N-benzylamide compounds and pest control agents

Abstract

To provide an excellent pest control agent 【Solution means】General formula [I] 【Chemical formula 1】 JPEG2026077605000071.jpg4066[wherein, R 1 , R 4 each independently represents a substituent such as an alkyl group, R 2 , R 3 , R 5 each independently represents a hydrogen atom or a substituent such as an alkyl group, and R 6 represents a hydrogen atom or a halogen atom.]. Provided are N-benzylamide compounds represented by the formula or salts thereof, and pest control agents containing them as active ingredients.

Description

[Technical Field]

[0001] The present invention relates to a novel N-benzylamide compound or a salt thereof, and a pest control agent containing the compound as an active ingredient. [Background technology]

[0002] Patent Document 1 describes a compound having both an amide and a sulfonamide skeleton that possesses pest control agent activity.

[0003] The above-mentioned patent documents do not contain any description of the N-benzylamide compound that is the subject of this invention. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2024 / 146945 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] Numerous pesticides are used to control harmful organisms in the cultivation of useful crops. However, conventional pest control agents often have insufficient efficacy, or their use is restricted due to the emergence of pests that have developed resistance to them, making them far from satisfactory. Therefore, there is a strong demand for the development of pest control agents that have fewer of these drawbacks and exhibit superior control effects against harmful organisms. [Means for solving the problem]

[0006] The inventors synthesized various N-benzylamide compounds and diligently studied their physiological activity in order to develop a pest control agent having the desirable properties described above. They found that the N-benzylamide compound represented by the following general formula [I] (hereinafter also referred to as the compound of the present invention) has an excellent control effect against pests, and further research led to the completion of the present invention.

[0007] In other words, the present invention has the following characteristics: (1) General formula [I] [ka] [In the formula, R 1 C1-C6 alkyl groups, C2-C6 alkenyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, C1-C6 alkylthio C1-C6 alkyl groups, C1-C6 alkylsulfinyl C1-C6 alkyl groups, C1-C6 alkylsulfonyl C1-C6 alkyl groups, C1-C6 haloalkylthio C1-C6 alkyl groups, C1-C6 haloalkylsulfinyl C1-C6 alkyl groups, C1-C6 haloalkylsulfonyl C1-C6 alkyl groups, cyano C1- The following are represented: C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 haloalkoxy, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C1-C6 alkylamino group (the amino group may be substituted with a C1-C6 alkyl group), phenyloxy group (the phenyl group may be monosubstituted with a nitro group), R 2 This represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxyC1-C6 alkyl group, a C1-C6 alkylcarbonyl group, or a C1-C6 alkoxycarbonyl group. R 3 This represents a hydrogen atom, a halogen atom, a nitro group, or a C1-C6 alkyl group. R 4This represents a halogen atom, a nitro group, a C1-C6 alkyl group, or a C1-C6 alkoxy group. R 5 This represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyano C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylcarbonyl group, a C3-C6 cycloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylcarbonyloxy C1-C6 alkyl group, or a C1-C6 alkoxycarbonyloxy C1-C6 alkyl group. R 6 [This indicates a hydrogen atom or a halogen atom.] A compound represented by, or a salt thereof. (2) A pesticide composition containing the compound described in (1) above, or a salt thereof, as an active ingredient. (3) The pesticide composition according to (2) above, further comprising a surfactant. (4) A pest control agent containing the compound described in (1) above, or a salt thereof, as an active ingredient. (5) The pest control agent described in (4) above, wherein the pest control agent is an insecticide, a nematode, and a miticide. (6) A pest control agent as described in (5) above, which has control efficacy against pests in paddy fields, cultivated fields, lawns, orchards, non-agricultural land, greenhouses, seedling facilities, and plant factories where agricultural and horticultural plants are cultivated. (7) The pest control agent described in (6) above, wherein the agricultural and horticultural plant is a plant to which resistance has been conferred by breeding methods or genetic modification technology. (8) A method for controlling pests using the active ingredient amount of the compound or salt thereof described in (1) above. (9) A method for controlling harmful organisms by simultaneously or in stages applying a pesticide composition containing the compound described in (1) above, or a salt thereof, to agricultural and horticultural crops or to the place where agricultural and horticultural crops are to be grown or are growing. (10) A method for controlling harmful organisms as described in (8) or (9) above, wherein the place where the pest control agent is applied is a paddy field, a field, a lawn, an orchard, non-agricultural land, a greenhouse, a seedling facility, or a plant factory. (11) A method for controlling harmful organisms as described in (8) or (9) above, using the compound described in (1) above, or a salt thereof, as an insecticide, nematodeicide, and acaricide. (12) The method for controlling harmful organisms as described in (10) above, using the compound described in (1) above, or a salt thereof, as an insecticide, nematodeicide, and acaricide. (13) A method of using the pest control agent described in any of (4) to (7) above for the purpose of controlling pests that harm agricultural and horticultural crops. [Effects of the Invention]

[0008] The pest control agent containing the compound of the present invention exhibits excellent control effects against a wide range of pests, including hemipterans, lepidopterans, beetles, flies, hymenopterans, orthopterans, cockroaches, thrips, mites, and plant parasitic nematodes, and can also control pests that have acquired resistance to the agent. [Modes for carrying out the invention]

[0009] This section explains the symbols and terms used in this specification.

[0010] In this invention, "pest control agent" means insecticides, acaricides, nematodeicides, etc., used in agriculture and horticulture, for livestock and pets, for household use or disease control.

[0011] In this invention, "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0012] In this invention, the notation "C1~C6" indicates that the number of carbon atoms in the substituent following it is 1 to 6 in this case.

[0013] In the present invention, unless otherwise specified, "C1-C6 alkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms, and examples of such groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

[0014] In the present invention, "C2-C6 alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, unless otherwise specified. Examples include vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, and 1-ethyl-2-propenyl. Lopenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1- Vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1-(isobutyl)vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-isopropyl-2-propenyl, 2-methyl-2 Examples of groups include -pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl, or 2,4-hexadienyl.

[0015] In the present invention, "C1-C6 haloalkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with the same or different halogen atoms 1 to 13, unless otherwise specified. Examples include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2 -Trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 1-fluoro-2-propyl, 2-fluoro-2-propyl, 1,1-difluoro-2-propyl, 1,2-difluoro-2-propyl, 1,3-difluoro-2-propyl, 1,2,3-trifluoro-2-propyl, 1,1,3,3-tetrafluoro-2-propyl, 1,1,1,3,3 ,3-Hexafluoro-2-propyl, Heptafluoro-2-propyl, 1-Chloropropyl, 2-Chloropropyl, 3-Chloropropyl, 1,1-Dichloropropyl, 2,2-Dichloropropyl, 3,3-Dichloropropyl, 3,3,3-Trichloropropyl, 2,2,3,3,3-Pentachloropropyl, Heptachloropropyl, 1-Chloro-2-propyl, 2-Chloro-2-propyl, 1,1-Dichloro-2-propyl, 1,2-Dichloro-2-propyl, 1,3-Dichloro-2-propyl, 1,2,3-Trichloro-2-propyl, 1,1,3,3-tetrachloro-2-propyl, 1,1,1,3,3,3-hexachloro-2-propyl, heptachloro-2-propyl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromo-2-propyl, 2-bromo-2-propyl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodo-2-propyl, 2-iodo-2-propyl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, 4,4,4-trifluoro- 3-methylbutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluoro-2-butyl, 4,4,4-trifluoro-2-butyl, 3,3,4,4,4-pentafluoro-2-butyl, nonafluoro-2-butyl, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propyl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichlorobutyl 4,4,4-trichlorobutyl, nonachlorobutyl, 1,1,1-trichloro-2-butyl, 4,4,4-trichloro-2-butyl, nonachloro-2-butyl, 1-bromobutyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluorinated Lopentyl, 5-fluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4,4,5,5-octafluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5-trichloropentyl, 4,4,5,5,5-pentachloropentyl, 3,3,4,4,5,5,5-Heptachloropentyl, 2,2,3,3,4,4,5,5,5-Nonachloropentyl, Undecachloropentyl, 1-Bromopentyl, 2-Bromopentyl, 3-Bromopentyl, 4-Bromopentyl, 5-Bromopentyl, 5-Iodopentyl, 1-Fluorohexyl, 2-Fluorohexyl, 3-Fluorohexyl, 4-Fluorohexyl, 5-Fluorohexyl, 6-Fluorohexyl, 6,6,6-Trifluorohexyl, 5,5,6,6,6-Pentafluorohexyl, 4,4,5,5,6,6,6-Heptachloropentyl Examples of groups include ptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl, 2,2,3,3,4,4,5,5,6,6-decafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, 5-iodohexyl, or 6-iodohexyl.

[0016] In the present invention, unless otherwise specified, "C1-C6 alkoxy group" refers to a (C1-C6 alkyl)-O- group in which the alkyl portion has the meaning described above. Examples of such groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, or n-hexyloxy.

[0017] In the present invention, unless otherwise specified, "C1-C6 alkylthio C1-C6 alkyl" refers to a (C1-C6 alkyl)-S-(C1-C6 alkyl)-group where the alkyl portion has the meaning described above, for example, methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, 1-(methylthio)ethyl, 2-(methylthio)ethyl, 2-(ethylthio)ethyl, 1-(n-propylthio)ethyl, 2-(n-propylthio)ethyl, 1-(isopropylthio)ethyl, 2-(isopropylthio)ethyl, 1-(methylthio)propyl, 2-(methylthio)propyl, 3-(methylthio)propyl, 1-(ethylthio)propyl, 2-( Examples of groups include ethylthio)propyl, 3-(ethylthio)propyl, 1-(n-propylthio)propyl, 2-(n-propylthio)propyl, 3-(n-propylthio)propyl, 1-(methylthio)butyl, 2-(methylthio)butyl, 3-(methylthio)butyl, 4-(methylthio)butyl, 1-(methylthio)pentyl, 2-(methylthio)pentyl, 3-(methylthio)pentyl, 4-(methylthio)pentyl, 5-(methylthio)pentyl, 2-(n-butylthio)ethyl, 2-(isobutylthio)ethyl, 2-(sec-butylthio)ethyl, 2-(tert-butylthio)ethyl, pentylthiomethyl, or hexylthiomethyl.

[0018] In the present invention, "C1-C6 alkylsulfinyl C1-C6 alkyl" means, unless otherwise specified, that the alkyl portion represents a (C1-C6 alkyl)-S(=O)-(C1-C6 alkyl)- group as described above. Examples include methylsulfinylmethyl, ethylsulfinylmethyl, n-propylsulfinylmethyl, isopropylsulfinylmethyl, 1-(methylsulfinyl)ethyl, 2-(methylsulfinyl)ethyl, 2-(ethylsulfinyl)ethyl, 1-(n-propylsulfinyl)ethyl, 2-(n-propylsulfinyl)ethyl, 1-(isopropylsulfinyl)ethyl, 2-(isopropylsulfinyl)ethyl, 1-(methylsulfinyl)propyl, 2-(methylsulfinyl)propyl, 3-(methylsulfinyl)propyl, 1-(ethylsulfinyl)propyl, 2-(ethylsulf Examples of groups include phenyl(propyl), 3-(ethylsulfinyl)propyl, 1-(n-propylsulfinyl)propyl, 2-(n-propylsulfinyl)propyl, 3-(n-propylsulfinyl)propyl, 1-(methylsulfinyl)butyl, 2-(methylsulfinyl)butyl, 3-(methylsulfinyl)butyl, 4-(methylsulfinyl)butyl, 1-(methylsulfinyl)pentyl, 2-(methylsulfinyl)pentyl, 3-(methylsulfinyl)pentyl, 4-(methylsulfinyl)pentyl, 5-(methylsulfinyl)pentyl, 2-(n-butylsulfinyl)ethyl, 2-(isobutylsulfinyl)ethyl, 2-(sec-butylsulfinyl)ethyl, 2-(tert-butylsulfinyl)ethyl, pentylsulfinylmethyl, or hexylsulfinylmethyl.

[0019] In the present invention, unless otherwise specified, "C1-C6 alkylsulfonyl C1-C6 alkyl" refers to a (C1-C6 alkyl)-S(=O)2-(C1-C6 alkyl)-group in which the alkyl portion has the meaning described above. Examples include methylsulfonylmethyl, ethylsulfonylmethyl, n-propylsulfonylmethyl, isopropylsulfonylmethyl, 1-(methylsulfonyl)ethyl, 2-(methylsulfonyl)ethyl, 2-(ethylsulfonyl)ethyl, 1-(n-propylsulfonyl)ethyl, 2-(n-propylsulfonyl)ethyl, 1-(isopropylsulfonyl)ethyl, 2-(isopropylsulfonyl)ethyl, 1-(methylsulfonyl)propyl, 2-(methylsulfonyl)propyl, 3-(methylsulfonyl)propyl, 1-(ethylsulfonyl)propyl, 2-(ethyl Examples of groups include sulfonyl)propyl, 3-(ethylsulfonyl)propyl, 1-(n-propylsulfonyl)propyl, 2-(n-propylsulfonyl)propyl, 3-(n-propylsulfonyl)propyl, 1-(methylsulfonyl)butyl, 2-(methylsulfonyl)butyl, 3-(methylsulfonyl)butyl, 4-(methylsulfonyl)butyl, 1-(methylsulfonyl)pentyl, 2-(methylsulfonyl)pentyl, 3-(methylsulfonyl)pentyl, 4-(methylsulfonyl)pentyl, 5-(methylsulfonyl)pentyl, 2-(n-butylsulfonyl)ethyl, 2-(isobutylsulfonyl)ethyl, 2-(sec-butylsulfonyl)ethyl, 2-(tert-butylsulfonyl)ethyl, pentylsulfonylmethyl, or hexylsulfonylmethyl.

[0020] In the present invention, unless otherwise specified, "cyano C1-C6 alkyl group" refers to a (cyano)-(C1-C6 alkyl)-group in which the alkyl portion has the meaning described above. Examples of such groups include cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyano-2-propyl, 1-cyano-2-methylpropyl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl, or 6-cyanohexyl.

[0021] In the present invention, unless otherwise specified, "C1-C6 alkoxy C1-C6 alkyl group" refers to a (C1-C6 alkyl)-O-(C1-C6 alkyl)-group where the alkyl portion has the meaning described above. Examples of such groups include methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-ethoxypropyl, 3-ethoxypropyl, 1-methyl-3-methoxybutyl, or 3-butoxybutyl.

[0022] In the present invention, unless otherwise specified, "C1-C6 haloalkoxy C1-C6 alkyl group" refers to a (C1-C6 haloalkyl)-O-(C1-C6 alkyl)-group where the haloalkyl portion and alkyl portion have the meanings described above, for example, 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethoxy)ethyl, 2-(2,2,2-trifluoroethoxy)ethyl, 2-(3,3-difluoropropiooxy)ethyl, 2 Examples of groups include -(3,3,3-trifluoropropioxy)ethyl, 3-(difluoromethoxy)propyl, 3-(trifluoromethoxy)propyl, 3-(2,2-difluoroethoxy)propyl, 3-(2,2,2-trifluoroethoxy)propyl, 3-(3,3-difluoropropioxy)propyl, 3-(3,3,3-trifluoropropioxy)propyl, 4-(trifluoromethoxy)butyl, or 5-(trifluoromethoxy)pentyl.

[0023] In the present invention, "C3-C6 cycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms unless otherwise specified, and the ring may be optionally substituted with an alkyl group within a specified range of carbon atoms. Examples include groups such as cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, or cyclohexyl.

[0024] In the present invention, "C3-C6 halocycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms that is substituted with the same or different 1 to 11 halogen atoms, unless otherwise specified, and the ring may be optionally substituted with an alkyl group or haloalkyl group within a specified range of carbon atoms. For example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 1-bromocyclopropyl, 2,2-dibromocyclopropyl, 1-iodocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-diiodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclo Lopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl, 2,2-dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclo Examples of groups include hexyl, 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3,3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4-dibromocyclohexyl, 3,3-diiodocyclohexyl, or 4,4-diiodocyclohexyl.

[0025] In the present invention, "C3-C6 cycloalkyl C1-C6 alkyl" refers to a (C3-C6 cycloalkyl)-(C1-C6 alkyl)-group where the cycloalkyl portion and the alkyl portion have the meanings described above, unless otherwise specified. Examples of such groups include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-(cyclopropyl)ethyl, 2-(cyclopropyl)ethyl, or 1-(cyclopropyl)propyl.

[0026] In the present invention, unless otherwise specified, "C1-C6 haloalkyl C3-C8 cycloalkyl" means the haloalkyl portion and the cycloalkyl portion as described above, and refers to a (C1-C6 haloalkyl)-(C3-C8 cycloalkyl)-group in which a haloalkyl group is substituted on the cycloalkyl portion. Examples of such groups include 1-difluoromethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-(2,2,2-trifluoroethyl)cyclopropyl, 2-trifluoromethylcyclopropyl, 1-difluoromethylcyclobutyl, 1-trifluoromethylcyclobutyl, 1-difluoromethylcyclopentyl, 1-trifluoromethylcyclopentyl, 1-difluoromethylcyclohexyl, 1-trifluoromethylcyclohexyl, 4-(difluoromethyl)cyclohexyl, or 4-(trifluoromethyl)cyclohexyl.

[0027] In the present invention, unless otherwise specified, "C1-C6 alkylamino group" refers to a (C1-C6 alkyl)-NH- group in which the alkyl portion has the meaning described above, and examples include groups such as methylamino, ethylamino, n-propylamino, or isopropylamino.

[0028] In this invention, "phenyloxy group" refers to a (phenyl)-O- group.

[0029] In the present invention, unless otherwise specified, "C1-C6 alkylcarbonyl group" refers to a (C1-C6 alkyl)-C(=O)- group where the alkyl portion has the meaning described above. Examples of such groups include acetyl, propionyl, 2-methylpropionyl, 2,2-dimethylpropionyl, butanoyl, pivaloyl, 2-methylbutanoyl, 3-methylbutanoyl, 2-ethylbutanoyl, 2,2-dimethylbutanoyl, 2,3-dimethylbutanoyl, 3,3-dimethylbutanoyl, pentanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl, or hexanoyl.

[0030] In the present invention, unless otherwise specified, "C1-C6 alkoxycarbonyl group" refers to a (C1-C6 alkyl)-OC(=O)- group where the alkyl portion has the meaning described above. Examples of such groups include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, or 2,2-dimethylpropoxycarbonyl.

[0031] In the present invention, unless otherwise specified, "C1-C6 alkylcarbonyloxy C1-C6 alkyl group" refers to a (C1-C6 alkyl)-C(=O)-O-(C1-C6 alkyl)-group where the alkyl portion has the meaning described above. Examples of such groups include acetoxymethyl, propionyloxymethyl, isobutyryloxymethyl, or pivaloyloxymethyl.

[0032] In the present invention, unless otherwise specified, "C1-C6 alkoxycarbonyloxy C1-C6 alkyl group" refers to a (C1-C6 alkyl)-OC(=O)-O-(C1-C6 alkyl)-group where the alkyl portion has the meaning described above. Examples of such groups include methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, isopropoxycarbonyloxymethyl, tert-butoxycarbonyloxymethyl, or isobutoxycarbonyloxymethyl.

[0033] In the present invention, unless otherwise specified, "C3-C6 cycloalkylcarbonyl group" refers to a (C3-C6 cycloalkyl)-C(=O)- group in which the cycloalkyl portion has the meaning described above. Examples include cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, or cyclohexanecarbonyl groups.

