Azolyloxy heterocyclic compound or salt thereof, agrochemical composition, and herbicide

Abstract

The present invention addresses the problem of providing: a novel azolyloxy heterocyclic compound or a salt thereof having excellent herbicidal activity; and a herbicide containing the same as an active ingredient.　Provided are: an azolyloxy heterocyclic compound represented by general formula [I] [In the formula, R1 denotes a C1-C6 alkyl group or the like, R3 denotes a C1-C6 haloalkyl group or the like, A1 denotes an oxygen atom or the like and A3 denotes a nitrogen atom, or A1 denotes a nitrogen atom and A3 denotes an oxygen atom or the like, A4, A5, A6 and A7 each independently denote a nitrogen atom, C-H or C-R4, R4 moieties each independently denote a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or the like, R2 denotes a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C6-C12 aryl group or the like that may be unsubstituted or substituted with R5, or the like, and R5 denotes a halogen atom, a C1-C6 alkyl group, or the like.], or a salt thereof; and a herbicide characterized by containing the same as an active ingredient.

Description

Azolyloxy heterocyclic compound or its salt, pesticide composition and herbicide

[0001] The present invention relates to a novel azolyloxy heterocyclic compound or a salt thereof, and a herbicide containing said compound or a salt thereof as an active ingredient.

[0002] Conventionally, the following compounds have been known as azolyloxy heterocyclic compounds (see, for example, Patent Documents 1 to 3 and Non-Patent Document 1).

[0003] Patent Documents 1 to 3 and Non-Patent Document 1 describe azolyloxy heterocyclic compounds having herbicidal activity.

[0004] International Publication No. 2022 / 101270 International Publication No. 2020 / 169509 International Publication No. 2019 / 016066

[0005] European Journal of Organic Chemistry (2021) (41), 5677-5684

[0006] The compounds described in Patent Documents 1 to 3 and Non-Patent Document 1 are insufficient in herbicidal activity, etc. Furthermore, Patent Documents 1 to 3 and Non-Patent Document 1 disclose only monocyclic groups as ring structures bonded to azoles, and make no mention of fused ring groups.

[0007] The above Patent Documents 1 to 3 and Non-Patent Document 1 do not disclose the azolyloxy heterocyclic compound of the present invention at all.

[0008] In the cultivation of useful plants, the occurrence of various weeds has a significant impact on the production efficiency of plants, harvests, and products. However, conventional herbicides have insufficient control efficacy, and the emergence of weeds resistant to them has become a problem. Therefore, in order to control these weeds, there is a need to create herbicides that have excellent properties at lower dosages. Furthermore, there is an increasing demand for the safety of chemicals and their impact on the environment, and the development of safer herbicides is desired.

[0009] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a compound having herbicidal activity capable of controlling various weeds that occur in upland fields, orchards, paddy fields, non-agricultural lands, etc., and a herbicide containing the same.

[0010] In order to achieve the above object, the present inventors have synthesized a large number of azolyloxy heterocyclic compounds and intensively investigated their herbicidal activity and usefulness. As a result, they have found that various weeds can be controlled for a long period of time by applying to plants an azolyloxy heterocyclic compound represented by the following general formula [I] (hereinafter, sometimes referred to as "the compound of the present invention"). Further research has led to the completion of the present invention.

[0011] That is, the present invention has the following characteristics: (1) A compound represented by general formula [I]

[0012]

[0013] [In general formula [I], A １ When is a nitrogen atom, A ３ represents an oxygen atom or a sulfur atom, and A ３ When is a nitrogen atom, A １ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ２ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a cyanato group, an isocyanato group, a thiocyanato group, an isothiocyanato group, a nitro group, C １ ~C ６ Alkyl group (the C １ ~C ６ The alkyl group is R７ substituents), C ２ ~C ６ Alkenyl group (C ２ ~C ６ The alkenyl group is R ７ substituents), C ２ ~C ６ Alkynyl group (C ２ ~C ６ The alkynyl group is R ７ substituents), C ３ ~C ６ Cycloalkyl group (the C ３ ~C ６ The cycloalkyl group is R ７ substituents), a heterocyclyl group (the heterocyclyl group is ５ substituents), C ６ ~C １２ Aryl group (the C ６ ~C １２ The aryl group is R ５ substituents), a heteroaryl group (a heteroaryl group is a ５ substituents), C ７ ~C １４ Aralkyl group (said C ７ ~C １４ The aralkyl group is R ５ substituents), a heteroaralkyl group (the heteroaralkyl group may be substituted with one or more substituents selected from R ５ substituents), a hydroxy group, C １ ~C ６ Alkoxy group (the C １ ~C ６ The alkoxy group is R ７ substituents), C ２ ~C ６ Alkenyloxy group (C ２ ~C ６The alkenyloxy group is R ７ substituents), C ２ ~C ６ Alkynyloxy group (C ２ ~C ６ The alkynyloxy group is R ７ substituents), C ３ ~C ６ A cycloalkyloxy group (the C ３ ~C ６ The cycloalkyloxy group is R ７ substituents), C ６ ~C １２ An aryloxy group (the C ６ ~C １２ The aryloxy group is R ５ substituents), a heteroaryloxy group (the heteroaryloxy group is ５ substituents), C ７ ~C １４ Aralkyloxy group (said C ７ ~C １４ The aralkyloxy group is R ５ substituents), a heteroaralkyloxy group (the heteroaralkyloxy group may be substituted with one or more substituents selected from R ５ substituents), a sulfanyl group, a pentahalosulfanyl group, a formylthio group, C １ ~C ６ Alkylcarbonylthio group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３~C ６ Cycloalkylthio group, C ３ ~C ６ Cycloalkylsulfinyl group, C ３ ~C ６ Cycloalkylsulfonyl group, C ３ ~C ６ Halocycloalkylthio group, C ３ ~C ６ Halocycloalkylsulfinyl group, C ３ ~C ６ Halocycloalkylsulfonyl group, C ６ ~C １２ Arylthio group, C ６ ~C １２ Arylsulfinyl group, C ６ ~C １２ Arylsulfonyl group, heteroarylthio group, heteroarylsulfinyl group, heteroarylsulfonyl group, carboxyl group, C １ ~C ６ an alkoxycarbonyl group, an aminocarbonyl group (the nitrogen atom of the aminocarbonyl group is R ６ substituents), an aminothiocarbonyl group (the nitrogen atom of the aminothiocarbonyl group may be substituted with one or more substituents selected from R ６ substituents), an amino group (the amino group may be substituted with one or more substituents selected from R ６ (substituted with one or more substituents selected from the group consisting of di(C １ ~C ６ R represents an alkyl)sulfinylidene)amino group; ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C１ ~C ６ represents an alkoxycarbonyl group, R ４ are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ R represents an alkyl)amino group; ５ represents a halogen atom, an azide group, a cyano group, a nitro group, a hydroxy group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６Haloalkoxy group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, carboxyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, mono(C １ ~C ６ alkyl)aminocarbonyl group, di(C １ ~C ６ alkyl)aminocarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ R represents an alkyl)amino group; ６ is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ represents a haloalkoxy group or a hydroxy group, and R ６ may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which it is attached, ７ represents a halogen atom, a cyano group, a nitro group, a hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, C ３ ~C ６ Halocycloalkyl group, cyano C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ a haloalkylsulfonyl group.] or a salt thereof.

[0014] (2) In the formula [I], A １ is an oxygen atom, A ３ is a nitrogen atom, A ４ is C-H, A ５ is C-R ４ , A ６ is C-R ４ , A ７ is C-R ４ indicates, R １ is C １ ~C ６ alkyl group, R ２ is C １ ~C ６ The azolyloxy heterocyclic compound or salt thereof according to (1) above, which represents a haloalkyl group.

[0015] (3) In the formula [I], A １ is an oxygen atom, A ３ is a nitrogen atom, A ４ is C-H, A ５ is C-H, A ６ is C-R ４ , A ７ represents C—H, and R １ is C １ ~C ６ alkyl group, R ２ is C １ ~C ６ The azolyloxy heterocyclic compound or salt thereof according to (1) above, which represents a haloalkyl group.

[0016] (4) In the formula [I], A ３ represents a nitrogen atom, R １ is C １ ~C６ alkyl group, R ２ is C １ ~C ６ The azolyloxy heterocyclic compound or salt thereof according to (1) above, which represents a haloalkyl group.

[0017] (5) In the formula [I], A １ represents a nitrogen atom, R １ is C １ ~C ６ alkyl group, R ２ is C １ ~C ６ The azolyloxy heterocyclic compound or salt thereof according to (1) above, which represents a haloalkyl group.

[0018] (6) A pesticide composition comprising the azolyloxy heterocyclic compound or its salt according to any one of (1) to (5) above as an active ingredient.

[0019] (7) The pesticide composition according to (6) above, further comprising a surfactant.

[0020] (8) A herbicide containing the azolyloxy heterocyclic compound or its salt according to any one of (1) to (5) above as an active ingredient.

[0021] (9) The herbicide according to (8) above, which has herbicidal activity against weeds that grow in fields, paddy fields, orchards, lawns, non-agricultural land, greenhouses, nursery facilities, or plant factories where useful plants having agricultural, horticultural, and industrial uses are cultivated.

[0022] (10) The herbicide according to (9) above, wherein the useful plant having agricultural, horticultural and industrial uses is a plant transformed in cultivation by breeding or genetic engineering techniques.

[0023] (11) A method for controlling weeds, which comprises using an active ingredient amount of the azolyloxy heterocyclic compound or salt thereof described in (1) to (5) above.

[0024] (12) A method for controlling weeds, comprising simultaneously or in divided doses applying the pesticide composition according to (6) or (7) to useful plants having agricultural, horticultural and industrial uses or to a place where useful plants having agricultural, horticultural and industrial uses are intended to grow or are growing.

[0025] (13) The method for controlling weeds according to (11) or (12), wherein the place to which the herbicide according to (8) is applied is a paddy field, a field, a lawn, an orchard, a non-agricultural land, a greenhouse, a nursery facility, or a plant factory.

[0026] (14) A method for using the herbicide according to any one of (8) to (10) above for controlling weeds in useful plants for agricultural, horticultural, and industrial uses.

[0027] (15) General formula [VI]

[0028]

[0029] [In general formula [VI], A １ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ The compound of the present invention is an intermediate for producing the compound represented by the general formula [I] or a salt thereof according to (1), wherein the compound is represented by the formula:

[0030] (16) General formula [IX]

[0031]

[0032] [In general formula [IX], A ３ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４ are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ The compound of the present invention is an intermediate for producing the compound represented by the general formula [I] or a salt thereof according to (1), wherein the compound is represented by the formula:

[0033] (17) A method for producing the compound represented by the general formula [I] described in (1) above or a salt thereof, characterized in that the compound described in (15) or (16) above or a salt thereof is used as a raw material.

[0034] The azolyloxy heterocyclic compound represented by the general formula [I] of the present invention or a salt thereof can control various weeds that grow in upland fields, paddy fields, orchards, non-agricultural lands, etc., and has excellent effects as a pesticide.

[0035] The compound which is an intermediate for producing the compound represented by the general formula [I] of the present invention or a salt thereof is a compound which is useful as an intermediate for producing the above-mentioned azolyloxy heterocyclic compound represented by the general formula [I] of the present invention or a salt thereof.

[0036] The symbols and terms used in this specification will be explained below.

[0037] In the present invention, the term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0038] In the present invention, "C １ ~C ６ " indicates that the number following the element symbol represents the number of carbon atoms, and in this case, for example, the number of carbon atoms may be anywhere in the range of 1 to 6.

[0039] 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, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

[0040] 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, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl vinyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1-(isobutyl)vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-(isopropyl)-2-propenyl, 2-methyl-2-pentenyl thenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl, or 2,4-hexadienyl groups.

[0041] In the present invention, "C ２ ~C ６Unless 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, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-(n- Examples of such groups include 1-(isopropyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butynyl, and 2,2-dimethyl-3-butynyl.

[0042] In the present invention, "C １ ~C ６Unless otherwise specified, the term "haloalkyl group" refers to a linear or branched 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, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 , 1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2-trichloroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1 -difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoropropan-2-yl, 2-fluoropropan-2-yl, 1,1-difluoropropan-2-yl, 1,2-difluoropropan-2-yl, 1,3-difluoropropan-2-yl, 1,2,3-trifluoropropan-2-yl, 1,1,3,3-tetrafluoropropan-2-yl, 1,1,1,3,3,3-hexafluoropropane- 2-yl, heptafluoropropan-2-yl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1,1-dichloropropyl, 2,2-dichloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, heptachloropropyl, 1-chloropropan-2-yl, 2-chloropropan-2-yl, 1,1-dichloropropan-2-yl, 1,2-dichloropropan-2-yl, 1,3-dichloropropan-2-yl, 1,2,3-trichloropropan-2-yl, 1,1,3,3-tetrachloropropan-2-yl, 1,1,1,3,3,3-hexachloropropan-2-yl, heptachloropropan-2-yl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromopropan-2-yl, 2-bromopropan-2-yl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodopropan-2-yl, 2-iodopropan-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl butyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluorobutan-2-yl, 4,4,4-trifluorobutan-2-yl, 3,3,4,4,4-pentafluorobutan-2-yl, nonafluorobutan-2-yl, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichlorobutyl, 4,4,4-trichlorobutyl butyl, nonachlorobutyl, 1,1,1-trichlorobutan-2-yl, 4,4,4-trichlorobutan-2-yl, nonachlorobutan-2-yl, 1-bromobutyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl , 5-fluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5-trichloropentyl, 4,4,5,5,5-pentachloropentyl, 3,3,4,4,5,5,5-heptachloropentyl, 2,2,3,3,4,4,5,5,5-nonachloropentyl, undecachloropentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4,5,5,6,6,6- Examples of groups include heptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, 5-iodohexyl, and 6-iodohexyl.

[0043] In the present invention, "C ３ ~C ６ Unless otherwise specified, the term "cycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0044] In the present invention, "C ３ ~C ６Unless otherwise specified, the term "halocycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 11 identical or different halogen atoms, and examples thereof include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-diiodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclobutyl, Pentyl, 3,3-difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl, 2,2-dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl Examples of groups include cyclohexyl, 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3,3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4-dibromocyclohexyl, 3,3-diiodocyclohexyl, 4,4-diiodocyclohexyl, and perfluorocyclohexyl.

[0045] In the present invention, "cyano C ３ ~C ６ Unless otherwise specified, the term "cycloalkyl group" refers to a cyano group. ３ ~C ６A group in which a cycloalkyl group is substituted at any position, i.e., (cyano)-(C ３ ~C ６ cycloalkyl)-group, in which the cycloalkyl moiety is as defined above, and examples thereof include 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-cyanocyclopentyl, 3-cyanocyclopentyl, 1-cyanocyclohexyl, and 4-cyanocyclohexyl groups.

[0046] In the present invention, unless otherwise specified, the term "heterocyclyl group" refers to a non-aromatic heterocycle having a monocyclic or fused bicyclic ring structure containing 5 to 12 ring atoms, and containing, in addition to carbon atoms, one or more heteroatoms selected from oxygen atoms, sulfur atoms, or nitrogen atoms as ring members. Examples of monocyclic heterocycles include isoxazolinyl, piperidinyl, piperazinyl, azetidinyl, aziridinyl, morpholinyl, tetrahydropyranyl, tetrahydrofuryl, oxetanyl, oxiranyl, dioxanyl (e.g., 1,3-dioxanyl, 1,4-dioxanyl, etc.), dioxolanyl (e.g., 1,3-dioxolanyl, etc.), thianyl, tetrahydrothienyl, thietanyl, and thiiranyl groups. Specific examples of bicyclic heterocycles include indolinyl, isoindolinyl, chromanyl, isochromanyl, tetrahydroisoquinolinyl, benzotetrahydrofuryl, benzotetrahydrothienyl, and isobenzotetrahydrothienyl. Examples of such groups include hydrofuryl, isobenzotetrahydrothienyl, benzodioxolyl, dihydrobenzisoxazinyl, dihydrobenzisothiazinyl, 1-oxidetetrahydroquinolinyl, tetrahydroquinolinyl, dihydroquinolinyl, dihydroquinolinonyl, dihydroisoquinolinonyl, dihydrocoumarinyl, dihydroisocoumarinyl, isoindolinonyl, benzodioxanyl, benzoxazolinonyl, quinolizidinyl, indolizidinyl, tropanyl, nortropanyl, quinuclidinyl, 3-azabicyclo[3.1.0]hexanyl, and 6-oxa-3-azabicyclo[3.1.0]hexanyl.

[0047] When the heteroatom of the above-mentioned "heterocyclyl group" is a nitrogen atom, the nitrogen atom may be an N-oxide.

[0048] Here, the substitution position is not particularly limited. That is, the heterocyclyl group includes all its positional isomers. For example, when the heterocyclyl group is a piperidinyl group, the piperidinyl group includes a 1-piperidinyl group, a 2-piperidinyl group, a 3-piperidinyl group, and a 4-piperidinyl group.

[0049] 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, 1-naphthyl, and 2-naphthyl groups.

[0050] In the present invention, unless otherwise specified, the term "heteroaryl group" refers to an aromatic heterocycle having a monocyclic or fused bicyclic ring structure containing 5 to 12 ring atoms and containing, in addition to carbon atoms, one or more heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms as ring members. Examples of monocyclic heterocycles include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, thienyl, furanyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazolyl, thiadiazolyl, oxadiazolyl, and tetrazolyl groups, and a C-type heterocycle formed by combining one of these monocyclic heterocycle groups with a phenyl ring, or by combining any of these monocyclic heterocycle groups with a C-type heterocycle. ８ ~C １０ Fused bicyclic moieties formed by condensing to form a bicyclic group include groups such as indolyl, benzimidazolyl, indazolyl, benzotriazolyl, isoquinolinyl, quinolinyl, benzothiazolyl, benzofuranyl, benzothienyl, benzisoxazolyl, pyrazolopyridyl, quinazolinyl, quinoxalinyl, or cinnolinyl, and the like.

[0051] Here, the substitution position is not particularly limited. That is, the heteroaryl group includes all positional isomers thereof. For example, when the heteroaryl group is a pyridyl group, the pyridyl group includes a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.

[0052] In the present invention, "C ７ ~C １４ Unless otherwise specified, the term "aralkyl group" refers to an alkyl group having 7 to 14 carbon atoms substituted at any position with an aryl group, i.e., (C ６ ~C １２ aryl)-(C １ ~C ２ alkyl)-group, in which the aryl moiety is as defined above, and C １ ~C ２ The alkyl moiety represents a methyl group or an ethyl group, and examples thereof include benzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, naphthalen-1-ylmethyl, naphthalen-2-ylmethyl, etc. An aralkyl group is also called an arylalkyl group.

[0053] In the present invention, unless otherwise specified, the term "heteroaralkyl group" refers to an alkyl group having 6 to 14 carbon atoms substituted at any position with a heteroaryl group, i.e., (heteroaryl)-(C １ ~C ２ alkyl)- group, in which the heteroaryl moiety is as defined above, and C １ ~C ２ The alkyl moiety represents a methyl group or an ethyl group, for example, C ５ ~C １２ Heteroaryl Group C １ ~C ２ Examples of the alkyl group include C. ６ ~C １４ Specific examples of heteroaralkyl groups include pyridylmethyl, pyridylethyl, indolylmethyl, furylmethyl, thienylmethyl, and pyrrolylmethyl groups.

[0054] In the present invention, "C １ ~C ６Unless 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, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, and n-hexyloxy groups.

[0055] 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 ６alkenyl)-O- group, and examples thereof include vinyloxy, 1-propenyloxy, isopropenyloxy, 2-propenyloxy, 1-butenyloxy, 1-methyl-1-propenyloxy, 2-butenyloxy, 1-methyl-2-propenyloxy, 3-butenyloxy, 2-methyl-1-propenyloxy, 2-methyl-2-propenyloxy, 1,3-butadienyloxy, 1-pentenyloxy, 1-ethyl-2-propenyloxy, 2-pentenyloxy, 1-methyl-1-butenyloxy, 3-pent ...2-methyl-2-propenyloxy, 1,3-butadienyloxy, 1-pentenyloxy, 1-ethyl-2-propenyloxy, 2-pentenyloxy, 1-methyl-1-butenyloxy, 3-pentenyloxy, 2-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1,3-butadienyl thenyloxy, 1-methyl-2-butenyloxy, 4-pentenyloxy, 1-methyl-3-butenyloxy, 3-methyl-1-butenyloxy, 1,2-dimethyl-2-propenyloxy, 1,1-dimethyl-2-propenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1,2-dimethyl-1-propenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1,3-pentadienyloxy, 1-vinyl-2-propenyloxy, 1-hexenyloxy oxy, 1-propyl-2-propenyloxy, 2-hexenyloxy, 1-methyl-1-pentenyloxy, 1-ethyl-2-butenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-4-pentenyloxy, 1-ethyl-3-butenyloxy, 1-(isobutyl)vinyloxy, 1-ethyl-1-methyl-2-propenyloxy, 1-ethyl-2-methyl-2-propenyloxy, 1-(isopropyl)-2-propenyloxy, 2-methyl-2-pentenyloxy oxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1,3-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy, 1,5-hexadienyloxy, 1-vinyl-3-butenyloxy, and 2,4-hexadienyloxy groups can be mentioned.

[0056] In the present invention, "C ２ ~C ６Unless otherwise specified, the alkynyl moiety of the "alkynyloxy group" has the above meaning (C ２ ~C ６ alkynyl)-O- group, for example, ethynyloxy, 1-propynyloxy, 2-propynyloxy, 1-butynyloxy, 1-methyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-pentynyloxy, 1-ethyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 1-methyl-2-butynyloxy, 4-pentynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-hexynyloxy, 1-(n-propyl)-2-propynyl oxy, 2-hexynyloxy, 1-ethyl-2-butynyloxy, 3-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy, 4-methyl-1-pentynyloxy, 3-methyl-1-pentynyloxy, 5-hexynyloxy, 1-ethyl-3-butynyloxy, 1-ethyl-1-methyl-2-propynyloxy, 1-(isopropyl)-2-propynyloxy, 1,1-dimethyl-2-butynyloxy, or 2,2-dimethyl-3-butynyloxy groups.

[0057] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkoxy group has the same meaning as defined above (C １ ~C ６haloalkyl)-O- group, and examples thereof include difluoromethoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 1,2-dichloroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, oxy, 2-bromo-2-chloroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy, 1-chloropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bromo-1-methylethoxy, 3-iodopropoxy, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trifluoro-2-propoxy, 3,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy fluoropropoxy, 2,2-difluoropropoxy, 3,3-dichloro-3-fluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethoxy, 1,1,2,3,3,3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4 -chlorobutoxy, 2-chloro-1,1-dimethylethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2-bromo-1,1-dimethylethoxy, 2,2-dichloro-1,1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy, 3,3,3-trifluoro-1-methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 2,3,4-trichlorobutoxy, 2,2,2-trichloro-1,1-dimethylethoxy, 4-chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4-difluorobutoxy, 2,4-dibromo-4,4-difluorobutoxy, 3,4-dichloro-3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy, 4-bromo-3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro-3,4,4-trifluorobutoxy, 2,2,3,3,4,4-hexafluorobutoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2 , 2,2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3,3-trifluoro-2-trifluoromethylpropoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 3,3,4,4,4-pentafluoro-2-butoxy, 2,3,3,3-tetrafluoro-2-trifluoromethylpropoxy, 1,1,2,2,3,3,4,4-octafluorobutoxy, nonafluorobutoxy, perfluoro-tert-butoxy, 4-chloro-1,1,2,2 , 3,3,4,4-octafluorobutoxy, 5,5,5-trifluoropentoxy, 4,4,5,5,5-pentafluoropentoxy, 3,3,4,4,5,5,5-heptafluoropentoxy, 3,3,4,4,5,5,5-heptafluoro-2-pentoxy, 2,2,3,3,4,4,5,5,5-nonafluoropentoxy, 2,2,3,3,4,4,5,5-octafluoropentoxy, perfluoropentoxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2, Examples of groups include 2-bis(trifluoromethyl)propoxy, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxy, 3,3,4,4,5,5,6,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,6-heptafluorohexyloxy, 2,2,3,3,4,4,5,5,6,6-decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis(trifluoromethyl)butyloxy, and perfluorohexyloxy.

[0058] In the present invention, "C ３ ~C ６ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkyloxy group" has the above meaning (C ３ ~C６ cycloalkyl)-O- group, and examples thereof include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy groups.

[0059] In the present invention, "C ６ ~C １２ Unless otherwise specified, the term "aryloxy group" refers to an aryloxy group (C ６ ~C １２ aryl)-O- group, and examples thereof include phenoxy, naphthalen-1-yloxy, and naphthalen-2-yloxy groups.

[0060] In the present invention, unless otherwise specified, the term "heteroaryloxy group" refers to a (heteroaryl)-O- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include pyridyloxy, pyrimidyloxy, pyrazinyloxy, pyridazinyloxy, thienyloxy, and indolyloxy groups.

[0061] In the present invention, "C ７ ~C １４ Unless otherwise specified, the aralkyl moiety of the "aralkyloxy group" has the above meaning (C ７ ~C １４ aralkyl)-O- group, and examples thereof include benzyloxy, 1-phenylethyloxy, 2-phenylethyloxy, 3-phenylpropyloxy, 4-phenylbutyloxy, naphthalen-1-ylmethyloxy, and naphthalen-2-ylmethyloxy groups.

[0062] In the present invention, unless otherwise specified, the term "heteroaralkyloxy group" refers to a (heteroaralkyl)-O- group in which the heteroaralkyl moiety has the above-mentioned meaning, and examples thereof include pyridylmethyloxy, pyridylethyloxy, indolylmethyloxy, furylmethyloxy, thienylmethyloxy, and pyrrolylmethyloxy.

