Aryl oxadiazole compound, and agricultural and horticultural plant disease control agent

Abstract

To provide a superior agricultural and horticultural plant disease control agent.SOLUTION: The present invention provides an aryl oxadiazole compound represented by general formula [I] or a salt thereof, and an agricultural and horticultural plant disease control agent comprising the same as an active ingredient [where A1, A2, A3, and A4 each independently represent a nitrogen atom, CH, or C-R4; Y represents an oxygen atom or a sulfur atom; X represents a halogen atom; Z represents a C1-C6 alkyl group, a C1-C6 alkoxy group, or the like; R1 and R2 represent a hydrogen atom, a C1-C6 alkyl group, or the like; and R3 represents a C1-C6 alkyloxycarbonyl group, a phenyl group (the group being substituted with one or more substituents selected from R5 substituents), a C10-C12 aryl group (the group optionally being substituted with one or more substituents selected from R5 substituents), or a 5-12-membered heteroaryl group (the group optionally being substituted with one or more substituents selected from R5 substituents)].SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel aryloxadiazole compound or a salt thereof, and an agricultural and horticultural plant disease control agent containing the compound or the salt thereof as an active ingredient. [Background technology]

[0002] Patent Documents 1 to 4 describe amide derivatives having aryloxadiazole.

[0003] Patent Document 5 describes disubstituted amide derivatives having aryloxadiazoles.

[0004] Patent Document 6 describes an aniline derivative having a heteroaryl oxadiazole.

[0005] Patent Documents 7 and 8 describe amide derivatives having aryloxadiazoles.

[0006] The above patent documents do not disclose the aryloxadiazole compounds of the present invention at all. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2003 / 059887 [Patent Document 2] International Publication No. 2017 / 081311 [Patent Document 3] International Publication No. 2017 / 110862 [Patent Document 4] International Publication No. 2018 / 055135 [Patent Document 5] International Publication No. 2019 / 228289 [Patent Document 6] International Publication No. 2020 / 254494 [Patent Document 7] International Publication No. 2022 / 129190 [Patent Document 8] International Publication No. 2023 / 286855 Summary of the Invention [Problem to be solved by the invention]

[0008] In the cultivation of agricultural and horticultural crops, many plant disease control agents are used to control plant diseases caused by pathogenic fungi. However, conventional plant disease control agents often have insufficient control efficacy, or their use against plant diseases caused by pathogenic fungi is sometimes limited due to the emergence of pathogenic fungi resistant to the agents. Furthermore, they often cause phytotoxicity or contamination to plants, or do not necessarily have satisfactory performance in terms of toxicity to humans, livestock, and fish, and environmental impact. Therefore, there is a strong demand for the development of plant disease control agents that have fewer of these drawbacks and can be used safely. [Means for solving the problem]

[0009] As a result of extensive research, the present inventors have found that a drug containing an aryloxadiazole compound represented by the following formula [I] or a salt thereof as an active ingredient has a high control effect against plant diseases caused by pathogenic fungi in the cultivation of useful crops, and have thus completed the present invention.

[0010] That is, the gist of the present invention is as follows. (1) General formula [I]

[0011] [ka] [In the formula, A 1 , A 2 , A 3 , and A 4 are each independently a nitrogen atom, CH or CR 4 indicates, Y represents an oxygen atom or a sulfur atom; X represents a hydrogen atom or a halogen atom; Z is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, a cyanoC1-C6 alkyl group, a C1-C6 alkyloxyC1-C6 alkyl group, a C1-C6 haloalkyloxyC1-C6 alkyl group, a C3-C6 cycloalkyloxyC1-C6 alkyl group, a 3- to 6-membered heterocyclyloxyC1-C6 alkyl group (the 3- to 6-membered heterocyclyl group is R 5 C6 to C 12 Aryloxy C1-C6 alkyl group (the C6-C 12 Aryl groups are R 5 substituents), a 5- to 12-membered heteroaryloxy C1-C6 alkyl group (the 5- to 12-membered heteroaryl group is R 5 substituents), C1-C6 alkylamino C1-C6 alkyl group (the amino group may be substituted with one or more substituents selected from R 6 a C3-C6 cycloalkylamino C1-C6 alkyl group (the amino group may be substituted with a substituent selected from R 6 a 3- to 6-membered heterocyclylamino C1-C6 alkyl group (which may be substituted with a substituent selected from R 5 The amino group may be substituted with one or more substituents selected from R 6 may be substituted with a substituent selected from C6 to C 12 Arylamino C1-C6 alkyl group (the C6-C 12 Aryl groups are R 5 The amino group may be substituted with one or more substituents selected from R 6 a 5- to 12-membered heteroarylamino C1-C6 alkyl group (the 5- to 12-membered heteroaryl group may be substituted with a substituent selected from R 5 The amino group may be substituted with one or more substituents selected from R 6may be substituted by a substituent selected from the group consisting of a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 haloalkylthio C1-C6 alkyl group, a C3-C6 cycloalkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 haloalkylsulfinyl C1-C6 alkyl group, a C3-C6 cycloalkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a C1-C6 haloalkylsulfonyl C1-C6 alkyl group, a C3-C6 cycloalkylsulfonyl C1-C6 alkyl group, an amino group, a monoformylamino group, a C1-C6 alkylamino group (the amino group is selected from the group consisting of a C1-C6 alkylamino group and a C1-C6 alkylamino group), 6 a C3-C6 cycloalkylamino group (the amino group may be substituted with a substituent selected from R 6 a 3- to 6-membered heterocyclylamino group (which may be substituted with a substituent selected from R 5 The amino group may be substituted with one or more substituents selected from R 6 may be substituted with a substituent selected from C6 to C 12 Arylamino group (C6-C 12 Aryl groups are R 5 The amino group may be substituted with one or more substituents selected from R 6 a 5- to 12-membered heteroarylamino group (which may be substituted with a substituent selected from R 5 The amino group may be substituted with one or more substituents selected from R 6 may be substituted with a substituent selected from the group consisting of a C1-C6 alkyloxy group, a C1-C6 haloalkyloxy group, a C3-C6 cycloalkyloxy group, a 3- to 6-membered heterocyclyloxy group (the 3- to 6-membered heterocyclyl group is R 5 C6 to C 12 An aryloxy group (the group is R 5 substituents), a 5- to 12-membered heteroaryloxy group (which may be substituted with one or more substituents selected from R 5and C1-C6 alkylsulfonyl groups, C1-C6 haloalkylsulfonyl groups, C3-C6 cycloalkylsulfonyl groups, C1-C6 alkylthio groups, C1-C6 haloalkylthio groups, C3-C6 cycloalkylthio groups, C1-C6 alkylsulfinyl groups, C1-C6 haloalkylsulfonyl groups, C3-C6 cycloalkylsulfonyl groups, C6-C 12 an aryl group (the group is R 5 substituents), or a 5- to 12-membered heteroaryl group (the group may be substituted with one or more substituents selected from R 5 substituents), R 1 and R 2 each independently represents a hydrogen atom, a cyano group, a halogen atom, or a C1-C6 alkyl group, and R 1 and R 2 may each form a 3- to 6-membered monocyclic carbocyclic ring together with the carbon atom to which they are attached, and the carbocyclic ring may each be substituted by a hydrogen atom, a halogen atom, or a C1-C6 alkyl group; R 3 is a cyano group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C3-C6 cycloalkylcarbonyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkyloxyC1-C6 alkyl group, a C1-C6 haloalkyloxyC1-C6 alkyl group, a C3-C6 cycloalkyloxyC1-C6 alkyl group, a 3- to 6-membered heterocyclyloxyC1-C6 alkyl group (the 3- to 6-membered heterocyclyl group is R 5 C6 to C 12 Aryloxy C1-C6 alkyl group (the C6-C 12 Aryloxy groups are R 5 substituents), a 5- to 12-membered heteroaryloxy C1-C6 alkyl group (the 5- to 12-membered heteroaryl group is R 5substituents), a C1-C6 alkyloxycarbonyl group, a C1-C6 haloalkyloxycarbonyl group, a C3-C6 cycloalkyloxycarbonyl group, a C6-C 12 Aryl C1-C6 alkyloxycarbonyl group (the C6-C 12 Aryl groups are R 5 substituents), a 5-12-membered heteroaryl C1-C6 alkyloxycarbonyl group (the 5-12-membered heteroaryl group may be substituted by one or more substituents selected from R 5 substituents), a C1-C6 alkyloxyimino C1-C6 alkyl group, a C1-C6 haloalkyloxyimino C1-C6 alkyl group, a C3-C6 cycloalkyloxyimino C1-C6 alkyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C3-C6 cycloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C3-C6 cycloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C3-C6 cycloalkylsulfonyl group, a phenyl group (the group is 5 substituted with one or more substituents selected from the group consisting of C 10 ~C 12 an aryl group (the group is R 5 substituents), or a 5- to 12-membered heteroaryl group (the group may be substituted with one or more substituents selected from R 5 substituents), R 4 represents a halogen atom or a C1-C6 alkyl group, R 5 are each independently a cyano group, an amino group, a nitro group, a hydroxy group, a halogen atom, a thiol group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkylcarbonylamino group (the amino group is R 6 a C1-C6 alkylamino group (the amino group may be substituted with a substituent selected from R 6a C1-C6 alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from R 6 optionally substituted by a substituent selected from), a C1-C6 alkyloxy group, a C1-C6 haloalkyloxy group, a C3-C6 cycloalkyloxy group, a C1-C6 alkyloxy-C1-C6 alkyl group, a C1-C6 haloalkyloxy-C1-C6 alkyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C3-C6 cycloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C3-C6 cycloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, or a C3-C6 cycloalkylsulfonyl group; R 6 represents a formyl group, a C1-C6 alkyl group, a C1-C6 alkylcarbonyl group, or a C3-C6 cycloalkylcarbonyl group, or a salt thereof. (2) An agricultural and horticultural plant disease control agent, characterized by containing the aryloxadiazole compound or its salt described in (1) above as an active ingredient. (3) The agricultural and horticultural plant disease control agent according to (2), wherein the plant disease is caused by a pathogenic fungus. (4) The agricultural and horticultural plant disease control agent according to (3) above, wherein the pathogenic fungus is a Basidiomycete, Ascomycete, Deuteromycete, Oomycete, and / or Zygomycete. (5) An agricultural or horticultural plant disease control composition comprising the aryloxadiazole compound or salt thereof according to (1) above and an agriculturally acceptable carrier. (6) A method for controlling diseases of a useful plant, which comprises spraying an effective amount of the aryloxadiazole compound or its salt described in (1) above onto a useful plant or a part of a useful plant, or onto a place where the useful plant is growing. (7) The method according to (6), wherein the plant disease is caused by a pathogenic fungus. (8) The method according to (7) above, wherein the pathogenic fungus is a Basidiomycete, Ascomycete, Deuteromycete, Oomycete, and / or Zygomycete. (9) Use of the aryloxadiazole compound or its salt according to (1) above as an agricultural or horticultural plant disease control agent for useful plants. [Effects of the Invention]

[0012] The compounds of the present invention are useful as active ingredients of agricultural chemicals such as agricultural and horticultural plant disease control agents.

[0013] The agricultural and horticultural plant disease control agent containing the compound of the present invention exhibits excellent control effects against a wide range of plant diseases caused by basidiomycetes, ascomycetes, imperfect fungi, oomycetes, zygomycetes, etc., and can also control fungi that have acquired drug resistance. DETAILED DESCRIPTION OF THE INVENTION

[0014] The symbols and terms used in this specification will be explained below.

[0015] In the present invention, the term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0016] In the present invention, the notation "C1 to C6" indicates that the number of carbon atoms in the following substituent is 1 to 6 in this case.

[0017] In the present invention, unless otherwise specified, the term "C1 to C6 alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and examples thereof 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, and 1-ethyl-2-methylpropyl groups.

[0018] In the present invention, unless otherwise specified, the term "C1-C6 haloalkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 13 identical or different halogen atoms, and examples thereof 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 butyl, 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-fluorobutyl Fluoropentyl, 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-hexyl Examples of groups include butafluorohexyl, 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, and 6-iodohexyl.

[0019] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms, and the ring may be optionally substituted with an alkyl group within the specified range of carbon atoms. Examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, and cyclohexyl groups.

[0020] In the present invention, unless otherwise specified, the term "C2 to C6 alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof 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, 1-ethyl-2-propenyl, and the like. ropenyl, 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-bi 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 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 groups can be mentioned.

[0021] In the present invention, unless otherwise specified, the term "C2 to C6 alkynyl group" refers to a linear or branched alkynyl group having 2 to 6 carbon atoms, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, and 1-hexynyl. Examples of such groups include 1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butynyl, and 2,2-dimethyl-3-butynyl.

[0022] In the present invention, unless otherwise specified, the term "C1 to C6 alkylcarbonyl group" refers to a (C1 to C6 alkyl)-C(=O)- group in which the alkyl moiety has the above meaning, and examples thereof 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, and hexanoyl.

[0023] In the present invention, unless otherwise specified, the term "C1-C6 haloalkylcarbonyl group" refers to a (C1-C6 haloalkyl)-C(=O)- group in which the haloalkyl moiety has the above meaning, and examples thereof include fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, trichloroacetyl, tribromoacetyl, 3,3,3-trifluoropropionyl, 3,3-difluoropropionyl, and 4,4,4-trifluorobutyryl.

[0024] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkylcarbonyl group" refers to a (C3 to C6 cycloalkyl)-C(=O)- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, and cyclohexylcarbonyl groups.

[0025] In the present invention, the term "formyl group" refers to an HC(=O)- group.

[0026] In the present invention, the term "monoformylamino group" refers to a HC(=O)-NH- group.

[0027] In the present invention, unless otherwise specified, the term "C1-C6 alkylcarbonylamino group" refers to a (C1-C6 alkyl)-C(=O)-NH- group in which the alkyl moiety has the above meaning, and examples thereof include acetylamino, propionylamino, butyrylamino, and isobutyrylamino groups.

[0028] In the present invention, unless otherwise specified, the term "C1 to C6 alkylamino group" refers to a (C1 to C6 alkyl)-NH- group in which the alkyl moiety has the above meaning, and examples thereof include methylamino, ethylamino, n-propylamino, and isopropylamino groups.

[0029] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkylamino group" refers to a (C3 to C6 cycloalkyl)-NH- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropylamino, cyclobutylamino, cyclopentylamino, and cyclohexylamino groups.

[0030] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylamino group" refers to a (3- to 6-membered heterocyclyl)-NH- group in which the heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridinylamino, oxiranylamino, oxetanylamino, thietanylamino, tetrahydrofuranylamino, tetrahydropyranylamino, azetidinylamino, pyrrolidinylamino, piperidinylamino, piperazinylamino, dihydroisoxazolylamino, dioxaborolanylamino, dioxolanylamino, dioxanylamino, and morpholinylamino groups.

[0031] In the present invention, "C6 to C 12 Unless otherwise specified, the term "aryl group" refers to an aromatic hydrocarbon group having 6 to 12 carbon atoms, and examples thereof include phenyl, biphenyl, naphthalene-1-yl, and naphthalene-2-yl groups.

[0032] In the present invention, "C 10 ~C 12 Unless otherwise specified, the term "aryl group" refers to an aromatic hydrocarbon group having 10 to 12 carbon atoms, and examples thereof include biphenyl, naphthalene-1-yl, and naphthalene-2-yl groups.

[0033] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryl group" refers to a 5- to 12-membered monocyclic or fused bicyclic aromatic heterocycle containing, in addition to carbon atoms, one or more heteroatoms selected from a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the monocyclic aromatic heterocycle include pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridinon-1-yl, pyridinon-3-yl, pyridinon-4-yl, pyridinon-5-yl, pyridinon-6-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridinon-6-yl, pyrimidin-7-yl, pyrimidin-8-yl, pyrimidin-9-yl, pyrimidin-10-yl, pyrimidin-11-yl, pyrimidin-12-yl, pyrimidin-13-yl, pyrimidin-14-yl, pyrimidin-15-yl, pyrimidin-16-yl, pyrimidin-17-yl, pyrimidin-18-yl, pyrimidin-19-yl, pyrimidin-20-yl, pyrimidin-21-yl, pyrimidin-22-yl, pyrimidin-23-yl, pyrimidin-24-yl, pyrimidin-25-yl, pyrimidin-26-yl, pyrimidin-27-yl, pyrimidin-28-yl, pyrimidin-29-yl, pyrimidin-21-yl, pyrimidin-21-yl, pyrimidin-23-yl, pyrimidin-24-yl, pyrimidin-25-yl, pyrimidin-26-yl, pyrimidin-27-yl, pyrimidin-28-yl, pyrimidin-29-yl, pyrimidin-29-yl, pyrimidin-21-yl, pyrimidin-20-yl, pyrimidin-21-yl, pyr 1,2,3-triazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,3,5-triazinyl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyran-2-yl, pyran-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, thiazol-2-yl, thiazol- 4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, 1,4,5-triazol-1-yl, 1,4,5-triazol-4-yl, 1,4,5-triazol-5-yl, 1,2,4-triazol-1-yl, 1,2,4- Triazol-3-yl, 1,2,4-triazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,Examples of the fused bicyclic heterocycle include a fused bicyclic heterocycle formed by combining one of the monocyclic groups with a phenyl ring, or one of the heteroaromatic monocyclic groups with a C8-C, 10Fused bicyclic moieties formed by condensing to form a bicyclic group, e.g., indolyl-1-yl, indolyl-2-yl, indolyl-3-yl, indolyl-4-yl, indolyl-5-yl, indolyl-6-yl, indolyl-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl, benzimidazol-7-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazo Indazol-5-yl, indazol-6-yl, indazol-7-yl, benzotriazol-1-yl, benzotriazol-4-yl, benzotriazol-5-yl, benzotriazol-6-yl, benzotriazol-7-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl yl, quinolin-8-yl, benzothiazol-2-yl, benzothiazol-4-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzothiazol-7-yl, benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl, benzofuran-7-yl, benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-4-yl, benzothiophen-5-yl, benzothiophen-6-yl, benzothiophen-7-yl, benzisoxazo benzisoxazol-3-yl, benzisoxazol-4-yl, benzisoxazol-5-yl, benzisoxazol-6-yl, benzisoxazol-7-yl, pyrazolopyridin-1-yl, pyrazolopyridin-3-yl, pyrazolopyridin-4-yl, pyrazolopyridin-5-yl, pyrazolopyridin-6-yl, pyrazolopyrimidin-1-yl, pyrazolopyrimidin-2-yl, pyrazolopyrimidin-3-yl, pyrazolopyrimidin-5-yl, pyrazolopyrimidin-6-yl, pyrazolopyrimidin-7-yl, pyrrolopyridin-1-yl,Pyrrolopyridin-2-yl, pyrrolopyridin-3-yl, pyrrolopyridin-4-yl, pyrrolopyridin-5-yl, pyrrolopyridin-6-yl, triazolopyridin-3-yl, triazolopyridin-4-yl, triazolopyridin-5-yl, triazolopyridin-6-yl, triazolopyridin-7-yl, triazolopyrimidin-2-yl, triazolopyrimidin-3-yl, triazolopyrimidin-6-yl, triazolopyrimidin-7-yl, quinazoline-2 quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl, quinazolin-8-yl, quinoxalin-2-yl, quinoxalin-3-yl, quinoxalin-5-yl, quinoxalin-6-yl, quinoxalin-7-yl, quinoxalin-8-yl, cinnolin-3-yl, cinnolin-4-yl, cinnolin-5-yl, cinnolin-6-yl, cinnolin-7-yl, or cinnolin-8-yl groups, etc., can be mentioned.

[0034] In the present invention, "C6 to C 12 Unless otherwise specified, the term "arylamino group" refers to a group in which the aryl moiety has the above meaning (C6 to C 12 aryl)-NH- group, and examples thereof include phenylamino, biphenylamino, naphthalen-1-ylamino, and naphthalen-2-ylamino groups.

[0035] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylamino group" refers to a (5- to 12-membered heteroaryl)-NH- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include pyridylamino, pyrimidinylamino, pyrazinylamino, pyridazinylamino, triazinylamino, thienylamino, furanylamino, pyrrolylamino, pyrazolylamino, thiazolylamino, isothiazolylamino, oxazolylamino, isoxazolylamino, imidazolylamino, triazolylamino, thiadiazolylamino, and oxadiazolylamino. Examples of such groups include zolylamino, tetrazolylamino, indolylamino, benzimidazolylamino, indazolylamino, benzotriazolylamino, isoquinolinylamino, quinolinylamino, benzothiazolylamino, benzofuranylamino, benzothienylamino, benzisoxazolylamino, pyrazolopyridylamino, pyrazolopyrimidinylamino, pyrrolopyridylamino, triazolopyridylamino, triazolopyrimidinylamino, quinazolinylamino, quinoxalinylamino, and cinnolinylamino groups.

[0036] In the present invention, unless otherwise specified, the term "C1 to C6 alkylaminocarbonyl group" refers to a (C1 to C6 alkyl)-NH-C(=O)- group in which the alkyl moiety has the above meaning, and examples thereof include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 1-ethylpropylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, and n-hexylaminocarbonyl.

[0037] In the present invention, unless otherwise specified, the term "C1 to C6 alkyloxy group" refers to a (C1 to C6 alkyl)-O- group in which the alkyl moiety has the above meaning, and examples thereof include methoxy, ethyloxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1-ethylpropyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, and n-hexyloxy.