[0034] In the present invention, a salt, or an agriculturally permissible salt, is a compound of the present invention represented by general formula [I] in which a hydroxyl group, carboxyl group, amino group, etc., is present in its structure, or the nitrogen atom of the pyridine ring is salted with a metal or organic base, or a mineral acid or organic acid. Examples of metals include alkali metals such as sodium or potassium, or alkaline earth metals such as magnesium or calcium. Examples of organic bases include triethylamine or diisopropylamine. Examples of mineral acids include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, or sulfuric acid. Examples of organic acids include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid, or trifluoromethanesulfonic acid.

[0035] Next, Tables 1 to 33 show representative examples of compounds included in the compound of the present invention represented by general formula [I]. However, the compounds included in the derivative of the present invention are not limited to these. Also, the compound numbers in the tables will be referenced in the following description.

[0036] Furthermore, while the compounds included in the present invention, represented by general formula [I], may have geometric isomers of E- and Z-forms depending on the type of substituent, the present invention encompasses these E-forms, Z-forms, or mixtures containing E- and Z-forms in any proportion. In addition, while the compounds included in the present invention may have optical isomers due to the presence of one or more chiral carbon atoms and chiral sulfur atoms, the present invention encompasses all optically active compounds, racemates, or diastereomers.

[0037] In the tables used herein, the following notations represent the corresponding groups, for example, as shown below. NO2: Nitro; Me: methyl; Et: ethyl; n-Pr: n-propyl; i-Pr: Isopropyl; n-Bu: n-butyl; i-Bu: Isobutyl; t-Bu: tert-butyl; c-Pr: Cyclopropyl; c-Pr(1-F) :1-fluorocyclopropyl; c-Bu: Cyclobutyl; c-Pentyl: Cyclopentyl; CHF2: Difluoromethyl; CF3: Trifluoromethyl; CH2CF3:2,2,2-trifluoroethyl; OCH3: Methoxy; CH2OCH3: Methoxymethyl; CH2SCH3: Methylthiomethyl; CH2S(=O)CH3: Methylsulfinylmethyl; CH2S(=O)2CH3: Methylsulfonylmethyl; C(=O)(i-Pr): 2-methylpropionyl; C(=O)(c-Pr): Cyclopropylcarbonyl; C(=O)OCH3: Methoxycarbonyl; CH2OC(=O)OCH3: Methoxycarbonyloxymethyl; CH2OC(=O)(t-Bu): tert-butylcarbonyloxymethyl; OPh(4-NO2): (4-nitrophenyl)oxy;

[0038] [Table 1]

[0039] [Table 2]

[0040] [Table 3]

[0041] [Table 4]

[0042] [Table 5]

[0043] [Table 6]

[0044] [Table 7]

[0045] [Table 8]

[0046] Table 9

[0047] Table 10

[0048] Table 11

[0049] Table 12

[0050] Table 13

[0051] Table 14

[0052] Table 15

[0053] Table 16

[0054] Table 17

[0055] Table 18

[0056] Table 19

[0057] Table 20

[0058] Table 21

[0059] Table 22

[0060] Table 23

[0061] Table 24

[0062] Table 25

[0063] Table 26

[0064] Table 27

[0065] Table 28

[0066] [Table 29]

[0067] [Table 30]

[0068] [Table 31]

[0069] [Table 32]

[0070] [Table 33]

[0071] On the other hand, the compound of the present invention represented by general formula [I] can be produced according to the following manufacturing methods, but is not limited to these methods. Hereinafter, for example, "compound represented by general formula [I]", "compound represented by formula [I]", and "compound [I]" are considered synonymous. <Manufacturing method 1> The compound represented by general formula [III] can be produced using the compound represented by general formula [II] according to a method consisting of the reaction shown below. [ka] (In the formula, R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by general formula [III] can be produced by reacting compound [II] in a suitable solvent in the presence of sodium chlorite, sodium dihydrogen phosphate and 2-methyl-2-butene, according to Pinnick oxidation conditions, for example, the method described in Bioorg. Med. Chem. Lett., Vol. 28 (Nos. 23-24), pp. 3708-3711 (2018).

[0072] <Production Method 2> The compound represented by General Formula [IV] can be produced according to the method consisting of the reaction formula exemplified below using the compound represented by General Formula [III].

Chemical Formula

[0073] <Production Method 3> The compound represented by General Formula [V] can be produced according to the method consisting of the reaction formula exemplified below using the compound represented by General Formula [IV].

Chemical Formula

[0074] <Manufacturing method 4> The compound represented by general formula [VII] can be produced using the compound represented by general formula [V] according to a method consisting of the reaction shown below. [ka] (In the formula, R 3 , R 4 and R 7 (This has the same meaning as above.) That is, the compound represented by general formula [VII] can be produced by reacting compound [V] and compound [VI] in a suitable solvent in the presence of a suitable trisubstituted phosphine and a suitable azodicarboxylic acid derivative. The amount of compound [VI] used in this reaction can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [V], and preferably 1.0 to 3.0 moles. Examples of tri-substituted phosphines that can be used in this reaction include triphenylphosphine, tributylphosphine, and trimethylphosphine. The amount of tri-substituted phosphine used can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [V], and preferably 1.0 to 3.0 moles. Examples of azodicarboxylic acid derivatives that can be used in this reaction include diethyl azodicarboxylic acid, diisopropyl azodicarboxylic acid, dimethoxyethyl azodicarboxylic acid, and N,N,N',N'-tetramethylazodicarboxylic acid amide. The amount of azodicarboxylic acid derivative used can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [V], and preferably 1.0 to 3.0 moles. Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglycerides, and diglymes; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; or mixed solvents thereof. The amount of solvent used is 0.1 to 100 liters per mole of compound [V], preferably 0.3 to 10 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -5°C to 100°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [VII] can be isolated by concentrating the reaction mixture as is, or by adding it to water or another solvent, extracting it with an organic solvent, and then concentrating it. The isolated compound [VII] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0075] <Manufacturing method 5> A compound represented by general formula [VIII] or a salt thereof can be produced using a compound represented by general formula [VII] according to a method consisting of the reaction shown below. [ka] (In the formula, R 3 , R 4 and R 7 (This has the same meaning as above.) That is, the compound represented by general formula [VIII] or a salt thereof can be prepared by reacting compound [VII] in a suitable solvent in the presence of a suitable acid, according to the conditions used for deprotection of the tert-butoxycarbonyl group, for example, according to the method described in GREENE'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter GMWuts).

[0076] <Manufacturing method 6> The compound represented by general formula [X] can be produced by a method consisting of the reaction shown below, using the compound represented by general formula [VIII] or a salt thereof. [ka] (In the formula, L 1R represents a halogen atom or a trifluoromethanesulfonyloxy group. 3 , R 4 , R 6 and R 7 (This has the same meaning as above.) That is, the compound represented by general formula [X] can be produced by reacting compound [VIII] or a salt thereof with compound [IX] in a suitable solvent in the presence of a suitable base. The amount of compound [IX] used in this reaction can be appropriately selected from the range of 1.0 to 10 moles per mole of compound [VIII], and preferably 1.0 to 6.0 moles. Examples of bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; alkali metal fluorides such as sodium fluoride and potassium fluoride; alkali metal phosphates such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkyllithiums such as methyllithium, butyllithium, and phenyllithium; or organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of base used can be appropriately selected from the range of 1.0 to 12 moles per mole of compound [VIII], and preferably 1.0 to 6.0 moles. Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglycerides, and diglymes; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; or mixed solvents thereof. The amount of solvent used is 0.1 to 100 liters per mole of compound [VIII], preferably 0.3 to 15 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -100°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -60°C to 50°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [X] can be isolated by either concentrating the reaction mixture as is, or by adding it to water, extracting it with an organic solvent, and then concentrating it. The isolated compound [X] can be further purified by column chromatography, recrystallization, etc., as needed.

[0077] <Manufacturing method 7> The compound represented by general formula [XI] can be produced using the compound represented by general formula [X] according to a method consisting of the reaction equation exemplified below. [ka] (In the formula, R 3 , R 4 , R 6 and R 7 (This has the same meaning as above.) That is, the compound represented by general formula [XI] can be produced by hydrolyzing the compound represented by general formula [X] in a suitable solvent in the presence of a suitable acid or base. Examples of acids that can be used in this reaction include those similar to those used in production method 3 described above. The amount of acid used can be appropriately selected from a range of 1 to the amount of solvent per mole of compound [X], and is preferably 1.0 to 100 moles. Examples of bases that can be used in this reaction include those used in the same production method 6 described above. The amount of base used can be appropriately selected from the range of 0.1 to 50 moles per mole of compound [X], and preferably 0.5 to 20 moles. Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglycerides, and diglymes; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; and N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and sulfolamide. Examples of solvents include aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; or mixed solvents thereof. The amount of solvent used is 0.1 to 500 liters per mole of compound [X], preferably 0.3 to 30 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of 0°C to 100°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, the reaction mixture is neutralized by adding it to water, and the precipitated solid can be isolated by filtering or extracting it with an organic solvent and then concentrating it. The isolated compound [XI] can be further purified by column chromatography, recrystallization, etc., as needed.

[0078] <Manufacturing method 8> The compound represented by general formula [XIII] can be produced using the compound represented by general formula [XI] according to a method consisting of the reaction equation exemplified below. [ka] (In the formula, L 2 R represents a halogen atom, a p-toluenesulfonyloxy group, a methanesulfonyloxy group, or a trifluoromethanesulfonyloxy group. 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) That is, the compound represented by general formula [XIII] can be produced by reacting compound [XI] and compound [XII] in a suitable solvent in the presence of a suitable base. The amount of compound [XII] used in this reaction can be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XI], and preferably 1.0 to 5.0 moles. Examples of bases that can be used in this reaction include those used in the same production method 6 described above. The amount of base used can be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XI], and preferably 1.0 to 5.0 moles. Suitable solvents for this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglycerides, and diglymes; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; and esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate. Examples of solvents include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; or mixed solvents thereof. The amount of solvent used is 0.1 to 100 liters per mole of compound [XI], preferably 0.3 to 15 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -10°C to 80°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [XIII] can be isolated by concentrating the reaction mixture as is, or by adding it to water and filtering the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [XIII] can be further purified by column chromatography, recrystallization, etc., as needed.

[0079] <Manufacturing method 9> The compound represented by general formula [XIV] can be produced using the compound represented by general formula [XIII] according to a method consisting of the reaction shown below. [ka] (In the formula, R 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) That is, the compound represented by general formula [XIV] can be produced by reacting compound [XIII] in a suitable solvent in the presence of a suitable reducing agent. Examples of reducing agents that can be used in this reaction include lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, lithium borohydride, and sodium borohydride. The amount of reducing agent used can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [XIII], and preferably 1.0 to 3.0 moles. Examples of solvents that can be used in this reaction include those used in the same production method 7 described above. The amount of solvent used is 0.1 to 500 liters per mole of compound [XIII], preferably 0.3 to 30 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -10°C to 100°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [XIV] can be isolated by adding the reaction mixture to water or another solvent, filtering the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [XIV] can be further purified by column chromatography, recrystallization, etc., as needed.

[0080] <Manufacturing method 10> The compound represented by general formula [XV] can be produced using the compound represented by general formula [XIV] according to a method consisting of the reaction equation exemplified below. [ka] (In the formula, L 3 R indicates a halogen atom. 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) That is, the compound represented by general formula [XV] can be produced by reacting compound [XIV] in a suitable solvent, in the presence of a suitable trisubstituted phosphine and a suitable halogen compound, and in the presence or absence of a suitable additive. Examples of tri-substituted phosphines that can be used in this reaction include triphenylphosphine, tributylphosphine, and trimethylphosphine. The amount of tri-substituted phosphine used can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [XIV], and preferably 1.0 to 3.0 moles. Examples of halogen compounds used in this reaction include carbon tetrachloride, carbon tetrabromide, and iodine. The amount of halogen compound used can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [XIV], and preferably 1.0 to 3.0 moles. Examples of additives that can be used in this reaction include imidazole and pyridine. The amount of additive used should be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [XIV], and preferably 1.0 to 3.0 moles. Examples of solvents that can be used in this reaction include those similar to those used in production method 4 described above. The amount of solvent used is 0.1 to 100 liters per mole of compound [XIV], preferably 0.3 to 20 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -10°C to 100°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [XV] can be isolated by either concentrating the reaction mixture as is, or by adding it to water and extracting it with an organic solvent before concentrating it. The isolated compound [XV] can be further purified by column chromatography, recrystallization, etc., as needed.

[0081] <Manufacturing method 11> The compound represented by general formula [XVII] can be produced using the compound represented by general formula [XV] according to a method consisting of the reaction shown below. [ka] (In the formula, L 3 , R 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) That is, the compound represented by the general formula [XVII] can be produced by reacting compound [XV] and compound [XVI] in a suitable solvent in the presence of a suitable base. The amount of compound [XVI] used in this reaction can be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XV], and preferably 1.0 to 5.0 moles. Examples of bases that can be used in this reaction include those used in the same production method 6 described above. The amount of base used can be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XV], and preferably 1.0 to 5.0 moles. Examples of solvents that can be used in this reaction include those used in the same production method 8 described above. The amount of solvent used is 0.1 to 100 liters per mole of compound [XV], preferably 0.3 to 15 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of 0°C to 100°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 120 hours. After the reaction is complete, compound [XVII] can be isolated by adding the reaction mixture to water or another solvent, extracting it with an organic solvent, and then concentrating the mixture. The isolated compound [XVII] can be further purified by column chromatography, recrystallization, or other methods as needed.

[0082] <Manufacturing method 12> A compound represented by general formula [XVIII] or a salt thereof can be produced using a compound represented by general formula [XVII] according to a method consisting of the reaction shown below. [ka] (In the formula, R 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) That is, the compound represented by general formula [XVIII] or a salt thereof can be prepared by reacting compound [XVII] in a suitable solvent in the presence of a suitable acid, according to the conditions used for deprotection of the tert-butoxycarbonyl group, for example, according to the method described in GREENE'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter GMWuts).

[0083] <Manufacturing method 13> Among the compounds of the present invention, the compound represented by general formula [I-1] can be produced by using the compound represented by general formula [XVIII] according to a method consisting of the reaction shown below. [ka] (In the formula, L 3 , R 1 , R 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) That is, the compound of the present invention represented by general formula [I-1] can be produced by reacting compound [XVIII] with compound [XIX] or compound [XX] in a suitable solvent, in the presence or absence of a suitable condensing agent and a suitable additive, in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base. The amount of compound [XIX] or compound [XX] used in this reaction can be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XVIII], preferably 1.0 to 5.0 moles. When using a condensing agent in this reaction, suitable condensing agents include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. Examples of condensing agents include 1H-benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, ({[(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy}-4-morpholinomethylene)dimethylammonium hexafluorophosphate, O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, and propylphosphonic anhydride. The amount of condensing agent used should be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XVIII], and preferably 1.0 to 5.0 moles. When additives are used in this reaction, examples of suitable additives include 1-hydroxybenzotriazole, N-hydroxysuccinimide, and 1-hydroxy-7-azabenzotriazole. The amount of additive used should be appropriately selected from 0.01 to 3.0 moles per mole of compound [XVIII], and preferably 1.0 to 1.5 moles. When a catalyst is used in this reaction, examples of suitable catalysts include 4-N,N-dimethylaminopyridine. The amount of catalyst used should be appropriately selected from the range of 0.001 to 1.0 moles per mole of compound [XVIII], and preferably 0.01 to 0.1 moles. When a base is used in this reaction, suitable bases include those similar to those used in production method 6 described above. The amount of base used should be appropriately selected from the range of 1.0 to 10 moles per mole of compound [XVIII], and preferably 1.0 to 5.0 moles. Examples of solvents that can be used in this reaction include those used in the same production method 8 described above. The amount of solvent used is 0.1 to 100 liters per mole of compound [XVIII], preferably 0.3 to 50 liters. The reaction temperature for this reaction can be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -10°C to 80°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 96 hours. After the reaction is complete, compound [I-1] can be isolated by adding the reaction mixture to water or another solvent, filtering out the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, or other methods as needed.

[0084] <Manufacturing method 14> Among the compounds of the present invention, the compound represented by general formula [I-2] can be produced using the compound represented by general formula [I-1] according to a method consisting of the reaction shown below. [ka] (In the formula, R 1 , R 3 , R 4 , R 5 and R 6 (This has the same meaning as above.) In other words, the compound of the present invention represented by general formula [I-2] can be produced by reacting compound [I-1] in a suitable solvent in the presence of a suitable acid. Examples of acids that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid; and Lewis acids such as aluminum chloride, boron tribromide, and titanium(IV) chloride. The amount of acid used should be appropriately selected from a range of 1 to the amount of solvent per mole of compound [I-1], preferably 1.0 to 20 moles. Examples of solvents that can be used in this reaction include those used in the same production method 7 described above. The amount of solvent used is 0.1 to 500 liters per mole of compound [I-1], preferably 0.3 to 60 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of -10°C to 100°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [I-2] can be isolated by adding the reaction mixture to water or another solvent, filtering out the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [I-2] can be further purified by column chromatography, recrystallization, or other methods as needed.

[0085] <Manufacturing method 15> The compound represented by general formula [XXI] can be produced using the compound represented by general formula [X] according to a method consisting of the reaction equation exemplified below. [ka] (In the formula, L 2 , R 3 , R 4 , R 5 , R 6 and R 7(This has the same meaning as above.) That is, the compound represented by general formula [XXI] can be produced by reacting compound [X] and compound [XII] in a suitable solvent in the presence of a suitable base. The compound [XII], base, solvent, reaction temperature, and reaction time used in this reaction are the same as those in production method 8 described above. After the reaction is complete, compound [XXI] can be isolated by concentrating the reaction mixture as is, or by adding it to water and filtering the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [XXI] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0086] <Manufacturing method 16> The compound represented by general formula [XXIII] can be produced using the compound represented by general formula [XXII] according to a method consisting of the reaction shown below. [ka] (In the formula, L 3 , R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by general formula [XXIII] can be produced by reacting compound [XXII] and compound [XVI] in a suitable solvent in the presence of a suitable base. The compound [XVI], base, solvent, reaction temperature, and reaction time used in this reaction are the same as those in the production method 11 described above. After the reaction is complete, compound [XXIII] can be isolated by adding the reaction mixture to water or another solvent, extracting it with an organic solvent, and then concentrating the mixture. The isolated compound [XXIII] can be further purified by column chromatography, recrystallization, or other methods as needed. <Manufacturing method 17> A compound represented by general formula [XXIV] or a salt thereof can be produced using a compound represented by general formula [XXIII] according to a method consisting of the reaction shown below. [ka] (In the formula, L 3 , R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by general formula [XXIV] or a salt thereof can be prepared by reacting compound [XXIII] in a suitable solvent in the presence of a suitable acid, according to the conditions used for deprotection of the tert-butoxycarbonyl group, for example, according to the method described in GREENE'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter GMWuts).

[0087] <Manufacturing method 18> Compounds represented by general formula [XXV] can be produced using compounds represented by general formula [XXIV] according to a method consisting of the reaction shown below. [ka] (In the formula, L 3 , R 1 , R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by the general formula [XXV] can be produced by reacting compound [XXIV] with compound [XIX] or compound [XX] in a suitable solvent, in the presence or absence of a suitable condensing agent and a suitable additive, in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base. The compound [XIX] or compound [XX] used in this reaction, the condensing agent, additives, catalyst, base, solvent, reaction temperature, and reaction time are the same as those in the above-described manufacturing method 13. After the reaction is complete, compound [XXV] can be isolated by adding the reaction mixture to water, filtering the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [XXV] can be further purified by column chromatography, recrystallization, etc., as needed.

