Cinnoline derivatives and herbicidal compositions containing same

Abstract

The present invention provides a compound which exhibits excellent weed control efficacy, represented by formula (I), [where in R represents a 3- to 10-membered heterocyclic group that may be substituted with one or more substituents selected from group A, R represents a halogen atom or the like, R, R, and R may be the same or different and represent a hydrogen atom or the like, R and R may be the same or different and represent a hydrogen atom or the like, X and X may be the same or different and represent an oxygen atom or a sulfur atom, Y represents ZR or the like, and R represents a hydrogen atom or the like. Group A: a group consisting of a halogen atom or the like.] or a salt thereof.

Description

Cinnoline derivatives and herbicidal compositions containing the same

[0001] This patent application claims the priority and benefits under the Paris Convention based on Japanese Patent Application No. 2025-014713 (January 31, 2025), and the entire content described in the above application is incorporated herein by reference. The present invention relates to cinnoline derivatives and herbicidal compositions containing the same.

[0002] Various compounds have been studied and put into practical use for the purpose of controlling weeds (see, for example, Patent Document 1).

[0003] European Patent Application Publication No. 0320793

[0004] An object of the present invention is to provide a compound having excellent control efficacy against weeds.

[0005] As a result of studies to find a compound having excellent control efficacy against weeds, the present inventors have found that the compound represented by the following formula (I) has excellent control efficacy against weeds. That is, the present invention is as follows. [1] Formula (I) [In the formula, R 1 represents a 3- to 10-membered heterocyclic group which may be substituted with one or more substituents selected from Group A, R 2 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, a hydroxy group, a formyl group, a carboxy group, an aminocarbonyl group, an aminosulfonyl group, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from Group F}, a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from Group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2bC6-C10 aryl group, 5-10 member aromatic heterocyclic group, 5-10 member non-aromatic heterocyclic group, C6-C10 aryloxy group {The C6-C10 aryl group, the 5-10 member aromatic heterocyclic group, the 5-10 member non-aromatic heterocyclic group, and the C6-C10 aryloxy group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 This represents Z 2 is an oxygen atom, -S(O) n -, or -NR 2b - represents R 2a R represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, 2b n represents a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, n represents 0, 1, or 2, and R 3 , R 4 , and R 5These are the same or different hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthio groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups C1-C6 hydrocarbon group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)sulfinyl group, (C1-C6 alkyl)sulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl The group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)sulfinyl group, the (C1-C6 alkyl)sulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F, C3-C8 alicyclic hydrocarbon C6-C10 aryl group {The C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, C6-C10 aryl group, 5-10 member aromatic heterocyclic group, 5-10 member non-aromatic heterocyclic group, C6-C10 aryloxy group {The C6-C10 aryl group, the 5-10 member aromatic heterocyclic group, the 5-10 member non-aromatic heterocyclic group, and the C6-C10 aryloxy group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Represents R 6 , and R 7 R represents the same or different hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, C1-C3 alkoxy group, or C1-C3 alkylthio group {the C1-C3 alkyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted with one or more halogen atoms}, or R 6 and R7 These combine to represent an oxo group, a thioxo group, or a methylidene group, R 8 R represents a hydrogen atom, a C1-C6 alkyl group (the C1-C6 alkyl group may be substituted with one or more substituents selected from group H), a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group (the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group I), 9 R represents a hydrogen atom or a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group I}, 10 R represents a hydrogen atom, a C1-C10 chain hydrocarbon group (the C1-C10 chain hydrocarbon group may be substituted with one or more substituents selected from group F), a C3-C8 alicyclic hydrocarbon group (the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E), or a benzyl group (the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J), 11 R represents a C1-C10 chain hydrocarbon group {the C1-C10 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J}, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, 12 X represents a 5-10 member aromatic heterocyclic group {the 5-10 member aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, 1 and X 2 Y represents an oxygen atom or a sulfur atom, whether identical or different in phase. 1 is, Z 1 R10 group, NHS(O)2R 11 , or NHR 12 This represents Z 1represents an oxygen atom or a sulfur atom. Group A: halogen atom, cyano group, nitro group, hydroxyl group, amino group, formyl group, hydroxyl group, aminocarbonyl group, aminosulfonyl group, C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C2-C6 alkenyloxy group, C2-C6 alkynyloxy group, C1-C6 alkylthio group, C2-C6 alkenylthio group, C2-C6 alkynylthio group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino) Carbonyl group, (C2-C8 dialkylamino)carbonyl group, C1-C6 alkylsulfinyl group, C2-C6 alkenylsulfinyl group, C2-C6 alkynylsulfinyl group, C1-C6 alkylsulfonyl group, C2-C6 alkenylsulfonyl group, C2-C6 alkynylsulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C2-C6 alkenyloxy group, the C2-C6 alkynyloxy group, the C1-C6 kylthio group, the C2-C6 alkenylthio group, the C2-C6 alkynylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C2-C6 alkenylsulfinyl group, the C2-C6 alkynylsulfinyl group, the C1-C6 alkylsulfonyl group, the C2-C6 alkenylsulfonyl group, The C2-C6 alkynylsulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F, C3-C6 cycloalkyloxy group, C3-C6 cycloalkenyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkenylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkenylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkenylsulfonyl group,C3-C6 alicyclic hydrocarbon group {The C3-C6 cycloalkyloxy group, the C3-C6 cycloalkenyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkenylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkenylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, the C3-C6 cycloalkenylsulfonyl group, and the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group, 5-10 membered non-aromatic heterocyclic group {The C6-C10 aryl group, the 5-10 membered aromatic heterocyclic group, and the 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R, 13 ) = N - OR 14 A group consisting of R. 13 R represents a hydrogen atom, a C1-C6 alkyl group (the C1-C6 alkyl group may be substituted with one or more substituents selected from group H), a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group (the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group I), 14This represents a hydrogen atom or a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group I}. Group E: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group F: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {The C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}.Group G: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, formyl groups, aminocarbonyl groups, C1-C3 alkyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {The C1-C3 alkyl group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group H: A group consisting of halogen atoms, cyano groups, nitro groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group I: A group consisting of halogen atoms, cyano groups, nitro groups, formyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C3-C5 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {The C1-C3 alkyl group, the C3-C5 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}.Group J: A group consisting of a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a C1-C6 alkylthio group {the C1-C6 alkyl group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group may be substituted with one or more halogen atoms}. ] Compounds represented by (however, R. 2 , R 3 , R 4 , and R 5 Compounds in which R is a hydrogen atom; and 2 , R 3 , and R 4 is a hydrogen atom, R 5 (Excluding compounds in which is a chlorine atom.) (Hereinafter referred to as the present invention compound N) or a salt thereof (Hereinafter, the compound represented by formula (I) or a salt thereof will be referred to as the present invention compound). [2] Group E is a group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {The C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}, The compound or salt thereof described in [1], wherein group F is the group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. [3] X 1 and X2 However, the compound or salt thereof described in [1] or [2] is an oxygen atom. [4] Y 1 However, OR 10 group, NHS(O)2R 11 , or NHR 12 The compound or salt thereof described in any one of [1] to [3]. [5] Y 1 However, OR 10 The compound or salt thereof described in any one of [1] to [3], which is the base. [6] R 6 , and R 7 However, the same or different hydrogen atoms, halogen atoms, cyano groups, C1-C3 alkyl groups, or C1-C3 alkoxy groups {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound or salt thereof described in any one of [1] to [5], in which the two groups combine to form an oxo group. [7] R 6 , and R 7 However, a compound or salt thereof described in any one of [1] to [5], which is a hydrogen atom. [8] R 3 , R 4 , and R 5 However, the compound or salt thereof according to any one of [1] to [7], which is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}. [9] R 3 , R 4 , and R 5 However, a compound or salt thereof described in any one of [1] to [7], which is a hydrogen atom.

[10] R 2However, halogen atoms, cyano groups, C1-C3 alkyl groups, C2-C3 alkenyl groups, C2-C3 alkynyl groups, C1-C3 alkoxy groups, C2-C3 alkenyloxy groups, C2-C3 alkynyloxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C2-C3 alkenyl group, the C2-C3 alkynyl group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1 C3-C5 cycloalkyl group, C3-C5 alkylsulfinyl group, and C3-C5 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, C3-C5 cycloalkyl group, C3-C5 cycloalkyloxy group, C3-C5 cycloalkylthio group, C3-C5 cycloalkylsulfinyl group, C3-C5 cycloalkylsulfonyl group {the C3-C5 cycloalkyl group, C3-C5 cycloalkyloxy group, C3-C5 cycloalkylthio group, C3-C5 cycloalkylsulfinyl group, and C3-C5 cycloalkylsulfonyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 The compound or salt thereof described in any one of [1] to [9].

[11] R 2 The compound or salt thereof according to any one of [1] to [9], wherein the compound is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, or a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}.

[12] R 1The compound or salt thereof according to any one of [1] to

[11] , wherein the compound is a 5-6 member aromatic heterocyclic group which may be substituted with one or more substituents selected from group A {the heteroatoms constituting the 5-6 member aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of heteroatoms is 1, 2, 3, or 4}.

[13] A herbicidal composition comprising the compound or salt thereof according to any one of [1] to

[12] and an inert carrier.

[14] A method for controlling weeds, comprising the step of applying the compound or salt thereof according to any one of [1] to

[12] to weeds or soil in which weeds grow.

[15] Use of the compound or salt thereof according to any one of [1] to

[12] for controlling weeds.

[16] A composition containing one or more components selected from the group consisting of group (d) and group (f), and a compound or salt thereof described in any one of [1] to

[12] : Group (d): phytotoxicity reducing component; Group (f): herbicidal active component.

[0006] This invention makes it possible to control weeds.

[0007] The substituents in this invention will now be described. A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, those halogen atoms or substituents may be the same or different. In this specification, the notation "may be substituted with one or more substituents selected from group X" means that if there are two or more substituents selected from group X, those substituents may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is from X to Y. For example, the notation "C1-C8" means that the number of carbon atoms is from 1 to 8. A chain-like hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, and octyl group. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, and 7-octenyl. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 4-pentynyl, 5-hexynyl, and 7-octinyl. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, and octyloxy groups. Examples of alkylthio groups include methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, pentylthio, hexylthio, and octylthio groups.Examples of alkylsulfinyl groups include methylsulfinyl, ethylsulfinyl, propylsulfinyl, and isopropylsulfinyl groups. Examples of alkylsulfonyl groups include methylsulfonyl, ethylsulfonyl, propylsulfonyl, and isopropylsulfonyl groups.

[0008] Examples of alicyclic hydrocarbon groups include cycloalkyl groups and cycloalkenyl groups. Examples of cycloalkyl groups include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, and cyclooctyl groups. Examples of cycloalkenyl groups include cyclopentenyl groups, cyclohexenyl groups, and cyclooctenyl groups. Examples of cycloalkyloxy groups include cyclopropyloxy groups, cyclobutyloxy groups, cyclopentyloxy groups, cyclohexyloxy groups, and cyclooctyloxy groups.

