.3(m, 4H) , 2.8-2.9(m, 1H), 2.0-2.2(m, 1H). 5-015 (400MHz, CDCl3, *2):δ11.6(brs, 1H), 8.36(d, J=5.2Hz, 1H), 8.21(d, J=3.2Hz, 1H), 8.06(dd, J=9.2, 4.0Hz, 1H), 7.75-7.85(m, 1H), 7.55-7.65(m, 2H), 7.4-7.5(m, 1H), 7.3-7.35(m, 1H), 6.55-6.6(m, 1H), 5.8-5.85(m 1H), 3.61(dd, J=18.0, 7.2Hz, 1H), 3.3-3.45(m, 1H). ――――――――――――――――――――――――――――――――.

[0233] [Test Examples] Next, the usefulness of the compound of the present invention as a pesticide will be specifically explained in the following test examples, but the present invention is not limited to these.

[0234] Test Example 1: Insecticidal test against brown planthoppers A 10% by mass emulsion of the compound of the present invention prepared according to the above emulsion formulation example was diluted with water containing a spreader to prepare a 500 ppm concentration solution. Rice leaf sheaths were immersed in the solution for approximately 10 seconds. After the immersion procedure was completed, the treated rice leaf sheaths were air-dried and then placed in a test tube. Five third-instar larvae of the brown planthopper (Nilaparvata lugens) were released into each tube, which was then covered with a sponge and placed in a thermostatic chamber at 25°C. Six days after placement, the number of dead brown planthoppers in the test tube was counted, and the mortality rate was calculated using the following formula. The test was conducted in duplicate. Mortality rate (%) = (number of dead insects / number of test insects) x 100

[0235] As a result, the following compounds showed a mortality rate of 90% or more. Compounds of the present invention: 1-001, 1-002, 1-003, 1-013, 1-014, 1-020, 2-001, 2-005, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-016, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2-024, 2-025, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-047, 2-048, 2-049, 2-050, 2-051, 2-052, 2-053, 2-054, 2-055, 2-056, 2-057, 2-058, 2-059, 2-060, 2-061, 2-062, 2-063, 2-067, 2-069, 2-071, 2-074, 2-076, 2-077, 2-079, 2-080, 2-081, 2-082, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-150, 2-151, 2-152, 2-153, 2-154,2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-205, 2-206, 2-207, 2-208, 2-209, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-222, 2-223, 2-227, 2-228, 2-231, 2-232, 2-233, 2-235, 2-238, 2-240, 2-244, 2-245, 2-246, 2-247, 2-248, 2-249, 2-250, 2-251, 2-252, 2-253, 2-254, 2-255, 2-256, 2-259, 2-260, 2-261, 2-262, 2-263, 2-264, 2-265, 2-267, 2-268, 2-269, 2-271, 2-272, 2-273, 2-276, 2-277, 2-287, 2-288, 2-289, 2-290, 2-297, 2-298, 2-299, 2-300, 2-301, 2-302, 2-303, 2-304, 2-305, 3-001, 3-002, 3-005, 3-006, 3-007, 3-009, 3-010, 3-011, 3-012, 3-013, 3-014, 3-015, 3-016, 3-017, 3-018, 3-020, 3-021, 3-022, 3-023, 3-024, 3-025, 3-026, 3-027, 3-028, 3-029, 3-030, 3-031, 3-032, 3-033,3-034, 3-035, 3-036, 3-037, 3-038, 3-039, 3-040, 3-041, 3-042, 3-043, 3-044, 3-045, 3-046, 3-047, 3-048, 3-049, 3-050, 3-051, 3-052, 3-053, 3-055, 3-056, 3-057, 3-058, 3-059, 3-060, 3-061, 3-062, 3-063, 3-064, 3-065, 3-066, 3-067, 3-068, 3-069, 3-070, 3-071, 3-072, 3-073, 3-074, 3-075, 3-076, 3-077, 3-078, 3-079, 3-080, 3-081, 3-082, 3-083, 3-084, 3-085, 3-086, 3-087, 3-088, 3-089, 3-090, 3-091, 3-092, 3-093, 3-094, 3-095, 3-096, 3-097, 3-098, 3-100, 3-102, 3-103, 3-104, 3-105, 3-106, 3-107, 3-108, 3-110, 3-111, 3-112, 3-113, 3-114, 3-115, 3-116, 3-119, 3-121, 3-122, 3-123, 3-126, 3-127, 3-129, 3-130, 3-131, 3-132, 3-133, 3-134, 3-135, 3-136, 3-138, 3-139, 3-140, 3-141, 3-144, 3-146, 3-147, 3-152, 3-153, 3-154, 3-155, 3-156, 3-157, 3-158, 3-159, 3-160, 3-161, 3-162, 3-163, 3-164, 3-165, 3-166, 3-168, 3-169, 3-170, 3-171, 3-172, 3-173, 3-174, 3-175, 3-176, 3-177, 3-178, 3-179, 3-180, 3-182, 3-183, 3-184, 3-185, 3-186, 3-187, 3-188, 3-189, 3-190, 3-191, 3-192, 3-193, 3-194, 3-195, 3-196,3-197, 3-198, 3-199, 3-200, 3-201, 3-202, 3-203, 3-204, 3-205, 3-206, 3-207, 3-208, 3-209, 3-210, 3-213, 3-214, 3-215, 3-216, 3-217, 3-219, 3-220, 3-221, 3-223, 3-224, 3-225, 3-226, 3-227, 3-228, 3-232, 3-233, 3-234, 3-235, 3-236, 3-237, 3-238, 3-239, 3-240, 3-241, 3-242, 3-243, 3-244, 3-245, 3-246, 3-249, 3-250, 3-251, 3-252, 3-253, 3-254, 3-255, 3-256, 3-257, 3-258, 3-259, 3-260, 3-261, 3-262, 3-263, 3-264, 3-265, 3-268, 3-269, 3-270, 3-271, 3-272, 3-273, 3-274, 3-275, 3-276, 3-277, 3-278, 3-279, 3-280, 3-281, 3-283, 3-284, 3-285, 3-286, 3-287, 3-288, 3-289, 3-290, 3-291, 3-292, 3-293, 3-294, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-003, 6-004, 6-005,

