N-oxy-pyrazole-5-carboxamide compound, and plant disease control agent for agricultural and horticultural use using same

Abstract

[Problem] To provide an excellent plant disease control agent for agricultural and horticultural use. [Solution] Provided are: an N-oxy-pyrazole-5-carboxamide compound represented by formula [I] [wherein T represents an oxygen atom or a sulfur atom; R1 represents a hydrogen atom or the like; R2 represents a C1-C6 alkyl group or the like; R3 represents a hydrogen atom, a C1-C6 alkyl group, or the like; R4 and R4' each independently represent a hydrogen atom, a C1-C6 alkyl group, or the like; A represents a C6-C12 aryl group or the like; and Q represents a C6-C12 aryl group or the like] or a salt thereof; and a plant disease control agent for agricultural and horticultural use, which contains the compound or the salt as an active ingredient.

Description

N-oxy-pyrazole-5-carboxamide compound and agricultural and horticultural plant disease control agent using the same

[0001] The present invention relates to a novel N-oxy-pyrazole-5-carboxamide compound or a salt thereof, an agricultural and horticultural plant disease control agent containing the N-oxy-pyrazole-5-carboxamide compound or a salt thereof as an active ingredient, and a production intermediate thereof.

[0002] Patent Document 1 describes pyridazine-4-carboxamide compounds and pyridazine-4-carbothioamide compounds having plant disease control activity.

[0003] Patent Document 2 describes an isonicotinic acid amide compound and a pyridine-4-carbothioamide compound having plant disease control activity.

[0004] Patent Document 3 describes 1,2,4-triazine-5-carboxamide compounds, 1,2,4-triazine-5-carbothioamide compounds, pyrimidine-4-carboxamide compounds, and pyrimidine-4-carbothioamide compounds, which have plant disease control activity.

[0005] Patent Document 4 describes azabicyclocarboxamide compounds and azabicyclocarbothioamide compounds having plant disease control activity.

[0006] Patent Document 5 describes an isonicotinic acid amide compound having plant disease control activity.

[0007] Patent Document 6 describes pyrazole-5-carboxamide compounds and pyrazole-5-carbothioamide compounds having plant disease control activity.

[0008] The above patent documents do not disclose the N-oxy-pyrazole-5-carboxamide compound of the present invention at all.

[0009] International Publication No. 2020 / 109391 International Publication No. 2021 / 224220 International Publication No. 2021 / 228734 International Publication No. 2021 / 233861 International Publication No. 2022 / 207479 International Publication No. 2023 / 243678

[0010] 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 is limited due to the emergence of pathogenic fungi resistant to the agents and the resulting plant diseases. Furthermore, they do not necessarily have satisfactory performance in terms of causing phytotoxicity or contamination to plants, or toxicity to humans, livestock, and fish, and impact on the environment. 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.

[0011] As a result of extensive research, the present inventors have found that a drug containing an N-oxy-pyrazole-5-carboxamide 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.

[0012] That is, the gist of the present invention is as follows: (1) General formula [I] [wherein T represents an oxygen atom or a sulfur atom; R １ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group or C ３ ~C ８ Each of the groups represents a halocycloalkyl group, and each of the groups may have one or more R ５ and R ２ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkoxy-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonylamino-C １ ~C ６ alkyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylcarbonylamino-C ３ ~C ８ Cycloalkyl group (the amino group is R ６ (C １ ~C ６ Alkylcarbonylamino-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylsulfanyl-C １ ~C ６Alkyl group, C １ ~C ６ Alkylsulfanyl-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkylsulfanyl-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkylsulfinyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkylsulfinyl-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkylsulfonyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkylsulfonyl-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C ６ ~C １２ an aryl group, a 9- to 12-membered carbocyclyl group, or a 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R ５ and R ３ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, cyano C １ ~C ６ Alkyl group, or C ６ ~C １２ Aryl-C １ ~C ６ Each of the above groups may have one or more R ５ A is optionally substituted by a substituent selected from C ６ ~C １２ an aryl group, a 9- to 12-membered carbocyclyl group, a 3- to 6-membered heterocyclyl group, or a 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R ５ and R ４ and R ４’ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, or C １ ~C ６ represents a haloalkyl group, or R ４ and R ４’ may be taken together to form an oxo group (=O), or R ４ and R ４’ may each together with the carbon atom to which they are attached form a 3- to 8-membered monocyclic carbocyclyl group, which carbocyclyl group is １ ~C ６ Q may be substituted with one or more substituents selected from alkyl groups, ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C６ Alkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, C ６ ~C １２ an aryl group, a 9- to 12-membered carbocyclyl group, a 3- to 6-membered heterocyclyl group, or a 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R ５ and R ４ and Q may each together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclyl group or a 5- to 12-membered heterocyclyl group having one heteroatom selected from an oxygen atom, a nitrogen atom and a sulfur atom, and the carbocyclyl group may further include a halogen atom, and C １ ~C ６ The heterocyclyl group may be substituted with one or more substituents selected from alkyl groups, and when substituted with two or more substituents, the substituents may be the same or different. The heterocyclyl group may be substituted with one or more substituents selected from halogen atoms and C １ ~C ６ It may be substituted with one or more substituents selected from alkyl groups, and when it is substituted with two or more substituents, the substituents may be the same or different. In the case of a heterocyclyl group containing a nitrogen atom, when the nitrogen atom can be substituted, R ６ and R ５ represents a hydroxy group, a halogen atom, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C ６Alkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Haloalkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, hydroxy C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ８ Cycloalkoxy group, 3- to 6-membered heterocyclyl group, 3- to 6-membered heterocyclyloxy group, 3- to 6-membered heterocyclyl-C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl group, C ６ ~C １２ Aryloxy group, C ６ ~C １２ Aryl-C １ ~C ６Alkoxy group, C ６ ~C １２ Aryl-C ２ ~C ６ Alkynyl group, 9- to 12-membered carbocyclyl group, 5- to 12-membered heteroaryl group, 5- to 12-membered heteroaryloxy group, 5- to 12-membered heteroaryl-C １ ~C ６ Alkoxy group, 5- to 12-membered heteroaryl-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxy group, C ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxycarbonyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfanyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfinyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfonyl-C １ ~C ６ Alkoxy group, C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkoxy group, hydroxy C １ ~C ６ Alkoxy group, cyano C １ ~C ６ Alkoxy group, cyano C ３ ~C８ Cycloalkyl-C １ ~C ６ Alkoxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylcarbonyloxy group, C ３ ~C ８ cycloalkylcarbonyloxy group, C １ ~C ６ Alkyl-C ３ ~C ８ cycloalkylcarbonyloxy group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C ３ ~C ８ cycloalkylcarbonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylcarbonyl group, formyl group, carboxyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Haloalkoxycarbonyl group, C ３ ~C ８ cycloalkoxycarbonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ alkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C３ ~C ８ A cycloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylaminocarbonyl-C １ ~C ６ Alkoxy group (the amino group is R ６ a mercapto group, C １ ~C ６ Alkylsulfanyl group, C １ ~C ６ Haloalkylsulfanyl group, C ３ ~C ８ Cycloalkylsulfanyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfanyl group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Haloalkylsulfinyl group, C ３ ~C ８ Cycloalkylsulfinyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkylsulfonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfonyl group, amino group, C １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from３ ~C ８ A cycloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ６ ~C １２ Arylcarbonylamino group (the amino group is R ６ a 3- to 6-membered heterocyclylcarbonylamino group (the amino group may be substituted with a substituent selected from R ６ a 5- to 12-membered heteroarylcarbonylamino group (the amino group may be substituted with a substituent selected from R ６ may be substituted with a substituent selected from ６ ~C １２ An arylaminocarbonyl group (the amino group is R ６ a 3- to 6-membered heterocyclylaminocarbonyl group (the amino group may be substituted with a substituent selected from R ６ a 5- to 12-membered heteroarylaminocarbonyl group (the amino group may be substituted with a substituent selected from R ６may be substituted with a substituent selected from １ ~C ６ Alkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C １ ~C ６ haloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C ３ ~C ８ A cycloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), -C(=NR７ ) R ８ group, or —OCH ２ C (=NR ７ ) R ８ Each of the groups may be the same or different and may have one or more R ９ and R ６ is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkoxy-C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ７ is a hydroxy group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ８ Cycloalkoxy group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６alkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ and R ８ is a hydrogen atom, C １ ~C ６ Alkyl group, or C ３ ~C ８ represents a cycloalkyl group, R ９ represents a hydroxy group, a halogen atom, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ haloalkoxy group, or C ３ ~C ８ (2) A compound represented by the general formula [I] or a salt thereof, wherein the compound represented by the general formula [IA] (In the formula, A, R ２ and Q have the same meaning as in (1) above. (3) The compound or salt thereof according to (1), wherein the compound represented by general formula [I] is a compound represented by general formula [IB] (In the formula, A, R ２ and R ５ (4) The compound or salt thereof according to (1), wherein the compound represented by general formula [I] is a compound represented by general formula [IC] (In the formula, A, R ５ and n have the same meaning as in (3) above, R２’ is hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkoxy-C １ ~C ６ alkyl)-C ３ ~C ８ Each of the groups may be substituted with one or more R ５ (1) The compound or salt thereof according to (1), which is a compound represented by the formula (I), which may be substituted with a substituent selected from the following: (5) An agricultural and horticultural plant disease control agent comprising the compound or salt thereof according to (1), (2), (3), or (4) as an active ingredient; (6) The agricultural and horticultural plant disease control agent according to (5), wherein the plant disease is caused by a pathogenic fungus; (7) The agricultural and horticultural plant disease control agent according to (6), wherein the pathogenic fungus is classified into the kingdom Fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopira (Oomycetes, etc.), kingdom Rhizaria (Cercozoa, etc.), or bacteria; (8) An agricultural and horticultural plant disease control composition comprising the compound or salt thereof according to (1), (2), (3), or (4), and an agriculturally acceptable carrier. (9) A method for controlling a disease of a useful plant, comprising spraying an effective amount of the compound or salt thereof according to (1), (2), (3), or (4) onto a useful plant or a part of a useful plant, or onto a place where the useful plant is growing. (10) The method according to (9), wherein the plant disease is caused by a pathogenic fungus. (11) The method according to (10), wherein the pathogenic fungus is classified into the kingdom Fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopila (Oomycetes, etc.), kingdom Rhizaria (Cercozoa, etc.) or bacteria. (12) Use of the compound or salt thereof according to (1), (2), (3), or (4) as an agricultural and horticultural plant disease control agent for useful plants.

[0013] The compound of the present invention is useful as an active ingredient of agricultural chemicals such as agricultural and horticultural plant disease control agents, etc. 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 Fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopila (Oomycetes, etc.), Rhizaria (Cercozoa, etc.), bacteria, etc., and can also control fungi that have acquired drug resistance.

[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, "C １ ~C ６ " indicates that the following substituent has 1 to 6 carbon atoms in this case.

[0017] In the present invention, "C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, isopropyl, tert-butyl, n-propyl, sec-butyl, isobutyl, n-butane, 2-methylbutane-1-yl, 2-ethylbutane-2-yl, 3-methylbutane-2-yl, n-pentane, 2-methylpentane-2-yl, pentan-3-yl, isopentyl, neopentyl, sec-pentyl, tert-pentyl, and n-hexyl.

[0018] In the present invention, "C １ ~C ６Unless otherwise specified, the term "alkanediyl group" refers to a straight-chain or branched-chain alkanediyl group having 1 to 6 carbon atoms, and examples thereof include methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, propane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,3-diyl, 2,2-dimethylpropane-1,3-diyl, 2-ethyl-2-methylpropane-1,3-diyl, butane-1,1-diyl, butane-1,2-diyl, and butane-2 ,2-diyl, butane-1,3-diyl, butane-1,4-diyl, 2-methylbutane-1,2-diyl, 2-ethylbutane-1,2-diyl, 3-methylbutane-1,2-diyl, 3-methylbutane-2,2-diyl, 2-methylbutane-1,3-diyl, 2,2-dimethylbutane-1,3-diyl, 3-methylbutane-1,3-diyl, 2,3-dimethylbutane-1,3-diyl, 2-ethylbutane-1,3-diyl, 2-methylbutane-1,4-diyl, 2,2-dimethylbutane-1,4-diyl, 2,3-dimethylbutane-1,4-diyl, 2- Ethylbutane-1,4-diyl, pentane-1,1-diyl, pentane-1,2-diyl, pentane-2,2-diyl, pentane-1,3-diyl, pentane-2,3-diyl, pentane-3,3-diyl, pentane-1,4-diyl, pentane-2,4-diyl, pentane-1,5-diyl, 2-methylpentane-1,2-diyl, 3-methylpentane-1,2-diyl, 4-methylpentane-1,2-diyl, 3-methylpentane-2,2-diyl, 2-methylpentane-1,3-diyl, 3-methylpentane-1,3-diyl, 4-methylpentane hexane-1,3-diyl, 2-methylpentane-2,3-diyl, 3-methylpentane-2,3-diyl, 4-methylpentane-2,3-diyl, 2-methylpentane-3,3-diyl, 2-methylpentane-1,4-diyl, 3-methylpentane-1,4-diyl, 2-methylpentane-2,4-diyl, 3-methylpentane-2,4-diyl, 2-methylpentane-1,5-diyl, 3-methylpentane-1,5-diyl, hexane-1,1-diyl, hexane-1,2-diyl, hexane-2,2-diyl, hexane-1,3-diyl, hexane-2,Examples of groups include hexane-3,3-diyl, hexane-1,4-diyl, hexane-2,4-diyl, hexane-3,4-diyl, hexane-1,5-diyl, hexane-2,5-diyl, and hexane-1,6-diyl.

[0019] In the present invention, "C １ ~C ６ Unless otherwise specified, the term "haloalkyl group" refers to a straight-chain or branched-chain haloalkyl 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, iodomethyl, chlorodifluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2-chloroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-bromoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2-methyl-3-fluoropropan-2-yl, 2-methyl-3,3-difluoropropan-2-yl, 2-methyl-3,3,3-trifluoropropan-2-yl, 2-methyl-4-fluorobutan-2-yl, 2-methyl-4,4-difluorobutan-2-yl, or 2-methyl-4,4,4-trifluorobutan-2-yl groups can be mentioned.

[0020] In the present invention, "C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a cycloalkyl group having 3 to 8 carbon atoms, and the ring may be optionally substituted with an alkyl group within the specified range of carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

[0021] In the present invention, "C ３ ~C ８Unless otherwise specified, the term "cycloalkanediyl group" refers to a cycloalkanediyl group having 3 to 8 carbon atoms, and the ring may be optionally substituted with an alkyl group within the specified range of carbon atoms. For example, cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclobutane-1,2-diyl, cyclopentane-1,1-diyl, cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, cyclohexane-1,1-diyl, cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, cyclohexane-1,4-diyl, cycloheptane-1,1-diyl, cycloheptane-1,2-diyl, cycloheptane-1,3-diyl, cycloheptane-1,4-diyl, cyclooctane-1,1-diyl, cyclooctane-1,2-diyl, cyclooctane-1,3-diyl, cyclooctane-1,4-diyl, cyclooctane-1,5-diyl, and the like groups can be mentioned.

[0022] In the present invention, "C ３ ~C ８ Unless otherwise specified, the term "halocycloalkyl group" refers to a cycloalkyl group having 3 to 8 carbon atoms substituted with 1 to 11 identical or different halogen atoms, and the ring may be optionally substituted with an alkyl group or a haloalkyl group within the range of the specified number of carbon atoms. Examples of the halocycloalkyl group include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 1-fluorocyclobutyl, 2,2-difluorocyclobutyl, 3,3-difluorocyclobutyl, 1-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl, 1-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl, and 4,4-difluorocyclohexyl.

[0023] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-group, and examples thereof include 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 1-ethylcyclopropyl, 2-ethylcyclopropyl, 1-n-propylcyclopropyl, 1-isopropylcyclopropyl, 1-tert-butylcyclopropyl, 1,2,2-trimethylcyclopropyl, 1-methylcyclobutyl, 1-ethylcyclobutyl, 1-isopropylcyclobutyl, 2-methylcyclobutyl, 1-methylcyclopentyl, 1-ethylcyclopentyl, 1-methylcyclohexyl, 1-ethylcyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl groups.

[0024] In the present invention, "C １ ~C ６ Haloalkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the haloalkyl and cycloalkyl moieties have the same meanings as above, and the cycloalkyl moiety is substituted with a haloalkyl group (C １ ~C ６ haloalkyl)-(C ３ ~C ８ cycloalkyl)-group, and examples thereof include 1-difluoromethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-(2,2,2-trifluoroethyl)cyclopropyl, 2-trifluoromethylcyclopropyl, 1-difluoromethylcyclobutyl, 1-trifluoromethylcyclobutyl, 1-difluoromethylcyclopentyl, 1-trifluoromethylcyclopentyl, 1-difluoromethylcyclohexyl, 1-trifluoromethylcyclohexyl, 4-(difluoromethyl)cyclohexyl, and 4-(trifluoromethyl)cyclohexyl groups.

[0025] In the present invention, "C １ ~C６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "halocycloalkyl group" refers to a group in which the alkyl portion and the halocycloalkyl portion have the same meaning as defined above, and the halocycloalkyl portion is substituted with an alkyl group (C １ ~C ６ alkyl)-(C ３ ~C ８ halocycloalkyl)-group, and examples thereof include 2-fluoro-1-methylcyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, 2,2-difluoro-1-methylcyclobutyl, 3,3-difluoro-1-methylcyclobutyl, 2,2-difluoro-1-methylcyclopentyl, 3,3-difluoro-1-methylcyclopentyl, 2,2-difluoro-1-methylcyclohexyl, 3,3-difluoro-1-methylcyclohexyl, and 4,4-difluoro-1-methylcyclohexyl groups.

[0026] In the present invention, "C ２ ~C ６Unless otherwise specified, the term "alkenyl group" refers to a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms, and examples thereof include vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-penten-3-yl, 2-pentenyl, and the like. thenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 1-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-2-butenyl, 2-methyl-3-butenyl, 2-methyl-3-buten-2-yl, 3-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 3-methyl-3-buten-2-yl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2 -hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 1-methyl-4-pentenyl, 2-methyl-1-penten-3-yl, 2-methyl-2-pentenyl, 2-methyl-4-penten-2-yl, 3-methyl-1-buten-2-yl, 3-methyl-3-pentenyl, 3-methyl-4-pentenyl, 3-methyl-1-penten-3-yl, 3-methyl-4-penten-2-yl, 4 4-methyl-1-penten-3-yl, 4-methyl-3-pentenyl, 4-methyl-3-penten-2-yl, 4-methyl-4-pentenyl, 4-methyl-4-penten-2-yl, 1-hexen-3-yl, 4-hexen-3-yl, 5-hexen-3-yl, 2,3-dimethyl-3-buten-2-yl, 1,5-hexadienyl, 1,5-hexadien-3-yl, or 2,4-hexadienyl groups can be mentioned.

[0027] In the present invention, "C ２ ~C ６Unless otherwise specified, the term "haloalkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 11 identical or different halogen atoms, and examples thereof include 2-chlorovinyl, 2,2-dichlorovinyl, 2-chloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-methyl-2-propenyl, 3-chloro-2-butenyl, 2-fluorovinyl, 2,2-difluorovinyl, 2-fluoro-2-propenyl, 3,3-difluoro-2-propenyl, 2, Examples of groups include 3-difluoro-2-propenyl, 3,3-difluoro-2-methyl-2-propenyl, 3-fluoro-2-butenyl, 2-bromovinyl, 2,2-dibromovinyl, 2-bromo-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 3,3-dibromo-2-methyl-2-propenyl, 3-bromo-2-butenyl, 2-iodovinyl, 2,2-diiodovinyl, 2-iodo-2-propenyl, 3,3-diiodo-2-propenyl, and 2,3-diiodo-2-propenyl.

[0028] In the present invention, "C ２ ~C ６ Unless otherwise specified, the term "alkynyl group" refers to a straight-chain or branched-chain 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, 3-methyl-1-butynyl, 4-pentynyl, 4-methyl-1-pentynyl, and 4,4-dimethyl-2-pentynyl.

[0029] In the present invention, "hydroxy C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (hydroxy)-(C １ ~C ６alkyl)-group, 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 groups.

[0030] In the present invention, "hydroxy C ２ ~C ６ Unless otherwise specified, the term "alkynyl group" refers to a group in which the alkynyl moiety has the above meaning and a hydroxy group is substituted on the alkynyl moiety (hydroxy)-(C ２ ~C ６ alkynyl) group, and examples thereof include 3-hydroxy-1-propynyl, 3-hydroxy-1-butynyl, 3-hydroxy-3-methyl-1-butynyl, 4-hydroxy-1-butynyl, 4-hydroxy-1-pentynyl, and 4-hydroxy-4-methyl-1-pentynyl groups.

[0031] In the present invention, "cyano C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (cyano)-(C １ ~C ６ alkyl)-group, and examples thereof include cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 2-cyano-2-propyl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl, and 6-cyanohexyl groups.

[0032] In the present invention, "C ３ ~C ８ Cycloalkyl-C １ ~C ６ Unless otherwise specified, the cycloalkyl and alkyl moieties of the "alkyl group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C １ ~C ６alkyl)-group, and examples thereof include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 2-cyclopropylpropan-2-yl, 2-cyclobutylpropan-2-yl, 2-cyclopentylpropan-2-yl, and 1-cyclopropylpropyl groups.

[0033] In the present invention, "C ３ ~C ８ Cycloalkyl-C ２ ~C ６ Unless otherwise specified, the cycloalkyl and alkynyl moieties of the "alkynyl group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C ２ ~C ６ alkynyl) group, and examples thereof include cyclopropylethynyl, cyclobutylethynyl, cyclopentaneethynyl, cyclohexaneethynyl, cycloheptaneethynyl, and cyclooctaneethynyl groups.

[0034] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonyl group" has the above meaning (C １ ~C ６ alkyl)-C(═O)— group, and examples thereof include methylcarbonyl, ethylcarbonyl, isopropylcarbonyl, tert-butylcarbonyl, n-propylcarbonyl, sec-butylcarbonyl, isobutylcarbonyl, n-butylcarbonyl, 2-methylbutan-1-ylcarbonyl, 3-methylbutan-2-ylcarbonyl, n-pentylcarbonyl, 2-methylpentan-2-ylcarbonyl, pentan-3-ylcarbonyl, isopentylcarbonyl, neopentylcarbonyl, sec-pentylcarbonyl, tert-pentylcarbonyl, and n-hexylcarbonyl.

[0035] In the present invention, "C １ ~C ６Unless otherwise specified, the haloalkyl moiety of the "haloalkylcarbonyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-C(═O)— group, and examples thereof include fluoromethylcarbonyl, difluoromethylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, trichloromethylcarbonyl, tribromomethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, and 3,3,3-trifluoropropylcarbonyl groups.

[0036] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylcarbonyl group" has the above meaning (C ３ ~C ６ cycloalkyl)-C(=O)- group, and examples thereof include cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl, cycloheptanecarbonyl, and cyclooctanecarbonyl groups.

[0037] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylcarbonyl group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-C(═O)— group, and examples thereof include 1-methylcyclopropanecarbonyl, 1-methylcyclobutanecarbonyl, 1-methylcyclopentanecarbonyl, and 1-methylcyclohexanecarbonyl groups.

[0038] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonyloxy group" has the above meaning (C １ ~C６ alkyl)-C(═O)—O— group, and examples thereof include methylcarbonyloxy, ethylcarbonyloxy, isopropylcarbonyloxy, tert-butylcarbonyloxy, n-propylcarbonyloxy, sec-butylcarbonyloxy, isobutylcarbonyloxy, n-butanecarbonyloxy, 2-methylbutan-1-ylcarbonyloxy, 3-methylbutan-2-ylcarbonyloxy, n-pentanecarbonyloxy, 2-methylpentan-2-ylcarbonyloxy, pentan-3-ylcarbonyloxy, isopentylcarbonyloxy, neopentylcarbonyloxy, sec-pentylcarbonyloxy, tert-pentylcarbonyloxy, and n-hexylcarbonyloxy.

[0039] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylcarbonyloxy group" has the above meaning (C ３ ~C ８ cycloalkyl)-C(═O)—O— group, and examples thereof include cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cycloheptylcarbonyloxy, and cyclooctylcarbonyloxy groups.

[0040] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylcarbonyloxy group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-C(═O)—O— group, and examples thereof include 1-methylcyclopropylcarbonyloxy, 1-methylcyclobutylcarbonyloxy, 1-methylcyclopentylcarbonyloxy, and 1-methylcyclohexylcarbonyloxy groups.