[0009] Examples of C6-C10 aryl groups include phenyl and naphthyl groups. Examples of 5-10 membered aromatic heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, tetradinyl, and quinolyl groups. Examples of 5-10 membered non-aromatic heterocyclic groups include azilidinyl group, oxyranyl group, thyranyl group, azetidinyl group, oxetanyl group, thietanyl group, pyrrolidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, pyrazolinyl group, pyrazolidinyl group, imidazolinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, isoxazolidinyl group, isothiazolidinyl group, isothiazolidinyl group, dioxolanyl group, dioxanyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, azepanyl group, oxepanyl group, and thiepanyl group.Examples of 3-10 membered heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, tetradinyl, quinolyl, azilidinyl, oxyranyl, thyranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, and tetrahydro Examples include thienyl group, pyrazolinyl group, pyrazolidinyl group, imidazolinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolinyl group, isoxazolidinyl group, isothiazolinyl group, isothiazolidinyl group, dioxolanyl group, dioxanyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, azepanyl group, oxepanyl group, and thiepanyl group. Here, the 3-10 membered heterocyclic group includes aromatic heterocyclic groups and non-aromatic heterocyclic groups, for example, a 5-10 membered aromatic heterocyclic group and a 3-10 membered non-aromatic heterocyclic group. Furthermore, the heterocycle in the 3-10 membered heterocyclic group may be a monocycle or a fused ring. Examples of 5-6 membered aromatic heterocyclic groups {the heteroatoms constituting the 5-6 membered aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of heteroatoms is 1, 2, 3, or 4} include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetradinyl groups.Examples of 5-6 member non-aromatic heterocyclic groups {the heteroatoms constituting the 5-6 member non-aromatic heterocyclic group are nitrogen, oxygen, or sulfur atoms, and the number of heteroatoms is 1, 2, 3, or 4} include azilidinyl group, oxyranyl group, thyranyl group, azetidinyl group, oxetanyl group, thietanyl group, pyrrolidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, pyrazolinyl group, pyrazolidinyl group, and imidazolinyl group. Examples include the imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, isoxazolidinyl group, isothiazolidinyl group, isothiazolidinyl group, dioxolanyl group, dioxanyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, and tetrahydrothiopyranyl group.

[0010] The compounds of the present invention may have one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The compounds of the present invention may include each stereoisomer and mixtures of stereoisomers in any ratio.

[0011] Compound N of the present invention may form base addition salts such as isopropylamine salt, dimethylamine salt, sodium salt, and potassium salt when mixed with bases such as isopropylamine, dimethylamine, sodium carbonate, and potassium carbonate. Compound N of the present invention may form acid addition salts such as hydrochloride salt, sulfate salt, nitrate salt, phosphate salt, acetate salt, and benzoate salt when mixed with acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid. Furthermore, in compound N of the present invention, at least one nitrogen atom contained in the compound represented by formula (I) may be substituted with an oxo group, forming an N oxide structure.