[0038] In the present invention, unless otherwise specified, the term "C1-C6 haloalkyloxy group" refers to a (C1-C6 haloalkyl)-O- group in which the haloalkyl moiety has the above meaning, and examples thereof include difluoromethoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethyloxy, 1-chloroethyloxy, 2-chloroethyloxy, 1-bromoethyloxy, 2-bromoethyloxy, 2,2-difluoroethyloxy, 1,2-dichloroethyloxy, and the like. oxy, 2,2-dichloroethyloxy, 2,2,2-trifluoroethyloxy, 2,2,2-trichloroethyloxy, 1,1,2,2-tetrafluoroethyloxy, pentafluoroethyloxy, 2-bromo-2-chloroethyloxy, 2-chloro-1,1,2,2-tetrafluoroethyloxy, 1-chloro-1,2,2,2-tetrafluoroethyloxy, 1-chloropropyloxy, 2-chloropropyloxy, 3-chloropropyloxy, 2-bromopropyloxy, 3-bromopropyloxy, 2-bromo-1-methylethyloxy , 3-iodopropyloxy, 2,3-dichloropropyloxy, 2,3-dibromopropyloxy, 3,3,3-trifluoropropyloxy, 3,3,3-trifluoro-2-propyloxy, 3,3,3-trichloropropyloxy, 3-bromo-3,3-difluoropropyloxy, 2,2-difluoropropyloxy, 3,3-dichloro-3-fluoropropyloxy, 2,2,3,3-tetrafluoropropyloxy, 1-bromo-3,3,3-trifluoropropyloxy, 2,2,3,3,3-pentafluoropropyloxy , 2,2,2-trifluoro-1-trifluoromethylethyloxy, heptafluoropropyloxy, heptafluoro-2-propyloxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, 2-chlorobutyloxy, 3-chlorobutyloxy, 4-chlorobutyloxy, 2-chloro-1,1-dimethylethyloxy, 4-bromobutyloxy, 3-bromo-2-methylpropyloxy, 2-bromo-1,1-dimethylethyloxy, 2,2-dichloro-1,1-Dimethylethyloxy, 2-chloro-1-chloromethyl-2-methylethyloxy, 4,4,4-trifluorobutyloxy, 3,3,3-trifluoro-1-methylpropyloxy, 3,3,3-trifluoro-2-methylpropyloxy, 2,3,4-trichlorobutyloxy, 2,2,2-trichloro-1,1-dimethylethyloxy, 4-chloro-4,4-difluorobutyloxy, 4,4-dichloro-4-fluorobutyloxy, 4-bromo-4,4-difluorobutyloxy, 2,4-dibromo-4,4-difluorobutyloxy , 3,4-dichloro-3,4,4-trifluorobutyloxy, 3,3-dichloro-4,4,4-trifluorobutyloxy, 4-bromo-3,3,4,4-tetrafluorobutyloxy, 4-bromo-3-chloro-3,4,4-trifluorobutyloxy, 2,2,3,3,4,4-hexafluorobutyloxy, 2,2,3,4,4,4-hexafluorobutyloxy, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethyloxy, 3,3,3-trifluoro-2-trifluoromethylpropyloxy, 2,2,3,3,4, 4,4-heptafluorobutyloxy, 3,3,4,4,4-pentafluoro-2-butyloxy, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyloxy, 1,1,2,2,3,3,4,4-octafluorobutyloxy, nonafluorobutyloxy, perfluoro-tert-butyloxy, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyloxy, 5,5,5-trifluoropentyloxy, 4,4,5,5,5-pentafluoropentyloxy, 3,3,4,4,5,5,5-heptafluoropentyl peroxy, 3,3,4,4,5,5,5-heptafluoro-2-pentyloxy, 2,2,3,3,4,4,5,5,5-nonafluoropentyloxy, 2,2,3,3,4,4,5,5,5-octafluoropentyloxy, perfluoropentyloxy, 4,4,5,5,5-pentafluoro-2-butyloxy, 2,2-bis(trifluoromethyl)propyloxy, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxy, 3,3,4,4,5,5,6,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,Examples of such groups include 6-heptafluorohexyloxy, 2,2,3,3,4,4,5,5,6,6-decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis(trifluoromethyl)butyloxy, and perfluorohexyloxy.

[0039] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkyloxy group" refers to a (C3 to C6 cycloalkyl)-O- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy groups.

[0040] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclyloxy group" refers to a (3- to 6-membered heterocyclyl)-O- group in which the heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridinyloxy, oxiranyloxy, oxetanyloxy, thietanyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, azetidinyloxy, pyrrolidinyloxy, piperidinyloxy, piperazinyloxy, dihydroisoxazolyloxy, dioxaborolanyloxy, dioxolanyloxy, dioxanyloxy, and morpholinyloxy groups.

[0041] In the present invention, "C6 to C 12 Unless otherwise specified, the term "aryloxy group" refers to a group in which the aryl moiety has the above meaning (C6 to C 12 aryl)-O- group, and examples thereof include phenyloxy, biphenyloxy, naphthalen-1-yloxy, and naphthalen-2-yloxy groups.

[0042] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryloxy group" refers to a (5- to 12-membered heteroaryl)-O- group in which the heteroaryl moiety has the above meaning, and examples thereof include pyridyloxy, pyrimidinyloxy, pyrazinyloxy, pyridazinyloxy, triazinyloxy, thienyloxy, furanyloxy, pyrrolyloxy, pyrazolyloxy, thiazolyloxy, isothiazolyloxy, oxazolyloxy, isoxazolyloxy, imidazolyloxy, triazolyloxy, thiadiazolyloxy, and oxadiazolyloxy. Examples of groups include zolyloxy, tetrazolyloxy, indolyloxy, benzimidazolyloxy, indazolyloxy, benzotriazolyloxy, isoquinolinyloxy, quinolinyloxy, benzothiazolyloxy, benzofuranyloxy, benzothienyloxy, benzisoxazolyloxy, pyrazolopyridyloxy, pyrazolopyrimidinyloxy, pyrrolopyridyloxy, triazolopyridyloxy, triazolopyrimidinyloxy, quinazolinyloxy, quinoxalinyloxy, and cinnolinyloxy.

[0043] In the present invention, unless otherwise specified, the term "C1 to C6 alkylthio group" refers to a (C1 to C6 alkyl)-S- group in which the alkyl moiety has the above meaning, and examples thereof include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and tert-butylthio groups.

[0044] In the present invention, unless otherwise specified, the term "C1 to C6 haloalkylthio group" refers to a (C1 to C6 haloalkyl)-S- group in which the haloalkyl moiety has the above meaning, and examples thereof include fluoromethylthio, difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio, and 4,4,4-trifluorobutylthio.

[0045] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkylthio group" refers to a (C3 to C6 cycloalkyl)-S- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropylthio, cyclobutylthio, cyclopentylthio, and cyclohexylthio groups.

[0046] In the present invention, unless otherwise specified, the term "C1-C6 alkylsulfinyl group" refers to a (C1-C6 alkyl)-S(=O)- group in which the alkyl moiety has the above meaning, and examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl.

[0047] In the present invention, unless otherwise specified, the term "C1-C6 haloalkylsulfinyl group" refers to a (C1-C6 haloalkyl)-S(=O)- group in which the haloalkyl moiety has the above meaning, and examples thereof include difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl, and heptafluoro-2-propylsulfinyl.

[0048] In the present invention, unless otherwise specified, the term "C3-C6 cycloalkylsulfinyl group" refers to a (C3-C6 cycloalkyl)-S(=O)- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, and cyclohexylsulfinyl groups.

[0049] In the present invention, unless otherwise specified, the term "C1-C6 alkylsulfonyl group" refers to a (C1-C6 alkyl)-S(=O)2- group in which the alkyl moiety has the above meaning, and examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, and tert-butylsulfonyl groups.

[0050] In the present invention, unless otherwise specified, the term "C1-C6 haloalkylsulfonyl group" refers to a (C1-C6 haloalkyl)-S(=O)2- group in which the haloalkyl moiety has the above meaning, and examples thereof include difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, and heptafluoro-2-propylsulfonyl groups.

[0051] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkylsulfonyl group" refers to a (C3 to C6 cycloalkyl)-S(=O)2- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, and cyclohexylsulfonyl groups.

[0052] In the present invention, unless otherwise specified, the term "hydroxy C1-C6 alkyl group" refers to a hydroxy-(C1-C6 alkyl)- group in which the alkyl moiety has the above meaning, and examples thereof include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxypropan-2-yl, 3-hydroxy-2-methylpropan-2-yl, 4-hydroxy-2-methylbutan-2-yl, and 5-hydroxy-2-methylpentan-2-yl.

[0053] In the present invention, unless otherwise specified, the term "cyano C1-C6 alkyl group" refers to a (cyano)-(C1-C6 alkyl)- group in which the alkyl moiety has the above meaning, and examples thereof include cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyano-2-propyl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl, and 6-cyanohexyl.

[0054] In the present invention, unless otherwise specified, "C1-C6 alkyloxy C1-C6 alkyl group" refers to a (C1-C6 alkyl)-O-(C1-C6 alkyl)- group in which the alkyloxy moiety and the alkyl moiety have the above-mentioned meanings, and examples thereof include methoxymethyl, ethyloxymethyl, n-propyloxymethyl, isopropyloxymethyl, tert-butyloxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, 1-ethyloxyethyl, 2-ethyloxyethyl, 1-isopropyloxyethyl, 1-methoxypropyl, 2-methoxypropyl, 1-ethyloxypropyl, 1-methoxybutyl, and 1-ethyloxybutyl groups.

[0055] In the present invention, unless otherwise specified, the term "C1-C6 haloalkyloxy C1-C6 alkyl group" refers to a (C1-C6 haloalkyl)-O-(C1-C6 alkyl)- group in which the haloalkyloxy moiety and alkyl moiety have the above-mentioned meanings, and examples thereof include 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethyloxy)ethyl, 2-(2,2,2-trifluoroethyloxy)ethyl, and 2-(3,3-difluoropropiooxy)ethyl. , 2-(3,3,3-trifluoropropioxy)ethyl, 3-(difluoromethoxy)propyl, 3-(trifluoromethoxy)propyl, 3-(2,2-difluoroethyloxy)propyl, 3-(2,2,2-trifluoroethyloxy)propyl, 3-(3,3-difluoropropioxy)propyl, 3-(3,3,3-trifluoropropioxy)propyl, 4-(trifluoromethoxy)butyl, or 5-(trifluoromethoxy)pentyl groups.

[0056] In the present invention, unless otherwise specified, a "C3-C6 cycloalkyloxy C1-C6 alkyl group" refers to a (C3-C6 cycloalkyl)-O-(C1-C6 alkyl)- group in which the cycloalkyloxy moiety and alkyl moiety are as defined above, and examples thereof include cyclopropyloxymethyl, 1-cyclopropyloxyethyl, 2-cyclopropyloxyethyl, 1-cyclopropyloxypropan-2-yl, 2-cyclopropyloxypropyl, cyclobutyloxymethyl, 1-cyclobutyloxyethyl, 2-cyclobutyloxyethyl, 1-cyclobutyloxypropan-2-yl, 2-cyclobutyloxypropyl, cyclopentyloxymethyl, 1-cyclopentyloxyethyl, 2-cyclopentyloxyethyl, 1-cyclopentyloxypropan-2-yl, 2-cyclopentyloxypropyl, cyclohexyloxymethyl, 1-cyclohexyloxyethyl, 2-cyclohexyloxyethyl, 1-cyclohexyloxypropan-2-yl, or 2-cyclohexyloxypropyl.

[0057] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclyloxy C1-C6 alkyl group" refers to a (3- to 6-membered heterocyclyl)-O-(C1-C6 alkyl)- group in which the heterocyclyloxy moiety and the alkyl moiety have the above-mentioned meanings, and examples thereof include (aziridinyloxy)methyl, 1-(aziridinyloxy)ethyl, 2-(aziridinyloxy)ethyl, (oxiranyloxy)methyl, 1-(oxiranyloxy)ethyl, 2-(oxiranyloxy)ethyl, (oxetanyloxy)methyl, 1-(aziridinyloxy)ethyl ... -(Oxetanyloxy)ethyl, 2-(Oxetanyloxy)ethyl, (thietanyloxy)methyl, 1-(thietanyloxy)ethyl, 2-(thietanyloxy)ethyl, (tetrahydrofuranyloxy)methyl, 1-(tetrahydrofuranyloxy)ethyl, 2-(tetrahydrofuranyloxy)ethyl, (tetrahydropyranyloxy)methyl, 1-(tetrahydropyranyloxy)ethyl, 2-(tetrahydropyranyloxy)ethyl, (azetidinyloxy)methyl, 1-(azetidinyloxy) )ethyl, 2-(azetidinyloxy)ethyl, (pyrrolidinyloxy)methyl, 1-(pyrrolidinyloxy)ethyl, 2-(pyrrolidinyloxy)ethyl, (piperidinyloxy)methyl, 1-(piperidinyloxy)ethyl, 2-(piperidinyloxy)ethyl, (piperazinyloxy)methyl, 1-(piperazinyloxy)ethyl, 2-(piperazinyloxy)ethyl, (dihydroisoxazolyloxy)methyl, 1-(dihydroisoxazolyloxy)ethyl, 2-(dihydroisoxazolyloxy) )ethyl, (dioxaborolanyloxy)methyl, 1-(dioxaborolanyloxy)ethyl, 2-(dioxaborolanyloxy)ethyl, (dioxolanyloxy)methyl, 1-(dioxolanyloxy)ethyl, 2-(dioxolanyloxy)ethyl, (dioxanyloxy)methyl, 1-(dioxanyloxy)ethyl, 2-(dioxolanyloxy)ethyl, (dioxanyloxy)methyl, 1-(dioxanyloxy)ethyl, 2-(dioxanyloxy)ethyl, (morpholinyloxy)methyl, 1-(morpholinyloxy)ethyl, or 2-(morpholinyloxy)ethyl groups can be mentioned.

[0058] In the present invention, "C6 to C 12Unless otherwise specified, the term "aryloxy C1-C6 alkyl group" refers to a group in which the aryloxy moiety and alkyl moiety have the same meaning as defined above (C6-C 12 and aryl)-O-(C1-C6 alkyl)- groups, and examples thereof include phenyloxymethyl, 1-phenyloxyethyl, 2-phenyloxyethyl, 1-phenyloxypropan-2-yl, 2-phenyloxypropyl, biphenyloxymethyl, 1-biphenyloxyethyl, 2-biphenyloxyethyl, 1-biphenyloxypropan-2-yl, 2-biphenyloxypropyl, naphthalen-1-yloxymethyl, 1-(naphthalen-1-yloxy)ethyl, 2-(naphthalen-1-yloxy)ethyl, 1-(naphthalen-1-yloxy)propan-2-yl, 2-(naphthalen-1-yloxy)propyl, naphthalen-2-yloxymethyl, 1-(naphthalen-2-yloxy)ethyl, 2-(naphthalen-2-yloxy)ethyl, 1-(naphthalen-2-yloxy)propan-2-yl, and 2-(naphthalen-2-yloxy)propyl groups.

[0059] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryloxy C1-C6 alkyl group" refers to a (5- to 12-membered heteroaryl)-O-(C1-C6 alkyl)- group in which the heteroaryloxy moiety and the alkyl moiety have the same meaning as above, and examples thereof include pyridyloxymethyl, 1-(pyridyloxy)ethyl, pyridyloxyethyl, 1-(pyridyloxy)propan-2-yl, pyrimidinyloxymethyl, 1-(pyrimidinyloxy)ethyl, pyrimidinyloxyethyl, 1-(pyrimidinyloxy)propan-2-yl, pyrazinyloxymethyl, 1-(pyrimidinyloxy)ethyl, pyrimidinyloxyethyl, 1-(pyrimidinyloxy)propan-2-yl, pyrazinyloxymethyl, 1-(pyrid ... 1-(pyridyloxy)propan-2-yl, pyrazinyloxymethyl, 1-(pyridyloxy)ethyl, 1-(pyridyloxy)propan-2-yl, pyrazinyloxymethyl, 1-(pyridyloxy)ethyl, 1-(pyridyloxy)propan-2-yl, pyrazinyloxymethyl, 1-(pyridyloxy)ethyl, 1- Dimethyl, 1-(pyrazinyloxy)ethyl, pyrazinyloxyethyl, 1-(pyrazinyloxy)propan-2-yl, pyridazinyloxymethyl, 1-(pyridazinyloxy)ethyl, pyridazinyloxyethyl, 1-(pyridazinyloxy)propan-2-yl, triazinyloxymethyl, 1-(triazinyloxy)ethyl, triazinyloxyethyl, 1-(triazinyloxy)propan-2-yl, thienyloxymethyl, 1-(thienyloxy)ethyl, thienyloxyethyl, 1-(thienyloxy)propan-2-yl, phenyl Ranyloxymethyl, 1-(furanyloxy)ethyl, furanyloxyethyl, 1-(furanyloxy)propan-2-yl, pyrrolyloxymethyl, 1-(pyrrolyloxy)ethyl, pyrrolyloxyethyl, 1-(pyrrolyloxy)propan-2-yl, pyrazolyloxymethyl, 1-(pyrazolyloxy)ethyl, pyrazolyloxyethyl, 1-(pyrazolyloxy)propan-2-yl, thiazolyloxymethyl, 1-(thiazolyloxy)ethyl, thiazolyloxyethyl, 1-(thiazolyloxy)propan-2-yl, isothiazolyl oxymethyl, 1-(isothiazolyloxy)ethyl, isothiazolyloxyethyl, 1-(isothiazolyloxy)propan-2-yl, oxazolyloxymethyl, 1-(oxazolyloxy)ethyl, oxazolyloxyethyl, 1-(oxazolyloxy)propan-2-yl, isoxazolyloxymethyl, 1-(isoxazolyloxy)ethyl, isoxazolyloxyethyl, 1-(isoxazolyloxy)propan-2-yl, imidazolyloxymethyl, 1-(imidazolyloxy)ethyl, imidazolyloxyethyl,1-(imidazolyloxy)propan-2-yl, triazolyloxymethyl, 1-(triazolyloxy)ethyl, triazolyloxyethyl, 1-(triazolyloxy)propan-2-yl, thiadiazolyloxymethyl, 1-(thiadiazolyloxy)ethyl, thiadiazolyloxyethyl, 1-(thiadiazolyloxy)propan-2-yl, oxadiazolyloxymethyl, 1-(oxadiazolyl)oxyethyl, oxadiazolyloxyethyl, 1-(oxadiazolyloxy)propan-2-yl, tetrazolyloxymethyl, 1-(tetrazolyloxy)ethyl, tetrazolyloxyethyl, 1-(tetrazolyloxy)propan-2-yl, indolyloxymethyl, 1-(indolyloxy)ethyl, indolyloxyethyl, 1-(indolyloxy)propan-2-yl, benzimidazolyloxymethyl, 1-(benzimidazolyloxy)ethyl, benzimidazolyloxyethyl, 1-(benzimidazolyloxy)propan-2-yl, indazolyloxymethyl, 1-(indazolyloxy)ethyl, indazolyloxyethyl, 1-(indazolyloxy) 1-(benzotriazolyloxy)propan-2-yl, benzotriazolyloxymethyl, 1-(benzotriazolyloxy)ethyl, benzotriazolyloxyethyl, 1-(benzotriazolyloxy)propan-2-yl, isoquinolinyloxymethyl, 1-(isoquinolinyloxy)ethyl, isoquinolinyloxyethyl, 1-(isoquinolinyloxy)propan-2-yl, quinolinyloxymethyl, 1-(quinolinyloxy)ethyl, quinolinyloxyethyl, 1-(quinolinyloxy)propan-2-yl, benzothiazolyloxymethyl, 1-(benzothiazolyl) (benzothienyloxy)ethyl, benzothiazolyloxyethyl, 1-(benzothiazolyloxy)propan-2-yl, benzofuranyloxymethyl, 1-(benzofuranyloxy)ethyl, benzofuranyloxyethyl, 1-(benzofuranyloxy)propan-2-yl, benzothienyloxymethyl, 1-(benzothienyloxy)ethyl, benzothienyloxyethyl, 1-(benzothienyloxy)propan-2-yl, benzisoxazolyloxymethyl, 1-(benzisoxazolyloxy)ethyl, benzisoxazolyloxyethyl,Examples of such groups include 1-(benzoisoxazolyloxy)propan-2-yl, quinazolinyloxymethyl, 1-(quinazolinyloxy)ethyl, quinazolinyloxyethyl, 1-(quinazolinyloxy)propan-2-yl, quinoxalinyloxymethyl, 1-(quinoxalinyloxy)ethyl, quinoxalinyloxyethyl, 1-(quinoxalinyloxy)propan-2-yl, cinnolinyloxymethyl, 1-(cinnolinyloxy)ethyl, cinnolinyloxyethyl, and 1-(cinnolinyloxy)propan-2-yl.

[0060] In the present invention, unless otherwise specified, the term "C1-C6 alkylamino C1-C6 alkyl group" refers to a (C1-C6 alkyl)-NH-(C1-C6 alkyl)- group in which the alkylamino moiety and the alkyl moiety have the above-mentioned meanings, and examples thereof include (methylamino)methyl, (ethylamino)methyl, (isopropylamino)methyl, (tert-butylamino)methyl, 1-(methylamino)ethyl, and 2-(methylamino)ethyl groups.