[0063] In the present invention, unless otherwise specified, the term "pentahalosulfanyl group" refers to a λ group substituted with five identical or different halogen atoms. ６-sulfanyl group, and examples thereof include chlorotetrafluorosulfanyl, bromotetrafluorosulfanyl, and pentafluorosulfanyl groups.

[0064] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylthio group" has the above meaning (C １ ~C ６ alkyl)-S- group, and examples thereof include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, and hexylthio groups.

[0065] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfinyl group" has the above meaning (C １ ~C ６ alkyl)-S(═O)— group, and examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl, hexylsulfinyl and the like.

[0066] 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, tert-butylsulfonyl, pentylsulfonyl, and hexylsulfonyl groups.

[0067] In the present invention, "C １ ~C ６Unless otherwise specified, the haloalkyl moiety of the "haloalkylthio group" has the same meaning as defined above (C １ ~C ６ haloalkyl)-S- group, and examples thereof include fluoromethylthio, difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio, and 4,4,4-trifluorobutylthio.

[0068] 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 difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl, and heptafluoro-2-propylsulfinyl groups.

[0069] 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 difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, heptafluoro-2-propylsulfonyl, and nonafluorobutylsulfonyl groups.

[0070] In the present invention, "C ３ ~C ６ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylthio group" has the above meaning (C ３ ~C ６ cycloalkyl)-S- group, and examples thereof include cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, and the like.

[0071] In the present invention, "C ３ ~C ６ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfinyl group" has the above meaning (C ３ ~C ６ cycloalkyl)-S(=O)- group, and examples thereof include cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, and the like.

[0072] In the present invention, "C ３ ~C ６ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfonyl group" has the above meaning (C ３ ~C ６ cycloalkyl)-S(=O) ２ - group, and examples thereof include cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, and cyclohexylsulfonyl groups.

[0073] In the present invention, "C ３ ~C ６ Unless otherwise specified, the halocycloalkylthio group has the same meaning as defined above (C ３ ~C６ halocycloalkyl)-S- group, and examples thereof include 2,2-difluorocyclopropylthio, 2,2-dichlorocyclopropylthio, 3,3-difluorocyclobutylthio, 3,3-dichlorocyclobutylthio, 3-fluorocyclopentylthio, 3,3-difluorocyclopentylthio, nonafluorocyclopentylthio, 3,3-dichlorocyclopentylthio, 4,4-difluorocyclohexylthio, and 4,4-dichlorocyclohexylthio groups.

[0074] In the present invention, "C ３ ~C ６ Unless otherwise specified, the halocycloalkylsulfinyl group has the same meaning as defined above (C ３ ~C ６ halocycloalkyl)-S(═O)— group, and examples thereof include 2,2-difluorocyclopropylsulfinyl, 2,2-dichlorocyclopropylsulfinyl, 3,3-difluorocyclobutylsulfinyl, 3,3-dichlorocyclobutylsulfinyl, 3-fluorocyclopentylsulfinyl, 3,3-difluorocyclopentylsulfinyl, nonafluorocyclopentylsulfinyl, 3,3-dichlorocyclopentylsulfinyl, 4,4-difluorocyclohexylsulfinyl, 4,4-dichlorocyclohexylsulfinyl, and the like.

[0075] In the present invention, "C ３ ~C ６ Unless otherwise specified, the halocycloalkylsulfonyl group refers to a group in which the halocycloalkyl moiety has the same meaning as defined above (C ３ ~C ６ halocycloalkyl)-S(=O) ２- group, and examples thereof include 2,2-difluorocyclopropylsulfonyl, 2,2-dichlorocyclopropylsulfonyl, 3,3-difluorocyclobutylsulfonyl, 3,3-dichlorocyclobutylsulfonyl, 3-fluorocyclopentylsulfonyl, 3,3-difluorocyclopentylsulfonyl, nonafluorocyclopentylsulfonyl, 3,3-dichlorocyclopentylsulfonyl, 4,4-difluorocyclohexylsulfonyl, and 4,4-dichlorocyclohexylsulfonyl groups.

[0076] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylthio group" has the above meaning (C ６ ~C １２ aryl)-S- group, and examples thereof include phenylthio, 1-naphthylthio, and 2-naphthylthio groups.

[0077] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylsulfinyl group" has the above meaning (C ６ ~C １２ aryl)-S(=O)- group, and examples thereof include phenylsulfinyl, 1-naphthylsulfinyl, and 2-naphthylsulfinyl groups.

[0078] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylsulfonyl group" has the above meaning (C ６ ~C １２ aryl)-S(=O) ２ - group, and examples thereof include phenylsulfonyl, 1-naphthylsulfonyl, and 2-naphthylsulfonyl groups.

[0079] In the present invention, unless otherwise specified, the term "heteroarylthio group" refers to a (heteroaryl)-S- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include pyridin-2-ylthio, pyridin-3-ylthio, pyridin-4-ylthio, pyrazin-2-ylthio, pyridazin-3-ylthio, pyridazin-4-ylthio, pyrimidin-2-ylthio, pyrimidin-4-ylthio, pyrimidin-5-ylthio, thiazol-2-ylthio, thiazol-4-ylthio, and thiazol-5-ylthio.

[0080] In the present invention, unless otherwise specified, the term "heteroarylsulfinyl group" refers to a (heteroaryl)-S(═O)- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include pyridin-2-ylsulfinyl, pyridin-3-ylsulfinyl, pyridin-4-ylsulfinyl, pyrazin-2-ylsulfinyl, pyridazin-3-ylsulfinyl, pyridazin-4-ylsulfinyl, pyrimidin-2-ylsulfinyl, pyrimidin-4-ylsulfinyl, pyrimidin-5-ylsulfinyl, thiazol-2-ylsulfinyl, thiazol-4-ylsulfinyl, thiazol-5-ylsulfinyl and the like.

[0081] In the present invention, unless otherwise specified, the "heteroarylsulfonyl group" refers to a (heteroaryl)-S(=O) group in which the heteroaryl moiety has the above meaning. ２ - group, and examples thereof include pyridin-2-ylsulfonyl, pyridin-3-ylsulfonyl, pyridin-4-ylsulfonyl, pyrazin-2-ylsulfonyl, pyridazin-3-ylsulfonyl, pyridazin-4-ylsulfonyl, pyrimidin-2-ylsulfonyl, pyrimidin-4-ylsulfonyl, pyrimidin-5-ylsulfonyl, thiazol-2-ylsulfonyl, thiazol-4-ylsulfonyl, and thiazol-5-ylsulfonyl groups.

[0082] In the present invention, the term "formyl group" refers to an H-C(=O)- group.

[0083] In the present invention, the term "carboxyl group" refers to a HO-C(=O)- group.

[0084] In the present invention, the term "aminocarbonyl group" refers to a ２ It represents an N—C(═O)— group.

[0085] 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, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, and n-hexyloxycarbonyl.

[0086] 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, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, sec-butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1-ethylpropylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, and neopentylcarbonyl.

[0087] In the present invention, the term "formylthio group" refers to an H-C(=O)-S- group.

[0088] In the present invention, the term "aminothiocarbonyl group" refers to a group ２ It represents an N—C(═S)— group.

[0089] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonylthio group" has the above meaning (C １ ~C ６ alkyl)-C(=O)-S- group, and examples thereof include methylcarbonylthio, ethylcarbonylthio, isopropylcarbonylthio, and tert-butylcarbonylthio groups.

[0090] In the present invention, "mono(C １ ~C ６ Unless otherwise specified, the alkyl portion of the "amino group" is defined as above (C １ ~C ６ alkyl)-NH- group, and examples thereof include methylamino, ethylamino, isopropylamino, n-propylamino, and tert-butylamino groups.

[0091] In the present invention, "di(C １ ~C ６ Unless otherwise specified, the alkyl portion of the "amino group" is defined as above (C １ ~C ６ alkyl) ２ It represents an N-group, and the two alkyl groups may be different from each other, and examples thereof include dimethylamino, methylethylamino, and methyl-n-propylamino groups.

[0092] In the present invention, "(di(C １ ~C ６ The term "(C alkyl)sulfinylidene)amino group" refers to a (C １ ~C ６ alkyl) ２ It represents an S(=O)=N- group, and the two alkyl groups may be different from each other. Examples include (S,S-dimethylsulfinylidene)amino, (S,S-diethylsulfinylidene)amino, and (S-ethyl-S-methylsulfinylidene)amino.

[0093] In the present invention, "mono(C １ ~C ６ Unless otherwise specified, the alkyl portion of the "aminocarbonyl group" is defined as above (C １ ~C ６ alkyl)-NH-C(=O)- group, and examples thereof include methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, and tert-butylaminocarbonyl groups.

[0094] In the present invention, "di(C １ ~C ６ Unless otherwise specified, the alkyl portion of the "aminocarbonyl group" is defined as above (C １ ~C ６ alkyl) ２ It represents an N—C(═O)— group, and the two alkyl groups may be different from each other. Examples include dimethylaminocarbonyl, diethylaminocarbonyl, and diisopropylaminocarbonyl groups.

[0095] In the present invention, "R ５ The expression "may be substituted with one or more substituents selected from the group consisting of R ５ and the substituted R ５ The number of carbon atoms or nitrogen atoms in the corresponding substituent is arbitrarily selected within the range of the number of carbon atoms or nitrogen atoms specified. ５ When there are two or more R ５ may be the same as or different from each other.

[0096] In the present invention, "nitrogen atom is R ６ The notation "may be substituted with one or more substituents selected from the group consisting of R ６ represents being substituted by R ６ When there are two R ６ may be the same as or different from each other.

[0097] In the present invention, "R ６ The expression "may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which it is bonded" means that a heterocyclic structure may be formed including the nitrogen atom to which it is bonded, and examples thereof include the formation of piperidinyl, piperazinyl, azetidinyl, aziridinyl, and morpholinyl.

[0098] In the present invention, "R ７ The notation "may be substituted with one or more substituents selected from the group consisting of R ７ and the substituted R ７ The number of R in the corresponding substituent is arbitrarily selected within the range of the number of carbon atoms specified for each. ５ When there are two or more R ５ may be the same as or different from each other.

[0099] In the present invention, "A １ When is a nitrogen atom, A ３ indicates an oxygen atom or a sulfur atom" is １ is a nitrogen atom and A ３ is a combination of oxygen atoms or A １ is a nitrogen atom and A ３ indicates that either of the sulfur atom combinations is

[0100] In the present invention, "A ３ When is a nitrogen atom, A １ indicates an oxygen atom or a sulfur atom" is ３ is a nitrogen atom and A １ is a combination of oxygen atoms or A ３ is a nitrogen atom and A １ indicates that either of the sulfur atom combinations is

[0101] In the present invention, the salt is more specifically an agriculturally acceptable salt, and when a hydroxyl group, a carboxyl group, an amino group, a nitrogen atom of a pyridine ring, or the like is present in the structure of the compound of the present invention represented by general formula [I], this salt is a salt formed of the compound with a metal or an organic base, or a salt formed of a mineral acid or an organic acid. Examples of the metal include alkali metals such as sodium and potassium, and alkaline earth metals such as magnesium and calcium. Examples of the organic base include triethylamine and diisopropylamine. Examples of the mineral acid include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, and sulfuric acid. Examples of the organic acid include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid, and trifluoromethanesulfonic acid.

[0102] Next, representative examples of compounds included in the azolyloxy heterocyclic compound of the present invention represented by general formula [I] are shown in Tables 1 to 70. However, the compounds included in the azolyloxy heterocyclic compound of the present invention are not limited to these. The compound numbers in the tables will be referred to in the following description.

[0103] The compounds encompassed by the azolyloxy heterocyclic compounds of the present invention may exist as geometric isomers of the E- and Z-forms depending on the type of substituent, and the present invention encompasses mixtures containing these E- and Z-forms in any ratio. Furthermore, the compounds encompassed by the present invention may exist as optical isomers due to the presence of one or more asymmetric carbon atoms and sulfur atoms, and the present invention encompasses all optically active forms, racemates, and diastereomers.

[0104] Examples of compounds that are intermediates in the production of the azolyloxyheterocyclic compounds of the present invention represented by general formulas [VI] and [IX] are shown in Tables 71 to 73. The compounds included in the intermediates in the production of the azolyloxyheterocyclic compounds of the present invention (compounds represented by general formula [I] or salts thereof) are not limited to these compounds. The compound numbers in the tables will be referred to in the following description.

[0105] The following symbols in the tables in this specification represent the corresponding groups, for example, as shown below. Me: methyl, Et: ethyl, Pr: normal propyl, Bu: normal butyl, Pen: normal pentyl, Hex: normal hexyl, Nonyl: normal nonyl, iPr: isopropyl, iBu: isobutyl, sBu: secondary butyl, tBu: tertiary butyl, cPr: cyclopropyl, cBu: cyclobutyl, cPen: cyclopentyl, cHex: cyclohexyl, Bn: benzyl, Ph: phenyl, Py: pyridyl, (1-CN)cPr: 1-cyanocyclopropan-1-yl, (2,2-F ２ ) cPr: 2,2-difluorocyclopropan-1-yl, (4-CF ３ ) Ph: 4-(trifluoromethyl)phenyl, (3-Cl)2-Py: 3-chloropyridin-2-yl

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[0178]

[0179] <Production Method> 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]," "a compound represented by formula [I]," and "compound [I]" mean the same compound.

[0180] <Production Method 1> Of the compounds of the present invention, the compound represented by the general formula [I] can be produced, for example, according to the following method.

[0181]

[0182] (In the formula, X, R １ , R ２ , R３ , A １ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0183] That is, the compound represented by general formula [I] can be produced by reacting a compound represented by general formula [II] (compound [II]) with a compound represented by general formula [III] (compound [III]) in a suitable solvent in the presence or absence of a suitable base.

[0184] The amount of compound [III] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of compound [II].

[0185] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected from the range of 0 to 100 moles per mole of compound [II], and is preferably 0.1 to 20 moles.

[0186] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per mole of compound [II].

[0187] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10 moles of metal or metal salt per mole of compound [II], and is preferably 0.01 to 5 moles.

[0188] 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 0°C to 180°C.

[0189] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0190] After the reaction is complete, the reaction mixture is poured into water or concentrated, 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, distillation, etc., as needed.

[0191] <Production Method 2> Of the compounds of the present invention, the compound represented by the general formula [I] can be produced, for example, according to the following method.

[0192]

[0193] (In the formula, X, R １ , R ２ , R ３ , A １ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0194] That is, the compound represented by general formula [I] can be produced by reacting a compound represented by general formula [IV] (compound [IV]) with a compound represented by general formula [V] (compound [V]) in a suitable solvent in the presence or absence of a suitable base.

[0195] The amount of compound [V] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of compound [IV].

[0196] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected from the range of 0 to 100 moles per mole of compound [IV], preferably 0.1 to 20 moles.

[0197] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of compound [IV].

[0198] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be selected appropriately from the range of 0.001 to 10 moles of metal or metal salt per mole of compound [IV], and is preferably 0.01 to 5 moles.

[0199] 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 0°C to 180°C.

[0200] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0201] 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, distillation, etc., as necessary.

[0202] <Production Method 3> Among the compounds of the present invention, the compound represented by the general formula [I-1] can also be produced, for example, according to the following method.

[0203]

[0204] (Wherein R is C １ ~C ６ Alkyl group, C １ ~C ６ represents a haloalkyl group, Y' represents O or S, and X and R １ , R ２ , R ３ , A １ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0205] That is, the compound represented by the general formula [I-1] can be produced by reacting a compound represented by the general formula [VI] (compound [VI]) with compound [VII] or compound [VIII] in an appropriate solvent in the presence or absence of an appropriate base or an appropriate acid.

[0206] The amount of the compound [VII] or compound [VIII] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [VI].

[0207] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected from the range of 0 to 100 moles per mole of compound [VI], preferably 0.1 to 20 moles.

[0208] When an acid is used in this reaction, examples of the acid that can be used include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc., carboxylic acids such as acetic acid or trifluoroacetic acid, sulfonic acids such as methanesulfonic acid or trifluoromethanesulfonic acid, etc. The amount of the acid to be used may be appropriately selected from the range of 0 to 100 mol, preferably 0.1 to 20 mol, per 1 mol of compound [VI].

[0209] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of compound [VI].

[0210] 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 0°C to 180°C.

[0211] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0212] After the reaction is complete, the reaction mixture is poured into water or concentrated, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [I-1]. The isolated compound [I-1] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0213] <Production Method 4> Among the compounds of the present invention, the compound represented by the general formula [I-2] can also be produced, for example, according to the following method.

[0214]

[0215] (In the formula, R, X, Y', R １ , R ２ , R ３ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0216] That is, the compound represented by the general formula [I-2] can be produced by reacting a compound represented by the general formula [IX] (compound [IX]) with compound [VII] or compound [VIII] in an appropriate solvent in the presence or absence of an appropriate base or an appropriate acid.

[0217] The amount of the compound [VII] or compound [VIII] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [IX].

[0218] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected within the range of 0 to 100 moles, preferably 0.1 to 20 moles, per mole of compound [IX].

[0219] When an acid is used in this reaction, examples of the acid that can be used include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc., carboxylic acids such as acetic acid or trifluoroacetic acid, sulfonic acids such as methanesulfonic acid or trifluoromethanesulfonic acid, etc. The amount of the acid used may be appropriately selected in the range of 0 to 100 mol, preferably 0.1 to 20 mol, per 1 mol of compound [IX].

[0220] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve, etc.; esters such as ethyl acetate, isopropyl acetate, butyl acetate, ethyl propionate, etc.; ketones such as acetone, methyl ethyl ketone, etc.; nitriles such as acetonitrile, propionitrile, etc.; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane, etc.; pyridines such as pyridine, picoline, lutidine, etc.; tertiary amines such as triethylamine, tributylamine, etc.; water or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of compound [IX].

[0221] 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 0°C to 180°C.

[0222] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0223] After the reaction is complete, the reaction mixture is poured into water or concentrated, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [I-2]. The isolated compound [I-2] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0224] <Production Method 5> Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, according to the following method.

[0225]

[0226] (In the formula, X, R １ , R ２ , R ３ , A １ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0227] That is, the compound represented by the general formula [I-1] (compound [I-1]) can be produced by reacting a compound represented by the general formula [X] (compound [X]) with a compound represented by the general formula [XI] (compound [XI]) in a suitable solvent in the presence or absence of a suitable base to obtain a compound represented by the general formula [XII], and then cyclizing the compound in a suitable solvent in the presence or absence of a suitable base.

[0228] The amount of the compound [XI] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [X].

[0229] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected within the range of 0 to 100 mol, preferably 0.1 to 20 mol, per 1 mol of the compound [X] or compound [XII].

[0230] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10 moles, preferably 0.01 to 5 moles, of the metal or metal salt per mole of the compound [X] or [XII].

[0231] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per mole of compound [X] or compound [XII].

[0232] 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 0°C to 180°C.

[0233] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0234] 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-1]. The isolated compound [I-1] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0235] <Production Method 6> Among the compounds of the present invention, the compound represented by the general formula [I-2] can be produced, for example, according to the following method.

[0236]

[0237] (In the formula, X, R １ , R ２ , R ３ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0238] That is, the compound represented by the general formula [I-2] (compound [I-2]) can be produced by reacting a compound represented by the general formula [XIII] (compound [XIII]) with a compound represented by the general formula [XIV] (compound [XIV]) in a suitable solvent in the presence or absence of a suitable base to obtain a compound represented by the general formula [XV], and then cyclizing the compound in a suitable solvent in the presence or absence of a suitable base.

[0239] The amount of the compound [XIV] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [XIII].

[0240] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected within the range of 0 to 100 mol, preferably 0.1 to 20 mol, per 1 mol of the compound [XIII] or compound [XV].

[0241] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10 moles, preferably 0.01 to 5 moles, of the metal or metal salt per mole of the compound [XIII] or compound [XV].

[0242] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of Compound [XIII] or Compound [XV].

[0243] 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 0°C to 180°C.

[0244] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0245] 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-2]. The isolated compound [I-2] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0246] <Production Method 7> Among the compounds of the present invention, the compound represented by the general formula [I-3] can be produced, for example, according to the following method.

[0247]

[0248] (In the formula, R ２ａ is R ２ Among them, C １ ~C ６ Alkyl group (the C １ ~C ６ The alkyl group is R ７ substituents), C ２ ~C ６ Alkenyl group (C ２ ~C ６ The alkenyl group is R ７ substituents), C ２ ~C ６ Alkynyl group (C ２ ~C ６ The alkynyl group is R ７ substituents), C ３ ~C ６ Cycloalkyl group (the C ３ ~C ６ The cycloalkyl group is R ７ substituents), a heterocyclyl group (the heterocyclyl group is ５ substituents), C ６ ~C １２ Aryl group (the C ６ ~C １２ The aryl group is R ５ substituents), a heteroaryl group (a heteroaryl group is a ５ substituents), C ７ ~C １４ Aralkyl group (said C ７ ~C １４ The aralkyl group is R ５ Y represents NH, O, or S; Y′, R１ , R ３ , A １ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0249] That is, the compound represented by the general formula [I-3] (compound [I-3]) can be produced by reacting the compound represented by the general formula [XVI] with the compound [XVII] or compound [XVIII] in an appropriate solvent in the presence or absence of an appropriate base.

[0250] The amount of the compound [XVII] or compound [XVIII] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [XVI].

[0251] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected within the range of 0 to 100 moles, preferably 0.1 to 20 moles, per mole of compound [XVI].

[0252] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10 moles, preferably 0.01 to 5 moles, of the metal or metal salt per mole of compound [XVI].

[0253] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of compound [XVI].

[0254] 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 0°C to 180°C.

[0255] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0256] 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-3]. The isolated compound [I-3] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0257] <Production Method 8> Among the compounds of the present invention, the compound represented by the general formula [I-4] can be produced, for example, according to the following method.

[0258]

[0259] (In the formula, R ２ａ , X, Y, R １ , R ３ , A １ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0260] That is, the compound represented by the general formula [I-4] (compound [I-4]) can be produced by reacting the compound represented by the general formula [XIX] with the compound [XX] in an appropriate solvent in the presence or absence of an appropriate base.

[0261] The amount of the compound [XX] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [XIX].

[0262] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected within the range of 0 to 100 mol, preferably 0.1 to 20 mol, per 1 mol of compound [XIX].

[0263] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10 moles, preferably 0.01 to 5 moles, of the metal or metal salt per mole of compound [XIX].

[0264] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per mole of compound [XIX].

[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 0°C to 180°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 72 hours.

[0267] After completion of the reaction, 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-4]. The isolated compound [I-4] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0268] <Production Method 9> Among the compounds of the present invention, the compound represented by the general formula [I-5] can be produced, for example, according to the following method.

[0269]

[0270] (In the formula, R ２ａ , X, Y, R １ , R ３ , A １ , A ３ , A ４ , A ５ , A ６ and A ７ has the same meaning as above.)

[0271] That is, the compound represented by the general formula [I-5] (compound [I-5]) can be produced by reacting the compound represented by the general formula [XXI] (compound [XXI]) with compound [XXII] in an appropriate solvent in the presence or absence of an appropriate base.

[0272] The amount of the compound [XXII] used in this reaction may be appropriately selected usually in the range of 1 to 100 mol, preferably 1 to 20 mol, per 1 mol of the compound [XXI].

[0273] When a base is used in this reaction, examples of the base that can be used include 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 lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc., alkali metal fluorides such as sodium fluoride, potassium fluoride, etc., and inorganic bases such as tripotassium phosphate; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, etc.; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; alkyllithiums such as methyllithium, butyllithium, phenyllithium, etc.; and organic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. The amount of the base used may be appropriately selected within the range of 0 to 100 moles, preferably 0.1 to 20 moles, per mole of compound [XXI].

[0274] This reaction can be carried out in the presence of a catalyst, if necessary. The catalyst comprises a metal or metal salt and a compound as a ligand. Such a catalyst may be prepared in situ from the metal or metal salt and a compound as a ligand, as described below, within the reaction system, or may be prepared outside the reaction system and then introduced into the reaction system. The catalyst may contain components other than the metal, metal salt, and compound as a ligand. Examples of the metal or metal salt include copper compounds such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, and bis(acetylacetonato)copper(II); and palladium compounds such as palladium-carbon, palladium chloride, palladium nitrate, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tetrakis(triphenylphosphine)palladium. Examples of the ligand include ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, triphenylphosphine, tri-tert-butylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and salts thereof. The combination of the metal or metal salt and the ligand may be appropriately selected from the range of 0.1 to 10 moles of the compound as the ligand per mole of the metal or metal salt, and preferably from 1 to 4 moles. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 10 moles, preferably 0.01 to 5 moles, of the metal or metal salt per mole of compound [XXI].

[0275] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, 1,4-dioxane, monoglyme, and diglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-isopropyl ether. Examples of the solvent include aprotic polar solvents such as midazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; esters such as ethyl acetate, isopropyl acetate, butyl acetate, and ethyl propionate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; and a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per mole of compound [XXI].

[0276] 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 0°C to 180°C.

[0277] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0278] After completion of the reaction, 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-5]. The isolated compound [I-5] can be further purified, if necessary, by column chromatography, recrystallization, distillation, etc.

[0279] [Production Intermediates] Compound [II], compound [IV], compound [VI], compound [IX], compound [X], compound [XII], compound [XIII], compound [XV], compound [XVI], compound [XIX], and compound [XXI] in this production method are useful compounds as intermediates in producing the azolyloxy heterocyclic compound represented by general formula [I] of the present invention or a salt thereof.