[0012] Examples of the compound N of the present invention include the following compounds: [Aspect 1] In the compound N of the present invention, X 1 A compound in which X is an oxygen atom. [Aspect 2] In compound N of the present invention, X 1 A compound in which X is a sulfur atom. [Aspect 3] In compound N of the present invention, X 2A compound in which X is an oxygen atom. [Aspect 4] In the compound N of the present invention, X 2 A compound in which X is a sulfur atom. [Aspect 5] In the compound N of the present invention, X 1 is an oxygen atom and X 2 is a sulfur atom. [Aspect 6] In the compound N of the present invention, X 1 is a sulfur atom and X 2 is an oxygen atom. [Aspect 7] In the compound N of the present invention, X 1 and X 2 are sulfur atoms. [Aspect 8] In the compound N of the present invention, X 1 and X 2 are oxygen atoms. [Aspect 9] In the compound N of the present invention, Y 1 is Z 1 R 10 , or NHS(O)2R 11 . [Aspect 10] In the compound N of the present invention, Y 1 is Z 1 R 10 , or NHR 12 . [Aspect 11] In the compound N of the present invention, Y 1 is Z 1 R 10 . [Aspect 12] In the compound N of the present invention, Y 1 is NHS(O)2R 11 . [Aspect 13] In the compound N of the present invention, Y 1 is NHR 12 . [Aspect 14] In the compound N of the present invention, Y 1 is Z 1 R 10 , NHS(O)2R 11 , or NHR 12 , and R 11 is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}, and R 12However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 15] In compound N of the present invention, Y 1 However, Z 1 R 10 NHS(O)2R 11 , or NHR 12 And R 10 However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 11 However, it is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}, R 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 16] In compound N of the present invention, Y 1 However, Z 1 R 10 , or NHS(O)2R 11 And R 11 However, the compound is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}. [Aspect 17] In compound N of the present invention, Y 1 However, Z 1 R 10 , or NHS(O)2R 11 And R 10However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 11 However, the compound is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}. [Aspect 18] In compound N of the present invention, Y 1 However, Z 1 R 10 , or NHR 12 And R 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 19] In compound N of the present invention, Y 1 However, Z 1 R 10 , or NHR 12 And R 10 However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 20] In compound N of the present invention, Y 1 However, Z 1 R 10 And R 10A compound comprising a hydrogen atom, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F), a C3-C6 alicyclic hydrocarbon group (the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E), or a benzyl group (the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G). [Aspect 21] In compound N of the present invention, Y 1 However, NHS(O)2R 11 And R 11 However, the compound is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}. [Aspect 22] In compound N of the present invention, Y 1 However, NHR 12 And R 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 23] In compound N of the present invention, Y 1 However, OR 10 , or NHS(O)2R 11 A compound that is [Aspect 24] In compound N of the present invention, Y 1 However, OR 10 , or NHR 12 A compound that is [Aspect 25] In compound N of the present invention, Y 1 However, OR 10 A compound that is [Aspect 26] In compound N of the present invention, Y 1 However, OR 10 NHS(O)2R 11 , or NHR 12 And R 11However, it is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}, R 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 27] In compound N of the present invention, Y 1 However, OR 10 NHS(O)2R 11 , or NHR 12 And R 10 However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 11 However, it is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}, R 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 28] In compound N of the present invention, Y 1 However, OR 10 , or NHS(O)2R 11 And R 11However, the compound is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}. [Aspect 29] In compound N of the present invention, Y 1 However, OR 10 , or NHS(O)2R 11 And R 10 However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 11 However, the compound is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a C6 aryl group {the C6 aryl group may be substituted with one or more substituents selected from group G}. [Aspect 30] In compound N of the present invention, Y 1 However, OR 10 , or NHR 12 And R 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 31] In compound N of the present invention, Y 1 However, OR 10 , or NHR 12 And R 10However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 12 However, the compound is a five-membered aromatic heterocyclic group {the five-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Aspect 32] In compound N of the present invention, Y 1 However, OR 10 NHS(O)2R 11 , or NHR 12 And R 11 However, R is a methyl group, an ethyl group {the methyl group and the ethyl group may be substituted with one or more substituents selected from group F}, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}, 12 However, the compound is a triazolyl group, an oxadiazolyl group, a thiadiazolyl group {the triazolyl group, the oxadiazolyl group, and the thiadiazolyl group may be substituted with one or more substituents selected from group G}, or a tetrazolyl group. [Aspect 33] In compound N of the present invention, Y 1 However, OR 10 NHS(O)2R 11 , or NHR 12 And R 10 However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 11 However, R is a methyl group, an ethyl group {the methyl group and the ethyl group may be substituted with one or more substituents selected from group F}, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}, 12However, the compound is a triazolyl group, an oxadiazolyl group, a thiadiazolyl group {the triazolyl group, the oxadiazolyl group, and the thiadiazolyl group may be substituted with one or more substituents selected from group G}, or a tetrazolyl group. [Aspect 34] In compound N of the present invention, Y 1 However, OR 10 , or NHS(O)2R 11 And R 11 However, the compound is a methyl group, an ethyl group {the methyl group and the ethyl group may be substituted with one or more substituents selected from group F}, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}. [Aspect 35] In compound N of the present invention, Y 1 However, OR 10 , or NHS(O)2R 11 And R 10 However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 11 However, the compound is a methyl group, an ethyl group {the methyl group and the ethyl group may be substituted with one or more substituents selected from group F}, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}. [Aspect 36] In compound N of the present invention, Y 1 However, OR 10 , or NHR 12 And R 12 However, the compound is a triazolyl group, an oxadiazolyl group, a thiadiazolyl group {the triazolyl group, the oxadiazolyl group, and the thiadiazolyl group may be substituted with one or more substituents selected from group G}, or a tetrazolyl group. [Aspect 37] In compound N of the present invention, Y 1 However, OR 10 , or NHR 12 And R 10However, R is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}, 12 However, the compound is a triazolyl group, an oxadiazolyl group, a thiadiazolyl group {the triazolyl group, the oxadiazolyl group, and the thiadiazolyl group may be substituted with one or more substituents selected from group G}, or a tetrazolyl group. [Aspect 38] In compound N of the present invention, Y 1 However, NHS(O)2R 11 And R 11 However, the compound is a methyl group, an ethyl group {the methyl group and the ethyl group may be substituted with one or more substituents selected from group F}, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}. [Aspect 39] In compound N of the present invention, Y 1 However, NHR 12 And R 12 However, the compound is a triazolyl group, an oxadiazolyl group, a thiadiazolyl group {the triazolyl group, the oxadiazolyl group, and the thiadiazolyl group may be substituted with one or more substituents selected from group G}, or a tetrazolyl group. [Aspect 40] In compound N of the present invention, Y 1 However, Z 1 R 10 And R 10 A compound comprising a hydrogen atom, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F), a C3-C6 alicyclic hydrocarbon group (the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E), or a benzyl group (the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G). [Aspect 41] In compound N of the present invention, Y 1 However, OR 10 And R 10A compound comprising a hydrogen atom, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F), a C3-C6 alicyclic hydrocarbon group (the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E), or a benzyl group (the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G). [Aspect 42] In compound N of the present invention, Y 1 However, Z 1 R 10 And R 10 However, the compound is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}. [Aspect 43] In compound N of the present invention, Y 1 However, OR 10 And R 10 However, the compound is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}. [Aspect 44] In compound N of the present invention, Y 1 However, OR 10 And R 10 However, it is a compound in which the atom is a hydrogen atom. [Aspect 45] In compound N of the present invention, Y 1 However, OR 10 And R 10 However, a compound having a C1-C10 chain hydrocarbon group {the C1-C10 chain hydrocarbon group may be substituted with one or more substituents selected from group F}. [Aspect 46] In compound N of the present invention, Y 1 However, OR 10 And R 10 However, a compound having a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}. [Aspect 47] In compound N of the present invention, Y 1 However, OR 10 And R 10However, a compound having a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group F}. [Aspect 48] In compound N of the present invention, Y 1 However, OR 10 And R 10 However, a compound having a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J}. [Aspect 49] In compound N of the present invention, Y 1 However, OR 10 And R 10 However, a compound having a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G}. [Aspect 50] In compound N of the present invention, R 6 , and R 7 However, they represent the same or different hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, C1-C3 alkoxy group, or C1-C3 alkylthio group {the C1-C3 alkyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R to form an oxo group or a thioxo group. [Aspect 51] In compound N of the present invention, R 6 , and R 7 However, they represent the same or different hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, or C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R to form an oxo group or a thioxo group. [Aspect 52] In compound N of the present invention, R 6 , and R 7 However, they represent the same or different hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, or C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, or R 6 and R7 A compound in which R is combined with R to form an oxo group or a thioxo group. [Aspect 53] In compound N of the present invention, R 6 , and R 7 A compound in which the same or different hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, C1-C3 alkoxy group, or C1-C3 alkylthio group {the C1-C3 alkyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted with one or more halogen atoms}. [Aspect 54] In compound N of the present invention, R 6 , and R 7 However, they represent the same or different hydrogen atom, halogen atom, cyano group, methyl group, ethyl group, methoxy group, ethoxy group, methylthio group, or ethylthio group {the methyl group, ethyl group, methoxy group, ethoxy group, methylthio group, and ethylthio group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R to form an oxo group or a thioxo group. [Aspect 55] In compound N of the present invention, R 6 , and R 7 However, they represent the same or different hydrogen atom, halogen atom, cyano group, methyl group, ethyl group, methoxy group, ethoxy group, methylthio group, or ethylthio group {the methyl group, ethyl group, methoxy group, ethoxy group, methylthio group, and ethylthio group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 However, the compound is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}. [Aspect 57] In compound N of the present invention, R 6 , and R 7However, they represent the same or different hydrogen atom, halogen atom, cyano group, methyl group, ethyl group, methoxy group, or ethoxy group {the methyl group, ethyl group, methoxy group, and ethoxy group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 A compound in which the hydrogen atom, halogen atom, cyano group, methyl group, ethyl group, methoxy group, or ethoxy group is the same or different in phase {the methyl group, ethyl group, methoxy group, and ethoxy group may be substituted with one or more halogen atoms}. [Aspect 59] In compound N of the present invention, R 6 , and R 7 However, they represent the same or different hydrogen atom, halogen atom, cyano group, methyl group, or methoxy group {the methyl group and the methoxy group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, a methyl group, or a methoxy group {the methyl group and the methoxy group may be substituted with one or more halogen atoms}. [Aspect 61] In compound N of the present invention, R 6 , and R 7 However, they may be the same or different, representing a hydrogen atom or a halogen atom, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 63] In compound N of the present invention, R 6 , and R 7 However, they may be the same or different, representing a hydrogen atom or a cyano group, or R 6 and R 7 A compound in which R is combined with R.6 , and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a cyano group. [Aspect 65] In compound N of the present invention, R 6 , and R 7 However, they may be the same or different, representing a hydrogen atom or a methyl group {the methyl group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a methyl group {the methyl group may be substituted with one or more halogen atoms}. [Aspect 67] In compound N of the present invention, R 6 , and R 7 However, they may be the same or different, representing a hydrogen atom or a methoxy group {the methoxy group may be substituted with one or more halogen atoms}, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 However, the compound is the same or different in phase, and is a hydrogen atom or a methoxy group {the methoxy group may be substituted with one or more halogen atoms}. [Aspect 69] In compound N of the present invention, R 6 , and R 7 is a hydrogen atom, or R 6 and R 7 A compound in which R is combined with R. 6 , and R 7 A compound in which R is combined with the oxo group. [Aspect 71] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different in phase, hydrogen atom, halogen atom, cyano group, nitro group, amino group, hydroxyl group, formyl group, aminocarbonyl group, aminosulfonyl group, C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)sulfinyl group, (C1-C6 alkyl)sulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C 6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)sulfinyl group, the (C1-C6 alkyl)sulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, 5-10 membered non-aromatic heterocyclic group {the 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 72] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different in phase, hydrogen atom, halogen atom, cyano group, nitro group, formyl group, aminocarbonyl group, aminosulfonyl group, C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkyl)sulfinyl group, (C1-C6 alkyl)sulfonyl group, {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the (C1-C6 {The (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkyl)sulfinyl group, and the (C1-C6 alkyl)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C8 alicyclic hydrocarbon group {The C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, 5-10 membered non-aromatic heterocyclic group {The 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 73] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 chain hydrocarbon groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, C1-C3 alkylamino groups, C2-C6 dialkylamino groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, (C1-C3 alkyl (amino)carbonyl group, (C2-C6 dialkylamino)carbonyl group, (C1-C3 alkyl)sulfinyl group, (C1-C3 alkyl)sulfonyl group, (C1-C3 alkylamino)sulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylamino group, the C2-C6 dialkylamino group, the The (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkylamino)carbonyl group, the (C2-C6 dialkylamino)carbonyl group, the (C1-C3 alkyl)sulfinyl group, the (C1-C3 alkyl)sulfonyl group, the (C1-C3 alkylamino)sulfonyl group, and the (C2-C6 dialkylamino)sulfonyl group are each substituted with one or more substituents selected from group F.} may be substituted}, C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, phenyl group, 5-6 member aromatic heterocyclic group, 5-6 member non-aromatic heterocyclic group, phenoxy group {the phenyl group, the 5-6 member aromatic heterocyclic group, the 5-6 member non-aromatic heterocyclic group, and the phenoxy group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 74] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different in phase, hydrogen atom, halogen atom, cyano group, nitro group, amino group, hydroxyl group, formyl group, aminocarbonyl group, aminosulfonyl group, C1-C3 chain hydrocarbon group, C1-C3 alkoxy group, C1-C3 alkylthio group, C1-C3 alkylamino group, C2-C6 dialkylamino group, (C1-C3 alkyl)carbonyl group, (C1-C3 alkoxy)carbonyl group, (C1-C3 alkylamino)carbonyl group, (C2-C6 dialkylamino)carbonyl group, (C1-C3 alkyl)sulfinyl group, (C1-C3 alkyl)sulfonyl group, (C1-C3 alkylamino)sulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C 3 alkylamino group, the C2-C6 dialkylamino group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkylamino)carbonyl group, the (C2-C6 dialkylamino)carbonyl group, the (C1-C3 alkyl)sulfinyl group, the (C1-C3 alkyl)sulfonyl group, the (C1-C3 alkylamino)sulfonyl group, and the (C2-C6 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, 5-6 membered non-aromatic heterocyclic group {the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 75] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different in phase, hydrogen atom, halogen atom, cyano group, nitro group, formyl group, aminosulfonyl group, C1-C3 chain hydrocarbon group, C1-C3 alkoxy group, C1-C3 alkylthio group, (C1-C3 alkyl)carbonyl group, (C1-C3 alkoxy)carbonyl group, (C1-C3 alkyl)sulfinyl group, (C1-C3 alkyl)sulfonyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl) Carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkyl)sulfinyl group, the (C1-C3 alkyl)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, 5-6 membered non-aromatic heterocyclic group {the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 76] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different atoms are hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, C1-C3 alkylamino groups, C2-C6 dialkylamino groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups. Carbonyl group, (C1-C3 alkylamino)carbonyl group, (C2-C6 dialkylamino)carbonyl group, (C1-C3 alkyl)sulfonyl group, (C1-C3 alkylamino)sulfonyl group, (C1-C3 alkylamino)sulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylamino group, the C2-C6 dialkylamino group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkylamino)carbonyl group, the (C2-C6 dialkylamino)carbonyl group, the (C1-C3 alkyl)sulfinyl group, the (C1-C3 alkyl)sulfonyl group, the (C1-C3 alkylamino)sulfonyl group, and the (C2-C6 dialkyl The amino)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {the C3-C6 cycloalkyl group and the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, 5-6 membered non-aromatic heterocyclic group {the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 77] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different in phase, hydrogen atom, halogen atom, cyano group, nitro group, formyl group, aminosulfonyl group, C1-C3 alkyl group, C1-C3 alkenyl group, C1-C3 alkynyl group, C1-C3 alkoxy group, C1-C3 alkylthio group, (C1-C3 alkyl)carbonyl group, (C1-C3 alkoxy)carbonyl group, (C1-C3 alkyl)sulfinyl group, (C1-C3 alkyl)sulfonyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1- C3 alkyl) carbonyl group, the (C1-C3 alkoxy) carbonyl group, the (C1-C3 alkyl) sulfinyl group, the (C1-C3 alkyl) sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {the C3-C6 cycloalkyl group and the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, 5-6 membered non-aromatic heterocyclic group {the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 78] In compound N of the present invention, R 3 , R 4 , and R 5However, the same or different hydrogen atoms, halogen atoms, cyano groups, nitro groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, (C1-C3 alkyl)sulfinyl groups, (C1-C3 alkyl)sulfonyl groups {the C1-C3 alkyl group, the C1-C3 alkenyl group, the C1-C 3. Alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkyl)sulfinyl group, and the (C1-C3 alkyl)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 79] In compound N of the present invention, R 3 , R 4 , and R 5 However, the same or different hydrogen atoms, halogen atoms, cyano groups, nitro groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups {the C1-C3 alkyl group, the C1-C3 alkenyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 80] In compound N of the present invention, R 3 , R 4 , and R 5A compound comprising the same or different hydrogen atom, halogen atom, cyano group, nitro group, C1-C3 alkyl group, C1-C3 alkenyl group, C1-C3 alkynyl group, C1-C3 alkoxy group, C1-C3 alkylthio group, {the C1-C3 alkyl group, the C1-C3 alkenyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted with one or more substituents selected from group F}, or C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}. [Aspect 81] In compound N of the present invention, R 3 , R 4 , and R 5 A compound which is the same or different in phase, comprising a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group {the C1-C3 alkyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}. [Aspect 82] In compound N of the present invention, R 3 , R 4 , and R 5 A compound in which is the same or different in phase, a hydrogen atom, a halogen atom, a cyano group, a methyl group, a methoxy group, a methylthio group {the methyl group, the methoxy group, and the methylthio group may be substituted with one or more substituents selected from group F}, or a cyclopropyl group {the cyclopropyl group may be substituted with one or more substituents selected from group E}. [Aspect 83] In compound N of the present invention, R 3 , R 4 , and R 5 However, the compound is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, a methyl group, a methoxy group {the methyl group and the methoxy group may be substituted with one or more substituents selected from group F}, or a cyclopropyl group {the cyclopropyl group may be substituted with one or more substituents selected from group E}. [Aspect 84] In compound N of the present invention, R 3 , R 4 , and R5 However, the compound is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, or a C1-C3 alkoxy group {the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}. [Aspect 85] In compound N of the present invention, R 3 , R 4 , and R 5 However, the compound is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, or a methoxy group {the methoxy group may be substituted with one or more substituents selected from group F}. [Aspect 86] In compound N of the present invention, R 3 , R 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom, a halogen atom, or a cyano group. [Aspect 87] In compound N of the present invention, R 3 , R 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 88] In compound N of the present invention, R 3 , R 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a cyano group. [Aspect 89] In compound N of the present invention, R 3 , R 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom, fluorine atom, chlorine atom, or bromine atom. [Aspect 90] In compound N of the present invention, R 3 , R 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a fluorine atom. [Aspect 91] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 92] In compound N of the present invention, R 3However, R is a hydrogen atom, a halogen atom, a cyano group, a methyl group, or a methoxy group {the methyl group and the methoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 93] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 94] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, a cyano group, a methyl group, or a methoxy group {the methyl group and the methoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 95] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, a cyano group, or a C1-C3 alkoxy group {the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 96] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, a cyano group, or a methoxy group {the methoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 97] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, a cyano group, or a C1-C3 alkoxy group {the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 98] In compound N of the present invention, R 3However, R is a hydrogen atom, a halogen atom, a cyano group, or a methoxy group {the methoxy group may be substituted with one or more substituents selected from group F}, 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 99] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, or a cyano group. 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect 100] In compound N of the present invention, R 3 However, R is a hydrogen atom, a halogen atom, or a cyano group. 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 101] In compound N of the present invention, R 3 However, it is a hydrogen atom or a halogen atom, R 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 102] In compound N of the present invention, R 4 However, R is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 103] In compound N of the present invention, R 4 However, R is a hydrogen atom, a halogen atom, a cyano group, a methyl group, or a methoxy group {the methyl group and the methoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 104] In compound N of the present invention, R 4 However, R is a hydrogen atom, a halogen atom, a cyano group, or a C1-C3 alkoxy group {the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 105] In compound N of the present invention, R 4However, R is a hydrogen atom, a halogen atom, a cyano group, or a methoxy group {the methoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 106] In compound N of the present invention, R 4 However, R is a hydrogen atom, a halogen atom, or a cyano group. 3 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 107] In compound N of the present invention, R 4 However, it is a hydrogen atom or a halogen atom, R 3 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 108] In compound N of the present invention, R 5 However, R is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 109] In compound N of the present invention, R 5 However, R is a hydrogen atom, a halogen atom, a cyano group, a methyl group, or a methoxy group {the methyl group and the methoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 110] In compound N of the present invention, R 5 However, R is a hydrogen atom, a halogen atom, a cyano group, or a C1-C3 alkoxy group {the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 111] In compound N of the present invention, R 5 However, R is a hydrogen atom, a halogen atom, a cyano group, or a methoxy group {the methoxy group may be substituted with one or more substituents selected from group F}, 3 , and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 112] In compound N of the present invention, R 5However, R is a hydrogen atom, a halogen atom, or a cyano group. 3 , and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 113] In compound N of the present invention, R 5 However, it is a hydrogen atom or a halogen atom, R 3 , and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 114] In compound N of the present invention, R 3 However, it is a compound in which the atom is a hydrogen atom. [Aspect 115] In compound N of the present invention, R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 116] In compound N of the present invention, R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 117] In compound N of the present invention, R 3 and R 4 However, it is a compound in which the atom is a hydrogen atom. [Aspect 118] In compound N of the present invention, R 3 and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 119] In compound N of the present invention, R 4 and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 120] In compound N of the present invention, R 3 , R 4 , and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 121] In compound N of the present invention, R 3 , R 4 , and R 5 A compound having the same or different hydrogen atom, phenyl group, 5-6 membered aromatic heterocyclic group, and phenoxy group {the phenyl group, the 5-6 membered aromatic heterocyclic group, and the phenoxy group may be substituted with one or more substituents selected from group G}. [Aspect 122] In compound N of the present invention, R 3 , R 4 , and R 5A compound in which the hydrogen atom, amino group, hydroxyl group, aminocarbonyl group, C1-C3 alkylamino group, C2-C6 dialkylamino group, (C1-C3 alkylamino)carbonyl group, (C2-C6 dialkylamino)carbonyl group, (C1-C3 alkylamino)sulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 alkylamino group, the C2-C6 dialkylamino group, the (C1-C3 alkylamino)carbonyl group, the (C2-C6 dialkylamino)carbonyl group, the C1-C3 alkylamino)sulfonyl group, and the (C2-C6 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F}. [Aspect 123] In compound N of the present invention, R 3 , R 4 , and R 5 A compound having the same or different phases, a hydrogen atom, an aminosulfonyl group, a C1-C3 alkylthio group, a (C1-C3 alkyl)sulfinyl group, or a (C1-C3 alkyl)sulfonyl group {the C1-C3 alkylthio group, the (C1-C3 alkyl)sulfinyl group, and the (C1-C3 alkyl)sulfonyl group may be substituted with one or more substituents selected from group F}. [Aspect 124] In compound N of the present invention, R 3 , R 4 , and R 5 However, the same or different hydrogen atoms, (C1-C3 alkyl)carbonyl group, (C1-C3 alkoxy)carbonyl group {the (C1-C3 alkyl)carbonyl group and the (C1-C3 alkoxy)carbonyl group may be substituted with one or more substituents selected from group F}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 125] In compound N of the present invention, R 2 However, hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, carboxyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C6 chain hydrocarbon groups {the C1-C6 chain hydrocarbon groups may be substituted with one or more substituents selected from group F}, C3-C8 alicyclic hydrocarbon groups {the C3-C8 alicyclic hydrocarbon groups may be substituted with one or more substituents selected from group E}, -Z2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2b A group, a 5-10 member aromatic heterocyclic group, a 5-10 member non-aromatic heterocyclic group {the 5-10 member aromatic heterocyclic group and the 5-10 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Z 2 However, the oxygen atom, -S(O) n -, or -NR 2b - and R 2a However, it is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 126] In compound N of the present invention, R 2 However, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, carboxyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C6 chain hydrocarbon groups {the C1-C6 chain hydrocarbon groups may be substituted with one or more substituents selected from group F}, C3-C8 alicyclic hydrocarbon groups {the C3-C8 alicyclic hydrocarbon groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2bA group, a 5-10 member aromatic heterocyclic group, a 5-10 member non-aromatic heterocyclic group {the 5-10 member aromatic heterocyclic group and the 5-10 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Z 2 However, the oxygen atom, -S(O) n -, or -NR 2b - and R 2a However, it is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 127] In compound N of the present invention, R 2 However, hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, carboxyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 chain hydrocarbon groups {the C1-C3 chain hydrocarbon groups may be substituted with one or more substituents selected from group F}, C3-C6 alicyclic hydrocarbon groups {the C3-C6 alicyclic hydrocarbon groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2b A group, a 5-6 member aromatic heterocyclic group, a 5-6 member non-aromatic heterocyclic group {the 5-6 member aromatic heterocyclic group and the 5-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Z 2However, the oxygen atom, -S(O) n -, or -NR 2b - and R 2a However, it is a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 128] In compound N of the present invention, R 2 However, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, carboxyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 chain hydrocarbon groups {the C1-C3 chain hydrocarbon groups may be substituted with one or more substituents selected from group F}, C3-C6 alicyclic hydrocarbon groups {the C3-C6 alicyclic hydrocarbon groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2b A group, a 5-6 member aromatic heterocyclic group, a 5-6 member non-aromatic heterocyclic group {the 5-6 member aromatic heterocyclic group and the 5-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Z 2 However, the oxygen atom, -S(O) n -, or -NR 2b - and R 2aHowever, it is a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 129] In compound N of the present invention, R 2 However, hydrogen atoms, halogen atoms, cyano groups, nitro groups, formyl groups, aminosulfonyl groups, C1-C3 chain hydrocarbon groups {the C1-C3 chain hydrocarbon groups may be substituted with one or more substituents selected from group F}, C3-C6 alicyclic hydrocarbon groups {the C3-C6 alicyclic hydrocarbon groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2b A group, a 5-6 member non-aromatic heterocyclic group {the 5-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Z 2 However, the oxygen atom, -S(O) n -, or -NR 2b - and R 2a However, it is a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R 2bA compound in which n is a hydrogen atom, a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, and n is 0, 1, or 2. [Aspect 130] In compound N of the present invention, R 2 However, halogen atoms, cyano groups, nitro groups, formyl groups, aminosulfonyl groups, C1-C3 chain hydrocarbon groups {the C1-C3 chain hydrocarbon groups may be substituted with one or more substituents selected from group F}, C3-C6 alicyclic hydrocarbon groups {the C3-C6 alicyclic hydrocarbon groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -C(=O)NR 2a R 2b group, -SO2NR 2a R 2b A group, a 5-6 member non-aromatic heterocyclic group {the 5-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 Z 2 However, the oxygen atom, -S(O) n -, or -NR 2b - and R 2a However, it is a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C6 alicyclic hydrocarbon group {the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, and n is 0, 1, or 2. [Aspect 131] In compound N of the present invention, R 2However, hydrogen atoms, halogen atoms, cyano groups, nitro groups, formyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups {the C1-C3 alkyl groups, C1-C3 alkenyl groups, and C1-C3 alkynyl groups may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups, C3-C6 cycloalkenyl groups {the C3-C6 cycloalkyl groups, and C3-C6 cycloalkenyl groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -SO2NR 2a R 2b base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a However, C1-C3 alkyl group, C1-C3 alkenyl group, C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {the C3-C6 cycloalkyl group and the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C3 alkyl group, a C1-C3 alkenyl group, or a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl may be substituted with one or more substituents selected from group F}, and n is 0, 1, or 2. [Aspect 132] In compound N of the present invention, R 2However, halogen atoms, cyano groups, nitro groups, formyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups {the C1-C3 alkyl groups, C1-C3 alkenyl groups, and C1-C3 alkynyl groups may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups, C3-C6 cycloalkenyl groups {the C3-C6 cycloalkyl groups, and C3-C6 cycloalkenyl groups may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -SO2NR 2a R 2b base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a However, C1-C3 alkyl group, C1-C3 alkenyl group, C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {the C3-C6 cycloalkyl group and the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, R 2b A compound in which n is a hydrogen atom, a C1-C3 alkyl group, a C1-C3 alkenyl group, or a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl may be substituted with one or more substituents selected from group F}, and n is 0, 1, or 2. [Aspect 133] In compound N of the present invention, R 2However, hydrogen atoms, halogen atoms, cyano groups, nitro groups, formyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -SO2NR 2a R 2b base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a However, it is a C1-C3 alkyl group, a C1-C3 alkenyl group, a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, R 2b However, the compound is a hydrogen atom, a C1-C3 alkyl group {the C1-C3 alkyl group may be substituted with one or more substituents selected from group F}, and n is 0, 1, or 2. [Aspect 134] In compound N of the present invention, R 2 However, halogen atoms, cyano groups, nitro groups, formyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a group, -SO2NR2a R 2b base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a However, it is a C1-C3 alkyl group, a C1-C3 alkenyl group, a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, R 2b However, the compound is a hydrogen atom, a C1-C3 alkyl group {the C1-C3 alkyl group may be substituted with one or more substituents selected from group F}, and n is 0, 1, or 2. [Aspect 135] In compound N of the present invention, R 2 However, hydrogen atoms, halogen atoms, cyano groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a A compound in which n is a C1-C3 alkyl group, a C1-C3 alkenyl group, a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 136] In compound N of the present invention, R2 However, halogen atoms, cyano groups, C1-C3 alkyl groups, C1-C3 alkenyl groups, C1-C3 alkynyl groups {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, -Z 2 R 2a group, -C(=O)R 2a group, -C(=O)OR 2a base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a A compound in which n is a C1-C3 alkyl group, a C1-C3 alkenyl group, a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 137] In compound N of the present invention, R 2 However, hydrogen atoms, halogen atoms, cyano groups, C1-C3 alkyl groups {the C1-C3 alkyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, -Z 2 R 2a base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2aA compound in which n is a C1-C3 alkyl group, a C1-C3 alkenyl group, a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 138] In compound N of the present invention, R 2 However, halogen atoms, cyano groups, C1-C3 alkyl groups {the C1-C3 alkyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, -Z 2 R 2a base, or C(R 8 ) = N - OR 9 Z 2 However, oxygen atoms, or -S(O) n - and R 2a A compound in which n is a C1-C3 alkyl group, a C1-C3 alkenyl group, a C1-C3 alkynyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, and the C1-C3 alkynyl group may be substituted with one or more substituents selected from group F}, or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, and n is 0, 1, or 2. [Aspect 139] In compound N of the present invention, R 2However, halogen atoms, cyano groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C2-C3 alkenyloxy groups, C2-C3 alkynyloxy groups, C1-C3 alkylthio groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group are selected from group F. The above substituents may be substituted}, C3-C5 cycloalkyl group, C3-C5 cycloalkyloxy group, C3-C5 cycloalkylthio group, C3-C5 cycloalkylsulfinyl group, C3-C5 cycloalkylsulfonyl group {The C3-C5 cycloalkyl group, the C3-C5 cycloalkyloxy group, the C3-C5 cycloalkylthio group, the C3-C5 cycloalkylsulfinyl group, and the C3-C5 cycloalkylsulfonyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 140] In compound N of the present invention, R 2 However, halogen atoms, cyano groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, C3-C5 cycloalkyl C3-C5 cycloalkyloxy group, C3-C5 cycloalkylthio group, C3-C5 cycloalkylsulfinyl group, C3-C5 cycloalkylsulfonyl group {The C3-C5 cycloalkyl group, the C3-C5 cycloalkyloxy group, the C3-C5 cycloalkylthio group, the C3-C5 cycloalkylsulfinyl group, and the C3-C5 cycloalkylsulfonyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 141] In compound N of the present invention, R2 However, halogen atoms, cyano groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, C3-C5 cycloalkyl groups {the C3-C5 cycloalkyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 A compound that is [Aspect 142] In compound N of the present invention, R 2 A compound in which a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, or a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}. [Embodiment 143] In compound N of the present invention, R 2 A compound in which a halogen atom, a cyano group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, or