[0061] In the present invention, unless otherwise specified, the term "C3-C6 cycloalkylamino C1-C6 alkyl group" refers to a (C3-C6 cycloalkyl)-NH-(C1-C6 alkyl)- group in which the cycloalkylamino moiety and alkyl moiety have the above-mentioned meanings, and examples thereof include (cyclopropylamino)methyl, (cyclobutylamino)methyl, 1-(cyclopropylamino)ethyl, and 2-(cyclopropylamino)ethyl groups.

[0062] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylamino C1-C6 alkyl group" refers to a (3- to 6-membered heterocyclyl)-NH-(C1-C6 alkyl)- group in which the heterocyclylamino moiety and the alkyl moiety have the above-mentioned meanings, and examples thereof include (aziridinylamino)methyl, 1-(aziridinylamino)ethyl, 2-(aziridinylamino)ethyl, (oxiranylamino)methyl, 1-(oxiranylamino)ethyl, 2-(oxiranylamino)ethyl, (oxetanylamino)methyl, 1 -(oxetanylamino)ethyl, 2-(oxetanylamino)ethyl, (thietanylamino)methyl, 1-(thietanylamino)ethyl, 2-(thietanylamino)ethyl, (tetrahydrofuranylamino)methyl, 1-(tetrahydrofuranylamino)ethyl, 2-(tetrahydrofuranylamino)ethyl, (tetrahydropyranylamino)methyl, 1-(tetrahydropyranylamino)ethyl, 2-(tetrahydropyranylamino)ethyl, (azetidinylamino)methyl, 1-(azetidinylamino) )ethyl, 2-(azetidinylamino)ethyl, (pyrrolidinylamino)methyl, 1-(pyrrolidinylamino)ethyl, 2-(pyrrolidinylamino)ethyl, (piperidinylamino)methyl, 1-(piperidinylamino)ethyl, 2-(piperidinylamino)ethyl, (piperazinylamino)methyl, 1-(piperazinylamino)ethyl, 2-(piperazinylamino)ethyl, (dihydroisoxazolylamino)methyl, 1-(dihydroisoxazolylamino)ethyl, 2-(dihydroisoxazolylamino) )ethyl, (dioxaborolanylamino)methyl, 1-(dioxaborolanylamino)ethyl, 2-(dioxaborolanylamino)ethyl, (dioxolanylamino)methyl, 1-(dioxolanylamino)ethyl, 2-(dioxolanylamino)ethyl, (dioxanylamino)methyl, 1-(dioxanylamino)ethyl, 2-(dioxanylamino)ethyl, (dioxanylamino)methyl, 1-(dioxanylamino)ethyl, 2-(dioxanylamino)ethyl, (morpholinylamino)methyl, 1-(morpholinylamino)ethyl, or 2-(morpholinylamino)ethyl groups can be mentioned.

[0063] In the present invention, "C6 to C 12Unless otherwise specified, the term "arylamino C1-C6 alkyl group" refers to a group in which the arylamino moiety and alkyl moiety have the same meanings as defined above (C6-C 12 and represents a (C1-C6 alkyl)- group, and examples thereof include phenylaminomethyl, 1-(phenylamino)ethyl, 2-(phenylamino)ethyl, biphenylaminomethyl, 1-(biphenylamino)ethyl, 2-(biphenylamino)ethyl, naphthalen-1-ylaminomethyl, 1-(naphthalen-1-ylamino)ethyl, 2-(naphthalen-1-ylamino)ethyl, naphthalen-2-ylaminomethyl, 1-(naphthalen-2-ylamino)ethyl, and 2-(naphthalen-2-ylamino)ethyl groups.

[0064] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylamino C1-C6 alkyl group" refers to a (5- to 12-membered heteroaryl)-NH-(C1-C6 alkyl)- group in which the heteroarylamino moiety and the alkyl moiety have the above-mentioned meanings, and examples thereof include pyridylaminomethyl, 1-(pyridylamino)ethyl, pyridylaminoethyl, 1-(pyridylamino)propan-2-yl, pyrimidinylaminomethyl, 1-(pyrimidinylamino)ethyl, pyrimidinylaminoethyl, 1-(pyrimidinylamino)propan-2-yl, pyrazinylamido ... aminomethyl, 1-(pyrazinylamino)ethyl, pyrazinylaminoethyl, 1-(pyrazinylamino)propan-2-yl, pyridazinylaminomethyl, 1-(pyridazinylamino)ethyl, pyridazinylaminoethyl, 1-(pyridazinylamino)propan-2-yl, triazinylaminomethyl, 1-(triazinylamino)ethyl, triazinylaminoethyl, 1-(triazinylamino)propan-2-yl, thienylaminomethyl, 1-(thienylamino)ethyl, thienylaminoethyl, 1-(thienylamino)propan-2-yl, Furanylaminomethyl, 1-(furanylamino)ethyl, furanylaminoethyl, 1-(furanylamino)propan-2-yl, pyrrolylaminomethyl, 1-(pyrrolylamino)ethyl, pyrrolylaminoethyl, 1-(pyrrolylamino)propan-2-yl, pyrazolylaminomethyl, 1-(pyrazolylamino)ethyl, pyrazolylaminoethyl, 1-(pyrazolylamino)propan-2-yl, thiazolylaminomethyl, 1-(thiazolylamino)ethyl, thiazolylaminoethyl, 1-(thiazolylamino)propan-2-yl, isothiazolyl aminomethyl, 1-(isothiazolylamino)ethyl, isothiazolylaminoethyl, 1-(isothiazolylamino)propan-2-yl, oxazolylaminomethyl, 1-(oxazolylamino)ethyl, oxazolylaminoethyl, 1-(oxazolylamino)propan-2-yl, isoxazolylaminomethyl, 1-(isoxazolylamino)ethyl, isoxazolylaminoethyl, 1-(isoxazolylamino)propan-2-yl, imidazolylaminomethyl, 1-(imidazolylamino)ethyl, imidazolylaminoethyl1-(imidazolylamino)propan-2-yl, triazolylaminomethyl, 1-(triazolylamino)ethyl, triazolylaminoethyl, 1-(triazolylamino)propan-2-yl, thiadiazolylaminomethyl, 1-thiadiazolylaminoethyl, thiadiazolylaminoethyl, 1-(thiadiazolylamino)propan-2-yl, oxadiazolylaminomethyl, 1-(oxadiazolylamino)ethyl, oxadiazolylaminoethyl, 1-(oxadiazolylamino)propan-2-yl, tetrazolylaminomethyl, 1- (Tetrazolylamino)ethyl, Tetrazolylaminoethyl, 1-(tetrazolylamino)propan-2-yl, Indolylaminomethyl, 1-(indolylamino)ethyl, Indolylaminoethyl, 1-(indolylamino)propan-2-yl, Benzimidazolylaminomethyl, 1-(benzimidazolylamino)ethyl, Benzimidazolylaminoethyl, 1-(benzimidazolylamino)propan-2-yl, Indazolylaminomethyl, 1-(indazolylamino)ethyl, Indazolylaminoethyl, 1-(indazolylamino )propan-2-yl, benzotriazolylaminomethyl, 1-(benzotriazolylamino)ethyl, benzotriazolylaminoethyl, 1-(benzotriazolylamino)propan-2-yl, isoquinolinylaminomethyl, 1-(isoquinolinylamino)ethyl, isoquinolinylaminoethyl, 1-(isoquinolinylamino)propan-2-yl, quinolinylaminomethyl, 1-(quinolinylamino)ethyl, quinolinylaminoethyl, 1-(quinolinylamino)propan-2-yl, benzothiazolylaminomethyl, 1-(benzothiazoly benzothienylaminomethyl, 1-(benzothienylamino)ethyl, benzothiazolylaminoethyl, 1-(benzothiazolylamino)propan-2-yl, benzofuranylaminomethyl, 1-(benzofuranylamino)ethyl, benzofuranylaminoethyl, 1-(benzofuranylamino)propan-2-yl, benzothienylaminomethyl, 1-(benzothienylamino)ethyl, benzothienylaminoethyl, 1-(benzothienylamino)propan-2-yl, benzisoxazolylaminomethyl, 1-(benzisoxazolylamino)ethyl, benzisoxazolylaminoethyl,Examples of such groups include 1-(benzoisoxazolylamino)propan-2-yl, quinazolinylaminomethyl, 1-(quinazolinylamino)ethyl, quinazolinylaminoethyl, 1-(quinazolinylamino)propan-2-yl, quinoxalinylaminomethyl, 1-(quinoxalinylamino)ethyl, quinoxalinylaminoethyl, 1-(quinoxalinylamino)propan-2-yl, cinnolinylaminomethyl, 1-(cinnolinylamino)ethyl, cinnolinylaminoethyl, and 1-(cinnolinylamino)propan-2-yl.

[0065] In the present invention, unless otherwise specified, "C1-C6 alkylthio C1-C6 alkyl group" refers to a (C1-C6 alkyl)-S-(C1-C6 alkyl)- group in which the alkylthio moiety and alkyl moiety have the above-mentioned meanings, and examples thereof include 1-methylthio-1-methylethyl, 1-ethylthio-1-methylethyl, 1-n-propylthio-1-methylethyl, 1-isopropylthio-1-methylethyl, 3-methylthio-2-methylpropan-2-yl, 3-ethylthio-2-methylpropan-2-yl, 3-n-propylthio-2-methylpropan-2-yl, and 3-isopropylthio-2-methylpropan-2-yl groups.

[0066] In the present invention, unless otherwise specified, a "C1-C6 haloalkylthio C1-C6 alkyl group" refers to a (C1-C6 haloalkyl)-S-(C1-C6 alkyl)- group in which the haloalkylthio moiety and the alkyl moiety are as defined above, and examples thereof include (difluoromethylthio)methyl, (trifluoromethylthio)methyl, (2,2-difluoroethylthio)methyl, (2,2,2-trifluoroethylthio)methyl, 2-(difluoromethylthio)ethyl, 2-(trifluoromethylthio)ethyl, 2-(2,2-difluoroethylthio)ethyl, 2-(2,2,2-trifluoroethylthio)ethyl, 3-(difluoromethylthio)propyl, 3-(trifluoromethylthio)propyl, 3-(2,2-difluoroethylthio)propyl, and 3-(2,2,2-trifluoroethylthio)propyl.

[0067] In the present invention, unless otherwise specified, a "C3-C6 cycloalkylthio C1-C6 alkyl group" refers to a (C1-C6 cycloalkyl)-S-(C1-C6 alkyl)- group in which the cycloalkylthio moiety and the alkyl moiety have the above-mentioned meanings, and examples thereof include (cyclopropylthio)methyl, (cyclobutylthio)methyl, (cyclopentylthio)methyl, (cyclohexylthio)methyl, (cyclooctylthio)methyl, 1-(cyclopropylthio)ethyl, and 2-(cyclopropylthio)ethyl groups.

[0068] In the present invention, unless otherwise specified, "C1-C6 alkylsulfinyl C1-C6 alkyl group" refers to a (C1-C6 alkyl)-S(=O)-(C1-C6 alkyl)- group in which the alkylsulfinyl moiety and the alkyl moiety are as defined above, and examples thereof include 1-methylsulfinyl-1-methylethyl, 1-ethylsulfinyl-1-methylethyl, 1-n-propylsulfinyl-1-methylethyl, 1-isopropylsulfinyl-1-methylethyl, 3-methylsulfinyl-2-methylpropan-2-yl, 3-ethylsulfinyl-2-methylpropan-2-yl, 3-n-propylsulfinyl-2-methylpropan-2-yl, and 3-isopropylsulfinyl-2-methylpropan-2-yl.

[0069] In the present invention, unless otherwise specified, a "C1-C6 haloalkylsulfinyl C1-C6 alkyl group" refers to a (C1-C6 haloalkyl)-S(=O)-(C1-C6 alkyl)- group in which the haloalkylsulfinyl moiety and the alkyl moiety are as defined above, and examples thereof include difluoromethylsulfinyl)methyl, (trifluoromethylsulfinyl)methyl, (2,2-difluoroethylsulfinyl)methyl, (2,2,2-trifluoroethylsulfinyl)methyl, 2-(difluoromethylsulfinyl)ethyl, 2-(trifluoromethylsulfinyl)ethyl, 2-(2,2-difluoroethylsulfinyl)ethyl, 2-(2,2,2-trifluoroethylsulfinyl)ethyl, 3-(difluoromethylsulfinyl)propyl, 3-(trifluoromethylsulfinyl)propyl, 3-(2,2-difluoroethylsulfinyl)propyl, and 3-(2,2,2-trifluoroethylsulfinyl)propyl groups.

[0070] In the present invention, unless otherwise specified, a "C3-C6 cycloalkylsulfinyl C1-C6 alkyl group" refers to a (C3-C6 cycloalkyl)-S(=O)-(C1-C6 alkyl)- group in which the cycloalkylsulfinyl moiety and the alkyl moiety are as defined above, and examples thereof include (cyclopropylsulfinyl)methyl, (cyclobutylsulfinyl)methyl, (cyclopentylsulfinyl)methyl, (cyclohexylsulfinyl)methyl, (cyclooctylsulfinyl)methyl, 1-(cyclopropylsulfinyl)ethyl, and 2-(cyclopropylsulfinyl)ethyl groups.

[0071] In the present invention, unless otherwise specified, "C1-C6 alkylsulfonyl C1-C6 alkyl group" refers to a (C1-C6 alkyl)-S(=O)2-(C1-C6 alkyl)- group in which the alkylsulfonyl moiety and the alkyl moiety are as defined above, and examples thereof include 1-methylsulfonyl-1-methylethyl, 1-ethylsulfonyl-1-methylethyl, 1-n-propylsulfonyl-1-methylethyl, 1-isopropylsulfonyl-1-methylethyl, 3-methylsulfonyl-2-methylpropan-2-yl, 3-ethylsulfonyl-2-methylpropan-2-yl, 3-n-propylsulfonyl-2-methylpropan-2-yl, and 3-isopropylsulfonyl-2-methylpropan-2-yl.

[0072] In the present invention, unless otherwise specified, a "C1-C6 haloalkylsulfonyl C1-C6 alkyl group" refers to a (C1-C6 haloalkyl)-S(=O)2-(C1-C6 alkyl)- group in which the haloalkylsulfonyl moiety and the alkyl moiety are as defined above, and examples thereof include (difluoromethylsulfonyl)methyl, (trifluoromethylsulfonyl)methyl, (2,2-difluoroethylsulfonyl)methyl, (2,2,2-trifluoroethylsulfonyl)methyl, 2-(difluoromethylsulfonyl)ethyl, 2-(trifluoromethylsulfonyl)ethyl, 2-(2,2-difluoroethylsulfonyl)ethyl, 2-(2,2,2-trifluoroethylsulfonyl)ethyl, 3-(difluoromethylsulfonyl)propyl, 3-(trifluoromethylsulfonyl)propyl, 3-(2,2-difluoroethylsulfonyl)propyl, and 3-(2,2,2-trifluoroethylsulfonyl)propyl groups.

[0073] In the present invention, unless otherwise specified, the term "C3-C6 cycloalkylsulfonyl C1-C6 alkyl group" refers to a (C3-C6 cycloalkyl)-S(=O)2-(C1-C6 alkyl)- group in which the cycloalkylsulfonyl moiety and the alkyl moiety are as defined above, and examples thereof include (cyclopropylsulfonyl)methyl, (cyclobutylsulfonyl)methyl, (cyclopentylsulfonyl)methyl, (cyclohexylsulfonyl)methyl, (cyclooctylsulfonyl)methyl, 1-(cyclopropylsulfonyl)ethyl, and 2-(cyclopropylsulfonyl)ethyl groups.

[0074] In the present invention, unless otherwise specified, the term "C1 to C6 alkyloxycarbonyl group" refers to a (C1 to C6 alkyl)-OC(=O)- group in which the alkyloxy moiety has the above meaning, and examples thereof include methyloxycarbonyl, ethyloxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, 1-methylbutyloxycarbonyl, 2-methylbutyloxycarbonyl, 3-methylbutyloxycarbonyl, 1-ethylpropyloxycarbonyl, 1,1-dimethylpropyloxycarbonyl, 1,2-dimethylpropyloxycarbonyl, and 2,2-dimethylpropyloxycarbonyl.

[0075] In the present invention, unless otherwise specified, the term "C1-C6 haloalkyloxycarbonyl group" refers to a (C1-C6 haloalkyl)-OC(=O) group in which the haloalkyloxy moiety has the above meaning, and examples thereof include difluoromethyloxycarbonyl, dichloromethyloxycarbonyl, trifluoromethyloxycarbonyl, trichloromethyloxycarbonyl, tribromomethyloxycarbonyl, chlorodifluoromethyloxycarbonyl, bromodifluoromethyloxycarbonyl, 2-fluoroethyloxycarbonyl, 1-chloroethyloxycarbonyl, 2-chloroethyloxycarbonyl, 1 ... ethyloxycarbonyl, 2-chloroethyloxycarbonyl, 1-bromoethyloxycarbonyl, 2-bromoethyloxycarbonyl, 2,2-difluoroethyloxycarbonyl, 1,2-dichloroethyloxycarbonyl, 2,2-dichloroethyloxycarbonyl, 2,2,2-trifluoroethyloxycarbonyl, 2,2,2-trichloroethyloxycarbonyl, 1,1,2,2-tetrafluoroethyloxycarbonyl, pentafluoroethyloxycarbonyl, 2-bromo-2-chloroethyloxycarbonyl, 2-chloroethyloxycarbonyl 1-chloro-1,1,2,2-tetrafluoroethyloxycarbonyl, 1-chloropropyloxycarbonyl, 2-chloropropyloxycarbonyl, 3-chloropropyloxycarbonyl, 2-bromopropyloxycarbonyl, 3-bromopropyloxycarbonyl, 2-bromo-1-methylethyloxycarbonyl, 3-iodopropyloxycarbonyl, 2,3-dichloropropyloxycarbonyl, 2,3-dibromopropyloxycarbonyl, 3,3,3- Trifluoropropyloxycarbonyl, 3,3,3-trifluoro-2-propyloxycarbonyl, 3,3,3-trichloropropyloxycarbonyl, 3-bromo-3,3-difluoropropyloxycarbonyl, 2,2-difluoropropyloxycarbonyl, 3,3-dichloro-3-fluoropropyloxycarbonyl, 2,2,3,3-tetrafluoropropyloxycarbonyl, 1-bromo-3,3,3-trifluoropropyloxycarbonyl, 2,2,3,3,3-pentafluoropropyloxycarbonyl, 2,2,2-Trifluoro-1-trifluoromethylethyloxycarbonyl, heptafluoropropyloxycarbonyl, heptafluoro-2-propyloxycarbonyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyloxycarbonyl, 1,1,2,3,3,3-hexafluoropropyloxycarbonyl, 2-chlorobutyloxycarbonyl, 3-chlorobutyloxycarbonyl, 4-chlorobutyloxycarbonyl, 2-chloro-1,1-dimethylethyloxycarbonyl, 4-bromobutyloxycarbonyl, 3-bromo-2-methylethyloxycarbonyl ethylpropyloxycarbonyl, 2-bromo-1,1-dimethylethyloxycarbonyl, 2,2-dichloro-1,1-dimethylethyloxycarbonyl, 2-chloro-1-chloromethyl-2-methylethyloxycarbonyl, 4,4,4-trifluorobutyloxycarbonyl, 3,3,3-trifluoro-1-methylpropyloxycarbonyl, 3,3,3-trifluoro-2-methylpropyloxycarbonyl, 2,3,4-trichlorobutyloxycarbonyl, 2,2,2-trichloro-1,1-dimethylethyloxycarbonyl, 4-chloro-4 ,4-difluorobutyloxycarbonyl, 4,4-dichloro-4-fluorobutyloxycarbonyl, 4-bromo-4,4-difluorobutyloxycarbonyl, 2,4-dibromo-4,4-difluorobutyloxycarbonyl, 3,4-dichloro-3,4,4-trifluorobutyloxycarbonyl, 3,3-dichloro-4,4,4-trifluorobutyloxycarbonyl, 4-bromo-3,3,4,4-tetrafluorobutyloxycarbonyl, 4-bromo-3-chloro-3,4,4-trifluorobutyloxycarbonyl, 2,2,3,3,4, 4-Hexafluorobutyloxycarbonyl, 2,2,3,4,4,4-hexafluorobutyloxycarbonyl, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethyloxycarbonyl, 3,3,3-trifluoro-2-trifluoromethylpropyloxycarbonyl, 2,2,3,3,4,4,4-heptafluorobutyloxycarbonyl, 3,3,4,4,4-pentafluoro-2-butyloxycarbonyl, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyloxycarbonyl, 1,1,2,2,3,3,4,4-Octafluorobutyloxycarbonyl, nonafluorobutyloxycarbonyl, perfluoro-tert-butyloxycarbonyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyloxycarbonyl, 5,5,5-trifluoropentyloxycarbonyl, 4,4,5,5,5-pentafluoropentyloxycarbonyl, 3,3,4,4,5,5,5-heptafluoropentyloxycarbonyl, 3,3,4,4,5,5,5-heptafluoro-2-pentyloxycarbonyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyloxycarbonyl, 2,2,3,3,4,4,5,5-octafluoropentyloxycarbonyl, perf Examples of such groups include fluoropentyloxycarbonyl, 4,4,5,5,5-pentafluoro-2-butyloxycarbonyl, 2,2-bis(trifluoromethyl)propyloxycarbonyl, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxycarbonyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyloxycarbonyl, 4,4,5,5,6,6,6-heptafluorohexyloxycarbonyl, 2,2,3,3,4,4,5,5,6,6-decafluorohexyloxycarbonyl, 4,4,4-trifluoro-3,3-bis(trifluoromethyl)butyloxycarbonyl, and perfluorohexyloxycarbonyl.