[0088] <Manufacturing method 19> The compound represented by general formula [XXVII] can be produced using the compound represented by general formula [XXV] according to a method consisting of the reaction equation exemplified below. [ka] (In the formula, L 3 , R 1 , R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by the general formula [XXVII] can be produced by reacting compound [XXV] and compound [XXVI] in a suitable solvent, in the presence of a suitable catalyst, and in the presence of a suitable base. The amount of compound [XXVI] used in this reaction can be appropriately selected from the range of 1.0 to 5.0 moles per mole of compound [XXV], and preferably 1.0 to 3.0 moles. The catalyst that can be used in this reaction may be a combination of a transition metal complex or a transition metal salt and a ligand. For example, the transition metal complex may be tetrakis(triphenylphosphine)palladium, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, or tris(dibenzylideneacetone)dipalladium(O). The transition metal salt may be palladium chloride, palladium bromide, palladium acetate, etc. The ligand may be trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphinopropane, etc. The amount of catalyst used is 0.001 to 0.2 moles per mole of compound [XXV], preferably 0.01 to 0.1 moles. Examples of bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; alkali metal fluorides such as sodium fluoride and potassium fluoride; alkali metal phosphates such as tripotassium phosphate; or organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of base used is 0.1 to 10.0 moles per mole of compound [XXV], preferably 0.1 to 5.0 moles. However, in the case of organic bases, they can also be used as solvents. Suitable solvents for this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglycerides, and diglymes; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; and N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide. Examples include aprotic polar solvents such as sides, sulfolanes, and 1,3-dimethyl-2-imidazolidinone; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; or mixed solvents thereof. The amount of solvent used is 0.1 to 500 liters per mole of compound [XXV], preferably 0.3 to 30 liters. The reaction temperature for this reaction can usually be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably carried out in the range of 0°C to 150°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [XXVII] can be isolated by concentrating the reaction mixture as is, or by adding it to water and filtering the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [XXVII] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0089] <Manufacturing method 20> The compound represented by general formula [XXVIII] can be produced using the compound represented by general formula [XXVII] according to a method consisting of the reaction shown below. [ka] (In the formula, R 1 , R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by the general formula [XXVIII] can be produced by reacting compound [XXVII] with a suitable oxidizing agent in a suitable solvent. Examples of oxidizing agents that can be used in this reaction include hydrogen peroxide, sodium perborate tetrahydrate, and 4-methylmorpholine-N-oxide. The amount of oxidizing agent used should be appropriately selected from the range of 1.0 to 20.0 moles per mole of compound [XXVII], and preferably 1.0 to 5.0 moles. Suitable solvents for this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglycerides, and diglymes; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; and N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide. Examples of solvents include aprotic polar solvents such as sulfolane and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water; or mixed solvents thereof. The amount of solvent used is 0.1 to 500 liters per mole of compound [XXVII], preferably 0.3 to 30 liters. The reaction temperature for this reaction can be selected from any temperature range from 0°C to the reflux temperature of the reaction system, and is preferably carried out in the range of room temperature to 120°C. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually between 1 minute and 72 hours. After the reaction is complete, compound [XXVIII] can be isolated by concentrating the reaction mixture as is, or by adding it to water and filtering the precipitated solid, or by extracting it with an organic solvent and then concentrating it. The isolated compound [XXVIII] can be further purified by column chromatography, recrystallization, etc., as needed.

[0090] <Manufacturing method 21> The compound represented by general formula [XXIX] can be produced using the compound represented by general formula [XXVIII] according to a method consisting of the reaction shown below. [ka] (In the formula, R 1 , R 3 and R 4 (This has the same meaning as above.) That is, the compound represented by general formula [XXIX] can be produced by reacting compound [XXVIII] and compound [VI] in a suitable solvent in the presence of a trisubstituted phosphine and an azodicarboxylic acid derivative. The compound [VI], trisubstituted phosphine, azodicarboxylic acid derivative, solvent, reaction temperature, and reaction time used in this reaction are the same as those in Production Method 4 described above. After the reaction is complete, compound [XXIX] can be isolated by concentrating the reaction mixture as is, or by adding it to water or another solvent, extracting it with an organic solvent, and then concentrating it. The isolated compound [XXIX] can be further purified by column chromatography, recrystallization, etc., as needed.

[0091] <Manufacturing method 22> The compound represented by the general formula [XXX] or a salt thereof can be produced according to the method consisting of the reaction formula exemplified below using the compound represented by the general formula [XXIX].

Chemical formula

[0092] <Production Method 23> Among the compounds of the present invention, the compound represented by the general formula [I-2] can be produced according to the method consisting of the reaction formula exemplified below using the compound represented by the general formula [XXX].

Chemical formula

[0093] <Production Method 24> Among the compounds of the present invention, the compound represented by the general formula [I-3] can be produced according to the method consisting of the reaction formula exemplified below using the compound represented by the general formula [I-1]. [Chemical formula] (In the formula, L 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as described above.) That is, the compound of the present invention represented by the general formula [I-3] can be produced by reacting Compound [I-1] and Compound [XXXI] in a suitable solvent in the presence of a suitable base. The amount of Compound [XXXI] used in this reaction may be appropriately selected from the range of 1.0 to 5.0 moles per 1 mole of Compound [I-1], and preferably 1.0 to 3.0 moles. The base, solvent, reaction temperature, and reaction time used in this reaction are the same as those in Production Method 8 described above. After the completion of this reaction, the reaction mixture can be poured into water or the like, extracted with an organic solvent, and then subjected to operations such as concentration to isolate Compound [I-3]. The isolated Compound [I-3] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0094] The compound represented by the general formula [XVIII] and the compound represented by the general formula [XXX] of the present invention are useful compounds as intermediates in the production of the compound represented by the general formula [I] of the present invention or its agriculturally acceptable salts.

[0095] The pesticidal composition of the present invention contains, as an active ingredient, a compound represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof.

[0096] The pesticidal composition of the present invention can contain, if necessary, an additive component (carrier) commonly used in pesticidal formulations. The pest control agent of the present invention contains, as an active ingredient, a compound represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof. The pest control agent of the present invention is typically an insecticide, acaricide, and nematocide.

[0097] The pest control agent of the present invention can contain, if necessary, an additive component (carrier) commonly used in pesticidal formulations.

[0098] Examples of such additive components include carriers such as solid carriers or liquid carriers, surfactants, binders, tackifiers, thickeners, colorants, spreading agents, adherents, antifreeze agents, anti-caking agents, disintegrants, anti-decomposition agents, etc. Other additives such as preservatives and plant pieces may be used as additive components as necessary. These additive components may be used alone or in combination of two or more.

[0099] Examples of solid carriers include mineral carriers such as pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgite clay, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, synthetic silicate, etc.), titanium dioxide, etc.; vegetable carriers such as wood powder, corn stalk, walnut shell, fruit kernel, sawdust, wood chips, bran, soybean powder, powdered cellulose, starch, dextrin, saccharides, etc.; inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc.; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, urea-aldehyde resin, etc.

[0100] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol derivatives such as propylene glycol ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, and isophorone; ethers such as diethyl ether, 1,4-dioxane, cellosolve, dipropyl ether, and tetrahydrofuran; aliphatic hydrocarbons such as n-paraffin, naphthene, isoparaffin, kerosene, and mineral oil; and toluene and C9-C 10 Examples include aromatic hydrocarbons such as alkylbenzenes, xylenes, solvent naphthas, alkylnaphthalenes, and high-boiling aromatic hydrocarbons; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone; amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, and castor oil, and lower alkyl esters of fatty acids derived from the aforementioned vegetable oils; and water.

[0101] Examples of surfactants include nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styrylphenyl ether, acetylenediol, polyoxyalkylene-added acetylenediol, polyoxyethylene ether-type silicone, ester-type silicone, fluorinated surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; alkyl sulfates, polyoxyethylene Examples of anionic surfactants include: anionic surfactants such as methyl ether sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene styrylphenyl ether sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkylnaphthalene sulfonic acid, fatty acid salt, polycarboxylate salt, N-methyl fatty acid sarcosinate, resin salt, polyoxyethylene alkyl ether phosphate, and polyoxyethylene alkylphenyl ether phosphate; cationic surfactants such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride; and amphoteric surfactants such as betaine-type surfactants such as dialkyldiaminoethyl betaine and alkyldimethylbenzyl betaine, and amino acid-type surfactants such as dialkylaminoethylglycine and alkyldimethylbenzylglycine. Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, acacia gum, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol, polyethylene oxide, and natural phospholipids (e.g., cephalin, lecithin, etc.).

[0102] Examples of thickening agents include water-soluble polymers such as xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, and polysaccharides; inorganic fine powders such as high-purity bentonite and white carbon; and organic fine powders such as organic bentonite.

[0103] Examples of colorants include inorganic pigments such as iron oxide, titanium dioxide, and Prussian blue; and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0104] Examples of expanding agents include silicone-based surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinylpyrrolidone, maleic acid / styrene copolymers, methacrylic acid copolymers, half-esters of polyhydric alcohol polymers and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, polyoxyethylene alkanediols, polyoxyethylene alkynediols, alkynediols, and the like.

[0105] Examples of spreading agents include various surfactants such as sodium dialkylsulfosuccinate, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, and polyoxyethylene fatty acid esters; paraffin, terpenes, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyvinyl alkyl ethers, alkylphenol formalin condensates, and synthetic resin emulsions.

[0106] Examples of antifreeze agents include ethylene glycol, diethylene glycol, propylene glycol, polyhydric alcohols such as glycerin, and so on.

[0107] Examples of anti-caking agents include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, and petroleum resin.

[0108] Examples of disintegrants include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymers of methacrylate esters, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0109] Examples of decomposition inhibitors include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenolic, amine, sulfur, and phosphoric acid-based agents; and ultraviolet absorbers such as salicylic acid-based and benzophenone-based agents.

[0110] Examples of preservatives include potassium sorbate and 1,2-benzothiazole-3(2H)-one.

[0111] Examples of plant materials include sawdust, coconut husks, corn cobs, and tobacco stalks.

[0112] On the other hand, when the above-mentioned additive components are included in the pest control agent of the present invention, the content ratio is usually selected in the range of 5 to 95%, preferably 20 to 90%, for carriers such as solid carriers or liquid carriers, on a mass basis; usually selected in the range of 0.1 to 30%, preferably 0.5 to 10%, for surfactants; and for other additives in the range of 0.1 to 30%, preferably 0.5 to 10%.

[0113] The pest control agent of the present invention can be formulated and used in any dosage form, such as powder, granules, granules, wettable powder, water-soluble powder, wettable granules, tablets, jumbo formulations, emulsions, oils, liquids, flowable formulations, emulsions, microemulsions, sasporumulants, trace sprays, microcapsules, fumigants, aerosols, baits, pastes, etc.

[0114] These formulations can be used as is or diluted to a predetermined concentration with a diluent such as water. Various formulations containing the compound of the present invention or their dilutions can be applied by commonly used application methods, namely, spraying (e.g., spraying, misting, atomizing, powdering, granulation, surface application, box application, etc.), soil application (e.g., mixing, drenching, etc.), surface application (e.g., coating, powdering, covering, etc.), seed treatment (e.g., coating, powdering, etc.), immersion, poison bait, fumigation, etc. It is also possible to mix the active ingredient with feed and feed it to livestock to control the occurrence and growth of harmful insects, especially harmful insects, in their excrement.

[0115] The pest control method of the present invention can be carried out by using the above-described application method with an active ingredient amount of the compound represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof.

[0116] The mixing ratio (mass %) of the active ingredient in the pest control agent of the present invention is appropriately selected as needed. For example, when making powders, powder granules, fine granules, etc., it is preferably selected appropriately from the range of 0.01 to 20%, more preferably 0.05 to 10%. When making granules, etc., it is preferably selected appropriately from the range of 0.1 to 30%, more preferably 0.5 to 20%. When making wettable powders, granule wettable powders, etc., it is preferably selected appropriately from the range of 1 to 70%, more preferably 5 to 50%. When making water-soluble agents, liquid agents, etc., it is preferably selected appropriately from the range of 1 to 95%, more preferably 10 to 80%. When making emulsions, etc., it is preferably selected appropriately from the range of 5 to 90%, more preferably 10 to 80%. When making oil agents, etc., it is preferably selected appropriately from the range of 1 to 50%, more preferably 5 to 30%. When making flowable agents, etc., it is preferably selected appropriately from the range of 5 to 60%, more preferably 10 to 50%. When making emulsion agents, microemulsion agents, suspoemulsion agents, etc., it is preferably selected appropriately from the range of 5 to 70%, more preferably 10 to 60%. When making tablets, bait agents, paste agents, etc., it is preferably selected appropriately from the range of 1 to 80%, more preferably 5 to 50%. When making smoking agents, etc., it is preferably selected appropriately from the range of 0.1 to 50%, more preferably 1 to 30%. When making aerosol agents, etc., it is preferably selected appropriately from the range of 0.05 to 20%, more preferably 0.1 to 10%.

[0117] These formulations are diluted to an appropriate concentration and sprayed, or directly applied.

[0118] When the pest control agent of the present invention is used after being diluted with a diluent, it is generally carried out at an active ingredient concentration of 0.1 to 5000 ppm. The application amount per unit area when using the formulation as it is is 0.1 to 5000 g per hectare as the active ingredient compound, but it is not limited thereto.

[0119] Furthermore, it goes without saying that the pest control agent of the present invention is sufficiently effective even when the compound of the present invention is used alone as the active ingredient. However, it can also be mixed or used in combination with other fertilizers, pesticides, such as insecticides, acaricides, nematicides, synergists, fungicides, antivirals, attractants, herbicides, and plant growth regulators as needed, and in this case, it may exhibit even better effects.

[0120] Next, examples of known insecticides (insecticidal active ingredients), acaricides (acaricidal active ingredients), nematicides (nematicidal active ingredients), and synergistic compounds (synergistic active ingredients) that may be mixed or used in combination are given below.

[0121] Insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, synergistic active ingredients: Acrin, azadirachtin, azamethiphos, acynonapyr, azinphos-ethyl, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, azocyclotin, Abamectin, afidopyropen, afoxolaner, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, allethrin [including d-cis-trans and d-trans forms], isazophos, isamidofos ), isocarbophos, isoxathion, isocycloseram, isofenphos-methyl, isoflualanam, isoprocarb, epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin n) Imicyafos, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, umifoxolaner, esfenvalerate, ethiofencarb, ethion, ethiprole, ethylene dibromide, etoxazole, etofenprox,Ethoprophos, etrimfos, emamectin, emamectin benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos, omethoate, Nuclear polyhedrosis virus, cadusafos, kappa-tefluthrin, kappa-bifenthrin, karanjin, cartap, Granulosis virus Entero virus), coumaphos, cryolite, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordane, chloropicrin, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroprallethrin, entomopoxi virus,Irido virus, cyazypyr, cyanophos, diafenthiuron, diamidaphos, cyantraniliprole, cyetpyrafen, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, Sigma virus (virus), cyclaniliprole, cycloxaprid, dicrotophos, diclofenthion, cyclobutrifluram, cycloprothrin, dichlorvos, dichloromezotiaz, dicofol, dicyclanil, disulfoton, dinotefuran, dinobuton, cyhalodiamide, cyhalothrin [including gamma- and lambda- forms], cyphenothrin [ (1R)-trans-isomer included), cyfluthrin [beta-isomer included], diflubenzuron, cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrin [alpha-isomer, beta-isomer, theta-isomer, zeta-isomer included], cybenzoxasulfyl, dimpropyridaz, dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate (DEP), dimethylvinphos, dimethoate, dimefluthrin,Jasmone, cis-jasmone, jasmonic acid, methyl jasmonate, silafluofen, cyromazine, Steinernema carpocapsae, Steinernema kushidai, Steinernema glacerai glaseri), spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spirobudifen, spiromesifen, sulcofuron-sodium, sulfiflumin, sulfindoflufen, sulfluramid, sulfoxaflor, sulfoxamyl, sulfotep, diazinon, thiacloprid rid), tiapyrachlor, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thionazin, thiofanox, thiometon, tiorantraniliprole, tyclopyrazoflor, tigolaner, tetrachlorantraniliprole, tetrachlorvinphos, tetradifon, tetraniliprole,Tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralomethrin, transfluthrin, trizamate, triazophos, trioxyflanilide, trichlorfon, Trichoderma asperellum, Trichoderma paechylomyces Paecilomyces, Trichoderma harzianum, Triflumuron, Trifluenfuronate, Triflumezopyrim, Trimethacarb, Tolfenpyrad, Nald, Nicotine, Nicofluprole, Nitenpyram, Nemadectin, Denso virus, Novaluron, Noviflumuron, Paecilomyces lilacinus, Burkholderia cepacia, Burkholderia rinojensis, Verticillium Verticillium lecanii, hydroprene, Pasteuria nishizawae,Pasteuria penetrans, Bacillus amyloliquefaciens, Bacillus firmus, Bacillus sphericus Bacillus sphaericus), Bacillus subtillis, Bacillus thuringiensis, insect toxins produced by Bacillus thuringiensis, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Israelensis, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis, Bacillus popilliae, Bacillus licheniformis (licheniformis), vadescana, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bioallethrin, bioallethrin S-cyclopentenyl S-cyclopentenyl), pioxaniliprole, bioresmethrin, bis-(2-chloro-1-methylethyl) ether (DCIP), bistrifluron, bisulflufen, hydramethylnon, vinylfluthrin, bifenazate, bifenthrin, pyflubumide, piperflanilide, piperonyl butoxide (piperonyl(butoxide), pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrine, famphur, f Fipronil, fenazaquin, fenamiphos, fenargimine, fenitrothion, fenoxycarb, fenothiocarb, phenothrin [including (1R)-trans-isomer], fenobucarb, fentiazoluron, fenthion, phenthoate, fenvalerate, fenpyroximate, fenbutatin oxide, fenpropathrin, fenmezoditiaz, fonofos, sulfuryl fluorideFluoride), butocarboxim, butoxycarboxim, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazuron, fluensulfone, fluopyram, sodium fluoroacetateFluoracetate), fluxametamide, fluchlordiniliprole, flucycloxuron, flucythrinate, flusulfamide, fluthrin, fluvalinate [including tau-isomer], flupymezotiaz, flupyradifurone, flupyrazofos, flupyrimin, flupyroxystrobin, flufiprole, flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide (flube ndiamide), flupentiofenox, flumetnicam, flumethrin, fluralaner, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite, prohydrojasmon, profenofos, broflanilide, profluthrin, propetamphos, propoxur, flometoquin, bromopropylate, hexythiazox, hexaflumuron, pekilomyces Pacilimyces tenuipes, Paecilomyces fumosoroceus, Paecilomyces lyraquinasLilacinus), heptafluthrin, heptenophos, permethrin, benclothiaz, benzpyrimoxan, bensultap, benzoximate, bendiocarb, benfuracarb, bentiolumin, Pochonia chlamydosporia, Beauveria tenella, Beauveria bassiana, Beauveria bronniatii brongniartii), phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosmet, polynactins, formetanate, phorate, machine oil, malathion, mivorilaner, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, metamidophos, metam, methiocarb, methidathion, methyl isothiocyanate isothiocyanate), methyl bromide (methylbromide), methoxychlor, methoxyfenozide, methothrin, metofluthrin, methoprene, metolcarb, mevinphos, meperfluthrin, modoflaner, Monacrosporium phymatophagum, monocrotophos, momfluorothrin, Trichoderma harzianum, litlure-A, litlure-B, aluminum phosphide, zinc phosphide Phosphide, hydrogen phosphine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, cytoplasmic polyhedrosis virus embedding, fenbutatin oxide, calcium cyanamidecyanide, organotins, nicotine sulfate, (Z)-11-tetradecenyl acetate, (Z)-11-hexadecenal, (Z)-11-hexadecenyl acetate, (Z)-9,12-tetradecadienyl acetate, (Z)-9-tetradecen-1-ol, (Z,E)-9,11-tetradecadienyl Setate, (Z,E)-9,12-tetradecadienyl acetate, 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT), 1,3-dichloropropene, 4,6-dinitro-o-cresol (DNOC), Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cr (y3Bb,Cry34 / 35Ab1), Methyl eugenol, 4-(p-acetooxyphenyl)-2-butanone, (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-13-icosen-10-one, 14-methyl-1-octadecene, AKD-1193 (code number), BCS-AA1014 7 (code number), CL900167 (code number), O,O-diethyl-O-[4-(dimethylsulfamoyl)phenyl]-phosphorothionate (DSP), O-ethyl-O-4-(nitrophenyl)phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosen-10-one, ZXI8901 (code number), F4260 (code number).