[0280] In particular, compounds which are intermediates for producing the compound represented by the general formula [I] (azolyloxy heterocyclic compound) or a salt thereof include compounds represented by the general formula [VI]

[0281]

[0282] [In general formula [VI], A １ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ It represents an amino group.

[0283] In addition, compounds which are intermediates for producing the compound represented by the general formula [I] (azolyloxy heterocyclic compound) or a salt thereof include compounds represented by the general formula [IX]

[0284]

[0285] [In general formula [IX], A ３ represents an oxygen atom or a sulfur atom, ４ , A ５ , A６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４ are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ It represents an amino group.

[0286] The compound which is an intermediate for producing the compound represented by the general formula [I] of the present invention or a salt thereof is a compound which is useful as an intermediate for producing the above-mentioned azolyloxy heterocyclic compound represented by the general formula [I] of the present invention or a salt thereof.

[0287] [Herbicide] The herbicide of the present invention contains the azolyloxyheterocyclic compound represented by general formula [I] of the present invention or a salt thereof as an active ingredient. The herbicide of the present invention has excellent herbicidal activity, and some of it exhibits excellent selectivity between useful plants and weeds, making it useful as a pesticide composition, particularly as a herbicide, in agricultural land. That is, the herbicide of the present invention has herbicidal activity against various weeds when applied to upland fields where useful plants are cultivated or non-agricultural fields, such as foliar treatment, soil treatment, seed dressing treatment, soil incorporation treatment, soil treatment before sowing, simultaneous treatment with sowing, soil treatment after sowing, or simultaneous sowing soil cover incorporation treatment.

[0288] The herbicide of the present invention may contain additives (such as carriers) that are commonly used in agricultural chemical formulations, if necessary.

[0289] [Additive Components] 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, antidegradants, 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.

[0290] The additive components will be specifically described below.

[0291] 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.

[0292] 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; and toluene. aromatic hydrocarbons such as C9-C10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, and high-boiling aromatic hydrocarbons; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone; amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, and castor oil, and lower alkyl esters of fatty acids derived from the above vegetable oils; and water.

[0293] Examples of surfactants include nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin 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, acetylene diols, polyoxyalkylene-added acetylene diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine-based surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; alkyl sulfates, polyoxyethylene alkyl anionic surfactants such as 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, 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; and amphoteric surfactants such as betaine-type surfactants such as dialkyldiaminoethyl betaine and alkyldimethylbenzyl betaine, and amino acid-type surfactants such as dialkylaminoethyl glycine and alkyldimethylbenzyl glycine.

[0294] Examples of binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol, polyethylene oxide, and natural phospholipids (e.g., cephalic acid, lecithin, etc.).

[0295] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, and polysaccharides; inorganic fine powders such as high-purity bentonite and white carbon; and organic fine powders such as organic bentonite.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0300] Examples of the anti-caking agent include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, and petroleum resin.

[0301] 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.

[0302] Examples of anti-decomposition agents include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol-based, amine-based, sulfur-based, and phosphoric acid-based; and ultraviolet absorbers such as salicylic acid-based and benzophenone-based.

[0303] Examples of preservatives include potassium sorbate and 1,2-benzthiazolin-3-one.

[0304] Examples of plant fragments include sawdust, coconut husks, corn cobs, tobacco stalks, etc.

[0305] On the other hand, when the herbicide of the present invention contains the above-mentioned additive components, the content ratio thereof is selected from the range of usually 5 to 95%, preferably 20 to 90%, by mass, for carriers such as solid carriers or liquid carriers, usually 0.1 to 30%, preferably 0.5 to 10%, for surfactants, and 0.1 to 30%, preferably 0.5 to 10%, for other additives.

[0306] The herbicide of the present invention can be formulated into any desired dosage form, such as 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 dust, microcapsule formulation, jumbo formulation, Mame-tsubu (registered trademark) formulation, smoking formulation, aerosol formulation, bait formulation, paste formulation, foam formulation, carbon dioxide formulation, paint, wood protective paint, sealant, etc.

[0307] When these formulations are actually used, they can be used as they are or can be diluted to a predetermined concentration with a diluent such as water. The application of various formulations containing the compounds of the present invention or their diluted forms can usually be carried out by commonly used application methods, i.e., spraying (e.g., spraying, misting, atomizing, dusting, granules, water surface application, box application, etc.), soil application (e.g., mixing, irrigation, etc.), surface application (e.g., coating, dusting, covering, etc.), seed treatment (e.g., smearing, dusting treatment, etc.), dipping, poison bait, fumigation, etc.

[0308] The herbicide of the present invention can be applied simultaneously or in divided doses to useful plants, or to a place where useful plants are to be grown or are growing, or to non-agricultural land, to control the growth of plants that are undesirable in relation to useful plants or plants that are undesirable in terms of land management, etc.

[0309] The herbicide of the present invention contains the azolyloxyheterocyclic compound represented by the general formula [I] of the present invention or a salt thereof as an active ingredient, and therefore has herbicidal activity against weeds that grow in fields, paddy fields, orchards, lawns, non-agricultural lands, greenhouses, nursery facilities, or plant factories where useful plants having agricultural, horticultural, and industrial uses are cultivated.

[0310] The useful plants may be plants that have been transformed through cultivation by breeding or genetic engineering techniques. These transformed plants are plants to which desired properties have been imparted by breeding or genetic engineering techniques, as described below.

[0311] [Method of using herbicide] In the method of using the herbicide of the present invention, the herbicide of the present invention is used to control weeds on useful plants having agricultural, horticultural, and industrial uses. In other words, the herbicide of the present invention is used to control weeds that grow in areas where useful plants are cultivated, and is applied to agricultural land such as upland fields and paddy fields by methods such as foliar spraying. The "useful plants" and "weeds" are the same as those described below.

[0312] [Pesticide composition] The pesticide composition of the present invention contains the azolyloxy heterocyclic compound of the present invention or a salt thereof as an active ingredient. This pesticide composition can be used by foliar application, soil application, or water surface application, etc. The pesticide composition of the present invention (particularly the herbicide) is used in soil, particularly in agricultural land (cultivation land) such as upland fields or paddy fields where useful plants are cultivated.

[0313] The blending ratio of the active ingredient in the pesticide composition of the present invention is appropriately selected as needed, but in the case of dusts or granules, it is preferably selected from the range of 0.01 to 10% (by weight), preferably 0.05 to 5% (by weight). In the case of emulsifiable concentrates and wettable powders, it is preferably selected from the range of 1 to 50% (by weight), preferably 5 to 30% (by weight). In addition, in the case of flowables, it is preferably selected from the range of 1 to 40% (by weight), preferably 5 to 30% (by weight).

[0314] The application rate of the pesticide composition of the present invention varies depending on the type of compound used, target weeds, occurrence tendency, environmental conditions, and the formulation used. For example, when the pesticide composition of the present invention is used as a herbicide directly, such as in a dust or granule form, the amount of active ingredient is appropriately selected from the range of 1 g to 50 kg, preferably 10 g to 10 kg, per hectare. When used in a liquid form, such as in an emulsifiable concentrate, wettable powder, or flowable formulation, the amount is appropriately selected from the range of 0.1 to 50,000 ppm, preferably 10 to 10,000 ppm.

[0315] Furthermore, the pesticide composition of the present invention may be formulated, mixed or used in combination with the compound of the present invention, depending on the purpose of use, at least one other pesticide active ingredient, for example, other disease control agent ingredients, insecticide ingredients, acaricide ingredients, nematicide ingredients, synergist ingredients, attractant ingredients, repellent ingredients, herbicide ingredients, phytotoxicity safener ingredients, microbial pesticide ingredients, plant growth regulator ingredients, fertilizers, soil conditioners and the like.

[0316] When used in combination with other pesticide active ingredients or fertilizers, formulations of the individual ingredients may be mixed at the time of application. Furthermore, formulations of the individual ingredients may be used sequentially, or may be applied at intervals of several days. When applied at intervals of several days, the intervals may vary depending on the other ingredients used, but may be, for example, about 1 to 40 days.

[0317] When the pesticide composition of the present invention, which is a mixture of at least one compound selected from the azolyloxyheterocyclic compounds represented by the general formula [I] and salts thereof with at least one other pesticidal active ingredient, is applied, the mixing ratio (mass ratio) of these compounds can usually be 100:1 to 1:100, preferably 20:1 to 1:20, and particularly 10:1 to 1:10.

[0318] The blending ratio (mass %) of the active ingredient in the pesticide composition of the present invention is appropriately selected as needed. For example, when forming a dust, dust granule, fine granule, etc., it is appropriately selected from the range of 0.01 to 20%, preferably 0.05 to 10%. When forming a granule, etc., it is appropriately selected from the range of 0.1 to 30%, preferably 0.5 to 20%. When forming a wettable powder, water dispersible granule, etc., it is appropriately selected from the range of 1 to 70%, preferably 5 to 50%. When forming a water-soluble or liquid formulation, it is appropriately selected from the range of 1 to 95%, preferably 10 to 80%. When forming an emulsifiable concentrate, it is appropriately selected from the range of 5 to 90%, preferably 10 to 80%. When forming an oil formulation, it is appropriately selected from the range of 1 to 50%, preferably 5 to 30%. When forming a flowable formulation, it is appropriately selected from the range of 5 to 60%, preferably 10 to 50%. When making emulsions, microemulsions, suspoemulsions, etc., the content should be appropriately selected from the range of 5 to 70%, preferably 10 to 60%. When making tablets, baits, pastes, etc., the content should be appropriately selected from the range of 1 to 80%, preferably 5 to 50%. When making fumigants, etc., the content should be appropriately selected from the range of 0.1 to 50%, preferably 1 to 30%. When making aerosols, etc., the content should be appropriately selected from the range of 0.05 to 20%, preferably 0.1 to 10%.

[0319] These formulations are diluted to an appropriate concentration and then sprayed, or applied directly.

[0320] When the pesticide composition 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.

[0321] It goes without saying that the pesticide composition of the present invention is sufficiently effective when the compound of the present invention is used alone as the active ingredient, but if necessary, it can be mixed or used in combination with other pesticides, for example, insecticides, acaricides, nematicides, synergists, fungicides, antivirals, attractants, herbicides, plant growth regulators, etc. Furthermore, it can be mixed or used in combination with spreaders, other agricultural materials, fertilizers, etc., and in this case, even more excellent effects may be exhibited.

[0322] 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.

[0323] Herbicide compounds or herbicidal active ingredients: ioxynil (including salts with lithium or sodium, etc., or esters of octanoic acid, etc.), aclonifen, acrolein, azafenidin, acifluorfen (including salts with sodium, etc.), azimsulfuron, asulam, 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, 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 thiamid), 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, diethathyl-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, etc., 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 hylazine), terbutryn, terbumeton, tembotrione, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, triclopyr triclopyr), triclopyr-butotyl, triclopyr-triethylammonium, tritosulfuron, 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, napropamide-M, nicosulfuron, lactic 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, bixlozone, picloram (including salts with dichloroammonium, trolamine, etc.), picolinafen, bicyclopyrone, bicyclopyrone, Spiribac-sodium, pinoxaden, bipyrazone, bifenox, piperophos, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron-ethyl furon-ethyl), pyrazolinate (pyrazolynate), bilanafos (bilanafos), pyraflufen (pyraflufen), pyraflufen-ethyl (pyraflufen-ethyl), pyraquinate (pyraquinate), pyridafol (pyridafol), pyrithiobac-sodium salt (pyrithiobac-sodium), pyridate (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 ) (including salts such as sodium, calcium or ammonia), flufenauxilim, flufenacet, flufenazopyr, flufenoximacil, flufenpyr-ethyl, flupropanate (including sodium salt), flupoxame, flumioxazin, flumiclorac-pentyl clorac-pentyl), flumetsulam, fluridone, flurtamone, fluroxypyr (including esters such as butmethyl and meptyl, or salts with sodium, calcium, ammonia, etc.), flurochloridone, pretilachlor, procarbazone (including salts with sodium, etc.), prodiamine, prochlorosulf Prochlorosulfone, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, propisochlor, propyrisulfuron, propham, profluazole,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, trollamine, choline, etc., or esters such as etadyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), mecoprop-P-potassium salt (mecoprop-P-potassium), Mesosulfuron (including esters such as methyl), mesotrione, metazachlor, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam (including salts such as sodium), disodium methanarsonate (DSMA), methiozoline lin), methyldymuron, metoxuron, metosulam, metsulfuron-methyl, metobromuron, metproxybicyclone, metobenzuron, metolachlor, metribuzin, mepiquat chloride chloride), mefenacet, monosulfuron (including methyl, ethyl, 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) (amine, diethylamine, triethanolamine, isopropylamine, dimethylammonium, diolamine, dodecylammonium, heptyl and salts such as ammonium, tetradecylammonium, triethylammonium, tris(2-hydroxypropyl)ammonium, tetradecylamine, choline, sodium or lithium, or esters such as butotyl ester, 2-butoxypropyl ester, 2-ethylhexyl ester, methyl ester, ethyl ester, butyl ester, isobutyl ester, octyl ester, pentyl ester, propyl ester, isoctyl ester, isopropyl ester, meptyl ester, tefuryl ester, 4-(2,4-dichlorophenyl)-2-propanol. 2-Methyl-4-chlorophenoxyacetic acid (MCPA) (including salts such as sodium, dimethylammonium, choline, and sodium or lithium, or esters such as isoctyl ester), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (including salts such as sodium, dimethylammonium, choline, and esters such as 2-ethylhexyl ester, isoctyl ester, ethyl ester), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including sodium salt, ethyl ester, etc.), 4,6-dinitro-O-cresol (DNOC) (including amine or salt such as sodium), 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]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)- 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 (6-(1-fluoro-1-methylethyl)-N4 -(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine) (chemical name, CAS registration number: 1606999-21-6) (WO 2014 / 064094, WO 2015 / 162164), 6-(1-methylcyclobutyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine (6-(1-methylcyclobutyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-tria 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).

[0324] 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- 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol (3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-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.

[0325] Next, examples of known safening compounds that may be used in admixture or combination are given below.

[0326] 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).

[0327] 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.

[0328] Insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, synergistic active ingredients: acrinathrin, azadirachtin, azamethiphos, acinonapyr, azinphos-ethyl, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate acephate), azocyclotin, abamectin, afidopyropene, afoxolaner, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, allethrin [d -cis-trans-isomer, including d-trans-isomer], isazophos, isamidophos, isocarbophos, isoxathion, isocycloceram, isofenphos-methyl, isoflualanum, isoprocarb, isoprocarb, Epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, 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, cyetpyrafen, 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, temephos, Deltamethrin, terbufos, tralomethrin, transfluthrin, triazamate, triazophos, trioxyflanilide, trichlorfon, Trichoderma asperellum, Trichoderma paecilomyces, Trichoderma hartianum harzianum), triflumuron, trifluenfuronate, triflumezopyrim, trimethacarb, tolfenpyrad, naled, nicotine, nicofluprole, nitenpyram, nemadectin, denso virus, novaluron, noviflumuron, paecilomyces lilacinus, Burkholderia Burkholderia cepacia, Burkholderia rinogensis, Verticillium lecanii, Hydroprene,Pasteuria nishizawai, Pasteuria penetrans, Bacillus amyloliquefaciens, Bacillus firmus, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, insect toxins produced by Bacillus thuringiensis, Bacillus thuringiensis subsp. Aizawai (Bacillus thuringiensis subsp. Aizawai), Bacillus thuringiensis subsp. Israelensis (Bacillus thuringiensis subsp. Israelensis), Bacillus thuringiensis subsp. Kurstaki (Bacillus thuringiensis subsp. Kurstaki), Bacillus thuringiensis subsp. Tenebrionis (Bacillus thuringiensis subsp. Tenebrionis), Bacillus popilliae, Bacillus licheniformis (Bacillus 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,Vinylfluthrin, bifenazate, bifenthrin, pyflubumide, piperflanilide, piperonyl butoxide 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, butocarboxim, butoxycarboxim, buprofezin, furathiocarb, prallethrin, fluacrypyrim,Fluazaindolizine, fluazuron, fluensulfone, fluopyram, sodium fluoroacetate, fluxametamide, fluclodiniliprole, flucycloxuron, flucythrinate, fluthrin, fluvalinate [including tau-isomer], flupyradifurone, flupyrazophos ofos), flupirimin, flupiroxystrobin, flufiprole, flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flupentiophenox lupentiofenox, flumetnicum, flumethrin, fluralaner, flurimfen, prothiofos, protrifenbut, flonicamid, propaphos, propargite, prohydrojasmone rojasmon), profenofos, broflanilide, profluthrin, propetamphos, propoxur, flometoquin, bromopropylate, hexathiazox, hexaflumuron, Pacilimyces tenuipes,Paecilomyces fumosoroceus, Paecilomyces lilacinus, heptafluthrin, heptenophos, permethrin, benclothiaz, benzpyrimoxan, bensultap, benzoximate, bendiocarb, benfuracarb, bentioflumin, Pochonia chlamydospria chlamydosporia, Beauveria tenella, Beauveria bassiana, Beauveria brongniartii, 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, methoxyfenozide, methotrin, metofluthrin,Methoprene, metolcarb, mevinphos, meperfluthrin, modoflaner, monocrosporium phymatophagum, monocrotophos, momfluorothrin, Trichoderma harzianum, litlure-A, litlure-B, aluminum phosphide, zinc phosphide phosphine, hydrogen phosphide, lufenuron, rescale, resmethrin, lepimectin, rotenone, cytoplasmic polyhedrosis virus occlusion bodies, 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) (p-phenyl)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-tetradecadinyl 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]-phosphorothioate (DSP), O-ethyl-O-4-(nitrophenyl)phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosen-10-one, ZXI8901 (code number), F4260 (code number).

[0329] Next, examples of known fungicides (fungicidal active ingredients) or disease control compounds that may be mixed or used in combination are given below.

[0330] Fungicidal active ingredient or disease control compound: Agrobacterium radiobacter radiobacter), azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminotipyr, aminopyrifen, ametoctradine, aldimorph, isotianil, isopyrazam, isofetamide, isoflucipram, isoprothiolane iolane), ipconazole, 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, 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, diethofencarb, diclocymet, dichlofluanid, dichlobentiazox, diclomezine, dicloran, dichlorophen, dithianon, diniconazole, diniconazole-M, zineb zineb, 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, seboctylamine, 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 nonyl phenol sulphonate), Paenibacillus polymyxa, Burkholderia cepacia, Burkholderia rinogensis, Bacillus amyloliquefaciens, Bacillus simplex, Bacillus subtilis, Bacillus pumilus, Bacillus mycoides mycoides), Bacillus licheniformis, harpin protein, Variovorax paradoxus, validamycin, valifenalate, Pantoea agglomerans, picarbutrazox, bixafen, picoxystrobin, Pythium oligandrum, pydiflumetofen, Bitertanol, binapacryl,Hinokitiol, non-pathogenic Erwinia carotovora, non-pathogenic Rhizobium vitis, biphenyl, bifemetstrobin, piperalin, hymexazol, pyraoxystrobin, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriophenone yriofenone, pyrisoxazole, pyridaclomethyl, pyrifenox, pyributicarb, pyribencarb, pyrimethanil, pyroquilon, vinclozolin, ferbam, famoxadone, phenazine oxide oxide), fenamidone, phenaminestrobin, fenarimol, pheneptamidoquin, fenoxanil, fenopyramide, ferimzone, fenpiclonil, fenpicoxami fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, folpet, phthalide, Fusarium oxysporum, bupirimate, fuberidazole,Blasticidin-S, furametpyr, furalaxyl, furanic 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, hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, penconazole, pencycuron, benzovindiflupyr, ben Thiazole, 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, cuprous oxide, cupric hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, copper sulfate, UK-2A (code number), dodecylbenzenesulfonic acid bisethylenediamine copper complex salt [II] (DBEDC), triphenyltin acetate (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide (TPTH).

[0331] Next, examples of known biological pesticides that may be used in admixture or combination are given below.

[0332] 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.

[0333] Next, examples of known agricultural materials that may be mixed or used in combination are given below.

[0334] 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 activating materials, soil spreading agents, soil permeability adjusting materials, soil water retention materials, etc., and biostimulants.

[0335] Next, examples of known agricultural fertilizer components that may be mixed or used in combination are listed below. Fertilizers include inorganic fertilizers and organic fertilizers.

[0336] Agricultural fertilizer ingredients: Ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, ammonium urea nitrate, urea, lime nitrogen, potassium nitrate, superphosphate, triple superphosphate, potassium dihydrogen phosphate, potassium chloride, potassium sulfate, potassium carbonate, potassium silicate, potassium phosphite, oil cake, fish meal, rice bran, bat guano, fermented chicken manure.

[0337] The useful plants referred to in the present invention include field crops or paddy field crops, horticultural crops (vegetables and fruit trees), ornamental woody plants (flowering trees and roadside trees), lawn grasses, flowering plants, ornamental plants, medicinal plants, and timber species, and include, but are not limited to, the following:

[0338] Field or paddy crops: corn, rice, wheat, durum wheat, barley, rye, triticale, spelt, club wheat, oats, sorghum, cotton, soybean, alfalfa, peanuts (groundnuts), kidney beans, lima beans, adzuki beans, cowpeas, mung beans, urad beans, scarlet beans, bamboo beans, moth beans, tepary beans, broad beans, peas, chickpeas, lentils, lupin, pigeon peas, buckwheat, sugar beet, rapeseed, canola, sunflower, sugarcane, cassava, yam, oil palm, jatropha curcas, hemp, flax, quinoa, safflower, tea plant, mulberry, tobacco, camelina, teff, guayule, rubber tree, etc.

[0339] Horticultural crops (vegetables): Solanaceae vegetables (eggplant, tomato, bell pepper, chili pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, crown chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Apiaceae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, lavender, etc.), strawberries, sweet potatoes, yams, taro, sesame, etc.

[0340] Horticultural crops (fruit trees): pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, hazelnuts, pistachios, cashews, macadamia nuts, pecans, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, loquats, bananas, coffee, dates, coconuts, oil palms, etc.

[0341] Ornamental woody plants (flowering trees, street trees): ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redbud, liquidamum, sycamore, zelkova, arborvitae, fir, hemlock, juniper, pine, spruce, yew, elm, horse chestnut, coral tree, dogwood, cedar, cypress, croton, Euonymus japonicus, Photinia japonica, etc.

[0342] Lawngrasses: Lawngrasses (Japanese lawngrass, Zoysiagrass, etc.), Bermudagrasses (Japanese dactylon, etc.), bentgrasses (Japanese marshmallow, Japanese marshmallow, Japanese rice marshmallow, etc.), bluegrasses (Japanese longgrass, Poa annua, etc.), fescue species (Japanese fescue, Japanese marshmallow, Japanese marshmallow, etc.), ryegrass (Japanese barley, Ryegrass, etc.), orchardgrass, Timothy grass, etc.

[0343] Flowers and ornamental plants: roses, carnations, chrysanthemums, lisianthus, baby's breath, gerberas, marigolds, salvia, petunias, verbena, tulips, asters, gentians, lilies, pansies, cyclamen, orchids, lily of the valley, lavender, stocks, snapdragons, primulas, poinsettias, gladioli, cattleyas, daisies, verbena, cymbidiums, begonias, etc.

[0344] Medicinal plants: chamomile, licorice, turmeric, ginseng, coptis, peony, poppy, etc.

[0345] Timber: Abies sachalinensis, spruce, pines, cypress, cedar, cypress, eucalyptus, etc.

[0346] Further, the useful plants referred to in the present invention include 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors such as isoxaflutole, acetolactate synthase (ALS) inhibitors such as imazethapyr and thifensulfuron-methyl, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase (ACCace) inhibitors such as sethoxydim, protoporphyrinogen oxidase (PPO) inhibitors such as flumioxazin and epirifenacil, photosystem II inhibitors such as bromoxynil, and herbicides such as dicamba and 2,4-D. Also included are plants that have been conferred tolerance to these herbicides by classical breeding methods, genetic engineering techniques, and genome editing.

[0347] Examples of useful plants that have been made tolerant by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, and these are already on the market under the trade name Clearfield®. Similarly, Cultivance has been developed as a soybean that is resistant to imidazolinone ALS-inhibiting herbicides.

[0348] Similarly, soybeans that have been made resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl through classical breeding methods are available, and are already on the market under the trade name STS soybean. Similarly, sorghum that has been made resistant to sulfonylurea acetolactate synthase (ALS)-inhibiting herbicides through classical breeding methods is already on the market. Similarly, sugar beets that have been made resistant to thiencarbazone-resistant acetolactate synthase (ALS)-inhibiting herbicides through classical breeding methods are already on the market. Examples of useful plants that have been made resistant to acetyl-CoA carboxylase (ACCace) inhibitors, such as trione oxime and aryloxyphenoxypropionic acid herbicides, through classical breeding methods include SR corn and quizalofop-resistant wheat. Useful plants that have been conferred resistance to acetyl-CoA carboxylase (ACCace) inhibitors are described in, for example, Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990). Also, mutant acetyl-CoA carboxylases (ACCace) resistant to acetyl-CoA carboxylase (ACCace) inhibitors have been reported in, for example, Weed Science, Vol. 53, pp. 728-746 (2005). Plants resistant to acetyl-CoA carboxylase inhibitors can be produced by introducing such mutant acetyl-CoA carboxylase genes into plants using genetic engineering techniques, or by introducing a mutation conferring resistance into crop acetyl-CoA carboxylase (ACCace). Furthermore, by introducing a nucleic acid into plant cells that has undergone base substitution mutations, as typified by the chimeraplasty technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285:316-318), and inducing site-specific amino acid substitution mutations in the crop (acetyl-CoA carboxylase (ACCace) / herbicide target) gene, it is possible to create plants that are resistant to acetyl-CoA carboxylase (ACCace) inhibitors / herbicides.