[0076] In the present invention, unless otherwise specified, the term "C3 to C6 cycloalkyloxycarbonyl group" refers to a (C3 to C6 cycloalkyl)-OC(=O)- group in which the cycloalkyloxy moiety has the above meaning, and examples thereof include cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, and cyclohexyloxycarbonyl groups.

[0077] In the present invention, "C6 to C 12 Unless otherwise specified, the term "aryl C1-C6 alkyloxycarbonyl group" refers to a group in which the aryl moiety and alkyloxy moiety have the same meaning as defined above (C6-C 12aryl)-(C1-C6 alkyl)-OC(=O)- group, and examples thereof include benzyloxycarbonyl, 1-phenylethyloxycarbonyl, 2-phenylethyloxycarbonyl, 2-phenylpropyloxycarbonyl, 2-phenylbutyloxycarbonyl, 1-phenylpentyloxycarbonyl, naphthalen-1-ylmethyloxycarbonyl, and naphthalen-2-ylmethyloxycarbonyl groups.

[0078] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryl C1-C6 alkyloxycarbonyl group" refers to a (5- to 12-membered heteroaryl)-(C1-C6 alkyl)-OC(=O)- group in which the heteroaryl portion and the alkyloxy portion have the same meaning as above, and examples thereof include (pyridin-2-yl)methyloxycarbonyl, 1-(pyridin-2-yl)ethyloxycarbonyl, (pyridin-3-yl)methyloxycarbonyl, 1-(pyridin-3-yl)ethyloxycarbonyl, (pyridin-4-yl)methyloxycarbonyl, 1-(pyridin-4-yl)ethyloxycarbonyl, and the like. Pyridin-4-yl)ethyloxycarbonyl, (pyrimidin-2-yl)methyloxycarbonyl, 1-(pyrimidin-2-yl)ethyloxycarbonyl, (pyrimidin-4-yl)methyloxycarbonyl, 1-(pyrimidin-4-yl)ethyloxycarbonyl, (pyrimidin-5-yl)methyloxycarbonyl, 1-(pyrimidin-5-yl)ethyloxycarbonyl, (pyrazin-2-yl)methyloxycarbonyl, 1-(pyrazin-2-yl)ethyloxycarbonyl, (pyridazin-3-yl)methyloxycarbonyl, 1-( (pyridazin-3-yl)ethyloxycarbonyl, (pyridazin-4-yl)methyloxycarbonyl, 1-(pyridazin-4-yl)ethyloxycarbonyl, (1,2,3-triazin-2-yl)methyloxycarbonyl, 1-(1,2,3-triazin-2-yl)ethyloxycarbonyl, (thiophen-2-yl)methyloxycarbonyl, 1-(thiophen-2-yl)ethyloxycarbonyl, (thiophen-3-yl)methyloxycarbonyl, 1-(thiophen-3-yl)ethyloxycarbonyl, (thiophen-4-yl) methyloxycarbonyl, 1-(thiophen-4-yl)ethyloxycarbonyl, (furan-2-yl)methyloxycarbonyl, 1-(furan-2-yl)ethyloxycarbonyl, (furan-3-yl)methyloxycarbonyl, 1-(furan-3-yl)ethyloxycarbonyl, (furan-4-yl)methyloxycarbonyl, 1-(furan-4-yl)ethyloxycarbonyl, (pyrrol-2-yl)methyloxycarbonyl, 1-(pyrrol-2-yl)ethyloxycarbonyl, (pyrrol-3-yl)methyloxycarbonyl,1-(pyrrol-3-yl)ethyloxycarbonyl, (pyrrol-4-yl)methyloxycarbonyl, 1-(pyrrol-4-yl)ethyloxycarbonyl, (pyrazol-2-yl)methyloxycarbonyl, 1-(pyrazol-2-yl)ethyloxycarbonyl, (pyrazol-3-yl)methyloxycarbonyl, 1-(pyrazol-3-yl)ethyloxycarbonyl, (pyrazol-4-yl)methyloxycarbonyl, 1-(pyrazol-4-yl)ethyloxycarbonyl, (pyrazol-5-yl)methyloxycarbonyl , 1-(pyrazol-5-yl)ethyloxycarbonyl, (thiazol-2-yl)methyloxycarbonyl, 1-(thiazol-2-yl)ethyloxycarbonyl, (thiazol-4-yl)methyloxycarbonyl, 1-(thiazol-4-yl)ethyloxycarbonyl, (thiazol-5-yl)methyloxycarbonyl, 1-(thiazol-5-yl)ethyloxycarbonyl, (isothiazol-3-yl)methyloxycarbonyl, 1-(isothiazol-3-yl)ethyloxycarbonyl, (isothiazol-4-yl)methyl oxycarbonyl, 1-(isothiazol-4-yl)ethyloxycarbonyl, (isothiazol-5-yl)methyloxycarbonyl, 1-(isothiazol-5-yl)ethyloxycarbonyl, (oxazol-2-yl)methyloxycarbonyl, 1-(oxazol-2-yl)ethyloxycarbonyl, (oxazol-4-yl)methyloxycarbonyl, 1-(oxazol-4-yl)ethyloxycarbonyl, (oxazol-5-yl)methyloxycarbonyl, 1-(oxazol-5-yl)ethyloxycarbonyl yl, (isoxazol-3-yl)methyloxycarbonyl, 1-(isoxazol-3-yl)ethyloxycarbonyl, (isoxazol-4-yl)methyloxycarbonyl, 1-(isoxazol-4-yl)ethyloxycarbonyl, (isoxazol-5-yl)methyloxycarbonyl, 1-(isoxazol-5-yl)ethyloxycarbonyl, (imidazol-2-yl)methyloxycarbonyl, 1-(imidazol-2-yl)ethyloxycarbonyl, (imidazol-3-yl)methyloxycarbonyl,1-(imidazol-3-yl)ethyloxycarbonyl, (imidazol-4-yl)methyloxycarbonyl, 1-(imidazol-4-yl)ethyloxycarbonyl, (imidazol-5-yl)methyloxycarbonyl, 1-(imidazol-5-yl)ethyloxycarbonyl, (1,2,3-triazol-1-yl)methyloxycarbonyl, 1-(1,2,3-triazol-1-yl)ethyloxycarbonyl, (1,2,3-triazol-2-yl)methyloxycarbonyl, 1-(1,2,3-triazol-2-yl)ethyl Oxycarbonyl, (1,2,3-triazol-3-yl)methyloxycarbonyl, 1-(1,2,3-triazol-3-yl)ethyloxycarbonyl, (1,2,3-triazol-4-yl)methyloxycarbonyl, 1-(1,2,3-triazol-4-yl)ethyloxycarbonyl, (1,2,3-triazol-5-yl)methyloxycarbonyl, 1-(1,2,3-triazol-5-yl)ethyloxycarbonyl, (1,2,4-triazol-1-yl)methyloxycarbonyl, 1-(1,2,4-triazol-1-yl)methyloxycarbonyl 1-(1,2,4-triazol-2-yl)ethyloxycarbonyl, (1,2,4-triazol-2-yl)ethyloxycarbonyl, (1,2,4-triazol-3-yl)methyloxycarbonyl, 1-(1,2,4-triazol-3-yl)ethyloxycarbonyl, (1,2,4-triazol-4-yl)methyloxycarbonyl, 1-(1,2,4-triazol-4-yl)ethyloxycarbonyl, (1,2,4-triazol-5-yl)methyloxycarbonyl, 1-(1,2,4-triazol-5-yl)methyloxycarbonyl, (1,2,3-thiadiazol-5-yl)ethyloxycarbonyl, (1,2,3-thiadiazol-4-yl)methyloxycarbonyl, 1-(1,2,3-thiadiazol-4-yl)ethyloxycarbonyl, (1,2,3-thiadiazol-5-yl)methyloxycarbonyl, 1-(1,2,3-thiadiazol-5-yl)ethyloxycarbonyl, (1,2,4-thiadiazol-3-yl)methyloxycarbonyl, 1-(1,2,4-thiadiazol-3-yl)ethyloxycarbonyl, (1,2,4-thiadiazol-5-yl)methyloxycarbonyl,1-(1,2,4-thiadiazol-5-yl)ethyloxycarbonyl, (1,2,5-thiadiazol-3-yl)methyloxycarbonyl, 1-(1,2,5-thiadiazol-3-yl)ethyloxycarbonyl, (1,2,5-thiadiazol-4-yl)methyloxycarbonyl, 1-(1,2,5-thiadiazol-4-yl)ethyloxycarbonyl, (1,3,4-thiadiazol-2-yl)methyloxycarbonyl, 1-(1,3,4-thiadiazol-2-yl)ethyloxycarbonyl, (1,3,4-thiadiazol-5- (1,2,3-oxadiazol-4-yl)methyloxycarbonyl, 1-(1,2,3-oxadiazol-4-yl)ethyloxycarbonyl, (1,2,3-oxadiazol-5-yl)methyloxycarbonyl, 1-(1,2,3-oxadiazol-5-yl)ethyloxycarbonyl, (1,2,4-oxadiazol-3-yl)methyloxycarbonyl, 1-(1,2,4-oxadiazol-3-yl)ethyloxycarbonyl bonyl, (1,2,4-oxadiazol-5-yl)methyloxycarbonyl, 1-(1,2,4-oxadiazol-5-yl)ethyloxycarbonyl, (1,2,5-oxadiazol-3-yl)methyloxycarbonyl, 1-(1,2,5-oxadiazol-3-yl)ethyloxycarbonyl, (1,2,5-oxadiazol-4-yl)methyloxycarbonyl, 1-(1,2,5-oxadiazol-4-yl)ethyloxycarbonyl, (1,3,4-oxadiazol-2-yl)methyloxycarbonyl, 1-(1,3,4 -oxadiazol-2-yl)ethyloxycarbonyl, (1,3,4-oxadiazol-5-yl)methyloxycarbonyl, 1-(1,3,4-oxadiazol-5-yl)ethyloxycarbonyl, (tetrazol-1-yl)methyloxycarbonyl, 1-(tetrazol-1-yl)ethyloxycarbonyl, (tetrazol-5-yl)methyloxycarbonyl, 1-(tetrazol-5-yl)ethyloxycarbonyl, (indol-1-yl)methyloxycarbonyl, 1-(indol-1-yl)ethyloxycarbonyl,(indol-2-yl)methyloxycarbonyl, 1-(indol-2-yl)ethyloxycarbonyl, (indol-3-yl)methyloxycarbonyl, 1-(indol-3-yl)ethyloxycarbonyl, (indol-4-yl)methyloxycarbonyl, 1-(indol-4-yl)ethyloxycarbonyl, (indol-5-yl)methyloxycarbonyl, 1-(indol-5-yl)ethyloxycarbonyl, (indol-6-yl)methyloxycarbonyl oxycarbonyl, 1-(indol-6-yl)ethyloxycarbonyl, (indol-7-yl)methyloxycarbonyl, 1-(indol-7-yl)ethyloxycarbonyl, (benzimidazol-1-yl)methyloxycarbonyl, 1-(benzimidazol-1-yl)ethyloxycarbonyl, (benzimidazol-2-yl)methyloxycarbonyl, 1-(benzimidazol-2-yl)ethyloxycarbonyl, (benzimidazol-4-yl)ethyloxycarbonyl, -yl)methyloxycarbonyl, 1-(benzimidazol-4-yl)ethyloxycarbonyl, (benzimidazol-5-yl)methyloxycarbonyl, 1-(benzimidazol-5-yl)ethyloxycarbonyl, (benzimidazol-6-yl)methyloxycarbonyl, 1-(benzimidazol-6-yl)ethyloxycarbonyl, (benzimidazol-7-yl)methyloxycarbonyl, 1-(benzimidazol-7-yl)ethyloxy carbonyl, (indazol-1-yl)methyloxycarbonyl, 1-(indazol-1-yl)ethyloxycarbonyl, (indazol-3-yl)methyloxycarbonyl, 1-(indazol-3-yl)ethyloxycarbonyl, (indazol-4-yl)methyloxycarbonyl, 1-(indazol-4-yl)ethyloxycarbonyl, (indazol-5-yl)methyloxycarbonyl, 1-(indazol-5-yl)ethyloxycarbonyl, (indazol-6-yl)methyloxycarbonyl, 1-(indazol-6-yl)ethyloxycarbonyl, (indazol-7-yl)methyloxycarbonyl, 1-(indazol-7-yl)ethyloxycarbonyl, (benzotriazol-1-yl)methyloxycarbonyl, 1-(benzotriazol-1-yl)ethyloxycarbonyl, (benzotriazol-4-yl)methyloxycarbonyl, 1-(benzotriazol-4-yl)ethyloxycarbonyl, (benzotriazol-5-yl)methyloxycarbonyl, 1 -(benzotriazol-5-yl)ethyloxycarbonyl, (benzotriazol-6-yl)methyloxycarbonyl, 1-(benzotriazol-6-yl)ethyloxycarbonyl, (benzotriazol-7-yl)methyloxycarbonyl, 1-(benzotriazol-7-yl)ethyloxycarbonyl, (isoquinolin-1-yl)methyloxycarbonyl, 1-(isoquinolin-1-yl)ethyloxycarbonyl, (isoquinolin-3-yl)methyloxycarbonyl, 1-(isoquinolin-3-yl)ethyloxycarbonyl, ( (isoquinolin-4-yl)methyloxycarbonyl, 1-(isoquinolin-4-yl)ethyloxycarbonyl, (isoquinolin-5-yl)methyloxycarbonyl, 1-(isoquinolin-5-yl)ethyloxycarbonyl, (isoquinolin-6-yl)methyloxycarbonyl, 1-(isoquinolin-6-yl)ethyloxycarbonyl, (isoquinolin-7-yl)methyloxycarbonyl, 1-(isoquinolin-7-yl)ethyloxycarbonyl, (isoquinolin-8-yl)methyloxycarbonyl, 1-(isoquinolin-8-yl)ethyl quinolin-2-yl)methyloxycarbonyl, 1-(quinolin-2-yl)ethyloxycarbonyl, (quinolin-3-yl)methyloxycarbonyl, 1-(quinolin-3-yl)ethyloxycarbonyl, (quinolin-4-yl)methyloxycarbonyl, 1-(quinolin-4-yl)ethyloxycarbonyl, (quinolin-5-yl)methyloxycarbonyl, 1-(quinolin-5-yl)ethyloxycarbonyl, (quinolin-6-yl)methyloxycarbonyl, 1-(quinolin-6-yl)ethyloxycarbonyl,(Quinolin-7-yl)methyloxycarbonyl, 1-(quinolin-7-yl)ethyloxycarbonyl, (quinolin-8-yl)methyloxycarbonyl, 1-(quinolin-8-yl)ethyloxycarbonyl, (benzothiazol-2-yl)methyloxycarbonyl, 1-(benzothiazol-2-yl)ethyloxycarbonyl, (benzothiazol-4-yl)methyloxycarbonyl, 1-(benzothiazol-4-yl)ethyloxycarbonyl, (benzothiazol-5-yl)methyloxycarbonyl, 1-(benzothiazol-5-yl)ethyloxycarbonyl -yl)ethyloxycarbonyl, (benzothiazol-6-yl)methyloxycarbonyl, 1-(benzothiazol-6-yl)ethyloxycarbonyl, (benzothiazol-7-yl)methyloxycarbonyl, 1-(benzothiazol-7-yl)ethyloxycarbonyl, (benzofuran-2-yl)methyloxycarbonyl, 1-(benzofuran-2-yl)ethyloxycarbonyl, (benzofuran-3-yl)methyloxycarbonyl, 1-(benzofuran-3-yl)ethyloxycarbonyl, (benzofuran-4-yl)methyloxycarbonyl oxycarbonyl, 1-(benzofuran-4-yl)ethyloxycarbonyl, (benzofuran-5-yl)methyloxycarbonyl, 1-(benzofuran-5-yl)ethyloxycarbonyl, (benzofuran-6-yl)methyloxycarbonyl, 1-(benzofuran-6-yl)ethyloxycarbonyl, (benzofuran-7-yl)methyloxycarbonyl, 1-(benzofuran-7-yl)ethyloxycarbonyl, (benzothiophen-2-yl)methyloxycarbonyl, 1-(benzothiophen-2-yl)ethyloxycarbonyl, (benzo (benzothiophen-3-yl)methyloxycarbonyl, 1-(benzothiophen-3-yl)ethyloxycarbonyl, (benzothiophen-4-yl)methyloxycarbonyl, 1-(benzothiophen-4-yl)ethyloxycarbonyl, (benzothiophen-5-yl)methyloxycarbonyl, 1-(benzothiophen-5-yl)ethyloxycarbonyl, (benzothiophen-6-yl)methyloxycarbonyl, 1-(benzothiophen-6-yl)ethyloxycarbonyl, (benzothiophen-7-yl)methyloxycarbonyl,1-(benzothiophen-7-yl)ethyloxycarbonyl, (benzisoxazol-3-yl)methyloxycarbonyl, 1-(benzisoxazol-3-yl)ethyloxycarbonyl, (benzisoxazol-4-yl)methyloxycarbonyl, 1-(benzisoxazol-4-yl)ethyloxycarbonyl, (benzisoxazol-5-yl)methyloxycarbonyl, 1-(benzisoxazol-5-yl)ethyloxycarbonyl, (benzisoxazol-6-yl)methyloxycarbonyl, 1-( (benzoisoxazol-6-yl)ethyloxycarbonyl, (benzoisoxazol-7-yl)methyloxycarbonyl, 1-(benzoisoxazol-7-yl)ethyloxycarbonyl, (pyrazolopyridin-1-yl)methyloxycarbonyl, 1-(pyrazolopyridin-1-yl)ethyloxycarbonyl, (pyrazolopyridin-3-yl)methyloxycarbonyl, 1-(pyrazolopyridin-3-yl)ethyloxycarbonyl, (pyrazolopyridin-4-yl)methyloxycarbonyl, 1-(pyrazolopyridin-4-yl)ethyl ethyloxycarbonyl, (pyrazolopyridin-5-yl)methyloxycarbonyl, 1-(pyrazolopyridin-5-yl)ethyloxycarbonyl, (pyrazolopyridin-6-yl)methyloxycarbonyl, 1-(pyrazolopyridin-6-yl)ethyloxycarbonyl, (pyrazolopyrimidin-1-yl)methyloxycarbonyl, 1-(pyrazolopyrimidin-1-yl)ethyloxycarbonyl, (pyrazolopyrimidin-2-yl)methyloxycarbonyl, 1-(pyrazolopyrimidin-2-yl)ethyloxycarbonyl, (pyrazolopyrimidin (pyrazolopyrimidin-3-yl)methyloxycarbonyl, 1-(pyrazolopyrimidin-3-yl)ethyloxycarbonyl, (pyrazolopyrimidin-5-yl)methyloxycarbonyl, 1-(pyrazolopyrimidin-5-yl)ethyloxycarbonyl, (pyrazolopyrimidin-6-yl)methyloxycarbonyl, 1-(pyrazolopyrimidin-6-yl)ethyloxycarbonyl, (pyrazolopyrimidin-7-yl)methyloxycarbonyl, 1-(pyrazolopyrimidin-7-yl)ethyloxycarbonyl, (pyrrolopyridin-1-yl)methyloxycarbonyl,1-(pyrrolopyridin-1-yl)ethyloxycarbonyl, (pyrrolopyridin-2-yl)methyloxycarbonyl, 1-(pyrrolopyridin-2-yl)ethyloxycarbonyl, (pyrrolopyridin-3-yl)methyloxycarbonyl, 1-(pyrrolopyridin-3-yl)ethyloxycarbonyl, (pyrrolopyridin-4-yl)methyloxycarbonyl, 1-(pyrrolopyridin-4-yl)ethyloxycarbonyl, (pyrrolopyridin-5-yl)methyloxycarbonyl, 1-(pyrrolopyridin-5-yl)ethyloxycarbonyl, (Pyrrolopyridin-6-yl)methyloxycarbonyl, 1-(pyrrolopyridin-6-yl)ethyloxycarbonyl, (triazolopyridin-3-yl)methyloxycarbonyl, 1-(triazolopyridin-3-yl)ethyloxycarbonyl, (triazolopyridin-4-yl)methyloxycarbonyl, 1-(triazolopyridin-4-yl)ethyloxycarbonyl, (triazolopyridin-5-yl)methyloxycarbonyl, 1-(triazolopyridin-5-yl)ethyloxycarbonyl, (triazolopyridin-6-yl)methyl ethyloxycarbonyl, 1-(triazolopyridin-6-yl)ethyloxycarbonyl, (triazolopyridin-7-yl)methyloxycarbonyl, 1-(triazolopyridin-7-yl)ethyloxycarbonyl, (triazolopyrimidin-2-yl)methyloxycarbonyl, 1-(triazolopyrimidin-2-yl)ethyloxycarbonyl, (triazolopyrimidin-3-yl)methyloxycarbonyl, 1-(triazolopyrimidin-3-yl)ethyloxycarbonyl, (triazolopyrimidin-6-yl)methyloxycarbonyl quinazolin-6-yl)ethyloxycarbonyl, (triazolopyrimidin-7-yl)methyloxycarbonyl, 1-(triazolopyrimidin-7-yl)ethyloxycarbonyl, (quinazolin-2-yl)methyloxycarbonyl, 1-(quinazolin-2-yl)ethyloxycarbonyl, (quinazolin-4-yl)methyloxycarbonyl, 1-(quinazolin-4-yl)ethyloxycarbonyl, (quinazolin-5-yl)methyloxycarbonyl, 1-(quinazolin-5-yl)ethyloxycarbonyl,(quinazolin-6-yl)methyloxycarbonyl, 1-(quinazolin-6-yl)ethyloxycarbonyl, (quinazolin-7-yl)methyloxycarbonyl, 1-(quinazolin-7-yl)ethyloxycarbonyl, (quinazolin-8-yl)methyloxycarbonyl, 1-(quinazolin-8-yl)ethyloxycarbonyl, (quinoxalin-2-yl)methyloxycarbonyl, 1-(quinoxalin-2-yl)ethyloxycarbonyl oxycarbonyl, (quinoxalin-3-yl)methyloxycarbonyl, 1-(quinoxalin-3-yl)ethyloxycarbonyl, (quinoxalin-5-yl)methyloxycarbonyl, 1-(quinoxalin-5-yl)ethyloxycarbonyl, (quinoxalin-6-yl)methyloxycarbonyl, 1-(quinoxalin-6-yl)ethyloxycarbonyl, (quinoxalin-7-yl)methyloxycarbonyl, 1-(quinoxalin-3-yl)ethyloxycarbonyl (quinoxalin-7-yl)ethyloxycarbonyl, (quinoxalin-8-yl)methyloxycarbonyl, 1-(quinoxalin-8-yl)ethyloxycarbonyl, (cinnolin-3-yl)methyloxycarbonyl, 1-(cinnolin-3-yl)ethyloxycarbonyl, (cinnolin-4-yl)methyloxycarbonyl, 1-(cinnolin-4-yl)ethyloxycarbonyl, (cinnolin-5-yl)methyloxycarbonyl Examples of the cinnolinyl include cinnolinyl, 1-(cinnolin-5-yl)ethyloxycarbonyl, (cinnolin-6-yl)methyloxycarbonyl, 1-(cinnolin-6-yl)ethyloxycarbonyl, (cinnolin-7-yl)methyloxycarbonyl, 1-(cinnolin-7-yl)ethyloxycarbonyl, (cinnolin-8-yl)methyloxycarbonyl, and 1-(cinnolin-8-yl)ethyloxycarbonyl.