[0236] Test Example 2: Insecticidal test against green peach aphids Wet absorbent cotton was placed in a glass petri dish with an inner diameter of 3 cm, and a circular cut-out piece of kale leaves with a diameter of 3 cm was placed on top of it, and four wingless adult green peach aphids (Myzus persicae) were released. One day later, a 10% by mass emulsion of the compound of the present invention prepared according to the above emulsion formulation example was diluted with water containing a spreading agent to prepare a drug solution with a concentration of 500 ppm. The prepared drug solution was sprayed (2.5 mg / cm) using a rotary spray tower.２ ), and the dish was covered and placed in a thermostatic chamber at 25° C. Six days after placement, the number of dead peach aphids in the dish was counted, and the mortality rate was calculated using the same formula as in Test Example 1. The test was conducted in duplicate.

[0237] As a result, the following compounds showed a mortality rate of 90% or more. Compounds of the present invention: 1-001, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-014, 1-015, 1-016, 1-017, 1-019, 1-020, 1-021, 1-023, 2-003, 2-005, 2-007, 2-010, 2-023, 2-032, 2-034, 2-035, 2-036, 2-040, 2-041, 2-042, 2-044, 2-045, 2-046, 2-047, 2-048, 2-049, 2-053, 2-054, 2-056, 2-057, 2-058, 2-062, 2-063, 2-064, 2-067, 2-068, 2-077, 2-083, 2-086, 2-087, 2-091, 2-097, 2-098, 2-099, 2-100, 2-104, 2-112, 2-115, 2-117, 2-120, 2-124, 2-125, 2-126, 2-137, 2-141, 2-146, 2-151, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-163, 2-165, 2-167, 2-169, 2-170, 2-172, 2-173, 2-179, 2-180, 2-182, 2-183, 2-184, 2-186, 2-189, 2-192, 2-194, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-208, 2-213, 2-214, 2-216, 2-217, 2-219, 2-242, 2-244, 2-245, 2-247, 2-250, 2-251, 2-253, 2-254, 2-255, 2-257, 2-264, 2-265, 2-266, 2-267, 2-268, 2-271, 2-273, 2-274, 2-278, 2-280, 2-281, 2-284, 2-285, 2-292, 2-298, 2-303, 3-002, 3-009, 3-011, 3-013, 3-014, 3-015, 3-017,3-020, 3-022, 3-024, 3-027, 3-028, 3-033, 3-039, 3-042, 3-044, 3-049, 3-051, 3-053, 3-054, 3-055, 3-056, 3-058, 3-059, 3-060, 3-064, 3-070, 3-072, 3-074, 3-075, 3-080, 3-095, 3-096, 3-097, 3-098, 3-099, 3-100, 3-107, 3-109, 3-110, 3-111, 3-112, 3-117, 3-118, 3-119, 3-122, 3-123, 3-125, 3-126, 3-128, 3-129, 3-131, 3-132, 3-133, 3-134, 3-136, 3-137, 3-139, 3-142, 3-144, 3-148, 3-164, 3-166, 3-167, 3-170, 3-173, 3-174, 3-178, 3-179, 3-181, 3-183, 3-192, 3-194, 3-196, 3-200, 3-202, 3-204, 3-205, 3-206, 3-207, 3-208, 3-210, 3-213, 3-215, 3-217, 3-219, 3-222, 3-224, 3-225, 3-226, 3-228, 3-229, 3-230, 3-232, 3-236, 3-241, 3-246, 3-248, 3-249, 3-251, 3-252, 3-253, 3-254, 3-257, 3-265, 3-266, 3-268, 3-269, 3-270, 3-271, 3-272, 3-273, 3-274, 3-275, 3-276, 3-277, 3-278, 3-279, 3-280, 3-281, 3-291, 4-001, 5-002, 5-007, 5-009, 5-011, 5-012, 5-013, 5-015, 5-016, 6-001, 6-004,

[0238] Test Example 3: Insecticidal activity against western flower thrips A damp filter paper was placed in a polystyrene cup with an inner diameter of 7 cm, and kidney bean leaves cut into 3 cm squares were placed on top of it. 20 larvae of western flower thrips (Frankliniella occidentalis) were inoculated per leaf. A 10% by mass emulsion of the compound of the present invention prepared according to the above emulsion formulation example was diluted with water containing a spreading agent to prepare a 500 ppm concentration drug solution. The prepared drug solution was sprayed in an amount of 2.5 ml per polystyrene cup using a rotary spray tower (2.5 mg / cm). ２ After two days, the number of dead western flower thrips in the polystyrene cups was counted, and the mortality rate was calculated using the same formula as in Test Example 1. The test was carried out in duplicate.