[0041] In the present invention, "C １ ~C ６ Alkylcarbonylamino-C １ ~C ６ Unless otherwise specified, the alkyl group "has the above-mentioned meanings for the alkylcarbonylamino moiety and alkyl moiety (C １ ~C ６ alkyl)-C(=O)-NH-(C １ ~C ６ alkyl)-group, and examples thereof include 2-(methylcarbonylamino)-2-methylethan-2-yl, 2-(ethylcarbonylamino)-2-methylethan-2-yl, 2-(n-propylcarbonylamino)-2-methylethan-2-yl, 2-(isopropylcarbonylamino)-2-methylethan-2-yl, 3-(methylcarbonylamino)-2-methylpropan-2-yl, 3-(ethylcarbonylamino)-2-methylpropan-2-yl, 3-(n-propylcarbonylamino)-2-methylpropan-2-yl, and 3-(isopropylcarbonylamino)-2-methylpropan-2-yl groups.

[0042] In the present invention, "C １ ~C ６ Alkylcarbonylamino-C ３ ~C ８ Unless otherwise specified, the "cycloalkyl group" refers to a group in which the alkylcarbonylamino moiety and the cycloalkyl moiety have the same meaning as above (C １ ~C ６ alkyl)-C(=O)-NH-(C ３ ~C ８cycloalkyl)- group, for example, 1-(methylcarbonylamino)cyclopropan-1-yl, 1-(ethylcarbonylamino)cyclopropan-1-yl, 1-(n-propylcarbonylamino)cyclopropan-1-yl, 1-(isopropylcarbonylamino)cyclopropan-1-yl, 1-(methylcarbonylamino)cyclobutan-1-yl, 1-(ethylcarbonylamino)cyclobutan-1-yl, 1-(n-propylcarbonylamino)cyclobutan-1-yl, 1-(isopropylcarbonylamino)cyclobutan-1-yl, Examples of such groups include 1-(methylcarbonylamino)cyclopentan-1-yl, 1-(ethylcarbonylamino)cyclopentan-1-yl, 1-(n-propylcarbonylamino)cyclopentan-1-yl, 1-(isopropylcarbonylamino)cyclopentan-1-yl, 1-(methylcarbonylamino)cyclohexan-1-yl, 1-(ethylcarbonylamino)cyclohexan-1-yl, 1-(n-propylcarbonylamino)cyclohexan-1-yl, and 1-(isopropylcarbonylamino)cyclohexan-1-yl.

[0043] In the present invention, "(C １ ~C ６ Alkylcarbonylamino-C １ ~C ６ alkyl)-C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the alkylcarbonylamino moiety, alkyl group moiety, and cycloalkyl group moiety have the same meaning as defined above (C １ ~C ６ alkyl)-C(=O)-NH-(C １ ~C ６ alkyl)-(C ３ ~C ８cycloalkyl)- group, for example, 1-(methylcarbonylaminomethyl)cyclopropan-1-yl, 1-(ethylcarbonylaminomethyl)cyclopropan-1-yl, 1-(n-propylcarbonylaminomethyl)cyclopropan-1-yl, 1-(isopropylcarbonylaminomethyl)cyclopropan-1-yl, 1-(methylcarbonylaminomethyl)cyclobutan-1-yl, 1-(ethylcarbonylaminomethyl)cyclobutan-1-yl, 1-(n-propylcarbonylaminomethyl)cyclobutan-1-yl, 1-(isopropylcarbonylaminomethyl)cyclobutan-1-yl, Examples of groups that can be mentioned include 1-(methylcarbonylaminomethyl)cyclopentan-1-yl, 1-(ethylcarbonylaminomethyl)cyclopentan-1-yl, 1-(n-propylcarbonylaminomethyl)cyclopentan-1-yl, 1-(isopropylcarbonylaminomethyl)cyclopentan-1-yl, 1-(methylcarbonylaminomethyl)cyclohexan-1-yl, 1-(ethylcarbonylaminomethyl)cyclohexan-1-yl, 1-(n-propylcarbonylaminomethyl)cyclohexan-1-yl, and 1-(isopropylcarbonylaminomethyl)cyclohexan-1-yl.

[0044] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfanyl group" has the above meaning (C １ ~C ６ alkyl)-S- group, and examples thereof include methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, isobutylsulfanyl, sec-butylsulfanyl, and tert-butylsulfanyl groups.

[0045] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylsulfanyl group" has the same meaning as above (C １ ~C ６haloalkyl)-S- group, and examples thereof include fluoromethylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, trichloromethylsulfanyl, 2,2,2-trifluoroethylsulfanyl, pentafluoroethylsulfanyl, 2,2,2-trichloroethylsulfanyl, 3,3,3-trifluoropropylsulfanyl, heptafluoropropylsulfanyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfanyl, heptafluoro-2-propylsulfanyl, and 4,4,4-trifluorobutylsulfanyl groups.

[0046] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfanyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-S- group, and examples thereof include cyclopropylsulfanyl, cyclobutylsulfanyl, cyclopentylsulfanyl, cyclohexylsulfanyl, cycloheptylsulfanyl, and cyclooctylsulfanyl groups.

[0047] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylsulfanyl group" refers to a group in which the alkyl and cycloalkyl moieties have the same meanings as above, and an alkyl group is substituted on the cycloalkyl moiety (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-S- group, and examples thereof include 1-methylcyclopropylsulfanyl, 1-methylcyclobutylsulfanyl, 1-methylcyclopentylsulfanyl, and 1-methylcyclohexylsulfanyl groups.

[0048] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfinyl group" has the above meaning (C １ ~C６ alkyl)-S(=O)- group, and examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl groups.

[0049] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylsulfinyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-S(═O)— group, and examples thereof include fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfinyl, heptafluoro-2-propylsulfinyl, and 4,4,4-trifluorobutylsulfinyl groups.

[0050] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfinyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-S(=O)- group, and examples thereof include cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl, and cyclooctylsulfinyl groups.

[0051] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylsulfinyl group" refers to a group in which the alkyl and cycloalkyl moieties have the same meanings as above, and an alkyl group is substituted on the cycloalkyl moiety (C１ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-S(═O)— group, and examples thereof include 1-methylcyclopropylsulfinyl, 1-methylcyclobutylsulfinyl, 1-methylcyclopentylsulfinyl, and 1-methylcyclohexylsulfinyl groups.

[0052] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfonyl group" has the above meaning (C １ ~C ６ alkyl)-S(=O) ２ - group, and examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, and tert-butylsulfonyl groups.

[0053] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylsulfonyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-S(=O) ２ - group, and examples thereof include fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfonyl, heptafluoro-2-propylsulfonyl, and 4,4,4-trifluorobutylsulfonyl groups.

[0054] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfonyl group" has the above meaning (C ３ ~C８ cycloalkyl)-S(=O) ２ - group, and examples thereof include cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl, and cyclooctylsulfonyl groups.

[0055] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylsulfonyl group" refers to a group in which the alkyl and cycloalkyl moieties have the same meanings as above, and an alkyl group is substituted on the cycloalkyl moiety (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-S(=O) ２ - group, and examples thereof include 1-methylcyclopropylsulfonyl, 1-methylcyclobutylsulfonyl, 1-methylcyclopentylsulfonyl, and 1-methylcyclohexylsulfonyl groups.

[0056] In the present invention, "C １ ~C ６ Alkylsulfanyl-C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-S-(C １ ~C ６ alkyl)-group, and examples thereof include 1-methylsulfanyl-1-methylethyl, 1-ethylsulfanyl-1-methylethyl, 1-n-propylsulfanyl-1-methylethyl, 1-isopropylsulfanyl-1-methylethyl, 3-methylsulfanyl-2-methylpropan-2-yl, 3-ethylsulfanyl-2-methylpropan-2-yl, 3-n-propylsulfanyl-2-methylpropan-2-yl, and 3-isopropylsulfanyl-2-methylpropan-2-yl groups.

[0057] In the present invention, "C １ ~C６ Alkylsulfanyl-C ３ ~C ８ Unless otherwise specified, the alkyl and cycloalkyl groups have the same meanings as above (C １ ~C ６ alkyl)-S-(C ３ ~C ８ cycloalkyl)-group, and examples thereof include 1-methylsulfanylcyclopropyl, 1-ethylsulfanylcyclopropyl, 1-n-propylsulfanylcyclopropyl, 1-isopropylsulfanylcyclopropyl, 1-methylsulfanylcyclobutyl, 1-ethylsulfanylcyclobutyl, 1-n-propylsulfanylcyclobutyl, 1-isopropylsulfanylcyclobutyl, 1-methylsulfanylcyclopentyl, 1-ethylsulfanylcyclopentyl, 1-n-propylsulfanylcyclopentyl, and 1-isopropylsulfanylcyclopentyl groups.

[0058] In the present invention, "(C １ ~C ６ Alkylsulfanyl-C １ ~C ６ alkyl)-C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the alkyl moiety, alkylsulfanyl moiety, and cycloalkyl moiety have the same meaning as above, and the cycloalkyl moiety is substituted with an alkyl group having an alkylsulfanyl group (C １ ~C ６ alkyl)-S-(C １ ~C ６ alkyl)-(C ３ ~C ８cycloalkyl)- group, and examples thereof include 1-(methylsulfanylmethyl)cyclopropyl, 1-(ethylsulfanylmethyl)cyclopropyl, 1-(n-propylsulfanylmethyl)cyclopropyl, 1-(isopropylsulfanylmethyl)cyclopropyl, 1-(methylsulfanylmethyl)cyclobutyl, 1-(ethylsulfanylmethyl)cyclobutyl, 1-(n-propylsulfanylmethyl)cyclobutyl, 1-(isopropylsulfanylmethyl)cyclobutyl, 1-(methylsulfanylmethyl)cyclopentyl, 1-(ethylsulfanylmethyl)cyclopentyl, 1-(n-propylsulfanylmethyl)cyclopentyl, and 1-(isopropylsulfanylmethyl)cyclopentyl groups.

[0059] In the present invention, "C １ ~C ６ Alkylsulfinyl-C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-S(=O)-(C １ ~C ６ alkyl)-group, 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 groups.

[0060] In the present invention, "C １ ~C ６ Alkylsulfinyl-C ３ ~C ８ Unless otherwise specified, the alkyl and cycloalkyl groups have the same meanings as above (C １ ~C ６ alkyl)-S(=O)-(C ３ ~C８ cycloalkyl)-group, and examples thereof include 1-methylsulfinylcyclopropyl, 1-ethylsulfinylcyclopropyl, 1-n-propylsulfinylcyclopropyl, 1-isopropylsulfinylcyclopropyl, 1-methylsulfinylcyclobutyl, 1-ethylsulfinylcyclobutyl, 1-n-propylsulfinylcyclobutyl, 1-isopropylsulfinylcyclobutyl, 1-methylsulfinylcyclopentyl, 1-ethylsulfinylcyclopentyl, 1-n-propylsulfinylcyclopentyl, and 1-isopropylsulfinylcyclopentyl groups.

[0061] In the present invention, "(C １ ~C ６ Alkylsulfinyl-C １ ~C ６ alkyl)-C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the alkyl moiety, alkylsulfinyl moiety, and cycloalkyl moiety have the same meaning as above, and the cycloalkyl moiety is substituted with an alkyl group having an alkylsulfinyl group (C １ ~C ６ alkyl)-S(=O)-(C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)- group, and examples thereof include 1-(methylsulfinylmethyl)cyclopropyl, 1-(ethylsulfinylmethyl)cyclopropyl, 1-(n-propylsulfinylmethyl)cyclopropyl, 1-(isopropylsulfinylmethyl)cyclopropyl, 1-(methylsulfinylmethyl)cyclobutyl, 1-(ethylsulfinylmethyl)cyclobutyl, 1-(n-propylsulfinylmethyl)cyclobutyl, 1-(isopropylsulfinylmethyl)cyclobutyl, 1-(methylsulfinylmethyl)cyclopentyl, 1-(ethylsulfinylmethyl)cyclopentyl, 1-(n-propylsulfinylmethyl)cyclopentyl, and 1-(isopropylsulfinylmethyl)cyclopentyl groups.

[0062] In the present invention, "C １ ~C ６ Alkylsulfonyl-C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-S(=O) ２ -(C １ ~C ６ alkyl)-group, 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 groups.

[0063] In the present invention, "C １ ~C ６ Alkylsulfonyl-C ３ ~C ８ Unless otherwise specified, the alkyl and cycloalkyl groups have the same meanings as above (C １ ~C ６ alkyl)-S(=O) ２ -(C ３ ~C ８ cycloalkyl)-group, and examples thereof include 1-methylsulfonylcyclopropyl, 1-ethylsulfonylcyclopropyl, 1-n-propylsulfonylcyclopropyl, 1-isopropylsulfonylcyclopropyl, 1-methylsulfonylcyclobutyl, 1-ethylsulfonylcyclobutyl, 1-n-propylsulfonylcyclobutyl, 1-isopropylsulfonylcyclobutyl, 1-methylsulfonylcyclopentyl, 1-ethylsulfonylcyclopentyl, 1-n-propylsulfonylcyclopentyl, and 1-isopropylsulfonylcyclopentyl groups.

[0064] In the present invention, "(C １ ~C ６Alkylsulfonyl-C １ ~C ６ alkyl)-C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the alkyl moiety, alkylsulfonyl moiety, and cycloalkyl moiety have the same meaning as above, and the cycloalkyl moiety is substituted with an alkyl group having an alkylsulfonyl group (C １ ~C ６ alkyl)-S(=O) ２ -(C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)- group, and examples thereof include 1-(methylsulfonylmethyl)cyclopropyl, 1-(ethylsulfonylmethyl)cyclopropyl, 1-(n-propylsulfonylmethyl)cyclopropyl, 1-(isopropylsulfonylmethyl)cyclopropyl, 1-(methylsulfonylmethyl)cyclobutyl, 1-(ethylsulfonylmethyl)cyclobutyl, 1-(n-propylsulfonylmethyl)cyclobutyl, 1-(isopropylsulfonylmethyl)cyclobutyl, 1-(methylsulfonylmethyl)cyclopentyl, 1-(ethylsulfonylmethyl)cyclopentyl, 1-(n-propylsulfonylmethyl)cyclopentyl, and 1-(isopropylsulfonylmethyl)cyclopentyl groups.

[0065] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl portion of the "alkoxy group" has the above meaning (C １ ~C ６ alkyl)-O- group, and examples thereof include methoxy, ethoxy, isopropoxy, tert-butoxy, n-propoxy, sec-butoxy, isobutoxy, n-butoxy, 2-methylbutan-1-yloxy, 2-ethylbutan-2-yloxy, 3-methylbutan-2-yloxy, n-pentyloxy, 2-methylpentan-2-yloxy, pentan-3-yloxy, isopentyloxy, neopentyloxy, sec-pentyloxy, tert-pentyloxy, and n-hexyloxy.

[0066] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkoxy group has the same meaning as defined above (C １ ~C ６ haloalkyl)-O- group, and examples thereof include difluoromethoxy, dichloromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, and 1,1,2,3,3,3-hexafluoropropoxy groups.

[0067] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkoxy group has the above-mentioned meaning in the cycloalkyl portion (C ３ ~C ８ cycloalkyl)-O- group, and examples thereof include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy groups.

[0068] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkoxy group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-O- group, and examples thereof include 1-methylcyclopropyloxy, 1-methylcyclobutyloxy, 1-methylcyclopentyloxy, and 1-methylcyclohexyloxy groups.

[0069] In the present invention, "C １ ~C６ Alkoxy-C ２ ~C ６ Unless otherwise specified, the term "alkynyl group" refers to a group in which the alkoxy moiety and the alkynyl moiety have the same meaning as above, and an alkynyl moiety is substituted with an alkoxy group (C １ ~C ６ alkoxy)-(C ２ ~C ６ alkynyl) group, and examples thereof include 3-methoxy-1-propynyl, 3-methoxy-1-butynyl, 3-methoxy-3-methyl-1-butynyl, 4-methoxy-1-butynyl, 4-methoxy-1-pentynyl, and 4-methoxy-4-methyl-1-pentynyl groups.

[0070] In the present invention, "C ２ ~C ６ Unless otherwise specified, the alkenyl moiety of the "alkenyloxy group" has the above meaning (C ２ ~C ６ alkenyl)-O- group, and examples thereof include vinyloxy, 1-propenyloxy, isopropenyloxy, 2-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, and 5-hexenyloxy groups.

[0071] In the present invention, "C ２ ~C ６ Unless otherwise specified, the alkynyl moiety of the "alkynyloxy group" has the above meaning (C ２ ~C ６alkynyl)-O- group, and examples thereof include ethynyloxy, 1-propynyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 1-butynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 1-pentynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, and 4,4-dimethyl-2-pentynyloxy groups.

[0072] In the present invention, "tori (C １ ~C ６ Unless otherwise specified, the alkyl portion of the "silyloxy group" is defined as above (C １ ~C ６ alkyl) ３ It represents an —Si—O— group, and the three alkyl groups may be the same or different. Examples include trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, dimethylisopropylsilyloxy, and tert-butyldimethylsilyloxy groups.

[0073] In the present invention, "C １ ~C ６ Alkoxy-C １ ~C ６ Unless otherwise specified, the alkoxy and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ alkoxy)-(C １ ~C ６alkyl)-group, and examples thereof include methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, 1-isopropoxyethyl, 1-methoxypropyl, 2-methoxypropyl, 1-ethoxypropyl, 1-methoxybutyl, 1-ethoxybutyl, 3-methoxypropan-2-yl, 3-ethoxypropan-2-yl, 3-methoxy-2-methylpropan-2-yl, 3-ethoxy-2-methylpropan-2-yl, 4-methoxybutan-2-yl, 4-ethoxybutan-2-yl, 4-methoxy-2-methylbutan-2-yl, and 4-ethoxy-2-methylbutan-2-yl groups.

[0074] In the present invention, "C １ ~C ６ Alkoxy-C ３ ~C ８ Unless otherwise specified, the alkoxy and cycloalkyl groups have the same meanings as above (C １ ~C ６ alkoxy)-(C ３ ~C ８ cycloalkyl)-group, and examples thereof include 1-methoxycyclopropyl, 1-ethoxycyclopropyl, 1-methoxycyclobutyl, 1-ethoxycyclobutyl, 1-methoxycyclopentyl, 1-ethoxycyclopentyl, 1-methoxycyclohexyl, and 1-ethoxycyclohexyl groups.

[0075] In the present invention, "(C １ ~C ６ Alkoxy-C １ ~C ６ alkyl)-C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a group in which the alkyl moiety, alkoxy moiety, and cycloalkyl moiety have the same meaning as above, and the cycloalkyl moiety is substituted with an alkyl group having an alkoxy group (C １ ~C ６ alkoxy)-(C １ ~C ６alkyl)-(C ３ ~C ８ cycloalkyl)-group, and examples thereof include 1-(methoxymethyl)cyclopropyl, 1-(ethoxymethyl)cyclopropyl, 1-(methoxymethyl)cyclobutyl, 1-(ethoxymethyl)cyclobutyl, 1-(methoxymethyl)cyclopentyl, 1-(ethoxymethyl)cyclopentyl, 1-(methoxymethyl)cyclohexyl, and 1-(ethoxymethyl)cyclohexyl groups.

[0076] In the present invention, "C １ ~C ６ Haloalkoxy-C １ ~C ６ Unless otherwise specified, the haloalkoxy moiety and alkyl moiety have the same meaning as above (C １ ~C ６ haloalkoxy)-(C １ ~C ６ alkyl)-group, and examples thereof include 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethoxy)ethyl, 2-(2,2,2-trifluoroethoxy)ethyl, 2-(3,3-difluoropropioxy)ethyl, 2-(3,3,3-trifluoropropioxy)ethyl, 3-(difluoromethoxy)propyl, 3-(trifluoromethoxy)propyl, 3-(2,2-difluoroethoxy)propyl, 3-(2,2,2-trifluoroethoxy)propyl, 3-(3,3-difluoropropoxy)propyl, 3-(3,3,3-trifluoropropioxy)propyl, 4-(trifluoromethoxy)butyl, and 5-(trifluoromethoxy)pentyl groups.

[0077] In the present invention, "C １ ~C ６ Alkoxy-C １ ~C ６ Unless otherwise specified, the alkoxy group has the above meaning in the alkoxy portion. １ ~C ６ alkoxy)-(C １ ~C ６alkoxy)-groups, and examples thereof include methoxymethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-(n-propoxy)ethoxy, 2-isopropoxyethoxy, 2-(n-butoxy)ethoxy, 2-(sec-butoxy)ethoxy, 2-isobutoxyethoxy, and 2-(tert-butoxy)ethoxy groups.

[0078] In the present invention, "C １ ~C ６ Alkylsulfanyl-C １ ~C ６ Unless otherwise specified, the alkyl and alkoxy groups have the same meanings as above (C １ ~C ６ alkyl)-S-(C １ ~C ６ alkoxy)-groups, and examples thereof include (methylsulfanyl)methoxy, 2-(methylsulfanyl)ethoxy, 2-(ethylsulfanyl)ethoxy, 2-(n-propylsulfanyl)ethoxy, 2-(isopropylsulfanyl)ethoxy, 2-(n-butylsulfanyl)ethoxy, 2-(sec-butylsulfanyl)ethoxy, 2-(isobutylsulfanyl)ethoxy, and 2-(tert-butylsulfanyl)ethoxy groups.

[0079] In the present invention, "C １ ~C ６ Alkylsulfinyl C １ ~C ６ Unless otherwise specified, the alkyl and alkoxy groups have the same meanings as above (C １ ~C ６ alkyl)-S(=O)-(C １ ~C ６alkoxy)-group, and examples thereof include (methylsulfinyl)methoxy, 2-(methylsulfinyl)ethoxy, 2-(ethylsulfinyl)ethoxy, 2-(n-propylsulfinyl)ethoxy, 2-(isopropylsulfinyl)ethoxy, 2-(n-butylsulfinyl)ethoxy, 2-(sec-butylsulfinyl)ethoxy, 2-(isobutylsulfinyl)ethoxy, and 2-(tert-butylsulfinyl)ethoxy groups.

[0080] In the present invention, "C １ ~C ６ Alkylsulfonyl C １ ~C ６ Unless otherwise specified, the alkyl and alkoxy groups have the same meanings as above (C １ ~C ６ alkyl)-S(=O) ２ -(C １ ~C ６ alkoxy)-group, and examples thereof include (methylsulfonyl)methoxy, 2-(methylsulfonyl)ethoxy, 2-(ethylsulfonyl)ethoxy, 2-(n-propylsulfonyl)ethoxy, 2-isopropylsulfonylethoxy, 2-(n-butylsulfonyl)ethoxy, 2-(sec-butylsulfonyl)ethoxy, 2-(isobutylsulfonyl)ethoxy, and 2-(tert-butylsulfonyl)ethoxy groups.

[0081] In the present invention, "C ３ ~C ８ Cycloalkyl-C １ ~C ６ Unless otherwise specified, the cycloalkyl and alkoxy groups have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C １ ~C ６ alkoxy)-group, and examples thereof include cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cycloheptylmethoxy, and cyclooctylmethoxy groups.

[0082] In the present invention, "cyano C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a group in which the alkoxy moiety has the above meaning (cyano)-(C １ ~C ６ alkoxy)-groups, and examples thereof include cyanomethoxy, 1-cyanoethoxy, 2-cyanoethoxy, 1-cyanopropoxy, 2-cyanopropoxy, 2-cyano-2-methylpropoxy, 3-cyanopropoxy, 2-cyano-2-propoxy, 1-cyanobutoxy, 4-cyanobutoxy, 5-cyanopentyloxy, and 6-cyanohexyloxy groups.

[0083] In the present invention, "cyano C ３ ~C ８ Cycloalkyl-C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a (cyano)-(C) group in which the cycloalkyl and alkoxy moieties have the same meanings as above and in which a cycloalkyl group is substituted on the alkoxy moiety. ３ ~C ８ cycloalkyl)-(C １ ~C ６ alkoxy)-group, and examples thereof include 1-cyanocyclopropyl-1-methoxy, 1-cyanocyclopropyl-1-ethoxy, 1-cyanocyclobutyl-1-methoxy, 1-cyanocyclobutyl-1-ethoxy, 1-cyanocyclopentane-1-methoxy, 1-cyanocyclopentane-1-ethoxy, 1-cyanocyclohexane-1-methoxy, and 1-cyanocyclohexane-1-ethoxy groups.

[0084] In the present invention, "hydroxy C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a (hydroxy)-(C １ ~C ６alkoxy)-groups, and examples thereof include 2-hydroxy-1-ethoxy, 3-hydroxy-2-propoxy, 3-hydroxy-2-methyl-2-propoxy, 2-hydroxy-1-propoxy, 2-hydroxy-2-methyl-1-propoxy, and 3-hydroxy-1-propoxy groups.

[0085] In the present invention, the term "formyl group" refers to an H--C(.dbd.O)-- group.