[0349] Examples of useful plants that have been made resistant through genetic engineering include glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet, and alfalfa varieties, which are already sold under the trade names Roundup Ready®, Roundup Ready 2®, Agrisure GT®, and GlyTol®. Similarly, Optimum® GAT is a soybean and corn variety that is resistant to both glyphosate and ALS inhibitors through genetic engineering. Similarly, there are corn, soybean, cotton, and rapeseed varieties that are resistant to glufosinate through genetic engineering, which are already sold under the trade name LibertyLink®. Similarly, bromoxynil-resistant cotton through genetic engineering is already sold under the trade name BXN. Similarly, soybeans that have been engineered to tolerate HPPD inhibitors using genetic engineering technology are already on the market under the trade name Herbicide-tolerant Soybean line as a variety that is resistant to mesotrione and glufosinate, and under trade names such as Credenz® as a variety that is resistant to HPPD inhibitors, glyphosate, and glufosinate. Similarly, corn, soybeans, and cotton that have been engineered to tolerate 2,4-D or ACCase inhibitors using genetic engineering technology are already on the market under trade names such as Enlist®. Similarly, a soybean variety that has been engineered to tolerate 2,4-D, glyphosate, and glufosinate using genetic engineering technology is already on the market under the trade name Enlist E3. Similarly, soybeans that have been engineered to be tolerant to dicamba using genetic engineering techniques are already on the market as varieties that are tolerant to dicamba and glyphosate under trade names such as Roundup Ready 2 Xtend (registered trademark). Similarly, a soybean variety that has been engineered to be tolerant to HPPD inhibitors such as isoxaflutole and is also tolerant to nematodes using genetic engineering techniques has been registered in the United States as GMB151.

[0350] Further plants with engineered herbicide tolerance are widely known, for example alfalfa, apple, barley, eucalyptus, flax, grape, lentil, rapeseed, pea, potato, rice, sugar beet, sunflower, tobacco, tomato weed and wheat that are tolerant to glyphosate (see, e.g., US 5,188,642, US 4,940,835, US 5,633,435, US 5,804,425, US 5,627,061), and bean, cotton, dung that are tolerant to dicamba. peas, potatoes, sunflowers, tomatoes, tobacco, corn, sorghum and sugarcane (see, for example, WO2008 / 051633, US7105724 and US5670454), soybeans, sugar beets, potatoes, tomatoes and tobacco that are resistant to glufosinate (see, for example, US6376754, US5646024, US5561236), cotton, peppers, apples, tomatoes, sunflowers, tobacco, dill that are resistant to 2,4-D, Potato, corn, cucumber, wheat, soybean, sorghum and millet (see, for example, US Pat. No. 6,153,401, US Pat. No. 6,100,446, WO 2005 / 107437WO, US Pat. No. 5,608,147U and US Pat. No. 5,670,454), canola, corn, barnyard grass, barley, cotton, mustard, lettuce, lentil, melon, foxtail millet, oat, corn, potato, onion, which are resistant to ALS-inhibiting herbicides (e.g., sulfonylurea herbicides or imidazolinone herbicides). Rice, rye, sorghum, soybean, sugar beet, sunflower, tobacco, tomato and wheat (see, for example, US 5,013,659, WO 2006 / 060634, US 4,761,373, US 5,304,732, US 6,211,438, US 6,211,439 and US 6,222,100), in particular, rice that is resistant to imidazolinone herbicides is known, and specific mutations in the acetolactate synthase gene (e.g., S653N, S654K, A122T, S653(At)N, S654(At)K,Rice having A122(At)T (see, for example, US 2003 / 0217381 and WO 2005 / 020673), barley, sugarcane, rice, corn, tobacco, and the like, which are resistant to HPPD-inhibiting herbicides (for example, isoxazole herbicides such as isoxaflutole, triketone herbicides such as sulcotrione and mesotrione, and pyrazole herbicides such as pyrazolinate) or diketonitrile decomposition products of isoxaflutole. , soybean, cotton, rapeseed, sugar beet, wheat and potato (see, for example, WO2004 / 055191, WO1996 / 38567, WO1997 / 049816 and US6791014), and wheat, soybean, cotton, sugar beet, rapeseed, rice, corn, sorghum, sugarcane and sugar beet that are tolerant to PPO-inhibiting herbicides (see, for example, US2002 / 0073443, US2008 / 0052798, Pest Management Science, 61, 2005, 277-285).

[0351] Examples of plants that have been conferred herbicide resistance by conventional breeding techniques or genomic breeding techniques include rice "Clearfield® Rice," wheat "Clearfield® Wheat," sunflower "Clearfield® Sunflower," lentils "Clearfield® Lentils," and canola "Clearfield® Canola," which are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr and imazamox; soybean "STS soybean" which is resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl; and corn "SR" which is resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides. corn (also known as "PoastProtected® corn"), sunflower "ExpressSun®" that is tolerant to sulfonylurea herbicides such as tribenuron, rice "Provisia® Rice" that is tolerant to acetyl-CoA carboxylase inhibitors such as quizalofop, canola "Trizine Tolerant Canola" that is tolerant to photosystem II inhibitors, and sorghum "Igrowth®" that is tolerant to imidazolinone herbicides.

[0352] An example of a plant that has been given herbicide tolerance through genome editing technology is the canola "SU Canola (registered trademark)" that has sulfonylurea herbicide tolerance using a rapid breeding technology (Rapid Trait Development System, RTDS (registered trademark)). RTDS (registered trademark) corresponds to oligonucleotide-directed mutagenesis of genome editing technology, and is a technology that can introduce mutations without cleaving the DNA in the plant via Gene Repair Oligonucleotide (GRON), i.e., a chimeric oligonucleotide of DNA and RNA. Another example is corn that has herbicide tolerance and reduced phytic acid content by deleting the endogenous gene IPK1 using zinc finger nuclease (for example, Nature 459, 437-441). 2009), and rice that has been conferred herbicide resistance using CRISPR-Cas9 (see, for example, Rice, 7, 5, 2014).

[0353] An example of a plant that has been given herbicide tolerance through new breeding techniques is soybean, whose scion has been given the properties of a GM rootstock through grafting. Specifically, a soybean scion that has been given glyphosate tolerance using a glyphosate-tolerant Roundup Ready® soybean as a rootstock has been given glyphosate tolerance (see Weed Technology 2013, 27, 412).

[0354] The useful plants also include plants that have been made capable of synthesizing selective toxins known to be present in the genus Bacillus using genetic engineering techniques.

[0355] Examples of insecticidal toxins that can be expressed in such transgenic plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors ribosome-inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0356] Toxins expressed in such genetically modified plants also include hybrid toxins, truncated toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34A, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced using recombinant technology by combining different domains of these proteins in new ways. A known example of a truncated toxin is Cry1Ab, which lacks a portion of its amino acid sequence. Modified toxins have one or more amino acids substituted in the native toxin.

[0357] Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in patent documents such as EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. The toxins contained in these recombinant plants confer resistance to plants, particularly to coleopteran, dipteran, and lepidopteran pests.

[0358] Additionally, transgenic plants containing one or more insecticidal pest resistance genes and expressing one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include YieldGard® (a corn variety expressing the Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin), YieldGard Plus® (a corn variety expressing both the Cry1Ab and Cry3Bb1 toxins), Herculex I® (a corn variety expressing the Cry1Fa2 toxin and phosphinothricin N-acetyltransferase (PAT) to confer tolerance to glufosinate), NuCOTN33B® (a cotton variety expressing the Cry1Ac toxin), Bollgard I® (a corn variety expressing the Cry1Ab toxin), and Bollgard® (a corn variety expressing the Cry1Ab toxin). I)® (cotton variety expressing Cry1Ac toxin), Bollgard II® (cotton variety expressing Cry1Ac and Cry2Ab toxins), VIPCOT® (cotton variety expressing VIP toxin), NewLeaf® (potato variety expressing Cry3A toxin), NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage Examples of suitable Bt11 corn borer (CB) traits include Bt11 Advantage (Bt11 corn borer (CB) trait), Protecta®, Intacta®, and SmartStax®.

[0359] Examples of plants that have been conferred pest resistance using classical breeding methods or genetic engineering include soybeans having the aphid resistance genes Rag1 (Resistance to Aphis glycines 1) or Rag2 (Resistance to Aphis glycines 2), soybeans that are resistant to the soybean cyst nematode (Heterodera glycines), cotton that is resistant to the root-knot nematode (Meloidogyne incognita), Kanto BPH1, a rice variety that is resistant to the brown planthopper, and Fukuminori, a soybean that is resistant to the common cutworm (Spodoptera litura).

[0360] The useful plants also include those that have been conferred resistance to nematodes using classical breeding methods or genetic engineering techniques. For example, a genetic engineering technique that confers nematode resistance is RNA interference technology (RNAi).

[0361] Plants that have been conferred pest resistance using RNAi include corn that is resistant to Lepidoptera pests (e.g., corn borers, corn earworms, cutworms such as black cutworms, and fall armyworms) and Coleoptera pests (corn rootworms), and these are commercially available or under development as SmartStax®, SmartStax® Pro, or Genuity® SmartStax Pro.

[0362] The above useful plants also include those that have been given the ability to produce anti-pathogenic substances with selective action using genetic recombination techniques.

[0363] Examples of antipathogenic substances include PR proteins (PRPs, described in EP-A-0392225); ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors (known examples include virus-produced KP1, KP4, and KP6 toxins); stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, antibiotics having a heterocycle, and substances produced by microorganisms such as protein factors involved in plant disease resistance (called plant disease resistance genes, described in WO 03 / 000906). Such antipathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO 95 / 33818, EP-A-0353191, etc.

[0364] The useful plants also include crops that have been given useful traits, such as improved oilseed oil components or increased amino acid content, using genetic engineering technology. Examples include VISTIVE® (low-linolene soybean with reduced linolenic acid content) and high-lysine (high foil) corn (corn with increased lysine or oil content).

[0365] The useful plants also include crops that have been given useful traits such as drought tolerance using genetic engineering technology, thereby maintaining or increasing yields. Examples include DroughtGard®, AGRISURE ARTESIAN®, OPTIMUM®, and AQUAMAX® (corn with drought tolerance).

[0366] The herbicide of the present invention also has a control effect on the above-exemplified pests that have acquired resistance to existing herbicides. The herbicide 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 breeding, etc.

[0367] In the present invention, the term "plants transformed through cultivation by breeding methods or genetic engineering techniques" includes not only plants imparted with resistance by classical breeding or genetic engineering techniques, but also plants imparted with resistance 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. Examples of the new breeding techniques include genomic breeding techniques and genome editing techniques. Genomic breeding techniques are techniques for improving the efficiency of breeding using genomic information, and include DNA marker (also called genomic marker or gene marker) breeding techniques and genomic selection. For example, DNA marker breeding is a method of selecting progeny carrying a desired gene for a useful trait from a large number of progeny using a DNA marker, which is a DNA sequence that marks the location of the gene on the genome. By analyzing the progeny using DNA markers at the young stage, the method has the advantage of being able to effectively shorten the time required for breeding.

[0368] Genomic selection is a technique that creates a prediction formula from previously obtained phenotypes and genome information, and predicts characteristics from the prediction formula and genome information without evaluating the phenotype, and can contribute to improving the efficiency of breeding. New breeding techniques are a general term for variety improvement (breeding) techniques that combine molecular biological techniques. Examples include cisgenesis / intragenesis, oligonucleotide-directed mutagenesis, RNA-dependent DNA methylation, genome editing, grafting onto GM rootstocks or scions, reverse breeding, agroinfiltration, and seed production technology (SPT). Genome editing technology is a technique that converts genetic information in a sequence-specific manner, and allows for deletion of base sequences, substitution of amino acid sequences, introduction of foreign genes, etc. Examples of such tools include zinc finger nucleases (Zinc-Finger Nucleases, ZFNs), TALEN, CRISPR / Cas9, CRISPER / Cpf1, and Meganuclease, which are capable of sequence-specific cleavage. Furthermore, there are sequence-specific genome modification technologies such as CAS9 nickase and Target-AID, which are created by modifying the aforementioned tools.

[0369] Furthermore, stacked varieties that combine multiple of the above-mentioned classical herbicide traits or useful traits such as herbicide resistance genes, insecticide pest resistance genes, antipathogenic substance production genes, oilseed component modifications, amino acid content enhancement traits, and drought tolerance traits are also included.

[0370] Non-agricultural land as a setting for using the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) refers to non-agricultural land where it is necessary to control the growth of weeds, such as embankment slopes, riverbeds, road shoulders and slopes, railway beds, park green spaces, sports fields, parking lots, airports, industrial facility sites such as factories and storage facilities, fallow land, or unused land in urban areas, or orchards, pastures, lawns, forestry land, rivers, waterways, canals, reservoirs, etc.

[0371] As described above, the herbicide and pesticide composition of the present invention (a concept that includes herbicides) have herbicidal activity against various weeds. Examples of such weeds are listed below, but the present invention is not limited to these examples.

[0372] Urticaceae weeds: dwarf nettle (Urtica urens).

[0373] Polygonaceae weeds: Polygonum convolvulus, Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Polygonum longisetum, Polygonum aviculare, Polygonum arenastrum, Polygonum cuspidatum, Rumex japonicus, Rumex longiflorum crispus), Rumex obtusifolius, Rumex acetosa, Rumex acetosella, and Persicaria nepalensis.

[0374] Portulacaceae weeds: Common purslane (Portulaca oleracea).

[0375] Caryophyllaceae weeds: chickweed (Stellaria media), cow chickweed (Stellaria aquatica), earweed (Cerastium holosteoides), Dutch earweed (Cerastium glomeratum), giant clover (Spergula arvensis), silverleaf (Silene gallica), and flea weed (Stellaria alsine).

[0376] Molluginaceae weeds: Mollugo verticillata.

[0377] Amaranthaceae weeds: Amaranthus retroflexus, Amaranthus viridis, Amaranthus lividus, Amaranthus spinosus, Amaranthus hybridus, Amaranthus palmeri, Amaranthus patulus, and waterhemp (Amaranthus tuberculatus = Amaranthus rudis = Amaranthus tamariscinus, American birch (Amaranthus blitoides), grey birch (Amaranthus deflexus), Amaranthus quitensis, Japanese bush birch (Amaranthus spinosus), Alternative weed (Alternanthera philoxeroides), Alternative weed (Alternanthera sessilis), sanguinaria (Alternanthera tenella), burrowing birch (Amaranthus powelii), narrow-leaved birch (Amaranthus rudis), small white birch (Amaranthus albus), Amaranthus patulus, Chenopodium album, Chenopodium ambrosioides, Kochia scoparia, Salsola kali, and Atriplex spp.

[0378] Papaveraceae weeds: Corn poppy (Papaver rhoeas), Corn poppy (Papaver dubium), Argemone mexicana.

[0379] Brassicaceae weeds: wild radish (Raphanus raphanistrum), radish (Raphanus sativus), wild mustard (Sinapis arvensis), shepherd's purse (Capsella bursa-pastoris), common mustard (Brassica juncea), common rape (Brassica napus), brassica rapa (Brassica rapa), dwarf burdock (Descurainia pinnata), burdock root (Rorippa islandica), and Japanese mustard (Rorippa sylvestris), Thlaspi arvense, Myagrum rugosum, Lepidium virginicum, Coronopus didymus, Descuralinia sophia, Rorippa indica, Sisymnrium officinale, Cardamine flexuosa, Nasturtium officinale, and Draba nemorosa.

[0380] Capparaceae weeds: Cleome affinis.

[0381] Leguminous weeds (Fabaceae): Aeschynomene indica, zigzag joint vetch (Aeschynomene enerudis), Aeschynomene denticulata, Aeschynomene rudis, Sesbania exaltata, Cassia obtusifolia, Cassia occidentalis, Desmodium tortuosum, Desmodium ascendens, Desmodium rudis illinoense), white clover (Trifolium repens), kudzu (Pueraria lobata), vetch (Vicia angustifolia), raccoon dogwood (Indigofera hirsuta), Indigofera truxillensis, cowpea (Vigna sinensis), Crotalaria incana, vetch (Vicia sativa), medicago lupulina, annual pea (Vicia hirsuta); striata), Medicago polymorpha.

[0382] Oxalidaceae weeds: wood sorrel (Oxalis corniculata), red wood sorrel (Oxalis strica), Oxalis oxyptera, purple wood sorrel (Oxalis devilis).

[0383] Geraniaceae weeds: American geranium (Geranium carolinense), Dutch geranium (Erodium cicutarium), Dove's Foot Crane's-bill (Geranium molle), Hedgerow Crabe's-bill (Geranium pyrenaicum).

[0384] Euphorbiaceae weeds: Euphorbia helioscopia, Euphorbia maculata, Euphorbia hum istrata, Euphorbia esula, Euphorbia heterophylla, Euphorbia brasiliensis, Acalypha australis, Croton glandulosus, Croton lobed lobatus), Brazilian phyllanthus (Phyllanthus corcovadensis), Ricinus com m m unis, Astraea lobata, Chamaesyce hirta, and false daisy (Chamaesyce hyssopifolia).

[0385] Malvaceae weeds: Abutilon theophrasti, Sida rhombifolia, Sida cordifolia, Sida spinosa, Sida glaziovii, Sida santaremnensis, Sida urens, Hibiscus trionum, Calabash (Anoda cristata), Malvastrum coromandelianum, and Chinese bur (Trium fetta). rhomboidea).

[0386] Onagraceae weeds: Ludwigia epilobioides, Ludwigia octovalvis, Ludwigia decurre, Ludwigia leptocarpa, Oenothera biennis, and Oenothera laciniata.

[0387] Sterculiaceae weeds: Waltheria indica Violaceae weeds: Viola arvensis, wild pansy (Viola tricolor).

[0388] Cucurbitaceae weeds: Sicyos angulatus, wild cucumber (Echinocystis lobata), bitter gourd (Momordica charantia).

[0389] Weeds of the Lythraceae family: Ammannia multiflora, Ammannia auriculata, Ammannia coccinea, Lythrum salicaria, and Rotala indica.

[0390] Elatinaceae weeds: Elatine triandra, California waterwort.

[0391] Umbelliferae weeds (Apiaceae): water dropwort (Oenanthe javanica), wild carrot (Daucus carota), hemlock (Coniummm aculatum), and pine cone weed (Cyclospermum leptophyllum).

[0392] Araliaceae weeds: Hydrocotyle sibthorpioides, Brazilian hydrocotyle (Hydrocotyle ranunculoides).

[0393] Ceratophyllaceae weeds: Ceratophyllum demersum.

[0394] Cabomba baiceae weeds: Cabomba caroliniana.

[0395] Haloragaceae weeds: Myriophyllum aquaticum, Myriophyllum verticillatum, Myriophyllum matogrossense, water milfoils (Myriophyllum spicatum, Myriophyllum heterophyllum), and the like.

[0396] Sapindaceae weeds: Cardiospermum halicacabum.

[0397] Primulaces weeds (Prim ulaceae): Anagallis arvensis.

[0398] Asclepiadaceae weeds: giant milkweed (Asclepias syriaca), honeyvine milkweed (Ampelamus albidus).

[0399] Rubiaceae weeds: Galium aparine, Galium spurium var. echinospermon, Spermacococcus latifolia, Diodella teres, Richardia brasiliensis, and winged phallus buttonweed.

[0400] Convolvulaceae weeds: morning glory (Ipomoea nil), American morning glory (Ipomoea hederacea), round morning glory (Ipomoea purpurea), round American morning glory (Ipomoea hederacea var. integruscula), Japanese morning glory (Ipomoea lacunosa), starry morning glory (Ipomoea triloba), Japanese morning glory (Ipomoea acuminata), Japanese ivy hederifolia, Japanese ivy weed (Ipomoea coccinea), Ipomoea quamoclit, Ipomoea grandifolia, Ipomoea aristolochiafolia, Ipomoea cairica, European bindweed (Convolvulus arvensis), Calystegia hederacea, Calystegia japonica, Ivy bindweed (Merremia hedeacea), Hairy woodrose (Merremia aegypia), Roadside woodrose (Merremia cissoides), morning glory (Jacquemontia tamnifolia).

[0401] Boraginaceae weeds: forget-me-not (Myosotis arvensis), Japanese ragwort (Myosotis arvensis), Japanese dogweed (Lithospermum officinale), Japanese ragwort (Echium plantagineum), and Japanese bluebell (Heliotropium indicum).

[0402] Lamiaceae weeds: Lamium purpureum, Lamium amplexicaule, Leonotis nepetaefolia, Hyptis suaveolens, Hyptis lophanta, Leonurus sibiricus, Stachys arvensis, Leonurus sibiricus, and Marsypianthes chamaedrys.

[0403] Solanaceae weeds: Datura stramonium, Solanum nigrum, Solanum americanum, Solanum ptycanthum, Solanum sarrachoides, Solanum rostratum, Solanum aculeatissimum, Solanum sissym briifolium, Solanum carolinense, Physalis serrata angulata), smooth ground cherry (Physalis subglabrata), and giant cherry (Nicandra physaloides).

[0404] Linderniaceae weeds: Lindernia procumbens, Lindernia dubia, and Lindernia angustifolia.

[0405] Plantaginaceae weeds: Plantago asiatica, Plantago lanceolata, Plantago major, Water chickweed, Limnophila sessiliflora, Dopatrium junceum, Gratiola japonica, Bacopa rotundifolia, Veronica hederaefolia, Veronica persica persica), Veronica arvensis, Veronica anagallis-aquatica, Plantago tomentosa.

[0406] Asteraceae weeds: cocklebur (Xanthum pensylvanicum), giant cocklebur (Xanthum occidentale), bristlebur (Xanthum italicum), sunflower (Helianthus annuus), chamomile (Matricaria chamomilla), chamomile (Matricaria perforata), corn marigold (Chrysanthemum segetum), orchard daisy (Matricaria matricarioides), mugwort (Artemisia princeps), and artemisia vulgaris), Chinese mugwort (Artemisia verlotorum), solidago altissima (Solidago altissima), common dandelion (Taraxacum officinale), Galinsoga ciliata, Galinsoga parviflora, ground daisy (Senecio vulgaris), Senecio brasiliensis, Senecio grisebachii, ragweed (Conyza bonariensis), giant ragweed (Conyza sumatransis), Artemisia canadensis, Ragweed (Ambrosia artemisiifolia), Giant ragweed (Ambrosia trifida), Bidens tripartita, Bidens pilosa, Bidens frondosa, Bidens subalternans, Thorn thistle (Cirsium arvense), Common thistle (Cirsium vulgare), Milk thistle (Silybum marianum), Musk thistle (Carduus nutans), Lactuca serriola, Sonchus oleraceus, Sonchus asper, Beach Creeping Oxeye,Perfoliate blackfoot (Melampodium perfoliatum), Pale bittern (Emilia sonchifolia), Southern bittern (Emilia fosbergii), Shiozaki iris (Tagetes minuta), Paracles (Blainvillea latifolia), Blainvillea dichotoma, Japanese daisy (Tridax procumbens), Yerba porosa (Porophyllum ruderale), Paraguay starburst (Acanthospermum australe), Bristletoe starburst (Acanthospermum hispidum), balloon vine (Cardiosperm um halicacabum), ageratum (Ageratum conyzoides), common boneset (Eupatorium perfoliatum), American hawkweed (Eclipta alba), hollyhock (Erechtites hieracifolia), American everlasting (Gamouchaeta spicata), white buttercup (Gnaphalium spicata), Jaegeria hirta, cornflower (Parthenium hysterophorus), and burdock (Siegesbeckia orientalis), American Japanese snowbell (Soliva sessilis), Eclipta prostrata, Japanese snowbell (Centipeda minima), false chamomile (Anthemis cotula), Siberian fox thistle (Cirsium setosum), Cornflower (Centurea cyanus), Coreopsis lanceolata, Rudbeckia hirta, Rudbeckia laciniata, Rudbeckia laciniata var. hortensis Bailey), Bidens subaltemans, water sunflower (Gymnocoronis spilanthoides),Hypochaeris chilensis, Pluchea sagittalis.

[0407] Alisma ataceae weeds: Sagittaria pygmaea, Sagittaria trifolia, Sagittaria sagittifolia, Sagittaria montevidensis, Sagittaria aginashi, Alisma canaliculatum, Alisma plantago-aquatica.

[0408] Limnocharitaceae weeds: Limnocharis flava.

[0409] Hydrocharitaceae weeds: frogbit (Limnobium spongia), water hyacinth (Hydrilla verticillata), common water nymph (Najas guadalupensis), and giant canadian grass (Egeria densa).

[0410] Araceae weeds: Pistia stratiotes.

[0411] Duckweeds (Lemnaceae): Lemna aokikusa, Spirodela polyrhiza, Wolffia globosa.

[0412] Potamogetonaceae weeds: Potamogeton distinctus, pondweeds (Potamogeton crispus, Potamogeton illinoensis, Stuckenia pectinata, etc.).

[0413] Liliaceae weeds: wild onion (Allium canadense), wild garlic (Allium vineale), and wild nobile (Allium macrostemon).

[0414] Pontederiaceae weeds: water hyacinth (Eichhornia crassipes), American whiteweed (Heteranthera limosa), black water hyacinth (Monochoria korsakowii), whiteweed (Monochoria vaginalis), and Heterandera reniformis.

[0415] Commelinaceae weeds: Commelina communis, Commelina bengharensis, Erect dayflower, Murdannia keisak, Doveweed, Murdannia nudiflora.