[0079] In the present invention, unless otherwise specified, "C1-C6 alkyloxyimino C1-C6 alkyl group" refers to a (C1-C6 alkyl)-ON=(C1-C6 alkyl) group in which the alkyloxy moiety and alkyl moiety have the above-mentioned meanings, and examples thereof include 1-(methyloxyimino)methyl, 1-(methyloxyimino)ethyl, 2-(methyloxyimino)ethyl, 1-(methyloxyimino)propyl, 2-(methyloxyimino)propyl, 3-(methyloxyimino)propyl, 1-(ethyloxyimino)methyl, 1-(ethyloxyimino)ethyl, 2-(ethyloxyimino)ethyl, 1-(ethyloxyimino)propyl, 2-(ethyloxyimino)propyl, 3-(ethyloxyimino)propyl, 1-(isopropyloxyimino)ethyl, 2-(isopropyloxyimino)ethyl, and other groups.

[0080] In the present invention, unless otherwise specified, the term "C1-C6 haloalkyloxyimino C1-C6 alkyl group" refers to a (C1-C6 haloalkyl)-ON=(C1-C6 alkyl) group in which the haloalkyloxy moiety and alkyl moiety have the above-mentioned meanings, and examples thereof include 1-(fluoromethoxyimino)methyl, 1-(fluoromethoxyimino)ethyl, 2-(fluoromethoxyimino)ethyl, 1-(fluoromethoxyimino)propyl, 2-(fluoromethoxyimino)propyl, 3-(fluoromethoxyimino)propyl, 1-(difluoromethoxyimino)propyl, 1-(fluoromethoxyimino)methyl, 1-(fluoromethoxyimino)ethyl, 2-(fluoromethoxyimino)propyl, 3-(fluoromethoxyimino)propyl, 1 ... (trifluoromethoxyimino)methyl, 1-(difluoromethoxyimino)ethyl, 2-(difluoromethoxyimino)ethyl, 1-(difluoromethoxyimino)propyl, 2-(difluoromethoxyimino)propyl, 3-(difluoromethoxyimino)propyl, 1-(trifluoromethoxyimino)methyl, 1-(trifluoromethoxyimino)ethyl, 2-(trifluoromethoxyimino)ethyl, 1-(trifluoromethoxyimino)propyl, 2-(trifluoromethoxyimino)propyl, 3-(trifluoromethoxyimino)propyl, 1-(trifluoromethoxyimino)methyl 2-(trichloromethoxyimino)ethyl, 1-(trichloromethoxyimino)propyl, 2-(trichloromethoxyimino)propyl, 3-(trichloromethoxyimino)propyl, 1-(2,2,2-trifluoroethyloximino)methyl, 1-(2,2,2-trifluoroethyloximino)ethyl, 2-(2,2,2-trifluoroethyloximino)ethyl, 1-(2,2,2-trifluoroethyloximino)propyl, 2-(2,2,2-trifluoroethyloximino)ethyl, ethyloximino)propyl, 3-(2,2,2-trifluoroethyloximino)propyl, 1-(pentafluoroethyloximino)methyl, 1-(pentafluoroethyloximino)ethyl, 2-(pentafluoroethyloximino)ethyl, 1-(pentafluoroethyloximino)propyl, 2-(pentafluoroethyloximino)propyl, 3-(pentafluoroethyloximino)propyl, 1-(2,2,2-trichloroethyloximino)methyl, 1-(2,2,2-trichloroethyloximino)ethyl, 2-(2,2,2-trichloroethyloximino)ethyl, 1-(2,2,2-trichloroethyloximino)propyl, 2-2,2,2-trichloroethyloximino)propyl, 3-(2,2,2-trichloroethyloximino)propyl, 1-(3,3,3-trifluoropropyloximino)methyl, 1-(3,3,3-trifluoropropyloximino)ethyl, 2-(3,3,3-trifluoropropyloximino)ethyl, 1-(3,3,3-trifluoropropyloximino)propyl Pyr, 2-(3,3,3-trifluoropropyloximino)propyl, 3-(3,3,3-trifluoropropyloximino)propyl, 1-(1,1,2,3,3,3-hexafluoropropyloximino)methyl, 1-(1,1,2,3,3,3-hexafluoropropyloximino)ethyl, 2-(1,1,2,3,3,3-hexafluoropropyloximino)ethyl, 1-(1,1,2,3,3,3-hexafluoropropyloximino)propyl, 2-(1,1,2,3 ,3,3-hexafluoropropyloximino)propyl, 3-(1,1,2,3,3,3-hexafluoropropyloximino)propyl, 1-(heptafluoropropyloximino)methyl, 1-(heptafluoropropyloximino)ethyl, 2-(heptafluoropropyloximino)ethyl, 1-(heptafluoropropyloximino)propyl, 2-(heptafluoropropyloximino)propyl, 3-(heptafluoropropyloximino)propyl, 1-(1,1, 1,3,3,3-Hexafluoropropan-2-yloxyimino)methyl, 1-(1,1,1,3,3,3-Hexafluoropropan-2-yloxyimino)ethyl, 2-(1,1,1,3,3,3-Hexafluoropropan-2-yloxyimino)ethyl, 1-(1,1,1,3,3,3-Hexafluoropropan-2-yloxyimino)propyl, 2-(1,1,1,3,3,3-Hexafluoropropan-2-yloxyimino)propyl, 3-(1,1,1,3,3,Examples of such groups include 3-hexafluoropropan-2-yloxyimino)propyl, 1-(heptafluoropropan-2-yloxyimino)methyl, 1-(heptafluoropropan-2-yloxyimino)ethyl, 2-(heptafluoropropan-2-yloxyimino)ethyl, 1-(heptafluoropropan-2-yloxyimino)propyl, 2-(heptafluoropropan-2-yloxyimino)propyl, and 3-(heptafluoropropan-2-yloxyimino)propyl.

[0081] In the present invention, unless otherwise specified, the term "C3-C6 cycloalkyloxyimino C1-C6 alkyl group" refers to a (C3-C6 cycloalkyl)-ON=(C1-C6 alkyl) group in which the cycloalkyloxy moiety and alkyl moiety have the above-mentioned meanings, and examples thereof include 1-(cyclopropyloxyimino)methyl, 1-(cyclopropyloxyimino)ethyl, 2-(cyclopropyloxyimino)ethyl, 1-(cyclopropyloxyimino)propyl, and 2-(cyclopropyloxyimino)propyl.

[0082] In the present invention, "one or more R 5 "May be substituted by a substituent" means "one or more R 5 Two or more R 5 When replaced by R 5 may be the same or different, R 5 are each independently a cyano group, an amino group, a nitro group, a hydroxy group, a halogen atom, a thiol group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkylcarbonylamino group (the amino group is R 6 a C1-C6 alkylamino group (the amino group may be substituted with a substituent selected from R 6 a C1-C6 alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from R 6and C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkyloxy group, C1-C6 haloalkyloxy group, C3-C6 cycloalkyloxy group, C1-C6 alkyloxy-C1-C6 alkyl group, C1-C6 haloalkyloxy-C1-C6 alkyl group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C3-C6 cycloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C3-C6 cycloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, or C3-C6 cycloalkylsulfonyl group.

[0083] In the present invention, "R 1 and R 2 may each form a 3- to 6-membered monocyclic carbocyclic ring together with the carbon atom to which they are bonded, and the carbocyclic ring may each be substituted by a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, but is not limited to the following:

[0084] [ka]

[0085] In the present invention, agriculturally acceptable salts and salts refer to salts of a nitrogen-containing heterocyclic group, a hydroxyl group, a carboxyl group, an amino group, or the like present in the structure of the compound of the present invention represented by general formula [I], and a salt of the group with a metal or organic base, or a salt of a mineral acid or organic acid. Examples of metals include alkali metals such as sodium or potassium, and alkaline earth metals such as magnesium or calcium. Examples of organic bases include triethylamine or diisopropylamine. Examples of mineral acids include hydrochloric acid, hydrobromic acid, and sulfuric acid. Examples of organic acids include formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, 4-toluenesulfonic acid, and trifluoromethanesulfonic acid.

[0086] Next, representative examples of compounds included in the aryloxadiazole compounds of the present invention represented by general formula [I] are shown in Tables 1 to 7. However, the compounds included in the present invention are not limited to these. The compound numbers in the tables will be referred to in the following description.

[0087] The aryloxadiazole compounds of the present invention may have geometric isomers of E- and Z-isomers depending on the type of substituent, and the present invention includes mixtures containing these E- and Z-isomers in any ratio. The compounds of the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and sulfur atoms, and the present invention includes all optically active compounds, racemates, and diastereomers.

[0088] The following symbols in the tables in this specification represent the corresponding groups as described below. Me: methyl; Et: ethyl; n-Pr: n-propyl; i-Pr: isopropyl; n-Bu: n-butyl t-Bu: tert-butyl; c-Pr: cyclopropyl; c-Bu: cyclobutyl; CF3: trifluoromethyl; CO2Me: methyloxycarbonyl; Ph(2-F): 2-fluorophenyl; Ph(2,3-F2): 2,3-difluorophenyl; pyridin-2-yl(3-F): 3-fluoro-pyridin-2-yl; CO2CH2(pyridin-2-yl): pyridin-2-ylmethyloxycarbonyl; C(CH2CH3)(=NOMe): 1-(methyloxyimino)ethyl;

[0089] [Table 1]

[0090] [Table 2]

[0091] [Table 3]

[0092] [Table 4]

[0093] [Table 5]

[0094] [Table 6]

[0095] [Table 7]

[0096] On the other hand, the compound of the present invention represented by general formula [I] can be produced according to the production methods shown below, but is not limited to these methods. Hereinafter, for example, "a compound represented by general formula [I-1]" and "compound [I-1]" are synonymous.

[0097] <Manufacturing method 1> Among the compounds of the present invention, the compound represented by the general formula [I-1] can be prepared, for example, according to the following method.

[0098] [ka]

[0099] (In the formula, L 1represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyl group, a benzenesulfonyloxy group, a 4-toluenesulfonyloxy group, a 1-imidazolyl group, or the like; L 2 represents a halogen atom, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, a benzoyloxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, a 4-toluenesulfonyloxy group, or the like; L 3 represents a halogen atom, a C1-C6 alkyloxy group, a C1-C6 haloalkyloxy group, a phenoxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a benzenesulfonyloxy group, a 4-toluenesulfonyloxy group, a 1-imidazolyl group, an acetoxy group, a trifluoroacetoxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, or the like; Z 1 is one or more R which may be the same or different at substitutable positions. 5 C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C6 cycloalkyl group, C1-C6 haloalkyloxy group, C3-C6 cycloalkyloxy group, C6-C 12 Aryloxy group, 5-12 membered heteroaryloxy group, C1-C6 alkyloxy C1-C6 alkyl group, C1-C6 haloalkyloxy C1-C6 alkyl group, C3-C6 cycloalkyloxy C1-C6 alkyl group, C6-C 12 Aryloxy C1-C6 alkyl group, 5-12 membered heteroaryloxy C1-C6 alkyl group, C6-C 12 represents an aryl group or a 5- to 12-membered heteroaryl group, and R 3’ is a cyano group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C3-C6 cycloalkylcarbonyl group, a hydroxy C1-C6 alkyl group, a C1-C6 alkyloxy C1-C6 alkyl group, a C1-C6 haloalkyloxy C1-C6 alkyl group, a C3-C6 cycloalkyloxy C1-C6 alkyl group, a C6-C 12Aryloxy C1-C6 alkyl group, C1-C6 alkyloxycarbonyl group, C1-C6 haloalkyloxycarbonyl group, C3-C6 cycloalkyloxycarbonyl group, C6-C 12 Aryl C1-C6 alkyloxycarbonyl group, 5-12 membered heteroaryl C1-C6 alkyloxycarbonyl group, C1-C6 alkyloxyimino C1-C6 alkyl group, C1-C6 haloalkyloxyimino C1-C6 alkyl group, C3-C6 cycloalkyloxyimino C1-C6 alkyl group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C3-C6 cycloalkylthio group, C6-C 12 aryl group, or 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R 5 A may be substituted by a substituent; 1 , A 2 , A 3 , A 4 , X, R 1 , R 2 and R 5 has the same meaning as above.)

[0100] That is, the compound represented by general formula [I-1] can be produced by (Step 1-1) reacting compound [II-1] with compound [V-1] in the presence or absence of a suitable solvent, a suitable base, and a suitable catalyst. Furthermore, (Step 1-2) the compound represented by general formula [I-1] can also be produced by reacting compound [II-2] with compound [V-2] in the presence or absence of a suitable solvent, a suitable base, and a suitable acid catalyst. Furthermore, (Step 1-3) the compound represented by general formula [I-1] can also be produced by reacting compound [III-1] with compound [V-3] in the presence or absence of a suitable solvent and a suitable base.

[0101] (Process 1-1) The amount of the compound [V-1] used in this reaction may be appropriately selected usually within a range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [II-1].

[0102] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 0.5 to 10 moles per mole of compound [II-1], and is preferably 1.0 to 5.0 moles.

[0103] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide, potassium iodide, etc. The amount of catalyst used can be appropriately selected from the range of 0.01 to 0.5 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II-1].

[0104] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; 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; 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 a mixture thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of the compound [II-1].

[0105] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably 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 10 minutes to 72 hours.

[0106] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [I-1]. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0107] (Step 1-2) The amount of the compound [V-2] used in this reaction may be appropriately selected usually within a range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [II-2].

[0108] Compound [II-2] can be produced by the method described on page 68 of European Patent Publication EP3187497 or a method similar thereto.

[0109] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 selected appropriately from the range of 0.5 to 10 moles per mole of compound [II-2], and is preferably 1.0 to 5.0 moles.

[0110] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; and mixtures thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of compound [II-2].

[0111] Examples of the acid catalyst that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, etc.; carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid, etc.; sulfonic acids such as methanesulfonic acid, 4-toluenesulfonic acid, trifluoromethanesulfonic acid, etc. The amount of the acid catalyst used can be appropriately selected usually within a range of 0.01 to 10 mol, and preferably 0.01 to 5.0 mol, per 1 mol of compound [II-2].

[0112] The reaction temperature for this reaction may be selected from the range of temperatures usually from 0°C to the reflux temperature of the reaction system, and is preferably from 20°C to the reflux temperature of the reaction system.

[0113] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0114] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [I-1]. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0115] (Step 1-3) The amount of the compound [V-3] used in this reaction may be appropriately selected usually within a range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [III-1].

[0116] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 0.5 to 10 moles per mole of compound [III-1], and is preferably 1.0 to 5.0 moles.

[0117] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, and N Examples of the solvent include aprotic polar solvents such as 1,3-dimethyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; 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; and a mixture thereof. The amount of the solvent used is 0.1 to 100 liters, and preferably 0.1 to 20 liters, per mole of compound [III-1].

[0118] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably from 0°C to the reflux temperature of the reaction system.

[0119] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0120] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [I-1]. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0121] <Manufacturing method 2> Among the compounds of the present invention, the compound represented by the general formula [II-1] can be prepared, for example, according to the following method.

[0122] [ka] (In the formula, L 2 , Z 1 , A 1 , A 2 , A 3 , A 4 , X has the same meaning as above.)

[0123] That is, the compound represented by the general formula [II-1] can be produced by reacting the compound [II-3] with the compound [V-2] in the presence or absence of a suitable solvent and in the presence or absence of a suitable acid catalyst. The compound [II-3] can be produced by the method described in WO 2007 / 111212, page 323, or a method similar thereto.

[0124] The amount of the compound [V-2] used in this reaction may be appropriately selected usually within the range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [II-3].

[0125] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 0.5 to 10 moles per mole of compound [II-3], and is preferably 1.0 to 5.0 moles.

[0126] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; and mixtures thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of compound [II-3].

[0127] Examples of the acid catalyst that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid, carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid, 4-toluenesulfonic acid, and trifluoromethanesulfonic acid. The amount of the acid catalyst used can be appropriately selected usually within a range of 0.01 to 10 mol, and preferably 0.01 to 5.0 mol, per 1 mol of compound [II-3].

[0128] The reaction temperature for this reaction may be selected from the range of temperatures usually from 0°C to the reflux temperature of the reaction system, and is preferably from 20°C to the reflux temperature of the reaction system.

[0129] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0130] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [II-1]. The isolated compound [II-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0131] <Manufacturing method 3> The compound represented by the general formula [III-1] can be produced, for example, according to the following method.

[0132] [ka] (In the formula, Z 1 , A 1 , A 2 , A 3 , A 4 , R 1 , R 2 and R 3′ has the same meaning as above.)

[0133] That is, the compound represented by the general formula [III-1] can be produced by reacting the compound [IV-1] with an appropriate hydroxylamine in the presence of an appropriate solvent and in the presence or absence of an appropriate base.

[0134] Examples of hydroxylamines that can be used in this reaction include aqueous hydroxylamine solution, hydroxylamine hydrochloride, hydroxylamine sulfate, etc. The amount of the hydroxylamine used may be appropriately selected from the range of 1.0 to 20 mol, preferably 1.0 to 10 mol, per 1 mol of compound [IV-1].

[0135] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 0.5 to 10 moles per mole of compound [IV-1], and is preferably 1.0 to 10 moles.

[0136] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, and N Examples of the solvent include aprotic polar solvents such as 1,3-dimethyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; 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 a mixture thereof. The amount of the solvent used is 0.1 to 100 liters, and preferably 0.1 to 20 liters, per mole of compound [IV-1].

[0137] The reaction temperature for this reaction may be selected from the range of temperatures usually from 0°C to the reflux temperature of the reaction system, and is preferably from room temperature to the reflux temperature of the reaction system. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0138] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [III-1]. The isolated compound [III-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0139] <Manufacturing method 4> The compound represented by the general formula [IV-1] can be produced, for example, according to the following method. [ka] (In the formula, L 1 , L 2 , Z 1 , A 1 , A 2 , A 3 , A 4 , R 1 , R 2 and R 3‘ has the same meaning as above. ) has the same meaning as above.

[0140] That is, the compound represented by general formula [IV-1] can be produced by (Step 4-1) reacting compound [IV-2] with compound [V-1] in the presence or absence of a suitable solvent, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst. Furthermore, the compound represented by general formula [IV-1] can be produced by (Step 4-2) reacting compound [IV-3] with compound [V-2] in the presence or absence of a suitable solvent and in the presence or absence of a suitable acid catalyst.

[0141] (Step 4-1) The amount of the compound [V-1] used in this reaction may be appropriately selected usually within a range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [IV-2].

[0142] Compound [IV-2] can be produced, for example, by the method described in Bioorganic and Medicinal Chemistry 2012, Vol. 20, p. 3575 or a method analogous thereto.

[0143] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 0.5 to 10 moles per mole of compound [IV-2], and is preferably 1.0 to 5.0 moles.

[0144] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide, potassium iodide, etc. The amount of the catalyst used can be appropriately selected from the range of 0.01 to 0.5 mol, preferably 0.01 to 0.1 mol, per mol of compound [IV-2].

[0145] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; 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; 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 a mixture thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of the compound [IV-2].

[0146] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 100°C.

[0147] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0148] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [IV-1]. The isolated compound [IV-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0149] (Step 4-2) The amount of the compound [V-2] used in this reaction may be appropriately selected usually within a range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [IV-3].

[0150] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 0.5 to 10 moles per mole of compound [IV-3], and is preferably 1.0 to 5.0 moles.

[0151] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; and mixtures thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of compound [IV-3].