[0086] In the present invention, the term "carboxyl group" refers to an HO-C(=O)- group.

[0087] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkoxy moiety of the "alkoxycarbonyl group" has the above meaning (C １ ~C ６ alkoxy)-C(═O)— group, and examples thereof include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, n-propoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, n-butoxycarbonyl, 2-methylbutan-1-yloxycarbonyl, 2-ethylbutan-2-yloxycarbonyl, 3-methylbutan-2-yloxycarbonyl, n-pentyloxycarbonyl, 2-methylpentan-2-yloxycarbonyl, pentan-3-yloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, sec-pentyloxycarbonyl, tert-pentyloxycarbonyl, and n-hexyloxycarbonyl.

[0088] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkoxycarbonyl group has the same meaning as defined above (C １ ~C ６haloalkyl)-O-C(=O)- group, and examples thereof include difluoromethoxycarbonyl, dichloromethoxycarbonyl, trifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 1,1,2,2-tetrafluoroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-chloro-1,1,2-trifluoroethoxycarbonyl, and 2-chloro-1,1,2,2-tetrafluoroethoxycarbonyl.

[0089] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkoxycarbonyl group has the above-mentioned meaning in the cycloalkyl portion (C ３ ~C ８ cycloalkyl)-O-C(=O)- group, and examples thereof include cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cycloheptyloxycarbonyl, and cyclooctyloxycarbonyl groups.

[0090] In the present invention, "C １ ~C ６ Alkylcarbonyl-C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a group in which the alkyl and alkoxy moieties have the same meanings as above, and an alkylcarbonyl group is substituted on the alkoxy moiety (C １ ~C ６ alkyl)-C(=O)-(C １ ~C ６ alkoxy)-groups, and examples thereof include methylcarbonylmethoxy, ethylcarbonylmethoxy, methylcarbonylethoxy, ethylcarbonyl-1-ethoxy, and ethylcarbonyl-2-ethoxy groups.

[0091] In the present invention, "C １ ~C ６ Alkoxycarbonyl-C １ ~C ６Unless otherwise specified, the alkoxy group has the above meaning in the alkoxy portion. １ ~C ６ alkoxy)-C(═O)-(C １ ~C ６ alkoxy)-groups, and examples thereof include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n-propoxycarbonylmethoxy, 2-(methoxycarbonyl)ethoxy, 2-(ethoxycarbonyl)ethoxy, and 2-(n-propoxycarbonyl)ethoxy groups.

[0092] In the present invention, "C １ ~C ６ Alkylaminocarbonyl-C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a group in which the alkyl and alkoxy moieties have the same meanings as above, and an alkylaminocarbonyl group is substituted on the alkoxy moiety (C １ ~C ６ alkyl)-NH-C(=O)-(C １ ~C ６ alkoxy)-group, and examples thereof include methylaminocarbonylmethoxy, ethylaminocarbonylmethoxy, n-propylaminocarbonylmethoxy, isopropylaminocarbonylmethoxy, and n-butylaminocarbonylmethoxy groups.

[0093] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkoxycarbonyl group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-O-C(=O)- group, and examples thereof include 1-methylcyclopropyloxycarbonyl, 1-methylcyclobutyloxycarbonyl, 1-methylcyclopentyloxycarbonyl, and 1-methylcyclohexyloxycarbonyl groups.

[0094] In the present invention, "C ６ ~C １２ Unless otherwise specified, the term "aryl group" refers to an aryl group having 6 to 12 carbon atoms, and examples thereof include phenyl, naphthalen-1-yl, and naphthalen-2-yl groups.

[0095] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "aryloxy group" has the above meaning (C ６ ~C １２ aryl)-O- group, and examples thereof include phenyloxy, naphthalen-1-yloxy, and naphthalen-1-yloxy groups.

[0096] In the present invention, "C ６ ~C １２ Aryl-C １ ~C ６ Unless otherwise specified, the aryl and alkyl portions of the "alkyl group" have the same meanings as above (C ６ ~C １２ aryl)-(C １ ~C ６ alkyl)-group, and examples thereof include benzyl, 2-phenylethan-1-yl, 2-phenylethan-2-yl, 2-phenylpropan-1-yl, 2-phenylbutan-1-yl, naphthalen-1-ylmethyl, and naphthalen-2-ylmethyl groups.

[0097] In the present invention, "C ６ ~C １２ Aryl-C １ ~C ６ Unless otherwise specified, the aryl and alkoxy groups have the same meanings as above (C ６ ~C １２ aryl)-(C １ ~C ６alkoxy)-groups, and examples thereof include benzyloxy, 2-phenylethan-1-yloxy, 2-phenylethan-2-yloxy, 2-phenylpropan-1-yloxy, 2-phenylbutan-1-yloxy, naphthalen-1-ylmethyloxy, and naphthalen-2-ylmethyloxy groups.

[0098] In the present invention, "C ６ ~C １２ Aryl-C ２ ~C ６ Unless otherwise specified, the aryl and alkynyl groups have the same meanings as above (C ６ ~C １２ aryl)-(C ２ ~C ６ alkynyl)-group, and examples thereof include phenylethynyl and the like.

[0099] In the present invention, unless otherwise specified, the term "9- to 12-membered carbocyclyl group" refers to a 9- to 12-membered non-aromatic carbocycle or aromatic carbocycle having a saturated or unsaturated carbocycle, and examples thereof include indan-4-yl, indan-5-yl, tetralin-5-yl, and tetralin-6-yl.

[0100] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclyl group" refers to a 3- to 6-membered non-aromatic heterocycle containing, in addition to carbon atoms, one or more heteroatoms selected from oxygen atoms, nitrogen atoms, sulfur atoms, and boron atoms, and examples thereof include aziridin-1-yl, aziridin-2-yl, oxiran-2-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, 2,5-dihydrofuran-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, Examples of such groups include tetrahydropyran-3-yl, tetrahydropyran-4-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, piperazin-2-yl, 4,5-dihydroisoxazol-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, or morpholin-4-yl.

[0101] 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 heterocyclic group containing, in addition to carbon atoms, one or more heteroatoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms. Examples of the 5- to 12-membered monocyclic aromatic heterocyclic heteroaryl group include pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-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, 1,2,4-triazin-6-yl, 1,2,4-triazin-7-yl, 1,2,4-triazin-8-yl, 1,2,4-triazin-9-yl, 1,2,4-triazin-10-yl, 1,2,4-triazin-11-yl, 1,2,4-triazin-12-yl, 1,2,4-triazin-13-yl, 1,2,4-triazin-14-yl, 1,2,4-triazin-15-yl, 1,2,4-triazin-16-yl, 1,2,4-triazin-17-yl, 1,2,4-triazin-18-yl, 1,2,4-triazin-19-yl, 1,2,4-triazin-20-yl, 1,2,4-triazin-21-yl, 1,2,4-triazin-2 , 3,5-triazin-2-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-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, isoxazo 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, 1,3,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-4-yl, 1,3,4-thiadiazol-5-yl, 1,3,4-thiadiazol-3-yl, 1,3,4-thiadiazol-5 ... -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, or 1,2,5-oxadiazol-3-yl groups can be mentioned.As the fused bicyclic aromatic heterocycle, one of the monocyclic groups and a phenyl ring, or one of the monocyclic aromatic heterocycle groups, can be C. ８ ~C １０The term "fused bicyclic aromatic heterocycle" refers to a fused bicyclic ring formed by fusing to form a bicyclic group. Examples of the 5- to 12-membered heteroaryl group of the fused bicyclic aromatic heterocycle include indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, 1,3-benzodioxol-4-yl, 1,3-benzodioxol-5-yl, 2,3-dihydrobenzofuran-4-yl, 2,3-dihydrobenzofuran-5-yl, 2,3-dihydrobenzofuran-6-yl, 2,3-dihydrobenzofuran-7-yl, 1,4-benzodioxan-5-yl, 1,4-benzodioxan-6-yl, chroman-5-yl, chroman-6-yl, chroman-7-yl, chroman-8-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl, benzimidazol-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol- 6-yl, 1H-indazol-7-yl, 1H-benzotriazol-1-yl, 1H-benzotriazol-4-yl, 1H-benzotriazol-5-yl, 1H-benzotriazol-6-yl, 1H-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 benzothiazol-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-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, benzoxazol-2-yl, benzoxazol-4-yl, benzoxazol-5-yl, benzoxazol-6-yl, benzoxazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,Examples of such groups include 2-benzisoxazol-7-yl, pyrazolopyridin-1-yl, pyrazolopyridin-3-yl, pyrazolopyridin-4-yl, pyrazolopyridin-5-yl, pyrazolopyridin-6-yl, quinazolin-2-yl, quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl, quinazolin-8-yl, quinoxalin-2-yl, quinoxalin-5-yl, quinoxalin-6-yl, cinnolin-3-yl, cinnolin-4-yl, cinnolin-5-yl, cinnolin-6-yl, cinnolin-7-yl, and cinnolin-8-yl.

[0102] 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 3- to 6-membered heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridin-2-yloxy, oxiran-2-yloxy, oxetan-2-yloxy, oxetan-3-yloxy, thietan-2-yloxy, thietan-3-yloxy, tetrahydrofuran-2-yloxy, tetrahydrofuran-3-yloxy, tetrahydrofuran-4-yloxy, tetrahydrofuran-5-yloxy, tetrahydrofuran-6-yloxy, tetrahydrofuran-7-yloxy, tetrahydrofuran-8-yloxy, tetrahydrofuran-9-yloxy, tetrahydrofuran-10-yloxy, tetrahydrofuran-11-yloxy, tetrahydrofuran-12-yloxy, tetrahydrofuran-13-yloxy, tetrahydrofuran-14-yloxy, tetrahydrofuran-15-yloxy, tetrahydrofuran-16-yloxy, tetrahydrofuran-17-yloxy, tetrahydrofuran-18-yloxy, tetrahydrofuran-19-yloxy, tetrahydrofuran-20-yloxy, tetrahydrofuran-21-yloxy, tetrahydrofuran-22-yloxy, tetrahydrofuran-23-yloxy, tetrahydrofuran-24-yloxy, tetrahydrofuran-25-yloxy, tetrahydrofuran-26-yloxy, tetrahydrofuran-27-yloxy, tetrahydrofuran-28-yloxy, tetrahydrofuran-29-yloxy, tetrahydrofuran-30-yloxy, tetrahydrofuran-31-yloxy, tetrahydrofuran-29-yloxy, tetrahydrofuran-31-yloxy, Examples of such groups include tetrahydropyran-2-yloxy, tetrahydropyran-3-yloxy, tetrahydropyran-4-yloxy, azetidin-2-yloxy, azetidin-3-yloxy, pyrrolidin-2-yloxy, pyrrolidin-3-yloxy, piperidin-2-yloxy, piperidin-3-yloxy, piperidin-4-yloxy, piperazin-2-yloxy, and 4,5-dihydroisoxazol-3-yloxy.

[0103] In the present invention, "3- to 6-membered heterocyclyl-C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a group in which the 3- to 6-membered heterocyclyl moiety and the alkoxy moiety have the same meaning as above (3- to 6-membered heterocyclyl)-(C １ ~C ６alkoxy)-groups, such as aziridin-2-ylmethoxy, oxiran-2-ylmethoxy, oxetan-2-ylmethoxy, oxetan-3-ylmethoxy, thietan-2-ylmethoxy, thietan-3-ylmethoxy, 2,5-dihydrofuran-3-ylmethoxy, tetrahydrofuran-2-ylmethoxy, tetrahydrofuran-3-ylmethoxy, tetrahydropyran-2-ylmethoxy, tetrahydropyran-3 ... Examples of groups include 4,5-dihydroisoxazol-3-ylmethoxy, 1,3-dioxolan-2-ylmethoxy, 1,3-dioxan-2-ylmethoxy, 1,3-dioxan-2-ylmethoxy, 1,3-dioxan-2-ylmethoxy, 1,3-dioxan-2-ylmethoxy, 1,3-dioxan-4 ...

[0104] 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 5- to 12-membered heteroaryl moiety has the above-mentioned meaning, and examples of the 5- to 12-membered heteroaryl ring include 5- to 12-membered heterocycles such as monocyclic aromatic heterocycles and fused bicyclic aromatic heterocycles.Examples of the 5- to 12-membered heteroaryloxy group of the monocyclic aromatic heterocycle include pyridin-2-yloxy, pyridin-3-yloxy, pyridin-4-yloxy, pyrimidin-2-yloxy, pyrimidin-4-yloxy, pyrimidin-5-yloxy, pyrazin-2-yloxy, pyridazin-3-yloxy, pyridazin-4-yloxy, 1,2,3-triazin-4-yloxy, 1,2,3-triazin-5-yloxy, 1,2,4-triazin-3-yloxy, 1,2,4-triazin-5-yloxy, 1,2,4 -triazin-6-yloxy, 1,3,5-triazin-2-yloxy, thiophen-2-yloxy, thiophen-3-yloxy, furan-2-yloxy, furan-3-yloxy, pyrazol-3-yloxy, pyrazol-4-yloxy, pyrazol-5-yloxy, thiazol-2-yloxy, thiazol-4-yloxy, thiazol-5-yloxy, isothiazol-3-yloxy, isothiazol-4-yloxy, isothiazol-5-yloxy, oxazol-2-yloxy, oxazol-4- yloxy, oxazol-5-yloxy, isoxazol-3-yloxy, isoxazol-4-yloxy, isoxazol-5-yloxy, imidazol-2-yloxy, imidazol-4-yloxy, imidazol-5-yloxy, 1,2,3-triazol-4-yloxy, 1,2,3-triazol-5-yloxy, 1,2,4-triazol-3-yloxy, 1,2,4-triazol-5-yloxy, 1,3,4-thiadiazol-2-yloxy, 1,2,3-thiadiazol-4-yloxy Examples of such groups include 1,2,3-thiadiazol-5-yloxy, 1,2,4-thiadiazol-3-yloxy, 1,2,4-thiadiazol-5-yloxy, 1,2,5-thiadiazol-3-yloxy, 1,3,4-oxadiazol-2-yloxy, 1,2,3-oxadiazol-4-yloxy, 1,2,3-oxadiazol-5-yloxy, 1,2,4-oxadiazol-3-yloxy, 1,2,4-oxadiazol-5-yloxy, and 1,2,5-oxadiazol-3-yloxy.As the fused bicyclic aromatic heterocycle, one of the monocyclic groups and a phenyl ring, or one of the monocyclic aromatic heterocycle groups, can be C. ８ ~C １０The term "fused bicyclic ring" refers to a ring formed by fusing rings together to form a bicyclic group. Examples of the 5- to 12-membered heteroaryloxy group of the fused bicyclic aromatic heterocycle include indol-2-yloxy, indol-3-yloxy, indol-4-yloxy, indol-5-yloxy, indol-6-yloxy, indol-7-yloxy, 1,3-benzodioxol-4-yloxy, 1,3-benzodioxol-5-yloxy, 2,3-dihydrobenzofuran-4-yloxy, 2,3-dihydrobenzofuran-5-yloxy, 2,3-dihydrobenzofuran-6-yloxy, 2,3-dihydrobenzofuran-7-yloxy, 1,4-benzodioxan-5-yloxy, 1,4-benzodioxan-6-yloxy, chroman-5-yloxy, chroman-6-yloxy, chroman-7-yloxy, chroman-8-yloxy, benzimidazol-2-yloxy, benzimidazol-4-yloxy, benzimidazol-5-yloxy, benzimidazol-6-yloxy, benzimidazol-7-yloxy, 1H-indazol-3-yloxy, 1H-indazol-4-yloxy, 1H-indazol-5-yloxy, 1H-indazol-6-yloxy, 1H-indazol-7-yloxy 1H-benzotriazol-4-yloxy, 1H-benzotriazol-5-yloxy, 1H-benzotriazol-6-yloxy, 1H-benzotriazol-7-yloxy, isoquinolin-1-yloxy, isoquinolin-3-yloxy, isoquinolin-4-yloxy, isoquinolin-5-yloxy, isoquinolin-6-yloxy, isoquinolin-7-yloxy, isoquinolin-8-yloxy, quinolin-2-yloxy, quinolin-3-yloxy, quinolin-4-yloxy, quinolin-5-yloxy, quinoline-6 -yloxy, quinolin-7-yloxy, quinolin-8-yloxy, benzothiazol-2-yloxy, benzothiazol-4-yloxy, benzothiazol-5-yloxy, benzothiazol-6-yloxy, benzothiazol-7-yloxy, benzofuran-2-yloxy, benzofuran-3-yloxy, benzofuran-4-yloxy, benzofuran-5-yloxy, benzofuran-6-yloxy, benzofuran-7-yloxy, benzothiophen-2-yloxy, benzothiophen-3-yloxy, benzothiophene benzothiophen-4-yloxy, benzothiophen-5-yloxy, benzothiophen-6-yloxy, benzothiophen-7-yloxy, benzoxazol-2-yloxy, benzoxazol-4-yloxy, benzoxazol-5-yloxy, benzoxazol-6-yloxy, benzoxazol-7-yloxy, 1,2-benzisoxazol-3-yloxy, 1,2-benzisoxazol-4-yloxy, 1,2-benzisoxazol-5-yloxy, 1,2-benzisoxazol-6-yloxy, 1,Examples of such groups include 2-benzisoxazol-7-yloxy, pyrazolopyridin-3-yloxy, pyrazolopyridin-4-yloxy, pyrazolopyridin-5-yloxy, pyrazolopyridin-6-yloxy, quinazolin-2-yloxy, quinazolin-4-yloxy, quinazolin-5-yloxy, quinazolin-6-yloxy, quinazolin-7-yloxy, quinazolin-8-yloxy, quinoxalin-2-yloxy, quinoxalin-5-yloxy, quinoxalin-6-yloxy, cinnolin-3-yloxy, cinnolin-4-yloxy, cinnolin-5-yloxy, cinnolin-6-yloxy, cinnolin-7-yloxy, and cinnolin-8-yloxy.

[0105] In the present invention, "5- to 12-membered heteroaryl-C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a group in which the 5- to 12-membered heteroaryl moiety and the alkoxy moiety have the same meaning as above (5- to 12-membered heteroaryl)-(C １ ~C ６ The 5- to 12-membered heteroaryl ring includes a 5- to 12-membered monocyclic aromatic heterocycle and a fused bicyclic aromatic heterocycle. １ ~C ６Examples of the alkoxy group include pyridin-2-ylmethoxy, pyridin-3-ylmethoxy, pyridin-4-ylmethoxy, pyrimidin-2-ylmethoxy, pyrimidin-4-ylmethoxy, pyrimidin-5-ylmethoxy, pyrazin-2-ylmethoxy, pyridazin-3-ylmethoxy, pyridazin-4-ylmethoxy, 1,2,3-triazin-4-ylmethoxy, 1,2,3-triazin-5-ylmethoxy, 1,2,4-triazin-3-ylmethoxy, 1,2,4-triazin-5-ylmethoxy, 1,2,4-triazin- 6-ylmethoxy, 1,3,5-triazin-2-ylmethoxy, thiophen-2-ylmethoxy, thiophen-3-ylmethoxy, furan-2-ylmethoxy, furan-3-ylmethoxy, pyrazol-3-ylmethoxy, pyrazol-4-ylmethoxy, pyrazol-5-ylmethoxy, thiazol-2-ylmethoxy, thiazol-4-ylmethoxy, thiazol-5-ylmethoxy, isothiazol-3-ylmethoxy, isothiazol-4-ylmethoxy, isothiazol-5-ylmethoxy, oxazol-2-ylmethoxy, Oxazol-4-ylmethoxy, oxazol-5-ylmethoxy, isoxazol-3-ylmethoxy, isoxazol-4-ylmethoxy, isoxazol-5-ylmethoxy, imidazol-2-ylmethoxy, imidazol-4-ylmethoxy, imidazol-5-ylmethoxy, 1,2,3-triazol-4-ylmethoxy, 1,2,3-triazol-5-ylmethoxy, 1,2,4-triazol-3-ylmethoxy, 1,2,4-triazol-5-ylmethoxy, 1,3,4-thiadiazol-2-ylmethoxy 1,2,3-thiadiazol-4-ylmethoxy, 1,2,3-thiadiazol-5-ylmethoxy, 1,2,4-thiadiazol-3-ylmethoxy, 1,2,4-thiadiazol-5-ylmethoxy, 1,2,5-thiadiazol-3-ylmethoxy, 1,3,4-oxadiazol-2-ylmethoxy, 1,2,3-oxadiazol-4-ylmethoxy, 1,2,3-oxadiazol-5-ylmethoxy, 1,2,4-oxadiazol-3-ylmethoxy, 1,2,4-oxadiazol-5-ylmethoxy, or 1,2,Examples of the fused bicyclic aromatic heterocycle include a fused bicyclic aromatic heterocycle in which one of the monocyclic groups and a phenyl ring are bonded together, or one of the monocyclic aromatic heterocycle groups is bonded together with a C, ８ ~C １０ fused to form a bicyclic group. 5-12 membered heteroaryl-C of a fused bicyclic aromatic heterocycle. １ ~C ６Examples of the alkoxy group include indol-2-ylmethoxy, indol-3-ylmethoxy, indol-4-ylmethoxy, indol-5-ylmethoxy, indol-6-ylmethoxy, indol-7-ylmethoxy, 1,3-benzodioxol-4-ylmethoxy, 1,3-benzodioxol-5-ylmethoxy, 2,3-dihydrobenzofuran-4-ylmethoxy, 2,3-dihydrobenzofuran-5-ylmethoxy, 2,3-dihydrobenzofuran-6-ylmethoxy, 2,3-dihydrobenzofuran-7-ylmethoxy, 1,4-benzodioxan-5-ylmethoxy, 1,4-benzodioxan-6-ylmethoxy, chroman-5-ylmethoxy, chroman-6-ylmethoxy, chroman-7-ylmethoxy, chroman-8-ylmethoxy, benzimidazol-2-ylmethoxy, benzimidazol-4-ylmethoxy, benzimidazol-5-ylmethoxy, benzimidazol-6-ylmethoxy, benzimidazol-7-ylmethoxy, 1H-indazol-3-ylmethoxy, 1H-indazol-4-ylmethoxy, 1H-indazol-5-ylmethoxy, 1H-indazol-6-ylmethoxy 1H-indazol-7-ylmethoxy, 1H-benzotriazol-4-ylmethoxy, 1H-benzotriazol-5-ylmethoxy, 1H-benzotriazol-6-ylmethoxy, 1H-benzotriazol-7-ylmethoxy, isoquinolin-1-ylmethoxy, isoquinolin-3-ylmethoxy, isoquinolin-4-ylmethoxy, isoquinolin-5-ylmethoxy, isoquinolin-6-ylmethoxy, isoquinolin-7-ylmethoxy, isoquinolin-8-ylmethoxy, quinolin-2-ylmethoxy, quinolin-3-ylmethoxy benzothiazol-4-ylmethoxy, quinolin-5-ylmethoxy, quinolin-6-ylmethoxy, quinolin-7-ylmethoxy, quinolin-8-ylmethoxy, benzothiazol-2-ylmethoxy, benzothiazol-4-ylmethoxy, benzothiazol-5-ylmethoxy, benzothiazol-6-ylmethoxy, benzothiazol-7-ylmethoxy, benzofuran-2-ylmethoxy, benzofuran-3-ylmethoxy, benzofuran-4-ylmethoxy, benzofuran-5-ylmethoxy, benzofuran-6-ylmethoxy, benzofuran- benzothiophen-7-ylmethoxy, benzothiophen-2-ylmethoxy, benzothiophen-3-ylmethoxy, benzothiophen-4-ylmethoxy, benzothiophen-5-ylmethoxy, benzothiophen-6-ylmethoxy, benzothiophen-7-ylmethoxy, benzoxazol-2-ylmethoxy, benzoxazol-4-ylmethoxy, benzoxazol-5-ylmethoxy, benzoxazol-6-ylmethoxy, benzoxazol-7-ylmethoxy, 1,2-benzisoxazol-3-ylmethoxy, 1,2-benzisoxazol-4-ylmethoxy, 1,2-benzisoxazol-5-ylmethoxy, 1,2-benzisoxazol-6-ylmethoxy, 1,2-benzisoxazol-7-ylmethoxy, pyrazolopyridin-3-ylmethoxy, pyrazolopyridin-4-ylmethoxy, pyrazolopyridin-5-ylmethoxy, pyrazolopyridin-6-ylmethoxy, quinazolin-2-ylmethoxy, quinazolin-4-ylmethoxy, quinazoline- Examples of groups include 5-ylmethoxy, quinazolin-6-ylmethoxy, quinazolin-7-ylmethoxy, quinazolin-8-ylmethoxy, quinoxalin-2-ylmethoxy, quinoxalin-5-ylmethoxy, quinoxalin-6-ylmethoxy, cinnolin-3-ylmethoxy, cinnolin-4-ylmethoxy, cinnolin-5-ylmethoxy, cinnolin-6-ylmethoxy, cinnolin-7-ylmethoxy, and cinnolin-8-ylmethoxy.