[0239] As a result, the following compounds showed a mortality rate of 90% or more. Compounds of the present invention: 1-001, 1-002, 1-003, 1-005, 1-007, 1-008, 1-009, 1-010, 1-011, 1-013, 1-014, 1-015, 1-016, 1-017, 1-019, 1-020, 1-022, 1-023, 1-024, 2-001, 2-005, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-016, 2-018, 2-019, 2-020, 2-021, 2-022, 2-024, 2-025, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-040, 2-041, 2-042, 2-044, 2-045, 2-047, 2-048, 2-049, 2-050, 2-053, 2-054, 2-055, 2-056, 2-057, 2-058, 2-059, 2-062, 2-063, 2-067, 2-068, 2-069, 2-071, 2-072, 2-073, 2-074, 2-076, 2-077, 2-078, 2-079, 2-080, 2-081, 2-082, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-099, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141,2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 2-228, 2-229, 2-230, 2-231, 2-232, 2-233, 2-235, 2-238, 2-239, 2-240, 2-244, 2-245, 2-246, 2-247, 2-248, 2-249, 2-250, 2-251, 2-252, 2-253, 2-254, 2-255, 2-256, 2-257, 2-258, 2-259, 2-260, 2-261, 2-262, 2-263, 2-265, 2-269, 2-271, 2-272, 2-273, 2-276, 2-277, 2-279, 2-280, 2-281, 2-282, 2-287, 2-288, 2-296, 2-297, 2-298, 2-299, 2-300, 2-301, 2-302, 2-303, 2-304, 2-305, 3-001, 3-003, 3-005, 3-006, 3-007, 3-009, 3-010, 3-011, 3-012, 3-013, 3-014,3-015, 3-016, 3-018, 3-020, 3-021, 3-022, 3-023, 3-024, 3-025, 3-026, 3-027, 3-028, 3-029, 3-030, 3-031, 3-032, 3-034, 3-035, 3-036, 3-037, 3-038, 3-039, 3-040, 3-041, 3-042, 3-043, 3-044, 3-045, 3-046, 3-047, 3-048, 3-049, 3-050, 3-051, 3-052, 3-054, 3-055, 3-056, 3-057, 3-058, 3-059, 3-060, 3-061, 3-062, 3-063, 3-064, 3-065, 3-066, 3-067, 3-068, 3-069, 3-070, 3-071, 3-072, 3-073, 3-074, 3-075, 3-076, 3-077, 3-078, 3-079, 3-080, 3-081, 3-082, 3-083, 3-084, 3-085, 3-086, 3-088, 3-089, 3-090, 3-091, 3-092, 3-095, 3-096, 3-097, 3-098, 3-100, 3-102, 3-103, 3-104, 3-105, 3-106, 3-107, 3-108, 3-109, 3-111, 3-113, 3-114, 3-115, 3-116, 3-120, 3-121, 3-122, 3-123, 3-124, 3-126, 3-127, 3-128, 3-129, 3-131, 3-132, 3-133, 3-134, 3-135, 3-138, 3-139, 3-140, 3-141, 3-144, 3-145, 3-146, 3-147, 3-154, 3-155, 3-156, 3-157, 3-159, 3-160, 3-161, 3-163, 3-164, 3-165, 3-169, 3-170, 3-171, 3-172, 3-173, 3-174, 3-175, 3-176, 3-177, 3-179, 3-180, 3-183, 3-184, 3-185, 3-186, 3-187, 3-188, 3-189, 3-190, 3-191,3-192, 3-195, 3-197, 3-199, 3-200, 3-202, 3-204, 3-205, 3-206, 3-207, 3-208, 3-209, 3-210, 3-213, 3-214, 3-215, 3-216, 3-217, 3-219, 3-220, 3-221, 3-223, 3-224, 3-225, 3-226, 3-227, 3-228, 3-232, 3-233, 3-234, 3-235, 3-236, 3-238, 3-239, 3-240, 3-241, 3-242, 3-243, 3-244, 3-245, 3-246, 3-249, 3-250, 3-252, 3-253, 3-254, 3-255, 3-256, 3-257, 3-258, 3-259, 3-260, 3-261, 3-262, 3-263, 3-264, 3-265, 3-267, 3-268, 3-269, 3-270, 3-271, 3-272, 3-273, 3-274, 3-275, 3-277, 3-278, 3-279, 3-280, 3-281, 3-282, 3-283, 3-284, 3-285, 3-286, 3-287, 3-288, 3-289, 3-292, 3-294, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-003, 6-004,

[0240] Test Example 4: Insecticidal Test Against Diamondback Moth A 10% by weight emulsion of the compound of the present invention prepared according to the above emulsion formulation example was diluted with water containing a spreading agent to prepare a 500 ppm concentration solution. Cabbage leaves were immersed in the solution for approximately 10 seconds. After the immersion procedure was completed, the treated cabbage leaves were air-dried and then placed in a petri dish. Five third-instar larvae of diamondback moth (Plutella xylostella) were released into the dish, and the dish was covered and placed in a thermostatic chamber at 25°C. Six days after placement, the number of dead diamondback moths in the dish was counted, and the mortality rate was calculated using the same formula as in Test Example 1. The test was conducted in duplicate.