[0122] Next, examples of known herbicides, herbicidal active ingredients, or plant growth regulators that may be mixed or used in combination are given below, but are not limited to these examples.

[0123] Herbicide compounds or herbicidal active ingredients: Ioxynil (including salts with lithium salt, sodium salt, octanonic acid, etc.), acroniphen, acrolein, azaphenidin, acifluorfen (including salts with sodium, etc.), azimsulfuron, asulam, acetochlor, atrazine, anilofos, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, ametryn, Araujia Mosaic Virus, alachlor, Alternaria Alternaria destruens, alloxydim (including salts with sodium, etc.), ancymidol, icafolin-methyl, isouron, isoxachlortole, isoxafenacil, isoxaflutole, isoxaben, isodecyl alcohol ethoxylate, isoprotu ron), ipfencarbazone, iptriazopyrid, imazaquin, imazapic (including salts with amines, etc.), imazapyr (including salts with isopropylamine, etc.), imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron,Indaziflam, indanofan, indolauxipyr-cyanomethyl, eglinazine-ethyl, esprocarb, ethametsulfuron-methyl, ethalfluralin, ethidimuron, ethoxysulfuron, ethoxyfen, et Ethoxyfen-ethyl, ethofumesate, etobenzanid, epiriphenacil, endothal-disodium, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxyfluorfen, oryzalin, Obuda Pepper virus (Obuda Pepper Virus), orthosulfamuron, orbencarb, oleic acid, cafenstrole, caprylic acid, capric acid, carfentrazone-ethyl, carbutilate, carbetamide, quizalofop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, Xanthomonas campustris Campestris, quinoclamine, quinclorac, quinmerac, citric acid,Cumyloron, clacyfos, glyphosate (containing salts of sodium, potassium, amine, propylamine, isopropylamine, ammonium, isopropylammonium, guanidine, monoethanolamine, choline, BAPMA (N,N-bis-(aminopropyl)methylamine), dimethylamine or trimethium, etc.), glufosinate (containing salts of amine or sodium, etc.), glufosinate-P, glufosinate-P-sodium, clethodim, clodinafop, clodinafop-propargyl, clopyralid (containing monoethanolamine salt), clomazone, chlomethoxyfen fen), clomeprop, chloransulam-methyl, chloramben, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, chlorphthalim, chlorflurenol-methyl, chlorpropham, chlorbromuron, chloroxuron, chlorotoluron, ketospiradox (containing salts such as sodium, calcium, or ammonia), choletotrichum Colletotrichum orbiculare, Colletotrichum gloeosporioides, Colletotrichum truncatum,Chondrostercum purpureum, saflufenacil, sarmentine, cyanazine, cyanamide, diuron, diethatyl-ethyl, dioxopyritrione, dicamba (containing amines, diethylamine, isopropylamine, diglycolamine, dimethylammonium, diolamine, isopropylammonium, auramine, potassium, trolamine, BAPMA (N,N-bis-(aminopropyl)methylamine), choline, sodium or lithium salts, or esters such as methyl esters), cycloate, cyclooxydim , diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, diclobenil, diclofop, diclofop-P-methyl, diclofop-methyl, dichlorprop, dichlorprop-P (containing salts of dimethylammonium, potassium, sodium, choline, etc., or esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), diquat, diquat-dibromide Dibromide, dithiopyr, siduron, dinitramine, cinidon-ethyl, cinosulfuron, dinoseb (including acetate), dinoterb, cyhalofop, cyhalofop-butyl, cypyrafluone, diphenamid,Difenzoquat, diflufenican, diflufenzopyr, simazine, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, simetryn, dimepiperate, dimepyrolimet, dimefuron, Pseudomonas fluorescein Fluorescens), cinflubrolin, cinmethylin, swep, sulcotrione, sulfentrazone, sulfosate, sulfosulfuron, sulfometuron-methyl, setoxydim, Sclerotinia minor, terbacil, daimuron, thaxtomin A, Tobacco Mild Green Mosaic Tobamovirus, Tobacco Rattle Virus Virus), dalapon, thiazopyr, tiafenacil, thiencarbazone (including sodium salt, methyl ester, etc.), tiocarbazil, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryne,Tetflupyrolimet, thenylchlor, tebutam, tebuthiuron, tepraloxydim, tefuryltrione, terbuthylazine, ), terbutryn, terbumeton, tembotrione, toxapyzone, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tritosulfuron ron), tripyrasulfone, trifludimoxazin, triflusulfuron-methyl, trifluralin, trifloxysulfuron (including salts with sodium, etc.), tribenuron-methyl, tolpyralate, naptalam (including salts with sodium, etc.), naproanilide, nappropamide, nappropamide-M, nicosulfuron, lactic acid acid), Neburon, norflurazon, Burkholderia rinojensis, vernolate, paraquat, paraquat dichloride, halauxifen, halauxifen-benzyl, halauxifen-methyl, haloxyfop, haloxyfop-P, haloxyfop-etotyl,Haloxyfop-P-methyl, halosafen, halosulfuron-methyl, bixlozone, picloram (including salts with dichloroammonium, trolamine, etc.), picolinafen, bicyclopyrone, bispyribac-sodium, pinoxaden, bipyrazone, bifenox, piperophos, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron-ethyl (on-ethyl), pyrazolynate, bilanafos, pyraflufen, pyraflufen-ethyl, pyraquinate, pyridafol, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyriminobac-methyl, pyroxasulfone, pyroxsulam, phytopsola Palmibora (Phytophthora palmivora), phenisopham, fenuron, fenoxasulfone, fenoxaprop (containing methyl, ethyl, and isopropyl esters), fenoxaprop-P (containing methyl, ethyl, and isopropyl esters), feproxydim,Fenquinotrione, fendioxypyracil, fenthiaprop-ethyl, fentrazamide, fenpyrazone, phenmedipham, Phoma chenopodicola, Phoma herbarum, Phoma macrostoma, butachlor, butafenacil, butamifos, butyrate, Puccinia canaliculata, Puccinia sulcata Thlaspeos), butenachlor, butralin, butroxydim, flazasulfuron, flamprop (containing methyl, ethyl, and isopropyl esters), flamprop-M (containing methyl, ethyl, and isopropyl esters), primisulfuron, primisulfuron-methyl, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl (f luazifop-P-butyl), fluazolate, fluometuron, fluoroglycofen-ethyl, flucarbazone-sodium, fluchloraminopyr, fluchloralin, flucetosulfuron, flusulfinam, fluthiacet-methyl, flupyrsulfuron-methyl (sodium,(Containing salts such as calcium or ammonia), flufenauxirim, flufenacet, flufenazopyr, flufenoximacil, flufenpyr-ethyl, flupropanate (containing sodium salt), flupoxame, flumioxazin, flumiclor ac-pentyl), flumetsulam, fluridone, flurtamone, fluroxypyr (containing esters of butomethyl, meptyl, etc., or salts of sodium, calcium, ammonia, etc.), flurochloridone, pretilachlor, procarbazone (containing salts with sodium, etc.), broclozone, prochlorosulfone prochlorosulfone, prodiamine, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, propyrisulfuron, propham, Profluazol, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil (butyric acid,(including esters of octanoic acid or heptanoic acid, etc.), bromofenoxime, bromobutide, florasulam, florpyrauxifen, florpyrauxifen-benzyl, hexazinone, petoxamide, benazolin, benazolin-ethyl, penoxsulam, Pepino Mosaic Virus, heptamaloxyloglucan, beflubutamid, beflubutamid-M, pebulate, pelargonic acid acid), bencarbazone, benquitrione, benzfendizone, bensulide, bensulfuron, bensulfuron-methyl, benzobicyclon, benzofenap, bentazone, pentanochlor, pendimethalin, pentoxazone, benfluralin (benf luralin), benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, mecoprop (containing salts of sodium, potassium, isopropylamine, triethanolamine, dimethylamine, diolamine, trolamine, choline, etc., or esters such as ethadyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), mecoprop-P-potassium salt,Meso-sulfuron (including esters such as methyl), mesotrione, metazachlor, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam (including salts such as sodium), disodium methanearsone (, DSMA), methiozolin, methyldymuron, metoxuron, metosulam, metsulfuron-methyl, metobromuron, metproxybicyclone, metobenzuron, metolachlor, metribuzin, mepiquat chloride chloride), mefenacet, monosulfuron (including methyl, ethyl, and isopropyl esters), monolinuron, molinate, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium Sodium), lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, 2,2,2-trichloroacetic acid (TCA) (containing salts such as sodium, calcium or ammonia), 2,3,6-trichlorobenzoic acid (2,3,6-TBA), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D) (containing amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, diolamine, dodecylammonium, heptylammonium, tetradecylammonium, triethylammonium, tris(2-hydroxypropyl)ammonium, trolamine, choline, sodium or lithium salts, or esters such as butotyl ester, 2-butoxypropyl ester, 2-ethylhexyl ester, methyl ester, ethyl ester, butyl ester, isobutyl ester, octyl ester, pentyl ester, propyl ester, isoctyl ester, isopropyl ester, meptyl ester, tefuryl ester, etc.), 2,4-dichlorophenoxybutyric acid (2,4-DB) (containing amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, choline, sodium or lithium salts, or esters such as isoctyl ester), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (containing sodium, dimethylammonium (Containing salts of choline, etc., or esters such as 2-ethylhexyl ester, isoctyl ester, ethyl ester, etc.), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (containing sodium salt, ethyl ester, etc.), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 4,6-dinitro-O-cresol (DNOC) (containing salts of amine or sodium, etc.), (5S)-3-(3,5-difluorophenyl)-N-[rel-(3R,5R)-5-(trifluoromethylsulfonylcarbamoyl)terolahydrofuran-3 -yl]-5-vinyl-4H-isoxazole-5-carboxamide((5S)-3-(3,5-difluorophenyl)-N-[rel-(3R,5R)-5-(trifluoromethylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide)(chemical name, CAS registry number: 2266183-40-6)(International Publication No. 2018 / 228986, International Publication No. 2020 / 114934), N4-(2,(6-difluorophenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine (N4-(2,6-difluorophenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine) (Chemical name, CAS registry number: 1606999-43-2) (International Publication No. 2014 / 064094, International Publication No. 2015 / 162164), (5S)-3-(3,5-difluorophenyl)-N-[(3R)-5- (Methylsulfonylcarbamoyl)-2,3-dihydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide ((5S)-3-(3,5-difluorophenyl)-N-[(3R)-5-(methylsulfonylcarbamoyl)-2,3-dihydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide) (Chemical name, CAS registry number: 2266190-06-9) (International Publication No. 2018 / 228986, Japan) International Publication No. 2020 / 114934, (5R)-3-(3,5-difluorophenyl)-5-methyl-N-[rel-(3R,5R)-5-(methylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-4H-isoxazole-5-carboxamide((5R)-3-(3,5-difluorophenyl)-5-methyl-N-[rel-(3R,5R)-5-(methylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-4H-isoxazole (5R)-3-(3,5-difluorophenyl)-N-[(3R)-5-(methoxycarbamoyl)-2,3-dihydrofuran-3-yl]-5-methyl-4H-isoxazole-5-carboxamide((5R)-3-(3,5-difluorophenyl)-N-[(3R)-5-(methoxycarbamoyl)-2,3-dihydrofuran-3-yl]-5-methyl-4H-isoxazole-5-carboxamide) (Chemical name, CAS registry number: 2266170-31-2) (International Publication No. 2018 / 228986, International Publication No. 2020 / 114934), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidined-2-one (4-hydroxy-1-methyl-3-[4-(trifluoromethyl) -2-pyridyl]imidazolidin-2-one) (Chemical name, CAS registry number: 1708087-22-2) (International Publication No. 2015 / 059262, International Publication No. 2018 / 015476), 6-(1-fluorocyclopentyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine (6-(1-fluorocyclopentyl)-N4-(2,3,5,6-tetrafluorophenyl)-1 ,3,5-triazine-2,4-diamine) (chemical name, CAS registry number: 1820807-75-7) (International Publication No. 2015 / 162164), 6-(1-fluoro-1-methylethyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine (6-(1-fluoro-1-methylethyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-d iamine) (Chemical name, CAS registry number: 1606999-21-6) (International Publication No. 2014 / 064094, International Publication No. 2015 / 162164), (5S)-3-(3-fluoro-5-methylphenyl)-N-[rel-(3R,5R)-5-(methoxycarbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide((5S)-3-(3-fluoro-5-methylphenyl)-N-[rel-(3R,5R)-5-(methoxycarbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide) (Chemical name, CAS registry number: 2266292-43-5) (International Publication No. 2018 / 228986, International Publication No. 2020 / 114934), 6-(1-methylcyclobutyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine(6-(1-methylcyclobutyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5- triazine-4,4-diamine) (chemical name, CAS registry number: 1607001-97-7) (International Publication No. 2014 / 064094, International Publication No. 2015 / 162164), AE-F-150944 (code number), IR-6396 (code number), MCPA-thioethyl, SYP-298 (code number), SYP-300 (code number), S-ethyldipropylthiocarbamate (EPTC), S-metolachlor, S-9750 (code number), MSMA (monosodium methyl arsenate), HW-02 (code number).

[0124] Plant growth regulators: 1-naphthylacetamide, 1-methylcyclopropene, 1,3-diphenylurea, 2,3,5-triiodobenzoic acid 5-(trifluoromethyl)benzo[b]thiophen-2-carboxylate methyl (CPA), 2-(naphthalene-1-yl)acetamide, 2,6-diisopropylnaphthalene, 3-[(6-chloro-4-phenylquinazoline-2-yl)amino]propane-1-ol, 4-oxo-4-(2-phenylethyl)aminobutyric acid (chemical name, CAS registry number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), 5-aminolevulinic acid hydrochloride, 5-(trifluoromethyl)benzo[b]thiophen-2-carboxylate methyl (CPA) 5-(trifluoromethyl)benzo[b]thiofen-2-carboxylate), AVG (aminoethoxyvinylglycine), n-decyl alcohol, anisiflupurin, aviglycine, ancymidol, abscisic acid, isoprothiolane, inabenfide, indole acetic acid, indole butyric acid, uniconazole, uniconazole-P, Ecolyst, etychlozate, ethephon, epocholeone, calcium chloride, choline chlorideChloride, oxine sulfate, kinetin, calcium peroxide, carvone, calcium formate, cloxyfonac, cloxyfonac-potassium, cloprop, chlormequat, chlormequat-chloride, chlorpropham, choline, cytokinins, oxidized glutathione, cyanamide, sodium cyanate cyanate), cyclanilide, dichlorprop (containing salts of dimethylammonium, potassium, sodium, choline, etc., or esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), dichlorprop-P (containing salts of sodium, potassium, dimethylammonium, etc., or 2-ethylhexyl ester), diquat, diquat dibromide, dikegulac, gibberellinic acid, gibberellin A4, gibberellin A7, dimethipin, sintofen, jasmone, cis-jasmone, jasmonic acid, methyl jasmonate Jasmonate, streptomycin, calcium polysulfide, daminozide, calcium carbonateCarbonate, thidiazuron, decan-1-ol, triacontanol, tripenthenol, trinexapac-ethyl, tribufos, paclobutrazol, paraffin, bispyribac-sodium, hymexazol, butralin, fluthiacet-methyl, pyraflufen-ethyl ethyl), flumetralin, flurprimidol, flurenol, pronitridine, prohydrojasmon, prohexadione-calcium, heptamaloxyloglucan, 6-benzylaminopurine, pendimethalin, forchlorfenuron, formononetin, maleic hydrazide, mepiquat chloride, mefluidide, lipochitooligosaccharides (e.g., lipochitooligosaccharides SP104), calcium sulfate.

[0125] Next, examples of known pharmacokinetic mitigation compounds that may be mixed or used in combination are listed below.

[0126] Compounds that reduce drug-induced harm: Isoxadifen, isoxadifen-ethyl, oxabetrinil, octane-1,8-diamine, cloquintocet, cloquintcet-mexyl, dietholate, cyometrinil, dichlormid, dicyclonone, cyprosulfamide, daimuron, 1,8-naphthalic anhydride Anhydride), fenchlorazole, fenchlorazole-O-ethyl, fenchlorim, furilazole, fluxofenim, flurazole, benoxacor, metcamifen, mephenate, mefenpyr, mefenpi Mefenpyr-ethyl, mefenpyr-diethyl, lower alkyl-substituted benzoic acid, 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-dioxane (MG-191), 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro[4.5] Decane (AD-67), 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, code number), MON4660 (code number), N1,N2-diallyl-N2-dichloroacetylglycinamide (DKA-24, code number), 1-bromo-4-[(chloromethyl)sulfonyl]benzene (CSB), 2-propenyl 1-oxa-4-azaspiro[4,5]decane-4-carboditioate (MG-838, code number), 3-(dichloroacetyl)-2,2-dimethyl-1,3-oxazolidine (R-28725, code number), R-29148 (code number), 1-(dichloroacetyl)azepane (TI-35, code number).

[0127] Next, examples of known fungicides (fungicide-active ingredients) or disease control compounds that may be mixed or used in combination are listed below.