[0106] In the present invention, "5- to 12-membered heteroaryl-C ２ ~C ６ Unless otherwise specified, the term "alkynyl group" refers to a group in which the 5- to 12-membered heteroaryl moiety and the alkynyl moiety have the same meaning as above (5- to 12-membered heteroaryl)-(C ２ ~C ６ The 5- to 12-membered heteroaryl represents a alkynyl group, and examples of the 5- to 12-membered heteroaryl include monocyclic aromatic heterocycles and fused bicyclic aromatic heterocycles. ２ ~C ６Examples of the alkynyl group include pyridin-2-ylethynyl, pyridin-3-ylethynyl, pyridin-4-ylethynyl, pyrimidin-2-ylethynyl, pyrimidin-4-ylethynyl, pyrimidin-5-ylethynyl, pyrazin-2-ylethynyl, pyridazin-3-ylethynyl, pyridazin-4-ylethynyl, 1,2,3-triazin-4-ylethynyl, 1,2,3-triazin-5-ylethynyl, 1,2,4-triazin-3-ylethynyl, 1,2,4-triazin-5-ylethynyl, 1,2,4-triazin- 6-ylethynyl, 1,3,5-triazin-2-ylethynyl, thiophen-2-ylethynyl, thiophen-3-ylethynyl, furan-2-ylethynyl, furan-3-ylethynyl, pyrazol-3-ylethynyl, pyrazol-4-ylethynyl, pyrazol-5-ylethynyl, thiazol-2-ylethynyl, thiazol-4-ylethynyl, thiazol-5-ylethynyl, isothiazol-3-ylethynyl, isothiazol-4-ylethynyl, isothiazol-5-ylethynyl, oxazol-2-ylethynyl, Oxazol-4-ylethynyl, oxazol-5-ylethynyl, isoxazol-3-ylethynyl, isoxazol-4-ylethynyl, isoxazol-5-ylethynyl, imidazol-2-ylethynyl, imidazol-4-ylethynyl, imidazol-5-ylethynyl, 1,2,3-triazol-4-ylethynyl, 1,2,3-triazol-5-ylethynyl, 1,2,4-triazol-3-ylethynyl, 1,2,4-triazol-5-ylethynyl, 1,3,4-thiadiazol-2-ylethynyl thiadiazol-4-ylethynyl, 1,2,3-thiadiazol-5-ylethynyl, 1,2,4-thiadiazol-3-ylethynyl, 1,2,4-thiadiazol-5-ylethynyl, 1,2,5-thiadiazol-3-ylethynyl, 1,3,4-oxadiazol-2-ylethynyl, 1,2,3-oxadiazol-4-ylethynyl, 1,2,3-oxadiazol-5-ylethynyl, 1,2,4-oxadiazol-3-ylethynyl, 1,2,4-oxadiazol-5-ylethynyl, or 1,2,Examples of the fused bicyclic aromatic heterocycle include a fused bicyclic aromatic heterocycle in which one of the monocyclic groups and a phenyl ring are bonded together, or one of the monocyclic aromatic heterocycle groups is bonded together with a C, ８ ~C １０ fused to form a bicyclic group. 5-12 membered heteroaryl-C of a fused bicyclic aromatic heterocycle. ２ ~C ６Examples of the alkynyl group include indol-2-ylethynyl, indol-3-ylethynyl, indol-4-ylethynyl, indol-5-ylethynyl, indol-6-ylethynyl, indol-7-ylethynyl, 1,3-benzodioxol-4-ylethynyl, 1,3-benzodioxol-5-ylethynyl, 2,3-dihydrobenzofuran-4-ylethynyl, 2,3-dihydrobenzofuran-5-ylethynyl, 2,3-dihydrobenzofuran-6-ylethynyl, 2,3-dihydrobenzofuran-7-ylethynyl, 1,4-benzodioxan-5-ylethynyl, 1,4-benzodioxan-6-ylethynyl, chroman-5-ylethynyl, chroman-6-ylethynyl, chroman-7-ylethynyl, chroman-8-ylethynyl, benzimidazol-2-ylethynyl, benzimidazol-4-ylethynyl, benzimidazol-5-ylethynyl, benzimidazol-6-ylethynyl, benzimidazol-7-ylethynyl, 1H-indazol-3-ylethynyl, 1H-indazol-4-ylethynyl, 1H-indazol-5-ylethynyl, 1H-indazol-6-ylethynyl 1H-indazol-7-ylethynyl, 1H-benzotriazol-4-ylethynyl, 1H-benzotriazol-5-ylethynyl, 1H-benzotriazol-6-ylethynyl, 1H-benzotriazol-7-ylethynyl, isoquinolin-1-ylethynyl, isoquinolin-3-ylethynyl, isoquinolin-4-ylethynyl, isoquinolin-5-ylethynyl, isoquinolin-6-ylethynyl, isoquinolin-7-ylethynyl, isoquinolin-8-ylethynyl, quinolin-2-ylethynyl, quinolin-3-ylethynyl thynyl, quinolin-4-ylethynyl, quinolin-5-ylethynyl, quinolin-6-ylethynyl, quinolin-7-ylethynyl, quinolin-8-ylethynyl, benzothiazol-2-ylethynyl, benzothiazol-4-ylethynyl, benzothiazol-5-ylethynyl, benzothiazol-6-ylethynyl, benzothiazol-7-ylethynyl, benzofuran-2-ylethynyl, benzofuran-3-ylethynyl, benzofuran-4-ylethynyl, benzofuran-5-ylethynyl, benzofuran-6-ylethynyl, benzofuran- benzothiophen-7-ylethynyl, benzothiophen-2-ylethynyl, benzothiophen-3-ylethynyl, benzothiophen-4-ylethynyl, benzothiophen-5-ylethynyl, benzothiophen-6-ylethynyl, benzothiophen-7-ylethynyl, benzoxazol-2-ylethynyl, benzoxazol-4-ylethynyl, benzoxazol-5-ylethynyl, benzoxazol-6-ylethynyl, benzoxazol-7-ylethynyl, 1,2-benzisoxazol-3-ylethynyl, 1,2-benzisoxazol-4-ylethynyl, 1,2-benzisoxazol-5-ylethynyl, 1,2-benzisoxazol-6-ylethynyl, 1,2-benzisoxazol-7-ylethynyl, pyrazolopyridin-3-ylethynyl, pyrazolopyridin-4-ylethynyl, pyrazolopyridin-5-ylethynyl, pyrazolopyridin-6-ylethynyl, quinazolin-2-ylethynyl, quinazolin-4-ylethynyl, quinazoline- Examples of groups include 5-ylethynyl, quinazolin-6-ylethynyl, quinazolin-7-ylethynyl, quinazolin-8-ylethynyl, quinoxalin-2-ylethynyl, quinoxalin-5-ylethynyl, quinoxalin-6-ylethynyl, cinnolin-3-ylethynyl, cinnolin-4-ylethynyl, cinnolin-5-ylethynyl, cinnolin-6-ylethynyl, cinnolin-7-ylethynyl, and cinnolin-8-ylethynyl.

[0107] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylamino group" has the above meaning (C １ ~C ６ alkyl)-NH- group, and examples thereof include methylamino, ethylamino, isopropylamino, tert-butylamino, n-propylamino, sec-butylamino, isobutylamino, n-butylamino, 2-methylbutan-1-ylamino, 2-ethylbutan-2-ylamino, 3-methylbutan-2-ylamino, n-pentylamino, 2-methylpentan-2-ylamino, pentan-3-ylamino, isopentylamino, neopentylamino, sec-pentylamino, tert-pentylamino, and n-hexylamino groups.

[0108] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylamino group" has the same meaning as defined above (C １ ~C ６haloalkyl)-NH- group, and examples thereof include 2-fluoroethylamino, 2,2-difluoroethylamino, 2,2,2-trifluoroethylamino, 2,2,2-trichloroethylamino, pentafluoroethylamino, 3,3,3-trifluoropropylamino, and 1,1,1,3,3,3-hexafluoro-2-propylamino groups.

[0109] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylamino group" has the above meaning (C ３ ~C ８ cycloalkyl)-NH- group, and examples thereof include cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, and cyclooctylamino groups.

[0110] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylamino group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-NH- group, and examples thereof include 1-methylcyclopropylamino, 1-methylcyclobutylamino, 1-methylcyclopentylamino, and 1-methylcyclohexylamino groups.

[0111] In the present invention, the term "aminocarbonyl group" refers to a ２ It represents an N—C(═O)— group.

[0112] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylaminocarbonyl group" has the above meaning (C １ ~C ６alkyl)-NH-C(=O)- group, and examples thereof include methylaminocarbonyl, ethylaminocarbonyl, isopropylaminocarbonyl, tert-butylaminocarbonyl, n-propylaminocarbonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl, n-butylaminocarbonyl, 2-methylbutan-1-ylaminocarbonyl, 2-ethylbutan-2-ylaminocarbonyl, 3-methylbutan-2-ylaminocarbonyl, n-pentylaminocarbonyl, 2-methylpentan-2-ylaminocarbonyl, pentan-3-ylaminocarbonyl, isopentylaminocarbonyl, neopentylaminocarbonyl, sec-pentylaminocarbonyl, tert-pentylaminocarbonyl, and n-hexylaminocarbonyl.

[0113] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylaminocarbonyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-NH-C(=O)- group, and examples thereof include 2-fluoroethylaminocarbonyl, 2,2-difluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,2-trichloroethylaminocarbonyl, pentafluoroethylaminocarbonyl, and 1,1,1,3,3,3-hexafluoro-2-propylaminocarbonyl groups.

[0114] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylaminocarbonyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-NH-C(=O)- group, and examples thereof include cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cycloheptylaminocarbonyl, and cyclooctylaminocarbonyl groups.

[0115] In the present invention, "C１ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylaminocarbonyl group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-NH-C(=O)- group, and examples thereof include 1-methylcyclopropylaminocarbonyl, 1-methylcyclobutylaminocarbonyl, 1-methylcyclopentylaminocarbonyl, and 1-methylcyclohexylaminocarbonyl groups.

[0116] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonylamino group" has the above meaning (C １ ~C ６ alkyl)-C(═O)—NH— group, and examples thereof include methylcarbonylamino, ethylcarbonylamino, isopropylcarbonylamino, tert-butylcarbonylamino, n-propylcarbonylamino, sec-butylcarbonylamino, isobutylcarbonylamino, n-butylcarbonylamino, 2-methylbutan-1-ylcarbonylamino, 3-methylbutan-2-ylcarbonylamino, n-pentylcarbonylamino, pentan-3-ylcarbonylamino, isopentylcarbonylamino, neopentylcarbonylamino, sec-pentylcarbonylamino, tert-pentylcarbonylamino, and n-hexylcarbonylamino groups.

[0117] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylcarbonylamino group" has the same meaning as above (C １ ~C ６haloalkyl)-C(═O)—NH— group, and examples thereof include fluoromethylcarbonylamino, difluoromethylcarbonylamino, trifluoromethylcarbonylamino, chloromethylcarbonylamino, bromomethylcarbonylamino, trichloromethylcarbonylamino, tribromomethylcarbonylamino, 2,2-difluoroethylcarbonylamino, 2,2,2-trifluoroethylcarbonylamino, and 3,3,3-trifluoropropylcarbonylamino groups.

[0118] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylcarbonylamino group" has the above meaning (C ３ ~C ８ cycloalkyl)-C(═O)—NH— group, and examples thereof include cyclopropanecarbonylamino, cyclobutanecarbonylamino, cyclopentanecarbonylamino, cyclohexanecarbonylamino, cycloheptanecarbonylamino, and cyclooctanecarbonyl groups.

[0119] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylcarbonylamino group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above, and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-C(═O)—NH— group, and examples thereof include 1-methylcyclopropanecarbonylamino, 1-methylcyclobutanecarbonylamino, 1-methylcyclopentanecarbonylamino, and 1-methylcyclohexanecarbonylamino groups.

[0120] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkoxy moiety of the "alkoxycarbonylamino group" has the above meaning (C １ ~C６ alkoxy)-C(═O)—NH— group, and examples thereof include methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino, n-propoxycarbonylamino, sec-butoxycarbonylamino, isobutoxycarbonylamino, n-butoxycarbonylamino, 2-methylbutan-1-yloxycarbonylamino, 2-ethylbutan-2-yloxycarbonylamino, 3-methylbutan-2-yloxycarbonylamino, n-pentyloxycarbonylamino, 2-methylpentan-2-yloxycarbonylamino, pentan-3-yloxycarbonylamino, isopentyloxycarbonylamino, neopentyloxycarbonylamino, sec-pentyloxycarbonylamino, tert-pentyloxycarbonylamino, and n-hexyloxycarbonylamino groups.

[0121] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkoxycarbonylamino group has the same meaning as defined above (C １ ~C ６ haloalkyl)-O-C(=O)-NH- group, and examples thereof include difluoromethoxycarbonylamino, dichloromethoxycarbonylamino, trifluoromethoxycarbonylamino, 2-fluoroethoxycarbonylamino, 2-chloroethoxycarbonylamino, 2,2-difluoroethoxycarbonylamino, 2,2,2-trifluoroethoxycarbonylamino, 1,1,2,2-tetrafluoroethoxycarbonylamino, pentafluoroethoxycarbonylamino, 2-chloro-1,1,2-trifluoroethoxycarbonylamino, and 2-chloro-1,1,2,2-tetrafluoroethoxycarbonylamino.

[0122] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkoxycarbonylamino group has the above-mentioned meaning in the cycloalkyl portion (C ３ ~C ８cycloalkyl)-O-C(=O)-NH- group, and examples thereof include cyclopropyloxycarbonylamino, cyclobutyloxycarbonylamino, cyclopentyloxycarbonylamino, cyclohexyloxycarbonylamino, cycloheptyloxycarbonylamino, and cyclooctyloxycarbonylamino groups.

[0123] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkoxycarbonylamino group" refers to a group in which the alkyl portion and the cycloalkoxy portion have the same meaning as above, and an alkyl group is substituted on the cycloalkoxy portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkoxy)-C(═O)—NH— group, and examples thereof include 1-methylcyclopropyloxycarbonylamino, 1-methylcyclobutyloxycarbonylamino, 1-methylcyclopentyloxycarbonylamino, 1-methylcyclohexyloxycarbonylamino, 1-methylcycloheptyloxycarbonylamino, and 1-methylcyclooctyloxycarbonylamino groups.

[0124] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl portion of the "alkylaminocarbonylamino group" has the above meaning (C １ ~C ６alkyl)-NH-C(=O)-NH- group, and examples thereof include methylaminocarbonylamino, ethylaminocarbonylamino, isopropylaminocarbonylamino, tert-butylaminocarbonylamino, n-propylaminocarbonylamino, sec-butylaminocarbonylamino, isobutylaminocarbonylamino, n-butylaminocarbonylamino, 2-methylbutan-1-ylaminocarbonylamino, 2-ethylbutan-2-ylaminocarbonylamino, 3-methylbutan-2-ylaminocarbonylamino, n-pentylaminocarbonylamino, 2-methylpentan-2-ylaminocarbonylamino, pentan-3-ylaminocarbonylamino, isopentylaminocarbonylamino, neopentylaminocarbonylamino, sec-pentylaminocarbonylamino, tert-pentylaminocarbonylamino, and n-hexylaminocarbonylamino groups.

[0125] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylaminocarbonylamino group" has the same meaning as above (C １ ~C ６ haloalkyl)-NH-C(═O)-NH- group, and examples thereof include 2-fluoroethylaminocarbonylamino, 2,2-difluoroethylcarbonylamino, 2,2,2-trifluoroethylaminocarbonylamino, 2,2,2-trichloroethylaminocarbonylamino, pentafluoroethylaminocarbonylamino, and 1,1,1,3,3,3-hexafluoro-2-propylaminocarbonylamino groups.

[0126] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylaminocarbonylamino group" has the above meaning (C ３ ~C ８cycloalkyl)-NH-C(=O)-NH- group, and examples thereof include cyclopropylaminocarbonylamino, cyclobutylaminocarbonylamino, cyclopentylaminocarbonylamino, cyclohexylaminocarbonylamino, cycloheptylaminocarbonylamino, and cyclooctylaminocarbonylamino groups.

[0127] In the present invention, "C １ ~C ６ Alkyl-C ３ ~C ８ Unless otherwise specified, the term "cycloalkylaminocarbonylamino group" refers to a group in which the alkyl and cycloalkyl portions have the same meanings as above and an alkyl group is substituted on the cycloalkyl portion (C １ ~C ６ alkyl)-(C ３ ~C ８ cycloalkyl)-NH-C(═O)-NH- group, and examples thereof include 1-methylcyclopropylaminocarbonylamino, 1-methylcyclobutylaminocarbonylamino, 1-methylcyclopentylaminocarbonylamino, 1-methylcyclohexylaminocarbonylamino, 1-methylcycloheptylaminocarbonylamino, and 1-methylcyclooctylaminocarbonylamino groups.

[0128] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylcarbonylamino group" has the above meaning (C ６ ~C １２ aryl)-C(=O)-NH- group, and examples thereof include phenylcarbonylamino, naphthalen-1-ylcarbonylamino, and naphthalen-2-ylcarbonylamino groups.

[0129] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylcarbonylamino group" refers to a (3- to 6-membered heterocyclyl)-C(═O)-NH- group in which the 3- to 6-membered heterocyclyl moiety has the above meaning, and examples thereof include aziridin-1-ylcarbonylamino, aziridin-2-ylcarbonylamino, oxiran-2-ylcarbonylamino, oxetan-2-ylcarbonylamino, oxetan-3-ylcarbonylamino, thietan-2-ylcarbonylamino, thietan-3-ylcarbonylamino, tetrahydrofuran-2-ylcarbonylamino, tetrahydrofuran-3-ylcarbonylamino, tetrahydropyran-2-ylcarbonylamino, and tetrahydropyran-3-ylcarbonylamino. amino, tetrahydropyran-4-ylcarbonylamino, azetidin-1-ylcarbonylamino, azetidin-2-ylcarbonylamino, azetidin-3-ylcarbonylamino, pyrrolidin-1-ylcarbonylamino, pyrrolidin-2-ylcarbonylamino, pyrrolidin-3-ylcarbonylamino, piperidin-1-ylcarbonylamino, piperidin-2-ylcarbonylamino, piperidin-3-ylcarbonylamino, piperidin-4-ylcarbonylamino, piperazin-1-ylcarbonylamino, piperazin-2-ylcarbonylamino, 4,5-dihydroisoxazol-3-ylcarbonylamino, or morpholin-4-ylcarbonylamino.

[0130] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylcarbonylamino group" refers to a (5- to 12-membered heteroaryl)-C(═O)-NH- group in which the 5- to 12-membered heteroaryl moiety has the above meaning, and examples of the 5- to 12-membered heteroaryl ring include monocyclic aromatic heterocycles and fused bicyclic aromatic heterocycles. Examples of the 5- to 12-membered heteroarylcarbonylamino group of a monocyclic aromatic heterocycle include pyridin-2-ylcarbonylamino, pyridin-3-ylcarbonylamino, pyridin-4-ylcarbonylamino, pyrimidin-2-ylcarbonylamino, pyrimidin-4-ylcarbonylamino, pyrimidin-5-ylcarbonylamino, pyrazin-2-ylcarbonylamino, pyridazin-3-ylcarbonylamino, pyridazin-4-ylcarbonylamino, 1-methyl-2-methyl-1-pyrid ... , 2,3-triazin-4-ylcarbonylamino, 1,2,3-triazin-5-ylcarbonylamino, 1,2,4-triazin-3-ylcarbonylamino, 1,2,4-triazin-5-ylcarbonylamino, 1,2,4-triazin-6-ylcarbonylamino, 1,3,5-triazin-2-ylcarbonylamino, thiophen-2-ylcarbonylamino, thiophen-3-ylcarbonylamino, furan-2-ylcarbonylamino, furan-3 -ylcarbonylamino, pyrazol-1-ylcarbonylamino, pyrazol-3-ylcarbonylamino, pyrazol-4-ylcarbonylamino, pyrazol-5-ylcarbonylamino, thiazol-2-ylcarbonylamino, thiazol-4-ylcarbonylamino, thiazol-5-ylcarbonylamino, isothiazol-3-ylcarbonylamino, isothiazol-4-ylcarbonylamino, isothiazol-5-ylcarbonylamino, o oxazol-2-ylcarbonylamino, oxazol-4-ylcarbonylamino, oxazol-5-ylcarbonylamino, isoxazol-3-ylcarbonylamino, isoxazol-4-ylcarbonylamino, isoxazol-5-ylcarbonylamino, imidazol-1-ylcarbonylamino, imidazol-2-ylcarbonylamino, imidazol-4-ylcarbonylamino, imidazol-5-ylcarbonylamino, 1,2,3-triazol-1-ylcarbonylamino, 1,2,3-triazol-4-ylcarbonylamino, 1,2,3-triazol-5-ylcarbonylamino, 1,2,4-triazol-1-ylcarbonylamino, 1,2,4-triazol-3-ylcarbonylamino, 1,2,4-triazol-5-ylcarbonylamino, 1,3,4-thiadiazol-2-ylcarbonylamino, 1,2,3-thiadiazol-4-ylcarbonylamino, 1,2,3-thiadiazol-5-ylcarbonylamino, 1,2,4-thiadiazol-3 Examples of the fused bicyclic aromatic heterocycle include a fused bicyclic aromatic heterocycle in which one of the monocyclic groups and the phenyl ring are bonded together, or one of the monocyclic aromatic heterocycle groups is bonded together, by a C, ８ ~C １０The term "fused bicyclic ring" refers to a ring formed by fusing the rings together to form a bicyclic group. Examples of the 5- to 12-membered heteroarylcarbonylamino group of the fused bicyclic aromatic heterocycle include indol-1-ylcarbonylamino, indol-2-ylcarbonylamino, indol-3-ylcarbonylamino, indol-4-ylcarbonylamino, indol-5-ylcarbonylamino, indol-6-ylcarbonylamino, indol-7-ylcarbonylamino, 1,3-benzodioxol-4-ylcarbonylamino, 1,3-benzodioxol-5-ylcarbonylamino, 2,3-dihydro ... Benzofuran-4-ylcarbonylamino, 2,3-dihydrobenzofuran-5-ylcarbonylamino, 2,3-dihydrobenzofuran-6-ylcarbonylamino, 2,3-dihydrobenzofuran-7-ylcarbonylamino, 1,4-benzodioxan-5-ylcarbonylamino, 1,4-benzodioxan-6-ylcarbonylamino, chroman-5-ylcarbonylamino, chroman-6-ylcarbonylamino, chroman-7-ylcarbonylamino, chroman-8-ylcarbonylamino, benzimidazole- 1-ylcarbonylamino, benzimidazol-2-ylcarbonylamino, benzimidazol-4-ylcarbonylamino, benzimidazol-5-ylcarbonylamino, benzimidazol-6-ylcarbonylamino, benzimidazol-7-ylcarbonylamino, 1H-indazol-1-ylcarbonylamino, 1H-indazol-3-ylcarbonylamino, 1H-indazol-4-ylcarbonylamino, 1H-indazol-5-ylcarbonylamino, 1H-indazol-6-ylcarbonylamino ylamino, 1H-indazol-7-ylcarbonylamino, 1H-benzotriazol-1-ylcarbonylamino, 1H-benzotriazol-4-ylcarbonylamino, 1H-benzotriazol-5-ylcarbonylamino, 1H-benzotriazol-6-ylcarbonylamino, 1H-benzotriazol-7-ylcarbonylamino, isoquinolin-1-ylcarbonylamino, isoquinolin-3-ylcarbonylamino, isoquinolin-4-ylcarbonylamino, isoquinolin-5-ylcarbonylamino,Isoquinolin-6-ylcarbonylamino, isoquinolin-7-ylcarbonylamino, isoquinolin-8-ylcarbonylamino, quinolin-2-ylcarbonylamino, quinolin-3-ylcarbonylamino, quinolin-4-ylcarbonylamino, quinolin-5-ylcarbonylamino, quinolin-6-ylcarbonylamino, quinolin-7-ylcarbonylamino, quinolin-8-ylcarbonylamino, benzothiazol-2-ylcarbonylamino, benzothiazol-4-ylcarbonylamino, benzothiazol-5-ylcarbonyl Amino, benzothiazol-6-ylcarbonylamino, benzothiazol-7-ylcarbonylamino, benzofuran-2-ylcarbonylamino, benzofuran-3-ylcarbonylamino, benzofuran-4-ylcarbonylamino, benzofuran-5-ylcarbonylamino, benzofuran-6-ylcarbonylamino, benzofuran-7-ylcarbonylamino, benzothiophen-2-ylcarbonylamino, benzothiophen-3-ylcarbonylamino, benzothiophen-4-ylcarbonylamino, benzothiophen-5-ylcarbonylamino benzothiophen-6-ylcarbonylamino, benzothiophen-7-ylcarbonylamino, benzoxazol-2-ylcarbonylamino, benzoxazol-4-ylcarbonylamino, benzoxazol-5-ylcarbonylamino, benzoxazol-6-ylcarbonylamino, benzoxazol-7-ylcarbonylamino, 1,2-benzisoxazol-3-ylcarbonylamino, 1,2-benzisoxazol-4-ylcarbonylamino, 1,2-benzisoxazol-5-ylcarbonyl ylamino, 1,2-benzisoxazol-6-ylcarbonylamino, 1,2-benzisoxazol-7-ylcarbonylamino, pyrazolopyridin-1-ylcarbonylamino, pyrazolopyridin-3-ylcarbonylamino, pyrazolopyridin-4-ylcarbonylamino, pyrazolopyridin-5-ylcarbonylamino, pyrazolopyridin-6-ylcarbonylamino, quinazolin-2-ylcarbonylamino, quinazolin-4-ylcarbonylamino, quinazolin-5-ylcarbonylamino, quinazolin-6-ylcarbonylamino,Examples of such groups include quinazolin-7-ylcarbonylamino, quinazolin-8-ylcarbonylamino, quinoxalin-2-ylcarbonylamino, quinoxalin-5-ylcarbonylamino, quinoxalin-6-ylcarbonylamino, cinnolin-3-ylcarbonylamino, cinnolin-4-ylcarbonylamino, cinnolin-5-ylcarbonylamino, cinnolin-6-ylcarbonylamino, cinnolin-7-ylcarbonylamino, and cinnolin-8-ylcarbonylamino.