a C1-C3 alkylsulfonyl group {the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}. [Aspect 144] In compound N of the present invention, R 2 A compound in which a halogen atom, a cyano group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a methylsulfinyl group, an ethylsulfinyl group, a methylsulfonyl group, or an ethylsulfonyl group {the methoxy group, the ethoxy group, the methylthio group, the ethylthio group, the methylsulfinyl group, the ethylsulfinyl group, the methylsulfonyl group, and the ethylsulfonyl group may be substituted with one or more substituents selected from group F}. [Aspect 145] In compound N of the present invention, R 2A compound in which a halogen atom, a cyano group, a methoxy group, an ethoxy group, a methylthio group, a methylsulfinyl group, or a methylsulfonyl group {the methoxy group, the ethoxy group, the methylthio group, the methylsulfinyl group, and the methylsulfonyl group may be substituted with one or more substituents selected from group F}. [Aspect 146] In compound N of the present invention, R 2 However, a compound which is a hydrogen atom or a halogen atom. [Aspect 147] In compound N of the present invention, R 2 However, a compound which is a hydrogen atom or a halogen atom. [Aspect 148] In compound N of the present invention, R 2 , R 4 and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 149] In compound N of the present invention, R 2 , R 3 and R 5 However, it is a compound in which the atom is a hydrogen atom. [Aspect 150] In compound N of the present invention, R 1 However, a compound which is a 3-9 membered heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 151] In compound N of the present invention, R 1 However, a compound which is a 5-9 member heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 152] In compound N of the present invention, R 1 However, a compound which is a 5-6 membered heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 153] In compound N of the present invention, R 1 However, the compound is a 5-10 member aromatic heterocyclic group or a 3-10 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 154] In compound N of the present invention, R 1 However, the compound is a 5-9 member aromatic heterocyclic group or a 3-10 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 155] In compound N of the present invention, R 1 However, the compound is a 5-6 member aromatic heterocyclic group or a 3-10 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 156] In compound N of the present invention, R 1However, the compound is a 5-10 member aromatic heterocyclic group or a 5-10 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 157] In compound N of the present invention, R 1 However, the compound is a 5-10 member aromatic heterocyclic group or a 5-9 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 158] In compound N of the present invention, R 1 However, the compound is a 5-10 member aromatic heterocyclic group or a 5-6 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 159] In compound N of the present invention, R 1 However, the compound is a 5-9 member aromatic heterocyclic group or a 5-10 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 160] In compound N of the present invention, R 1 However, the compound is a 5-9 member aromatic heterocyclic group or a 5-9 member non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group A. [Aspect 161] In compound N of the present invention, R 1 However, the compound is a 5-9 member aromatic heterocyclic group or a 5-6 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 162] In compound N of the present invention, R 1 However, the compound is a 5-6 member aromatic heterocyclic group or a 5-10 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 163] In compound N of the present invention, R 1 However, the compound is a 5-6 member aromatic heterocyclic group or a 5-9 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 164] In compound N of the present invention, R 1 A compound which is a 5-6 member aromatic heterocyclic group or a 5-6 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 165] In compound N of the present invention, R 1 However, a compound which is a 5-10 member aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 166] In compound N of the present invention, R 1However, a compound which is a 5-9 member aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 167] In compound N of the present invention, R 1 However, a compound which is a 5-6 member aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 168] In compound N of the present invention, R 1 However, a compound which is a 3-10 member non-aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 169] In compound N of the present invention, R 1 However, a compound which is a 5-10 member non-aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 170] In compound N of the present invention, R 1 However, a compound which is a 5-9 member non-aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 171] In compound N of the present invention, R 1A compound that is a 5-6 member non-aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 172] A compound in any one of aspects 150 to 152, wherein the heteroatoms constituting the heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, 3, or 4. [Aspect 173] A compound in any one of aspects 150 to 152, wherein the heteroatoms constituting the heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3. [Aspect 174] A compound in any one of aspects 150 to 152, wherein the heteroatoms constituting the heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1 or 2. [Aspect 175] A compound in any one of aspects 153 to 164 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, 3, or 4. [Aspect 176] A compound in any one of aspects 153 to 164 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3. [Aspect 177] A compound in any one of aspects 153 to 164 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1 or 2. [Aspect 178] A compound in any one of aspects 165 to 167 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, 3, or 4. [Aspect 179] A compound in any one of aspects 165 to 167 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3. [Aspect 180] A compound in any one of aspects 165 to 167 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1 or 2.[Aspect 181] A compound in any one of aspects 168 to 171 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, 3, or 4. [Aspect 182] A compound in any one of aspects 168 to 171 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3. [Aspect 183] A compound in any one of aspects 168 to 171 in which the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1 or 2. [Aspect 184] In compound N of the present invention, R. 1 However, a compound which is a five-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group A. [Aspect 185] In compound N of the present invention, R 1A compound that is a six-membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from group A. [Aspect 186] A compound in which, in any of aspects 184 to 185, the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, 3, or 4. [Aspect 187] A compound in which, in any of aspects 184 to 185, the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3. [Aspect 188] A compound in which, in any of aspects 184 to 185, the heteroatoms constituting the aromatic heterocyclic group or the non-aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1 or 2. [Aspect 189] In any one of aspects 150 to 188, group A is a halogen atom, cyano group, nitro group, hydroxy group, amino group, formyl group, hydroxy group, aminocarbonyl group, aminosulfonyl group, C1-C6 alkyl group, C1-C6 alkenyl group, C1-C6 alkynyl group, C1-C6 alkoxy group, C2-C6 alkenyloxy group, C2-C6 alkynyloxy group, C1-C6 alkylthio group, C2-C6 alkenylthio group, C2-C6 alkynylthio group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, C 1-C6 alkylsulfinyl group, C2-C6 alkenylsulfinyl group, C2-C6 alkynylsulfinyl group, C1-C6 alkylsulfonyl group, C2-C6 alkenylsulfonyl group, C2-C6 alkynylsulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 alkyl group, the C1-C6 alkenyl group, the C1-C6 alkynyl group, the C1-C6 alkoxy group, the C2-C6 alkenyloxy group, the C2-C6 alkynyloxy group, the C1-C6 alkylthio group, the C2-C6 alkenylthio group, the C2-C6 alkynylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group,The (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C2-C6 alkenylsulfinyl group, the C2-C6 alkynylsulfinyl group, the C1-C6 alkylsulfonyl group, the C2-C6 alkenylsulfonyl group, the C2-C6 alkynylsulfonyl group, the (C1-C6 alkylamino) The sulfonyl group and the (C2-C8 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyloxy group, C3-C6 cycloalkenyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkenylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkenylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkenylsulfonyl group, C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {the C3-C6 cycloalkyloxy group, the C3-C6 cycloalkenyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkenylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, the C3-C6 cycloalkyl A lukenylsulfonyl group, the C3-C6 cycloalkyl group, and the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, a C6-C10 aryl group, a 5-10 member aromatic heterocyclic group, a 5-10 member non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-10 member aromatic heterocyclic group, and the 5-10 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R, 13 ) = N - OR 14Compounds comprising the group consisting of: [Aspect 190] In any one of aspects 150 to 188, group A is a halogen atom, cyano group, nitro group, hydroxy group, amino group, formyl group, hydroxy group, aminocarbonyl group, aminosulfonyl group, C1-C3 chain hydrocarbon group, C1-C3 alkoxy group, C2-C3 alkenyloxy group, C2-C3 alkynyloxy group, C1-C3 alkylthio group, C2-C3 alkenylthio group, C2-C3 alkynylthio group, C1-C3 alkylamino group, C2-C6 dialkylamino group, (C1-C3 alkyl)carbonyl group, (C1-C3 (C1-C3 alkylamino)carbonyl group, (C2-C6 dialkylamino)carbonyl group, C1-C3 alkylsulfinyl group, C2-C3 alkenylsulfinyl group, C2-C3 alkynylsulfinyl group, C1-C3 alkylsulfonyl group, C2-C3 alkenylsulfonyl group, C2-C3 alkynylsulfonyl group, (C1-C3 alkylamino)sulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, The C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the C2-C3 alkenylthio group, the C2-C3 alkynylthio group, the C1-C3 alkylamino group, the C2-C6 dialkylamino group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkylamino)carbonyl group, the (C2-C6 dialkylamino)carbonyl group, the C1-C3 alkylsulfinyl group, the C2-C3 alkenylsulfinyl group, the C2-C3 alkynylsulfinyl group, the C1-C3 alkylsulfonyl group The nyl group, the C2-C3 alkenylsulfonyl group, the C2-C3 alkynylsulfonyl group, the (C1-C3 alkylamino)sulfonyl group, and the (C2-C6 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyloxy group, C3-C6 cycloalkenyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkenylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkenylsulfinyl group, C3-C6 cycloalkylsulfonyl group,C3-C6 cycloalkenylsulfonyl group, C3-C6 alicyclic hydrocarbon group {the C3-C6 cycloalkyloxy group, the C3-C6 cycloalkenyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkenylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkenylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, the C3-C6 cycloalkenylsulfonyl group, and the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R, 13 ) = N - OR 14Compounds comprising the group consisting of: [Aspect 191] In any one of aspects 150 to 188, group A is a halogen atom, cyano group, nitro group, hydroxy group, amino group, formyl group, hydroxy group, aminocarbonyl group, aminosulfonyl group, C1-C3 alkyl group, C1-C3 alkenyl group, C1-C3 alkynyl group, C1-C3 alkoxy group, C2-C3 alkenyloxy group, C2-C3 alkynyloxy group, C1-C3 alkylthio group, C2-C3 alkenylthio group, C2-C3 alkynylthio group, C1-C3 alkylamino group, C2-C6 dialkylamino group, (C1-C 3 alkyl) carbonyl group, (C1-C3 alkoxy) carbonyl group, (C1-C3 alkylamino) carbonyl group, (C2-C6 dialkylamino) carbonyl group, C1-C3 alkyl sulfinyl group, C2-C3 alkenyl sulfinyl group, C2-C3 alkynyl sulfinyl group, C1-C3 alkyl sulfonyl group, C2-C3 alkenyl sulfonyl group, C2-C3 alkynyl sulfonyl group, (C1-C3 alkylamino) sulfonyl group, (C2-C6 dialkylamino) sulfonyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group , the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the C2-C3 alkenylthio group, the C2-C3 alkynylthio group, the C1-C3 alkylamino group, the C2-C6 dialkylamino group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the (C1-C3 alkylamino)carbonyl group, the (C2-C6 dialkylamino)carbonyl group, the C1-C3 alkylsulfinyl group, the C2-C3 alke The yl sulfinyl group, the C2-C3 alkynyl sulfinyl group, the C1-C3 alkyl sulfonyl group, the C2-C3 alkenyl sulfonyl group, the C2-C3 alkynyl sulfonyl group, the (C1-C3 alkylamino) sulfonyl group, and the (C2-C6 dialkylamino) sulfonyl group may be substituted with one or more substituents selected from group F, C3-C6 cycloalkyloxy group, C3-C6 cycloalkenyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkenylthio group, C3-C6 cycloalkyl sulfinyl group,C3-C6 cycloalkenylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkenylsulfonyl group, C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {the C3-C6 cycloalkyloxy group, the C3-C6 cycloalkenyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkenylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkenylsulfinyl group, the C3- C6 cycloalkylsulfonyl group, the C3-C6 cycloalkenylsulfonyl group, the C3-C6 cycloalkyl group, and the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 member aromatic heterocyclic group, 5-6 member non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-6 member aromatic heterocyclic group, and the 5-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R, 13 ) = N - OR 14Compounds comprising the group consisting of: [Aspect 192] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a nitro group, a formyl group, an aminosulfonyl group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C2-C3 alkenyloxy group, a C2-C3 alkynyloxy group, a C1-C3 alkylthio group, a C2-C3 alkenylthio group, a C2-C3 alkynylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C2-C3 alkenylsulfinyl group, a C2- C3 alkynylsulfinyl group, C1-C3 alkylsulfonyl group, C2-C3 alkenylsulfonyl group, C2-C3 alkynylsulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the C2-C3 alkenylthio group, the C2-C3 alkynylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 The alkylsulfinyl group, the C2-C3 alkenylsulfinyl group, the C2-C3 alkynylsulfinyl group, the C1-C3 alkylsulfonyl group, the C2-C3 alkenylsulfonyl group, the C2-C3 alkynylsulfonyl group, and the (C2-C6 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F, C3-C6 cycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 lipid Cyclic hydrocarbon group {The C3-C6 cycloalkyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {The C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14Compounds comprising the group consisting of: [Aspect 193] In any one of aspects 150 to 188, group A is a halogen atom, cyano group, nitro group, formyl group, aminosulfonyl group, C1-C3 alkyl group, C1-C3 alkenyl group, C1-C3 alkynyl group, C1-C3 alkoxy group, C2-C3 alkenyloxy group, C2-C3 alkynyloxy group, C1-C3 alkylthio group, C2-C3 alkenylthio group, C2-C3 alkynylthio group, (C1-C3 alkyl)carbonyl group, (C1-C3 alkoxy)carbonyl group, C1-C3 alkylsulfinyl group, C2-C3 alkenyl Sulfinyl group, C2-C3 alkynylsulfinyl group, C1-C3 alkylsulfonyl group, C2-C3 alkenylsulfonyl group, C2-C3 alkynylsulfonyl group, (C2-C6 dialkylamino)sulfonyl group {the C1-C3 alkyl group, the C1-C3 alkenyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the C2-C3 alkenylthio group, the C2-C3 alkynylthio group, the (C1-C3 alkyl)carbonyl group, the ( The (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, the C2-C3 alkenylsulfinyl group, the C2-C3 alkynylsulfinyl group, the C1-C3 alkylsulfonyl group, the C2-C3 alkenylsulfonyl group, the C2-C3 alkynylsulfonyl group, and the (C2-C6 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F, C3-C6 cycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkyl Sulfonyl group, C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group {The C3-C6 cycloalkyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 cycloalkyl group, the C3-C6 cycloalkenyl group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {The C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group are,} which may be substituted with one or more substituents selected from group G, and C(R, 13 ) = N - OR 14 Compounds comprising the group consisting of: [Aspect 194] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C3 alkenyloxy group, a C3 alkynyloxy group, a C1-C3 alkylthio group, a C3 alkenylthio group, a C3 alkynylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C3 alkenylsulfinyl group, a C3 alkyl Nyl sulfinyl group, C1-C3 alkylsulfonyl group, C3 alkenylsulfonyl group, C3 alkynylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C3 alkenyloxy group, the C3 alkynyloxy group, the C1-C3 alkylthio group, the C3 alkenylthio group, the C3 alkynylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group The C3 alkenyl sulfinyl group, the C3 alkynyl sulfinyl group, the C1-C3 alkyl sulfonyl group, the C3 alkenyl sulfonyl group, and the C3 alkynyl sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkyl sulfinyl group, C3-C6 cycloalkyl sulfonyl group, C3-C6 cycloalkyl {the C3-C6 cycloalkyl oxy C6 group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {the C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14A group consisting of the following. [Aspect 195] In any one of aspects 150 to 188, group A may be a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, or a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F. a) C3-C6 cycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkylalkyl group {The C3-C6 cycloalkyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {The C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14A compound comprising the group consisting of the following. [Aspect 196] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, and a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group are selected from group F. C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkylalkyl group {The C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {The C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14A compound comprising the group consisting of the following. [Aspect 197] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, and a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group are selected from group F. C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkylalkyl group {The C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, C6 aryl group, 5-6 membered aromatic heterocyclic group, 5-6 membered non-aromatic heterocyclic group {The C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14Compounds comprising the group consisting of: [Aspect 198] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group The nyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkylalkyl group {the C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, and the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, and C(R 13 ) = N - OR 14 Compounds comprising the group consisting of: [Aspect 199] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group , the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, C6 aryl group, 5-6 member aromatic heterocyclic group, 5-6 member non-aromatic heterocyclic group {the C6 aryl group, the 5-6 member aromatic heterocyclic group, and the 5-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14Compounds comprising the group consisting of: [Aspect 200] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C3 alkyl)carbonyl group, a (C1-C3 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, and C(R 13 ) = N - OR 14 Compounds comprising the group consisting of: [Aspect 201] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkynyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkynyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, a C6 aryl group, a 5-6 membered aromatic heterocyclic group, a 5-6 membered non-aromatic heterocyclic group {the C6 aryl group, the 5-6 membered aromatic heterocyclic group, and the 5-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R 13 ) = N - OR 14 Compounds comprising the group consisting of: [Aspect 202] In any one of aspects 150 to 188, group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, and C(R 13 ) = N - OR 14Compounds comprising the group consisting of the following. [Aspect 203] A compound in any one of aspects 150 to 188 in which group A is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, and a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}.