[0241] As a result, the following compounds showed a mortality rate of 90% or more. Compounds of the present invention: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-022, 1-023, 1-024, 2-001, 2-005, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-022, 2-024, 2-025, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-038, 2-039, 2-040, 2-041, 2-042, 2-044, 2-045, 2-048, 2-049, 2-050, 2-055, 2-057, 2-058, 2-060, 2-061, 2-062, 2-063, 2-064, 2-066, 2-067, 2-068, 2-069, 2-072, 2-073, 2-076, 2-077, 2-078, 2-079, 2-080, 2-081, 2-082, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-117, 2-118, 2-119, 2-121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140,2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-163, 2-164, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-181, 2-182, 2-183, 2-184, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-205, 2-206, 2-207, 2-208, 2-209, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 2-228, 2-229, 2-231, 2-232, 2-233, 2-234, 2-235, 2-237, 2-240, 2-241, 2-242, 2-243, 2-244, 2-245, 2-246, 2-247, 2-248, 2-249, 2-250, 2-251, 2-252, 2-253, 2-254, 2-255, 2-256, 2-257, 2-259, 2-260, 2-261, 2-262, 2-263, 2-264, 2-265, 2-267, 2-268, 2-269, 2-271, 2-272, 2-273, 2-274, 2-276, 2-277, 2-278, 2-279, 2-280, 2-282, 2-283, 2-287, 2-288, 2-295, 2-297, 2-298, 2-299, 2-300, 2-301, 2-302, 2-303, 2-304, 2-305, 3-001, 3-002, 3-003,3-004, 3-005, 3-006, 3-007, 3-009, 3-010, 3-011, 3-012, 3-013, 3-014, 3-015, 3-016, 3-017, 3-018, 3-019, 3-020, 3-021, 3-022, 3-023, 3-024, 3-025, 3-026, 3-027, 3-028, 3-029, 3-030, 3-031, 3-032, 3-033, 3-034, 3-035, 3-036, 3-037, 3-038, 3-039, 3-040, 3-041, 3-042, 3-043, 3-044, 3-046, 3-048, 3-049, 3-050, 3-051, 3-052, 3-053, 3-054, 3-055, 3-056, 3-057, 3-058, 3-059, 3-060, 3-061, 3-062, 3-063, 3-064, 3-065, 3-066, 3-067, 3-068, 3-069, 3-070, 3-071, 3-072, 3-073, 3-074, 3-075, 3-076, 3-077, 3-078, 3-079, 3-080, 3-081, 3-082, 3-083, 3-084, 3-085, 3-086, 3-088, 3-089, 3-090, 3-092, 3-093, 3-095, 3-096, 3-097, 3-098, 3-099, 3-100, 3-102, 3-103, 3-104, 3-105, 3-106, 3-107, 3-108, 3-109, 3-110, 3-113, 3-114, 3-115, 3-116, 3-119, 3-122, 3-123, 3-124, 3-125, 3-126, 3-127, 3-128, 3-129, 3-131, 3-132, 3-133, 3-134, 3-135, 3-136, 3-138, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144, 3-145, 3-146, 3-147, 3-154, 3-155, 3-156, 3-157, 3-158, 3-159, 3-160, 3-161, 3-162, 3-163, 3-164, 3-165, 3-166, 3-169,3-170, 3-172, 3-173, 3-174, 3-175, 3-176, 3-177, 3-178, 3-179, 3-180, 3-183, 3-184, 3-185, 3-186, 3-187, 3-188, 3-189, 3-190, 3-191, 3-192, 3-193, 3-194, 3-195, 3-196, 3-197, 3-198, 3-199, 3-200, 3-202, 3-203, 3-204, 3-205, 3-207, 3-208, 3-209, 3-210, 3-212, 3-213, 3-214, 3-215, 3-216, 3-217, 3-219, 3-220, 3-221, 3-222, 3-223, 3-224, 3-225, 3-226, 3-227, 3-228, 3-230, 3-232, 3-233, 3-234, 3-235, 3-236, 3-237, 3-238, 3-239, 3-240, 3-241, 3-243, 3-244, 3-246, 3-248, 3-249, 3-251, 3-252, 3-253, 3-254, 3-255, 3-256, 3-257, 3-258, 3-259, 3-260, 3-262, 3-263, 3-264, 3-265, 3-268, 3-269, 3-270, 3-271, 3-272, 3-273, 3-274, 3-275, 3-276, 3-277, 3-279, 3-280, 3-281, 3-282, 3-283, 3-284, 3-285, 3-286, 3-292, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-003, 6-004, 6-005,

[0242] Test Example 5: Test of efficacy against Rhipicephalus sanguineus 1 mg of the compound of the present invention was dissolved in 1 ml of acetone to prepare a drug solution with a concentration of 1000 ppm. ２After coating the bottom and side of a glass container, the acetone was evaporated to form a thin film of the compound on the inner wall of the glass container. ２ The treatment amount is 10 μg / cm ２ It was.

[0243] Five primary nymphs of brown dog ticks (Rhipicephalus sanguineus) (mixed sexes) were released into the treated glass container, which was then covered and placed in a thermostatic chamber at 25° C. Two days after release, the number of dead ticks was counted, and the mortality rate was calculated using the same formula as in Test Example 1.

[0244] As a result, the following compounds showed insect mortality rates of 50% or more: Compounds of the present invention: 1-006, 1-007, 2-120, 2-127, 2-128, 2-151, 2-153, 3-082, 3-100, 3-101, 3-114, 3-128, 3-129, 3-166, 3-186, 3-200, 3-208

[0245] Test Example 6: Test of effectiveness against cat fleas 1 mg of the compound of the present invention was dissolved in 1 ml of acetone to prepare a drug solution with a concentration of 1000 ppm. ２ After coating the bottom and side surfaces of a glass container, the acetone was evaporated to form a thin film of the compound on the inner wall of the glass container. ２ The treatment amount is 10 μg / cm ２ It was.

[0246] Five adult cat fleas (Ctenocephalides felis) (male and female mixed) were released into the treated glass container, which was then covered and placed in a thermostatic chamber at 25° C. Three days after release, the number of dead fleas was counted, and the mortality rate was calculated using the same formula as in Test Example 1.