[0128] Bactericidal active ingredients or disease control compounds: Agrobacterium radiobacter, azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminotipyr, aminopyrifen, ametoctradin, aldimorph, isotianil, isopyrazam, isofetamide, isoflucypram, isoprothiolane iolane), ipconazole, ipflufenoquin, ipfentrifluconazole, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, imprimatin A A) Imprimatin B, edifenphos, etaconazole, etaboxam, ethirimol, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxyconazole, erysichrona, enprocymid, organic oiloils), oxadixyl, oxazinylazole, oxathiapiprolin, oxycarboxin, oxine-copper, oxytetracycline, oxpoconazole-fumarate, oxolinic acid, copper octanoate Candida dioctanoate, octhilinone, ofurace, orysastrobin, o-phenylphenol, kasugamycin, captafol, galquin, carpropamid, carbendazim, carboxin, carvone, carmeconazole, quinaminoprole, Candida oleophila, Candida cytoana saitoana), quinoxyfen, quinofumelin, chinomethionate, captan, quinconazole, quintozene, guazatine, cufraneb, coumethoxystrobin, coumoxystrobin, Gliocradium catenulatum, Cryptococcus albidus, kresoxim-methyl, clozylacon, Clonostachys rosearosea), chlozolinate, chloroinconazide, chlorothalonil, chloroneb, Chaetomium cupreum, Coniothyrium minitans, cyazofamid, diethofencarb, diclocymet, cyclobunofen, dichlofluanid, diclobentiazox, diclomezine, dichloran, dichlorophen, dithianon, diniconazole, diniconazole-M, di Zineb, Dinocap, Dipymetitrone, Diphenylamine, Difenoconazole, Cyflufenamid, Diflumetorim, Cyproconazole, Cyprodinil, Cyprometoxazam, Simeconazole, Dimethirimol, Dimethyl disulfide disulfide), dimethomorph, cymoxanil, dimoxystrobin, Pseudozyma flocculosa, Pseudomonas aureofaciens, Pseudomonas chlororaphis, Pseudomonas syringae, Pseudomonas fluoresceinflurorescens), Pseudomonas rhodesiae, ziram, silthiofam, Zucchini yellow mosaic virus (attenuated strain), streptomycin, Streptomyces griseoviridis, Streptomyces lygicus, spiroxamine, sedaxane, seboctylamine, zoxamide, solatenol, dazomet, Talaromyces flavus flavus), thiadinil, thiabendazole, thiram, thiophanate, thiophanate-methyl, thifluzamide, thiram, tecnazene, tecloftalam, tetraconazole, debacarb, tebuconazole, tebufloquin, terbinafine, dodine, dodemorph, triadimenol, triadimefon, triazoxide, triclamide, triclopyricarb, Trichoderma aspereram Trichoderma asperellum), Trichoderma atroviride, Trichoderma gamsii, Trichoderma stromaticum, Trichoderma paecilomyces, TrichodermaTrichoderma harzianum, Trichoderma viride, Trichoderma virens, Trichoderma polysporum, Trichoderma harzianum rifai, Trichoderma lignolan Lignorum), tricyclazole, triticonazole, tridemorph, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolnifanide, tolprocarb, nabam, natamycin, naftifine, nitrapyrin, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, Paenibacillus polymyxa, Burkholderia Burkholderia cepacia, Bacillus amyloliquefaciens, Bacillus simplex, Bacillus subtilis, Bacillus pumilus, Bacillus mycoides, Bacillus licheniformis, harpin protein, Variovorax paradoxus, validamycin, valifenalate, PantoeaPantoea agglomerans, picarbutrazox, bixafen, picoxystrobin, Pythium oligandrum, pydiflumetofen, bitertanol, binapacryl, hinokitiol, non-pathogenic Erwinia carotovora, non-pathogenic Rhizobium vitis (Rhizo bium vitis), biphenyl, bifemetstrobin, piperalin, hymexazol, pyraoxystrobin, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriophenone (p Pyriofenone, pyrisoxazole, pyridaclomethyl, pyrifenox, pyributicarb, pyribencarb, pyrimethanil, pyroquilon, vinclozolin, ferbam, famoxadone, phenazine oxide Fusarium oxide, fenamidone, fenaminstrobin, fenarimol, feneptamidoquin, fenoxanil, fenopyramid, ferimzone, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, folpet, phthalide, Fusarium oxysporumoxysporum), bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, furancarboxylic acid fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluxapyroxad, fluquinometoate, fluquinconazole, furconazole, furconazole-cis -cis), fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, flubeneteram, flumetylsulforim, flumetover, flumorph, Phlebiopsis gigantea(gigantea), proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, bronopol, propamocarb-hydrochloride, propiconazole, propineb, probenazole, bromuconazole, flometoquin, florylpicoxamid, hexaconazole, benalaxyl, benalaxyl. M (benalaxyl-M), benodanil, benomyl, pefurazoate, penconazole, pencycuron, benzovindiflupyr, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, fosetyl (containing salts of aluminum, calcium, sodium, etc.), polyoxin, polycarbamate, Bordeaux mixture mixture), mancopper, mancozeb, mandipropamid, mandestrobin, maneb, myclobutanil, mineral oiloils), mildiomycin, methasulfocarb, metam, metalaxyl, metalaxyl-M, metarylpicoxamide, metiram, methyltetraprole, metconazole, metcyclofenstrobin, metominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, meptyldinocap, mepronil, iodocarb, laminarin, ledprona, phosphorous acid and salts salts), basic copper oxychloride, silver, copper(II) sulfate, cuprous oxide, copper hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, copper sulfate, UK-2A (code number), bisethylenediamine copper complex [II] dodecylbenzenesulfonate (DBEDC), triphenyltin acetate (TPTA), triphenyltine chloride (TPTC), triphenyltin hydroxide (TPTH).

[0129] Next, examples of known biopesticides that may be mixed or used in combination are listed below.

[0130] Biopesticides: Haplothrips brevitubus, Franklinothrips vespiformis, Diglyphus isaea, Encarsia formosa, Amblyseius cucumeris, Pseudaphycus malinus, Amblyseius womersleyi, Aphidius colemani, Eretmocerus eremicus, Aphidoletes aphidimyza, Amblyseius swirskii, Orius Phytoseiulus persimilis, Amblyseius degenerans, Phytoseiulus persimilis, Orius sauteri, Dacnusa sibirica, Amblyseius californicus, Chrysoperla nipponensis, Anicetus beneficus.

[0131] Next, examples of known agricultural materials that may be mixed or used in combination are given.

[0132] Agricultural supplies: Ethylene, hypochlorous acid water (limited to that obtained by electrolysis of hydrochloric acid or potassium chloride aqueous solution), baking soda, vinegar, humic substances, humic acid, fulvic acid, seaweed extract, polysaccharides, amino acids, microbial materials, functional components derived from plants and animals, microbial metabolites, microbial activating materials, soil spreading agents, soil permeability adjusting materials, soil water retention materials, etc., and biostimulants.

[0133] Next, examples of known agricultural fertilizer components that may be mixed or used in combination are given below. Fertilizers include inorganic fertilizers and organic fertilizers, among others.

[0134] Agricultural fertilizer ingredients: Ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, ammonium urea nitrate, urea, calcium cyanamide, potassium nitrate, superphosphate, triple superphosphate, potassium dihydrogen phosphate, potassium chloride, potassium sulfate, potassium carbonate, potassium silicate, potassium phosphite, oilseed meal, fish meal, rice bran, bat guano, fermented chicken manure.

[0135] The pest control agent of the present invention, configured as described above, exhibits excellent control effects against harmful organisms such as grasshoppers, thrips, true bugs, beetles, flies, lepidopterans, wasps, springtails, silverfish, cockroaches, booklice, lice, plant parasitic mites, plant parasitic nematodes, plant parasitic mollusks, and other harmful animals, nuisance animals, sanitary pests, and parasites. Examples of such harmful organisms include the following species.

[0136] Examples of orthopteran pests include the grasshopper (Ruspolia lineosa) of the Tettigoniidae family, the field cricket (Teleogryllus emma) and the green grasshopper (Truljalia hibinonis) of the Gryllidae family, the mole cricket (Gryllotalpa orientalis) of the Gryllotalpa family, the short-winged grasshopper (Oxya hyla intricate), the migratory grasshopper (Locusta migratoria), the migratory grasshopper (Melanoplus sanguinipes), the differential grasshopper (Melanoplus differentialis), and the red-legged grasshopper (Melanoplus femurrubrum) of the Acrididae family, the Japanese grasshopper (Atractomorpha lata) of the Acrididae family, the Japanese grasshopper (Euscyrtus japonicus) of the Pyctotyphidae family, and the flea grasshopper (Xya japonicus) of the Acrididae family.

[0137] Examples of thrips include the Thripidae family species such as Frankliniella intonsa, Frankliniella occidentalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Thrips setosus, Heliothrips haemorrhoidalis, and Stenchaetothrips biformis, as well as the Thripidae family species such as Ponticulothrips diospyrosi and Liothrips Examples include the wasabiae thrips and the rice thrips (Haplothrips aculeatus).

[0138] Examples of Hemiptera pests include the cicada species Mogannia minuta, the spittlebug species Aphrophora intermedia and Mahanarva fimbriolata, the treehopper Machaerotypus sibiricus, the leafhopper Arboridia apicalis, Empoasca onukii, Nephotettix cincticeps, Nephotettix malayanus, Nephotettix virescens, Nephotettix nigropictus, and Recilia (Dorsalis), okra leaf hopper (Amrasca biguttula), mango leaf hopper (Idioscopus nitidulus, Idioscopus clypealis, Amritodus atkinsoni), potato leaf hopper (Empoasca fabae), corn leaf hopper (Dalbulus maidis), etc. Planthopper family: dwarf planthopper (Pentastiridius apicalis), etc. Planthopper family: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), corn planthopper (Peregrinus maidis), etc. Planthopper family: striped planthopper (Nisia nervosa), etc. Planthopper family: sugar planthopper (Kamendaka) Saccharivora, etc.; Red fungus back (Achilus flammeus) of the family Saccharividae, etc.; Tortoiseshell planthopper (Orosanga japonicus) of the family Orosangidae, etc.; Brown planthopper (Mimophantia maritima) of the family Mimophantidae, etc.; Psyllidae: pear psylla (Cacopsylla pyrisuga), citrus psylla (Diaphorina)citri, etc., mango psyllid (Calophya mangiferae) of the family Psyllidaceae, grape aphid (Daktulosphaira vitifoliae) of the family Phylloxera, larch aphid (Adelges laricis), spiny aphid (Adelges tsugae) of the family Aphididae, pea aphid (Acyrthosiphon pisum), cotton aphid (Aphis gossypii), spirea aphid (Aphis spiraecola), false radish aphid (Lipaphis erysimi), radish aphid (Brevicoryne brassicae), peach aphid (Myzus persicae), wheat aphid (Schizaphis Whiteflies such as graminum, wheat aphid (Rhopalosiphum padi), citrus aphid (Toxoptera aurautii), potato aphid (Aulacorthum solani), tulip aphid (Macrosiphum euphorbiae), currant lettuce aphid (Nasonovia ribisnigri), English grain aphid (Sitobion avenae), soybean aphid (Aphis glycines), etc., and whiteflies of the family Aleurocanthus (Aleurocanthus camelliae), citrus whitefly (Aleurocanthus spiniferus), tobacco whitefly (Bemisia tabaci), silverleaf whitefly (Bemisia argentifolii), greenhouse whitefly (Trialeurodes) Vaporariorum, etc., the cottonycomstocki, etc.; scale insects of the Coccidae family, such as the horned scale insect (Ceroplastes ceriferus) and the ruby ​​scale insect (Ceroplastes rubens); scale insects of the Coccidae family, such as the orange scale insect (Aclerda takahashii); scale insects of the Coccidae family, such as the red scale insect (Aonidiella aurantii), the pear scale insect (Diaspidiotus perniciosus), the mulberry scale insect (Pseudaulacaspis pentagoa), and the Yanon scale insect (Unaspis yanonensis); scale insects of the Miridae family, such as the turnedish plant bug (Lygus lineolaris), the red-bearded green stink bug (Trigonotylus caelestialium), the small green stink bug (Apolygus lucorum), and the tobacco stink bug (Nesidiocoris). * Limbativentris), Greenberry Stinkbug (Dichelops furcatus), etc., Taiwanese Stinkbug (Megacopta cribraria) of the family Pentatomidae, Pear Stinkbug (Urochela luteovoria) of the family Pentatomidae, and Long-winged Stinkbug (Cavelerius) of the family Lycaenidae.Examples include *Saccharivorus*, *Malcus japonicus* of the family Pentatomidae, *Dysdercus cingulatus* of the family Pentatomidae, *Leptocorisa acuta* and *Leptocorisa chinensis* of the family Coreidae, *Anacanthocoris striicornis* of the family Coreidae, *Rhopalus maculatus* of the family Coreidae, *Scaptocoris castanea* of the family Graptopetalidae, and bed bugs (Cimex lectularis) of the family Cordyceps.

[0139] Examples of beetle pests include the Scarabaeidae family species such as Anomara cuprea, Anomara rufocuprea, Popillia japonica, Oxycetonia jucunda, Anomara geniculata, Oryctes rhinoceros, Heptophylla picea, and Phyllophaga cuyabana, and the Elateridae family species such as Agriotes ogurae, Agriotes lineatus, Agriotes obscurus, and Melanotus. okinawensis), Melanotus fortnumi, etc., Anthrenus verbasci of the Dermestidae family, Heterobostrychus hamatipennis of the Long-horned Beetle family, Stegobium paniceum of the Cigarette Beetle family, Pitinus clavipes of the Leaf Beetle family, Tenebroides mauritanicus of the Flour Beetle family, Necrobia rufipes of the Cuckoo Beetle family, Carpophilus hemipterus of the Nitidulidae family, Pollen Beetle (Meligethes) Species such as *Aeneus*, the family Ahasverus advena, the family Cryptolestes ferrugineus, the family Epilachna varivestis and Henosepilachna vigintioctopunctata, the family Tenebrionidae Tenebrionidae Tenebrio molitor and Tribolium* Castaneum*, etc.; *Epicauta gorhami*, etc. of the family Meloidae; *Anoplophora glabripennis*, *Xylotrechus pyrrhoderus*, *Monochamus alternatus*, *Dectes texanus*, etc. of the family Cerambycidae; *Callosobruchus chinensis*, etc. of the family Curculionidae; *Leptinotarsa ​​decemlineata*, *Diabrotica virgifera virgifera*, *Diabrotica barberi*, *Diabrotica undecimpunctata howardi*, *Aulacophora*, etc. of the family Chrysomelidae femoralis), radish beetle (Phaedon brassicae), tortoise beetle (Cassida nebulosa), rice leaf beetle (Oulema oryzae), Mexican beetle (Epilachna varivestis), striped flea beetle (Phyllotreta striolata), spotted leaf beetle (Demotina fasciculata), cabbage stem flare beetle (Psylliodes chrysocephala), bean leaf beetle (Cerotoma trifurcate), grape colaspis (Colaspis brunnea), Iowa colaspis (Colaspis crinnicornis), soybean leaf minor (Odontota horni), corn flare beetle (Chaetocnema pulicaria), banded cucumber beetle (Diabrotica (Balteata), etc., the ant-mimicking weevil (Cylas formicarius) of the family Curculionidae, the alfalfa weevil (Hypera postica), the vegetable weevil (Listroderes costirostris), the sweet potato weevil (Euscepes) of the family Curculionidae(postfasciatus), chestnut weevil (Curculio sikkimensis), cotton flower weevil (Anthonomus grandis), soybean stalk weevil (Sternechus subsignatus), etc. (family Curculidae) rice weevil (Echinocnemus bipunctatus), rice water weevil (Lissorhoptrus oryzophilus), South American rice water weevil (Oryzophagus oryzae), etc. (family Curculidae) rice weevil (Sitophilus zeamais), grass weevil (Sphenophrus venatus), sugarcane weevil (Sphenophorus levis), etc. (family Barbidae) pine bark beetle (Tomicus piniperda), etc. (family Barbidae) berry bark beetle (Crossotarsus) Examples include the flat bark beetle (Lyctus brunneus) of the family Lyctidae, such as Lyctus niponicus.

[0140] Examples of fly pests include the crane fly (Tipula aino) of the family Tiliidae, the love bag fly (Plecia nearctica) of the family Bibidae, the mushroom gnat (Exechia shiitakevora) of the family Mycenathidae, the potato gnat (Pnyxia scabiei), the small mushroom gnat (Bradysia agrestis) of the family Mycenathidae, the soybean pod gall midge (Asphondylia yushimai), the Hessian gall midge (Mayetiola destructor), the blueberry gall midge (Dasineura oxycoccana) of the family Cicadidae, the Aedes aegypti and Culex pipiens pallens of the family Culicidae, and the cow gnat (Simulium) of the family Black flies. takahashii, etc., Chironomidae (rice midge), etc., Staphidae (golden-eyed horsefly), etc., Syrphidae (hymenoptera), etc., Tephritidae (citriaceae), etc., Oriental fruit fly, etc., Euphranta japonica, Mediterranean fruit fly, etc., Liriomyza trifolii, Liriomyza sativae, Agromyza oryzae, Eggplant leafminer, Liriomyza bryoniae, Chromatomyia (Horticola), onion leafminer (Liriomyza chinensis), etc., wheat leafminer (Meromyza nigriventris) etc., fruit fly (Drosophila suzukii) and yellow fruit fly (Drosophila melanogaster) etc., rice shore fly (Hydrellia griseola) etc., louse fly (Hippobosca equina) etc., dung fly (Parallelpmma) of the family Dung fliesExamples include the onion fly (Delia antiqua) and seed fly (Delia platura) of the family Deliidae, the house fly (Fannia canicularis) of the family Muscidae, the house fly (Musca domestica) and stable fly (Stomoxys calcitrans) of the family Muscidae, the flesh fly (Sarcophaga peregrina) of the family Sarcophagidae, the horse borer (Gasterophilus intestinalis) of the family Bovidae, the cow fly (Hypoderma lineatum) of the family Oestridae, and the sheep fly (Oestrus ovis) of the family Oestridae.

[0141] Examples of lepidopteran pests include the bat moth (Endoclita excrescens) of the Hemiptera family, the grape vine moth (Antispila ampelopsia) of the Mycidae family, the spotted vine moth (Zeuzera leuconotum) and the small vine moth (Cossus insularis) of the Cossidae family, the variegated leaf roller moth (Archips fuscocupreanus), the apple leaf roller moth (Adoxophyes orana fasciata), the pear fruit moth (Grapholita molesta), the tea leaf roller moth (Homona magnanima), the bean fruit moth (Leguminivora glycinivorella), the codling moth (Cydia pomonella), the European grapevine moss (Lobesia botrana), and the grape leaf roller moth (Eupoecilia) of the Tortricidae family. ambiguella, etc.; Psychidae: Bambalina sp., Eumeta minuscula, etc.; Tincturedidae: Nemapogon granella, Tinea translucens, etc.; Pycteridae: Bucculatrix pyrivorella, etc.; Leafmineridae: Lyonetiaprunifoliella malinella, etc.; Narrowtailidae: Caloptilia theivora, Phyllonorycter ringoniella, etc.; Leafmineridae: Phyllocnistis citrella, etc.; Tincturedidae: Acrolepiopsis Diamondback moth (Plutella xylostella) of the family Diamondback moth, apple moth (Yponomeuta orientalis) of the family Tineidae, apple leaf moth (Argyresthia conjugella) of the family Lycidae, grape clearwing moth (Nokona regalis), small clearwing moth (Synanthedin hector) of the family Sesiidae, potato moth (Phthorimaea) of the family Glaucus sapporensisOperaculella), Sitotroga cerealella, Pectinophora gossypiella, Tuta absoluta, Carposina sasakii (a member of the Coconut Moth family), Illiberis pruni (a member of the Zygaenidae family), Monema flavescens (a member of the Limacodidae family), Ancylolomia japonica (a member of the Crambidae family), Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia furnacalis, Hellulla undalis, Conogethes punctiferlis, Diaphania *Indica*, *Parapediasia teterrella*, *Ostrinia nubilalis*, *Diatraea saccharalis*, *Cadra cautella*, *Galleria mellonella*, *Nippoptilia vitis*, *Papilio xuthus*, *Pieris rapae*, *Parnara guttata*, *Ascotis selenaria*, *Dendrolimus spectabilis*, *Malacosoma neustrium* (e.g., testaceum), Sphingidae (e.g., Agrius convolvuli), Lymantriidae (e.g., Arna pseudoconspersa, Orygia recens approximans, Lymantria dispar), Arctiidae (e.g., Hyphantria cunea), Noctuidae (e.g., Agrotis)Examples include *Ipsilon*, *Agrotis segetum*, *Autographa nigrisigna*, *Helicoverpa armigera*, *Helicoverpa zea*, *Heliothis virescens*, *Spodoptera exigua*, *Spodoptera litura*, *Chrysodeixis includens*, *Spodoptera frugiperda*, and *Nephelodes minians*.

[0142] Examples of Hymenoptera pests include the rose sawfly (Arge pagana) of the Tenthredinidae family, the chestnut sawfly (Apethymus kuri) and the turnip sawfly (Athalia rosae ruficornis) of the Tenthredinidae family, the chestnut gall wasp (Dryocosmus kuriphilus) of the Gall wasp family, the yellow hornet (Vespa simillima xanthoptera) of the Vespidae family, the red imported fire ant (Solenopsis invicta) and the Argentine ant (Linepithema humile) of the Formicidae family, and the rose leafcutter wasp (Megachile nipponica) of the Leafcutter bee family.