[0013] [Aspect A1] In compound N of the present invention, R 2 However, hydrogen atom, halogen atom, cyano group, C1-C3 chain hydrocarbon group, C1-C3 alkoxy group, C2-C3 alkenyloxy group, C2-C3 alkynyloxy group, C1-C3 alkylthio group, (C1-C3 alkyl)carbonyl group, (C1-C3 alkoxy)carbonyl group, C1-C3 alkylsulfinyl group, C1-C3 alkylsulfonyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 A compound comprising an alkylsulfinyl group and the C1-C3 alkylsulfonyl group, which may be substituted with one or more substituents selected from group F, a C3-C5 cycloalkyl group, a C3-C5 cycloalkyloxy group, a C3-C5 cycloalkylthio group, a C3-C5 cycloalkylsulfinyl group, or a C3-C5 cycloalkylsulfonyl group {the C3-C5 cycloalkyl group, the C3-C5 cycloalkyloxy group, the C3-C5 cycloalkylthio group, the C3-C5 cycloalkylsulfinyl group, and the C3-C5 cycloalkylsulfonyl group may be substituted with one or more substituents selected from group E}. [Aspect A2] A compound in which group F and group E are the same or different in phase, and are halogen atoms, in the present invention. [Aspect A3] In compound N of the present invention, R 2A compound in which R is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, or a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}. [Aspect A4] A compound in which group F is a halogen atom in aspect A3. [Aspect A5] A compound in which R is a halogen atom in aspect A1. 3 , R 4 , and R 5 A compound which is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}. [Aspect A6] In aspect A2, R 3 , R 4 , and R 5 However, a compound which is the same or different in phase, and is a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkyl group, or a C1-C3 alkoxy group {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}. [Aspect A7] In aspect A3, R 3 , R 4 , and R 5 A compound in which R is a hydrogen atom. [Aspect A8] In aspect A4, R 3 , R 4 , and R 5 A compound in which is a hydrogen atom. [Aspect A9] In aspect A5, Y 1 However, OR 10 NHS(O)2R 11 , or NHR 12 A compound that is [Aspect A10] In Aspect A6, Y 1 However, OR 10 NHS(O)2R 11 , or NHR 12 A compound that is [Aspect A11] In Aspect A7, Y 1 OR 10 A compound that is [Aspect A12] In Aspect A8, Y1 OR 10 A compound that is [Aspect A13] In Aspect A7, Y 1 OR 10 And R 10 However, the compound is a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J}. [Aspect A14] In aspect A8, Y 1 OR 10 And R 10 A compound comprising a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J}. [Aspect A15] In aspect A7, Y 1 OR 10 And R 10 However, a compound which is a C1-C6 alkyl group, benzyl group, or hydrogen atom that may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkoxy group, a halogen atom, and a cyano group. [Aspect A16] In aspect A8, Y 1 OR 10 And R 10 However, a compound which is a C1-C6 alkyl group, a benzyl group, or a hydrogen atom which may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkoxy group, a halogen atom, and a cyano group. [Aspect A17] In aspect A9, R 6 and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect A18] In aspect A10, R 6 and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect A19] In aspect A11, R 6 and R 7However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect A20] In aspect A12, R 6 and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect A21] In aspect A13, R 6 and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect A22] In aspect A14, R 6 and R 7 However, a compound which is the same or different in phase, and is a hydrogen atom or a halogen atom. [Aspect A23] In compound N of the present invention, R 6 and R 7 A compound in which is a hydrogen atom. [Aspect A24] In aspect A11, R 6 and R 7 A compound in which is a hydrogen atom. [Aspect A25] In aspect A12, R 6 and R 7 A compound in which R is a hydrogen atom. [Aspect A26] In aspect A13, R 6 and R 7 A compound in which R is a hydrogen atom. [Aspect A27] In aspect A14, R 6 and R 7 A compound in which R is a hydrogen atom. [Aspect A28] In aspect A15, R 6 and R 7 A compound in which is a hydrogen atom. [Aspect A29] In aspect A16, R 6 and R 7 A compound in which is a hydrogen atom. [Aspect A30] In aspect A17, X 1 and X 2 A compound in which is an oxygen atom. [Aspect A31] In aspect A18, X 1 and X 2 A compound in which is an oxygen atom. [Aspect A32] In aspect A19, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A33] In aspect A20, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A34] In Aspect A21, X 1 and X 2A compound in which X is an oxygen atom. [Aspect A35] In aspect A22, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A36] In Aspect A23, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A37] In Aspect A24, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A38] In Aspect A25, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A39] In Aspect A26, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A40] In Aspect A27, X 1 and X 2 A compound in which is an oxygen atom. [Aspect A41] In Aspect A28, X 1 and X 2 A compound in which X is an oxygen atom. [Aspect A42] In Aspect A29, X 1 and X 2 A compound in which is an oxygen atom. [Aspect A43] In any one of aspects A1 to A42, R 1A compound having a 5-9 membered heterocyclic group which may be substituted with one or more substituents selected from group A {the heteroatoms constituting the 5-9 membered heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3}. [Aspect A44] A compound in which group A is a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a (C1-C6 alkoxy)carbonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}. [Aspect A45] In any one of aspects A1 to A42, R 1 A compound comprising a 5-6 member aromatic heterocyclic group which may be substituted with one or more substituents selected from group A {the heteroatoms constituting the 5-6 member aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of such heteroatoms is 1, 2, or 3}. [Aspect A46] A compound in which group A is a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a (C1-C6 alkoxy)carbonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}. [Aspect A47] In any one of aspects A1 to A42 or compound N of the present invention, R 1However, pyrrolyl group, furyl group, thienyl group, pyrazolyl group, imidazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, pyridyl group, pyrimidinyl group, pyridadinyl group, pyrazinyl group, benzoxazolyl group, benzothiazolyl group, pyrazolopyridyl group, tetrahydrobenzothiazolyl group, tetrahydrofuranyl group, tetrahydropyranyl group, or piperidyl group {the pyrrolyl group, the furyl group, the thienyl group, the pyrazolyl group, A compound in which the imidazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the triazolyl group, the oxadiazolyl group, the thiadiazolyl group, the pyridyl group, the pyrimidinyl group, the pyridadinyl group, the pyrazinyl group, the benzoxazolyl group, the benzothiazolyl group, the pyrazolopyridyl group, the tetrahydrobenzothiazolyl group, the tetrahydrofuranyl group, the tetrahydropyranyl group, and the piperidyl group may be substituted with one or more substituents selected from group A. [Aspect A48] A compound in which group A is a group consisting of a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a (C1-C6 alkoxy)carbonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}.[Aspect A49] A compound in which group A is a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C6 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a phenyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C6 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, the C1-C3 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}. [Aspect A50] In any one of aspects A1 to A42 or compound N of the present invention, R. 1A compound wherein the compound is a thienyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a pyridyl group, a pyrimidinyl group, a pyridadinyl group, a benzoxazolyl group, a benzothiazolyl group, a pyrazolopyridyl group, a tetrahydrobenzothiazolyl group, a tetrahydrofuranyl group, a tetrahydropyranyl group, or a piperidyl group {the thienyl group, the pyrazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the pyridyl group, the pyrimidinyl group, the pyridadinyl group, the benzoxazolyl group, the benzothiazolyl group, the pyrazolopyridyl group, the tetrahydrobenzothiazolyl group, the tetrahydrofuranyl group, the tetrahydropyranyl group, and the piperidyl group may be substituted with one or more substituents selected from group A}. [Aspect A51] A compound in which group A is a group consisting of a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a (C1-C6 alkoxy)carbonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}.[Aspect A52] A compound in which group A in aspect A50 is a group consisting of a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a (C1-C6 alkoxy)carbonyl group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a phenyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C6 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, the C1-C3 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}. [Aspect A53] In any one of aspects A1 to A42 or compound N of the present invention, R. 1A compound having a furyl group, a thienyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridadinyl group {the furyl group, the thienyl group, the pyrazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the pyridyl group, the pyrimidinyl group, and the pyridadinyl group may be substituted with one or more substituents selected from group A}. [Aspect A54] A compound in which group A is a group consisting of a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}. [Aspect A55] A compound in which group A in aspect A53 is a group consisting of a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a phenyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, the C1-C3 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}. [Aspect A56] In any one of aspects A1 to A42 or compound N of the present invention, R 1A compound having a thienyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridadinyl group {the thienyl group, the pyrazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the pyridyl group, the pyrimidinyl group, and the pyridadinyl group may be substituted with one or more substituents selected from group A}. [Aspect A57] A compound in which group A is a group consisting of a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}. [Aspect A58] A compound in which group A in aspect A56 is a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a phenyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, the C1-C3 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups}. [Aspect A59] In any one of aspects A1 to A42 or compound N of the present invention, R 1A compound having a thienyl group, a pyrazolyl group, a thiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridadinyl group {the thienyl group, the pyrazolyl group, the thiazolyl group, the pyridyl group, the pyrimidinyl group, and the pyridadinyl group may be substituted with one or more substituents selected from group A}. [Aspect A60] A compound in which group A in aspect A59 is a group consisting of a halogen atom, a cyano group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a phenyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}. [Aspect A61] A compound in which group A is a group consisting of a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a phenyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, the C1-C3 alkylsulfonyl group, and the phenyl group may be substituted with one or more halogen atoms}, and a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}.