[0247] As a result, the following compounds showed a mortality rate of 50% or more. Compounds of the present invention: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-011, 1-012, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-023, 1-024, 2-001, 2-005, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-018, 2-019, 2-020, 2-021, 2-022, 2-024, 2-025, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-040, 2-041, 2-042, 2-044, 2-045, 2-047, 2-049, 2-058, 2-062, 2-063, 2-065, 2-067, 2-068, 2-069, 2-071, 2-072, 2-073, 2-076, 2-077, 2-078, 2-079, 2-080, 2-081, 2-082, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-144, 2-145, 2-146, 2-147, 2-148,2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-205, 2-206, 2-207, 2-208, 2-209, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 2-228, 2-229, 2-231, 2-232, 2-233, 2-235, 2-238, 2-240, 2-244, 2-245, 2-246, 2-247, 2-248, 2-249, 2-250, 2-251, 2-252, 2-253, 2-254, 2-255, 2-256, 2-257, 2-259, 2-260, 2-261, 2-263, 2-264, 2-267, 2-269, 2-270, 2-271, 2-272, 2-273, 2-274, 2-275, 2-276, 2-277, 2-278, 2-279, 2-280, 2-282, 2-283, 2-290, 2-297, 2-298, 2-299, 2-300, 2-301, 2-302, 2-303, 2-304, 2-305, 3-001, 3-003, 3-005, 3-006, 3-007, 3-009, 3-010, 3-011, 3-012, 3-013, 3-014, 3-016, 3-018, 3-019, 3-020,3-021, 3-022, 3-023, 3-024, 3-025, 3-026, 3-027, 3-028, 3-029, 3-030, 3-031, 3-032, 3-033, 3-034, 3-035, 3-036, 3-037, 3-039, 3-040, 3-042, 3-043, 3-044, 3-045, 3-047, 3-048, 3-049, 3-050, 3-053, 3-055, 3-056, 3-057, 3-058, 3-059, 3-060, 3-061, 3-062, 3-063, 3-064, 3-065, 3-066, 3-068, 3-069, 3-071, 3-072, 3-073, 3-074, 3-075, 3-076, 3-077, 3-079, 3-080, 3-081, 3-082, 3-083, 3-084, 3-085, 3-086, 3-088, 3-089, 3-090, 3-091, 3-092, 3-093, 3-094, 3-095, 3-096, 3-097, 3-098, 3-100, 3-101, 3-102, 3-103, 3-105, 3-106, 3-107, 3-108, 3-109, 3-110, 3-113, 3-114, 3-115, 3-121, 3-122, 3-123, 3-127, 3-128, 3-129, 3-131, 3-132, 3-133, 3-135, 3-136, 3-138, 3-139, 3-140, 3-141, 3-144, 3-145, 3-146, 3-154, 3-155, 3-156, 3-157, 3-158, 3-159, 3-160, 3-161, 3-164, 3-166, 3-167, 3-168, 3-169, 3-170, 3-171, 3-172, 3-173, 3-174, 3-175, 3-176, 3-177, 3-178, 3-179, 3-180, 3-181, 3-182, 3-183, 3-184, 3-185, 3-186, 3-187, 3-188, 3-189, 3-190, 3-191, 3-192, 3-193, 3-194, 3-195, 3-196, 3-197, 3-199, 3-200, 3-203,3-205, 3-207, 3-208, 3-209, 3-210, 3-212, 3-213, 3-214, 3-215, 3-216, 3-217, 3-219, 3-220, 3-221, 3-222, 3-223, 3-224, 3-225, 3-226, 3-227, 3-228, 3-232, 3-233, 3-234, 3-235, 3-236, 3-237, 3-238, 3-239, 3-243, 3-246, 3-248, 3-249, 3-254, 3-257, 3-263, 3-264, 3-265, 3-268, 3-269, 3-270, 3-271, 3-272, 3-273, 3-274, 3-275, 3-277, 3-278, 3-280, 3-281, 3-282, 3-283, 3-284, 3-285, 3-286, 3-287, 3-291, 3-292, 3-294, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-004, 6-005,

[0248] Test Example 7: Efficacy Test Against Trichostrongylus axei After dispensing 60 μl of 1% potato dextrose agar medium into a 96-well plate, 30 μl of sterile water containing Trichostrongylus axei eggs and lyophilized E. coli OP50 strain (5 eggs, 10 μg E. coli / 10 μl) was added to each well. 10 μl of test solution B containing the compound of the present invention was added to each well and allowed to stand at 25°C in the dark. Four days after the addition of the drug, the numbers of unhatched eggs and inactive larvae were counted, and the efficacy (%) relative to the untreated group was calculated using the following formula: efficacy (%) = [(number of unhatched eggs + number of inactive larvae in the treated group) / (number of unhatched eggs + number of inactive larvae + number of active larvae in the untreated group)] × 100

[0249] As a result, of the compounds tested, the following compounds showed efficacy (%) of 50% or more. Compounds of the present invention: 2-003, 2-035, 2-038, 2-056, 2-070, 2-088, 2-103, 2-115, 2-120, 2-126, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-136, 2-138, 2-139, 2-142, 2-144, 2-145, 2-147, 2-153, 2-155, 2-156, 2-158, 2-160, 2-161, 2-164, 2-165, 2-166, 2-167, 2-169, 2-170, 2-171, 2-172, 2-173, 2-177, 2-179, 2-180, 2-181, 2-184, 2-188, 2-191, 2-192, 2-193, 2-194, 2-197, 2-201, 2-202, 2-203, 2-204, 2-206, 2-208, 2-211, 2-214, 2-218, 2-219, 2-220, 2-221, 2-225, 2-229, 2-232, 2-234, 2-235, 2-238, 2-239, 2-240, 2-244, 2-245, 2-246, 2-247, 2-248, 2-249, 2-250, 2-251, 2-252, 2-254, 2-255, 2-256, 2-262, 2-263, 2-264, 2-266, 2-270, 2-271, 2-272, 2-273, 2-274, 2-275, 2-277, 2-278, 2-279, 2-289, 2-290, 2-291, 2-292, 2-296, 2-297, 2-299, 2-303, 2-304, 3-011, 3-027, 3-031, 3-060, 3-061, 3-064, 3-065, 3-070, 3-071, 3-074, 3-076, 3-078, 3-082, 3-083, 3-085, 3-086, 3-087, 3-089, 3-097, 3-098, 3-100, 3-102, 3-107, 3-110, 3-114, 3-117, 3-121, 3-124, 3-125, 3-126, 3-127, 3-128,3-129, 3-136, 3-137, 3-138, 3-139, 3-141, 3-143, 3-144, 3-145, 3-146, 3-148, 3-152, 3-154, 3-155, 3-157, 3-158, 3-161, 3-163, 3-164, 3-166, 3-169, 3-170, 3-171, 3-174, 3-175, 3-180, 3-183, 3-190, 3-192, 3-195, 3-199, 3-202, 3-209, 3-211, 3-216, 3-222, 3-226, 3-232, 3-233, 3-237, 3-239, 3-249, 3-250, 3-261, 3-263, 3-267, 3-268, 3-270, 3-271, 3-274, 3-275, 3-277, 3-279, 3-283, 3-285, 3-293, 5-001, 5-004, 5-005, 5-006, 5-007, 5-009, 5-010, 5-011, 5-012, 5-013, 5-015, 5-016, 6-001,