[0143] Examples of springtail pests include the springtail *Bourletiella hortensis* of the family *Bourletiella*.

[0144] Examples of silverfish pests include the European silverfish (Lepisma saccharina) and the Japanese silverfish (Ctenolepisma villosa), both belonging to the family Lepisciidae.

[0145] Examples of cockroach pests include the American cockroach (Periplaneta americana) of the Blattidae family, the German cockroach (Blattella germanica) of the Blattidae family, the Taiwanese termite (Odontotermes formosanus) of the Termitidae family, the American drywood termite (Incisitermes minor) and the Japanese termite (Cryptotermes domesticus) of the Termitidae family, and the Formosan termite (Coptotermes formosanus) and the Japanese termite (Reticulitermes speratus) of the Termitidae family.

[0146] Examples of psocid pests include the small booklouse (Trogium pulsatorium) of the family Psocidae and the dark-skinned booklouse (Liposcelis corrodens) of the family Psocidae.

[0147] Examples of earwigs that are considered pests of the order Dermestidae include the earwig (Labodura riparia) of the family Dermestidae.

[0148] Examples of lice pests include the chicken lice (Lipeurus caponis) of the family Auricularidae and the cattle lice (Damalinia bovis) of the family Auricularidae.

[0149] Examples of lice pests include the pig louse (Haematopinus suis) of the family Cimicidae, the human louse (Pediculus humanus) of the family Cimicidae, the dog louse (Linognathus setosus) of the family Cimicidae, and the pubic louse (Pthirus pubis) of the family Cimicidae.

[0150] Examples of mite pests include the grain mite (Penthaleus major) of the family Pycnomidae, the cyclamen mite (Phytonemus pallidus) and the tea mite (Polyphagotarsonemus latus) of the family Limacodidae, a species of louse (Siteroptes sp.) of the family Scutellidae, the grape mite (Brevipalpus lewisi) of the family Scutellidae, the long-haired spider mite (Tuckerella pavoniformis) of the family Scutellidae, the apricot spider mite (Eotetranychus boreus), the citrus red mite (Panonychus citri), the apple red mite (Panonychus ulmi), the two-spotted spider mite (Tetranychus urticae), the Kanzawa spider mite (Tetranychus kanzawai) of the family Scutellidae, and the pine gall mite (Trisetacus) of the family Scutellidae. This includes species such as the citrus rust mite (Aculops pelekassi), pear rust mite (Epitrimerus pyri), citrus rust mite (Phyllocoptruta oleivora), and tomato rust mite (Aculops lycopersici) of the family Aculopidae, the wood gall mite (Diptacus crenatae) of the family Aculopidae, the wheat mite (Aleuroglyphus ovatus), the long-haired mite (Tyrophagus putrescentiae), and the robin mite (Rhizoglyphus robini) of the family Varroa, the honeybee mite (Varroa jacobsoni) of the family Varroidae, the mite (Dermanyssus gallinae) of the family Dermanyssus, and the bird mite (Ornithonyssus) of the family Ornithonyssus Examples include ticks such as *Ixodes sylviarum*, *Boophilus microplus*, *Rhipicephalus sanguineus*, and *Haemaphysalis longicornis* from the Tickidae family, and *Sarcoptes scabiei* from the Sarcoptidae family.

[0151] Examples of plant-parasitic nematodes include the grape nematode (Xiphinema index) of the family Longidoridae, the small nematode (Paratrichodorus minor) of the family Trichodoridae, a species of the family Rhabditella sp., a species of the family Aglenchus sp., a species of the family Cephalenchus sp., a species of the family Anguillidae (Nothotylenchus acris, Ditylenchus destructor), a species of the family Hoplolymidae (Rotylenchulus reniformis, Helicotylenchus dihystera), a species of the family Paratylenchidae (Paratylenchus curvitatus), and a species of the family Meloidogyne (Meloidogyne). (incognita), northern root-knot nematode (Meloidogyne hapla), Javan root-knot nematode (Meloidogyne javanica), Colombian root-knot nematode (Meloidogyne chitwoodi), false Colombian root-knot nematode (Meloidogyne fallax), etc. of the Heteroderaceae family: potato cyst nematode (Globodera rostochiensis), potato white cyst nematode (Globodera pallida), soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera Schachtii), etc. of the Tylenchorhynchus family: common nematode (Tylenchorhynchus claytoni), etc. of the Psilenchidae family: a species of spiral nematode (Psilenchus sp.), etc. of the Chryconeidae family: a species of petroleum nematode (Criconemoides sp.)) and others, such as the citrus nematode (Tylenchulus semipenetrans) of the Tylenculidaceae family, the camellia nematode (Sphaeronema camelliae) of the Spheronemaceae family, the citrus nematode (Radopholus citrophilus), the banana nematode (Radopholus similis), the false root-knot nematode (Nacobbus aberrans), the northern root-knot nematode (Pratylenchus penetrans), the southern root-knot nematode (Pratylenchus coffeae), the sorghum root-knot nematode (Pratylenchus zeae), the pineapple root-knot nematode (Pratylenchus brachyurus) of the Iotonchiumaceae family Examples include *Aphelenchus ungulatum*, the false root-knot nematode (*Aphelenchus avenae*) of the Aphelenchiaceae family, the rice nematode (*Aphelenchoides besseyi*) and the strawberry nematode (*Aphelenchoides fragariae*) of the Aphelencoideaceae family, and the pine wood nematode (*Bursaphelenchus xylophilus*) of the Parasitaphelenchiaceae family.

[0152] Examples of plant-parasitic mollusks include the apple snail (Pomacea canaliculata) of the family Pomacea, the slug (Leavicaulis alte) of the family Leavicaulidae, the African giant snail (Achatina fulica) of the family Achatina, the two-striped slug (Meghimatium bilineatum) of the family Limacidae, the land snail (Succinea lauta) of the family Lymnaeidae, the land snail (Discus pauper) of the family Patulaidae, the Japanese amber snail (Zonitoides yessoensis) of the family Limacidae, the Japanese amber snail (Limax flavus), the brown amber snail (Lehmannia valentiana), and the field slug (Deroceras) of the family Limacidae. Examples include *Parakaliella harimensis* from the family Parakaliidae, and *Acusta despecta sieboldiana* and *Bradybaena similaris* from the family Acustaeidae.

[0153] Other harmful organisms such as pests, nuisance animals, sanitary pests, livestock pests, and parasites include, for example, the American crayfish (Procambarus clarkii) of the family Ascidae, woodlice (Porcellio scaber) of the family Isopoda, pill bugs (Armadillidium vulgare) of the family Pillbugidae, centipede web pests such as the house centipede (Thereuonema tuberculata) of the family Scutigeridae and giant centipede (Scolopendra subspinipes) of the order Scolopendromorpha, millipede web pests such as the millipede (Oxidus gracilis) of the family Oxididae, redback spiders (Theridiidae hasseltii) of the family Theridiidae, and Cheiracanthium Examples include *Taenia japonicum*, the Afghan deathstalker (Androctonus crassicauda), nematode endoparasites such as roundworms (Ascaris lumbricoides), pinworms (Syphacia sp.), filarial worms (Wuchereria bancrofti), and flatworm endoparasites such as liver flukes (Distomum sp.), lung flukes (Paragonimus westermanii), Yokokawa's fluke (Metagonimus yokokawai), Japanese blood fluke (Schistosoma japonicum), Taenia solium, Taenia saginatus, Echinococcus sp., and Diphyllobothrium latum.

[0154] The pest control agent of the present invention is effective against pests such as those exemplified above that have acquired resistance to existing pest control agents. Furthermore, the pest control agent of the present invention can also be used on plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance through genetic modification, artificial crossbreeding, etc.

[0155] The "plants conferred with resistance by breeding methods or genetic modification technology" of this invention include not only plants conferred with resistance by classical crossbreeding and genetic modification technology, but also plants conferred with resistance by new breeding techniques (New Plant Breeding Techniques, NBTs) that combine conventional crossbreeding techniques with molecular biological methods. New breeding techniques (NBTs) are described in the book "Understanding New Plant Breeding Techniques" (International Literature Co., Ltd., by Ryo Osawa and Hiroshi Emoto), the review article "Genome Editing Tools in Plants" (Genes 2017, 8, 399, by Tapan Kumar Mohanta, Tufail Bashir, Abeer Hashem, Elsayed Fathi Abd_Allah and Hanhong Bae), etc.

[0156] The "crops for agricultural and horticultural use" of the present invention are not particularly limited, but examples include grasses, leafy and stem vegetables such as lettuce, Chinese cabbage, cabbage, broccoli, cauliflower, spinach, leeks, and onions, various vegetable crops such as tomatoes, cucumbers, and eggplants, and various flower crops such as lisianthus, statius, petunias, stocks, pansies, and chrysanthemums.

[0157] Next, the manufacturing method, formulation method, and uses of the compound of the present invention will be described in detail in the following examples, but the present invention is not limited in any way to these examples. The melting point, which is a physical property of the compound of the present invention, was measured using a Yanaco MP-500V micro-melting point analyzer. The refractive index was measured using an Atago Abbe refractometer. 1 The 1H-NMR spectrum was measured using a JEOL JNM-ECS300 (300 MHz) or JMTC-400 (400 MHz) with tetramethylsilane (TMS) as the internal standard. 1In H-NMR spectrum data, s represents a singlet, brs a broadened singlet, d a doublet, dd a double doublet, td a triple doublet, t a triplet, tt a triple triplet, q a quartet, quin a quintet, sep a septet, m a multiplet, and br a broad. CDCl3 represents deuterated chloroform, and DMSO-d6 represents deuterated dimethyl sulfoxide.

[0158] Furthermore, a method for producing the intermediate compound of the present invention is also described.

[0159] [Example 1] Preparation of (S)-N-(2-chloro-4-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)-3,3,3-trifluoropropanamide (compound number of this invention: P-0413)

[0160] (1) Preparation of (S)-2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)methyl benzoate A mixture of (S)-2-chloro-4-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}methyl benzoate (16.87 g, 42.85 mmol), N,N-diisopropylethylamine (8.86 g, 68.5 mmol), and acetonitrile (200 mL) was prepared according to the description in International Publication No. 2021 / 153720. Chloromethyl methyl ether (5.17 g, 64.2 mmol) was added dropwise to this mixture under ice cooling, and the mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with saturated citric acid aqueous solution, 1N sodium hydroxide aqueous solution, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 18.63 g of the target product (99% yield). 1H-NMR data (400MHz, CDCl3 / TMS δ(ppm)):7.49(1H,d),7.21(1H,d),4.87(2H,br),4.44(1H,m),4.25(1H,dd),4.10(1H,dd),3.94(3H,s),3.38(3H,s),1.48(3H,d)

[0161] (2) Preparation of (S)-N-{1-[4-chloro-2-fluoro-5-(hydroxymethyl)phenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide A mixture of lithium aluminum hydride (2.42 g, 63.8 mmol) and tetrahydrofuran (110 mL) was cooled on ice, and a mixture of (S)-2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)methyl benzoate (18.63 g, 42.55 mmol) and tetrahydrofuran (30 mL) was added dropwise, and the mixture was stirred on ice for 1 hour. Diisopropyl ether (140 mL) was added to the reaction solution, and after adding ice, the mixture was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 13.94 g of the target product (80% yield). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)):7.14(1H,d),7.12(1H,d),4.87(2H,br),4.73(2H,d),4.43(1H,m),4.24(1H,dd),4.10(1H,dd),3.39(3H,s),1.93(1H,br),1.47(3H,d)

[0162] (3) Preparation of (S)-N-{1-[5-(bromomethyl)-4-chloro-2-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide A mixture of (S)-N-{1-[4-chloro-2-fluoro-5-(hydroxymethyl)phenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (13.94 g, 34.02 mmol) and dichloromethane (100 mL) was sequentially added under ice cooling, followed by carbon tetrabromide (13.54 g, 40.82 mmol) and triphenylphosphine (10.71 g, 40.82 mmol). The mixture was stirred under ice cooling for 1 hour. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 1:0~3:1). The solvent was removed under reduced pressure to obtain 14.74 g of the target product (yield 92%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.15(1H,d),7.03(1H,d),4.87(2H,br),4.52(2H,s),4.43(1H,m),4.22(1H,dd),4.08(1H,dd),3.39(3H,s),1.47(3H,d)

[0163] (4) Preparation of (S)-N-{1-[5-(aminomethyl)-4-chloro-2-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride A mixture of (S)-N-{1-[5-(bromomethyl)-4-chloro-2-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (12.74 g, 26.95 mmol), di-tert-butyl iminodicarboxylate (8.78 g, 40.4 mmol), and N,N-dimethylformamide (80 mL) was mixed with potassium carbonate (5.59 g, 40.4 mmol) at room temperature and stirred for 17 hours at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain (S)-(tert-butoxycarbonyl)[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]carbamate tert-butyl. A mixture of the obtained (S)-(tert-butoxycarbonyl)[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]carbamate tert-butyl and ethyl acetate (10 mL) was mixed with ethyl acetate solution in 4N hydrogen chloride (50 mL) at room temperature and stirred for 15 hours at room temperature. Ethyl acetate was added to the reaction solution, washed with saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, ethyl acetate solution in 4N hydrogen chloride (60 mL) was added, and the mixture was stirred for 3 hours at room temperature. The solvent was removed under reduced pressure to obtain 7.61 g of the target product (63% yield). 1 H-NMR data (400MHz, DMSO-d6 / TMS δ(ppm)): 8.45(3H,brs),7.61(1H,d),7.57(1H,d),4.94(1H,br),4.83(1H,d),4.41(1H,m),4.22(2H,m),4.09(2H,s),3.28(3H,s),1.38(3H,d)

[0164] (5) Preparation of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]-3,3,3-trifluoropropanamide (compound number of the present invention: P-0453) (S)-N-{1-[5-(aminomethyl)-4-chloro-2-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (0.20 g, 0.45 mmol), triethylamine (0.11 g, 1.1 mmol), and dichloromethane (18 mL) were mixed and 3,3,3-trifluoropropionyl chloride (69 mg, 0.47 mmol) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 5 hours. The reaction solution was washed with 1N hydrochloric acid, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the solution was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:2). The solvent was removed under reduced pressure to obtain 0.20 g of the target product (yield 86%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.14(1H,d),7.00(1H,d),6.17(1H,br),4.86(2H,br),4.51(2H,d),4.40( 1H,m),4.20(1H,dd),4.07(1H,dd),3.40(3H,s),3.12(2H,q),1.45(3H,d)

[0165] (6) Preparation of (S)-N-(2-chloro-4-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)-3,3,3-trifluoropropanamide (compound number of the present invention: P-0413) A mixture of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]-3,3,3-trifluoropropanamide (0.11 g, 0.21 mmol) and dichloromethane (2 mL) was mixed with 1.2 mL of a 1 M boron tribromide solution in dichloromethane under ice cooling, and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1~3:2). The solvent was removed under reduced pressure to obtain 50.2 mg of the target product (yield 50%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.15(1H,d),7.03(1H,d),6.26(1H,br),5.52(1H,br),4.49(2H,d),4.11(1H,dd),4.05(1H,m),4.00(1H,dd),3.11(2H,q),1.46(3H,d)

[0166] [Example 2] Preparation of (S)-N-(2-chloro-4-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)-cyclopropanecarboxamide (compound number of this invention: P-0432)

[0167] (1) Preparation of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]cyclopropanecarboxamide (compound number of the present invention: P-0472) To a mixture of (S)-N-{1-[5-(aminomethyl)-4-chloro-2-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (1.20 g, 2.70 mmol), triethylamine (0.55 g, 5.4 mmol), and dichloromethane (20 mL), prepared in Example 1-(4), cyclopropanecarbonyl chloride (0.30 g, 2.9 mmol) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 4 hours. The reaction solution was washed with 1N hydrochloric acid, saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the solution was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 1:1). The solvent was removed under reduced pressure to obtain 1.24 g of the target product (yield 97%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.13(1H,d),7.03(1H,d),6.08(1H,br),4.86(2H,br),4.47(2H,d),4.40(1H,m),4.20(1H,dd ),4.07(1H,dd),3.38(3H,s),1.45(3H,d),1.38(1H,m),1.01-0.97(2H,m),0.79-0.74(2H,m)

[0168] (2) Preparation of (S)-N-(2-chloro-4-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)cyclopropanecarboxamide (compound number of the present invention: P-0432) A mixture of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]cyclopropanecarboxamide (0.20 g, 0.42 mmol) and dichloromethane (20 mL) was mixed with 2.3 mL of a 1 M boron tribromide solution in dichloromethane under ice cooling, and the mixture was stirred at room temperature for 14 hours. Water was added to the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 1:1). The solvent was removed under reduced pressure to obtain 0.15 g of the target product (yield 83%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.12(1H,d),7.05(1H,d),6.17(1H,br),5.76(1H,br),4.44(2H,d),4.09(1H,dd),4.0 4(1H,m),4.00(1H,dd),1.44(3H,d),1.38(1H,m),0.99-0.95(2H,m),0.79-0.75(2H,m)

[0169] [Example 3] Preparation of (S)-N-(4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)cyclopropanecarboxamide (compound number of this invention: P-0512)

[0170] (1) Production of 4-chloro-2-fluoro-5-methoxybenzoic acid A mixture of 4-chloro-2-fluoro-5-methoxybenzaldehyde (13.53 g, 71.75 mmol), tert-butanol (200 mL), tetrahydrofuran (200 mL), 2-methyl-2-butene (45.28 g, 645.7 mmol), and sodium dihydrogen phosphate (51.65 g, 430.5 mmol) in 150 mL of aqueous solution was prepared according to the description in International Publication No. 96 / 02485. Sodium chlorite (24.33 g, 215.2 mmol, 80% purity) in 110 mL of aqueous solution was added to the mixture in a water bath and stirred at room temperature for 2 hours. The organic layer and aqueous layer were separated, the solvent in the organic layer was removed under reduced pressure, the residue was dissolved in ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 13.91 g of the target product (95% yield). 1 H-NMR data (300MHz, DMSO-d6 / TMS δ(ppm)):7.60(1H,d),7.48(1H,d),3.90(3H,s)

[0171] (2) Production of 4-chloro-2-fluoro-5-hydroxybenzoic acid A mixture of 4-chloro-2-fluoro-5-methoxybenzoic acid (13.91 g, 67.99 mmol) and dichloromethane (200 mL) was mixed with a 1 M dichloromethane solution of boron tribromide (200 mL) under an ice bath, and the mixture was stirred at room temperature for 20 hours. The reaction solution was added to ice water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the resulting solid was washed with hexane to obtain 10.09 g of the target product (yield 78%). 1 1H-NMR data (300MHz, DMSO-d6 / TMS δ(ppm)): 10.55(1H,br), 7.46(1H,d), 7.43(1H,d)

[0172] (3) Preparation of ethyl 4-chloro-2-fluoro-5-hydroxybenzoate A mixture of 4-chloro-2-fluoro-5-hydroxybenzoic acid (10.09 g, 52.95 mmol) and ethanol (120 mL) was mixed with concentrated sulfuric acid (10 mL, 0.19 mol) at room temperature and stirred under reflux for 6 hours. The solvent was removed under reduced pressure, and the residue was extracted with ice water and ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 10.98 g of the target product (yield 95%). 1 H-NMR data (300MHz, CDCl3 / TMS δ(ppm)):7.58(1H,d),7.17(1H,d),5.51(1H,br),4.39(2H,q),1.39(3H,t)