[0416] Grass weeds (Poaceae): barnyard grass (Echinochloa crus-galli), barnyard grass (Echinochloa oryzicola), barnyard grass (Echinochloa crus-galli var formosensis), latewater grass (Echinochloa oryzoides), barnyard grass (Echinochloa coronana), gulf cockspur (Echinochloa crus-pavonis), green foxtail (Setaria viridis), foxtail (Setaria faberi), golden foxtail (Setaria glauca), American foxtail (Setaria geniculata), large crabgrass (Digitaria ciliaris), large crabgrass (Digitaria sanguinalis), Jamaican crabgrass (Digitaria horizontalis), large crabgrass (Digitaria insularis), goosegrass (Eleusine indica), annual bluegrass (Poa annua), annual bluegrass (Poa trivialis), longgrass (Poa pratensis), annual foxglove (Alopecurus aequalis), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua), Sorghum halepense, Shattercane, Sorghum vulgare, Sorghum arundinaceum, Swallowgrass, Lolium multiflorum, Lolium perenne, Lolium rigidum, Bromus catharticus, Bromus sterilis, Bromus japonicus, Bromus secalinus, Bromus brome, Bromus tectorum), Hordeum jubatum, Goat wheat (Aegilops cylindrica),Reed canary grass (Phalaris arundinacea), small canary grass (Phalaris minor), silky bentgrass (Apera spica-venti), big-leaf sorghum (Panicum dichotomiflorum), Texas panicum (Panicum texanum), guinea foxglove (Panicum maximum), American millet (Brachiaria platyphylla), ruzigrass (Brachiaria ruziziensis), Alexandergrass (Brachiaria plantaginea), Surinamegrass (Brachiaria decumbens), palisade grass (Brachiaria brisantha), Columbia grass (Brachiaria humidicola), Para grass (Urochloa mutica), Sinkurin moth (Cenchrus echinatus), Dwarf chestnut moth (Cenchrus pauciflorus), Narco barnyard grass (Eriochloa villosa), African sedge grass (Chloris gayana), African sedge grass (Chloris virgata), Eragrostis pilosa, Eragrostis plana, Ruby grass (Rhynchelitolum repens), Sea sedge grass (Dactyloctenium) aegyptium), Taiwan grass (Ischaem um rugosum), Japanese bamboo grass (Isachne globosa), rice (Oryza sativa), American paspalum (Paspalum notatum), Coastal sand paspalum (Paspalum maritimum), Japanese knotweed (Paspalum distichum), kikuyu grass (Pennisetum clandestinum), narrow-leaved grass (Pennisetum setosum), horngrass (Rottboellia cochinchinensis), and Japanese maple (Leptochloa chinensis), Leptochloa fascicularis, Leptochloa panicea,Broom grass (Leptochloa filiformis), Amazon sprangle top (Leptochloa panicoides), reed oak (Leersia japonica), Taiwanese reed oak (Leersia hexandra), Bean weed (Leersia sayuka), Siberian weed (Leersia oryzoides), Duck grass (Glyceria leptorrhiza), Mutsuoregusa (Glyceria acutiflora), Loach (Glyceria maxima), Bush grass (Agrostis gigantea), and Cracked weed (Agrostis stolonifera), Cynodon dactylon, Orchard grass (Dactylis glomerata), Centipede grass (Eremochloa ophiuroides), Tall fescue (Festuca arun dinacea), Tall fescue (Festuca rubra), Imperata cylindrica, Miscanthus sinensis, Switchgrass (Panicum virgatum), Japanese lawn grass (Zoysia japonica), Luziola peruviana, Ruby grass (Melinis repens), Spartina anglica.

[0417] Cyperaceae weeds: Cyperus microiria, Cyperus iria, Cyperus compressus, Cyperus difformis, Cyperus flaccidus, Cyperus globosus, Cyperus nipponics, Cyperus odoratus, Cyperus serotinus, Cyperus nutsedge rotundus, Cyperus esculentus, Kyllinga gracilima, Kyllinga brevifolia, Fimbristylis miliacea, Fimbristylis dichotoma, Eleocharis acicularis, Eleocharis kuroguwai, Schoenoplectiella hotarui, Schoenoplectiella juncoides, Schoenoplectiella juncoides, Schoenoplectiella japonica wallichii), Schoenoplectiella mucronatus, Schoenoplectiella triangulatus, Schoenoplectiella nipponicus, Schoenoplectiella triqueter, Bolboschoenus koshevnikovii, Bolboschoenus fluviatilis, Scirpus tabernaemontani.

[0418] Horsetail weeds (Equisetaceae): Horsetail (Equisetum arvense), Horsetail (Equisetum umpalustre).

[0419] Salviniaceae weeds: Salvinia natans.

[0420] Azollaceae weeds: Azolla japonica, Azollaim bricata, Salvinia natans, Azolla cristata.

[0421] Marsileaceae weeds: Marsilea quadrifolia.

[0422] Ricciaceae weeds: ginkgo duckweed (Ricciocarpus natans).

[0423] Rosaceae weeds: Alchemilla monticola.

[0424] Ranunculaceae weeds: Ranunculus muricatus, Ranunculus sardous.

[0425] Fumaria family weeds (Fumarioideae): Fumaria officinalis.

[0426] Characeae weeds: Chara braunii.

[0427] Eriocaulaceae weeds: Eriocaulon cinereum.

[0428] Zygnemataceae weeds: Spirogyra arcla.

[0429] Others: Filamentous algae (Pithophora, Cladophora), mosses, liverworts, hornworts, cyanobacteria, ferns, suckers of perennial crops (pome fruits, stone fruits, berries, nuts, citrus fruits, hops, grapes, etc.).

[0430] The intraspecific mutations of the above-mentioned weeds are not particularly limited. They also include weeds with reduced sensitivity (also known as "resistance") to certain herbicides (herbicide-resistant weeds). The reduced sensitivity may be due to a mutation in the target site (site mutation) or to factors other than site mutations (non-site mutation). Site mutations include those in the nucleic acid sequence (open reading frame) corresponding to the amino acid sequence of a protein, resulting in an amino acid substitution in the target protein, and those resulting in excessive or reduced expression of the target protein due to mutations such as deletion of a suppressor sequence in the promoter region, amplification of an enhancer sequence, or an increase or decrease in the number of gene copies. Non-site mutations include metabolic enhancement, malabsorption, metabolic insufficiency, and extracellular excretion. Factors that contribute to metabolic enhancement include increased activity of metabolic enzymes such as cytochrome P450 monooxygenase, aryl acylamidase, esterase, and glutathione S-transferase. An example of excretion from the system is transport to the vacuole by ABC transporters.

[0431] Examples of herbicide-resistant weeds (resistant weeds) include resistance to 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors such as glyphosate, resistance to hormone-disrupting herbicides such as 2,4-D and dicamba, resistance to acetolactate synthase (ALS) inhibitors, resistance to acetyl-CoA carboxylase (ACCace) inhibitors, resistance to protoporphyrinogen oxidase (PPO) inhibitors, resistance to auxin-based herbicides, and resistance to 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors. Examples of resistance include resistance to photosystem II inhibitors, resistance to photosystem I electron conversion agents, resistance to carotenoid biosynthesis inhibitors, resistance to glutamine synthetase inhibitors, resistance to phytoene desaturase system (PDS) inhibitors, resistance to fatty acid biosynthesis inhibitors, resistance to very long chain fatty acid elongase (VLCFAE) inhibitors, resistance to auxin transport inhibitors, resistance to dihydropteroic acid (DHP) synthase inhibitors, resistance to cellulose synthase inhibitors, resistance to microtubule polymerase inhibitors, and resistance to mitosis / microtubule formation inhibitors.

[0432] Resistant weeds that are resistant to two or more of the above groups (arbitrarily selected group 2, arbitrarily selected group 3, arbitrarily selected group 4, arbitrarily selected group 5, group 6, group 7, or group 8) (stacked) are also effectively controlled. An example of a stacked resistant weed is waterhemp (Amaranthus tuberculatus = Amaranthus rudis = Amaranthus tamariscinus) that is resistant to all of acetolactate synthase (ALS) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors, photosystem II inhibitors, and 2,4-D, and this weed is also effectively controlled. The stacked weeds may be a combination of active point mutations, a combination of non-active point mutations, or a combination of active and non-active point mutations.

[0433] The herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) can be applied simultaneously or in divided doses to the above-mentioned useful plants (useful plants having agricultural, horticultural, and industrial uses), or to the place where the useful plants are intended to be grown (cultivation land), the place where the useful plants are growing, or non-agricultural land. "Applied simultaneously or in divided doses" means that the herbicide or pesticide composition is applied in one dose or in multiple doses. In this case, weeds may have already grown on the useful plants or the cultivation land of the useful plants, or the application may be before weeds have grown.

[0434] Examples of methods for applying the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) simultaneously or in divided portions to useful plants, or to a place where useful plants are to be grown or where useful plants are growing, or to non-agricultural land include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, seed treatment, and hydroponic solution treatment.

[0435] Examples of foliar treatment include a method of applying the herbicide of the present invention or an agrochemical composition containing the herbicide of the present invention to the surface of foliage, tree trunks, fruits, flowers (including before, during, and after flowering), panicles, or the entire plant.

[0436] Examples of soil treatments include soil spraying, soil incorporation, and soil drenching. Examples of locations for soil treatment include planting holes, rows, areas near the planting holes, areas near the rows, the entire cultivated area, the plant's soil edge, between plants, under the trunk, the main trunk ridge, soil raising, seedling boxes, seedling trays, and seedbeds. Examples of treatment times include before sowing, at the time of sowing, after sowing, the seedling raising period, before planting, at planting, and the growth period after planting. In the above-mentioned soil treatments, the herbicide and pesticide composition of the present invention (a concept that includes herbicides) may be mixed with irrigation liquid, for example, by injection into irrigation equipment (irrigation tubes, irrigation pipes, sprinklers, etc.), mixing into inter-row flooding liquid, or mixing into hydroponic liquid. Alternatively, the irrigation liquid and the active ingredient may be mixed in advance, and treatment may be carried out using the above-mentioned irrigation methods or other appropriate irrigation methods, such as sprinkling or flooding.

[0437] Examples of root treatment include a method of immersing the roots of useful plants in a chemical solution containing the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides), and a method of attaching a solid formulation containing the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) to the roots of useful plants.

[0438] The shower treatment may be, for example, a method in which a diluted solution of the herbicide of the present invention or the pesticide composition of the present invention (which is a concept that includes herbicides) is showered onto the foliage of useful plants.

[0439] Examples of the fumigation treatment include a method in which a diluted solution of the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) is made into a mist and dispersed into the air, and the mist is allowed to adhere to the stems and leaves of useful plants.

[0440] An example of the water surface treatment is a method of spraying a liquid or solid formulation containing the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) onto a flooded paddy field.

[0441] Seed treatment includes, for example, treatment of seeds or vegetative reproductive organs with the herbicide of the present invention and the pesticide composition of the present invention (which is a concept that includes herbicides). The vegetative reproductive organs particularly include seed potatoes.

[0442] Examples of hydroponic solution treatments include methods of mixing or incorporating a chemical solution or solid formulation containing the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) into a hydroponic solution (hydroponic solution mixing treatment, hydroponic solution mixing treatment, etc.).

[0443] The herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) can also be applied by spot treatment. Spot treatment is a concept that is opposite to uniform application of the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides), and refers to a treatment in which the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides) are selectively sprayed at locations where weeds have occurred or where weeds are likely to occur. "Applying to a location" means treating plants or soil where weeds have occurred or where weeds are likely to occur. Furthermore, spot treatment does not only apply when all locations where weeds have occurred or where weeds are likely to occur in a continuous cultivation area are selectively treated. In other words, even if a portion of the cultivation area is treated over an entire area, or even if some locations where weeds have occurred or where weeds are likely to occur are not treated with the herbicide of the present invention and the pesticide composition of the present invention (a concept that includes herbicides), it is still included in spot treatment as long as there are areas in the continuous cultivation area that have been spot-treated.

[0444] [Weed Control Method] The weed control method of the present invention is a method of controlling weeds by applying to weeds an active ingredient amount of the azolyloxy heterocyclic compound of the present invention or a salt thereof (the compound of the present invention represented by general formula [I]).

[0445] In the weed control method of the present invention, the pesticide composition of the present invention (specifically, the herbicide) is applied simultaneously or in divided doses to useful plants having agricultural, horticultural, and industrial uses or to a place where useful plants having agricultural, horticultural, and industrial uses are to be grown or are already growing.

[0446] The location to which the herbicide containing the azolyloxy heterocyclic compound of the present invention or a salt thereof is applied for weed control may be a paddy field, a field, a lawn, an orchard, a non-agricultural land, a greenhouse, a seedling facility, a plant factory, or the like.

[0447] Next, the production 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.

[0448] The melting point, which is a physical property of the compound of the present invention, was measured using a Yanako MP-500V micro melting point measuring device, and the refractive index was measured using an Atago Abbe refractometer. １ H NMR spectra were measured using a JNM-ECZL500R (500 MHz), JNM-ECZL400S (400 MHz), JNM-LA400 (400 MHz), JNM-ECS300 (300 MHz), or JNM-LA300 (300 MHz) manufactured by JEOL Ltd., or a Magritek Spinsolve 80ULTRA (80 MHz) using tetramethylsilane (TMS) as an internal standard.

[0449] Also described are methods for producing intermediates for the compounds of the present invention.

[0450] Example 1: Preparation of 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (Compound number of the present invention: A-0014)

[0451] 1) 1-methyl-5-(2-nitrophenoxy)-3-(trifluoromethyl)-1H-pyrazole

[0452] 2-Fluoronitrobenzene (25.00 g, 177 mmol) was dissolved in N,N-dimethylformamide (200 mL), and 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol (32.3 g, 194 mmol) and potassium carbonate (36.6 g, 265 mmol) were added sequentially, followed by stirring for 6 hours at 100° C. The reaction solution was poured into ice water, and the precipitated solid was collected by filtration, washed with water, and then dried under reduced pressure to obtain 1-methyl-5-(2-nitrophenoxy)-3-(trifluoromethyl)-1H-pyrazole (47.67 g, yield: 94%).

[0453] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 8.07-8.04 (1H, m), 7.69-7.65 (1H, m), 7.42-7.38 (1H, m), 7.32-7.29 (1H, m), 5.85 (1H, s), 3.87 (1H, s)

[0454] 2) 2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline

[0455] 1-Methyl-5-(2-nitrophenoxy)-3-(trifluoromethyl)-1H-pyrazole (47.67 g, 166 mmol) was dissolved in ethanol (400 mL), and hot water (200 mL), iron powder (46.3 g, 829 mmol), and ammonium chloride (4.44 g, 83.0 mmol) were added sequentially, followed by stirring at 80°C for 1 hour. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was washed with hexane and then dried under reduced pressure to give 2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (38.83 g, yield: 91%).

[0456] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 7.06-7.02 (1H, m), 6.94-6.92 (1H, m), 6.85-6.83 (1H, m), 6.75-6.71 (1H, m), 5.78 (1H, s), 3.84 (3H, s), 3.82 (2H, br s)

[0457] 3) 2,4-dibromo-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline

[0458] ​​2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (38.83 g, 151 mmol) was dissolved in chloroform (400 mL), and N-bromosuccinimide (56.4 g, 317 mmol) was added under ice cooling. The mixture was heated to 20°C and stirred for 16 hours. The reaction solution was poured into a saturated aqueous solution of sodium bicarbonate, and an aqueous solution of sodium thiosulfate was added, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2,4-dibromo-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (49.89 g, yield: 80%).

[0459] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 7.44 (1H, d), 6.98 (1H, d), 5.91 (1H, s), 4.31 (2H, br s), 3.82 (3H, s)

[0460] 4) N-(2,4-dibromo-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzamide

[0461] 2,4-Dibromo-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (49.89 g, 120 mmol) was dissolved in chloroform (400 mL), and pyridine (14.5 mL, 180 mmol) and benzoyl chloride (15.3 mL, 132 mmol) were added sequentially under ice cooling. The mixture was heated to 20°C and stirred for 48 hours. The reaction solution was poured into methanol, and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed sequentially with dilute hydrochloric acid, water, and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain N-(2,4-dibromo-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzamide (54.08 g, yield: 87%).

[0462] １ H NMR (400MHz, CDCl​​３ / TMS) δ (ppm): 7.86-7.83 (2H, m), 7.67 (1H, d), 7.61-7.57 (1H, m), 7.52-7.48 (2H, m), 7.39 (1H, br s), 7.18 (1H, d), 5.99 (1H, s), 3.73 (3H, s)

[0463] 5) 6-Bromo-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (Compound number of the present invention: A-0272)

[0464] N-(2,4-Dibromo-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzamide (54.08 g, 104 mmol) was dissolved in monoglyme (500 mL), and copper(I) iodide (992 mg, 5.21 mmol), 1,10-phenanthroline (1.87 g, 10.4 mmol), and cesium carbonate (67.8 g, 208 mmol) were added sequentially, and the mixture was stirred at 100°C for 5 hours. Additional copper(I) iodide (500 mg), 1,10-phenanthroline (1.0 g), and cesium carbonate (20 g) were added sequentially to the reaction solution, and the mixture was further stirred at 90°C for 16 hours. The solvent was evaporated under reduced pressure, and the residue was poured into ice water and extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid, water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 6-bromo-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (31.11 g, yield: 68%).

[0465] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 8.24-8.21 (2H, m), 7.64 (1H, d), 7.58-7.51 (3H, m), 7.16 (1H, d), 6.02 (1H, s), 3.91 (3H, s)

[0466] Melting point: 132-133°C

[0467] ​6) 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (Compound number of the present invention: A-0014)

[0468] 6-Bromo-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (31.11 g, 71.0 mmol) was dissolved in ethyl acetate (300 mL), and ethanol (300 mL), triethylamine (14.8 mL, 105 mmol), and palladium on carbon (loading: 10%, 1.50 g) were added sequentially, followed by stirring at 20°C for 1 hour under a hydrogen atmosphere. The reaction solution was filtered, and the solvent was distilled off under reduced pressure. The precipitated solid was removed by filtration, and the solvent was further distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (24.80 g, yield: 97%).

[0469] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 8.28-8.25 (2H, m), 7.55-7.26 (5H, m), 7.02 (1H, m), 5.97 (1H, s), 3.92 (3H, s)

[0470] Melting point: 84-85℃

[0471] Example 2: Preparation of N-isopropyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxamide (Compound number of the present invention: A-0090)

[0472] 1) 5,5'-[(2-nitro-1,3-phenylene)bis(oxy)]bis[1-methyl-3-(trifluoromethyl)-1H-pyrazole]

[0473] ​2,6-Difluoronitrobenzene (20.0 g, 126 mmol) was dissolved in N,N-dimethylformamide (400 mL), and 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol (45.9 g, 276 mmol) and potassium carbonate (43.4 g, 314 mmol) were added sequentially, followed by stirring at 60°C for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5,5'-[(2-nitro-1,3-phenylene)bis(oxy)]bis[1-methyl-3-(trifluoromethyl)-1H-pyrazole] (36.0 g, yield: 63%).

[0474] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.51 (1H, t), 7.03 (2H, d), 6.13 (2H, s), 3.82 (6H, s)

[0475] 2) 5-[3-(benzyloxy)-2-nitrophenoxy]-1-methyl-3-(trifluoromethyl)-1H-pyrazole

[0476] 5,5'-[(2-nitro-1,3-phenylene)bis(oxy)]bis[1-methyl-3-(trifluoromethyl)-1H-pyrazole] (46.0 g, 102 mmol) was dissolved in N,N-dimethylformamide (400 mL), and under ice-cooling, benzyl alcohol (11.0 g, 102 mmol) and sodium hydride (60% dispersion in mineral oil, 4.89 g, 122 mmol) were added sequentially, followed by stirring at 20°C for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with hexane to give 5-[3-(benzyloxy)-2-nitrophenoxy]-1-methyl-3-(trifluoromethyl)-1H-pyrazole (34.0 g, yield: 85%).

[0477] １ H NMR (300MHz, CDCl ３ ​​ / TMS) δ (ppm): 7.42-7.30 (6H, m), 6.91 (1H, d), 6.72 (1H, d), 6.06 (1H, s), 5.23 (2H, s), 3.78 (3H, s)

[0478] 3) 2-amino-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (Compound of the Invention Number: E-0019)

[0479] 5-[3-(benzyloxy)-2-nitrophenoxy]-1-methyl-3-(trifluoromethyl)-1H-pyrazole (15.0 g, 38.1 mmol) was dissolved in ethanol (200 mL), and ethyl acetate (100 mL) and a suspension of palladium on carbon (loading: 5%, 1.5 g) in ethanol (30 mL) were added sequentially, followed by stirring at 20°C for 10 hours under a hydrogen atmosphere. The reaction solution was filtered, and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with hexane to give 2-amino-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (10.0 g, yield: 96%).

[0480] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 6.65-6.56 (3H, m), 5.81 (1H, s), 3.83 (3H, s), 3.78 (2H, br s)

[0481] 4) Ethyl 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxylate (Compound of the Present Invention Number: A-0089)

[0482] ​2-Amino-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (3.0 g, 11 mmol) was dissolved in pyridine (100 mL), and ethyl chloroglyoxylate (7.5 g, 55 mmol) was added under ice-cooling, followed by stirring at 100°C for 4 hours. The solvent was evaporated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The organic layer was washed successively with an aqueous solution of copper(II) sulfate, water, and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and further washed with hexane to give ethyl 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxylate (2.0 g, yield: 51%).

[0483] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.56-7.48 (2H, m), 7.11-7.08 (1H, m), 5.96 (1H, s), 4.58 (2H, q), 3.88 (3H, s), 1.49 (3H, t)

[0484] Melting point: 110-112°C

[0485] 5) N-isopropyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxamide (Compound of the Present Invention Number: A-0090)

[0486] ​Ethyl 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxylate (500 mg, 1.41 mmol) was dissolved in ethanol (20 mL), and isopropylamine (166 mg, 2.81 mmol) was added. The mixture was stirred in a sealed tube at 120°C for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and further washed with hexane:diisopropyl ether (1:1) to give N-isopropyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxamide (393 mg, yield: 76%).

[0487] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.55-7.43 (2H, m), 7.07-7.04 (2H, m), 5.97 (1H, s), 4.32 (2H, q), 3.88 (3H, s), 1.30 (3H, t)

[0488] Melting point: 130-131°C

[0489] Example 3: Preparation of 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound number of the present invention: A-0001)

[0490] 2-Amino-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (4.0 g, 15 mmol) was dissolved in ethyl orthoformate (20 mL) and stirred under reflux for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and further washed with hexane to give 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (3.1 g, yield: 75%).

[0491] １ ​​H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 8.11 (1H, s), 7.48-7.40 (2H, m), 7.08 (1H, d), 5.89 (1H, s), 3.90 (3H, s)

[0492] Melting point: 85-86°C

[0493] Example 4: Preparation of 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-morpholinobenzoxazole (Compound number of the present invention: A-0087)

[0494] 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (150 mg, 0.53 mmol) was dissolved in acetonitrile (10 mL), and morpholine (55 mg, 0.63 mmol), copper(II) bromide (12 mg, 0.054 mmol), and acetic acid (64 mg, 1.1 mmol) were added sequentially, followed by stirring at 50°C for 16 hours. The reaction solution was filtered through silica gel, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-morpholinobenzoxazole (79 mg, yield: 40%).

[0495] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.14-6.85 (3H, m), 5.85 (1H, s), 3.87 (3H, s), 3.83-3.69 (8H, m)

[0496] Melting point: 88-90°C

[0497] Example 5: Preparation of 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-propoxybenzoxazole (Compound number of the present invention: B-0639)

[0498] 1) 4-(methoxymethoxy)-2-(methylthio)benzoxazole

[0499] ​2-Amino-3-(methoxymethoxy)phenol (described in WO 2023 / 112856, 430 mg, 2.54 mmol) was dissolved in ethanol (20 mL), potassium ethyl xanthate (530 mg, 3.31 mmol) was added, and the mixture was stirred under heating and reflux for 4 hours. The reaction solution was poured into water, and an aqueous citric acid solution was added, followed by extraction with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure to obtain crude 4-(methoxymethoxy)benzoxazole-2-thiol (550 mg).

[0500] The obtained crude 4-(methoxymethoxy)benzoxazole-2-thiol was dissolved in tetrahydrofuran (10 mL), and iodomethane (0.19 mL, 3.05 mmol) and potassium carbonate (455 mg, 3.29 mmol) were added successively, followed by stirring at 20°C for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(methoxymethoxy)-2-(methylthio)benzoxazole (430 mg, yield: 75%).

[0501] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.18-7.10 (2H, m), 7.05-7.02 (1H, m), 5.44 (2H, s), 3.54 (3H, s), 2.77 (3H, s)

[0502] 2) 2-(methylthio)benzoxazol-4-ol

[0503] ​4-(Methoxymethoxy)-2-(methylthio)benzoxazole (430 mg, 1.91 mmol) was dissolved in dichloromethane (20 mL), trifluoroacetic acid (10 mL) was added, and the mixture was stirred at 20°C for 2 hours. The reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed successively with an aqueous sodium hydrogen carbonate solution and an aqueous citric acid solution, and the organic layer was dried over anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-(methylthio)benzoxazol-4-ol (340 mg, yield: 98%).

[0504] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.13 (1H, t), 7.01 (1H, d), 6.82 (1H, d), 6.65 (1H, s), 2.74 (3H, s)

[0505] 3) 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(methylsulfonyl)benzoxazole

[0506] 2-(Methylthio)benzoxazol-4-ol (340 mg, 1.88 mmol) was dissolved in N,N-dimethylformamide (20 mL), and sodium hydride (55% dispersion in mineral oil, 106 mg, 2.43 mmol) and 1-methyl-5-(methylsulfonyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (described in WO 2006 / 099957, 860 mg, 3.75 mmol) were added sequentially, followed by stirring at 90°C for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain crude 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(methylthio)benzoxazole (770 mg).