[0131] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylaminocarbonyl group" has the above meaning (C ６ ~C １２ aryl)-NH-C(=O)- group, and examples thereof include phenylaminocarbonyl, naphthalen-1-ylaminocarbonyl, and naphthalen-2-ylaminocarbonyl groups.

[0132] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylaminocarbonyl group" refers to a (3- to 6-membered heterocyclyl)-NH-C(=O)- group in which the 3- to 6-membered heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridin-2-ylaminocarbonyl, oxiran-2-ylaminocarbonyl, oxetan-2-ylaminocarbonyl, oxetan-3-ylaminocarbonyl, thietan-2-ylaminocarbonyl, thietan-3-ylaminocarbonyl, tetrahydrofuran-2-ylaminocarbonyl, tetrahydrofuran-3-ylaminocarbonyl, tetrahydrofuran-4-ylaminocarbonyl, tetrahydrofuran-5-ylaminocarbonyl, tetrahydrofuran-6-ylaminocarbonyl, tetrahydrofuran-7-ylaminocarbonyl, tetrahydrofuran-8-ylaminocarbonyl, tetrahydrofuran-9-ylaminocarbonyl, tetrahydrofuran-10-ylaminocarbonyl, tetrahydrofuran-11-ylaminocarbonyl, tetrahydrofuran-12-ylaminocarbonyl, tetrahydrofuran-13-ylaminocarbonyl, tetrahydrofuran-14-ylaminocarbonyl, tetrahydrofuran-15-ylaminocarbonyl, tetrahydrofuran-16-ylaminocarbonyl, tetrahydrofuran-17-ylaminocarbonyl, tetrahydrofuran-18-ylaminocarbonyl, tetrahydrofuran-19-ylaminocarbonyl, tetrahydrofuran-20-ylaminocarbonyl, tetrahydrofuran-21-ylaminocarbonyl, tetrahydrofuran-22-ylaminocarbonyl, tetrahydrofuran-23-ylaminocarbonyl, tetrahydrofuran-24-ylaminocarbonyl, tetrahydrofuran-25-ylaminocarbonyl, tetrahydrofuran-26-ylaminocarbonyl, tetrahydrofuran-27-ylaminocarbonyl, Examples of such groups include tetrahydropyran-2-ylaminocarbonyl, tetrahydropyran-3-ylaminocarbonyl, tetrahydropyran-4-ylaminocarbonyl, azetidin-2-ylaminocarbonyl, azetidin-3-ylaminocarbonyl, pyrrolidin-2-ylaminocarbonyl, pyrrolidin-3-ylaminocarbonyl, piperidin-2-ylaminocarbonyl, piperidin-3-ylaminocarbonyl, piperidin-4-ylaminocarbonyl, piperazin-2-ylaminocarbonyl, and 4,5-dihydroisoxazol-3-ylaminocarbonyl.

[0133] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylaminocarbonyl group" refers to a (5- to 12-membered heteroaryl)-NH-C(=O)- group in which the 5- to 12-membered heteroaryl moiety has the above meaning, and examples of the 5- to 12-membered heteroaryl ring include monocyclic aromatic heterocycles and fused bicyclic aromatic heterocycles. Examples of the 5- to 12-membered heteroaryl aminocarbonyl group of a monocyclic aromatic heterocycle include pyridin-2-ylaminocarbonyl, pyridin-3-ylaminocarbonyl, pyridin-4-ylaminocarbonyl, pyrimidin-2-ylaminocarbonyl, pyrimidin-4-ylaminocarbonyl, pyrimidin-5-ylaminocarbonyl, pyrazin-2-ylaminocarbonyl, pyridazin-3-ylaminocarbonyl, pyridazin-4-ylaminocarbonyl, 1,2, 3-triazin-4-ylaminocarbonyl, 1,2,3-triazin-5-ylaminocarbonyl, 1,2,4-triazin-3-ylaminocarbonyl, 1,2,4-triazin-5-ylaminocarbonyl, 1,2,4-triazin-6-ylaminocarbonyl, 1,3,5-triazin-2-ylaminocarbonyl, thiophen-2-ylaminocarbonyl, thiophen-3-ylaminocarbonyl, furan-2-ylaminocarbonyl, furan-3-ylamino Carbonyl, pyrazol-3-ylaminocarbonyl, pyrazol-4-ylaminocarbonyl, pyrazol-5-ylaminocarbonyl, thiazol-2-ylaminocarbonyl, thiazol-4-ylaminocarbonyl, thiazol-5-ylaminocarbonyl, isothiazol-3-ylaminocarbonyl, isothiazol-4-ylaminocarbonyl, isothiazol-5-ylaminocarbonyl, oxazol-2-ylaminocarbonyl, oxazol-4- ylaminocarbonyl, oxazol-5-ylaminocarbonyl, isoxazol-3-ylaminocarbonyl, isoxazol-4-ylaminocarbonyl, isoxazol-5-ylaminocarbonyl, imidazol-2-ylaminocarbonyl, imidazol-4-ylaminocarbonyl, imidazol-5-ylaminocarbonyl, 1,2,3-triazol-4-ylaminocarbonyl, 1,2,3-triazol-5-ylaminocarbonyl, 1,2,4-triazol-3-ylaminocarbonyl, 1,2,4-triazol-5-ylaminocarbonyl, 1,3,4-thiadiazol-2-ylaminocarbonyl, 1,2,3-thiadiazol-4-ylaminocarbonyl, 1,2,3-thiadiazol-5-ylaminocarbonyl, 1,2,4-thiadiazol-3-ylaminocarbonyl, 1,2,4-thiadiazol-5-ylaminocarbonyl, 1,2,5-thiadiazole Examples of the fused bicyclic aromatic heterocycle include a fused bicyclic aromatic heterocycle in which one of the monocyclic groups and a phenyl ring are bonded together, or one of the monocyclic aromatic heterocycle groups is bonded together, by a C, ８ ~C １０The term "fused bicyclic ring" refers to a ring formed by fusing the rings together to form a bicyclic group. Examples of the 5- to 12-membered heteroarylaminocarbonyl group of the fused bicyclic aromatic heterocycle include indol-2-ylaminocarbonyl, indol-3-ylaminocarbonyl, indol-4-ylaminocarbonyl, indol-5-ylaminocarbonyl, indol-6-ylaminocarbonyl, indol-7-ylaminocarbonyl, 1,3-benzodioxol-4-ylaminocarbonyl, 1,3-benzodioxol-5-ylaminocarbonyl, 2,3-dihydrobenzofuran-4-ylaminocarbonyl, 2,3-dihydrobenzofuran-5-ylaminocarbonyl, 2,3-dihydrobenzofuran-6-ylaminocarbonyl, 2,3-dihydrobenzofuran-7-ylaminocarbonyl, 1,4-benzodioxan-5-ylaminocarbonyl, 1,4-benzodioxan-6-ylaminocarbonyl, chroman-5-ylaminocarbonyl, chroman-6-ylaminocarbonyl, chroman-7-ylaminocarbonyl, chroman-8-ylaminocarbonyl, benzimidazol-2-ylaminocarbonyl, benzimidazo 1H-indazol-4-ylaminocarbonyl, benzimidazol-5-ylaminocarbonyl, benzimidazol-6-ylaminocarbonyl, benzimidazol-7-ylaminocarbonyl, 1H-indazol-3-ylaminocarbonyl, 1H-indazol-4-ylaminocarbonyl, 1H-indazol-5-ylaminocarbonyl, 1H-indazol-6-ylaminocarbonyl, 1H-indazol-7-ylaminocarbonyl, 1H-benzotriazol-4-ylaminocarbonyl, 1H-benzotriazol-5 -ylaminocarbonyl, 1H-benzotriazol-6-ylaminocarbonyl, 1H-benzotriazol-7-ylaminocarbonyl, isoquinolin-1-ylaminocarbonyl, isoquinolin-3-ylaminocarbonyl, isoquinolin-4-ylaminocarbonyl, isoquinolin-5-ylaminocarbonyl, isoquinolin-6-ylaminocarbonyl, isoquinolin-7-ylaminocarbonyl, isoquinolin-8-ylaminocarbonyl, quinolin-2-ylaminocarbonyl, quinolin-3-ylaminocarbonyl,Quinolin-4-ylaminocarbonyl, quinolin-5-ylaminocarbonyl, quinolin-6-ylaminocarbonyl, quinolin-7-ylaminocarbonyl, quinolin-8-ylaminocarbonyl, benzothiazol-2-ylaminocarbonyl, benzothiazol-4-ylaminocarbonyl, benzothiazol-5-ylaminocarbonyl, benzothiazol-6-ylaminocarbonyl, benzothiazol-7-ylaminocarbonyl, benzofuran-2-ylaminocarbonyl, benzofuran-3-ylaminocarbonyl, benzofuran-4 -ylaminocarbonyl, benzofuran-5-ylaminocarbonyl, benzofuran-6-ylaminocarbonyl, benzofuran-7-ylaminocarbonyl, benzothiophen-2-ylaminocarbonyl, benzothiophen-3-ylaminocarbonyl, benzothiophen-4-ylaminocarbonyl, benzothiophen-5-ylaminocarbonyl, benzothiophen-6-ylaminocarbonyl, benzothiophen-7-ylaminocarbonyl, benzoxazol-2-ylaminocarbonyl, benzoxazol-4-ylaminocarbonyl benzoxazol-5-ylaminocarbonyl, benzoxazol-6-ylaminocarbonyl, benzoxazol-7-ylaminocarbonyl, 1,2-benzisoxazol-3-ylaminocarbonyl, 1,2-benzisoxazol-4-ylaminocarbonyl, 1,2-benzisoxazol-5-ylaminocarbonyl, 1,2-benzisoxazol-6-ylaminocarbonyl, 1,2-benzisoxazol-7-ylaminocarbonyl, pyrazolopyridin-3-ylaminocarbonyl, pyrazolopyridin-4-ylaminocarbonyl -ylaminocarbonyl, pyrazolopyridin-5-ylaminocarbonyl, pyrazolopyridin-6-ylaminocarbonyl, quinazolin-2-ylaminocarbonyl, quinazolin-4-ylaminocarbonyl, quinazolin-5-ylaminocarbonyl, quinazolin-6-ylaminocarbonyl, quinazolin-7-ylaminocarbonyl, quinazolin-8-ylaminocarbonyl, quinoxalin-2-ylaminocarbonyl, quinoxalin-5-ylaminocarbonyl, quinoxalin-6-ylaminocarbonyl, cinnolin-3-ylaminocarbonyl,Examples of such groups include cinnolin-4-ylaminocarbonyl, cinnolin-5-ylaminocarbonyl, cinnolin-6-ylaminocarbonyl, cinnolin-7-ylaminocarbonyl, and cinnolin-8-ylaminocarbonyl.

[0134] "R" of the present invention ４ and R ４’ may each together with the carbon atom to which they are attached form a 3- to 8-membered monocyclic carbocyclyl group, which carbocyclyl group is １ ~C ６ In the phrase "optionally substituted with one or more substituents selected from alkyl groups," the carbocyclyl group includes, but is not limited to, the following:

[0135]

[0136] "R" of the present invention ４ and Q may each, together with the carbon atom to which they are bonded, form a 5- to 12-membered carbocyclyl group, or a 5- to 12-membered heterocyclyl group having one heteroatom selected from an oxygen atom, a nitrogen atom, and a sulfur atom," unless otherwise specified, examples of the 5- to 12-membered carbocyclyl group include indan, tetralin, etc., and unless otherwise specified, examples of the 5- to 12-membered heterocyclyl group include 2,3-dihydrobenzofuran, 1,3-dihydroisobenzofuran, chroman, isochroman, 2,3-dihydro-1-benzothiophene, 1,3-dihydro-2-benzo Examples of such groups include thiophene, thiochroman, isothiochroman, indoline, isoindoline, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline, 2,3-dihydro-1-benzothiophene 1-oxide, 1,3-dihydro-2-benzothiophene 1-oxide, thiochroman 1-oxide, isothiochroman 1-oxide, 2,3-dihydro-1-benzothiophene 1,1-dioxide, 1,3-dihydro-2-benzothiophene 1,1-dioxide, thiochroman 1,1-dioxide, and isothiochroman 1,1-dioxide.

[0137] In the present invention, "one or more R ５ "may be substituted with a substituent selected from" means "one or more R ５ Two or more R ５ When substituted by ５ may be the same or different, R ５ represents a hydroxy group, a halogen atom, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Haloalkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, hydroxy C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkoxy-C １ ~C ６ Alkyl group, C １ ~C６ Alkoxy-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ８ Cycloalkoxy group, 3- to 6-membered heterocyclyl group, 3- to 6-membered heterocyclyloxy group, 3- to 6-membered heterocyclyl-C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl group, C ６ ~C １２ Aryloxy group, C ６ ~C １２ Aryl-C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl-C ２ ~C ６ Alkynyl group, 9- to 12-membered carbocyclyl group, 5- to 12-membered heteroaryl group, 5- to 12-membered heteroaryloxy group, 5- to 12-membered heteroaryl-C １ ~C ６ Alkoxy group, 5- to 12-membered heteroaryl-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxy group, C ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxycarbonyl-C １ ~C ６ Alkoxy group, C １ ~C ６Alkylsulfanyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfinyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfonyl-C １ ~C ６ Alkoxy group, C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkoxy group, hydroxy C １ ~C ６ Alkoxy group, cyano C １ ~C ６ Alkoxy group, cyano C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkoxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylcarbonyloxy group, C ３ ~C ８ cycloalkylcarbonyloxy group, C １ ~C ６ Alkyl-C ３ ~C ８ cycloalkylcarbonyloxy group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C ３ ~C ８ cycloalkylcarbonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylcarbonyl group, formyl group, carboxyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Haloalkoxycarbonyl group, C ３ ~C ８ cycloalkoxycarbonyl group, C １ ~C６ Alkyl-C ３ ~C ８ Cycloalkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ alkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylaminocarbonyl-C １ ~C ６ Alkoxy group (the amino group is R ６ a mercapto group, C １ ~C ６ Alkylsulfanyl group, C １ ~C ６ Haloalkylsulfanyl group, C ３ ~C ８ Cycloalkylsulfanyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfanyl group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Haloalkylsulfinyl group, C ３ ~C ８ Cycloalkylsulfinyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfinyl group, C１ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkylsulfonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfonyl group, amino group, C １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ６ ~C １２ Arylcarbonylamino group (the amino group is R６ a 3- to 6-membered heterocyclylcarbonylamino group (the amino group may be substituted with a substituent selected from R ６ a 5- to 12-membered heteroarylcarbonylamino group (the amino group may be substituted with a substituent selected from R ６ may be substituted with a substituent selected from ６ ~C １２ An arylaminocarbonyl group (the amino group is R ６ a 3- to 6-membered heterocyclylaminocarbonyl group (the amino group may be substituted with a substituent selected from R ６ a 5- to 12-membered heteroarylaminocarbonyl group (the amino group may be substituted with a substituent selected from R ６ may be substituted with a substituent selected from １ ~C ６ Alkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C １ ~C ６ haloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R６ may be the same or different), C ３ ~C ８ A cycloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), -C(=NR ７ ) R ８ group, or —OCH ２ C (=NR ７ ) R ８ The group is shown.

[0138] In the present invention, "one or more R ９ "may be substituted with a substituent selected from" means "one or more R ９ Two or more R ９ When substituted by ９ may be the same or different, R ９ represents a hydroxy group, a halogen atom, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ haloalkoxy group, or C ３ ~C ８ This represents a cycloalkoxy group.

[0139] In the present invention, the salt refers to a salt 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 the general formula [I], with a metal or an organic base, or with a mineral acid or an organic acid. Examples of the metal include alkali metals such as sodium or potassium, and alkaline earth metals such as magnesium or calcium. Examples of the organic base include triethylamine or diisopropylamine. Examples of the mineral acid include hydrochloric acid, hydrobromic acid, sulfuric acid, and the like. Examples of the organic acid include formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, 4-toluenesulfonic acid, trifluoromethanesulfonic acid, and the like.

[0140] Next, representative examples of compounds included in the N-oxy-pyrazole-5-carboxamide compounds of the present invention represented by general formula [I] are shown in Tables 1 to 68. 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.

[0141] The compounds encompassed by the N-oxy-pyrazole-5-carboxamide compounds of the present invention may have E- and Z-configurations depending on the type of substituent bonded to the carbon-nitrogen or carbon-carbon double bond, and the present invention encompasses mixtures containing the E- and Z-configurations in any ratio.

[0142] The compounds encompassed by the N-oxy-pyrazole-5-carboxamide compounds of the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention encompasses all optically active compounds, racemates, and diastereomers.

[0143] The compounds included in the N-oxy-pyrazole-5-carboxamide compounds of the present invention may have tautomers depending on the type of substituent, and the present invention includes mixtures containing these tautomers in any ratio. Furthermore, the naming of the compounds does not exclude any tautomers, and examples thereof include, but are not limited to, the following:

[0144] The following symbols in the tables in this specification represent the corresponding groups, for example, as follows: Me: methyl; Et: ethyl; Pr-n: n-propyl; Pr-i: isopropyl; Bu-n: n-butyl; Bu-i: isobutyl; Bus: sec-butyl; Bu-t: tert-butyl; Pen-n: n-pentyl; Pen-i: isopentyl; Pen-s: sec-pentyl; Pen-neo: neopentyl; Pen-t: tert-amyl; Hex-n: n-hexyl; CF ２ H: difluoromethyl; CF ３ : trifluoromethyl; CH ２ CF ３ : 2,2,2-trifluoroethyl; Pr-c : cyclopropyl; Pr-c(1-Me) : 1-methylcyclopropyl; Bu-c : cyclobutyl; Pen-c : cyclopentyl; Hex-c : cyclohexyl; Ac : methylcarbonyl; C(=O)OMe : methyl ester; pyridin-3-yl : pyridin-3-yl; Ph(2,4-Me ２) : 2,4-dimethylphenyl; Ph(2-F,3-F) : 2,3-difluorophenyl; Ph(4-NHC(=O)Ph) : 4-benzamidophenyl; Ph(4-NHC(=O)Ph(2-F)): 4-(2-fluorobenzamido)phenyl; Ph(4-N(Me)C(=O)Ph) : 4-(N-methylbenzamido)phenyl; pyridin-3-yl(6-Cl) : 6-chloropyridin-3-yl; Ph(4-NHC(=O)pyridin-2-yl): 4-[(pyridin-2-yl)carbonylamino]phenyl; Ph(4-N(Me)C(=O)pyridin-2-yl): 4-[(N-methyl-(pyridin-2-yl)carbonylamino)phenyl; Ph(4-NHC(=O)pyridin-3-yl): 4-[(pyridin-3-yl)carbonylamino]phenyl; Ph(4-NHC(=O)pyridin-3-yl(2-Cl)): 4-[(2-chloropyridin-3-yl)carbonylamino]phenyl; Ph(4-OCH ２ C≡CH): 4-(2-propynyloxy)phenyl; Ph(4-OCH ２ Pr-c(1-CN)): 4-(1-cyanocyclopropyl)methoxyphenyl; Ph(4-(tetrahydrofuran-3-yl)): 4-(tetrahydrofuran-3-yl)phenyl; Ph(4-O(tetrahydrofuran-3-yl)): 4-(tetrahydrofuran-3-yl)oxyphenyl; Ph(4-OCH ２(tetrahydrofuran-3-yl)): 4-(tetrahydrofuran-3-yl)methoxyphenyl; indan-5-yl: indan-5-yl; 1,3-benzodioxol-5-yl: 1,3-benzodioxol-5-yl; 2,3-dihydrobenzofuran-5-yl: 2,3-dihydrobenzofuran-5-yl; 1,4-benzodioxan-6-yl: 1,4-benzodioxan-6-yl; 2,3-dihydrobenzo[b]thiophen-5-yl: 2,3-dihydrobenzo[b]thiophen-5-yl; 2,3-dihydrobenzo[b]thiophen-5-yl 1-oxide: 2,3-dihydrobenzo[b]thiophen-5-yl 1-oxide; 2,3-dihydrobenzo[b]thiophen-5-yl 1,1-dioxide: 2,3-dihydrobenzo[b]thiophen-5-yl 1,1-dioxide;

[0145]

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[0212]

[0213] 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]" and "compound [I]" are synonymous.

[0214] <Production Method 1> Of the compounds of the present invention, the compound represented by the general formula [I] can be produced according to the following method.

[0215]

[0216] (In the formula, W １ represents a halogen atom or a trifluoroacetoxy group, and A and R １ , R ２ , R ３ , R ４ , R ４’ , and Q have the same meanings as above.)

[0217] That is, the compound represented by the general formula [I] can be produced by reacting the compound [II] with the compound [III-1] or the compound [III-2] in a suitable solvent in the presence or absence of a suitable condensing agent and a suitable additive, in the presence or absence of a suitable catalyst, and in the presence or absence of a suitable base.

[0218] The amount of the compound [III-1] or compound [III-2] used in this reaction may be appropriately selected in the range of 1.0 to 3.0 mol per 1 mol of the compound [II], and is preferably 1.0 to 2.0 mol.

[0219] Condensing agents that can be used in this reaction include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, 1H-benzylaminopropyl Examples of the condensing agent include benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, ({[(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy}-4-morpholinomethylene)dimethylammonium hexafluorophosphate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, and propylphosphonic anhydride. The amount of the condensing agent used may be appropriately selected from a range of 1.0 to 5.0 moles per mole of compound [II], and is preferably 1.0 to 3.0 moles.

[0220] The catalyst usable in this reaction may be, for example, 4-N,N-dimethylaminopyridine, etc. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 1.0 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II].

[0221] Examples of additives that can be used in this reaction include 1-hydroxybenzotriazole, N-hydroxysuccinimide, 1-hydroxy-7-azabenzotriazole, etc. The amount of the additive used may be appropriately selected from the range of 0.01 to 3.0 mol, preferably 1.0 to 1.5 mol, per mol of compound [II].

[0222] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, magnesium hydroxide, etc.; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc.; alkali metal phosphates such as tripotassium phosphate, etc.; metal hydrides such as sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; and organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-methylmorpholine, N-ethyldiisopropylamine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, 2,6-lutidine, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, etc. The amount of the base used may be appropriately selected from the range of 0.1 to 10.0 moles per mole of compound [II], and is preferably 0.1 to 5.0 moles.

[0223] 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 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; and mixtures thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.3 to 50 liters, per mole of compound [II].

[0224] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0 to 80°C.

[0225] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually from 1 minute to 96 hours.

[0226] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, to isolate compound [I]. The isolated compound [I] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0227] The starting compound [II] can be obtained by known methods, for example, the methods described in International Publication No. 2023 / 243678, etc. The starting compounds [III-1] and [III-2] are commercially available, or can be obtained by known methods, for example, the methods described in Bioorganic and Medicinal Chemistry Letters, 2003, 13, 3155-3159, Organic Letters, 2019, 21, 1868-1871, etc.