[0152] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, Examples of the solvent include aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, etc.; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve, etc.; nitriles such as acetonitrile, propionitrile, etc.; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane, etc.; pyridines such as pyridine, picoline, lutidine, etc.; tertiary amines such as triethylamine, tributylamine, etc.; and mixed solvents thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of compound [IV-3].

[0153] Examples of the acid catalyst that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid, carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid, 4-toluenesulfonic acid, and trifluoromethanesulfonic acid. The amount of the acid catalyst used can be appropriately selected usually within a range of 0.01 to 10 mol, and preferably 0.01 to 5.0 mol, per 1 mol of compound [IV-3].

[0154] The reaction temperature for this reaction may be selected from the range of temperatures usually from 0°C to the reflux temperature of the reaction system, and is preferably from room temperature to the reflux temperature of the reaction system. The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0155] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [IV-1]. The isolated compound [IV-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0156] <Manufacturing method 5> Among the compounds of the present invention, the compound represented by the general formula [I-2] can be prepared, for example, according to the following method.

[0157] [ka] (In the formula, Z, A 1 , A 2 , A 3 , A 4 , X, R 1 , R 2 and R 3‘ has the same meaning as above.)

[0158] That is, the compound represented by the general formula [I-2] can be produced by reacting the compound represented by the general formula [I] with a suitable thiocarbonylating agent in the presence or absence of a suitable base and in the presence or absence of a suitable solvent.

[0159] The thiocarbonylating agent used in this reaction may be, for example, diphosphorus pentasulfide or Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide). The amount of the thiocarbonylating agent used may be appropriately selected from the range of 0.25 to 100 mol, preferably 0.5 to 3.0 mol, per 1 mol of compound [I].

[0160] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal carbonates, e.g., sodium carbonate, potassium carbonate, etc.; and organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5,4,0]-7-undecene, etc. The amount of the base used can be appropriately selected from the range of 0.01 to 10 mol per mol of compound [I], and is preferably 0.1 to 2.0 mol.

[0161] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; aprotic polar solvents such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; and mixed solvents thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 50 liters, per mole of compound [I].

[0162] The reaction temperature for this reaction may be selected from any temperature range from 0°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0163] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0164] After the reaction is complete, the compound [I-2] can be isolated by concentrating the reaction mixture or by pouring it into water, extracting it with an organic solvent, and then concentrating it. The isolated compound [I-2] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0165] <Manufacturing method 6> The compound represented by the general formula [II-2] can be produced, for example, according to the following method.

[0166] [ka] (Wherein, W represents a C1-C6 alkyl group, a C1-C6 alkyloxy group, or a C1-C6 haloalkyl group; L 1 , A 1 , A 2 , A 3 , A 4 , X, R 1 , R 2 and R 3‘ has the same meaning as above.)

[0167] (Step 6-1) That is, the compound represented by general formula [II-2] can be produced by (step 6-1) reacting compound [II-4] with compound [V-1] in the presence or absence of a suitable solvent, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst to obtain compound [II-5], and then (step 6-2) deprotecting compound [II-5] according to the method described in GREENE'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter GMWuts).

[0168] The amount of the compound [V-1] used in this reaction may be appropriately selected usually within a range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [II-4].

[0169] 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 hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethyloxide, and potassium tert-butyloxide; and 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 selected appropriately from the range of 0.5 to 10 moles per mole of compound [II-4], and is preferably 1.0 to 5.0 moles.

[0170] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide, potassium iodide, etc. The amount of catalyst used can be appropriately selected from the range of 0.01 to 0.5 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II-4].

[0171] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; 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; 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 a mixture thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 20 liters, per mole of the compound [II-4].

[0172] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably 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 10 minutes to 72 hours.

[0173] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [II-5]. The isolated compound [II-5] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0174] The starting compound [II-4] can be produced by the method described on page 323 of International Publication No. 2007 / 111212 or by a method similar thereto.

[0175] <Manufacturing method 7> The compound represented by the general formula [I-7] can be produced, for example, according to the following method. TIFF2025132253000016.tif37153 (in the formula, R 7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C6 cycloalkyl group; n represents an integer of 1 or 2; Z, A 1 , A 2 , A 3 , A 4 , X, R 1 and R 2 has the same meaning as above.)

[0176] That is, the compound represented by the general formula [I-7] can be produced by reacting the compound represented by the compound [I-6] with a suitable oxidizing agent in the presence or absence of a suitable solvent and in the presence or absence of a catalyst.

[0177] Examples of oxidizing agents that can be used in this reaction include organic peroxides such as m-chloroperbenzoic acid, performic acid, peracetic acid, and trifluoroperacetic acid; inorganic peroxides such as hydrogen peroxide, potassium permanganate, Oxone (registered trademark) (a product of E.I. du Pont de Nemours and Company, containing potassium hydrogen peroxosulfate), and tert-butyl hydroperoxide; and halogen acid salts such as sodium periodate, sodium chlorite, and sodium hypochlorite. The amount of the oxidizing agent used may be appropriately selected from the range of 0.5 to 5.0 mol per mol of compound [I-6], and is preferably 0.9 to 3.0 mol.

[0178] Examples of catalysts that can be used in this reaction include 2-methyl-2-butene, sodium dihydrogen phosphate, ruthenium trichloride hydrate, vanadium (IV) acetylacetonate, etc. The amount of the catalyst used can be appropriately selected from the range of 0.001 to 10.0 mol per 1 mol of compound [I-6], and is preferably 0.01 to 1.0 mol.

[0179] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as acetone, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; and water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per mole of the compound [I-6].

[0180] The reaction temperature for this reaction may be selected from any temperature range from -78°C to the reflux temperature of the reaction system, and is preferably in the range of -10°C to 100°C.

[0181] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours.

[0182] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [I-7].

[0183] The isolated compound [I-7] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0184] The agricultural and horticultural plant disease control agent of the present invention is characterized by containing the aryloxadiazole compound represented by the general formula [I] of the present invention or a salt thereof as an active ingredient.

[0185] The agricultural and horticultural plant disease control agent of the present invention can contain, if necessary, an additive component (carrier) that is usually used in pesticide formulations.

[0186] Examples of the additive components include carriers such as solid or liquid carriers, surfactants, binders, tackifiers, thickeners, colorants, spreading agents, adhesives, antifreeze agents, anticaking agents, disintegrants, antidecomposition agents, etc. If necessary, preservatives, plant fragments, etc. may also be used as additive components. These additive components may be used alone or in combination of two or more.

[0187] The additive components will be described below.

[0188] Examples of solid carriers include mineral carriers such as pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgus clay, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, synthetic silicates, etc.), and titanium dioxide; plant carriers such as wood flour, corn stalks, walnut shells, fruit kernels, rice husks, sawdust, bran, soybean flour, powdered cellulose, starch, dextrin, and sugars; inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, and urea-aldehyde resin.

[0189] 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 ethyl ether, 1,4-dioxane, cellosolve, dipropyl ether, and tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, and mineral oil; toluene, C9-C 10 Examples of suitable organic solvents include aromatic hydrocarbons such as alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, 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 above vegetable oils; and water.

[0190] The surfactant is not particularly limited, but is preferably one which gels in water or exhibits swelling properties, and examples thereof include 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 condensates, polyoxyethylene polyoxypropylene block polymers, alkyl polyoxyethylene polypropylene block polymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine-containing ... nonionic surfactants such as fluorine-based surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkyl amine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride;Examples of amphoteric surfactants include betaine-type surfactants such as dialkyldiaminoethyl betaine and alkyldimethylbenzyl betaine, and amino acid-type surfactants such as dialkylaminoethyl glycine and alkyldimethylbenzyl glycine; Examples of binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol, polyethylene oxide, and natural phospholipids (e.g., cephalic acid, lecithin, etc.).

[0191] Examples of binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, and natural phospholipids (e.g., cephalic acid, lecithin, etc.).

[0192] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, and polysaccharides; and inorganic fine powders such as high-purity bentonite and white carbon.

[0193] Examples of colorants include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0194] Examples of spreading agents include silicone 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, and alkynediols.

[0195] Examples of spreading agents include various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, and polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol-formalin condensate, and synthetic resin emulsion.

[0196] Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0197] Examples of the anti-caking agent include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, and petroleum resin.

[0198] Examples of disintegrants include sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0199] Examples of anti-decomposition agents include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenols, amines, sulfurs, and phosphoric acids; and ultraviolet absorbers such as salicylic acid and benzophenones.

[0200] Examples of preservatives include potassium sorbate and 1,2-benzothiazol-3(2H)-one.

[0201] Examples of plant fragments include sawdust, coconut husks, corn cobs, tobacco stalks, and the like.

[0202] On the other hand, when the agricultural and horticultural plant disease control agent of the present invention contains the above-mentioned additive components, the content ratio thereof is selected, by mass, from typically 5 to 95%, preferably 20 to 90%, for carriers such as solid carriers or liquid carriers; from typically 0.1 to 30%, preferably 0.5 to 10%, for surfactants; and from 0.1 to 30%, preferably 0.5 to 10%, for other additives.

[0203] The agricultural and horticultural plant disease control agent of the present invention can be formulated for use in any dosage form, such as a dust, dust granule, granule, wettable powder, water-soluble powder, water dispersible granule, tablet, jumbo formulation, emulsifiable concentrate, oil formulation, liquid formulation, flowable formulation, oil suspension, emulsion, microemulsion, suspoemulsion, trace amount spray, microcapsule, fumigation agent, aerosol, bait, or paste.

[0204] When these formulations are actually used, they can be used as they are or can be diluted to a predetermined concentration with a diluent such as water. The application of various formulations containing the compounds of the present invention or their diluted forms can be carried out by commonly used application methods, i.e., spraying (e.g., spraying, misting, atomizing, dusting, granules, water surface application, box application, etc.), soil application (e.g., mixing, irrigation, etc.), surface application (e.g., coating, dusting, covering, etc.), seed treatment (e.g., smearing, dusting treatment, etc.), immersion, poison bait, fumigation, etc. Furthermore, the active ingredient can be mixed with feed and given to livestock to control the occurrence and growth of pests, particularly harmful insects, in their excrement.

[0205] The method for controlling diseases of agricultural and horticultural plants of the present invention can be carried out by using an active ingredient amount of the aryloxadiazole compound or a salt thereof of the present invention in the above-mentioned application method.

[0206] The blending ratio (mass %) of the active ingredient in the agricultural and horticultural plant disease control agent of the present invention is appropriately selected as needed. For example, in the case of a dust, dust granule, fine granule, etc., it is appropriately selected from the range of 0.01 to 20%, preferably 0.05 to 10%, in the case of a granule, etc., it is appropriately selected from the range of 0.1 to 30%, preferably 0.5 to 20%, in the case of a wettable powder, water dispersible granule, etc., it is appropriately selected from the range of 1 to 70%, preferably 5 to 50%, in the case of a water-soluble agent, liquid agent, etc., it is appropriately selected from the range of 1 to 95%, preferably 10 to 80%, in the case of a water-soluble agent, liquid agent, etc., it is appropriately selected from the range of 5 to 90%, preferably 10 to 80%, in the case of an emulsifiable concentrate, etc., it is appropriately selected from the range of 5 to 90%, preferably 10 to 80%, in the case of an oil agent, etc. When forming a flowable agent, oily suspension, etc., it is preferably selected from the range of 5 to 60%, preferably 10 to 50%. When forming an emulsion, microemulsion, suspoemulsion, etc., it is preferably selected from the range of 5 to 70%, preferably 10 to 60%. When forming a tablet, bait, paste, etc., it is preferably selected from the range of 1 to 80%, preferably 5 to 50%. When forming a fumigation agent, etc., it is preferably selected from the range of 0.1 to 50%, preferably 1 to 30%. When forming an aerosol, etc., it is preferably selected from the range of 0.05 to 20%, preferably 0.1 to 10%.

[0207] These formulations are diluted to an appropriate concentration and then sprayed, or applied directly.

[0208] When the agricultural and horticultural plant disease control agent of the present invention is diluted with a diluent, it is generally applied at a concentration of 0.1 to 5000 ppm of the active ingredient. When the formulation is used as is, the application amount per unit area is 0.1 to 5000 g of the active ingredient compound per hectare, but is not limited thereto.

[0209] It goes without saying that the agricultural and horticultural plant disease control agent of the present invention is sufficiently effective when the compound of the present invention is used alone as the active ingredient, but it can also be mixed or used in combination with other fertilizers or pesticides, such as fungicides, antiviral agents, insecticides, miticides, nematicides, synergists, attractants, herbicides, plant growth regulators, etc., as necessary, and in this case, even more excellent effects may be exhibited.

[0210] Next, examples of known fungicides (fungicidal active ingredients) or disease control compounds that may be mixed or used in combination are listed below.

[0211] Fungicidal active ingredient or disease control compound: Agrobacterium radiobacter, azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminopyrifen, ametoctradin, aldimorph, isotianil, isopyrazam, isofetamide, isofetamid, isoflucypram, isoprothiolane, ibuprofen, thiazolinone, thiazolinone, thiazolinone, thiazolinone Puconazole, ipflufenoquin, ipfentrifluconazole, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, imprimatin A A), imprimatin B, edifenphos, etaconazole, ethaboxam, ethirimol, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, organic oiloils), oxadixyl, oxazinylazole, oxathiapiprolin, oxycarboxin, oxyquinoline copper, oxytetracycline, oxpoconazole fumarate, oxolinic acid, copper dioctanoate, octhilinone, ofurace, orysastrobin, o-phenylphenol, kasugamycin, captafol, galquin, carpropamid, carbendazim, carboxin, carvone, Candida Candida oleophila, Candida saitoana, quinoxyfen, quinofumelin, chinomethionat, captan, quinconazole, quintozene, guazatine, cufraneb, coumethoxystrobin, coumoxystrobin, Gliocladium catenulatum, Cryptococcus albidus, kresoxim-methyl, clozylacon, Clonostachys rosea rosea), chlozolinate, chloroinconazide, chlorothalonil, chloroneb, Chaetomium cupreumcupreum, Coniothyrium minitans, cyazofamid, diethofencarb, diclocymet, dichlofluanid, dichlobentiazox, diclomezine, dicloran, dichlorophen, dithianon, diniconazole, diniconazole-M , zineb, dinocap, dipymetitrone, diphenylamine, difenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, simeconazole, dimethirimol, dimethyl disulfide disulfide, dimethomorph, cymoxanil, dimoxystrobin, Pseudozyma flocculosa, Pseudomonas aureofaciens, Pseudomonas chlororaphis, Pseudomonas syringae, Pseudomonas flurorescens, Pseudomonas rhodesiae, ziram, silthiofam, Zucchini yellow mosaic virus attenuated strain, streptomycin, Streptomyces griseoviridisgriseoviridis, Streptomyces lygicus, spiroxamine, sedaxane, seboctylamine, zoxamide, solatenol, dazomet, Talaromyces flavus flavus, tiadinil, thiabendazole, thiram, thiophanate, thiophanate-methyl, thifluzamide, thiram, tecnazene, tecloftalam, tetraconazole, debacarb, tebuconazole, tebufloquin, terbinafine, dodine, dodemorph, triadimenol, triadimefon, triazoxide, trichlamide, triclopyricarb, Trichoderma asperellum asperellum, Trichoderma atroviride, Trichoderma gamsii, Trichoderma stromaticum, Trichoderma paecilomyces, Trichoderma harzianum, Trichoderma viride, Trichoderma virens, Trichoderma polysporum, Trichoderma harzianum rifai, TrichodermaTrichoderma lignorum, tricyclazole, triticonazole, tridemorph, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolnifanide, tolprocarb, nabam, natamycin, naftifine, nitrapyrin, nitrothal-isopropyl, nuarimol, copper nonyl phenol sulphonate, Paenibacillus polymyxa polymyxa, Burkholderia cepacia, Bacillus amyloliquefaciens, Bacillus simplex, Bacillus subtilis, Bacillus pumilus, Bacillus mycoides, Bacillus licheniformis, harpin protein, Variovorax paradoxus, validamycin, valifenalate, Pantoea agglomerans agglomerans, picarbutrazox, bixafen, picoxystrobin, Pythium oligandrumoligandrum), pydiflumetofen, bitertanol, binapacryl, hinokitiol, non-pathogenic Erwinia carotovora, Non-pathogenic Rhizobium vitis (Rhizobium vitis, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriophenone, pyrisoxazole, pyridaclomethyl, pyrifenox, pyributicarb, pyribencarb, pyrimethanil, pyroquilon, vinclozolin, ferbam, famoxadone, phenazine oxide oxide, fenamidone, phenaminestrobin, fenarimol, fenoxanil, fenopyramide, ferimzone, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, folpet, phthalide, Fusarium oxysporum oxysporum), bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, furancarboxylic acid, fluazinam,Fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluxapyroxad, fluquinconazole, fluconazole, fluconazole-cis -cis), fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, flubeneteram, flumethylsulforim, flumetover, flumorph, Phlebiopsis gigantea gigantea, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, bronopol, propamocarb hydrochloride, propiconazole, propineb, probenazole, bromuconazole, flometoquin, florylpicoxamid, hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl,Pefurazoate, penconazole, pencycuron, benzovindiflupyr, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, fosetyl (including salts of aluminium, calcium, sodium, etc.), polyoxin, polycarbamate, Bordeaux mixture, mancopper, mancozeb, mandipropamid, mandestrobin, maneb, myclobutanil, mineral oil oils, mildiomycin, methasulfocarb, metam, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyltetraprole, metconazole, metominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, meptyldinocap, mepronil, iodocarb, laminarin, ledprona, phosphorous acid and salts, basic copper chloride oxychloride), silver, copper(II) sulfate, cuprous oxide, copper hydroxide,Potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, copper sulfate, UK-2A (code number), dodecylbenzenesulfonate bisethylenediamine copper complex salt [II] (DBEDC), triphenyltin acetate (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide (TPTH), 6-chloro-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide (6-chloro-N-[2-(2,4-dimethyphenyl)-2,2-difluoro-ethyl]-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide racemic-3-[6-chloro-3-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1, 2,4-Oxadiazine (rac-3-[6-chloro-3-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine) (chemical name, CAS registration number: 2446124-68-9) (WO 2020 / 127780), 6-chloro-N-[2-(2,4-dimethylphenyl)-2,2-difluorophenyl] 6-chloro-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide (chemical name, CAS registration number: 2435603-06-6) (WO 2020 / 109391),6-chloro-N-[2-(2,4-dimethylphenyl)ethyl]-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide (chemical name, CAS registration number: 2435600-09-0) (WO 2020 / 109391), 6-chloro-N-[2-(2,4-dimethylphenyl)ethyl]-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide noxy]pyridazine-4-carboxamide) (chemical name, CAS registration number: 2435603-15-7) (WO 2020 / 109391), racemic-3-[6-chloro-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine) (chemical name, CAS registration number: 2446123-98-2) (WO 2020 / 127780).

[0212] Next, examples of known insecticides (insecticidal active ingredients), acaricides (acaricidal active ingredients), nematicides (nematicidal active ingredients), and synergist compounds (synergist active ingredients) that may be mixed or used in combination are shown below.