[0507] ​The resulting crude 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(methylthio)benzoxazole was dissolved in chloroform (20 mL), and 3-chloroperbenzoic acid (35% water, 1.19 g, 4.48 mmol) was added, followed by stirring at 20°C for 4 hours. The reaction solution was poured into saturated aqueous sodium bicarbonate, and aqueous sodium thiosulfate was added, followed by extraction with chloroform. The organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(methylsulfonyl)benzoxazole (570 mg, yield: 84%).

[0508] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 7.66-7.59 (3H, m), 3.97 (3H, s), 3.42 (3H, s)

[0509] 4) 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-propoxybenzoxazole (Compound number of the present invention: B-0639)

[0510] 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(methylsulfonyl)benzoxazole (270 mg, 0.75 mmol) was dissolved in 1-propanol (10 mL), and triethylamine (0.26 mL, 1.85 mmol) was added, followed by stirring for 4 hours at 20° C. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-propoxybenzoxazole (200 mg, yield: 78%).

[0511] １ H NMR (300MHz, CDCl ３ ​​ / TMS) δ (ppm): 7.29-7.16 (3H, m), 4.45 (2H, t), 3.93 (3H, s), 1.85 (2H, sext), 1.03 (3H, t)

[0512] Refractive index n ２０ Ｄ 1.4962

[0513] Example 6: Preparation of 2,6-dimethyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound of the Present Invention Number: A-0296)

[0514] 1) 2-Bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline

[0515] 4-Methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (described in WO 97 / 18196, 1.00 g, 3.68 mmol) was dissolved in dichloromethane (10 mL), bromine (648 mg, 4.05 mmol) was added, and the mixture was stirred at 20°C for 16 hours. The reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (700 mg, yield: 54%).

[0516] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 7.13 (1H, d), 6.67 (1H, d), 5.83 (1H, s), 4.11 (2H, br s), 3.82 (3H, s), 2.21 (3H, s)

[0517] 2) N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)acetamide

[0518] ​2-Bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (400 mg, 1.14 mmol) was dissolved in dichloromethane (10 mL), and triethylamine (0.48 mL, 3.42 mmol) and acetyl chloride (0.16 mL, 2.24 mmol) were added, followed by stirring at 20°C for 16 hours. The reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)acetamide (310 mg, yield: 69%).

[0519] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 7.29 (1H, br s), 6.76 (1H, br s), 6.72 (1H, br s), 5.89 (1H, br s), 3.78 (3H, s), 2.32 (3H, br s), 2.18 (3H, br s)

[0520] 3) 2,6-dimethyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound of the present invention: A-0296)

[0521] ​N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)acetamide (310 mg, 0.79 mmol) was dissolved in monoglyme (20 mL), and copper(I) iodide (7.6 mg, 0.04 mmol), 1,10-phenanthroline (14.4 mg, 0.08 mmol), and cesium carbonate (386 mg, 1.18 mmol) were added sequentially, followed by stirring at 90°C for 16 hours. The reaction solution was poured into water, diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2,6-dimethyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (190 mg, yield: 77%).

[0522] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.16 (1H, s), 6.79 (1H, s), 5.84 (1H, s), 3.87 (3H, s), 2.63 (3H, s), 2.45 (3H, s)

[0523] Melting point: 95-98°C

[0524] Example 7: Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-thiol (Compound number of the present invention: A-0464)

[0525] 1) 2-amino-5-methyl-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (Compound number of the present invention: E-0024)

[0526] ​2,6-Dimethyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (64.17 g, 206 mmol) was dissolved in dioxane (200 mL), and water (85 mL) and sulfuric acid (81.3 mL, 1.53 mol) were added sequentially. The mixture was stirred under reflux for 4 hours. The reaction solution was poured into water, and 25% aqueous sodium hydroxide solution was added. The precipitated salt was removed by filtration. The filtrate was extracted with ethyl acetate, and the organic layer was washed sequentially with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane:diisopropyl ether (3:1) to give 2-amino-5-methyl-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (47.10 g, yield: 80%).

[0527] １ H NMR (500MHz, CDCl ３ / TMS) δ (ppm): 6.47 (1H, d), 6.37 (1H, d), 5.80 (1H, s), 5.26 (1H, br s), 3.82 (3H, s), 3.54 (2H, br s), 2.19 (3H, s)

[0528] Melting point: 153-156°C

[0529] 2) 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-thiol (Compound number of the present invention: A-0464)

[0530] 2-Amino-5-methyl-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (20.00 g, 69.6 mmol) was dissolved in ethanol (200 mL), potassium ethyl xanthate (13.4 g, 83.6 mmol) was added, and the mixture was stirred under reflux for 5 hours. The reaction solution was poured into water, and an aqueous citric acid solution was added. The precipitated solid was collected by filtration, washed successively with water, hexane, and hexane:ethyl acetate (10:1), and then dried under reduced pressure to give 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-thiol (20.15 g, yield: 88%).​

[0531] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.05 (1H, s), 6.79 (1H, s), 5.89 (1H, s), 3.84 (3H, s), 2.42 (3H, s)

[0532] Melting point: 244-246°C

[0533] Example 8: Preparation of 1,2-bis(6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazol-2-yl) disulfide (Compound of the present invention number: A-0498)

[0534] 6-Methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-thiol (1.50 g, 4.56 mmol) was dissolved in tetrahydrofuran (15 mL), and triethylamine (0.46 g, 4.55 mmol) and iodine (0.58 g, 2.29 mmol) were added sequentially, followed by stirring at 50° C. for 1 hour. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1,2-bis(6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazol-2-yl)disulfide (1.22 g, yield: 82%).

[0535] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.20 (2H, s), 6.84 (2H, s), 5.89 (2H, s), 3.85 (6H, s), 2.46 (6H, s)

[0536] Melting point: 117-120°C

[0537] Example 9: Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylthio)benzoxazole (Compound number of the present invention: A-0465)

[0538] ​​6-Methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-thiol (3.08 g, 9.35 mmol) was dissolved in acetonitrile (47 mL), and potassium carbonate (1.55 g, 11.2 mmol) and iodomethane (1.46 g, 10.3 mmol) were added sequentially, followed by stirring at 20°C for 1 hour. The reaction solution was poured into water and extracted with diisopropyl ether. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was washed with hexane to give 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylthio)benzoxazole (3.07 g, yield: 96%).

[0539] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.11 (1H,s), 6.76 (1H,s), 5.90 (1H,s), 3.87 (3H,s), 2.72 (3H,s), 2.43 (3H,s)

[0540] Melting point: 117-118°C

[0541] Example 10: Preparation of 2-(ethylamino)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound number of the present invention: A-0499)

[0542] 6-Methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylthio)benzoxazole (0.40 g, 1.17 mmol) was dissolved in ethylamine (2 mol / L tetrahydrofuran solution, 5.0 mL) and the mixture was stirred for 16 hours at 80° C. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2-(ethylamino)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (0.20 g, yield: 50%).

[0543] １ H NMR (300MHz, CDCl​​３ / TMS) δ (ppm): 6.92 (1H, s), 6.67 (1H, s), 5.83 (1H, s), 4.87 (1H, br s), 3.86 (3H, s), 3.56-3.47 (2H, m), 2.37 (3H, s), 1.29 (3H, t)

[0544] Melting point: 120-123°C

[0545] Example 11: Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(2,2,2-trifluoroethoxy)benzoxazole (Compound of the Present Invention Number: A-0447)

[0546] 1) 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylsulfonyl)benzoxazole

[0547] 6-Methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylthio)benzoxazole (2.0 g, 5.8 mmol) was dissolved in chloroform (100 mL), and 3-chloroperbenzoic acid (35% water content, 3.9 g, 14.7 mmol) was added under ice-cooling. The mixture was heated to 20°C and stirred for 16 hours. The reaction solution was poured into aqueous sodium thiosulfate solution and extracted with chloroform. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with diisopropyl ether to give 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylsulfonyl)benzoxazole (2.0 g, yield: 91%).

[0548] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.33 (1H, s), 6.94 (1H, s), 5.98 (1H, s), 3.87 (3H, s), 3.45 (3H, s), 2.53 (3H, s)

[0549] ​2) 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(2,2,2-trifluoroethoxy)benzoxazole (Compound number of the present invention: A-0447)

[0550] 6-Methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(methylsulfonyl)benzoxazole (380 mg, 1.0 mmol) was dissolved in trifluoroethanol (10 mL), triethylamine (300 mg, 3.0 mmol) was added, and the mixture was stirred at 20°C for 1 hour. The reaction solution was poured into 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-(2,2,2-trifluoroethoxy)benzoxazole (356 mg, yield: 89%).

[0551] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.10 (1H, s), 6.79 (1H, s), 5.86 (1H, s), 4.88 (2H, q), 3.86 (3H, s), 2.43 (3H, s)

[0552] Melting point: 73-74°C

[0553] (Example 12) Preparation of 2-(ethoxy)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound number of the present invention: A-0407)

[0554] ​2-Amino-5-methyl-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (10.0 g, 34.8 mmol) was dissolved in chloroform (300 mL), and tetraethyl orthocarbonate (13.4 g, 69.7 mmol) and acetic acid (8 mL) were added sequentially, followed by stirring at 60°C for 2 hours. The reaction solution was poured into a 1 M aqueous sodium hydroxide solution and extracted with chloroform. The organic layer was washed sequentially with 10% hydrochloric acid, water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2-(ethoxy)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (10.7 g, yield: 90%).

[0555] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.04 (1H, s), 6.73 (1H, s), 5.87 (1H, s), 4.59 (2H, q), 3.86 (3H, s), 2.41 (3H, s), 1.48 (3H, t)

[0556] Melting point: 103-104°C

[0557] (Example 13) Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound of the Present Invention Number: A-0296)

[0558] 2-Amino-5-methyl-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (1.0 g, 3.5 mmol) was dissolved in triethyl orthoformate (5 mL) and stirred under reflux for 4 hours. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (1.0 g, yield: 97%).

[0559] １ H NMR (300MHz, CDCl ３ ​​ / TMS) δ (ppm): 8.03 (1H, s), 7.28 (1H, s), 6.88 (1H, s), 5.88 (1H, s), 3.89 (3H, s), 2.49 (3H, s)

[0560] Melting point: 98-99℃

[0561] (Example 14) Preparation of 2-bromo-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (Compound of the Present Invention Number: A-0557)

[0562] 6-Methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (0.62 g, 2.1 mmol) was dissolved in tetrahydrofuran (7 mL), and n-butyllithium (1.6 mol / L hexane solution, 1.43 mL, 2.3 mmol) was added dropwise at -78°C, followed by stirring at the same temperature for 30 minutes. N-Bromosuccinimide (0.45 g, 2.5 mmol) was added to the reaction solution, and the temperature was raised to 20°C and the mixture was stirred for 30 minutes. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2-bromo-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole (0.63 g, yield: 80%).

[0563] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.21 (1H, s), 6.84 (1H, s), 5.88 (1H, s), 3.87 (3H, s), 2.47 (3H, s)

[0564] Melting point: 95-96°C

[0565] (Example 15) Preparation of N-isopropyl-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxamide (Compound number of the present invention: A-0531)

[0566] ​1) Ethyl 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxylate (Compound number of the present invention: A-0523)

[0567] 2-Amino-5-methyl-3-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenol (25.0 g, 87 mmol) was dissolved in pyridine (300 mL), and ethyl chloroglyoxylate (60.0 g, 439 mmol) was added, followed by stirring at 100°C for 2 hours. The solvent was distilled off under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water, 10% hydrochloric acid, and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give ethyl 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxylate (20.0 g, yield: 62%).

[0568] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.32 (1H, s), 6.88 (1H, s), 5.95 (1H, s), 4.56 (2H, q), 3.87 (3H, s), 2.51 (3H, s), 1.48 (3H, t)

[0569] Melting point: 150-152°C

[0570] 2) N-isopropyl-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxamide (Compound number of the present invention: A-0531)

[0571] ​Ethyl 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxylate (8.0 g, 22 mmol) was dissolved in ethanol (300 mL), and isopropylamine (4.0 g, 68 mmol) was added, followed by stirring at 40°C for 16 hours. Additional isopropylamine (3.5 g) was added to the reaction solution, and the mixture was stirred at 40°C for an additional 8 hours. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was washed with diisopropyl ether to give N-isopropyl-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzoxazole-2-carboxamide (7.7 g, yield: 93%).

[0572] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.31 (1H, s), 7.07 (1H, br d), 6.85 (1H, s), 5.96 (1H, s), 4.36-4.25 (2H, m), 3.87 (3H, s), 2.50 (3H, s), 1.30 (6H, d)

[0573] Melting point: 124-125°C

[0574] (Example 16) Production of 6-fluoro-4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(o-tolyl)benzoxazole (Compound number of the present invention: B-0665)

[0575] 1) 2-bromo-4-fluoro-6-(methoxymethoxy)aniline

[0576] ​4-Fluoro-2-(methoxymethoxy)aniline (described in MedChemComm 2014, 5, 808-815, 21.55 g, 126 mmol) was dissolved in acetonitrile (250 mL), and N-bromosuccinimide (24.7 g, 139 mmol) was added under ice cooling, and the mixture was heated to 20°C and stirred for 1 hour. The reaction solution was poured into an aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-bromo-4-fluoro-6-(methoxymethoxy)aniline (22.45 g, yield: 71%).

[0577] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 6.89-6.81 (2H, m), 5.19 (2H, s), 4.03 (2H, br s), 3.49 (3H, s)

[0578] 2) N-[2-bromo-4-fluoro-6-(methoxymethoxy)phenyl]-2-methylbenzamide

[0579] 2-Bromo-4-fluoro-6-(methoxymethoxy)aniline (2.00 g, 8.0 mmol) was dissolved in chloroform (20 mL), and pyridine (1.3 mL, 16 mmol) and o-toluoyl chloride (1.6 mL, 12 mmol) were added sequentially, followed by stirring at 20°C for 16 hours. The reaction solution was poured into methanol, and the solvent was distilled off under reduced pressure. The residue was dissolved in methanol (20 mL), and potassium carbonate (2.2 g, 16 mmol) was added, followed by stirring under heating and reflux. The reaction solution was poured into water, and extracted with chloroform. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain N-[2-bromo-4-fluoro-6-(methoxymethoxy)phenyl]-2-methylbenzamide (2.34 g, yield: 79%).

[0580] １ H NMR (300MHz, CDCl ３ ​​ / TMS) δ (ppm): 7.63 (1H, br s), 7.39-7.35 (1H, m), 7.29-7.24 (2H, m), 7.07 (1H, dd), 7.00-6.95 (2H, m), 5.20 (2H, s), 3.48 (3H, s), 2.55 (3H, s)

[0581] 3) 6-fluoro-4-(methoxymethoxy)-2-(o-tolyl)benzoxazole

[0582] N-[2-bromo-4-fluoro-6-(methoxymethoxy)phenyl]-2-methylbenzamide (2.34 g, 6.4 mmol) was dissolved in monoglyme (80 mL), and copper(I) iodide (61 mg, 0.32 mmol), 1,10-phenanthroline (114 mg, 0.63 mmol), and cesium carbonate (3.1 g, 9.5 mmol) were added sequentially, followed by stirring at 80°C for 16 hours. The solvent was distilled off under reduced pressure, and the residue was poured into water. The precipitated solid was collected by filtration and washed with water. The residue was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure to obtain 6-fluoro-4-(methoxymethoxy)-2-(o-tolyl)benzoxazole (1.81 g, yield: 99%).

[0583] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 8.16-8.13 (1H, m), 7.43-7.29 (3H, m), 7.01-6.97 (1H, m), 6.90-6.86 (1H, m), 5.54 (2H, s), 3.57 (3H, s), 2.78 (3H, s)

[0584] 4) 6-fluoro-2-(o-tolyl)benzoxazol-4-ol

[0585] ​6-Fluoro-4-(methoxymethoxy)-2-(o-tolyl)benzoxazole (1.81 g, 6.3 mmol) was dissolved in dichloromethane (20 mL), and trifluoroacetic acid (5 mL) was added under ice cooling. The mixture was heated to 20°C and stirred for 16 hours. Additional trifluoroacetic acid (1 mL) was added to the reaction solution, and the mixture was stirred at 20°C for an additional 16 hours. The reaction solution was poured into a saturated aqueous sodium hydrogen carbonate solution, and an aqueous citric acid solution was added. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 6-fluoro-2-(o-tolyl)benzoxazol-4-ol (1.56 g, yield: quantitative).

[0586] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 8.07-8.04 (1H, m), 7.45-7.31 (3H, m), 6.91-6.87 (1H, m), 6.68-6.64 (1H, m), 2.72 (3H, s)

[0587] 5) 6-Fluoro-4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(o-tolyl)benzoxazole (Compound number of the present invention: B-0665)

[0588] 6-Fluoro-2-(o-tolyl)benzoxazol-4-ol (1.56 g, 6.4 mmol) was dissolved in N,N-dimethylformamide (30 mL), and sodium hydride (55% dispersion in mineral oil, 0.36 g, 8.3 mmol) and 1-methyl-5-(methylsulfonyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (7.4 g, 32 mmol) were added sequentially, followed by stirring at 90°C for 3.5 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 6-fluoro-4-{[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]oxy}-2-(o-tolyl)benzoxazole (1.16 g, yield: 46%).

[0589] ​１ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 8.09-8.06 (1H, m), 7.40-7.20 (5H, m), 3.98 (3H, s), 2.61 (3H, s)

[0590] Melting point: 102-104°C

[0591] Example 17: Preparation of 2-(tert-butyl)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}oxazolo[4,5-c]pyridine (Compound of the Present Invention Number: C-0036)

[0592] 1) 4-bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-amine

[0593] 2-Chloro-6-methyl-3-nitropyridine (25.00 g, 145 mmol) was dissolved in tetrahydrofuran (480 mL), and under ice-cooling, sodium hydride (60% dispersion in mineral oil, 5.85 g, 146 mmol) and 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol (24.1 g, 145 mmol) were added, followed by stirring at 50°C for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous ammonium chloride solution and saturated brine, and insoluble matter was removed by filtration. The filtrate was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was washed with diisopropyl ether to obtain crude 6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-3-nitropyridine.

[0594] Crude 6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-3-nitropyridine was dissolved in ethanol (300 mL), palladium on carbon (loading: 10%, 7.68 g) was added, and the mixture was stirred under a hydrogen atmosphere for 16 hours at 20° C. The reaction solution was filtered, and the solvent was distilled off under reduced pressure to obtain crude 6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-amine.​

[0595] Crude 6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-amine was dissolved in tetrahydrofuran (290 mL), and N-bromosuccinimide (25.8 g, 145 mmol) was added under ice-cooling, and the mixture was heated to 20° C. and stirred for 3 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-amine (19.27 g, yield: 38%).

[0596] 2) N-(4-bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-yl)pivalamide

[0597] 4-Bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-amine (18.00 g, 51.3 mmol) was dissolved in dichloromethane (170 mL), and pyridine (4.87 g, 61.6 mmol) and pivaloyl chloride (6.80 g, 56.4 mmol) were added successively under ice-cooling, and the mixture was heated to 20°C and stirred for 16 hours. The solvent was evaporated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and further washed with diisopropyl ether to obtain N-(4-bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-yl)pivalamide (12.38 g, yield: 55%).

[0598] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 7.22 (1H, s), 6.99 (1H, br s), 6.36 (1H, s), 3.76 (3H, s), 2.40 (3H, s), 1.36 (9H, s)

[0599] ​3) 2-(tert-butyl)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}oxazolo[4,5-c]pyridine (Compound of the Present Invention Number: C-0036)

[0600] N-(4-bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-yl)pivalamide (12.38 g, 28.4 mmol) was dissolved in monoglyme (290 mL), and copper(I) iodide (0.27 g, 1.4 mmol), 1,10-phenanthroline (0.51 g, 2.8 mmol), and cesium carbonate (18.5 g, 56.8 mmol) were added successively, followed by stirring at 90° C. for 2 hours. The reaction solution was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2-(tert-butyl)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}oxazolo[4,5-c]pyridine (4.36 g, yield: 43%) and N-(4-bromo-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-3-yl)pivalamide (4.68 g, recovery rate: 39%).

[0601] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.15 (1H, s), 6.39 (1H, s), 3.85 (3H, s), 2.51 (3H, s), 1.51 (9H, s)

[0602] Melting point: 123-125°C

[0603] Example 18: Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-propoxyoxazolo[4,5-c]pyridine (Compound of the Present Invention Number: C-0050)

[0604] 1) 3-amino-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-4-ol (Compound number of the present invention: E-0063) ​

[0605] 2-(tert-butyl)-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}oxazolo[4,5-c]pyridine (4.36 g, 12.3 mmol) was dissolved in dioxane (10 mL), and water (2 mL) and sulfuric acid (3.62 g, 36.9 mmol) were added sequentially, followed by stirring at 100°C for 16 hours. The reaction solution was poured into aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 3-amino-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-4-ol (2.76 g, yield: 78%).

[0606] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 6.40 (1H, s), 6.15 (1H, s), 3.78 (3H, s), 3.65 (2H, br s), 2.25 (3H, s)

[0607] 2) 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-propoxyoxazolo[4,5-c]pyridine (Compound of the Present Invention Number: C-0050)

[0608] 3-Amino-6-methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}pyridin-4-ol (0.45 g, 1.6 mmol) was dissolved in chloroform (4 mL), and tetrapropyl orthocarbonate (0.60 g, 2.4 mmol) and acetic acid (0.29 g, 4.8 mmol) were added sequentially, followed by stirring for 2 hours at 60° C. The reaction solution was purified by silica gel column chromatography to obtain 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-propoxyoxazolo[4,5-c]pyridine (0.12 g, yield: 22%).

[0609] １ H NMR (300MHz, CDCl ３ ​​ / TMS) δ (ppm): 7.05 (1H, s), 6.34 (1H, s), 4.57 (2H, t), 3.84 (3H, s), 2.49 (3H, s), 1.91 (2H, sext), 1.07 (3H, t)

[0610] Melting point: 119-120°C

[0611] (Example 19) Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzothiazole (Compound number of the present invention: C-0230)

[0612] 1) N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzothioamide

[0613] 2-Bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (0.50 g, 1.4 mmol) was dissolved in dichloromethane (10 mL), and pyridine (0.23 mL, 2.8 mmol) and benzoyl chloride (0.20 mL, 1.7 mmol) were added sequentially, followed by stirring at 20°C for 16 hours. The reaction solution was poured into methanol, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain crude N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzamide.

[0614] Crude N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzamide was dissolved in toluene (15 mL), Lawesson's reagent (0.45 g, 1.1 mmol) was added, and the mixture was stirred at 80° C. for 4 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzothioamide (0.61 g, yield: 91%).

[0615] 2) 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzothiazole (Compound number of the present invention: C-0230)

[0616] N-(2-bromo-4-methyl-6-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}phenyl)benzothioamide (0.61 g, 1.3 mmol) was dissolved in monoglyme (20 mL), and copper(I) iodide (12 mg, 0.06 mmol), 1,10-phenanthroline (23 mg, 0.13 mmol), and cesium carbonate (0.63 g, 1.9 mmol) were added sequentially, followed by stirring at 90°C for 16 hours. The reaction solution was purified by silica gel column chromatography to obtain 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzothiazole (0.48 g, yield: 95%).

[0617] １ H NMR (400MHz, CDCl ３ / TMS) δ (ppm): 8.02-8.00 (2H, m), 7.54 (1H, s), 7.49-7.46 (3H, m), 6.96 (1H, s), 5.91 (1H, s), 3.95 (3H, s), 2.49 (3H, s)

[0618] Melting point: 119-120°C

[0619] (Example 20) Preparation of 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-propoxybenzothiazole (Compound of the Present Invention Number: C-0236)

[0620] 1) 2-amino-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzothiazole (Compound number of the present invention: C-0244)

[0621] ​4-Methyl-2-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}aniline (0.22 g, 0.81 mmol) was dissolved in acetic acid (10 mL), potassium thiocyanate (0.32 g, 3.3 mmol) was added, and the mixture was stirred at 20°C for 15 minutes. The reaction solution was cooled to 10°C, bromine (0.043 mL, 0.83 mmol) was added, and the mixture was heated to 20°C and stirred for 16 hours. The reaction solution was filtered, and the filtrate was poured into water, followed by the addition of saturated aqueous sodium bicarbonate solution. The precipitated solid was collected by filtration and washed with water. The residue was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 2-amino-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzothiazole (0.21 g, yield: 79%).

[0622] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.26 (1H, s), 6.78 (1H, s), 5.79 (1H, s), 5.27 (2H, br s), 3.87 (3H, s), 2.38 (3H, s)

[0623] 2) 2-chloro-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzothiazole (Compound number of the present invention: C-0249)

[0624] 2-Amino-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzothiazole (0.21 g, 0.64 mmol) was dissolved in acetonitrile (10 mL), and tert-butyl nitrite (purity: 90%, 0.17 mL, 1.3 mmol) and copper(II) chloride (0.17 g, 1.3 mmol) were added sequentially, followed by stirring at 60°C for 4 hours. The reaction solution was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated brine, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-chloro-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzothiazole (0.22 g, yield: 99%).​

[0625] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.43-7.42 (1H, m), 6.93-6.91 (1H, m), 5.87 (1H, s), 3.89 (3H, s), 2.46 (3H, s)

[0626] 3) 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-propoxybenzothiazole (Compound number of the present invention: C-0236)

[0627] 1-Propanol (0.056 mL, 0.75 mmol) was dissolved in tetrahydrofuran (5 mL), and sodium hydride (55% dispersion in mineral oil, 33 mg, 0.76 mmol) and 2-chloro-6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}benzothiazole (0.22 g, 0.63 mmol) were added sequentially, followed by stirring at 20°C for 16 hours. The reaction solution was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 6-methyl-4-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-propoxybenzothiazole (0.20 g, yield: 85%).