[0250] The aryltetrahydropyridine compound or a salt thereof of the present invention has excellent pesticidal activity and can be used as a pesticide.

Claims

1. Formula (1): 【Chemistry 1】 [In the formula, Q is Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-2 9, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56, 【Chemistry 2】 【Transformation 3】 Z ６ is a halogen atom, C １ -C ６ alkyl, C ２ -C ６ alkenyl, C ２ -C ６ alkynyl, halo(C １ -C ６ alkyl, halo(C ２ -C ６ alkenyl, halo(C ２ -C ６ alkynyl, C １ -C ６ alkoxy, halo(C １ -C ６ alkoxy, C ２ -C ６ alkoxy(C １ -C ６ alkoxy, C ２ -C ６ alkenyloxy, halo(C ２ -C ６ alkenyloxy, C ２ -C ６ alkynyloxy, halo(C ２ -C ６ alkynyloxy, C １ -C ６ alkylthio, C １ -C ６ alkylsulfinyl, C １ -C · ６ alkylsulfonyl, halo(C １ -C ６ alkylthio, halo(C １ -C ６ alkylsulfinyl, halo(C １ -C ６ alkylsulfonyl, C ２ -C ６ alkenylthio, C ２ -C ６ alkenylsulfinyl, C ２ -C ６ alkenylsulfonyl, halo(C ２ -C ６ alkenylthio, halo(C ２ -C ６ alkenylsulfinyl, halo(C ２ to C ６ ), alkenylsulfonyl, C ２ to C ６ alkynylthio, C ２ to C ６ alkynylsulfinyl, C ２ to C ６ alkynylsulfonyl, halo(C ２ to C ６ ), alkynylthio, halo(C ２ to C ６ ), alkynylsulfinyl, halo(C ２ to C ６ ), alkynylsulfonyl, -NH ２ , C １ to C ６ alkylamino, di(C １ to C ６ ), alkylamino, halo(C １ to C ６ ), alkylamino, dihalo(C １ to C ６ ), alkylamino, formyl, carboxy, C １ to C ６ alkylcarbonyl, halo(C １ to C ６ ), alkylcarbonyl, C １ to C ６ alkoxycarbonyl, halo(C １ to C ６ ), alkoxycarbonyl, C １ to C ６ alkylaminocarbonyl, halo(C １ to C ６ ), alkylaminocarbonyl, di(C １ to C ６ ), alkylaminocarbonyl, hydroxy, C １ to C ６ alkylcarbonyloxy, C １ to C ６ alkoxycarbonyloxy, C １ to C ６ alkylsulfonyloxy, halo(C １ to C ６ ), alkylsulfonyloxy, -SO ３ H, C １ to C ６ Alkylaminosulfonyl, di(C) １ ~C ６ ) Alkylaminosulfonyl, -C (=NOR １２ ) R １３ , represents cyano or nitro, R １２ is a hydrogen atom or C １ ~C ６ Represents alkyl, R １３ is a hydrogen atom or C １ ~C ６ Represents alkyl, Z ３ is a hydrogen atom or C １ ~C ６ Represents alkyl, J represents J-1 or J-2, 【Chemistry 4】 A １ This represents a nitrogen atom or CH, G is G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-1 8, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-3 2, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-4 7, represents G-48, G-49, G-50, G-51, G-52, G-53, G-55, G-56, G-57, G-58, G-59, G-60 or G-61, 【Transformation 5】 【Transformation 6】 Z ２ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinil, Halo (C １ ~C ６ ) alkyl, halo(C ２ ~C ６ ) Alkenil, Halo (C ２ ~C ６ ) Alkinyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkoxy (C １ ~C ６ ) Alkoxy, C ２ ~C ６ Alkenyloxy, Halo (C) ２ ~C ６ ) Alkenyloxy, C ２ ~C ６ Alkinyloxy, Halo(C) ２ ~C ６ ) Alkynyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkylthio, Halo (C １ ~C ６ ) Alkyl sulfinyl, halo (C １ ~C ６ ) Alkyl sulfonyl, C ２ ~C ６ Alkenilthio, C ２ ~C ６ Alkenyl sulfinyl, C ２ ~C ６ Alkenylsulfonyl, Halo(C) ２ ~C ６ ) Alkenilchio, Halo (C ２ ~C ６ ) Alkenylsulfinyl, Halo (C ２ ~C ６ ) Alkenylsulfonyl, C ２ ~C ６ Alkinylthio, C ２ ~C ６ Alkinylsulfinyl, C ２ ~C ６ Alkinyl sulfonyl, Halo (C) ２ ~C ６ ) Alkinylthio, Halo (C ２ ~C ６ ) Alkinylsulfinyl, Halo (C ２ ~C ６ ) Alkinylsulfonyl, -NH ２ , C １ ~C ６ Alkylamino, di(C) １ ~C ６ ) alkylamino, halo(C １ ~C ６ ) alkylamino, dihalo(C １ ~C ６ ) Alkylamino, formyl, carboxy, C １ ~C ６ Alkylcarbonyl, Halo(C) １ ~C ６ ) Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, Halo(C) １ ~C ６ ) Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, Halo(C) １ ~C ６ ) Alkylaminocarbonyl, di(C １ ~C ６ ) Alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkoxycarbonyloxy, C １ ~C ６ Alkyl sulfonyl oxy, halo(C) １ ~C ６ ) Alkyl sulfonyl oxy, -SO ３ H, C １ ~C ６ Alkylaminosulfonyl, di(C) １ ~C ６ ) Alkylaminosulfonyl, -C (=NOR １４ ) R １５ , represents nitro or cyano, R １４ is a hydrogen atom or C １ ~C ６ Represents alkyl, R １５ is a hydrogen atom or C １ ~C ６ Represents alkyl, Z ４ C １ ~C ６ Represents alkyl, R １ is a hydrogen atom, a halogen atom, halo (C) １ ~C ６ ) Alkyl, C １ ~C ６ Represents alkyl or cyano, R ２ C is a hydrogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, -C(O)R ４ , -C(O)OR ５ , represents D-1, D-2, or D-3, 【Transformation 7】 R ４ C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkylcarbonyl, di(C) １ ~C ６ ) Alkylamino or R ６ Replaced with (C １ ~C ６ ) Represents alkyl, R ６ C is a halogen atom. １ ~C ６ Alkoxy, cyano, nitro, phenyl, or R ８ This represents phenyl substituted with, Z ５ C is a halogen atom. １ ~C ６ Alkyl, C １ ~C ６ Represents alkoxy, cyano, or nitro, R ８ C is a halogen atom. １ ~C ６ Alkyl, C １ ~C ６ Represents alkoxy, cyano, or nitro, R ５ C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, R ９ Replaced with (C １ ~C ６ ) alkyl, phenyl or R １０ This represents phenyl substituted with, R ９ C is a halogen atom. １ ~C ６ Alkoxy, cyano, nitro, phenyl, or R １１ This represents phenyl substituted with, R １０ C is a halogen atom. １ ~C ６ Alkyl, C １ ~C ６ Represents alkoxy, cyano, or nitro, R １１ C is a halogen atom. １ ~C ６ Alkyl, C １ ~C ６ Represents alkoxy, cyano, or nitro, R ３ C is a hydrogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl or C １ ~C ６ Represents alkylcarbonyl, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom. t1 represents an integer of 0 or 1. t2 represents an integer of 0, 1, or 2. t3 represents an integer of 0, 1, 2, or 3. t4 represents an integer of 0, 1, 2, 3, or 4. t5 represents an integer of 0, 1, 2, 3, 4, or 5. t8 represents an integer of 0, 1, 2, 3, or 4. ] An aryltetrahydropyridine compound or a salt thereof represented by [ ].