[0173] (4) Preparation of (S)-5-[2-(tert-butoxycarbonylamino)propoxy]-4-chloro-2-fluorobenzoate ethyl A mixture of ethyl 4-chloro-2-fluoro-5-hydroxybenzoate (10.97 g, 50.18 mmol), (S)-2-(tert-butoxycarbonylamino)-1-propanol (13.19 g, 75.27 mmol), triphenylphosphine (19.74 g, 75.27 mmol), and tetrahydrofuran (170 mL) was cooled on ice, and diisopropyl azodicarboxylate (15.22 g, 75.27 mmol) was added. The mixture was stirred at room temperature for 63 hours. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 9:1~4:1). The solvent was removed under reduced pressure to obtain 18.18 g of the target product (yield 96%). 1 H-NMR data (300MHz, CDCl3 / TMS δ(ppm)): 7.44(1H,d),7.20(1H,d),4.78(1H,br),4.40(2H,q),4.11(1H,m),4.05-3.96(2H,m),1.45(9H,s),1.40(3H,t),1.34(3H,d)

[0174] (5) Preparation of (S)-5-(2-aminopropoxy)-4-chloro-2-fluorobenzoate ethyl hydrochloride A mixture of (S)-5-[2-(tert-butoxycarbonylamino)propoxy]-4-chloro-2-fluorobenzoate ethyl (18.18 g, 48.37 mmol) and 1,4-dioxane (90 mL) was mixed with a 1,4-dioxane solution in 4N hydrogen chloride (90 mL) at room temperature and stirred at room temperature for 24 hours. The solvent was removed under reduced pressure to obtain 15.14 g of the target product (100% yield). 1 H-NMR data (300MHz, DMSO-d6 / TMS δ(ppm)): 8.29(3H,br),7.69(1H,d),7.56(1H,d),4.34(2H,q),4.24(1H,dd),4.19(1H,dd),3.62(1H,m),1.33(3H,d),1.32(3H,t)

[0175] (6) Preparation of (S)-4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}ethyl benzoate A mixture of (S)-5-(2-aminopropoxy)-4-chloro-2-fluorobenzoate ethyl hydrochloride (15.14 g, 48.50 mmol), triethylamine (10.80 g, 106.7 mmol), and dichloromethane (220 mL) was cooled on ice, and trifluoromethanesulfonic anhydride (15.05 g, 53.35 mmol) was added. The mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate after adding 1N hydrochloric acid. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 4:1) to obtain 16.42 g of the target product (yield 83%). 1 H-NMR data (300MHz, CDCl3 / TMS δ(ppm)): 7.44(1H,d),7.23(1H,d),5.33(1H,br),4.41(2H,q),4.17-4.06(2H,m),4.04(1H,dd),1.52(3H,d),1.40(3H,t)

[0176] (7) Preparation of (S)-4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzoic acid Ethyl (S)-4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzoate (16.42 g, 40.27 mmol), tetrahydrofuran (30 mL), ethanol (150 mL), and water (50 mL) were mixed with lithium hydroxide monohydrate (5.07 g, 0.121 mol) at room temperature and stirred for 17 hours at room temperature. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate after adding 1N hydrochloric acid. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 14.37 g of the target product (yield 94%). 1 H-NMR data (300MHz, DMSO-d6 / TMS δ(ppm)): 9.64(1H,br),7.61(1H,d),7.51(1H,d),4.14(1H,dd),3.99(1H,dd),3.89(1H,m),1.28(3H,d)

[0177] (8) Preparation of (S)-4-chloro-2-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)methoxymethyl benzoate A mixture of (S)-4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzoic acid (0.51 g, 1.3 mmol), N,N-diisopropylethylamine (0.56 g, 4.3 mmol), and acetonitrile (10 mL) was mixed with chloromethyl methyl ether (0.32 g, 4.0 mmol) dropwise under ice cooling, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with saturated citric acid aqueous solution, 1N sodium hydroxide aqueous solution, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 0.63 g of the target product (100% yield). 1H-NMR data (400MHz, CDCl3 / TMS δ(ppm)):7.46(1H,d),7.25(1H,d),5.50(2H,s),4.90(2H,br),4.48(1H,m),4.24(1H,dd),4.10(1H,dd),3.57(3H,s),3.38(3H,s),1.51(3H,d)

[0178] (9) Preparation of (S)-N-{1-[2-chloro-4-fluoro-5-(hydroxymethyl)phenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide A mixture of lithium aluminum hydride (78 mg, 2.1 mmol) and tetrahydrofuran (10 mL) was cooled on ice, and a mixture of (S)-4-chloro-2-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)methoxymethyl benzoate (0.64 g, 1.4 mmol) and tetrahydrofuran (10 mL) was added dropwise. The mixture was stirred on ice for 3 hours. Diisopropyl ether (20 mL) was added to the reaction solution, ice was added, and the mixture was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 0.52 g of the target product (yield 93%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)):7.12(1H,d),7.02(1H,d),4.91(2H,br),4.74(2H,brs),4.44(1H,m),4.22(1H,dd),4.08(1H,dd),3.38(3H,s),1.83(1H,br),1.50(3H,d)

[0179] (10) Preparation of (S)-N-{1-[5-(bromomethyl)-2-chloro-4-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (S)-N-{1-[2-chloro-4-fluoro-5-(hydroxymethyl)phenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (0.52 g, 1.3 mmol) and dichloromethane (20 mL) were mixed and, under ice cooling, carbon tetrabromide (0.59 g, 1.8 mmol) and triphenylphosphine (0.47 g, 1.8 mmol) were added sequentially, and the mixture was stirred under ice cooling for 3.5 hours. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:1). The solvent was removed under reduced pressure to obtain 0.57 g of the target product (yield 95%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.15(1H,d),6.91(1H,d),4.91(2H,br),4.46(2H,d),4.45(1H,m),4.20(1H,dd),4.06(1H,dd),3.39(3H,s),1.51(3H,d)

[0180] (11) Preparation of (S)-N-{1-[5-(aminomethyl)-2-chloro-4-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride A mixture of (S)-N-{1-[5-(bromomethyl)-2-chloro-4-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (0.87 g, 1.8 mmol), di-tert-butyl iminodicarboxylate (0.60 g, 2.8 mmol), and N,N-dimethylformamide (10 mL) was mixed with potassium carbonate (0.38 g, 2.8 mmol) at room temperature and stirred for 90 hours at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain (S)-(tert-butoxycarbonyl)[4-chloro-2-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]carbamate tert-butyl. A mixture of the obtained (S)-(tert-butoxycarbonyl)[4-chloro-2-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]carbamate tert-butyl and ethyl acetate (10 mL) was mixed at room temperature with 10 mL of ethyl acetate solution in 4N hydrogen chloride and stirred for 16 hours at room temperature. Ethyl acetate was added to the reaction solution, washed with saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, 60 mL of ethyl acetate solution in 4N hydrogen chloride was added, and the mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure to obtain 0.42 g of the target product (52% yield). 1 H-NMR data (400MHz, DMSO-d6 / TMS δ(ppm)): 8.53(3H,brs),7.57(1H,d),7.55(1H,d),4.96(1H,br),4.85(1H,d),4.41(1H,m),4.20(2H,d),4.04(2H,m),3.29(3H,s),1.41(3H,d)

[0181] (12)(S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]cyclopropanecarboxamide (compound number of the present invention: P-0552) (S)-N-{1-[5-(aminomethyl)-2-chloro-4-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (0.33 g, 0.74 mmol), triethylamine (0.22 g, 2.2 mmol), and dichloromethane (20 mL) were mixed dropwise with cyclopropanecarbonyl chloride (77 mg, 0.74 mmol) under ice cooling, and the mixture was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1) to obtain 0.28 g of the target product (yield 79%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.12(1H,d),6.93(1H,d),6.01(1H,br),4.90(2H,br),4.45(2H,d),4.42(1H,m),4.18(1H,dd ),4.06(1H,dd),3.38(3H,s),1.48(3H,d),1.37(1H,m),1.01-0.97(2H,m),0.79-0.74(2H,m)

[0182] (13) Preparation of (S)-N-(4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)cyclopropanecarboxamide (compound number of the present invention: P-0512) A mixture of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]cyclopropanecarboxamide (0.15 g, 0.31 mmol) and dichloromethane (6 mL) was cooled on ice, and 1.3 mL of a 1 M boron tribromide solution in dichloromethane was added. The mixture was stirred at room temperature for 14 hours. Water was added to the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1~3:2). The solvent was removed under reduced pressure to obtain 0.10 g of the target product (yield 75%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.13(1H,d),6.96(1H,d),6.06(1H,br),5.62(1H,br),4.43(2H,d),4.08(1H,dd),4.0 5(1H,m),3.99(1H,dd),1.48(3H,d),1.36(1H,m),1.00-0.96(2H,m),0.80-0.75(2H,m)

[0183] [Example 4] Preparation of (S)-N-(4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)propionamide (compound number of this invention: P-0482)

[0184] (1) Preparation of (S)-N-[4-chloro-2-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]propionamide (compound number of this invention: P-0522) To a mixture of (S)-N-{1-[5-(aminomethyl)-2-chloro-4-fluorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (0.36 g, 0.81 mmol), propionic acid (72 mg, 0.97 mmol), N,N-diisopropylethylamine (0.16 g, 1.2 mmol), and N,N-dimethylformamide (8 mL) prepared in Example 3-(11), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.37 g, 0.97 mmol) was added at room temperature, and the mixture was stirred at room temperature for 16 hours. Saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was extracted with a mixed solvent of ethyl acetate and n-hexane. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate = 2:1) to obtain 0.34 g of the target product (yield 90%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.12(1H,d),6.93(1H,d),5.84(1H,br),4.90(2H,br),4.43(2H,d),4.42(1H,m) ,4.18(1H,dd),4.06(1H,dd),3.38(3H,s),2.24(2H,q),1.48(3H,d),1.17(3H,t)

[0185] (2) Preparation of (S)-N-(4-chloro-2-fluoro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)propionamide (compound number of this invention: P-0482) A mixture of (S)-N-[4-chloro-2-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]propionamide (0.23 g, 0.49 mmol) and dichloromethane (8 mL) was cooled on ice, and a 1 M solution of boron tribromide in dichloromethane (2.7 mL) was added. The mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1~3:2). The solvent was removed under reduced pressure to obtain 0.15 g of the target product (yield 72%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.10(1H,d),6.95(1H,d),6.28(1H,br),6.02(1H,br),4.39(2H,d),4.08-3.97(3H,m),2.23(2H,q),1.47(3H,d),1.14(3H,t)

[0186] [Example 5] Preparation of (S)-N-(2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)-3,3,3-trifluoropropanamide (compound number of this invention: P-0573)

[0187] (1) Preparation of methyl 2,4-dichloro-5-hydroxybenzoate A mixture of 2,4-dichloro-5-hydroxybenzoic acid (2.65 g, 12.8 mmol) and methanol (30 mL), prepared according to the description in Eur.J.Med.Chem., Vol. 34 (No. 9), pp. 729-744 (1999), was mixed with concentrated sulfuric acid (3 mL, 0.06 mol) at room temperature and stirred under reflux for 1 hour. The solvent was removed under reduced pressure, and the residue was extracted with ice water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 9:1-2:1). The solvent was removed under reduced pressure to obtain 2.32 g of the target product (yield 82%). 1 1H-NMR data (300MHz, CDCl3 / TMS δ(ppm)): 7.52 (1H,s), 7.45 (1H,s), 5.71 (1H,s), 3.93 (3H,s)

[0188] (2) Preparation of (S)-5-[2-(tert-butoxycarbonylamino)propoxy]-2,4-dichlorobenzoate methyl A mixture of methyl 2,4-dichloro-5-hydroxybenzoate (2.32 g, 10.5 mmol), (S)-2-(tert-butoxycarbonylamino)-1-propanol (2.21 g, 12.6 mmol), triphenylphosphine (3.30 g, 12.6 mmol), and tetrahydrofuran (25 mL) was cooled on ice, and diisopropyl azodicarboxylic acid (2.55 g, 12.6 mmol) was added. The mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 9:1~3:1). The solvent was removed under reduced pressure to obtain 3.96 g of the target product (100% yield). 1 H-NMR data (300MHz, CDCl3 / TMS δ(ppm)): 7.47(1H,s),7.40(1H,s),4.77(1H,br),4.17-3.98(3H,m),3.93(3H,s),1.45(9H,s),1.34(3H,d)

[0189] (3) Preparation of (S)-5-(2-aminopropoxy)-2,4-dichlorobenzoate methyl hydrochloride A mixture of (S)-5-[2-(tert-butoxycarbonylamino)propoxy]-2,4-dichlorobenzoate (3.96 g, 10.5 mmol) and 1,4-dioxane (20 mL) was mixed with a 1,4-dioxane solution in 4N hydrogen chloride (25 mL) at room temperature and stirred at room temperature for 20 hours. The solvent was removed under reduced pressure to obtain 3.30 g of the target product (100% yield). 1 H-NMR data (300MHz, DMSO-d6 / TMS δ(ppm)): 8.30(3H,br),7.81(1H,s),7.58(1H,s),4.28-4.18(2H,m),3.88(3H,s),3.63(1H,m),1.33(3H,d)

[0190] (4) Preparation of (S)-2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}methyl benzoate A mixture of (S)-5-(2-aminopropoxy)-2,4-dichlorobenzoate methyl hydrochloride (3.30 g, 10.5 mmol), triethylamine (1.59 g, 15.7 mmol), dichloromethane (35 mL), and tetrahydrofuran (35 mL) was cooled on ice, and trifluoromethanesulfonyl chloride (2.65 g, 15.7 mmol) was added. The mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate after adding 1N hydrochloric acid. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 4:1~2:1) to obtain 3.01 g of the target product (yield 70%). 1 H-NMR data (300MHz, CDCl3 / TMS δ(ppm)): 7.51(1H,s),7.39(1H,s),5.39(1H,br),4.18-4.08(2H,m),4.05(1H,dd),3.94(3H,s),1.51(3H,d)

[0191] (5) Production of (S)-2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzoic acid A mixture of (S)-2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}methyl benzoate (3.01 g, 7.34 mmol), tetrahydrofuran (10 mL), ethanol (40 mL), and water (20 mL) was mixed with lithium hydroxide monohydrate (0.92 g, 22 mmol) at room temperature and stirred for 66 hours at room temperature. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate after adding 1 N hydrochloric acid. The resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 2.69 g of the target product (yield 93%). 1 H-NMR data (300MHz, DMSO-d6 / TMS δ(ppm)): 9.65(1H,br),7.71(1H,s),7.52(1H,s),4.16(1H,dd),4.01(1H,dd),3.90(1H,m),1.27(3H,d)

[0192] (6) Preparation of Methoxymethyl (S)-2,4-Dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzoate A mixture of (S)-2,4-Dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzoic acid (0.75 g, 1.9 mmol), N,N-diisopropylethylamine (0.78 g, 6.1 mmol), and acetonitrile (12 mL) was cooled on ice, and chloromethyl methyl ether (0.46 g, 5.7 mmol) was added dropwise, and the mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with 1 M aqueous citric acid solution, 1 N aqueous sodium hydroxide solution, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 0.82 g of the target product (yield 89%). This product was used directly in the next step without purification.

[0193] (7) Preparation of (S)-N-{1-[2,4-dichloro-5-(hydroxymethyl)phenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide A mixture of lithium aluminum hydride (96 mg, 2.5 mmol) and tetrahydrofuran (3 mL) was cooled on ice, and a mixture of (S)-2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy) methoxymethyl benzoate (0.82 g, 1.7 mmol) and tetrahydrofuran (2 mL) was added dropwise. The mixture was stirred on ice for 1 hour. Diisopropyl ether (5 mL) was added to the reaction solution, ice was added, and the mixture was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 0.72 g of the target product (100% yield). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)):7.38(1H,s),7.10(1H,s),4.91(2H,br),4.75(2H,d),4.45(1H,m),4.24(1H,dd),4.11(1H,dd),3.36(3H,s),2.01(1H,br),1.50(3H,d)

[0194] (8) Preparation of (S)-N-{1-[5-(bromomethyl)-2,4-dichlorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide A mixture of (S)-N-{1-[2,4-dichloro-5-(hydroxymethyl)phenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (0.72 g, 1.7 mmol) and dichloromethane (6 mL) was sequentially mixed with carbon tetrabromide (0.67 g, 2.0 mmol) and triphenylphosphine (0.53 g, 2.0 mmol) under ice cooling, and the mixture was stirred under ice cooling for 2 hours. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:1). The solvent was removed under reduced pressure to obtain 0.64 g of the target product (yield 77%). 1H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.42(1H,s),6.96(1H,s),4.90(2H,br),4.53(2H,s),4.45(1H,m),4.22(1H,dd),4.08(1H,dd),3.38(3H,s),1.51(3H,d)

[0195] (9) Preparation of (S)-N-{1-[5-(aminomethyl)-2,4-dichlorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (S)-N-{1-[5-(bromomethyl)-2,4-dichlorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide (0.64 g, 1.3 mmol), iminodicarboxylate di-tert-butyl (0.43 g, 2.0 mmol), and N,N-dimethylformamide (10 mL) were mixed with potassium carbonate (0.27 g, 2.0 mmol) at room temperature and stirred for 15 hours at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain (S)-(tert-butoxycarbonyl)[2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]carbamate tert-butyl. To the mixture of the obtained (S)-(tert-butoxycarbonyl)[2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]carbamate tert-butyl and ethyl acetate (2 mL), 2 mL of ethyl acetate solution in 4N hydrogen chloride was added at room temperature, and the mixture was stirred at room temperature for 16 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and 6 mL of ethyl acetate solution in 4N hydrogen chloride was added, and the mixture was stirred at room temperature for 5 hours. The solvent was removed under reduced pressure to obtain 0.56 g of the target product (yield 93%). 1H-NMR data (400MHz, DMSO-d6 / TMS δ(ppm)): 8.29(3H,brs),7.71(1H,d),7.50(1H,brs),4.99(1H,br),4.84(1H,d),4.44(1H,m),4.21(2H,br),4.11(2H,br),3.28(3H,s),1.41(3H,d)

[0196] (10) Preparation of (S)-N-[2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]-3,3,3-trifluoropropanamide (compound number of the present invention: P-0613) (S)-N-{1-[5-(aminomethyl)-2,4-dichlorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (0.33 g, 0.71 mmol), triethylamine (0.22 g, 2.2 mmol), and dichloromethane (15 mL) were mixed and 3,3,3-trifluoropropionyl chloride (0.11 g, 0.75 mmol) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 5 hours. 1 M aqueous citric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1) to obtain 0.34 g of the target product (yield 89%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.40(1H,s),6.94(1H,s),6.26(1H,br),4.89(2H,br),4.53(2H,d),4.42( 1H,m),4.20(1H,dd),4.08(1H,dd),3.37(3H,s),3.12(2H,q),1.48(3H,d)

[0197] (11) Preparation of (S)-N-(2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)-3,3,3-trifluoropropanamide (compound number of the present invention: P-0573) A mixture of (S)-N-[2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]-3,3,3-trifluoropropanamide (0.24 g, 0.45 mmol) and dichloromethane (8 mL) was mixed with 2.5 mL of a 1 M boron tribromide solution in dichloromethane under ice cooling, and the mixture was stirred under ice cooling for 1 hour. Water was added to the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1~3:2). The solvent was removed under reduced pressure to obtain 0.16 g of the target product (yield 73%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.42(1H,s),6.97(1H,s),6.28(1H,br),5.46(1H,br),4.51(2H,d),4.10(1H,dd),4.07(1H,m),4.01(1H,dd),3.12(2H,q),1.48(3H,d)

[0198] [Example 6] Preparation of (S)-N-(2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)propionamide (compound number of this invention: P-0562)