[0213] Insecticidal, acaricidal, nematicidal and synergistic active ingredients: Acrinathrin, azadirachtin, azamethiphos, acinonapyr, 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 isomers), isazophos, isamidofos , isocarbophos, isoxathion, isocycloseram, isofenphos-methyl, isoflualanam, isoprocarb, epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin ), 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 virus), carbaryl, carbosulfan, carbofuran, gamma-BHC, xylylcarb, quinalphos, kinoprene, chinomethionate, 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], cyfluthrin [including beta-isomer], diflubenzuron, cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrin [including alpha-isomer, beta-isomer, theta-isomer, and zeta-isomer], 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, spiropidione, spirobudifen, spiromesifen, sulcofuron sodium, sulfiflumin, sulfluramid, sulfoxaflor, sulfotep, diazinon, thiacloprid, thiapyrachlor, thiamethoxam, thioxam Sazafen (tioxazafen), thiodicarb (thiodicarb), thiocyclam (thiocyclam), thiosultap (thiosultap), thionazin (thionazin), thiofanox (thiofanox), thiometon (thiometon), thioantraniliprole (tiorantraniliprole), cyclopyrazoflor (tyclopyrazoflor), tigolaner (tigolaner), tetrachlorantraniliprole (tetrachlorantraniliprole), tetrachlorvinphos (tetrachlorvinphos), tetradifon (tetradifon), tetraniliprole (tetraniliprole), tetramethylfluthrin (tetramethylfluthrin), tetramethrin (tetramethrin),Tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralomethrin, transfluthrin, triazamate, triazophos, trichlorfon, Trichoderma asperellum, Trichoderma paecilomyces, Trichoderma hartianum harzianum, triflumuron, trifluenfuronate, triflumezopyrim, trimethacarb, tolfenpyrad, naled, nicotine, nicofluprole, nitenpyram, nemadectin, Denso virus, novaluron, noviflumuron, Paecilomyces lilacinus, Burkholderia cepacia, Burkholderia rinojensis, Verticillium lecanii lecanii), hydroprene, Pasteuria nishizawae, Pasteuria penetrans, Bacillus amyloliquefaciens, Bacillus firmus, 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 Bacillus popilliae, Bacillus licheniformis, vadescana, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bioallethrin, bioallethrin S-cyclopentenyl S-cyclopentenyl, pioxaniliprole, bioresmethrin, bis-(2-chloro-1-methylethyl) ether (DCIP), bistrifluron, bisulfuron, hydramethylnon, bifenazate, bifenthrin, pyflubumide, piperflanilide, piperonyl butoxidebutoxide, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins thrine, famphur, fipronil, fenazaquin, fenamiphos, fenitrothion, fenoxycarb, fenothiocarb, phenothrin [including the (1R)-trans-isomer], fenobucarb, fenthion, phenthoate, fenvalerate, fenpyroximate, fenbutantin oxide oxide, fenpropathrin, fenmezoditiaz, fonofos, sulfuryl fluoride, butocarboxim, butoxycarboxim, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazuron, fluensulfone, fluopyram, fluoroacetic acid sodium saltfluoroacetate, fluxametamide, fluclodiniliprole, flucycloxuron, flucythrinate, fluthrin, fluvalinate [including tau-form], flupyradifurone, flupyrazofos, flupyrimin, flupyroxystrobin, flufiprole, flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flupe Flupentiofenox, flumethrin, fluralaner, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite, prohydrojasmon, profenofos, broflanilide, profluthrin, propetamphos, propoxur, flometoquin, bromopropylate, hexythiazox, hexaflumuron, and pekiromyces Pacilimyces tenuipes, Paecilomyces fumosoroceus, Paecilomyces lilacinaslilacinus, heptafluthrin, heptenophos, permethrin, benclothiaz, benzpyrimoxan, bensultap, benzoximate, bendiocarb, benfuracarb, Pochonia chlamydosporia, Beauveria tenella, Beauveria bassiana, Beauveria brongniartii brongniartii, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosmet, polynactins, formetanate, phorate, machine oil, malathion, mivorilaner, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metham, methiocarb, methidathion, methyl isothiocyanate isothiocyanate), methyl bromidebromide, methoxychlor, methoxyfenozide, methotrin, metofluthrin, methoprene, metolcarb, mevinphos, meperfluthrin, modoflaner, Monacrosporium phymatophagum, monocrotophos, momfluorothrin, Trichoderma harzianum, litlure-A, litlure-B, aluminum phosphide, zinc phosphide phosphide, hydrogen phosphide (phosphine), lufenuron, rescale, resmethrin, lepimectin, rotenone, cytoplasmic polyhedrosis virus, fenbutatin oxide, calcium nitrogencyanide), organotin compounds (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 acetate, (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 proteins (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34) / 35Ab1), methyleugenol, 4-(p-acetoxyphenyl)-2-butanone, (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, 14-methyl-1-octadecene, AKD-1193 (code number), BCS-A A10147 (code number), CL900167 (code number), O,O-Diethyl-O-[4-(dimethylsulfamoyl)phenyl]-phosphorothioate (DSP), O-Ethyl-O-4-(nitrophenyl)phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosen-10-one, ZXI8901 (code number), F4260 (code number).

[0214] Next, known herbicidal compounds, herbicidal active ingredients and plant growth regulator compounds that may be mixed or used in combination will be exemplified below, but the present invention is not limited to these examples.

[0215] Herbicide compounds or herbicidal active ingredients: Ioxynil (including its lithium salt, sodium salt, and salts with octanoic acid, etc.), aclonifen, acrolein, azafenidin, acifluorfen (including its sodium salt, 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, isoxaflutole, isoxaben, isodecylalkoholethoxylate, isoproturon, ipfencarbazone arbazone), 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, ethoxyfen-ethyl Ethoxyfen-ethyl, ethofumesate, etobenzanid, epirifenacil, endothal disodium, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxyfluorfen, oryzalin, and ovuda Obuda Pepper Virus, orthosulfamuron, orbencarb, oleic acid, cafenstrole, caprylic acid, capric acid, carfentrazone-ethyl, karbutilate, carbetamide, quizalofop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, Xanthomonas campstris campestris), quinoclamine, quinclorac, quinmerac, citric acid, cumyluron, clacyfos,Glyphosate (including its salts such as sodium, potassium, amine, propylamine, isopropylamine, ammonium, isopropylammonium, guanidine, monoethanolamine, choline, BAPMA (N,N-bis-(aminopropyl)methylamine), dimethylamine, or trimesium), glufosinate (including its salts such as amine or sodium), glufosinate-P, glufosinate-P-sodium, clethodim, clodinafop, clodinafop-propargyl, clopyralid (including its monoethanolamine salt), clomazone, chlomethoxyfen, clomeprop eprop, cloransulam-methyl, chloramben, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, chlorphthalim, chlorflurenol-methyl, chlorpropham, chlorbromuron, chloroxuron, chlorotoluron, ketospiradox (including salts such as sodium, calcium, or ammonia), colletotricham Colletotrichum orbiculare, Colletotrichum gloeosporioides, Colletotrichum truncatum, Chondrostercum purpureum,Saflufenacil, sarmentine, cyanazine, cyanamide, diuron, diethathyl-ethyl, dioxopyritrione, dicamba (amine, diethylamine, isopropylamine, diglycolamine, dimethylammonium, diolamine, isopropylammonium, olamine, potassium, trolamine, BAPMA (N,N-bis-(aminopropyl)methylamine), choline, salts such as sodium or lithium, or esters such as methyl ester), cycloate, cycloxydim, diclos diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlobenil, diclofop, diclofop-P-methyl, diclofop-methyl, dichlorprop, dichlorprop-P (including dimethylammonium, potassium, sodium, choline salts, etc., or esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester), diquat, diquat dibromide dibromide, dithiopyr, siduron, dinitramine, cinidon-ethyl, cinosulfuron, dinozeb (including acetate), dinoterb, cyhalofop, cyhalofop-butyl, cypyrafluone, diphenamid, difenzoquat, diflufenican,Diflufenzopyr, simazine, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, simetryn, dimepiperate, dimefuron, Pseudomonas fluorescens fluorescens, cinflubrolin, cinmethylin, swep, sulcotrione, sulfentrazone, sulfosate, sulfosulfuron, sulfometuron-methyl, sethoxydim, Sclerotinia minor, terbacil, daimuron, thaxtomin A, Tobacco Mild Green Mosaic Tobamovirus, Tobacco Rattle Virus Virus), dalapon, thiazopyr, thiafenacil, thiencarbazone (including sodium salt, methyl ester, etc.), thiocarbazil, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryne, tetflupyrolimet, Thenylchlor, tebutam, tebuthiuron, tepraloxydim, tefuryltrione, terbuthylazine, terbutryn, terbumeton, tembotrione, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, triclopyr, triclopyr-butotyl, triclopyr-triethylan monium (triclopyr-triethylammonium), tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron-methyl, trifluralin, trifloxysulfuron (including salts with sodium etc.), tribenuron-methyl, tolpyralate, naptalam (including salts with sodium etc.), naproanilide, napropamide, napropamide-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, trollamine, etc.), picolinafen, bicyclopyrone, bispyribac-sodium, pinoxaden, bipyrazone, bifenox, piperophos, pyraclonil, pyrasulfothol ole, pyrazoxyfen, pyrazosulfuron-ethyl, pyrazolynate, bilanafos, pyraflufen, pyraflufen-ethyl, pyraquinate, pyridafol, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyriminobac-methyl, pyroxasulfone, pyroxsulam, phytopsora Palmivora (Phytophthora palmivora), phenisopham, fenuron, fenoxasulfone, fenoxaprop (methyl, ethyl,isopropyl ester), fenoxaprop-P (including methyl, ethyl, and isopropyl esters), feproxydim, fenquinotrione, fenthiaprop-ethyl, fentrazamide, fenpyrazone, phenmedipham, Phoma chenopodicola, Phoma herbarum, Phoma macrostoma, butachlor, butafenacil, butamifos, butyrate, Puccinia canaliculata, Puccinia sraspeos thlaspeos, butenachlor, butralin, butroxydim, flazasulfuron, flamprop (including methyl, ethyl, and isopropyl esters), flamprop-M (including methyl, ethyl, and isopropyl esters), primisulfuron, primisulfuron-methyl, fluazifop-butyl, fluazifop-butyl, Fluazifop-P, fluazifop-P-butyl, fluazolate, fluometuron, fluoroglycofen-ethyl, flucarbazone-sodium, fluchloraminopyr, fluchloralin, flucetosulfuron, flusulfinam,Fluthiacet-methyl, flupyrsulfuron-methyl (including salts such as sodium, calcium, or ammonia), flufenacet, flufenoximacil, flufenpyr-ethyl, flupropanate (including sodium salt), flupoxame, flumioxazin, flumic Flumiclorac-pentyl, flumetsulam, fluridone, flurtamone, fluroxypyr (including esters such as butmethyl and meptyl, or salts with sodium, calcium, ammonia, etc.), flurochloridone, pretilachlor, procarbazone (including salts with sodium, etc.), broclozone zone, prodiamine, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, propyrisulfuron, propham, profluazol ), prohexadione calcium salt, propoxycarbazone, propoxycarbazone sodium salt, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil (including esters of butyric acid, octanoic acid or heptanoic acid, etc.),Bromofenoxim, bromobutide, florasulam, florpyrauxifen, florpyrauxifen-benzyl, hexazinone, pethoxamid, 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 luralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, mecoprop (including salts of sodium, potassium, isopropylamine, triethanolamine, dimethylamine, diolamine, tetrolamine, choline, etc., or esters such as etadyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester), mecoprop-P-potassium salt (mecoprop-P-potassium), Mesosulfuron (including esters such as methyl), mesotrione, metazachlor, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam (including salts such as sodium), disodium methanarsonate (DSMA), methiozoline lin), 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) (including 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) (including salts of amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, diolamine, dodecylammonium, heptylammonium, tetradecylammonium, triethylammonium, tris(2-hydroxypropyl)ammonium, tetrolamine, choline, sodium or lithium, 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), 2,4-dichlorophenoxybutyric acid (2,4-DB) (including salts of amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, choline, sodium or lithium, etc. or its esters such as isoctyl ester), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (including its salts such as sodium, dimethylammonium, choline, or its esters such as 2-ethylhexyl ester, isoctyl ester, ethyl ester), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including its sodium salt, ethyl ester, etc.), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 4,6-dinitro-O-cresol (DNOC) (including its salts such as amine or sodium), N4-(2,6-difluorophenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine4-diamine) (chemical name, CAS registration number: 1606999-43-2) (WO 2014 / 064094, WO 2015 / 162164), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (chemical name, CAS registration number: 1606999-43-2) (WO 2014 / 064094, WO 2015 / 162164), Name, CAS Registry Number: 1708087-22-2) (WO 2015 / 059262, WO 2018 / 015476), 6-(1-fluorocyclopentyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine iamine) (chemical name, CAS registration number: 1820807-75-7) (WO 2015 / 162164), 6-(1-fluoro-1-methylethyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine ne) (chemical name, CAS registration number: 1606999-21-6) (WO 2014 / 064094, WO 2015 / 162164), 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-2,4-diamine) (chemical name, CAS registration number: 1607001-97-7) (WO 2014 / 064094, WO 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, HW-02 (code number).

[0216] Plant growth regulators: 1-naphthylacetamide, 1-methylcyclopropene, 1,3-diphenylurea, 2,3,5-triiodobenzoic acid acid), 2-methyl-4-chlorophenoxybutyric acid (MCPB) [including sodium salt, ethyl ester, etc.], 2-(naphthalene-1-yl)acetamide, 2,6-diisopropylnaphthalene, 3-[(6-chloro-4-phenylquinazolin-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, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate 5-(trifluoromethyl)benzo[b]thiofen-2-carboxylate, AVG (aminoethoxyvinylglycine), n-decyl alcohol (n-decanol), anisiflupurin, aviglycine, ancymidol, abscisic acid, isoprothiolane, inabenfide, indole acetic acid, indole butyric acid, uniconazole, uniconazole-P, Ecolyst, ethychlozate, 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 (including salts such as dimethylammonium, potassium, sodium, and choline, or esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, and methyl ester), dichlorprop-P (including salts such as sodium, potassium, and dimethylammonium, or 2-ethylhexyl ester), diquat, diquat dibromide, dikegulac, gibberellic acid, gibberellin A4, gibberellin A7, dimethipin, sintophen, jasmone, cis-jasmone, jasmonic acid, and methyl jasmonate jasmonate, streptomycin, calcium sulfur (calcium polysulfide), daminozide, calcium carbonate (calciumcarbonate, thidiazuron, decan-1-ol, triacontanol, triapenthenol, 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.

[0217] Next, examples of known safening compounds that may be used in admixture or combination are given below.

[0218] Safener compounds: Isoxadifen, isoxadifen-ethyl, oxabetrinil, octane-1,8-diamine, cloquintocet, cloquintcet-mexyl, dietholate, cyometrinil, dichlormid, dicyclonone, cyprosulfamide, daimuron, naphthalic anhydride Anhydride, fenchlorazole, fenchlorazole-O-ethyl, fenclorim, furilazole, fluxofenim, flurazole, benoxacor, metcamifen, mephenate, mefenpyr, mefenpi Mefenpyr-ethyl, mefenpyr-diethyl, lower alkyl substituted benzoic acids, 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), metcamifen, 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-carbodithioate (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).

[0219] Next, examples of known biological pesticides that may be mixed or used in combination are listed below.

[0220] Biopesticides: Haplothrips brevitubus, Franklinothrips vespiformis, Diglyphus isaea, Encarsia formosa, Amblyseius cucumeris, Pseudaphycus malinus, Amblyseius womersleyi, Aphidius colemani, Eretmocerus eremicus, Aphidoletes aphidimyza, Amblyseius swirskii, Orius strigiformes strigicollis, Phytoseiulus persimilis, Amblyseius degenerans, Phytoseiulus persimilis, Orius sauteri, Dacnusa sibirica, Amblyseius californicus, Chrysoperla nipponensis, and Anicetus beneficus.

[0221] Next, examples of known agricultural materials that may be mixed or used in combination are listed below.

[0222] Agricultural supplies: Ethylene, hypochlorous acid water (limited to that obtained by electrolyzing hydrochloric acid or potassium chloride aqueous solution), baking soda, vinegar, humus, humic acid, fulvic acid, seaweed extract, polysaccharides, amino acids, microbial materials, functional ingredients derived from plants and animals, microbial metabolites, microbial activating materials, soil spreading agents, soil permeability adjusting materials, soil water retention materials, etc., and biostimulants.

[0223] Next, examples of known agricultural fertilizer components that may be mixed or used in combination are listed below. Fertilizers include inorganic fertilizers and organic fertilizers.

[0224] Agricultural fertilizer ingredients: Ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, ammonium urea nitrate, urea, lime nitrogen, potassium nitrate, superphosphate, triple superphosphate, potassium dihydrogen phosphate, potassium phosphite, potassium chloride, potassium sulfate, potassium carbonate, potassium silicate, oil cake, fish meal, rice bran, bat guano, fermented chicken manure.

[0225] Specific examples of diseases that can be controlled by the agricultural and horticultural plant disease control agent and agricultural and horticultural plant disease control method of the present invention are given below, but the invention is not limited to these examples.

[0226] Basidiomycota: Rice sheath blight (Thanatephorus cucumeris); wheat rust (Puccinia recondite, Puccinia graminis, Puccinia hordei, Puccinia striiformis), snow mold (Typhula incarnata, Typhula ishikariensis), naked smut (Ustilago tritici, Ustilago nuda), cattail smut (Tilletia spp.); grape rust (Phakopsora meliosmae-myrianthae, Phakopsora montana, Physopella ampelopsidis); apple red scab (Gymnosporangium yamadae); pear red scab (Gymnosporangium asiaticum); seedling damping-off of cucumbers, tomatoes, etc. (Rhizoctonia solani); onion rust (Puccinia allii, Uromyces allii-monanthi, Uromyces japonicus), black rot (Sclerotium cepivorum); soybean rust (Phakopsora pachyrhizim, Phakopsora meibomiae); potato black spot (Rhizoctonia sp., Thanatephorus cucumeris); tea net blight (Exobasidium reticulatum); chrysanthemum white rust (Puccinia horiana); turfgrass leaf rot (Rhizoctonia solani), rust (Puccinia zoysiae), fairy ring (Marasmius oreades, etc.); sugar beet root rot (Thanatephorus cucumeris) Ascomycota: Rice blast (Pyricularia oryzae), Sesame leaf blight (Cochliobolus miyabeanus), Gibberella fujikuroi, Seedling damping off (Fusarium avenaceum, Fusarium proliferatum, Fusarium solani, Trichoderma viride), Rice mildew (Villosiclava virens); Wheat powdery mildew (Blumeria) graminis f. sp. Hordeii, Blumeria graminis f. sp. tritici), Pyrenophora graminea, Pyrenophora teres, Fusarium asiaticum, Fusarium avenaceum, Fusarium crookwellense, Fusarium culmorum, Gibberella zeae, Microdochium majus,Microdochium nivale), Myriosclerotinia borealis, Microdochium nivale, Oculimacula acuformis,Oculimacula yallundae, Rhynchosporium secalis f. sp. hordei, Zymoseptoria tritici, Phaeosphaeria nodorum); grape powdery mildew (Erysiphe necator var. necator), black rot (Elsinoe ampelina), late rot (Colletotrichum aenigma, Colletotrichum fioriniae, Colletotrichum fructicola, Colletotrichum gloeosporioides s. str.), black rot (Guignardia bidwellii), fusarium wilt (Phomopsis viticola), brown spot (Pseudocercospora vitis); apple powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), leaf spot (Alternaria mali), Monilinia mali, canker (Valsa ceratosperma), ring spot (Botryosphaeria kuwatsukai), brown rot (Monilinia fructicola, Monilinia fructigena), brown spot (Diplocarpon mali), anthracnose (Colletotrichum aenigma, Colletotrichum fioriniae, Colletotrichum fructicola, Colletotrichum godetiae), black spot (Mycosphaerella pomi), sooty spot (Gloeodes pomigena), sooty spot (Zygophiala jamaicensis); pear black spot (Alternaria kikuchiana), black scab (Venturia nashicola), brown spot (Mycosphaerella pyri), canker (Phomopsis fukushii), anthracnose (Colletotrichum fioriniae, Glomerella cingulata); peach brown scab (Monilinia fructicola, Monilinia fructigena), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.); persimmon anthracnose (Colletotrichum horii), angular leaf spot (Cercospora kaki), circular leaf spot (Mycosphaerella nawae); citrus black spot (Diaporthe citri, Diaporthe spp.), common scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum); cucurbit powdery mildew (Golovinomyces cucurbitacearum, Leveillula taurica, Podosphaera xanthii), anthracnose (Colletotrichum orbiculare), vine wilt (Didymella bryoniae), vine split (Fusarium oxysporum f. sp. cucumerinum), brown spot (Corynespora cassiicola), gray mold (Botrytis cinerea), Phomopsis root rot (Phomopsis sp.); tomato ring spot (Alternaria linariae, Alternaria solani), anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides, Colletotrichum nigrum), leaf mold (Fulvia fulva), verticillium wilt (Verticillium dahliae), wilt (Fusarium oxysporum f. sp. lycopersici); eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Podosphaera xanthii), black blight (Corynespora cassiicola), soybean leaf mold (Mycovellosiella nattrassii); rapeseed sclerotinia (Sclerotiorum); cruciferous crops black spot (Alternaria brassicae), white spot (Pseudocercosporella capsellae, Cercosporella brassicae), soybean sclerotinia (Sclerotinia sclerotiorum), purple spot (Cercospora kikuchii), black rot (Elsinoe) glycines), black spot (Diaporthe phaseolorum var.sojae), brown ring spot (Corynespora cassiicola); kidney bean anthracnose (Colletotrichum lindemuthianum); peanut black spot (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis, Cercospora canescens); pea powdery mildew (Erysiphe pisi); potato summer blight (Alternaria solani); tea white spot (Elsinoe leucospila), anthracnose (Gloeosporium theae-sinensis), ring spot (Neopestalotiopsis spp., Pestalotiopsis longiseta, Pestalotiopsis theae); tobacco red spot (Alternaria alternata), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum gloeosporioides; sugar beet powdery mildew (Oidium sp.), brown spot (Cercospora beticola); rose scab (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa); chrysanthemum brown spot (Septoria obesa); strawberry powdery mildew (Podosphaera aphanis var. aphanis), anthracnose (Colletotrichum gloeosporioides, Colletotrichum acutatum, Glomerella cingulata, Colletotrichum aenigma, Colletotrichum fioriniae, Colletotrichum fragariae, Colletotrichum fructicola, Colletotrichum nymphaeae, Colletotrichum siamense); banana black sigatoka (Mycosphaerella fijiensis), yellow sigatoka (Mycosphaerella musicola), Panama disease (Fusarium oxysporum, Fusarium oxysporum f. sp.cubense); Botrytis cinerea and Sclerotinia sclerotiorum of cucumbers, tomatoes, beans, strawberries, grapes, etc.; Dollar spot of turfgrass (Clarireedia jacksonii, Clarireedia monteithiana), Curvularia geniculata, Gaeumannomyces graminis, and Colletotrichum caudatum. Subphylum Mucoromycotina: Rice seedling damping-off (Rhizopus chinensis, Rhizopus oryzae) Oomycota: Rice seedling damping-off (Pythium spp.); wheat brown snow rot (Pythium iwayamai, Pythium paddicum, Pythium horinouchiense, Pythium graminicola, Pythium okanoganense); grape downy mildew (Plasmopara viticola); citrus brown rot (Phytophthora citricola, Phytophthora citrophthora, Phytophthora nicotianae, Phytophthora palmivora, Phytophthora syringae); pear late blight (Phytophthora cactorum, Phytophthora syringae); peach late blight (Phytophthora sp.); cucurbit downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora melonis, Phytophthora nicotianae), seedling damping-off (Pythium cucurbitacearum, Pythium debaryanum; tomato, eggplant, and potato late blight (Phytophthora infestans), seedling damping-off (Pythium vexans), and root rot (Pythium aphanidermatum, Pythium myriotylum, Pythium dissotocum); onion white rot (Phytophthora porri); soybean stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica); pea downy mildew (Peronospora pisi); sugar beet downy mildew (Peronospora schachtii), black root rot (Aphanomyces cochlioides); strawberry late blight (Phytophthora cactorum, Phytophthora fragariaefolia, Phytophthora nicotianae, Phytophthora sp.), and fruit rot (Pythium ultimum var. ultimum); Pythium disease of turfgrass (Pythium periplocum, Pythium graminicola, Pythium vanterpoolii) Bacteria: Rice seedling bacterial disease (Burkholderia plantarii), bacterial leaf blight (Xanthomonas oryzae pv. oryzae), bacterial grain rot (Burkholderia gladioli, Burkholderia glumae), brown stripe (Acidovorax avenae subsp. avenae), brown lemma disease (Pantoea ananatis); peach bacterial hole (Brenneria nigrifluens, Pseudomonas syringae pv. syringae, Xanthomonas arboricola pv. pruni); citrus canker (Xanthomonas citri subsp. citri); cucurbit bacterial spot (Pseudomonas syringae pv. lachrymans); tomato canker (Clavibacter michiganensis subsp. michiganensis); potato common scab (Streptomyces spp.); tea red blight (Pseudomonas syringae pv. theae); bacterial wilt of tomatoes, potatoes, etc. (Ralstonia solanacearum); soft rot of Chinese cabbage, leeks, onions, etc. (Pectobacterium carotovorum) Cercozoa: Clubroot disease of cruciferous crops (Plasmodiophora brassicae), etc.