[0228] <Production Method 2> Of the compounds of the present invention, the compound represented by the general formula [VI] can be produced according to the following method.

[0229]

[0230] (In the formula, A, R ２ , and W １ has the same meaning as above, and R １０ is C １ ~C ６ represents an alkyl group.)

[0231] That is, the compound represented by the general formula [VI] can be produced by reacting compound [IV] with compound [V-1] or compound [V-2] in an appropriate solvent in the presence or absence of an appropriate acid and in the presence or absence of an appropriate base. The amount of compound [V-1] or compound [V-2] used in this reaction may be appropriately selected usually in the range of 1.0 to 5.0 mol per 1 mol of [IV], and is preferably 1.0 to 2.5 mol.

[0232] The acid that can be used in this reaction includes, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc.; organic acids such as acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc. The amount of the acid used may be appropriately selected from the range of 0.1 to 50 mol, preferably 0.1 to 5.0 mol, per 1 mol of compound [IV].

[0233] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, magnesium hydroxide, etc.; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc.; alkali metal phosphates such as tripotassium phosphate, etc.; metal hydrides such as sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; and organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-methylmorpholine, N-ethyldiisopropylamine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, 2,6-lutidine, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, etc. The amount of the base used may be appropriately selected from the range of 0.1 to 5.0 moles per mole of compound [IV], and is preferably 0.1 to 5.0 moles.

[0234] 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 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; and mixtures thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters, per mole of compound [IV].

[0235] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 120°C.

[0236] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually from 1 minute to 48 hours.

[0237] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, to isolate compound [VI]. The isolated compound [VI] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0238] The starting compound [IV] can be obtained according to known methods, such as those described in Bioorganic and Medicinal Chemistry Letters, 2015, 25, 4481-4486 and WO 2023 / 243678. The starting compounds [V-1] and [V-2] are commercially available or can be obtained according to known methods, such as those described in Journal of Medicinal Chemistry, 2019, 62, 3135-3146.

[0239] <Production Method 3> Among the compounds of the present invention, the compound represented by the general formula [VI-2] can be produced according to the following method.

[0240] (In the formula, A, R １ , or R １０ has the same meaning as above, and R １１ is C １ ~C ６ represents an alkyl group; W ２ represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, or the like; L １ is C １ ~C ６ Alkanediyl group, or C ３ ~C ８ cycloalkanediyl group, etc., L ２ is C １ ~C ６ represents an alkanediyl group or bond.

[0241] That is, the compound represented by the general formula [VI-2] can be produced by reacting compound [VI-1] with compound [VII] in an appropriate solvent in the presence or absence of an appropriate base. The amount of compound [VII] used in this reaction may be appropriately selected from the range of 1.0 to 3.0 moles, preferably 1.0 to 1.5 moles, per mole of compound [VI-1].

[0242] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, magnesium hydroxide, etc.; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc.; alkali metal phosphates such as tripotassium phosphate, etc.; metal hydrides such as sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; and organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-methylmorpholine, N-ethyldiisopropylamine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, 2,6-lutidine, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, etc. The amount of the base used may be appropriately selected from the range of 0.1 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol of the compound [VI-1].

[0243] 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 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; and mixtures thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.3 to 50 liters, per mole of compound [VI-1].

[0244] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0 to 80°C.

[0245] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually from 1 minute to 48 hours.

[0246] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [VI-2]. The isolated compound [VI-2] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0247] The starting compound [VI-1] is commercially available or can be obtained by a known method, such as that described in WO 2002 / 085860.

[0248] <Production Method 4> Of the compounds of the present invention, the compound represented by the general formula [IX] can be produced according to the following method.

[0249] (In the formula, A, R １ , or R ２ has the same meaning as above, and R １２ represents a hydrogen atom or a hydroxy group.)

[0250] That is, the compound represented by the general formula [IX] can be produced by reacting the compound represented by the general formula [VIII] with a suitable oxidizing agent in the presence or absence of a suitable catalyst and in the presence or absence of a suitable base in a suitable solvent.

[0251] Examples of the oxidizing agent that can be used in this reaction include potassium peroxodisulfate, sodium peroxodisulfate, etc. The amount of the oxidizing agent used may be appropriately selected from the range of 0.5 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol of compound [VIII].

[0252] Examples of the catalyst that can be used in this reaction include copper(II) sulfate pentahydrate, vanadium pentoxide, titanium oxide, etc. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10.0 mol, preferably 0.1 to 0.5 mol, per 1 mol of compound [VIII].

[0253] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, magnesium hydroxide, etc.; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc.; alkali metal phosphates such as tripotassium phosphate, etc.; metal hydrides such as sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; and organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-methylmorpholine, N-ethyldiisopropylamine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, 2,6-lutidine, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, etc. The amount of the base used may be appropriately selected from the range of 0.1 to 10.0 mol, preferably 0.1 to 5.0 mol, per 1 mol of compound [VIII].

[0254] 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; 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 compound [VIII].

[0255] 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.

[0256] 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.

[0257] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [IX]. The isolated compound [IX] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0258] The starting compound [VIII] is commercially available or can be obtained according to known methods, such as those described in WO 2002 / 085860, WO 2008 / 135824, and WO 2014 / 076237.

[0259] <Production Method 5> Of the compounds of the present invention, the compound represented by the general formula [II] can be produced according to the following method.

[0260] (In the formula, A, R １ , or R ２ has the same meaning as above.)

[0261] That is, the compound represented by the general formula [II] can be produced by reacting the compound represented by the general formula [IX] with a suitable oxidizing agent in a suitable solvent in the presence or absence of a suitable additive.

[0262] Examples of the oxidizing agent that can be used in this reaction include inorganic peroxides such as hydrogen peroxide, potassium permanganate, and Oxone (registered trademark) (a product of E.I. du Pont containing potassium hydrogen peroxosulfate); and halogen salts such as sodium chlorite. The amount of the oxidizing agent used may be appropriately selected from the range of 0.5 to 5.0 mols, preferably 1.0 to 4.0 mols, per mol of compound [IX].

[0263] Examples of additives that can be used in this reaction include 2-methyl-2-butene, sodium dihydrogen phosphate, etc. The amount of the additive used may be appropriately selected from the range of 0.001 to 20.0 mol, preferably 0.1 to 10.0 mol, per 1 mol of compound [IX].

[0264] 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; 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 compound [IX].

[0265] 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.

[0266] 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.

[0267] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [II]. The isolated compound [II] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0268] The agricultural and horticultural plant disease control agent of the present invention is characterized by containing, as an active ingredient, the N-oxy-pyrazole-5-carboxamide compound represented by the general formula [I] of the present invention or a salt thereof.

[0269] The agricultural and horticultural plant disease control agent of the present invention is characterized by containing, as an active ingredient, the N-oxy-pyrazole-5-carboxamide compound represented by the general formula [I] of the present invention or a salt thereof. The N-oxy-pyrazole-5-carboxamide compound represented by the general formula [I] or a salt thereof is not particularly limited, but is preferably A-0022, A-0023, A-0024, A-0034, A-0035, A-0036, A-0045, A-0046, A-0047, A-0058, A-0061, A-0063, A-0064, A-0066, A-0077, A-0079, A-0080, A-0100, A-0101, A-0107, A-0120, A-0121, A-0129, A-0144, A-014 6, A-0147, A-0151, A-0153, A-0155, A-0156, A-0161, A-0174, A-0192, A-0194, A-0195, A-0197, A-0200, A-0201, A-0211, A-0212, A-0214, A-0224, A-0228, A-0231, A-0232, A-0249, A-0251, A-0268, A-0269, A-0272, A-0273, A-0274, A-0275, A-0277, A-0279, A-0280, A-0283, A-0 285, A-0287, A-0297, A-0298, A-0299, A-0301, A-0304, A-0314, A-0325, A-0348, A-0367, A-0368, A-0372, A-0374, A-0379, A-0384, A-038 5, A-0404, A-0425, A-0526, A-0527, A-0532, A-0533, A-0536, A-0543, A-0544, A-0563, A-0566, A-0567, A-0570, A-0572, A-0573, A-0575, A -0576, A-0578, A-0581, A-0582, A-0583, A-0584, A-0585, A-0587, A-0600, A-0603, A-0605, A-0606, A-0611, A-0612, A-0622, A-0623, A-08 03, A-0804, A-0805, A-0808, A-0809, A-0812, A-0823, A-0824, A-0825, A-0826, A-0828, A-0831, A-0835, A-0837, A-0838, A-0840, A-0845,- - 6. 08、A-1509、A-1511、A-1512、A-1526、A-1534、A-1575、A-1718、A-1731、A-7 35, A-1877, A-1880, A-2607, A-2744, A-2755, A-2756, A-2757, A-2758, A-2759, A-2760, B-0006, more preferably A-0022, A-0023, A-0024, A-0034, A-0035, A-0036, A-0045, A-0046, A-0047, A-0061, A-0063, A-0064, A-0066, A-0077, A-0079, A-0080, A-0100, A-0101, A-0107, A-0120, A-0121, A-0129, A-014 4. 92、A-0194、A-0195、A-0197、A-0200、A-0201、A-0211、A-0212、A-0212 224、A-0228、A-0231、A-0232、A-0249、A-0251、A-0268、A-0269、A-02222 0273、A-0274、A-0275、A-0277、A-0279、A-0280、A-0285、A-0202 A -0372、A-0374、A-0379、A-0384、A-0385、A-0404、A-0425、A-05252 -0532、A-0533、A-0536、A-5543、A-0544、A-0563、A-0566、A-05522 A-0572、A-0573、A-0575、A-0576、A-0578、A-0581、A-0502、A-0502、A-0502、A-0585, A-0587, A-0600, A-0603, A-0605, A-0606, A-0611, A-0612, A-0622, A -0623, A-0803, A-0804, A-0805, A-0808, A-0809, A-0812, A-0823, A-0824, A- 0825, A-0826, A-0828, A-0831, A-0835, A-0837, A-0838, A-0840, A-0845, A-0 852, A-0860, A-0861, A-0865, A-0869, A-0875, A-0881, A-0882, A-0884, A-089 2, A-0898, A-0924, A-1027, A-1121, A-1124, A-1140, A-1142, A-1166, A-1207 , A-1210, A-1323, A-1324, A-1325, A-1327, A-1328, A-1507, A-1508, A-1509, A-1511, A-1512, A-1526, A-1534, A-1575, A-1718, A-1731, A-1735, A-1877, A -1880, A-2744, A-2755, A-2756, A-2757, A-2758, A-2759, A-2760, B-0006. ,

[0270] The agricultural and horticultural plant disease control agent of the present invention may contain, as necessary, an additive component (carrier) that is usually used in agrochemical formulations.

[0271] Examples of the additive components include carriers such as solid carriers 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.

[0272] The additive components will be described below.

[0273] 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.

[0274] 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 ether; 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, C ９ -C １０Examples 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 vegetable oils; and water.

[0275] 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, resin salts, 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 include betaine-type surfactants such as dialkyldiaminoethyl betaine and alkyldimethylbenzyl betaine, and amino acid-type surfactants such as dialkylaminoethyl glycine and alkyldimethylbenzyl glycine;

[0276] 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., cephalin, lecithin, etc.).

[0277] 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.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0282] Examples of the anti-caking agent include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, and petroleum resin.

[0283] 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.

[0284] 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.

[0285] Examples of preservatives include potassium sorbate and 1,2-benzothiazol-3(2H)-one.

[0286] Examples of plant fragments include sawdust, coconut husks, corn cobs, tobacco stalks, etc.

[0287] 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, on a mass basis, from usually 5 to 95%, preferably 20 to 90%, for carriers such as solid carriers or liquid carriers; from usually 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.

[0288] 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.

[0289] 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 before use. The application of various formulations containing the compound 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, powder coating, covering, etc.), seed treatment (e.g., smearing, powder coating treatment, etc.), immersion, poison bait, fumigation application, etc. Furthermore, it is also possible to mix the active ingredient with feed and feed it to livestock to control the occurrence and growth of pests, particularly harmful insects, in their excrement.

[0290] The method for controlling agricultural and horticultural plant diseases of the present invention can be carried out by using an active ingredient amount of the N-oxy-pyrazole-5-carboxamide compound or a salt thereof of the present invention in the above-mentioned application method.

[0291] 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 an emulsifiable concentrate, etc., it is appropriately selected from the range of 5 to 90%, preferably 10 to 80%, in the case of an emulsion, etc., it is appropriately selected from the range of 1 to 50%, preferably 5 to 30%, in the case of an oil solution, 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%.

[0292] These formulations are diluted to an appropriate concentration and then sprayed, or applied directly.

[0293] When the agricultural and horticultural plant disease control agent of the present invention is diluted with a diluent, it is generally applied at an active ingredient concentration of 0.1 to 5000 ppm. 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.

[0294] 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.

[0295] Next, examples of known fungicides (fungicidal active ingredients) or disease control compounds that may be mixed or used in combination are given below.

[0296] Fungicidal active ingredient or disease control compound: Agrobacterium radiobacter radiobacter), azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminopyrifen, ametoctradine, aldimorph, isotianil, isopyrazam, isofetamide, isofletamide, isoflucipram, isoprothiolane, ibuprofen, 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 oils, oxadixyl, oxazinylazole, oxathiapiprolin, oxycarboxin,Oxyquinoline copper (oxine-copper), oxytetracycline (oxytetracycline), oxpoconazole-fumarate (oxpoconazole-fumarate), oxolinic acid (oxolinic acid), copper octanoate (copper dioctanoate), octhilinone, ofurace, orysastrobin, o-phenylphenol, kasugamycin, captafol, galquin, carpropamid, carbendazim, carboxin, carbone, Candida oleophila, Candida cytoana saitoana), quinaminoprole, quinoxyfen, quinofumelin, chinomethionate, captan, quinconazole, quintozene, guazatine, cufraneb, coumethoxystrobin, coumoxystrobin, gliocladium catenulatum, Cryptococcus albidus albidus), kresoxim-methyl (kresoxim-methyl), clozylacon (clozylacon), Clonostachys rosea (Clonostachys rosea), chlorzolinate (chlorinconazide), chlorothalonil (chlorothalonil), chloroneb (chloroneb), Chaetomium cupreum (Chaetomium cupreum), Coniothyrium minitans (Coniothyrium minitans), cyazofamid (cyazofamid),Diethofencarb, diclocymet, dichlofluanid, dichlobentiazox, diclomezine, dicloran, dichlorophen, dithianon, diniconazole, diniconazole-M, zineb, zinoca dinocap, dipimethitrone, diphenylamine, difenoconazole, cyflufenamid, diflumetrim, cyproconazole, cyprodinil, simeconazole, dimethylimol, dimethyl disulfide disulfide), dimethomorph, cymoxanil, dimoxystrobin, Pseudozyma flocculosa, Pseudomonas aureofaciens, Pseudomonas chlororaphis, Pseudomonas syringae, Pseudomonas fluorescens, Pseudomonas rhodesiae rhodesiae), ziram, silthiofam, attenuated strain of zucchini yellow mosaic virus, streptomycin, Streptomyces griseoviridis, Streptomyces lygicus, spiroxamine,Sedaxane, seboxylamine, zoxamide, solatenol, dazomet, Talaromyces flavus flavus), tiadinil, thiabendazole, thiuram, thiophanate, thiophanate-methyl, thifluzamide, thiram, tecnazene, tecloftalam, tetraconazole, debacarb (d ebacarb), tebuconazole, tebufloquine, terbinafine, dodine, dodemorph, triadimenol, triadimefon, triazoxide, trichlamide, triclopyricarb, Trichoderma Trichoderma asperellum, Trichoderma atroviride, Trichoderma gamsii, Trichoderma stromaticum, Trichoderma paecilomyces, Trichoderma harzianum, Trichoderma viride, Trichoderma virens, Trichoderma polysporum polysporum), Trichoderma harzianum rifai, Trichoderma lignorum, tricyclazole, triticonazole,Tridemorph, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolnifanide, tolprocarb, nabam, natamycin, naftifine, nitrapyrin, nitrothal-isopropyl, nuarimol, copper nonylphenolsulfonate sulphonate), Paenibacillus polymyxa, Burkholderia cepacia, Burkholderia rinogensis, Bacillus amyloliquefaciens, Bacillus simplex, Bacillus subtilis, Bacillus pumilus, Bacillus mycoides, Bacillus Bacillus licheniformis, harpin protein, Variovorax paradoxus, validamycin, valifenalate, Pantoea agglomerans, picarbutrazox, bixafen, picoxystrobin, Pythium oligandrum oligandrum), pydiflumetofen, bitertanol, binapacryl, hinokitiol,Non-pathogenic Erwinia carotovora, non-pathogenic Rhizobium vitis, biphenyl, bifemetstrobin, piperalin, hymexazol, pyraoxystrobin, pyraclostrobin aclostrobin), pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriophenone, pyrisoxazole, pyridaclomethyl, pyrimetostrobin 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, fthalide, fusarium Oxysporum (Fusarium oxysporum), bupirimate (bupirimate), fuberidazole (fuberidazole), blasticidin-S (blasticidin-S), furametpyr (furametpyr),Furalaxyl, furanocarboxylic acid, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluopicolide, fluopimomide omide), fluopyram, fluorimide, fluxapyroxad, fluquinometoate, fluquinconazole, fluconazole, fluconazole-cis -cis), fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, flubeneteram, flumethylsulforim, flumetover, flumorph, Phlebiopsis gigantea gigantea), proquinazid (proquinazid), prochloraz (prochloraz), procymidone (procymidone), prothiocarb (prothiocarb), prothioconazole (prothioconazole), bronopol (bronopol), propamocarb hydrochloride (propamocarb-hydrochloride), propiconazole (propiconazole), propineb (propineb), probenazole (probenazole), bromuconazole (bromuconazole), flometoquin (flometoquin), florylpicoxamid (florylpicoxamid),Hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, penconazole, pencycuron, benzovindiflupyr, benthiazole ole), benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, fosetyl (including salts of aluminum, calcium, sodium, etc.), polyoxin, polycarbamate, Bordeaux mixture, mancopper, mancozeb, mandipropamid, mandestrobin, maneb, myclobutanil, mineral oil oils), mildiomycin, methasulfocarb, metam, metalaxyl, metalaxyl-M, metharylpicoxamide, metiram, methyltetraprole, metconazole, metominostrobi metominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, meptyldinocap, mepronil, iodocarb, laminarin, ledprona, phosphorous acid and salts, basic copper chloride,Silver, copper acetate (copper(II) sulfate), cuprous oxide, copper hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, copper sulfate sulfate), UK-2A (code number), dodecylbenzenesulfonic acid 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 (chemical name, C AS Registration Number: 2435594-93-5) (WO 2020 / 109391 A1), 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-difluoroethyl]-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide (chemical name, CAS registration number: 2435603-06-6) (WO 2020 / 1093 91), 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]-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide )ethyl]-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide (6-chloro-N-[2-(2,4-dimethylphenyl)ethyl]-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide) (chemical name, CAS registration number: 2435603-15-7) (WO 2020 / 109391 ), racemic-3-[6-chloro-5-methyl-3-[3-(trifluoromethyl)phenoxy]pyridazine-4-carboxamide ]pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (rac-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).

[0297] Next, examples of known insecticides (insecticidal active ingredients), acaricides (acaricidal active ingredients), nematicides (nematicidal active ingredients), and synergist compounds (synergistic active ingredients) that may be mixed or used in combination are shown below.

[0298] Insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, synergistic active ingredients: acrinathrin, azadirachtin, azamethiphos, acinonapyr, azinphos-ethyl, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, azocyclotin, Abamectin, afidopyropene, afoxolaner, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, allethrin [including d-cis-trans-isomer and d-trans-isomer], isazophos, isamidophos ), isocarbophos, isoxathion, isocycloceram, isofenphos-methyl, isoflualanum, isoprocarb, epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin n), imicyafos, imidacloprid, imiprothrin, indazapyroxameth, 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 virus), cadusafos, kappa-tefluthrin, kappa-bifenthrin, karanjin, galquin, cartap, granulosis virus, carbaryl, carbosulfan, carbofuran, gamma-BHC, xylylcarb, quinalphos, kinoprene, chinomethionate, acute paralysis virus (Enterobacter pylori virus), virus), coumaphos, cryolite, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyphos, chlordane rdane), chloropicrin, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos,Chloroprallethrin, Entomovoxi virus, Irido virus, Cyazypyr, Cyanophos, Diafenthiuron, Diamidafos, Cyantraniliprole, Cyetopyrafen, Dienochlor, Cyenopyrafen, Dioxabenzophos, Diofenolan, Sigma virus virus), cyclaniliprole, cycloxaprid, dicrotophos, diclofenthion, cyclobutrifluram, cycloprothrin, dichlorvos s), dichloromezotiaz, dicofol, dicyclanil, disulfoton, dinotefuran, dinobuton, cyhalodiamide, cyhalothrin [gamma-isomer, l ambda-isomer], cyphenothrin [including (1R)-trans-isomer], cyfluthrin [including beta-isomer], diflubenzuron, cyflumetofen, diflovidazin, cyprofanilide de), cyhexatin, cypermethrin [including alpha-, beta-, theta-, and zeta-forms], cibenzoxasulfyl, dimpropylidaz, 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 ifen), sulfofuron-sodium salt, sulfiflumin, sulfuramide, sulfoxaflor, sulfoxamyl, sulfotep, diazinon, thiacloprid id), thiapyrachlor, thiamethoxam, thioxazafen, thiodicarb, thiocyclam, thiosultap, thionazine, thiofanox, thiometon eton), thiolantraniliprole, cyclopyrazoflor, tigolaner, tetrachlorantraniliprole, tetrachlorvinphos, tetradifon,Tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton S methyl on-S-methyl), temephos, deltamethrin, terbufos, tralomethrin, transfluthrin, triazamate, triazophos, trioxyflanilide, trichlorfon, Trichoderma Asperellum, Trichoderma paecilomyces, Trichoderma harzianum, triflumuron, trifluenfuronate, triflumezopyrim, trimethacarb, tolfenpyrad, naled, nicotine, nicofluprole, nitenpyram, nemadectin, densovirus virus), novaluron (novaluron), noviflumuron (noviflumuron), paecilomyces lilacinus (paecilomyces lilacinus), Burkholderia cepacia (Barkholderia cepacia), Verticillium lecanii (Verticillium lecanii), hydroprene (hydroprene), Pasteuria nishizawai (Pasteuria nishizawae), Pasteuria penetrans (Pasteuria penetrans),Insecticidal toxins produced by Bacillus amyloliquefaciens, Bacillus firmus, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Bacillus thuringiensis subsp. Israelensis, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis, Bacillus popilliae, Bacillus licheniformis licheniformis, badescana, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bioallethrin, bioallethrin S-cyclopentenyl S-cyclopentenyl), pioxaniliprole, bioresmethrin, bis-(2-chloro-1-methylethyl) ether (DCIP), bistrifluron, bisulfulfen, hydramethylnon, bifenazate, bifenthrin, piflubumid, piperflanilide,Piperonyl butoxide, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins thrine), famflu, fipronil, fenazaquin, fenamiphos, fenitrothion, fenoxycarb, fenothiocarb, fenothrin [including the (1R)-trans-isomer], fenobucarb, fenthion, phenthoate, fenvalerate, fenpyroximate, fenbutanthin oxide oxide), fenpropathrin, phenmezoditiaz, fonofos, sulfuryl fluoride fluoride), butocarboxim, butoxycarboxim, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazuron, fluensulfone, fluopyram, sodium fluoroacetate,Fluxametamide, fluclodiniliprole, flucycloxuron, flucythrinate, fluthrin, fluvalinate [including tau-isomer], flupyradifurone, flupyrazofos, flupirimi Flupyrimin, flupyroxystrobin, flufiprole, flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flupentiophenox ofenox, flumetnicum, flumethrin, fluralaner, flurimfen, prothiofos, protrifenbut, flonicamid, propaphos, propargite, prohydrojasmone asmon), profenofos, broflanilide, profluthrin, propetamphos, propoxur, flometoquin, bromopropylate, hexathiazox, hexaflumuron, pekiromyces Pacilimyces tenuipes, Paecilomyces fumosoroceus, Paecilomyces lilacinus, heptafluthrin, heptenophos, permethrin,Benclothiaz, benzpyrimoxan, bensultap, benzoximate, bendiocarb, benfuracarb, bentioflumin, Pochonia chlamydosporia, Beauveria tenella, Beauveria bassiana, Beauveria brongniartii brongniaartii), phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosmet, polynactins, formetanate, phorate, machine oil oil), malathion, mivorilaner, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, metam, metham, methiocarb, methidathion, methyl isothiocyanate, methyl bromide bromide), methoxychlor (methoxychlor), methoxyfenozide (methoxyfenozide), methotrin (methothrin), metofluthrin (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), mevinphos (mevinphos), meperfluthrin (meperfluthrin), modoflaner (modoflaner), monosporium phymatophagum (Monacrosporium phymatophagum),Monocrotophos, momfluorothrin, Trichoderma harzianum, litlure-A, litlure-B, aluminum phosphide, zinc phosphide, hydrogen phosphide, lufenuron, rescale, resmethrin, lepimectin, rotenone, cytoplasmic polyhedrosis virus occlusion bodies virus), fenbutatin oxide, calcium nitrogen cyanide), 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)-13-icosen-10-one, 14-methyl-1-octadecene, AKD-1193 (code number), BCS-AA10147 (code number), CL900167 (code number), O,O-diethyl-O-[4-(dimethylsulfamoyl)phenyl]-phosphorothionate (DSP),O-ethyl-O-4-(nitrophenyl)phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosen-10-one, ZXI8901 (code number), F4260 (code number).