[0199] (1) Preparation of (S)-N-[2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]propionamide (compound number of this invention: P-0602) To a mixture of (S)-N-{1-[5-(aminomethyl)-2,4-dichlorophenoxy]propan-2-yl}-1,1,1-trifluoro-N-(methoxymethyl)methanesulfonamide hydrochloride (0.23 g, 0.54 mmol), propionic acid (48 mg, 0.65 mmol), N,N-diisopropylethylamine (0.10 g, 0.81 mmol), and N,N-dimethylformamide (5 mL) prepared in Example 5-(9), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.25 g, 0.65 mmol) was added at room temperature and the mixture was stirred at room temperature for 18 hours. Saturated sodium bicarbonate aqueous solution was added to the reaction solution and extracted with a mixed solvent of ethyl acetate and n-hexane. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate = 2:1) to obtain 0.20 g of the target product (yield 77%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.39(1H,s),6.98(1H,s),5.93(1H,br),4.89(2H,br),4.47(2H,d),4.42(1H,m) ,4.20(1H,dd),4.08(1H,dd),3.38(3H,s),2.25(2H,q),1.48(3H,d),1.17(3H,t)

[0200] (2) Preparation of (S)-N-(2,4-dichloro-5-{2-[(trifluoromethyl)sulfonylamino]propoxy}benzyl)propionamide (compound number of this invention: P-0562) A mixture of (S)-N-[2,4-dichloro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]propionamide (0.12 g, 0.25 mmol) and dichloromethane (2 mL) was mixed with 1.5 mL of a 1 M boron tribromide solution in dichloromethane and stirred under ice cooling for 1 hour. Water was added to the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 2:1~3:2). The solvent was removed under reduced pressure to obtain 90 mg of the target product (yield 83%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.39(1H,s),7.02(1H,d),6.01(1H,br),5.83(1H,br),4.44(2H,d),4.10( 1H,dd),4.06(1H,m),4.03(1H,dd),2.24(2H,q),1.47(3H,d),1.15(3H,t)

[0201] [Example 7] Preparation of (S)-N-(2-chloro-5-{2-[(difluoromethyl)sulfonylamino]propoxy}-4-fluorobenzyl)cyclopropanecarboxamide

[0202] (1) Preparation of tert-butyl (5-bromo-2-chloro-4-fluorobenzyl)(tert-butoxycarbonyl)carbamate A mixture of 1-bromo-5-(bromomethyl)-4-chloro-2-fluorobenzene (4.30 g, 14.2 mmol), iminodicarboxylate di-tert-butyl (4.63 g, 21.3 mmol), and N,N-dimethylformamide (50 mL), prepared according to the description in International Publication No. 2020 / 259613, was mixed with potassium carbonate (2.95 g, 21.3 mmol) at room temperature and stirred for 110 hours at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:1). The solvent was removed under reduced pressure to obtain 4.46 g of the target product (yield 72%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.34(1H,d),7.16(1H,d),4.83(2H,br),1.47(18H,s)

[0203] (2) Production of (5-bromo-2-chloro-4-fluorophenyl)methanamine hydrochloride A mixture of (5-bromo-2-chloro-4-fluorobenzyl)(tert-butoxycarbonyl)carbamate tert-butyl (4.46 g, 10.2 mmol) and ethyl acetate (9 mL) was mixed with 30 mL of ethyl acetate solution in 4N hydrogen chloride at room temperature and stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction solution, washed with saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and 30 mL of ethyl acetate solution in 4N hydrogen chloride was added and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure to obtain 2.41 g of the target product (yield 86%). 1 H-NMR data (400MHz, DMSO-d6 / TMS δ(ppm)): 8.40(3H,brs),8.02(1H,d),7.79(1H,d),4.12(2H,s)

[0204] (3) Preparation of N-(5-bromo-2-chloro-4-fluorobenzyl)cyclopropanecarboxamide A mixture of (5-bromo-2-chloro-4-fluorophenyl)methaneamine hydrochloride (2.25 g, 8.18 mmol), triethylamine (2.48 g, 24.6 mmol), and dichloromethane (40 mL) was cooled on ice, to which cyclopropane carbonyl chloride (0.90 g, 8.61 mmol) was added dropwise, and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with 1 M citric acid aqueous solution, saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 2.46 g of the target product (yield 98%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.59(1H,d),7.18(1H,d),6.04(1H,br),4.49(2H,d),1.38(1H,m),1.03-0.99(2H,m),0.81-0.76(2H,m)

[0205] (4) Preparation of N-[2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)]cyclopropanecarboxamide A mixture of N-(5-bromo-2-chloro-4-fluorobenzyl)cyclopropanecarboxamide (1.23 g, 4.01 mmol), bis(pinacorato)diborone (1.22 g, 4.81 mmol), potassium acetate (1.18 g, 12.0 mmol), and 1,4-dioxane (25 mL) was mixed with [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (0.16 g, 0.20 mmol) under a nitrogen atmosphere and stirred at 100 °C for 3 hours. The reaction solution was cooled to room temperature, the solvent was removed under reduced pressure, and the solution was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate = 1:1). The solvent was removed under reduced pressure to obtain 1.10 g of the target product (yield 78%). 1H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.73(1H,d),7.11(1H,d),5.96(1H,br),4.52(2H,d),1.37-1.33(13H,m),1.02-0.98(2H,m),0.77-0.73(2H,m)

[0206] (5) Preparation of N-(2-chloro-4-fluoro-5-hydroxybenzyl)cyclopropanecarboxamide A mixture of N-[2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]cyclopropanecarboxamide (1.10 g, 3.11 mmol), tetrahydrofuran (20 mL), and water (10 mL) was mixed with sodium perborate tetrahydrate (0.58 g, 3.8 mmol) at room temperature and stirred for 15 hours at room temperature. The solvent was removed under reduced pressure, and the residue was added to 1 M aqueous citric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 4:1~3:2). The solvent was removed under reduced pressure to obtain 0.75 g of the target product (yield 99%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.11(1H,d),7.10(1H,d),7.00(1H,br),6.21(1H,br),4.45(2H,d),1.38(1H,m),1.03-0.98(2H,m),0.81-0.76(2H,m)

[0207] (6) Preparation of (S)-{1-[4-chloro-5-(cyclopropanecarboxamidemethyl)-2-fluorophenoxy]propan-2-yl}carbamate tert-butyl A mixture of N-(2-chloro-4-fluoro-5-hydroxybenzyl)cyclopropanecarboxamide (0.75 g, 3.1 mmol), (S)-2-(tert-butoxycarbonylamino)-1-propanol (0.65 g, 3.7 mmol), triphenylphosphine (1.20 g, 4.58 mmol), and tetrahydrofuran (20 mL) was mixed with diisopropyl azodicarboxylic acid (0.93 g, 4.6 mmol) under ice cooling, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 4:1~1:3). The solvent was removed under reduced pressure to obtain 1.20 g of the target product (yield 97%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.11(1H,d),7.06(1H,d),6.13(1H,br),4.74(1H,br),4.47(2H,d),4.09-3.93(3 H,m),1.45(9H,s),1.39(1H,m),1.29(3H,d),1.01-0.97(2H,m),0.78-0.73(2H,m)

[0208] (7) Preparation of (S)-N-[5-(2-aminopropoxy)-2-chloro-4-fluorobenzyl]cyclopropanecarboxamide hydrochloride A mixture of (S)-{1-[4-chloro-5-(cyclopropanecarboxamidemethyl)-2-fluorophenoxy]propan-2-yl}carbamate tert-butyl (1.20 g, 2.99 mmol) and ethyl acetate (9 mL) was mixed with ethyl acetate solution of 4N hydrogen chloride (30 mL) at room temperature and stirred at room temperature for 94 hours. The solvent was removed under reduced pressure to obtain 0.80 g of the target product (yield 79%). 1 H-NMR data (400MHz, DMSO-d6 / TMS δ(ppm)): 8.68(1H,br),8.31(3H,br),7.49(1H,d),7.24(1H,d),4.30(2H,d),4.2 2-4.10(2H,m),3.61(1H,m),1.69(1H,m),1.31(3H,d),0.73-0.65(4H,m)

[0209] (8) Preparation of (S)-N-(2-chloro-5-{2-[(difluoromethyl)sulfonylamino]propoxy}-4-fluorobenzyl)cyclopropanecarboxamide A mixture of (S)-N-[5-(2-aminopropoxy)-2-chloro-4-fluorobenzyl]cyclopropanecarboxamide hydrochloride (0.40 g, 1.2 mmol), pyridine (0.28 g, 3.6 mmol), and dichloromethane (10 mL) was cooled on ice, and difluoromethanesulfonyl chloride (0.89 g, 5.9 mmol) was added. The mixture was stirred at room temperature for 63 hours. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate after adding 1N hydrochloric acid. The organic layer was washed with saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 1:1) to obtain 90 mg of the target product (yield 18%). 1 H-NMR data (400MHz, CDCl3 / TMS δ(ppm)): 7.14(1H,d),7.06(1H,d),6.24(1H,t),6.12(1H,br),5.18(1H,br),4.46(2H,d),4.09(1H,dd ),4.04(1H,m),3.99(1H,dd),1.44(3H,d),1.37(1H,m),1.00-0.96(2H,m),0.79-0.75(2H,m)

[0210] [Example 8] Preparation of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]-N-methylcyclopropanecarboxamide (compound number of the present invention: P-1281) A mixture of (S)-N-[2-chloro-4-fluoro-5-(2-{[1,1,1-trifluoro-N-(methoxymethyl)methyl]sulfonylamino}propoxy)benzyl]cyclopropanecarboxamide (0.50 g, 1.0 mmol), iodomethane (0.22 g, 1.6 mmol), and N,N-dimethylformamide (6 mL) prepared in Example 2-(1) was mixed with sodium hydride (63 mg, 1.6 mmol, purity 60%) at room temperature and stirred for 5 hours at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 1:1). The solvent was removed under reduced pressure to obtain 0.45 g of the target product (yield 87%). 1 H-NMR data (400MHz, DMSO-d6 / TMS δ(ppm)): 7.42(1H,d),6.93(1H,d),4.90(1H,d),4.82(1H,d),4.60(2H,br),4.34(1H,m),4.20 -4.12(2H,m),3.28(3H,s),3.10(3H,s),1.94(1H,m),1.37(3H,d),0.80-0.69(4H,m)

[0211] Physical properties (melting point, refractive index, and 1 The 1H-NMR spectral data, including the values ​​from the above examples, are shown in Tables 34 to 41 below. The compound numbers and symbols in the tables have the same meaning as described above.

[0212] [Table 34]

[0213] [Table 35]

[0214] [Table 36]

[0215] [Table 37]

[0216] [Table 38]

[0217] [Table 39]

[0218] [Table 40]

[0219] [Table 41]

[0220] Next, specific examples of formulations of the pest control agent of the present invention using the compound of the present invention or an agriculturally acceptable salt thereof, manufactured as described above, will be explained. However, the type of compound, additive, and mixing ratio are not limited to these and can be changed within a wide range. Also, in the following explanation, "parts" means parts by mass.

[0221] [Formulation Example 1] Emulsion Ten copies of each compound listed in Tables 1-41 Cyclohexanone 30 parts Polyoxyethylene alkylaryl ether 11 parts Alkylbenzenesulfonate calcium 4 parts Methylnaphthalene 45 parts The above ingredients were uniformly dissolved to form an emulsion.

[0222] [Formulation Example 2] Wettable Powder Ten copies of each compound listed in Tables 1-41 0.5 parts of sodium salt of formalin condensate of naphthalene sulfonic acid 0.5 parts of polyoxyethylene alkylaryl ether Diatomaceous earth 24 parts Clay 65 The above ingredients were uniformly mixed and ground to form a wettable powder.

[0223] [Formulation Example 3] Powder Two copies of each compound listed in Tables 1 to 41. Diatomaceous earth (5 parts) Clay 93 The above ingredients were uniformly mixed and ground to obtain a powder.

[0224] [Formulation Example 4] Granules 5 copies of each compound listed in Tables 1-41 Sodium salt of lauryl alcohol sulfate 2 parts Sodium lignin sulfonate 5 parts Carboxymethylcellulose 2 parts Clay 86 The above ingredients were uniformly mixed and ground. This mixture was then mixed with an amount equivalent to 20 parts water, processed into granules of 14-32 mesh using an extrusion granulator, and then dried to obtain the granular material.

[0225] [Formulation Example 5] Flowable formulation 20 copies of each compound listed in Tables 1-41 Polyoxyethylene styrene-phenyl ether sulfate 4 parts Ethylene glycol 7 parts Silicone AF-118N (manufactured by Asahi Kasei Corporation) 0.02 parts Wednesday 68.98 parts The above ingredients were mixed in a high-speed agitator for 30 minutes, and then pulverized in a wet pulverizer to obtain a flowable formulation.

[0226] [Formulation Example 6] Granular wettable powder Ten copies of each compound listed in Tables 1-41 Sodium lignin sulfonate 5 parts Polyoxyethylene alkylaryl ether (1 part) Sodium polycarboxylate 3 parts White carbon 5 parts Pregelatinized starch (part 1) Calcium carbonate 65 units 10 parts water The above ingredients were mixed, kneaded, and pressed into granules. The resulting granular material was dried in a fluidized bed dryer to obtain a wettable powder granule.

[0227] Next, the effects of the pest control agent of the present invention will be explained with reference to test examples. [Test Example 1] Insecticide activity test for rice stem borer A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as the active ingredient. Rice seedlings were immersed in this solution and placed in plastic cups. Ten second-instar larvae of the rice stem borer were released into the cups and the cups were covered. The cups were then placed in a constant temperature room at 25°C, and the number of dead insects was investigated after 6 days. The mortality rate was calculated using the formula in Equation 1. The experiment was conducted in a single batch.

number

[0228] [Test Example 2] Insecticide activity test for brown planthopper A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as the active ingredient. Rice seedlings were immersed in this solution and placed in plastic cups. Ten second-instar brown planthopper larvae were released into these plastic cups and the cups were covered. The cups were then placed in a constant temperature room at 25°C, and after 6 days, the number of dead insects was investigated, and the mortality rate was calculated using the formula in Equation 1. The experiment was conducted in a single-cycle format. The result of the test, compared to the compound of 60%, P-0032、P-0072、P-0082、P-0093、P-0122、P-0133、P-0202、P-0282、P-0332、P-0333、P-0362、P-0372、P-0373、P-04 02、P-0411、P-0413、P-0432、P-0441、P-0442、P-0443、P-0444、P-0446、P-0 447、P-0448、P-0449、P-0450、P-0451、P-0452、P-0453、P-0454、P-0455、P- 0456、P-0457、P-0459、P-0462、P-0463、P-0464、P-0465、P-0469、P-0470、P -0472、P-0473、P-0474、P-0475、P-0477、P-0478、P-0481、P-0482、P-0483、 P-0484、P-0491、P-0492、P-0493、P-0494、P-0497、P-0512、P-0521、P-0522 、P-0515、P-0524、P-0531、P-0532、P-0533、P-0534、P-0537、P-0543、P-0547 、P-0548、P-0552、P-0555、P-0561、P-0562、P-0563、P-0564、P-0571、P-057 2、P-0573、P-0574、P-0575、P-0577、P-0592、P-0597、P-0598、P-0601、P-06 02、P-0603、P-0604、P-0611、P-0612、P-0613、P-0614、P-0615、P-0617、P-0 622、P-0632、P-0637、P-0638、P-0682、P-0693、P-0762、P-0773、P-0792、P-0 842、P-0853、P-0854、P-0872、P-0922、P-0933、P-0952、P-1002、P-1013、P- 1082、P-1093、P-1162、P-1173、P-1202、P-1213、P-1242、P-1253、P-1281、P -1282、P-1283、P-1285、P-1286、P-1287、P-1288、P-1289、P-1290、P-1291、 P-1292、P-1293、P-1294、P-1295、P-1297、P-1298、P-1300、P-1301、P-1303、P-1304, P-1305, P-1306, P-1307, P-1308, P-1309, P-1310, P-1311, P-131 2, P-1313, P-1314, P-1315, P-1316, P-1317, P-1322, P-1324, P-1326, P-1 327, P-1328, P-1329, P-1330, P-1331, P-1333, P-1334, P-1335, P-1337, P -1340, P-1341, P-1342, P-1343, P-1346, P-1347, and P-1348 had a mortality rate of over 90%. ,

[0229] [Test Example 3] Test of effectiveness in controlling spider mites A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as the active ingredient. Soybean seedlings that had been pre-inoculated with 35 female spider mites were immersed in this solution and air-dried. The treated soybean seedlings were placed in a constant temperature room at 25°C, and after 13 days, the number of surviving female mites was investigated, and the control efficacy was calculated using formula 2. The experiment was conducted in a single-row system.

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[0230] This invention provides a novel compound having excellent insecticidal activity, a manufacturing intermediate thereof, and a pest control agent containing it as an active ingredient. It is useful in the fields of pesticides and agriculture and has potential for industrial use.

Claims

1. General formula [I] 【Chemistry 1】 [In the formula, R １ is a C １ -C ６ alkyl group, a C ２ -C ６ alkenyl group, a C １ -C ６ haloalkyl group, a C １ -C ６ alkoxy group, a C １ -C ６ alkylthio C １ -C ６ alkyl group, a C １ -C ６ alkylsulfinyl C １ -C ６ alkyl group, a C １ -C ６ alkylsulfonyl C １ -C ６ alkyl group, a C １ -C ６ haloalkylthio C １ -C ６ alkyl group, a C １ -C ６ haloalkylsulfinyl C １ -C ６ alkyl group, a C １ -C ６ haloalkylsulfonyl C １ -C ６ alkyl group, cyano C １ -C ６ alkyl group, a C １ -C ６ alkoxy C １ -C ６ alkyl group, a C １ -C ６ haloalkoxy C １ -C ６ alkyl group, a C ３ -C ６ cycloalkyl group, a C １ -C ６ haloalkyl C ３ -C ６ cycloalkyl group, a C ３ -C ６ halocycloalkyl group, a C ３ -C ６ cycloalkyl C １ -C ６ alkyl group, C １ ~C ６ Alkylamino group (the amino group is C １ ~C ６ It exhibits a phenyloxy group (which may be substituted with an alkyl group) (the phenyl group may be monosubstituted with a nitro group), R ２ C is a hydrogen atom. １ ~C ６ alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ alkyl group, C １ ~C ６ Alkylcarbonyl group, or C １ ~C ６ It shows an alkoxycarbonyl group, R ３ is a hydrogen atom, halogen atom, nitro group, or C １ ~C ６ It shows an alkyl group, R ４ is a halogen atom, nitro group, C １ ~C ６ Alkyl alkyl group, or C １ ~C ６ It shows an alkoxy group, R ５ represents a hydrogen atom, C １ to C ６ alkyl group, C １ to C ６ haloalkyl group, cyano C １ to C ６ alkyl group, C １ to C ６ alkoxy C １ to C ６ alkyl group, C １ to C ６ alkylcarbonyl group, C ３ to C ６ cycloalkylcarbonyl group, C １ to C ６ alkoxycarbonyl group, C １ to C ６ alkylcarbonyloxy C １ to C ６ alkyl group, or C １ to C ６ alkoxycarbonyloxy C １ to C ６ alkyl group, and R ６ [This represents a hydrogen atom or a halogen atom.] A compound represented by, or a salt thereof.

2. A pesticide composition containing the compound described in claim 1, or a salt thereof, as an active ingredient.

3. The pesticide composition according to claim 2, wherein the pesticide composition further contains a surfactant.

4. A pest control agent containing the compound described in claim 1, or a salt thereof, as an active ingredient.

5. The pest control agent according to claim 4, wherein the pest control agent is an insecticide, a nematode killer, and a miticide.

6. A pest control agent according to claim 5, which has control efficacy against pests in paddy fields, cultivated fields, lawns, orchards, non-agricultural land, greenhouses, seedling facilities, and plant factories where agricultural and horticultural plants are cultivated.

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