[0227] The agricultural and horticultural plant disease control agent of the present invention also exhibits a control effect against the above-exemplified plant diseases that have acquired resistance to existing agricultural and horticultural plant disease control agents. The agricultural and horticultural plant disease control agent of the present invention can also be used for plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance through new breeding techniques such as genetic recombination and genome editing, artificial crossbreeding, etc.

[0228] The "plants to which resistance has been imparted by breeding or genetic engineering" of the present invention include not only plants to which resistance has been imparted by classical breeding or genetic engineering, but also plants to which resistance has been imparted by new plant breeding techniques (NBTs), which combine conventional breeding techniques with molecular biological methods. New breeding techniques (NBTs) are described in the book "Understanding New Plant Breeding Techniques" (Kokusai Bunkensha, Ryo Osawa and Hiroshi Ezura) and the review article "Genome Editing Tools in Plants" (Genes 2017, 8, 399, Tapan Kumar Mohanta, Tufail Bashir, Abeer Hashem, Elsayed Fathi Abd Allah and Hanhong Bae), among others.

[0229] Next, the manufacturing method, formulation method, and uses of the compound of the present invention will be explained in detail in the following examples, but the present invention is not limited to these examples. The melting point, which is a physical property value 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 H NMR spectra were measured using a JNM-LA400 (400 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL Ltd., with tetramethylsilane (TMS) as an internal standard.

[0230] Also described are methods for producing intermediates for the compounds of the present invention. [Example 1] Preparation of N-(3,3-dimethyl-2-oxobutyl)-N-{4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propionylamide (compound of the present invention: A-0008)

[0231] (1) Preparation of N-(4-cyanophenyl)propioamide 2.00 g (16.9 mmol) of 4-aminobenzonitrile was dissolved in 10 mL of pyridine, and 1.65 g (17.8 mmol) of propionyl chloride was added under ice-cooling and stirred for 4 hours. After the reaction was completed, ice water was added and the precipitated crystals were collected by filtration, washed with water, and dried under reduced pressure to obtain 2.15 g (73% yield) of the target compound.

[0232] 1 H-NMR data (300MHz, CDCl3 / TMSδ(ppm)):7.68-7.59(4H,m),7.35(1H,bs),2.44(2H,q),1.26(3H,t)

[0233] (2) Preparation of N-(4-cyanophenyl)-N-(3,3-dimethyl-2-oxobutyl)propionylamide 200 mg (1.15 mmol) of N-(4-cyanophenyl)propioamide and 636 mg (1.95 mmol) of cesium carbonate were dissolved in 5 mL of N,N-dimethylformamide, 308 mg (1.72 mmol) of 1-bromo-3,3-dimethyl-2-butanone was added, and the mixture was stirred at room temperature for 24 hours. After the reaction was completed, aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:1) to obtain 160 mg of the target compound (yield 51%).

[0234] 1 H-NMR data (300MHz, CDCl3 / TMSδ(ppm)): 7.71(2H,d), 7.47(2H,d), 4.58(2H,s), 2.15(2H,q), 1.20(9H,s), 1.07(3H,t)

[0235] (3) Preparation of N-(3,3-dimethyl-2-oxobutyl)-N-[4-(N'-hydroxycarbamidoyl)phenyl]propioamide 0.29 g (1.06 mmol) of N-(4-cyanophenyl)-N-(3,3-dimethyl-2-oxobutyl)propionylamide and 148 mg (2.09 mmol) of hydroxylamine hydrochloride were dissolved in 20 mL of ethanol, 229 mg (1.06 mmol) of triethylamine was added, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the mixture was allowed to cool to room temperature, and the ethanol was removed under reduced pressure. Water and ethyl acetate were then added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 260 mg of the target compound (80% yield).

[0236] 1 H-NMR data (300MHz, DMSO-d6 / TMSδ(ppm)): 9.69(1H,bs), 7.70(2H,d), 7.31(2H,d), 5,85(2H,bs), 4.62(2H,bs), 2.08(2H,q), 1.10(9H,s), 0.91(3H,t)

[0237] (4) Preparation of N-(3,3-dimethyl-2-oxobutyl)-N-{4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propionylamide (Compound of the Present Invention: A-0008) 260 mg (0.85 mmol) of N-(3,3-dimethyl-2-oxobutyl)-N-[4-(N'-hydroxycarbamidoyl)phenyl]propioamide was dissolved in 10 mL of THF, 197 mg (0.97 mmol) of trifluoroacetic anhydride was added, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the trifluoroacetic anhydride and solvent were distilled off under reduced pressure, and ethyl acetate was added to the reaction mixture. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (developing solvent, n-hexane:ethyl acetate = 3:1) to obtain 247 mg of the target compound (yield 76%).

[0238] 1H-NMR data (400MHz, CDCl3 / TMSδ(ppm)): 8.14(2H,d), 7.49(2H,d), 4.60(2H,s), 2.18(2H,q), 1.19(9H,s), 1.06(3H,t)

[0239] [Example 2] Preparation of N-[(methylsulfonyl)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}acetamide (compound of the present invention: A-0108)

[0240] (1) Preparation of tert-butyl N-[(methylthio)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate 3.00 g (9.11 mmol) of tert-butyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, prepared by the method described in WO 2007 / 111212, was dissolved in 15 mL of N,N-dimethylformamide. 437 mg of sodium hydride (purity: approximately 55%, 10.0 mmol) was added under ice cooling. After stirring for 0.5 hours, 924 mg (9.57 mmol) of chlorodimethyl sulfide was added under ice cooling. The mixture was warmed to room temperature and stirred for 19 hours. After completion of the reaction, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure to obtain 2.30 g of the target compound (70% yield).

[0241] 1 H-NMR data (300MHz, CDCl3 / TMSδ(ppm)): 8.12(2H,d), 7.46(2H,d), 4.86(2H,s), 2.18(3H,s), 1.46(9H,s)

[0242] (2) Preparation of N-[(methylthio)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}aniline 2.30 g (4.13 mmol) of t-butyl N-[(methylthio)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate was dissolved in 20 mL of dichloromethane, and 6.30 mL (62.7 mmol) of trifluoroacetic acid was added under ice cooling. The mixture was stirred for 2 hours under ice cooling. After the reaction was completed, 200 mL of saturated aqueous sodium bicarbonate and dichloromethane were added under ice cooling. The organic layer was washed with water, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 650 mg of the target compound (yield 54%).

[0243] 1 H-NMR data (300MHz, CDCl3 / TMSδ(ppm)): 7.95(2H,d), 6.78(2H,d), 4.64(1H,bs), 4.42(2H,d), 2.17(3H,s)

[0244] (3) Preparation of N-[(methylsulfonyl)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}acetamide 320 mg (1.11 mmol) of N-[(methylthio)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}aniline was dissolved in 7 mL of pyridine, 261 mg (3.32 mmol) of acetyl chloride was added, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, 1 M aqueous hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 250 mg (68% yield) of the target compound. 1 H-NMR data (300MHz, CDCl3 / TMSδ(ppm)): 8.22(2H,d), 7.45(2H,d), 4.89(2H,s), 2.19(3H,s), 1.94(3H,s)

[0245] (4) Preparation of N-[(methylsulfonyl)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}acetamide (Compound of the Present Invention: A-0108) 260 mg (0.79 mmol) of N-[(methylsulfonyl)methyl]-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}acetamide was dissolved in 10 mL of dichloromethane, and 460 mg (2.35 mmol) of metachloroperbenzoic acid was added under ice cooling. The mixture was stirred for 7 hours under ice cooling. After the reaction was completed, aqueous sodium thiosulfate solution was added and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:1) to obtain 270 mg (91% yield) of the target compound.

[0246] 1 H-NMR data (300MHz, CDCl3 / TMSδ(ppm)): 8.22(2H,d), 7.55(2H,d), 4.96(2H,s), 3.08(3H,s), 2.00(3H,s)

[0247] The physical properties of the compound [I] of the present invention synthesized according to the above examples (melting point, refractive index and 1 H-NMR spectral data, including the values ​​in the above examples, are shown in the following Tables 8 and 9. The compound numbers and symbols in the tables have the same meanings as above.

[0248] [Table 8]

[0249] [Table 9]

[0250] Next, specific examples of formulations of the agricultural and horticultural plant disease control agent of the present invention using the aryloxadiazole compound or its salt of the present invention produced as described above will be described. However, the types and blending ratios of the compounds and additives are not limited to these and can be changed within a wide range. In the following description, "parts" means parts by mass.

[0251] [Formulation Example 1] Emulsion 10 parts of each compound listed in Tables 1 to 9 30 parts cyclohexanone Polyoxyethylene alkyl aryl ether 11 parts Calcium alkylbenzene sulfonate 4 parts Methylnaphthalene 45 parts The above ingredients were dissolved uniformly to prepare an emulsion.

[0252] [Formulation Example 2] Wettable powder 10 parts of each compound listed in Tables 1 to 9 Naphthalenesulfonic acid formalin condensate sodium salt 0.5 parts Polyoxyethylene alkyl aryl ether 0.5 parts 24 parts diatomaceous earth Clay 65 parts The above ingredients were uniformly mixed and pulverized to give wettable powders.

[0253] [Formulation Example 3] Powder 2 parts of each compound listed in Tables 1 to 9 5 parts diatomaceous earth Clay 93 parts The above ingredients were uniformly mixed and pulverized to prepare a powder.

[0254] [Formulation Example 4] Granules 5 parts of each compound listed in Tables 1 to 9 Sodium lauryl alcohol sulfate 2 parts Sodium lignosulfonate 5 parts Carboxymethylcellulose 2 parts Clay 86 parts The above ingredients were mixed and pulverized to a uniform consistency. To this mixture was added 20 parts of water, which was then kneaded and processed into 14 to 32 mesh granules using an extrusion granulator, which were then dried to give granules.

[0255] [Formulation Example 5] Flowable formulation 20 parts of each compound listed in Tables 1 to 9 Polyoxyethylene styrenated phenyl ether sulfate 4 parts 7 parts ethylene glycol Silicone AF-118N (Asahi Chemical Industry Co., Ltd.) 0.02 parts Wednesday 68.98 parts The above ingredients were mixed for 30 minutes using a high-speed mixer, and then pulverized using a wet pulverizer to prepare a flowable formulation.

[0256] [Formulation Example 6] Water dispersible granule 10 parts of each compound listed in Tables 1 to 9 Sodium lignosulfonate 5 parts Polyoxyethylene alkyl aryl ether 1 part Sodium polycarboxylate 3 parts White carbon 5 parts 1 part pregelatinized starch 65 parts calcium carbonate 10 parts water The above ingredients were mixed, kneaded, and granulated. The resulting granules were dried in a fluidized bed dryer to obtain water dispersible granules.

[0257] Next, the effects of the disease control agent of the present invention will be explained using test examples.

[0258] [Test Example 1] Test of soybean rust (Phakopsora pachyrhizi) control effect Soybean seeds were sown in pots, and the grown seedlings were sprayed with a solution containing 300 g of active ingredient a day (ai / ha). They were then spray-inoculated with soybean rust fungus, transferred to a moist chamber, and maintained in darkness to promote pathogen penetration. After that, the plants were kept in a greenhouse, and the disease severity on each first leaf was indexed according to the criteria in Table 10 below after 12-14 days. The disease severity was calculated using the formula shown as Number 1, and the control value was calculated using the formula shown as Number 2.

[0259] [Table 10]

[0260] [Number 1] Severity = (n0 x 0 + n1 x 1 + n2 x 2 + n3 x 3 + n4 x 4) / 4N x 100

[0261] [In the formula, N represents the total number of investigated leaves, n0 represents the number of leaves with a disease index of 0, n1 represents the number of leaves with a disease index of 1, n2 represents the number of leaves with a disease index of 2, n3 represents the number of leaves with a disease index of 3, and n4 represents the number of leaves with a disease index of 4.]

[0262] [Number 2] Control value = {1 - (disease severity in treated area / disease severity in untreated area)} x 100

[0263] As a result of the test, A-0007 and A-0087 had a control value of 60 or more but less than 80, while A-0001, A-0002, A-0004, A-0025, A-0026, A-0027, A-0028, A-0029, A-0030, A-0032, A-0035, A-0066, A-0067, A-0103, A-0104, A-0142, A-0143, A-0145, and A-0146 had a control value of 80 or more. [Industrial Applicability]

[0264] The present invention provides a plant disease control agent containing, as an active ingredient, a novel aryloxadiazole compound or a salt thereof that has a high control effect against plant diseases caused by pathogenic fungi, and is useful in the fields of pesticides and agriculture, and has industrial applicability.

Claims

1. General formula [I] 【Chemical 1】 [In the formula, A １ , A ２ , A ３ , and A ４ are each independently a nitrogen atom, CH, or C—R ４ indicates, Y represents an oxygen atom or a sulfur atom; X represents a hydrogen atom or a halogen atom; Z is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ Cycloalkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ３ ~C ６ Cycloalkyloxy C １ ~C ６ Alkyl group, 3- to 6-membered heterocyclyloxy C １ ~C ６ alkyl group (the 3- to 6-membered heterocyclyl group is R ５ substituents), C ６ ~C １２ Aryloxy C １ ~C ６ Alkyl group (the C ６ ~C １２ The aryl group is R ５ substituted with one or more substituents selected from the group consisting of 5- to 12-membered heteroaryloxy C １ ~C ６ alkyl group (the 5- to 12-membered heteroaryl group is R ５ substituents), C １ ~C ６ Alkylamino C １ ~C ６ alkyl group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ６ Cycloalkylamino C １ ~C ６ alkyl group (the amino group is R ６ and 3- to 6-membered heterocyclylamino C １ ~C ６ alkyl group (the 3- to 6-membered heterocyclyl group is R ５ The amino group may be substituted with one or more substituents selected from R ６ may be substituted with a substituent selected from ６ ~C １２ Arylamino C １ ~C ６ Alkyl group (the C ６ ~C １２ The aryl group is R ５ The amino group may be substituted with one or more substituents selected from R ６ and 5- to 12-membered heteroarylamino C １ ~C ６ alkyl group (the 5- to 12-membered heteroaryl group is R ５ The amino group may be substituted with one or more substituents selected from R ６ may be substituted with a substituent selected from １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C ３ ~C ６ Cycloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C ３ ~C ６ Cycloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ６ Cycloalkylsulfonyl C １ ~C ６ Alkyl group, amino group, monoformylamino group, C １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ６ A cycloalkylamino group (the amino group is R ６ a 3- to 6-membered heterocyclylamino group (which may be substituted with a substituent selected from R ５ The amino group may be substituted with one or more substituents selected from R ６ may be substituted with a substituent selected from ６ ~C １２ Arylamino group (the C ６ ~C １２ The aryl group is R ５ The amino group may be substituted with one or more substituents selected from R ６ a 5- to 12-membered heteroarylamino group (which may be substituted with a substituent selected from R ５ The amino group may be substituted with one or more substituents selected from R ６ may be substituted with a substituent selected from １ ~C ６ Alkyloxy group, C １ ~C ６ Haloalkyloxy group, C ３ ~C ６ a cycloalkyloxy group, a 3- to 6-membered heterocyclyloxy group (the 3- to 6-membered heterocyclyl group is R ５ substituents), C ６ ~C １２ an aryloxy group (the group is R ５ substituents), a 5- to 12-membered heteroaryloxy group (which may be substituted with one or more substituents selected from R ５ substituents), C １ ~C ６ Alkylthio group, C １ ~C ６ Haloalkylthio group, C ３ ~C ６ Cycloalkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Haloalkylsulfinyl group, C ３ ~C ６ Cycloalkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ６ Cycloalkylsulfonyl group, C ６ ~C １２ an aryl group (the group is R ５ substituents), or a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from R ５ substituents), R １ and R ２ are each independently a hydrogen atom, a cyano group, a halogen atom, or C １ ~C ６ represents an alkyl group, and R １ and R ２ may each form a 3- to 6-membered monocyclic carbocyclic ring together with the carbon atom to which they are attached, and the carbocyclic ring may each be a hydrogen atom, a halogen atom, or C １ ~C ６ may be substituted with an alkyl group, R ３ is a cyano group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C ３ ~C ６ Cycloalkylcarbonyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ３ ~C ６ Cycloalkyloxy C １ ~C ６ Alkyl group, 3- to 6-membered heterocyclyloxy C １ ~C ６ alkyl group (the 3- to 6-membered heterocyclyl group is R ５ substituents), C ６ ~C １２ Aryloxy C １ ~C ６ Alkyl group (the C ６ ~C １２ The aryloxy group is R ５ substituted with one or more substituents selected from the group consisting of 5- to 12-membered heteroaryloxy C １ ~C ６ alkyl group (the 5- to 12-membered heteroaryl group is R ５ substituents), C １ ~C ６ Alkyloxycarbonyl group, C １ ~C ６ Haloalkyloxycarbonyl group, C ３ ~C ６ cycloalkyloxycarbonyl group, C ６ ~C １２ Aryl C １ ~C ６ Alkyloxycarbonyl group (the C ６ ~C １２ The aryl group is R ５ substituted with one or more substituents selected from the group consisting of 5- to 12-membered heteroaryl C １ ~C ６ alkyloxycarbonyl group (the 5- to 12-membered heteroaryl group is R ５ substituents), C １ ~C ６ Alkyloxyimino C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxyimino C １ ~C ６ Alkyl group, C ３ ~C ６ Cycloalkyloxyimino C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Haloalkylthio group, C ３ ~C ６ Cycloalkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Haloalkylsulfinyl group, C ３ ~C ６ Cycloalkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ６ a cycloalkylsulfonyl group, a phenyl group (the group is R ５ substituted with one or more substituents selected from the group consisting of C １０ ~C １２ an aryl group (the group is R ５ substituents), or a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from R ５ substituents), R ４ is a halogen atom or C １ ~C ６ represents an alkyl group, R ５ are each independently a cyano group, an amino group, a nitro group, a hydroxy group, a halogen atom, a thiol group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ Cycloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ alkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyloxy group, C １ ~C ６ Haloalkyloxy group, C ３ ~C ６ Cycloalkyloxy group, C １ ~C ６ Alkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Haloalkylthio group, C ３ ~C ６ Cycloalkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Haloalkylsulfinyl group, C ３ ~C ６ Cycloalkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ haloalkylsulfonyl group, or C ３ ~C ６ represents a cycloalkylsulfonyl group, R ６ is a formyl group, C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, or C ３ ~C ６ [0023] The aryloxadiazole compound or a salt thereof is represented by the formula (1), wherein R represents a cycloalkylcarbonyl group.

2. 10. An agricultural and horticultural plant disease control agent comprising the aryloxadiazole compound or its salt according to claim 1 as an active ingredient.

3. The agricultural and horticultural plant disease control agent according to claim 2 , wherein the plant disease is caused by a pathogenic fungus.

4. The agricultural and horticultural plant disease control agent according to claim 3 , wherein the pathogenic fungus is a Basidiomycete, Ascomycete, Deuteromycete, Oomycete, and / or Zygomycete.

5. 10. An agricultural or horticultural plant disease control composition comprising the aryloxadiazole compound or its salt according to claim 1 and an agriculturally acceptable carrier.

6. A method for controlling diseases of a useful plant, which comprises spraying an effective amount of the aryloxadiazole compound or a salt thereof according to claim 1 onto a useful plant or a part of a useful plant, or onto a place where the useful plant is growing.

7. The method according to claim 6 , wherein the plant disease is caused by a pathogenic fungus.

8. The method according to claim 7, wherein the pathogenic fungus is a Basidiomycete, Ascomycete, Fungi Imperfecti, Oomycete, and / or Zygomycete.

9. Use of the aryloxadiazole compound or a salt thereof according to claim 1 as an agricultural or horticultural plant disease control agent for useful plants.

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