2. A １ The aryltetrahydropyridine compound or salt thereof according to claim 1, which represents a nitrogen atom.

3. Z １ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinil, Halo (C １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkylthio, Halo (C １ ~C ６ ) Alkyl sulfinyl, halo (C １ ~C ６ ) Alkylsulfonyl, -NH ２ , C １ ~C ６ Alkylamino, di(C) １ ~C ６ ) Alkylamino, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C) １ ~C ６ ) Alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Represents alkylsulfonyloxy, cyano, or nitro, Z ２ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinil, Halo (C １ ~C ６ ) alkyl, halo(C ２ ~C ６ ) Alkenil, Halo (C ２ ~C ６ ) Alkinyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkylthio, Halo (C １ ~C ６ ) Alkyl sulfinyl, halo (C １ ~C ６ ) Alkylsulfonyl, -NH ２ , C １ ~C ６ Alkylamino, di(C) １ ~C ６ ) Alkylamino, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C) １ ~C ６ ) Alkylaminocarbonyl, hydroxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkyl sulfonyl oxy, -C (=NOR) １４ ) R １５ , represents nitro or cyano, Z ５ C is a halogen atom. １ ~C ６ Alkyl or C １ ~C ６ Represents alkoxy, R １ is a hydrogen atom, a halogen atom, or halo (C １ ~C ６ ) Represents alkyl, R ２ This is a hydrogen atom, -C(O)R ４ , -C(O)OR ５ , represents D-1, D-2, or D-3, R ３ This represents a hydrogen atom, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52, or Q-54. The aryltetrahydropyridine compound or salt thereof according to claim 1, wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55, or G-57.

4. J represents J-1, A １ The aryltetrahydropyridine compound or salt thereof according to claim 1, which represents a nitrogen atom.

5. J represents J-2, the aryltetrahydropyridine compound or salt thereof according to claim 1.

6. The aryltetrahydropyridine compound or salt thereof according to claim 1, wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55, or G-57.

7. Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45, or Q-52. Z １ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinil, Halo (C １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkylthio, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Represents alkylaminocarbonyl, hydroxy, cyano, or nitro, G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40. Z ２ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, Halo (C １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C) １ ~C ６ ) Alkylamino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, hydroxy, -C(=NOR) １４ ) R １５ , represents nitro or cyano, R １４ C １ ~C ６ Represents alkyl, R １ is a hydrogen atom, a halogen atom, or halo (C １ ~C ６ ) Represents alkyl, R ２ This is a hydrogen atom, -C(O)R ４ , -C(O)OR ５ , represents D-1, D-2, or D-3, R ４ C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkylcarbonyl or R ６ Replaced with (C １ ~C ６ ) Represents alkyl, R ６ is a halogen atom or C １ ~C ６ Represents alkoxy, Z ５ C １ ~C ６ Represents alkyl, R ５ C １ ~C ６ Alkyl or C ２ ~C ６ Representing Alkenil, R ３ This represents a hydrogen atom, X represents an oxygen atom in the aryltetrahydropyridine compound or salt thereof according to claim 1.

8. Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, or Q-45. Z １ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkylthio, C １ ~C ６ Represents alkoxycarbonyl, cyano, or nitro, Z ３ C １ ~C ６ Represents alkyl, Z ２ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ The aryltetrahydropyridine compound or salt thereof according to claim 7, representing alkylsulfonyl, hydroxy, nitro, or cyano.

9. J represents J-1, A １ This represents a nitrogen atom, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-12, Q-13, Q-14, or Q-22. G represents G-1, G-3, G-4, or G-5. Z ２ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Represents alkoxy or nitro, R ２ is a hydrogen atom or -C(O)OR ５ This represents, R ５ C １ ~C ６ Represents alkyl, Y represents an oxygen atom. The aryltetrahydropyridine compound or salt thereof according to claim 8.

10. Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, or Q-12. Z １ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Represents alkyl, cyano, or nitro, G represents G-1 or G-3, Z ２ C is a halogen atom. １ ~C ６ Alkyl or halo(C) １ ~C ６ ) Represents alkyl, R １ is a halogen atom or halo (C １ ~C ６ ) Represents alkyl, R ２ The aryltetrahydropyridine compound or salt thereof according to claim 9, where is a hydrogen atom.

11. J represents J-2, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, Q-12, Q-20, Q-29, or Q-45. Z １ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Represents alkoxycarbonyl, cyano, or nitro, G represents G-1, G-3, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40. Z ２ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ The aryltetrahydropyridine compound or salt thereof according to claim 8, representing alkylsulfonyl or hydroxyl.

12. Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, or Q-12. Z １ C is a halogen atom. １ ~C ６ Alkyl, Halo(C) １ ~C ６ ) Represents alkyl, cyano, or nitro, G represents G-1, G-3, or G-7. Z ２ C is a halogen atom. １ ~C ６ Alkyl or halo(C) １ ~C ６ ) Represents alkyl, R ２ The aryltetrahydropyridine compound or salt thereof according to claim 11, where is a hydrogen atom.

13. Formula (1-1): 【Transformation 8】 [In the formula, J represents J-1 or J-2, 【Chemistry 9】 A １ This represents a nitrogen atom, G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40. 【Chemistry 10】 Z ２ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, Halo (C １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C) １ ~C ６ ) Alkylamino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxyarbonyl, hydroxy, -C(=NOR) １４ ) R １５ , represents nitro or cyano, R １４ C １ ~C ６ Represents alkyl, R １５ is a hydrogen atom or C １ ~C ６ Represents alkyl, R1 is a hydrogen atom, a halogen atom, or a halo (C １ ~C ６ ) Represents alkyl, R ５１ C １ ~C ６ Represents alkyl, t2 represents an integer of 0, 1, or 2. t3 represents an integer of 0, 1, 2, or 3. t4 represents an integer of 0, 1, 2, 3, or 4. A production intermediate for an aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 12, represented as [ ].

14. J represents J-1, G represents G-1 or G-3, Z ２ is a halogen atom or C １ ~C ６ Represents alkyl, R １ is a halogen atom or halo (C １ ~C ６ ) A production intermediate for an aryltetrahydropyridine compound or a salt thereof according to claim 13, representing an alkyl group.

15. Formula (1-2): 【Chemistry 11】 [In the formula, R ５２ is a hydrogen atom or C １ ~C ６ Represents alkyl, R ２ This is a hydrogen atom, -C(O)R ４ OR -C(O)OR ５ This represents, R ４ C １ ~C ６ Represents alkyl, R ５ C １ ~C ６ Represents alkyl, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45, or Q-52. 【Chemistry 12】 Z １ C is a halogen atom. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinil, Halo (C １ ~C ６ ) Alkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkylthio, carboxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Represents alkylaminocarbonyl, hydroxy, cyano, or nitro, Z ３ is a hydrogen atom or C １ ~C ６ Represents alkyl, t1 represents an integer of 0 or 1. t2 represents an integer of 0, 1, or 2. t3 represents an integer of 0, 1, 2, or 3. t4 represents an integer of 0, 1, 2, 3, or 4. t5 represents an integer of 0, 1, 2, 3, 4, or 5. A production intermediate for an aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 12, represented as [ ].

16. Q represents Q-1, Q-2, Q-3, Q-4, Q-6, or Q-9. Z １ C is a halogen atom. １ ~C ６ Represents alkyl or cyano, R ２ is a hydrogen atom or -C(O)OR ５ A production intermediate for an aryltetrahydropyridine compound or a salt thereof according to claim 15.

17. A pest control agent containing one or more selected from the aryltetrahydropyridine compounds and salts thereof described in any one of claims 1 to 12 as an active ingredient.

18. A pesticide containing one or more selected from the aryltetrahydropyridine compounds and salts thereof described in any one of claims 1 to 12 as an active ingredient.

19. A control agent for internal or external parasites of mammals or birds, comprising one or more selected from the aryltetrahydropyridine compounds and salts thereof described in any one of claims 1 to 12 as an active ingredient.

20. The control agent according to claim 19, wherein the external parasite is a flea or mite.

21. An insecticide or acaricide containing one or more selected from the aryltetrahydropyridine compounds and salts thereof described in any one of claims 1 to 12 as an active ingredient.

22. A seed treatment agent containing one or more selected from the aryltetrahydropyridine compounds and salts thereof described in any one of claims 1 to 12 as an active ingredient.

23. The seed treatment agent according to claim 22, wherein the seed treatment is performed by immersion treatment.

24. A soil treatment agent containing one or more aryltetrahydropyridine compounds selected from any one of claims 1 to 12 as an active ingredient.

25. The soil treatment agent according to claim 24, wherein the soil treatment is performed by soil drenching.

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