[0628] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 7.29 (1H, s), 6.88 (1H, s), 5.79 (1H, s), 4.41 (2H, t), 3.89 (3H, s), 2.41 (3H, s), 1.80 (2H, sext), 1.00 (3H, t)

[0629] Melting point: 74-75°C

[0630] Example 21: Preparation of 7-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (Compound of the Present Invention Number: D-0011)

[0631] ​​1) N-(2,3-dihydroxyphenyl)benzamide

[0632] 2,3-Dimethoxyaniline (0.71 g, 4.6 mmol) was dissolved in chloroform (10 mL), and pyridine (0.56 mL, 6.9 mmol) and benzoyl chloride (0.64 mL, 5.5 mmol) were added successively, followed by stirring at 20°C for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate, and saturated brine, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain crude N-(2,3-dimethoxyphenyl)benzamide.

[0633] Crude N-(2,3-dimethoxyphenyl)benzamide was dissolved in dichloromethane (80 mL), and boron tribromide (1 mol / L dichloromethane solution, 28 mL, 28 mmol) was added at -78°C. The mixture was then heated to 0°C and stirred for 4 hours. The reaction solution was poured into ice water, and insoluble matter was removed by filtration, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain N-(2,3-dihydroxyphenyl)benzamide (0.68 g, yield: 64%).

[0634] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 9.51 (1H, s), 8.09 (1H, br s), 7.93-7.89 (2H, m), 7.67-7.51 (3H, m), 6.89-6.78 (2H, m), 6.58-6.54 (1H, m), 6.08 (1H, s)

[0635] 2) 2-phenylbenzoxazol-7-ol

[0636] ​N-(2,3-dihydroxyphenyl)benzamide (0.68 g, 3.0 mmol) was dissolved in toluene (30 mL), toluenesulfonic acid monohydrate (0.11 g, 0.58 mmol) was added, and the mixture was stirred under heating and reflux for 20 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-phenylbenzoxazol-7-ol (0.57 g, yield: 91%).

[0637] １ H NMR (300MHz, CDCl ３ / TMS) δ (ppm): 8.27-8.23 (2H, m), 7.56-7.49 (3H, m), 7.38-7.35 (1H, m), 7.25-7.21 (1H, m), 6.93-6.89 (1H, m), 5.85 (1H, br s)

[0638] 3) 7-{[1-methyl-4-nitro-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole

[0639] 2-Phenylbenzoxazol-7-ol (0.57 g, 2.7 mmol) was dissolved in N,N-dimethylformamide (20 mL), and 5-chloro-1-methyl-4-nitro-3-(trifluoromethyl)-1H-pyrazole (0.68 g, 3.0 mmol) and potassium carbonate (0.56 g, 4.1 mmol) were added sequentially, followed by stirring at 60°C for 2 hours. The reaction solution was poured into water, and the precipitated solid was collected by filtration and washed sequentially with water and hexane. The residue was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure to give 7-{[1-methyl-4-nitro-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (1.02 g, yield: 93%).

[0640] １ H NMR (300MHz, CDCl ３ ​​ / TMS) δ (ppm): 8.12-8.08 (2H, m), 7.64-7.61 (1H, m), 7.58-7.50 (3H, m), 7.37-7.32 (1H, m), 7.03-7.00 (1H, m), 3.97 (3H, s)

[0641] 4) 7-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (Compound number of the present invention: D-0011)

[0642] 7-{[1-methyl-4-nitro-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (1.02 g, 2.5 mmol) was dissolved in tetrahydrofuran (20 mL), and ethanol (10 mL), water (10 mL), zinc powder (0.66 g, 10 mmol), and ammonium chloride (0.54 g, 10 mmol) were added sequentially, followed by stirring at 20°C for 2 hours. The reaction solution was filtered, and the filtrate was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain crude 7-{[4-amino-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole.

[0643] The crude 7-{[4-amino-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole was dissolved in N,N-dimethylformamide (20 mL), and tert-butyl nitrite (purity: 90%, 0.60 mL, 4.6 mmol) was added, followed by stirring at 70°C for 6 hours. The reaction solution was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7-{[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}-2-phenylbenzoxazole (0.18 g, yield: 20%).

[0644] １ H NMR (300MHz, CDCl ３ ​ / TMS) δ (ppm): 8.23-8.19 (2H, m), 7.65-7.63 (1H, m), 7.57-7.49 (3H, m), 7.37-7.33 (1H, m), 7.12-7.09 (1H, m), 5.94 (1H, s), 3.94 (3H, s)

[0645] Melting point: 83-86°C

[0646] The physical properties of the compounds [I] of the present invention synthesized in accordance with the above examples, including the values ​​in the above examples, are shown in the following Tables 74 to 92. The compound numbers and symbols in the tables have the same meanings as above.

[0647] The physical properties of the intermediates [VI] and [IX] used in the synthesis of the compound [I] of the present invention, including the values ​​in the above examples, are shown in Tables 93 and 94. The compound numbers and symbols in the tables have the same meanings as those described above.

[0648]

[0649]

[0650]

[0651]

[0652]

[0653]

[0654]

[0655]

[0656]

[0657]

[0658]

[0659]

[0660]

[0661]

[0662]

[0663]

[0664]

[0665]

[0666]

[0667]

[0668]

[0669] Next, specific examples of formulations of the herbicide of the present invention using the azolyloxy heterocyclic compound or its salt of the present invention produced as described above will be explained. However, the types and blending ratios of the compounds and additives are not limited to these examples and can be changed within a wide range. In the following explanation, "parts" means parts by mass.

[0670] (Formulation Example 1) Emulsifiable concentrate Each compound shown in Tables 1 to 70 and 74 to 92 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.

[0671] (Formulation Example 2) Wettable powder Each compound shown in Tables 1 to 70 and 74 to 92 10 parts Naphthalenesulfonic acid formalin condensate sodium salt 0.5 parts Polyoxyethylene alkylaryl ether 0.5 parts Diatomaceous earth 24 parts Clay 65 parts The above ingredients were uniformly mixed and pulverized to give wettable powders.

[0672] (Formulation Example 3) Dust Each compound shown in Tables 1 to 70 and 74 to 92 2 parts Diatomaceous earth 5 parts Clay 93 parts The above ingredients were uniformly mixed and pulverized to give a dust.

[0673] (Formulation Example 4) Granules Each compound shown in Tables 1 to 70 and 74 to 92 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 to 32 mesh granules using an extrusion granulator, and then dried to give granules.

[0674] (Formulation Example 5) Flowable formulation Each compound shown in Tables 1 to 70 and 74 to 92 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.

[0675] (Formulation Example 6) Water Dispersible Granules Each compound shown in Tables 1 to 70 and 74 to 92 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 obtain water dispersible granules.

[0676] Next, the herbicidal activity of the herbicides of the present invention using formulations containing the azolyloxyheterocyclic compounds or salts thereof of the present invention produced as described above as active ingredients will be specifically described. The herbicidal activity in the following Test Examples 1 to 11 was subjectively evaluated on an index scale of 0 to 10, with "0" indicating that the growth or emergence of the test weeds at the time of inspection was equivalent to that of an untreated plot, and "10" indicating that the test weeds were completely dead or completely inhibited from emerging. "Untreated plots" refer to plots that were not treated with the compound of the present invention (no compound of the present invention was added), and the other plots were subjected to the same procedures as those used in the treatment plots using formulations containing the compound of the present invention.

[0677] Regarding the criteria for objective evaluation, an index of 1 to 2 indicates that an effect on the growth or emergence of test weeds is observed compared to the untreated plot, but the degree of the effect is slight, and the herbicidal activity of the compound of the present invention is unclear. An index of 3 to 10 indicates that the growth or emergence of test weeds is significantly worse than that of the untreated plot, and the herbicidal activity of the compound of the present invention is clearly observed.

[0678] [Test Example 1] Herbicidal activity confirmation test against barnyard grass in foliar application: Approximately 340 cm ３Plastic pots were filled with field soil, barnyard grass seeds were sown to a sowing depth of 1 cm, and the plants were cultivated in a greenhouse. After about two weeks, a wettable powder prepared according to Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed on the foliage of the weeds in the pots using a small sprayer. The plants were then continued to grow in the greenhouse, and herbicidal activity was confirmed about 20 days after treatment.

[0679] The compounds that had herbicidal activity of index 3 or more against barnyardgrass when applied to the foliage are as follows: A-0007, A-0009, A-0010, A-0013, A-0014, A-0015, A-0019, A-0021, A-0 022, A-0023, A-0035, A-0039, A-0040, A-0041, A-0042, A-0045, A-0046, A-0047, A-0048, A-0052, A-0055, A-0057, A-0058, A-0062, A-0074, A-0 077, A-0084, A-0086, A-0087, A-0090, A-0091, A-0093, A-0112, A-0159, A-0174, A-0175, A-0176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0 187, A-0188, A-0191, A-0194, A-0195, A-0210, A-0226, A-0241, A-0246, A-0247, A-0251, A-0252, A-0254, A-0272, A-0277, A-0278, A-0283, A-0 295, A-0296, A-0297, A-0298, A-0299, A-0300, A-0301, A-0302, A-0308, A-0309, A-0311, A-0312, A-0313, A-0317, A-0318, A-0319, A-0320, A-0 322, A-0323, A-0324, A-0325, A-0326, A-0327, A-0331, A-0332, A-0333, A-0334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0345, A-0346, A-0 348, A-0349, A-0350, A-0351, A-0352, A-0353, A-0354, A-0355, A-0356, A-0357, A-0358, A-0359, A-0360, A-0361, A-0362, A-0363, A-0364, A-0 366, A-0367, A-0369, A-0370, A-0371, A-0372, A-0373, A-0374, A-0375, A-0376, A-0377, A-0378, A-0379, A-0380, A-0383, A-0384, A-0385, A-0 386, A-0388, A-0389, A-0390, A-0391, A-0393, A-0394, A-0395, A-0397,A-0399、A-0401、A-0402、A-0403、A-0404、A-0405、A-0406、A-0407、A-0408、A-0409、A-0410、A-0411、A-0412、A-0413、A-0419、A-0420、A-0421、A-0422、A-0424、A-0425、A-0426、A-0432、A-0433、A-0434、A-0435、A-0436、A-0437、A-0438、A-0439、A-0441、A-0442、A-0443、A-0446、A-0447、A-0449、A-0450、A-0451、A-0452、A-0453、A-0454、A-0455、A-0464、A-0465、A-0466、A-0467、A-0470、A-0472、A-0473、A-0474、A-0475、A-0476、A-0478、A-0479、A-0480、A-0481、A-0483、A-0484、A-0485、A-0486、A-0487、A-0488、A-0490、A-0491、A-0493、A-0494、A-0496、A-0497、A-0499、A-0500、A-0502、A-0503、A-0504、A-0505、A-0506、A-0508、A-0509、A-0510、A-0514、A-0521、A-0522、A-0524、A-0525、A-0526、A-0527、A-0528、A-0529、A-0530、A-0531、A-0532、A-0533、A-0534、A-0535、A-0536、A-0537、A-0538、A-0539、A-0540、A-0541、A-0542、A-0543、A-0544、A-0545、A-0546、A-0547、A-0548、A-0549、A-0550、A-0552、A-0553、A-0554、A-0571、A-0576、A-0577、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0588、A-0589、A-0605、A-0611、A-0626、A-0627、A-0628、A-0629、A-0640、A-0645、A-0646、A-0672、A-0677、A-0678、A-0688、A-0689、A-0704、A-0710、A-0725、A-0726、A-0729、A-0740、A-0773、A-0778、A-0779, A-0783, A-0784, A-0789, A-0805, A-0810, A-0811, A-0837, A-0842, A-0843, A-0873, A-0889, A-0900, A-0905, A-0906, A-0943, A-0997, B-0006, B-0073, B-0095, B-0107, B-0116, B-0117, B-0120, B -0121, B-0129, B-0130, B-0131, B-0261, B-0323, B-0339, B-0422, B-0485, B-0486, B-0489, B-0490, B- 0491, B-0492, B-0529, B-0530, B-0568, B-0633, B-0643, B-0664, B-0665, B-0670, B-0685, B-0686, B-0 695, B-0702, B-0707, B-0708, B-0709, B-0712, B-0713, B-0714, B-0720, B-0722, B-0723, B-0730, B-07 32, B-0755, B-0756, B-0759, B-0760, B-0884, B-0945, B-0949, B-0976, B-0977, B-0980, B-0981, B-101 1, B-1012, B-1042, B-1043, B-1073, B-1074, C-0043, C-0044, C-0050, C-0230, C-0236, C-0240, C-0395 , C-0396, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0680] [Test Example 2] Herbicidal activity confirmation test against Locust rye in foliar application: Approximately 340 cm ３ Plastic pots were filled with field soil, and Locust seeds were sown to a sowing depth of 1 cm and cultivated in a greenhouse. After about two weeks, a wettable powder prepared according to Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed on the foliage of the weeds in the pots using a small sprayer. Growth was then continued in the greenhouse, and herbicidal activity was confirmed about 20 days after treatment.

[0681] The compounds that had herbicidal activity against Lolium multiflorum with an index of 3 or more when applied to foliage are shown below. A-0009, A-0010, A-0014, A-0015, A-0019, A-0021, A-0022, A-0038, A-0 039, A-0041, A-0045, A-0046, A-0047, A-0048, A-0049, A-0052, A-0055, A-0057, A-0058, A-0062, A-0077, A-0084, A-0086, A-0087, A-0090, A-0 091, A-0093, A-0112, A-0159, A-0174, A-0175, A-0176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0187, A-0188, A-0191, A-0194, A-0195, A-0 210, A-0226, A-0241, A-0246, A-0247, A-0251, A-0252, A-0254, A-0272, A-0277, A-0278, A-0283, A-0293, A-0295, A-0296, A-0297, A-0298, A-0 299, A-0300, A-0301, A-0302, A-0308, A-0309, A-0310, A-0311, A-0312, A-0313, A-0317, A-0319, A-0320, A-0322, A-0323, A-0324, A-0325, A-0 326, A-0327, A-0331, A-0332, A-0333, A-0334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0345, A-0346, A-0348, A-0349, A-0350, A-0351, A-0 352, A-0353, A-0354, A-0355, A-0356, A-0357, A-0358, A-0359, A-0360, A-0361, A-0362, A-0363, A-0365, A-0366, A-0367, A-0369, A-0370, A-0 371, A-0372, A-0373, A-0374, A-0375, A-0376, A-0377, A-0378, A-0379, A-0380, A-0383, A-0384, A-0385, A-0386, A-0388, A-0389, A-0390, A-0 391, A-0392, A-0393, A-0394, A-0395, A-0397, A-0399, A-0401, A-0402,A-0403、A-0404、A-0406、A-0407、A-0408、A-0409、A-0410、A-0411、A-0412、A-0413、A-0419、A-0420、A-0421、A-0422、A-0424、A-0425、A-0426、A-0432、A-0433、A-0434、A-0435、A-0436、A-0437、A-0438、A-0439、A-0441、A-0442、A-0443、A-0446、A-0447、A-0449、A-0450、A-0451、A-0452、A-0453、A-0454、A-0455、A-0464、A-0465、A-0466、A-0467、A-0470、A-0472、A-0473、A-0474、A-0475、A-0476、A-0478、A-0479、A-0480、A-0481、A-0483、A-0484、A-0485、A-0486、A-0487、A-0488、A-0490、A-0491、A-0493、A-0494、A-0496、A-0497、A-0499、A-0500、A-0502、A-0503、A-0504、A-0505、A-0506、A-0508、A-0509、A-0510、A-0514、A-0520、A-0521、A-0522、A-0524、A-0525、A-0526、A-0527、A-0528、A-0529、A-0530、A-0531、A-0532、A-0533、A-0534、A-0535、A-0536、A-0537、A-0538、A-0539、A-0540、A-0541、A-0542、A-0543、A-0544、A-0545、A-0546、A-0547、A-0549、A-0550、A-0552、A-0553、A-0554、A-0571、A-0576、A-0577、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0588、A-0589、A-0605、A-0611、A-0626、A-0627、A-0628、A-0629、A-0640、A-0645、A-0646、A-0651、A-0672、A-0677、A-0678、A-0688、A-0689、A-0704、A-0710、A-0729、A-0740、A-0773、A-0778、A-0779、A-0783、A-0784、A-0789、A-0810、A-0811, A-0837, A-0842, A-0843, A-0868, A-0873, A-0874, A-0889, A-0900, A-0905, A-0906, A- 0930, A-0943, A-0997, B-0006, B-0058, B-0073, B-0095, B-0107, B-0116, B-0117, B-0120, B-012 1, B-0129, B-0130, B-0131, B-0261, B-0323, B-0339, B-0422, B-0485, B-0486, B-0489, B-0490, B-0491, B-0492, B-0529, B-0530, B-0564, B-0568, B-0633, B-0664, B-0665, B-0670, B-0685, B-0 686, B-0695, B-0702, B-0707, B-0708, B-0709, B-0712, B-0713, B-0714, B-0720, B-0722, B-072 3, B-0730, B-0732, B-0755, B-0756, B-0759, B-0760, B-0976, B-0977, B-0980, B-0981, B-1011, B -1012, B-1042, B-1043, B-1074, C-0043, C-0044, C-0050, C-0230, C-0236, C-0240, C-0395, C-03 96, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0682] [Test Example 3] Herbicidal activity against velvetleaf in foliar application: Approximately 340 cm ３ Plastic pots were filled with field soil, and velvetleaf seeds were sown to a sowing depth of 1 cm, followed by cultivation in a greenhouse. After about two weeks, a wettable powder prepared according to Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed on the foliage of the weeds in the pots using a small sprayer. Cultivation was then continued in the greenhouse, and herbicidal activity was confirmed about 20 days after treatment.

[0683] The compounds that had herbicidal activity against velvetleaf with an index of 3 or higher when sprayed on foliage are listed below. A-0005, A-0009, A-0010, A-0013, A-0014, A-0015, A-0019, A-0021, A-0 022, A-0023, A-0026, A-0028, A-0032, A-0034, A-0036, A-0040, A-0041, A-0042, A-0045, A-0046, A-0052, A-0057, A-0058, A-0062, A-0074, A-0 076, A-0084, A-0086, A-0087, A-0090, A-0091, A-0112, A-0143, A-0174, A-0175, A-0176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0187, A-0 188, A-0191, A-0194, A-0195, A-0210, A-0241, A-0246, A-0247, A-0251, A-0252, A-0254, A-0272, A-0277, A-0278, A-0283, A-0293, A-0295, A-0 296, A-0297, A-0298, A-0299, A-0300, A-0301, A-0302, A-0308, A-0309, A-0310, A-0311, A-0312, A-0313, A-0314, A-0318, A-0319, A-0320, A-0 322, A-0323, A-0324, A-0325, A-0326, A-0327, A-0331, A-0332, A-0333, A-0334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0345, A-0346, A-0 347, A-0348, A-0349, A-0350, A-0351, A-0352, A-0353, A-0354, A-0355, A-0356, A-0357, A-0358, A-0359, A-0360, A-0361, A-0362, A-0363, A-0 364, A-0365, A-0366, A-0367, A-0369, A-0370, A-0371, A-0372, A-0373, A-0374, A-0375, A-0376, A-0377, A-0378, A-0379, A-0380, A-0381, A-0 383, A-0384, A-0385, A-0386, A-0387, A-0388, A-0389, A-0390, A-0391,A-0392、A-0393、A-0394、A-0395、A-0396、A-0397、A-0398、A-0399、A-0401、A-0403、A-0404、A-0405、A-0406、A-0407、A-0408、A-0409、A-0410、A-0411、A-0412、A-0413、A-0419、A-0420、A-0421、A-0422、A-0423、A-0424、A-0425、A-0426、A-0432、A-0433、A-0434、A-0435、A-0436、A-0437、A-0438、A-0439、A-0440、A-0441、A-0442、A-0443、A-0446、A-0447、A-0449、A-0450、A-0451、A-0452、A-0453、A-0454、A-0455、A-0456、A-0465、A-0466、A-0467、A-0470、A-0472、A-0473、A-0474、A-0475、A-0476、A-0477、A-0478、A-0479、A-0480、A-0481、A-0485、A-0486、A-0487、A-0488、A-0490、A-0491、A-0493、A-0494、A-0496、A-0497、A-0499、A-0500、A-0502、A-0503、A-0504、A-0505、A-0506、A-0508、A-0509、A-0510、A-0511、A-0514、A-0522、A-0524、A-0525、A-0526、A-0527、A-0528、A-0529、A-0531、A-0532、A-0533、A-0534、A-0535、A-0536、A-0537、A-0538、A-0539、A-0540、A-0542、A-0543、A-0544、A-0545、A-0546、A-0547、A-0548、A-0549、A-0550、A-0551、A-0552、A-0553、A-0554、A-0571、A-0576、A-0577、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0588、A-0589、A-0605、A-0611、A-0626、A-0627、A-0628、A-0629、A-0640、A-0645、A-0646、A-0651、A-0672、A-0677、A-0678、A-0688、A-0689、A-0704、A-0710, A-0725, A-0726, A-0729, A-0740, A-0773, A-0778, A-0779, A-0783, A-0784, A-0789, A-0805, A-08 10, A-0811, A-0837, A-0842, A-0843, A-0868, A-0873, A-0874, A-0889, A-0900, A-0906, A-0930, A-0943, A -0974, A-0995, A-0997, B-0058, B-0073, B-0095, B-0107, B-0116, B-0117, B-0120, B-0121, B-0130, B-026 1, B-0323, B-0339, B-0422, B-0485, B-0486, B-0489, B-0490, B-0491, B-0492, B-0526, B-0633, B-0664, B-0 665, B-0685, B-0686, B-0695, B-0702, B-0707, B-0708, B-0709, B-0712, B-0713, B-0714, B-0720, B-0722, B-0723, B-0730, B-0732, B-0755, B-0756, B-0759, B-0760, B-0884, B-0950, B-0976, B-0977, B-0980, B-098 1, B-1011, B-1012, B-1042, B-1043, B-1074, C-0043, C-0044, C-0050, C-0230, C-0236, C-0240, C-0293, C- 0395, C-0396, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0684] [Test Example 4] Herbicidal activity confirmation test against beetle in foliage treatment: Approximately 340 cm ３ Plastic pots were filled with field soil, and seeds of Amaranthus retroflexus were sown to a sowing depth of 1 cm and cultivated in a greenhouse. After about two weeks, a wettable powder prepared according to Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed on the foliage of the weeds in the pots using a small sprayer. Growth was then continued in the greenhouse, and herbicidal activity was confirmed about 20 days after treatment.