[0299] 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.

[0300] Herbicide compounds or herbicidal active ingredients: ioxynil (including lithium salt, sodium salt, salt with octanoic acid, etc.), aclonifen, acrolein, azafenidin, acifluorfen (including salt with sodium, etc.), azimsulfuron, asulam, acetochlor, acetochlor Atrazine, Anilofos, Amicarbazone, Amidosulfuron, Amitrole, Aminocyclopyrachlor, Aminopyralid, Amiprofos-methyl, Ametryn, Arausia Mosaic Virus, Alachlor, Alternaria destolens destruens), alloxydim (including salts with sodium etc.), ancymidol, icafolin-methyl, isouron, isoxachlortole, isoxafenacil, isoxaflutole, isoxaben, isodecyl alcohol ethoxylate, isopropyl alcohol Turon (isoproturon), iptriazopyride (iptriazopyrid), ipfencarbazone (ipfencarbazone), imazaquin (imazaquin), imazapic (imazapic) (including salts with amines etc.), imazapyr (imazapyr) (including salts with isopropylamine etc.), imazamethabenz (imazamethabenz), imazamethabenz-methyl (imazamethabenz-methyl), imazamox (imazamox), imazethapyr (imazethapyr),Imazosulfuron, indaziflam, indanofan, indolauxipyr-cyanomethyl, eglinazine-ethyl, esprocarb, ethametsulfuron-methyl, ethalfluralin, ethidimuron, ethoxysulfuron, ethoxyfen thoxyfen, ethoxyfen-ethyl, ethofumesate, etobenzanide, epirifenacil, endothal disodium salt, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxyfluorfen, oryzalin, and ovuda Pepper virus (Obuda Pepper Virus), orthosulfamuron, orbencarb, oleic acid, cafenstrole, caprylic acid, capric acid acid), carfentrazone-ethyl, carbutilate, carbetamide, quizalofop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, Xanthomonas campestris, quinoclamine, quinclorac, quinmerac,Citric acid, cumyluron, clacyfos, glyphosate (including salts such as sodium, potassium, amine, propylamine, isopropylamine, ammonium, isopropylammonium, guanidine, monoethanolamine, choline, BAPMA (N,N-bis-(3-aminopropyl)methylamine), dimethylamine, or trimesium), glufosinate (amine or sodium salts), ammonium salts), glufosinate-P, glufosinate-P-sodium salt, clethodim, clodinafop, clodinafop-propargyl, clopyralid (including monoethanolamine salts), clomazone, clomethoxyfen hoxyfen), clomeprop, chloransulam-methyl, chloramben, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal-dimethyl, chlorthiamid rthiamid), chlorphthalim, chlorflurenol-methyl, chlorpropham, chlorbromuron, chloroxuron, chlorotoluron, ketospiradox (including salts such as sodium, calcium or ammonia), Colletotrichum orbiculare, Colletotrichum gloeosporioides,Colletotrichum truncatum, Chondrostercum purpurea purpureum), saflufenacil, sarmentine, cyanazine, cyanamide, diuron, diethyl-ethyl, dioxopyritrione, dicamba (including amines, diethylamine, isopropylamine, diglycolamine, dimethylammonium, diolamine, isopropylammonium, olamine, potassium, trolamine, BAPMA (N,N-bis-(3-aminopropyl)methylamine), choline, salts such as sodium or lithium, or esters such as methyl esters), cycloate, cycloxydim ), diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlobenil, diclofop, diclofop-P-methyl, diclofop-methyl, dichlorprop, dichlorprop-P (including salts such as dimethylammonium, potassium, sodium, choline, or esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester), diquat, diquat dibromide dibromide), dithiopyr, siduron, dinitramine, cinidon-ethyl, cinosulfuron, dinoseb (including salts of acetic acid, ammonium, diolamine, sodium, trolamine, etc.), dinoterb, cyhalofop,Cyhalofop-butyl, cypyrafluone, diphenamide, difenzoquat, diflufenican, diflufenzopyr, simazine, dimesulfazet , dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, simetryn, dimepiperate, dimepyrolimet, dimefuron, pseudomonas Pseudomonas fluorescens, cinflubrolin, cinmethylin, swep, Sclerotinia minor, sulcotrione, sulfentrazone, sulfosate, sulfosulfuron, sulfometuron-methyl, sethoxydim, terbacil, daimuron, thaxtomin A, tobacco mild green mosaic Tobamovirus (Tobacco Mild Green Mosaic Tobamovirus), tobacco rattle virus, dalapon, thiazopyr, thiafenacil, thiencarbazone (including sodium salt, methyl ester, etc.), thiocarbazil, thiobencarb, thidiazimin, thidiazuron, thifensulfuron,Thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, thenylchlor, tebutam, tebuthiuron, tepraloxydim, tefuryltrione, terbuthylazine, terbutryn terbutryn, terbumeton, tembotrione, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, triallate, trietazine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tritosulfuron, tripyrsulfone (tripyrasulfone), trifludimoxazin, triflusulfuron-methyl, trifluralin, trifloxysulfuron (including salts with sodium and the like), tribenuron-methyl, tolpyralate, naptalam (including salts with sodium and the like), naproanilide, napropamide, naproxen-M, nicosulfuron, lactic acid acid), neburon, norflurazon, Burkholderia rinogensis, vernolate,Paraquat, paraquat dichloride, haloxifen, haloxifen benzyl, haloxifen methyl, haloxyfop, haloxyfop-P, haloxyfop-ethotyl, haloxyfop-P-methyl, halosafen, halosulfuron methyl halosulfuron-methyl), bixlozone, picloram (including salts with dichloroammonium, trolamine, etc.), picolinafen, bicyclopyrone, bispyribac-sodium, pinoxaden, bipyrazone, bifenox, piperophos, pyrazone, Clonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron-ethyl, pyrazolinate, bilanafos, pyraflufen, pyraflufen-ethyl, pyraquinate, pyridafol, pyrithiobac- Sodium salt (pyrithiobac-sodium), pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyriminobac-methyl, pyroxasulfone, pyroxsulam,Phytopsora palmivora, fenisopham, fenuron, fenoxasulfone, fenoxaprop (including methyl, ethyl, and isopropyl esters), fenoxaprop-P (including methyl, ethyl, and isopropyl esters), feproxydim, fenquinotrione, fenthiaprop-ethyl, fentrazamide, fenpyrazone, phenmedipham, and foma 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-P, fluazifop-P-butyl, fluazolate, fluometuron, fluoroglycofen-ethyl,Flucarbazone-sodium, fluchloraminopyr (including tetrahydrofurfuryl ester), fluchloralin, flucetosulfuron, flusulfinam, flucetosulfuron, fluthiacet-methyl, flupyrsulfuron-methyl hydroxybenzoates (including sodium, calcium or ammonia salts), flufenacet, flufenazopyr, flufenoximacil, flufenpyr-ethyl, flupropanate (including sodium salts), flupoxame, flumioxazin, flumiclorac-pentyl, flumetsulam ( 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, prodiamine, prochlorosulfone (prochlorosulfone), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), propaquizafop (propaquizafop), propachlor (propachlor), propazine (propazine), propanil (propanil), propyzamide (propyzamide), propisochlor (propisochlor), propyrisulfuron (propyrisulfuron), propham (propham), profluazole (profluazol),Prohexadione calcium salt, propoxycarbazone, propoxycarbazone sodium salt, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil (including esters of butyric acid, octanoic acid, heptanoic acid, etc.), bromophenone, Bromofenoxim, bromobutide, florasulam, florpyrauxifen, florpyrauxifen-benzyl, hexazinone, petoxamid, benazolin (including salts such as dimethylammonium or potassium), benazolin-ethyl, penoxsulam, pepino Mosaic virus (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, 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-po tassium), mesosulfuron (including esters such as methyl), mesotrione, metazachlor, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam (including salts such as sodium), disodium methanarsonate (DSMA), methiozoline thiozolin, methyldymuron, metoxuron, metosulam, metsulfuron-methyl, metobromuron, metproxybicyclon, metobenzuron, metolachlor, metribuzin, mepiquat chloride chloride), mefenacet, monosulfuron (including methyl, ethyl, isopropyl esters), monolinuron, molinate, iodosulfuron, iodosulfuron methyl sodium salt (iodosulfuron-methyl-sodium), iofensulfuron, iofensulfuron-sodium salt, lactofen, lancotrione, linuron,Riminoxafen, 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) (amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, diol, ammonium, dodecylammonium, heptylammonium, tetradecylammonium, triethylammonium, tris(2-hydroxypropyl)ammonium, tetradecylamine, choline, sodium or lithium salts, or 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 esters such as tefuryl esters), 2,4-dichlorophenoxybutyric acid (2,4-DB) (including salts of amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, choline, sodium or lithium, or esters such as isoctyl esters), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (including salts of sodium, dimethylammonium, choline, or esters such as 2-ethylhexyl ester, isoctyl ester, ethyl ester, or the like), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including sodium salt, ethyl ester, or the like), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB) (including salts of amines, diethylamine, triethanolamine, isopropylamine, dimethylammonium, choline, sodium or lithium, or esters such as isoctyl esters), 4,6-dinitro-O-cresol (DNOC) (including salts of amines, sodium, or the like),N4-(2,6-difluorophenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine (N4-(2,6-difluorophenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine) (chemical name, CAS registration number: 1606999-43-2) (WO 2014 / 064094, WO 2015 / 162164), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazoline 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (chemical name, CAS registration 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 (6-(1-fluorocyclopentyl)-N4-(2,3,5,6-tet 6-(1-fluoro-1-methylethyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine (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 (chemical name, CAS registration number: 1820807-75-7) (WO 2015 / 162164), 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 (MCPA-thioethyl), SYP-298 (code number), SYP-300 (code number), S-ethyldipropylthiocarbamate (EPTC), S-metolachlor, S-9750 (code number), MSMA (MSMA), HW-02 (code number),

[0301] Plant growth regulator compounds: 1-naphthylacetamide, 1-methylcyclopropene, 1,3-diphenylurea, 2,3,5-triiodobenzoic 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-phenylquinazoline-2-yl)- 3-[(6-chloro-4-phenylquinazoline-2-yl)amino]propane-1-ol (3-[(6-chloro-4-phenylquinazoline-2-yl)amino]propane-1-ol), 4-oxo-4-(2-phenylethyl)aminobutyric acid (chemical name, CAS registration number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), 5-aminolevulinic acid hydrochloride (5-aminolevulinic acid hydrochloride), methyl 5-(trifluoromethyl)benzo[b]thiophen-2-carboxylate, AVG (aminoethoxyvinylglycine), n-decyl alcohol (n-decanol), anisiflupurin, aviglycine, ancymidol, abscisic acid, isoprothiolane, inabenfide, indole acetic acid, indole butyric acid butyric acid), uniconazole, uniconazole-P, Ecolyst, ethychlozate, ethephon, epicholeon, calcium chloride,Choline chloride, oxine sulfate, kinetin, calcium peroxide, carbone, calcium formate, cloxyfonac, cloxyfonac potassium salt, cloprop, chlormequat, chlormequat chloride, chlorpropham, choline, cytokinins, oxidized glutathione glutathione), cyanamide, sodium cyanate, cyclanilide, dichlorprop (including salts of dimethylammonium, potassium, sodium, choline, etc., or esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), dichlorprop-P (including salts of sodium, potassium, dimethylammonium, etc., or 2-ethylhexyl ester), diquat, diquat dibromide, dikegulac, gibberellic acid, gibberellin A4 A4), gibberellin A7, dimethipin, sintofen, jasmone, cis-jasmone, jasmonic acid, methyl jasmonate, streptomycin, calcium sulfur, daminozide, calcium carbonate, thidiazuron, decan-1-ol,Triacontanol, triapenthenol, trinexapac-ethyl, tribufos, paclobutrazol, paraffin, bispyribac-sodium, hymexazol, butralin, fluthiacet-methyl, pyraflufen-ethyl, flumetralin , flurprimidol, flurenol, pronitridine, prohydrojasmon, prohexadione-calcium salt, heptamaloxyloglucan, 6-benzylaminopurine, pendimethalin, forchlorfenuron, formononetin, maleic hydrazide hydrazide), mepiquat chloride, mefluidide, lipochitooligosaccharides (e.g., lipochitooligosaccharides SP104), calcium sulfate.

[0302] Next, examples of known safening compounds that may be used in admixture or combination are given below.

[0303] Safeners: Isoxadifen, Isoxadifen-ethyl, Oxabetrinil, Octane-1,8-diamine, Cloquintocet, Cloquintocet-mexyl, Dietholate, Cyometrinil, Dichlormid, Dicyclonone, Cyprosulfamide, Daimuron, Naphthalic Anhydride Anhydride), fenchlorazole, fenchlorazole-ethyl (fenchlorazole-O-ethyl), fenclorim (fenclorim), furilazole (furilazole), fluxofenim (fluxofenim), flurazole (flurazole), benoxacor (benoxacor), metcamifen (metcamifen), mephenate (mephenate), mefenpyr (mefenpyr), mefenpyr-ethyl (mefenpyr-ethyl), mefenpyr-diethyl (mefenpyr-diethyl), lower alkyl substituted benzoic acid, 2,2-dichloro-N-(1,3-diisopropyl benzoate), xolane-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-dioxane (MG-191), 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67), 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, code number), MON4660 (code number), N1,N2-diallyl-N2-dichloroacetylglycinamide (DKA-24, code number), 1-bromo-4-[(chloromethyl)sulfonyl]benzene (CSB), 2-propenyl 1-oxa-4-azaspiro[4,5] Decane-4-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).

[0304] Next, examples of known biological pesticides that may be mixed or used in combination are listed below.

[0305] Biological pesticides: Haplothrips brevitubus, Franklinothrips vespiformis, Diglyphus isaea, Encarsia formosa, Amblyseius cucumeris, Pseudaphycus malinus, Amblyseius womersleyi, Aphidius colemani , Eretmocerus eremicus, Aphidoletes aphidimyza, Amblyseius swirskii, Orius strigicollis, Phytoseiulus persimilis, Amblyseius degenerans, Phytoseiulus persimilis, Orius sauteri, Dacnusa sibirica), Amblyseius californicus, Chrysoperla nipponensis, and Anicetus beneficus.

[0306] Next, examples of known agricultural materials that may be mixed or used in combination are listed below.

[0307] Agricultural materials: ethylene, hypochlorous acid water (limited to those 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 activation materials, soil spreading agents, soil permeability adjustment materials, soil water retention materials, etc., biostimulants.

[0308] Next, examples of known agricultural fertilizer components that may be mixed or used in combination are listed below.

[0309] Agricultural fertilizer components: Fertilizers include inorganic fertilizers and organic fertilizers, and examples of such agricultural fertilizer components include ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, ammonium urea nitrate, urea, lime nitrogen, potassium nitrate, calcium superphosphate, calcium triple superphosphate, potassium dihydrogen phosphate, potassium chloride, potassium sulfate, potassium carbonate, potassium silicate, oil cake, fish meal, rice bran, bat guano, and fermented chicken manure.

[0310] 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 present invention is not limited to these examples.

[0311] 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), grass 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 cucurbits, 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.);Sclerotium root rot (Thanatephorus cucumeris), Ascomycota: Rice blast (Pyricularia oryzae), Sesame leaf blight (Cochliobolus miyabeanus), Bakanae disease (Gibberella fujikuroi), Seedling blight (Fusarium avenaceum, Fusarium proliferatum, Fusarium solani, Trichoderma viride), Rice koji mold (Villosiclava virens); Cereal powdery mildew (Blumeria graminis f. sp. Hordei, Blumeria graminis f. sp. tritici), Spot blotch (Pyrenophora graminea), Net blotch (Pyrenophora teres), Fusarium head blight (Fusarium asiaticum, Fusarium avenaceum, Fusarium crookwellense, Fusarium culmorum, Gibberella zeae, Microdochium majus, Microdochium nivale), Snow rot Sclerotinia borealis, Pink snow mold (Microdochium nivale), Eyespot (Oculimacula acuformis, Oculimacula yallundae), Rhynchosporium (Rhynchosporium secalis f. sp. hordei), Septoria tritici blotch (Zymoseptoria tritici), Phaeosphaeria leaf blotch (Phaeosphaeria nodorum); Grape powdery mildew (Erysiphe necator var. necator), Anthracnose (Elsinoe ampelina), Late rot (Colletotrichum aenigma, Colletotrichum fioriniae, Colletotrichum fructicola, Colletotrichum gloeosporioides s. str.), Black rot (Guignardia bidwellii), Phomopsis cane and leaf spot (Phomopsis viticola), Brown leaf spot (Pseudocercospora vitis);Apple powdery mildew (Podosphaera leucotricha), scab (Venturia inaqualis), leaf spot (Alternaria mali), Monilinia mali, rot (Valsa) ceratosperma), Botryosphaeria kuwatsukai, Monilinia fructicola, Monilinia fructigena, Diplocarpon mali), anthrax (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 spot (Venturia nashicola), brown spot (Mycosphaerella pyri), canker (Phomopsis fukushii), anthracnose (Colletotrichum fioriniae, Glomerella cingulata); peach brown rot (Monilinia fructicola, Monilinia fructigena), black spot (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.), 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 wilt (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), anthrax (Colletotrichum acutatum, Colletotrichum gloeosporioides, Colletotrichum nigrum), leaf mold (Fulvia fulva), half-wilt (Verticillium dahliae), wilt (Fusarium oxysporum f. sp. lycopersici); eggplant powdery mildew (Erysiphe) cichoracearum, Leveillula taurica, Podosphaera xanthii), black blight (Corynespora cassicola), leaf mold (Mycovellosiella nattrassii); rapeseed sclerotinia (Sclerotinia sclerotiorum); cruciferous crop 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. Corynespora cassiicola; Common bean anthracnose (Colletotrichum lindemuthianum);Peanut black spot (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis, Cercospora canescens); pea powdery mildew (Erysiphe pisi); potato late 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 Colletotrichum fioriniae, Colletotrichum fragariae, Colletotrichum fructicola, Colletotrichum nymphaeae, Colletotrichum Banana black sigatoka disease (Mycosphaerella fijiensis), yellow sigatoka disease (Mycosphaerella musicola), Panama disease (Fusarium oxysporum, Fusarium oxysporum f. sp. cubense); gray mold (Botrytis cinerea) and stem rot (Sclerotinia sclerotiorum) of cucumber, tomato, kidney bean, strawberry, grape, etc.;Dollar spot of turfgrass (Clarireedia jacksonii, Clarireedia monteithiana), Curvularia leaf blight (Curvularia geniculata), damping-off (Gaeumannomyces graminis), anthracnose (Colletotrichum caudatum) Mucoromycotina: Rice seedling damping-off (Rhizopus chinensis, Rhizopus oryzae) Oomycota: Rice seedling damping-off (Pythium spp.); brown snow rot of wheat (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 peach blight (Phytophthora sp.); cucurbit downy mildew (Pseudoperonospora cubensis), blight (Phytophthora melonis, Phytophthora nicotianae), damping-off (Pythium cucurbitacearum, Pythium debaryanum); tomato, eggplant, and potato blight (Phytophthora infestans), damping-off (Pythium vexans), and root rot (Pythium aphanidermatum, Pythium myriotylum, Pythium dissotocum); leek 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.), fruit rot (Pythium ultimum var. ultimum); turfgrass Pythium disease (Pythium periplocum, Pythium graminicola, Pythium vanterpoolii) Bacteria: Burkholderia plantarii, Xanthomonas oryzae pv. oryzae, Burkholderia gradioli, Burkholderia glumae), Acidovorax avenae subsp. avenae, Pantoea ananatis; Brenneria nigrifluens, Pseudomonas syringae pv. pruni); citrus canker (Xanthomonas citri subsp. citri); cucurbit bacterial spot (Pseudomonas syringae pv. lachrymans); tomato canker (Clavibacter michiganensis subsp. michiganensis); potato scab (Streptomyces spp.); tea leaf spot (Pseudomonas syringae pv. theae); bacterial wilt of tomatoes, potatoes, etc. (Ralstonia solanacearum); soft rot of Chinese cabbage, leeks, onions, etc. (Pectobacterium carotovorum) Cercozoa: Brassicaceae crop clubroot disease (Plasmodiophora brassicae), etc.;

[0312] The agricultural and horticultural plant disease control agent of the present invention is effective in controlling 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 on plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance through genetic recombination, artificial crossbreeding, etc.

[0313] 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 techniques. New breeding techniques (NBTs) are described in the book "Understanding New Plant Breeding Techniques" (Kokusai Bunkensha, Ryo Osawa and Hiroshi Ezura), 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), etc.

[0314] 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 in any way. 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-ECS300 (300 MHz) or JMTC-400 (400 MHz) manufactured by JEOL Ltd., with tetramethylsilane (TMS) as an internal standard.

[0315] Example 1 Production of 1-(tert-butyl)-4-(3-chloro-2-fluorophenoxy)-N-{(2,4-dimethylbenzyl)oxy}-1H-pyrazole-5-carboxamide (Compound number of the present invention: A-0583)

[0316] A mixture of 0.16 g (0.51 mmol) of 1-(tert-butyl)-4-(3-chloro-2-fluorophenoxy)-1H-pyrazole-5-carboxylic acid, 0.23 g (0.61 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 0.20 g (1.53 mmol) of N-ethyldiisopropylamine, and 10 mL of N,N-dimethylformamide was stirred for 10 minutes under ice cooling, and after warming to room temperature, 0.14 g (0.77 mmol) of O-(2,4-dimethylbenzyl)hydroxyamine hydrochloride was added and stirred at room temperature for 3 hours. After completion of the reaction, saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer obtained by separation was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was evaporated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=9:1 to 7:3) to obtain 0.15 g (yield 65%) of the target product.

[0317] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 8.79 (1H,s), 7.11-7.18 (3H,m), 6.97-7.02 (2H,m), 6.84-6.92 (2H,m), 4.96 (2H,s), 2.37 (3H,s), 2.26 (3H,s), 1.71 (9H,s)

[0318] Example 2: Preparation of 2-{4-(3-chlorophenoxy)-5-methyl-1H-pyrazol-1-yl}-2-methylpropan-1-ol

[0319] ​A mixture of 5.00 g (20.9 mmol) of 3-(3-chlorophenoxy)-4-(dimethylamino)but-3-en-2-one, 4.29 g (82% purity, 25.0 mmol) of 2-hydrazineyl-2-methylpropan-1-ol hydrochloride, and 100 mL of 1,4-dioxane was stirred under reflux for 1.5 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=7:3) to obtain 3.61 g (yield 62%) of the target product.

[0320] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 7.27 (1H,s), 7.18-7.22 (1H,m), 6.98-7.02 (1H,m), 6.91-6.92 (1H,m), 6.80-6.83 (1H,m), 4.28 (1H,br), 3.95 (2H,s), 2.28 (3H,s), 1.55 (6H,s)

[0321] Example 3 Preparation of 4-(3-chlorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-5-methyl-1H-pyrazole To a mixture of 3.71 g (13.2 mmol) of 2-{4-(3-chlorophenoxy)-5-methyl-1H-pyrazol-1-yl}-2-methylpropan-1-ol and 30 mL of N,N-dimethylformamide was added 0.63 g of sodium hydride (60% purity, 15.9 mmol) under a nitrogen atmosphere and ice-cooling. After stirring for 15 minutes, 2.25 g (15.9 mmol) of iodomethane was added, and the mixture was warmed to room temperature and stirred for 18 hours. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and the organic layer was washed with saturated brine, saturated aqueous citric acid solution, and saturated aqueous sodium thiosulfate solution, and then dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to obtain 3.77 g (yield 97%) of the target product.