[0014] Next, the method for producing the compound of the present invention and its intermediate will be described.

[0015] Manufacturing Method A-1 The compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting the compound represented by formula (A1) (hereinafter referred to as compound (A1)) in the presence of water and a base. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and 1,4-dioxane (hereinafter referred to as ethers); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); and mixtures of two or more of these. The solvent may be mixed with water and used in the reaction, or water may be used as the solvent. Examples of bases used in the reaction include organic bases such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undeca-7-ene (DBU), pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as alkali metal bicarbonates); alkaline earth metal carbonates such as magnesium carbonate and calcium carbonate (hereinafter referred to as alkaline earth metal carbonates); metal carboxylates such as sodium acetate, potassium acetate, calcium acetate, and magnesium acetate (hereinafter referred to as metal carboxylates); and metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide (hereinafter referred to as metal hydroxides). In the reaction, the base is usually used in a ratio of 1 to 10 moles per mole of compound (A1). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture can be made acidic by adding an inorganic acid such as hydrochloric acid or sulfuric acid, then extracted with an organic solvent, and the organic layer can be isolated by post-treatment operations such as drying and concentrating. Alternatively, after the reaction is complete, water and MTBE can be added to the reaction mixture, and then extracted with an aqueous sodium hydroxide solution to obtain an aqueous layer. Next, the aqueous layer can be made acidic by adding an inorganic acid such as hydrochloric acid or sulfuric acid, then extracted with an organic solvent, and the organic layer can be isolated by post-treatment operations such as drying and concentrating.