[0685] The compounds that showed herbicidal activity against beetle retroflexus with an index of 3 or higher when applied to the foliage are as follows: A-0005, A-0007, A-0009, A-0010, A-0013, A-0014, A-0015, A-0019, A-0 021, A-0022, A-0023, A-0024, A-0025, A-0026, A-0027, A-0028, A-0030, A-0031, A-0032, A-0033, A-0034, A-0035, A-0036, A-0037, A-0038, A-0 039, A-0040, A-0041, A-0042, A-0043, A-0045, A-0046, A-0047, A-0048, A-0049, A-0050, A-0052, A-0053, A-0054, A-0055, A-0056, A-0057, A-0 058, A-0059, A-0062, A-0074, A-0076, A-0077, A-0084, A-0085, A-0086, A-0087, A-0089, A-0090, A-0091, A-0092, A-0093, A-0094, A-0095, A-0 112, A-0143, A-0149, A-0174, A-0175, A-0176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0187, A-0188, A-0191, A-0194, A-0195, A-0210, A-0 226, A-0241, A-0246, A-0247, A-0251, A-0252, A-0254, A-0272, A-0277, A-0278, A-0283, A-0293, A-0294, A-0295, A-0296, A-0297, A-0298, A-0 299, A-0300, A-0301, A-0302, A-0303, A-0308, A-0309, A-0310, A-0311, A-0312, A-0313, A-0314, A-0315, A-0317, A-0318, A-0319, A-0320, A-0 321, A-0322, A-0323, A-0324, A-0325, A-0326, A-0327, A-0329, A-0331, A-0332, A-0333, A-0334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0 345, A-0346, A-0347, A-0348, A-0349, A-0350, A-0351, A-0352, A-0353,A-0354、A-0355、A-0356、A-0357、A-0358、A-0359、A-0360、A-0361、A-0362、A-0363、A-0364、A-0365、A-0366、A-0367、A-0368、A-0369、A-0370、A-0371、A-0372、A-0373、A-0374、A-0375、A-0376、A-0377、A-0378、A-0379、A-0380、A-0381、A-0382、A-0383、A-0384、A-0385、A-0386、A-0387、A-0388、A-0389、A-0390、A-0391、A-0392、A-0393、A-0394、A-0395、A-0396、A-0397、A-0398、A-0399、A-0400、A-0401、A-0402、A-0403、A-0404、A-0405、A-0406、A-0407、A-0408、A-0409、A-0410、A-0411、A-0412、A-0413、A-0419、A-0420、A-0421、A-0422、A-0423、A-0424、A-0425、A-0426、A-0432、A-0433、A-0434、A-0435、A-0436、A-0437、A-0438、A-0439、A-0440、A-0441、A-0442、A-0443、A-0446、A-0447、A-0448、A-0449、A-0450、A-0451、A-0452、A-0453、A-0454、A-0455、A-0456、A-0457、A-0464、A-0465、A-0466、A-0467、A-0468、A-0469、A-0470、A-0472、A-0473、A-0474、A-0475、A-0476、A-0477、A-0478、A-0479、A-0480、A-0481、A-0483、A-0484、A-0485、A-0486、A-0487、A-0488、A-0489、A-0490、A-0491、A-0492、A-0493、A-0494、A-0495、A-0496、A-0497、A-0498、A-0499、A-0500、A-0501、A-0502、A-0503、A-0504、A-0505、A-0506、A-0507、A-0508、A-0509、A-0510、A-0511、A-0514、A-0515、A-0519、A-0520、A-0521、A-0522、A-0523、A-0524、A-0525、A-0526、A-0527、A-0528、A-0529、A-0530、A-0531、A-0532、A-0533、A-0534、A-0535、A-0536、A-0537、A-0538、A-0539、A-0540、A-0541、A-0542、A-0543、A-0544、A-0545、A-0546、A-0547、A-0548、A-0549、A-0550、A-0551、A-0552、A-0553、A-0554、A-0557、A-0571、A-0576、A-0577、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0588、A-0589、A-0605、A-0611、A-0626、A-0627、A-0628、A-0629、A-0640、A-0645、A-0646、A-0651、A-0672、A-0677、A-0678、A-0688、A-0689、A-0704、A-0710、A-0725、A-0726、A-0729、A-0740、A-0761、A-0762、A-0773、A-0778、A-0779、A-0783、A-0784、A-0789、A-0805、A-0810、A-0811、A-0826、A-0837、A-0842、A-0843、A-0868、A-0873、A-0874、A-0889、A-0900、A-0905、A-0906、A-0929、A-0930、A-0931、A-0943、A-0974、A-0995、A-0997、B-0006、B-0011、B-0037、B-0042、B-0058、B-0073、B-0095、B-0100、B-0107、B-0116、B-0117、B-0120、B-0121、B-0129、B-0130、B-0131、B-0261、B-0318、B-0323、B-0339、B-0391、B-0422、B-0423、B-0485、B-0486、B-0489、B-0490、B-0491、B-0492、B-0525、B-0526、B-0529、B-0530、B-0564、B-0567、B-0568、B-0633、B-0639、B-0643、B-0664、B-0665、B-0670、B-0685、B-0686、B-0695、B-0702、B-0707、B-0708、B-0709, B-0712, B-0713, B-0714, B-0720, B-0722, B-0723, B-0730, B-0732, B-0755, B-0756, B-0759, B-0760, B-0 787, B-0788, B-0819, B-0884, B-0945, B-0946, B-0949, B-0950, B-0976, B-0977, B-0980, B-0981, B-1011, B-1012, B-1042, B-1043, B-1073, B-1074, C-0036, C-0043, C-0044, C-0047, C-0050, C-0230, C-0236, C-0240, C-0246, C-0 293, C-0395, C-0396, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0686] [Test Example 5] Herbicidal activity confirmation test against barnyard grass in soil treatment: Approximately 340 cm ３ Plastic pots were filled with field soil and barnyard grass seeds were sown to a sowing depth of 1 cm. A wettable powder prepared in accordance with Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and the diluted powder was sprayed over the entire soil surface with a small sprayer in an amount equivalent to 1,000 liters per hectare. The plants were then grown in a greenhouse, and herbicidal activity was confirmed approximately 20 days after treatment.

[0687] The compounds that showed herbicidal activity against barnyardgrass with an index of 3 or more when applied to soil are as follows: A-0007, A-0009, A-0010, A-0013, A-0014, A-0015, A-0019, A-0021, A-0 022, A-0023, A-0028, A-0030, A-0031, A-0032, A-0033, A-0035, A-0036, A-0038, A-0039, A-0040, A-0041, A-0042, A-0045, A-0046, A-0048, A-0 052, A-0055, A-0057, A-0058, A-0062, A-0074, A-0075, A-0076, A-0077, A-0084, A-0085, A-0086, A-0087, A-0090, A-0091, A-0093, A-0112, A-0 143, A-0159, A-0169, A-0174, A-0175, A-0176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0187, A-0188, A-0191, A-0194, A-0195, A-0210, A-0 226, A-0241, A-0246, A-0247, A-0251, A-0252, A-0254, A-0272, A-0277, A-0278, A-0283, A-0293, A-0295, A-0296, A-0297, A-0298, A-0299, A-0 300, A-0301, A-0302, A-0308, A-0309, A-0310, A-0311, A-0312, A-0313, A-0317, A-0318, A-0319, A-0320, A-0322, A-0323, A-0324, A-0325, A-0 326, A-0327, A-0331, A-0332, A-0333, A-0334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0345, A-0346, A-0348, A-0349, A-0350, A-0351, A-0 352, A-0353, A-0354, A-0355, A-0356, A-0357, A-0358, A-0359, A-0360, A-0361, A-0362, A-0363, A-0364, A-0365, A-0366, A-0367, A-0369, A-0 370, A-0371, A-0372, A-0373, A-0374, A-0375, A-0376, A-0377, A-0378,A-0379、A-0380、A-0383、A-0384、A-0385、A-0386、A-0387、A-0388、A-0389、A-0390、A-0391、A-0392、A-0393、A-0394、A-0395、A-0397、A-0399、A-0403、A-0404、A-0406、A-0407、A-0408、A-0409、A-0410、A-0411、A-0412、A-0413、A-0419、A-0420、A-0421、A-0422、A-0423、A-0424、A-0425、A-0426、A-0432、A-0433、A-0434、A-0435、A-0436、A-0438、A-0439、A-0441、A-0442、A-0443、A-0446、A-0447、A-0448、A-0449、A-0450、A-0451、A-0452、A-0453、A-0454、A-0455、A-0464、A-0465、A-0466、A-0467、A-0468、A-0470、A-0472、A-0473、A-0474、A-0475、A-0476、A-0477、A-0478、A-0479、A-0480、A-0481、A-0483、A-0484、A-0485、A-0486、A-0487、A-0488、A-0490、A-0491、A-0493、A-0494、A-0496、A-0497、A-0498、A-0499、A-0500、A-0501、A-0502、A-0503、A-0504、A-0505、A-0506、A-0508、A-0509、A-0514、A-0519、A-0520、A-0521、A-0522、A-0524、A-0525、A-0526、A-0527、A-0528、A-0529、A-0530、A-0531、A-0532、A-0533、A-0534、A-0535、A-0536、A-0537、A-0538、A-0539、A-0540、A-0541、A-0542、A-0543、A-0544、A-0545、A-0546、A-0548、A-0549、A-0550、A-0552、A-0553、A-0554、A-0571、A-0576、A-0577、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0588、A-0589、A-0605、A-0611、A-0626、A-0627、A-0628, A-0629, A-0640, A-0645, A-0646, A-0651, A-0672, A-0677, A-0678, A-0688, A-0689, A-0704, A-0710, A-0725, A-0726, A-0729, A-0740, A-0773, A-0778, A-0779, A-0783, A-0784, A-0789, A-0805, A-0811, A-0837, A-0842, A-0843, A-0889, A-0900, A-0905, A-0906, A-0931, A-0943, A-0995, A-0997, B-0058, B-0073, B-0095, B-0107, B-0116, B-0117, B-0120, B-0121, B-0128, B-0129, B-0130, B-0131, B-0261, B-0323, B-0339, B-0422, B-0423, B-0485, B-0486, B-0489, B-0490, B-0491, B-0492, B-0526, B-0529, B-0530, B-0567, B-0568, B-0633, B-0639, B-0643, B-0664, B-0665, B-0670, B-0685, B-0686, B-0695, B-0702, B-0707, B-0708, B-0709, B-0712, B-0713, B-0714, B-0722, B-0723, B-0730, B-0732, B-0755, B-0756, B-0759, B-0760, B-0819, B-0884, B-0949, B-0950, B-0976, B-0977, B-0980, B-0981, B-1011, B-1012, B-1042, B-1043, B-1074, C-0043, C-0044, C-0050, C-0230, C-0236, C-0240, C-0395, C-0396, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0688] [Test Example 6] Herbicidal activity against Locust rye in soil treatment: Approximately 340 cm ３Plastic pots (100-liter capacity) were filled with field soil and Locust rye seeds were sown to a sowing depth of 1 cm. A wettable powder prepared according to Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed over the entire soil surface using a small sprayer. Growth was then continued in a greenhouse, and herbicidal activity was confirmed approximately 20 days after treatment.

[0689] The compounds that showed herbicidal activity against Locust rye with an index of 3 or higher when applied to soil are as follows: A-0009, A-0010, A-0013, A-0014, A-0015, A-0019, A-0021, A-0022, A-0 023, A-0028, A-0030, A-0032, A-0035, A-0038, A-0039, A-0040, A-0041, A-0042, A-0045, A-0046, A-0047, A-0048, A-0052, A-0053, A-0055, A-0 057, A-0058, A-0062, A-0076, A-0077, A-0084, A-0085, A-0086, A-0087, A-0090, A-0091, A-0093, A-0112, A-0159, A-0169, A-0174, A-0175, A-0 176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0187, A-0188, A-0191, A-0194, A-0195, A-0210, A-0226, A-0241, A-0246, A-0247, A-0251, A-0 252, A-0254, A-0272, A-0277, A-0278, A-0283, A-0293, A-0295, A-0296, A-0297, A-0298, A-0299, A-0300, A-0301, A-0302, A-0308, A-0309, A-0 311, A-0312, A-0313, A-0314, A-0317, A-0318, A-0319, A-0320, A-0322, A-0323, A-0324, A-0325, A-0326, A-0327, A-0331, A-0332, A-0333, A-0 334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0345, A-0346, A-0347, A-0348, A-0349, A-0350, A-0351, A-0352, A-0353, A-0354, A-0355, A-0 356, A-0357, A-0358, A-0359, A-0360, A-0361, A-0362, A-0364, A-0365, A-0366, A-0367, A-0369, A-0370, A-0371, A-0372, A-0373, A-0374, A-0 375, A-0376, A-0377, A-0378, A-0379, A-0380, A-0381, A-0382, A-0383,A-0384、A-0385、A-0386、A-0387、A-0388、A-0389、A-0390、A-0391、A-0392、A-0393、A-0394、A-0395、A-0396、A-0397、A-0398、A-0399、A-0402、A-0403、A-0404、A-0406、A-0407、A-0408、A-0409、A-0410、A-0411、A-0412、A-0413、A-0419、A-0420、A-0421、A-0422、A-0423、A-0424、A-0425、A-0426、A-0432、A-0433、A-0434、A-0435、A-0436、A-0438、A-0439、A-0441、A-0442、A-0443、A-0446、A-0447、A-0449、A-0450、A-0451、A-0452、A-0453、A-0454、A-0455、A-0464、A-0465、A-0466、A-0467、A-0468、A-0470、A-0472、A-0473、A-0474、A-0475、A-0476、A-0477、A-0478、A-0479、A-0480、A-0481、A-0483、A-0484、A-0485、A-0486、A-0487、A-0488、A-0490、A-0491、A-0493、A-0494、A-0496、A-0497、A-0498、A-0499、A-0500、A-0501、A-0502、A-0503、A-0504、A-0505、A-0506、A-0507、A-0508、A-0509、A-0511、A-0514、A-0515、A-0520、A-0521、A-0522、A-0524、A-0525、A-0526、A-0527、A-0528、A-0529、A-0531、A-0532、A-0533、A-0534、A-0535、A-0536、A-0537、A-0538、A-0539、A-0540、A-0541、A-0542、A-0543、A-0544、A-0545、A-0546、A-0547、A-0548、A-0549、A-0550、A-0552、A-0553、A-0554、A-0571、A-0576、A-0577、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0588、A-0589、A-0605、A-0611、A-0626、A-0627, A-0628, A-0629, A-0640, A-0645, A-0646, A-0651, A-0672, A-0677, A-0678, A-0688, A-0689, A-0704, A-0710, A-0725, A -0729, A-0740, A-0773, A-0778, A-0779, A-0783, A-0784, A-0789, A-0805, A-0810, A-0811, A-0837, A-0842, A-0843, A-0868, A-0 873, A-0874, A-0889, A-0900, A-0905, A-0906, A-0931, A-0943, A-0974, B-0042, B-0073, B-0095, B-0107, B-0116, B-0117, B-012 0, B-0121, B-0128, B-0129, B-0130, B-0131, B-0261, B-0323, B-0339, B-0422, B-0423, B-0485, B-0486, B-0489, B-0490, B-0491, B-0492, B-0529, B-0530, B-0568, B-0633, B-0639, B-0643, B-0664, B-0665, B-0670, B-0685, B-0686, B-0695, B-0702, B-0707, B -0708, B-0709, B-0712, B-0713, B-0714, B-0722, B-0723, B-0730, B-0732, B-0755, B-0756, B-0759, B-0760, B-0884, B-0945, B-0 946, B-0949, B-0950, B-0976, B-0977, B-0980, B-0981, B-1011, B-1012, B-1042, B-1043, B-1074, C-0043, C-0044, C-0050, C-023 0, C-0236, C-0240, C-0395, C-0396, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0690] [Test Example 7] Herbicidal activity against velvetleaf in soil treatment: ３Plastic pots were filled with field soil and velvetleaf seeds were sown to a sowing depth of 1 cm. A wettable powder prepared according to Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed over the entire soil surface using a small sprayer. Growth was then continued in a greenhouse, and herbicidal activity was confirmed approximately 20 days after treatment.

[0691] The compounds that showed herbicidal activity against velvetleaf with an index of 3 or higher when applied to soil are listed below. A-0009, A-0013, A-0014, A-0015, A-0041, A-0086, A-0087, A-0090, A-0 091, A-0112, A-0174, A-0175, A-0176, A-0179, A-0180, A-0182, A-0183, A-0184, A-0187, A-0188, A-0194, A-0195, A-0210, A-0241, A-0246, A-0 247, A-0251, A-0272, A-0277, A-0278, A-0297, A-0298, A-0299, A-0300, A-0308, A-0309, A-0311, A-0312, A-0319, A-0320, A-0323, A-0324, A-0 325, A-0326, A-0331, A-0332, A-0333, A-0334, A-0336, A-0337, A-0343, A-0344, A-0345, A-0347, A-0348, A-0349, A-0350, A-0351, A-0352, A-0 353, A-0355, A-0358, A-0360, A-0362, A-0366, A-0370, A-0371, A-0372, A-0375, A-0378, A-0380, A-0385, A-0390, A-0391, A-0395, A-0402, A-0 403, A-0404, A-0406, A-0407, A-0408, A-0409, A-0410, A-0411, A-0412, A-0413, A-0420, A-0421, A-0422, A-0424, A-0425, A-0426, A-0432, A-0 434, A-0435, A-0436, A-0438, A-0443, A-0446, A-0447, A-0449, A-0450, A-0451, A-0452, A-0453, A-0454, A-0465, A-0470, A-0474, A-0475, A-0 476, A-0479, A-0490, A-0491, A-0496, A-0503, A-0505, A-0506, A-0508, A-0509, A-0514, A-0524, A-0525, A-0526, A-0527, A-0528, A-0531, A-0 532, A-0533, A-0534, A-0535, A-0537, A-0538, A-0539, A-0540, A-0541,A-0542, A-0543, A-0545, A-0546, A-0550, A-0552, A-0553, A-0554, A-0571, A-0576, A-0577, A -0580, A-0581, A-0582, A-0583, A-0584, A-0585, A-0588, A-0589, A-0605, A-0611, A-0626, A-0 640, A-0645, A-0646, A-0672, A-0677, A-0678, A-0688, A-0689, A-0710, A-0725, A-0773, A-077 8, A-0779, A-0783, A-0784, A-0789, A-0837, A-0842, A-0843, A-0900, A-0943, B-0073, B-0095, B-0116, B-0117, B-0120, B-0121, B-0129, B-0131, B-0261, B-0323, B-0339, B-0485, B-0486, B -0489, B-0490, B-0491, B-0492, B-0639, B-0643, B-0664, B-0665, B-0670, B-0686, B-0695, B-0 702, B-0707, B-0708, B-0709, B-0712, B-0713, B-0714, B-0722, B-0723, C-0240, C-0395, C-039 6, D-0011, D-0084, D-0085, D-0089, D-0096, D-0274, D-0282, D-0283, D-0286, D-0287, D-0294,

[0692] [Test Example 8] Herbicidal activity against redroot pigweed in soil treatment: Approximately 340 cm ３ Plastic pots were filled with field soil and seeds of Amaranthus retroflexus were sown to a sowing depth of 1 cm. A wettable powder prepared in accordance with Formulation Example 2 was diluted with water to a dose of 1,000 g per hectare of the test compound, and an amount equivalent to 1,000 liters per hectare of spray water was sprayed over the entire soil surface using a small sprayer. The plants were then grown in a greenhouse, and herbicidal activity was confirmed approximately 20 days after treatment.

[0693] The compounds that showed herbicidal activity against beetle retroflexus with an index of 3 or higher when applied to soil are listed below. A-0005, A-0007, A-0009, A-0010, A-0013, A-0014, A-0015, A-0019, A-0 021, A-0022, A-0023, A-0024, A-0026, A-0028, A-0030, A-0031, A-0032, A-0033, A-0034, A-0035, A-0036, A-0038, A-0039, A-0040, A-0041, A-0 042, A-0045, A-0046, A-0047, A-0048, A-0050, A-0052, A-0053, A-0054, A-0055, A-0057, A-0058, A-0062, A-0075, A-0076, A-0077, A-0084, A-0 085, A-0086, A-0087, A-0090, A-0091, A-0092, A-0094, A-0095, A-0112, A-0143, A-0149, A-0169, A-0174, A-0175, A-0176, A-0179, A-0180, A-0 182, A-0183, A-0184, A-0187, A-0188, A-0191, A-0194, A-0195, A-0210, A-0226, A-0241, A-0246, A-0247, A-0251, A-0252, A-0254, A-0272, A-0 277, A-0278, A-0283, A-0293, A-0294, A-0295, A-0296, A-0297, A-0298, A-0299, A-0300, A-0301, A-0302, A-0308, A-0309, A-0310, A-0311, A-0 312, A-0313, A-0314, A-0315, A-0317, A-0318, A-0319, A-0320, A-0321, A-0322, A-0323, A-0324, A-0325, A-0326, A-0327, A-0329, A-0331, A-0 332, A-0333, A-0334, A-0335, A-0336, A-0337, A-0343, A-0344, A-0345, A-0347, A-0348, A-0349, A-0350, A-0351, A-0352, A-0353, A-0354, A-0 355, A-0356, A-0357, A-0358, A-0359, A-0360, A-0361, A-0362, A-0363,A-0364、A-0365、A-0366、A-0367、A-0369、A-0370、A-0371、A-0372、A-0373、A-0374、A-0375、A-0376、A-0377、A-0378、A-0...

Claims

1. General formula [I] [In general formula [I], A １ When is a nitrogen atom, A ３ represents an oxygen atom or a sulfur atom, and A ３ When is a nitrogen atom, A １ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ２ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a cyanato group, an isocyanato group, a thiocyanato group, an isothiocyanato group, a nitro group, C １ ~C ６ Alkyl group (the C １ ~C ６ The alkyl group is R ７ substituents), C ２ ~C ６ Alkenyl group (C ２ ~C ６ The alkenyl group is R ７ substituents), C ２ ~C ６ Alkynyl group (C ２ ~C ６ The alkynyl group is R ７ substituents), C ３ ~C ６ Cycloalkyl group (the C ３ ~C ６ The cycloalkyl group is R ７ substituents), a heterocyclyl group (the heterocyclyl group is ５ substituents), C ６ ~C １２ Aryl group (the C ６ ~C １２ The aryl group is R ５ substituents), a heteroaryl group (a heteroaryl group is a ５ substituents), C ７ ~C １４ Aralkyl group (said C ７ ~C １４ The aralkyl group is R ５ substituents), a heteroaralkyl group (the heteroaralkyl group may be substituted with one or more substituents selected from R ５ substituents), a hydroxy group, C １ ~C ６ Alkoxy group (the C １ ~C ６ The alkoxy group is R ７ substituents), C ２ ~C ６ Alkenyloxy group (C ２ ~C ６ The alkenyloxy group is R ７ substituents), C ２ ~C ６ Alkynyloxy group (C ２ ~C ６ The alkynyloxy group is R ７ substituents), C ３ ~C ６ A cycloalkyloxy group (the C ３ ~C ６ The cycloalkyloxy group is R ７ substituents), C ６ ~C １２ Aryloxy group (the C ６ ~C １２ The aryloxy group is R ５ substituents), a heteroaryloxy group (the heteroaryloxy group may be substituted with one or more substituents selected from R ５ substituents), C ７ ~C １４ Aralkyloxy group (said C ７ ~C １４ The aralkyloxy group is R ５ substituents), a heteroaralkyloxy group (the heteroaralkyloxy group may be substituted with one or more substituents selected from R ５ substituents), a sulfanyl group, a pentahalosulfanyl group, a formylthio group, C １ ~C ６ Alkylcarbonylthio group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ６ Cycloalkylthio group, C ３ ~C ６ Cycloalkylsulfinyl group, C ３ ~C ６ Cycloalkylsulfonyl group, C ３ ~C ６ Halocycloalkylthio group, C ３ ~C ６ Halocycloalkylsulfinyl group, C ３ ~C ６ Halocycloalkylsulfonyl group, C ６ ~C １２ Arylthio group, C ６ ~C １２ Arylsulfinyl group, C ６ ~C １２ Arylsulfonyl group, heteroarylthio group, heteroarylsulfinyl group, heteroarylsulfonyl group, carboxyl group, C １ ~C ６ an alkoxycarbonyl group, an aminocarbonyl group (the nitrogen atom of the aminocarbonyl group is R ６ substituents), an aminothiocarbonyl group (the nitrogen atom of the aminothiocarbonyl group may be substituted with one or more substituents selected from R ６ substituents), an amino group (the amino group may be substituted with one or more substituents selected from R ６ (substituted with one or more substituents selected from the group consisting of di(C １ ~C ６ R represents an alkyl)sulfinylidene)amino group; ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４ are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ R represents an alkyl)amino group; ５ represents a halogen atom, an azide group, a cyano group, a nitro group, 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, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, carboxyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, mono(C １ ~C ６ alkyl)aminocarbonyl group, di(C １ ~C ６ alkyl)aminocarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ R represents an alkyl)amino group; ６ is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ represents a haloalkoxy group or a hydroxy group, and R ６ may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which it is attached, ７ represents a halogen atom, a cyano group, a nitro group, a hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, C ３ ~C ６ Halocycloalkyl group, cyano C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ a haloalkylsulfonyl group.] or a salt thereof.

2. A pesticide composition containing the azolyloxy heterocyclic compound or its salt according to claim 1 as an active ingredient.

3. The pesticide composition according to claim 2, further comprising a surfactant.

4. A herbicide containing the azolyloxy heterocyclic compound or its salt according to claim 1 as an active ingredient.

5. The herbicide according to claim 4, which has herbicidal activity against weeds that occur in fields, paddy fields, orchards, lawns, non-agricultural land, greenhouses, nursery facilities, or plant factories where useful plants having agricultural, horticultural, and industrial uses are cultivated.

6. The herbicide according to claim 5, wherein the useful plants having agricultural, horticultural and industrial uses are plants transformed in cultivation by breeding methods or genetic engineering techniques.

7. A method for controlling weeds, comprising using an active ingredient amount of the azolyloxy heterocyclic compound or its salt according to claim 1.

8. A method for controlling weeds, comprising applying the pesticide composition according to claim 2 or 3 simultaneously or in divided doses to useful plants having agricultural, horticultural and industrial uses or to a place where useful plants having agricultural, horticultural and industrial uses are to be grown or are already growing.

9. A method for controlling weeds according to claim 7, wherein the location of application is a paddy field, a field, a lawn, an orchard, a non-agricultural land, a greenhouse, a nursery facility, or a plant factory.

10. A method for controlling weeds according to claim 8, wherein the location of application is a paddy field, a field, a lawn, an orchard, a non-agricultural land, a greenhouse, a nursery facility, or a plant factory.

11. A method for using the herbicide according to any one of claims 4 to 6 for controlling weeds in useful plants having agricultural, horticultural and industrial uses.

12. General formula [VI] [In general formula [VI], A １ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４ are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ 2. A compound which is an intermediate for producing the compound represented by the general formula [I] according to claim 1 or a salt thereof, wherein the compound is represented by the formula:

13. General formula [IX] [In general formula [IX], A ３ represents an oxygen atom or a sulfur atom, ４ , A ５ , A ６ and A ７ are each independently a nitrogen atom, C—H or C—R ４ indicates, R １ is a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ６ a cycloalkyl group, or C ３ ~C ６ represents a halocycloalkyl group, R ３ represents a hydrogen atom, a halogen atom, an azide group, a cyano group, a nitro 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 ６ Cycloalkyl group, C ３ ~C ６ a halocycloalkyl group, a phenyl group, a pentahalosulfanyl group, or C １ ~C ６ represents an alkoxycarbonyl group, R ４ are each independently a halogen atom, an azide group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Haloalkyl group, hydroxy group, C １ ~C ６ Alkoxy group, C １ ~C ６ Haloalkoxy group, C ３ ~C ６ Cycloalkyl group, pentahalosulfanyl group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, formyl group, carboxyl group, aminocarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ Alkylcarbonyl group, amino group, mono(C １ ~C ６ alkyl)amino group, or di(C １ ~C ６ 2. A compound which is an intermediate for producing the compound represented by the general formula [I] according to claim 1 or a salt thereof, wherein the compound is represented by the formula:

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