[0322] １ H-NMR data (400 MHz, CDCl​​３ / TMSδ (ppm)): 7.31 (1H, s), 7.16-7.21 (1H, m), 6.96-6.98 (1H, m), 6.90-6.91 (1H, m), 6.82-6.84 (1H, m), 3.63 (2H, s), 3.33 (3H, s), 2.28 (3H, s), 1.67 (6H, s)

[0323] Example 4 Preparation of 4-(3-chlorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carbaldehyde A mixture of 3.77 g (12.8 mmol) of 4-(3-chlorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-5-methyl-1H-pyrazole, 2.02 g (25.6 mmol) of pyridine, 7.61 g (32.0 mmol) of sodium peroxodisulfate, 1.28 g (5.12 mmol) of copper(II) sulfate pentahydrate, 50 mL of acetonitrile, and 30 mL of water was heated and stirred at 80°C for 6 hours. After completion of the reaction, ethyl acetate was added to the reaction mixture, which was then filtered through Celite. The filtrate was evaporated under reduced pressure. Ethyl acetate and water were added to the residue, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to obtain 2.00 g (yield 51%) of the target product.

[0324] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 9.83 (1H, s), 7.24-7.30 (2H, m), 7.09-7.14 (2H, m), 6.98-7.01 (1H, m), 3.81 (2H, s), 3.31 (3H, s), 1.69 (6H, s)

[0325] ​Example 5 Preparation of 4-(3-chlorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carboxylic acid To a mixture of 2.00 g (6.48 mmol) of 4-(3-chlorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carbaldehyde, 4.09 g (58.3 mmol) of 2-methylbut-2-ene, 40 mL of tert-butanol, and 20 mL of water, was added 2.20 g (80% purity, 19.4 mmol), 4.66 g (38.9 mmol) of sodium dihydrogen phosphate, and 10 mL of water under ice cooling, followed by stirring at room temperature for 2 hours. After completion of the reaction, 1 N hydrochloric acid was added, and the mixture was extracted with chloroform. The organic layer was treated with a 1N aqueous solution of sodium hydroxide, and the aqueous layer was separated. The pH was adjusted to 1-2 with 1N hydrochloric acid and extracted again with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was evaporated under reduced pressure, and the residue was washed with n-hexane to obtain 1.72 g of the target product (yield 82%).

[0326] １ H-NMR data (400 MHz, d ６ -DMSO / TMSδ (ppm)): 7.50 (1H, s), 7.34-7.38 (1H, m), 7.10-7.14 (1H, m), 6. 94-6.96 (1H, m), 6.87-6.91 (1H, m), 3.77 (2H, s), 3.21 (3H, s), 1.61 (6H, s)

[0327] ​Example 6: Preparation of 4-(3-chlorophenoxy)-N-{(2,4-dimethylbenzyl)oxy}-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carboxamide (Compound number of the present invention: A-0211) A mixture of 0.20 g (0.62 mmol) of 4-(3-chlorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carboxylic acid, 0.14 g (0.74 mmol) of O-(2,4-dimethylbenzyl)hydroxyamine hydrochloride, 0.28 g (0.74 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 0.24 g (1.85 mmol) of N-ethyldiisopropylamine, and 10 mL of N,N-dimethylformamide was stirred at room temperature for 18 hours, and then heated and stirred for 3 hours at 50° C. After completion of the reaction, a saturated aqueous citric acid solution and ethyl acetate were added to the reaction solution, and the organic layer obtained by separation was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was evaporated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=7:3) to obtain 0.28 g of the target product (yield 99%).

[0328] １ H-NMR data (400 MHz, CDCl ３ / TMSδ (ppm)): 9.00 (1H, s), 7.20-7.24 (2H, m), 7.06-7.10 (2H, m), 6.98-6.99 (1H, m), 6.94-6.95 (1H, m), 6.84-6.89 (2H, m), 4.91 (2H, s), 3.77 (2H, s), 3.26 (3H, s), 2.34 (3H, s), 2.29 (3H, s), 1.69 (6H, s)

[0329] ​Example 7: Preparation of 2-{4-(3-chloro-2-fluorophenoxy)-5-methyl-1H-pyrazol-1-yl}-2-methylpropan-1-ol. A mixture of 2.00 g (7.76 mmol) of 3-(3-chloro-2-fluorophenoxy)-4-(dimethylamino)but-3-en-2-one, 1.31 g (9.31 mmol) of 2-hydrazineyl-2-methylpropan-1-ol hydrochloride, 0.47 g (7.76 mmol) of acetic acid, and 20 mL of 1,4-dioxane was heated and stirred at 90°C for 1.5 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After filtering off insoluble matter, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=1:1) to obtain 0.97 g of the target product (yield 42%).

[0330] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 7.26 (1H,s), 7.03-7.07 (1H,m), 6.91-6.96 (1H,m), 6.73-6.77 (1H,m), 4.22 (1H,br), 3.94 (2H,s), 2.32 (3H,s), 1.55 (6H,s)

[0331] ​Example 8 Preparation of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-5-methyl-1H-pyrazole To a mixture of 1.28 g (4.28 mmol) of 2-{4-(3-chloro-2-fluorophenoxy)-5-methyl-1H-pyrazol-1-yl}-2-methylpropan-1-ol and 30 mL of N,N-dimethylformamide was added 0.26 g (60% purity, 6.43 mmol) of sodium hydride under a nitrogen atmosphere and ice-cooling. After stirring for 15 minutes, 0.73 g (5.14 mmol) of iodomethane was added, and the mixture was warmed to room temperature and stirred for 18 hours. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and the organic layer was washed with saturated brine, saturated aqueous citric acid solution, and saturated aqueous sodium thiosulfate solution, and then dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=7:3) to obtain 1.22 g (yield 91%) of the target product.

[0332] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 7.31 (1H,s), 7.00-7.05 (1H,m), 6.88-6.94 (1H,m), 6.72-6.77 (1H,m), 3.63 (2H,s), 3.32 (3H,s), 2.31 (3H,s), 1.66 (6H,s)

[0333] ​Example 9 Preparation of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carbaldehyde A mixture of 1.20 g (3.84 mmol) of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-5-methyl-1H-pyrazole, 0.61 g (7.67 mmol), 2.28 g (9.59 mmol) of sodium peroxodisulfate, 0.38 g (1.53 mmol) of copper(II) sulfate pentahydrate, 30 mL of acetonitrile, and 10 mL of water was heated and stirred at 80°C for 1 hour. After completion of the reaction, ethyl acetate was added to the reaction mixture, which was then filtered through Celite, and the filtrate was evaporated under reduced pressure. Ethyl acetate and water were added to the residue, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to obtain 0.21 g (yield 17%) of the target product and 0.55 g (yield 44%) of {4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazol-5-yl}methanol.

[0334] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 9.92 (1H, s), 7.19-7.23 (1H, m), 7.16 (1H, s), 7.02-7.08 (2H, m), 3.80 (2H, s), 3.30 (3H, s), 1.68 (6H, s)

[0335] {4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazol-5-yl}methanol

[0336] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 7.33 (1H,s), 7.04-7.08 (1H,m), 6.91-6.96 (1H,m), 6.81-6.85 (1H,m), 4.64 (2H,s), 3.56 (2H,s), 3.39 (1H,br), 3.33 (3H,s), 1.78 (6H,s)​​

[0337] Example 10 Preparation of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carbaldehyde A mixture of 0.53 g (1.60 mmol) of {4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazol-5-yl}methanol, 0.38 g (4.80 mmol), 0.58 g (2.40 mmol) of sodium peroxodisulfate, 0.16 g (0.64 mmol) of copper(II) sulfate pentahydrate, 10 mL of acetonitrile, and 5 mL of water was heated and stirred at 90°C for 5 hours. After completion of the reaction, ethyl acetate was added to the reaction mixture, which was then filtered through Celite. The filtrate was evaporated under reduced pressure. Ethyl acetate and water were added to the residue, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to obtain 0.18 g (yield 34%) of the target product.

[0338] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 9.92 (1H, s), 7.19-7.23 (1H, m), 7.16 (1H, s), 7.02-7.08 (2H, m), 3.80 (2H, s), 3.30 (3H, s), 1.68 (6H, s)

[0339] ​Example 11 Preparation of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carboxylic acid To a mixture of 0.40 g (1.22 mmol) of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carbaldehyde, 0.77 g (11.0 mmol) of 2-methylbut-2-ene, 20 mL of tert-butanol, and 5 mL of water, 0.42 g (80% purity, 3.67 mmol), 0.88 g (7.35 mmol) of sodium dihydrogen phosphate, and 5 mL of water were added under ice cooling, followed by stirring at room temperature for 3 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was distilled off under reduced pressure, and the residue was washed with n-hexane to obtain 0.29 g (yield 69%) of the target product.

[0340] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 7.26 (1H, s), 7.13-7.17 (1H, m), 6.94-7.02 (2H, m), 3.81 (2H, s), 3.38 (3H, s), 1.73 (6H, s)

[0341] ​Example 12: Preparation of 4-(3-chloro-2-fluorophenoxy)-N-{(2,4-dimethylbenzyl)oxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carboxamide (Compound number of the present invention: A-1880) A mixture of 0.13 g (0.38 mmol) of 4-(3-chloro-2-fluorophenoxy)-1-(1-methoxy-2-methylpropan-2-yl)-1H-pyrazole-5-carboxylic acid, 0.09 g (0.46 mmol) of O-(2,4-dimethylbenzyl)hydroxyamine hydrochloride, 0.17 g (0.46 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 0.15 g (1.14 mmol) of N-ethyldiisopropylamine, and 10 mL of N,N-dimethylformamide was stirred at room temperature for 18 hours, and then heated and stirred for 3 hours at 50° C. After completion of the reaction, a saturated aqueous citric acid solution and ethyl acetate were added to the reaction solution, and the organic layer obtained by separation was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering off the insoluble matter, the solvent was evaporated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=7:3) to obtain 0.14 g of the target product (yield 78%).

[0342] １ H-NMR data (400 MHz, CDCl ３ / TMSδ(ppm)): 9.01 (1H,s), 7.19 (1H,s), 7.12-7.16 (2H,m), 6.96-7.02 (2H,m), 6.86-6.94 (2H,m), 4.95 (2H,s), 3.75 (2H,s), 3.25 (3H,s), 2.37 (3H,s), 2.27 (3H,s), 1.68 (6H,s)

[0343] Reference example

[0344] Preparation of O-(2,4-dimethylbenzyl)hydroxyamine hydrochloride

[0345] (1) Preparation of 2-[(2,4-dimethylbenzyl)oxy]isoindoline-1,3-dione

[0346] ​To a mixture of 5.00 g (36.71 mmol) of (2,4-dimethylphenyl)methanol, 6.59 g (40.40 mmol) of N-hydroxyphthalimide, 10.60 g (40.40 mmol) of triphenylphosphine, and 200 mL of tetrahydrofuran, 18.4 mL of a diethyl azodicarboxylate toluene solution (concentration: 2.2 mol / L, 40.40 mmol) was added under a nitrogen atmosphere and ice-cooled, and the mixture was stirred for 1 hour. The temperature was raised to room temperature and the mixture was stirred overnight. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 4:1), yielding 3.85 g (yield 37%) of the target product.

[0347] １ H-NMR data (300 MHz, CDCl ３ / TMSδ (ppm)): 7.78-7.82 (2H, m), 7.71-7.76 (2H, m), 7.23-7.26 (1H, m), 7.05-7.07 (1H, m), 6.93-6.98 (1H, m), 5.20 (2H, s), 2.57 (3H, s), 2.31 (3H, s)

[0348] (2) Preparation of O-(2,4-dimethylbenzyl)hydroxyamine hydrochloride

[0349] To a mixture of 2.34 g (8.32 mmol) of 2-[(2,4-dimethylbenzyl)oxy]isoindoline-1,3-dione, 20 mL of dichloromethane, and 20 mL of methanol, 1.25 g (24.97 mmol) of hydrazine monohydrate was added and stirred at room temperature overnight. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a mixture of the crude product and 20 mL of 1,4-dioxane, 6.24 mL of a hydrogen chloride / 1,4-dioxane solution (concentration: 4 mol / L, 25.00 mmol) was added under ice cooling, and the mixture was warmed to room temperature and stirred for 1 hour. The precipitated compound was collected by filtration, washed with n-hexane, and then air-dried to obtain 1.52 g of the target product (yield: 97%).

[0350] １ ​​H-NMR data (300 MHz, DMSO-d ６ / TMSδ(ppm)): 10.90-11.10 (2H, br), 7.19-7.22 (1H, m), 7.01-7.07 (2H, m), 5.02 (2H, s), 2.32 (3H, s), 2.28 (3H, s)

[0351] The physical properties (melting point, refractive index, and １ H-NMR spectral data, including the values ​​in the above examples, are shown in Tables 69 to 74 below. The compound numbers and symbols in the tables have the same meanings as above.

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358] Next, specific formulation examples of the agricultural and horticultural plant disease control agent of the present invention using the N-oxy-pyrazole-5-carboxamide compound or salt thereof 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.

[0359] Formulation Example 1 Emulsifiable concentrate Each compound shown in Tables 1 to 68 10 parts Cyclohexanone 30 parts Polyoxyethylene alkylaryl ether 11 parts Calcium alkylbenzenesulfonate 4 parts Methylnaphthalene 45 parts The above ingredients were uniformly dissolved to prepare an emulsifiable concentrate.

[0360] Formulation Example 2 Wettable Powder Each compound shown in Tables 1 to 68 10 parts Naphthalenesulfonic acid formalin condensate sodium salt 0.5 parts Polyoxyethylene alkyl aryl ether 0.5 parts Diatomaceous earth 24 parts Clay 65 parts The above ingredients were uniformly mixed and pulverized to give wettable powders.

[0361] Formulation Example 3 Dusts Each compound shown in Tables 1 to 68 2 parts Diatomaceous earth 5 parts Clay 93 parts The above ingredients were uniformly mixed and pulverized to give dusts.

[0362] Formulation Example 4 Granules Each compound shown in Tables 1 to 68 5 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium ligninsulfonate 5 parts Carboxymethylcellulose 2 parts Clay 86 parts The above ingredients were uniformly mixed and pulverized. To this mixture was added an amount of water equivalent to 20 parts, and the mixture was kneaded, processed into 14-32 mesh granules using an extrusion granulator, and then dried to give granules.

[0363] Formulation Example 5 Flowable formulation Each compound shown in Tables 1 to 68 20 parts Polyoxyethylene styrenated phenyl ether sulfate 4 parts Ethylene glycol 7 parts Silicone AF-118N (manufactured by Asahi Chemical Industry Co., Ltd.) 0.02 parts Water 68.98 parts The above ingredients were mixed in a high-speed mixer for 30 minutes, and then pulverized in a wet pulverizer to give a flowable formulation.

[0364] Formulation Example 6 Water Dispersible Granules Each compound shown in Tables 1 to 68 10 parts Sodium ligninsulfonate 5 parts Polyoxyethylene alkylaryl ether 1 part Sodium polycarboxylate 3 parts White carbon 5 parts Pregelatinized starch 1 part Calcium carbonate 65 parts Water 10 parts The above ingredients were mixed, kneaded, and granulated. The resulting granules were dried in a fluidized bed dryer to give water dispersible granules.

[0365] Next, the effects of the disease control agent of the present invention will be explained using test examples.

[0366] Test Example: Test of preventive effect against cucumber gray mold (Botrytis cinerea) Cucumber seeds were sown in pots, and the grown cucumber seedlings were sprayed with a solution adjusted to a concentration of 500 ppm of the active ingredient. Thereafter, filter paper soaked in Botrytis cinerea gray mold spores (Botrytis cinerea) suspended in a liquid medium containing 0.3% yeast extract and 2% glucose was placed on the surface of the cucumber cotyledons for inoculation, and the cucumbers were then transferred to a moist chamber and maintained therein. After sufficient disease development in the untreated group, the disease severity of the inoculated leaves was indexed according to the criteria in Table 75 below. The disease severity was calculated using the formula shown in Equation 1, and the control value was calculated using the formula shown in Equation 2.

[0367]

[0368]

[0369] [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.]

[0370]

[0371] As a result of the tests, the compound numbers of the present invention, A-0022, A-0023, A-0024, A-0034, A-0035, A-0036, A-0045, A-0046, A-0047, A-0061, A-0063, A-0064, A-0066, A-0077, A-0079, A-...A-1210, A-1323, A-1324, A-1325, A-1327, A-1328, A-1507, A-1508, A-1509, A-1511, A-1512, A-1526, A-1534, A-1575, A- 1718, A-1731, A-1735, A-1877, A-1880, A-2744, A-2755, A-2756, A-2757, A-2758, A-2759, A-2760, and B-0006 had a control value of 100. ,

[0372] The present invention provides a novel N-oxy-pyrazole-5-carboxamide compound or a salt thereof having a high control effect, a production intermediate thereof, and a plant disease control agent containing the compound as an active ingredient. The present invention is useful in the fields of agrochemicals and agriculture and has industrial applicability.

Claims

1. General formula [I] [wherein T represents an oxygen atom or a sulfur atom; R １ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group or C ３ ~C ８ Each of the groups represents a halocycloalkyl group, and each of the groups may have one or more R ５ and R ２ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkoxy-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonylamino-C １ ~C ６ alkyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylcarbonylamino-C ３ ~C ８ Cycloalkyl group (the amino group is R ６ (C １ ~C ６ Alkylcarbonylamino-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylsulfanyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfanyl-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkylsulfanyl-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkylsulfinyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkylsulfinyl-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkylsulfonyl-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkylsulfonyl-C １ ~C ６ alkyl)-C ３ ~C ８ Cycloalkyl group, C ６ ~C １２ an aryl group, a 9- to 12-membered carbocyclyl group, or a 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R ５ and R ３ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, cyano C １ ~C ６ Alkyl group, or C ６ ~C １２ Aryl-C １ ~C ６ Each of the above groups may have one or more R ５ A is optionally substituted by a substituent selected from C ６ ~C １２ an aryl group, a 9- to 12-membered carbocyclyl group, a 3- to 6-membered heterocyclyl group, or a 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R ５ and R ４ and R ４’ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, or C １ ~C ６ represents a haloalkyl group, or R ４ and R ４’ may be taken together to form an oxo group (=O), or R ４ and R ４’ may each together with the carbon atom to which they are attached form a 3- to 8-membered monocyclic carbocyclyl group, which carbocyclyl group is １ ~C ６ Q may be substituted with one or more substituents selected from alkyl groups, ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, C ６ ~C １２ an aryl group, a 9- to 12-membered carbocyclyl group, a 3- to 6-membered heterocyclyl group, or a 5- to 12-membered heteroaryl group, and any of the above groups may have one or more R ５ and R ４ and Q may each together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclyl group or a 5- to 12-membered heterocyclyl group having one heteroatom selected from an oxygen atom, a nitrogen atom and a sulfur atom, and the carbocyclyl group may further include a halogen atom, and C １ ~C ６ The heterocyclyl group may be substituted with one or more substituents selected from alkyl groups, and when substituted with two or more substituents, the substituents may be the same or different. The heterocyclyl group may be substituted with one or more substituents selected from halogen atoms and C １ ~C ６ It may be substituted with one or more substituents selected from alkyl groups, and when it is substituted with two or more substituents, the substituents may be the same or different. In the case of a heterocyclyl group containing a nitrogen atom, when the nitrogen atom can be substituted, R ６ and R ５ represents a hydroxy group, a halogen atom, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C ３ ~C ８ Halocycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Haloalkyl-C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Halocycloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Haloalkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, hydroxy C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ８ Cycloalkoxy group, 3- to 6-membered heterocyclyl group, 3- to 6-membered heterocyclyloxy group, 3- to 6-membered heterocyclyl-C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl group, C ６ ~C １２ Aryloxy group, C ６ ~C １２ Aryl-C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl-C ２ ~C ６ Alkynyl group, 9- to 12-membered carbocyclyl group, 5- to 12-membered heteroaryl group, 5- to 12-membered heteroaryloxy group, 5- to 12-membered heteroaryl-C １ ~C ６ Alkoxy group, 5- to 12-membered heteroaryl-C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxy group, C ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxycarbonyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfanyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfinyl-C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylsulfonyl-C １ ~C ６ Alkoxy group, C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkoxy group, hydroxy C １ ~C ６ Alkoxy group, cyano C １ ~C ６ Alkoxy group, cyano C ３ ~C ８ Cycloalkyl-C １ ~C ６ Alkoxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylcarbonyloxy group, C ３ ~C ８ cycloalkylcarbonyloxy group, C １ ~C ６ Alkyl-C ３ ~C ８ cycloalkylcarbonyloxy group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C ３ ~C ８ cycloalkylcarbonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylcarbonyl group, formyl group, carboxyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Haloalkoxycarbonyl group, C ３ ~C ８ cycloalkoxycarbonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ alkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylaminocarbonyl group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkylaminocarbonyl-C １ ~C ６ Alkoxy group (the amino group is R ６ a mercapto group, C １ ~C ６ Alkylsulfanyl group, C １ ~C ６ Haloalkylsulfanyl group, C ３ ~C ８ Cycloalkylsulfanyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfanyl group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Haloalkylsulfinyl group, C ３ ~C ８ Cycloalkylsulfinyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkylsulfonyl group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkylsulfonyl group, amino group, C １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ６ ~C １２ Arylcarbonylamino group (the amino group is R ６ a 3- to 6-membered heterocyclylcarbonylamino group (the amino group may be substituted with a substituent selected from R ６ a 5- to 12-membered heteroarylcarbonylamino group (the amino group may be substituted with a substituent selected from R ６ may be substituted with a substituent selected from ６ ~C １２ An arylaminocarbonyl group (the amino group is R ６ a 3- to 6-membered heterocyclylaminocarbonyl group (the amino group may be substituted with a substituent selected from R ６ a 5- to 12-membered heteroarylaminocarbonyl group (the amino group may be substituted with a substituent selected from R ６ may be substituted with a substituent selected from １ ~C ６ Alkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ haloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkoxycarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C １ ~C ６ haloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C ３ ~C ８ A cycloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), C １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylaminocarbonylamino group (the amino group is R ６ and two amino groups are optionally substituted with a substituent selected from R ６ may be the same or different), -C(=NR ７ ) R ８ group, or —OCH ２ C (=NR ７ ) R ８ Each of the groups may be the same or different and may have one or more R ９ and R ６ is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkoxy-C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ７ is a hydroxy group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ８ Cycloalkoxy group, C １ ~C ６ Alkyl-C ３ ~C ８ Cycloalkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ alkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ may be substituted with a substituent selected from １ ~C ６ Alkyl-C ３ ~C ８ A cycloalkylcarbonylamino group (the amino group is R ６ and R ８ is a hydrogen atom, C １ ~C ６ Alkyl group, or C ３ ~C ８ represents a cycloalkyl group, R ９ represents a hydroxy group, a halogen atom, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ haloalkoxy group, or C ３ ~C ８ A compound represented by the formula (I) or a salt thereof:

2. The compound represented by general formula [I] is a compound represented by general formula [IA] (In the formula, A, R ２ and Q have the same meanings as in claim 1. The compound or salt thereof according to claim 1, which is a compound represented by the formula:

3. The compound represented by general formula [I] is a compound represented by general formula [IB] (In the formula, A, R ２ and R ５ has the same meaning as in claim 1, and n represents an integer of 0, 1, 2, 3, 4, or 5. The compound or salt thereof according to claim 1, 4. The compound represented by general formula [I] is a compound represented by general formula [IC] (In the formula, A, R ５ and n have the same meaning as in claim 3, R ２’ is hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy-C ３ ~C ８ cycloalkyl groups, (C １ ~C ６ Alkoxy-C １ ~C ６ alkyl)-C ３ ~C ８ Each of the groups may be substituted with one or more R ５ The compound or salt thereof according to claim 1, which is a compound represented by the formula:

5. An agricultural and horticultural plant disease control agent comprising the compound or salt thereof according to claim 1, 2, 3 or 4 as an active ingredient.

6. The agricultural and horticultural plant disease control agent according to claim 5, wherein the plant disease is caused by a pathogenic fungus.

7. The agricultural and horticultural plant disease control agent according to claim 6, wherein the pathogenic fungus is classified into the kingdom Fungi, Stramenopila, Rhizaria and Bacteria.

8. An agricultural and horticultural plant disease control composition comprising the compound or salt thereof according to claim 1, 2, 3 or 4 and an agriculturally acceptable carrier.

9. A method for controlling diseases of useful plants, which comprises spraying an effective amount of the compound or salt thereof according to claim 1, 2, 3 or 4 onto a useful plant or a part of a useful plant, or onto a place where the useful plant is growing.

10. The method according to claim 9, wherein the plant disease is caused by a pathogenic fungus.

11. The method of claim 10, wherein the pathogenic fungus is classified into the kingdom Fungi, Stramenopila, Rhizaria and Bacteria.

12. Use of the compound or salt thereof according to claim 1, 2, 3 or 4 as an agricultural or horticultural plant disease control agent for useful plants.

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