[0016] Manufacturing method A-2 Compound (I-1) can also be produced by reacting compound (A1) in the presence of a lithium salt and an amine. [In the formula, the symbols have the same meaning as above.] The reaction can be carried out in accordance with the method described in Tetrahedron Letters 2007, 48, 2497-2499.

[0017] Manufacturing method A-3 Compound (I-1) can also be produced by reacting compound (A1) in the presence of water and an acid. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons such as toluene, xylene, and hexane (hereinafter referred to as hydrocarbons); ethers; halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); and mixtures of two or more of these. The solvent may be mixed with water and used in the reaction, or water may be used as the solvent. Examples of acids used in the reaction include sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid (hereinafter referred to as sulfonic acids); inorganic acids such as hydrochloric acid and sulfuric acid (hereinafter referred to as inorganic acids); and carboxylic acids such as acetic acid and trifluoroacetic acid (hereinafter referred to as carboxylic acids). In the reaction, the acid is usually used in a ratio of 0.001 to 10 moles per mole of compound (A1). The reaction temperature is usually in the range of -20 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture can be mixed with water, extracted with an organic solvent, and the organic layer can be dried and concentrated to isolate compound (I-1).

[0018] Manufacturing Method B The compound represented by formula (I-2) (hereinafter referred to as compound (I-2)) can be produced by reacting the compound represented by formula (A2) (hereinafter referred to as compound (A2)) and the compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a base. [In the formula, L 1The symbols represent substituents such as chlorine atoms, bromine atoms, iodine atoms, methanesulfonyloxy groups, 4-methylbenzenesulfonyloxy groups, or trifluoromethanesulfonyloxy groups, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides such as N,N-dimethylformamide (hereinafter referred to as DMF); imidazolinones such as 1,3-dimethyl-2-imidazolinone; sulfoxides such as dimethyl sulfoxide (hereinafter referred to as DMSO); nitriles such as acetonitrile; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal bicarbonates; metal carboxylates; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium methoxide, and potassium t-butoxide (hereinafter referred to as metal alkoxides); metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride (hereinafter referred to as metal hydrides); and metal hydroxides. In the reaction, compound (M1) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A2). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-2) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M1) is commercially available or can be manufactured according to known methods.

[0019] Manufacturing Method C The compound represented by formula (I-3) (hereinafter referred to as compound (I-3)) can also be manufactured by a step (step C-1) in which a compound represented by formula (A3) (hereinafter referred to as compound (A3)) is reacted with a chlorinating agent to obtain a compound represented by formula (IM-3) (hereinafter referred to as compound (IM-3)), and a step (step C-2) in which compound (IM-3) obtained in step C-1 is reacted with a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a base. [In the formula, the symbols have the same meaning as above.]

[0020] First, step C-1 will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; esters such as ethyl acetate (hereinafter referred to as esters); and mixtures of two or more of these. Examples of chlorinating agents used in the reaction include thionyl chloride, oxalyl chloride, oxy, and phosphorus chloride. Such chlorinating agents are usually used in a ratio of 1 to 10 moles per mole of compound (A3). The reaction may also be carried out in the presence of a catalyst. An example of a catalyst is DMF. When the reaction is carried out in the presence of a catalyst, the catalyst is usually used in a ratio of 0.01 to 1 mole per mole of compound (A3). The reaction temperature is usually in the range of -80 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (IM-3) can be isolated by performing a work-up operation. Alternatively, the reaction mixture after the reaction is complete may be used directly in step C-2, or the mixture obtained by concentrating the reaction mixture may be used in step C-2.

[0021] Next, step C-2 will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; esters; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkaline earth metal carbonates; alkali metal carbonates; alkali metal bicarbonates; metal carboxylates; and metal hydroxides. In the reaction, compound (M2) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A3) used in step C-1. The reaction temperature is usually in the range of -80 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-3) can be isolated by mixing the reaction mixture with water, extracting it with an organic solvent, and performing post-treatment operations such as washing, drying, and concentrating the organic layer. Note that the reaction conditions (solvent, reaction temperature, reaction time, etc.) for step C-1 and step C-2 may be the same or different. Furthermore, steps C-1 and C-2 may be carried out simultaneously by mixing compound (A3), chlorinating agent, base, and compound (M2), or step C-1 may be carried out first, followed by step C-2. Alternatively, step C-2 may be started between the start and finish of step C-1.

[0022] Manufacturing Method D The compound represented by formula (I-4) (hereinafter referred to as compound (I-4)), the compound represented by formula (I-5) (hereinafter referred to as compound (I-5)), and the compound represented by formula (I-6) (hereinafter referred to as compound (I-6)) can be produced by reacting the compound represented by formula (A4) (hereinafter referred to as compound (A4)) with a sulfurizing agent. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, and mixtures of two or more of these. Examples of sulfiding agents used in the reaction include phosphorus pentasulfide and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosfetan-2,4-disulfide (hereinafter referred to as Lawson's reagent). In the reaction, the sulfiding agent is usually used in a ratio of 1 to 10 moles per mole of compound (A4). The reaction temperature is usually in the range of -20 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture is mixed with water, extracted with an organic solvent, and the organic layer is dried and concentrated to isolate compound (I-4), compound (I-5), or compound (I-6). By adjusting the type of solvent and sulfiding agent, the equivalent amount of sulfiding agent, the reaction temperature, and the reaction time, the proportions of compound (I-4), compound (I-5), and compound (I-6) produced can be increased or decreased.

[0023] Manufacturing Method E The compound represented by formula (I-7) (hereinafter referred to as compound (I-7)) can be produced by reacting the compound represented by formula (A5) (hereinafter referred to as compound (A5)) and the compound represented by formula (M3) (hereinafter referred to as compound (M3)) in the presence of a catalyst and a base. [During the ceremony, W 1 represents a leaving group such as a chlorine atom, bromine atom, iodine atom, or trifluoromethanesulfonyloxy group, M 3 This is an alkoxyboranyl group such as B(OH)2,4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, or a trifluoroborate salt (BF3 - K + ) represents R 2xrepresents a C2-C6 alkenyl group, a C3-C8 cycloalkenyl group, a C3-C8 cycloalkyl group {the C2-C6 alkenyl group, the C3-C8 cycloalkenyl group, and the C3-C8 cycloalkyl group may be substituted with one or more substituents selected from group F}, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, and a 5-10 membered non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-10 membered aromatic heterocyclic group, and the 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; water; and mixtures of two or more of these. Examples of palladium catalysts used in the reaction include tetrakistriphenylphosphine palladium (0), palladium acetate (II), tris(dibenzylideneacetone)dipalladium, and [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal bicarbonates, alkaline earth metal carbonates, sodium fluoride, and tripotassium phosphate. In the reaction, compound (M3) is usually used in a ratio of 1 to 10 moles, catalyst in a ratio of 0.01 to 1 mole, and base in a ratio of 1 to 10 moles per mole of compound (A5). The reaction temperature is usually in the range of 0 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-7) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it.

[0024] Manufacturing Method E-2 The compound represented by formula (I-7-2) (hereinafter referred to as compound (I-7-2)) can be produced by reacting the compound represented by formula (A5-2) (hereinafter referred to as compound (A5-2)) and the compound represented by formula (M3-2) (hereinafter referred to as compound (M3-2)) in the presence of a catalyst and a base. [In the formula, R 3arepresents a C2-C6 alkenyl group, a C3-C8 cycloalkenyl group, a C3-C8 cycloalkyl group {the C2-C6 alkenyl group, the C3-C8 cycloalkenyl group, and the C3-C8 cycloalkyl group may be substituted with one or more substituents selected from group F}, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, or a 5-10 membered non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-10 membered aromatic heterocyclic group, and the 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and other symbols have the same meaning as above. The reaction can be carried out in accordance with manufacturing method E, using compound (A5-2) instead of compound (A5) and compound (M3) instead of compound (M3).

[0025] Manufacturing Method E-3 The compound represented by formula (I-7-3) (hereinafter referred to as compound (I-7-3)) can be produced by reacting the compound represented by formula (A5-3) (hereinafter referred to as compound (A5-3)) and the compound represented by formula (M3-3) (hereinafter referred to as compound (M3-3)) in the presence of a catalyst and a base. [In the formula, R 4a represents a C2-C6 alkenyl group, a C3-C8 cycloalkenyl group, a C3-C8 cycloalkyl group {the C2-C6 alkenyl group, the C3-C8 cycloalkenyl group, and the C3-C8 cycloalkyl group may be substituted with one or more substituents selected from group F}, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, or a 5-10 membered non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-10 membered aromatic heterocyclic group, and the 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and other symbols have the same meaning as above. The reaction can be carried out in accordance with manufacturing method E, using compound (A5-3) instead of compound (A5) and compound (M3) instead of compound (M3).

[0026] Manufacturing Method E-4 The compound represented by formula (I-7-4) (hereinafter referred to as compound (I-7-4)) can be produced by reacting the compound represented by formula (A5-4) (hereinafter referred to as compound (A5-4)) and the compound represented by formula (M3-4) (hereinafter referred to as compound (M3-4)) in the presence of a catalyst and a base. [In the formula, R 5a represents a C2-C8 alkenyl group, a C3-C8 cycloalkenyl group, a C3-C8 cycloalkyl group {the C2-C8 alkenyl group, the C3-C8 cycloalkenyl group, and the C3-C8 cycloalkyl group may be substituted with one or more substituents selected from group F}, a C6-C10 aryl group, a 5-10 member aromatic heterocyclic group, or a 5-10 member non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-10 member aromatic heterocyclic group, and the 5-10 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and other symbols have the same meaning as above. The reaction can be carried out in accordance with manufacturing method E, using compound (A5-4) instead of compound (A5) and compound (M3) instead of compound (M3).

[0027] Compounds (M3), (M3-2), (M3-3), and (M3-4) are commercially available compounds or can be produced by methods described in or in accordance with Chemical Reviews, Vol. 95, pp. 2457-2483 (1995), etc. Boronic acid derivatives can also be produced by hydrolyzing the boronic acid ester derivatives obtained by these methods or commercially available boronic acid ester derivatives as needed. Furthermore, trifluoroborate salts (BF3) can be produced by fluorinating the boronic acid ester derivatives in accordance with methods described in Accounts of Chemical Research, Vol. 40, pp. 275-286 (2007), etc. - K + ) can also be obtained.

[0028] Manufacturing Method F The compound represented by formula (I-8) (hereinafter referred to as compound (I-8)) can be produced by reacting compound (A5) and the compound represented by formula (M4) (hereinafter referred to as compound (M4)) in the presence of a catalyst and a base. [In the formula, R 2Yrepresents a C2-C6 alkynyl group {the C2-C6 alkynyl group may be substituted with one or more substituents selected from group F}, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of catalysts used in the reaction include palladium catalysts such as tetrakistriphenylphosphine palladium (O), palladium acetate (II), tris(dibenzylideneacetone) dipalladium, and [1,1'-bis(diphenylphosphine)ferrocene]palladium (II) dichloride; and copper catalysts such as copper iodide and copper chloride. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal bicarbonates; metal carboxylates; metal alkoxides; and metal hydroxides. The reaction typically uses 1 to 10 moles of compound (M4), 0.01 to 1 mole of catalyst, and 1 to 10 moles of base per mole of compound (A5). Ligands may also be used in the reaction as needed. Examples of ligands include triphenylphosphine, xanthophos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, and 1,2-bis(diphenylphosphino)ethane. When ligands are used in the reaction, they are typically used in a ratio of 0.01 to 1 mole of ligand per mole of compound (A5). The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-8) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M4) is either a commercially available compound or can be produced according to the methods described in Tetrahedron Lett. 1972, 13, 3769, Synlett 1996, 521, etc.

[0029] Manufacturing Method G-1 The compound represented by formula (I-9) (hereinafter referred to as compound (I-9)) can be produced by reacting the compound represented by formula (A6) (hereinafter referred to as compound (A6)) and the compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base. [In the formula, R 2c is a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, Z 2c represents an oxygen atom or a sulfur atom, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; imidazolinones; sulfoxides; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal bicarbonates; metal carboxylates; metal alkoxides; metal hydrides; and metal hydroxides. In the reaction, compound (M5) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A6). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-9) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M5) can be a commercially available compound or can be manufactured according to known methods.

[0030] Manufacturing Method G-2 The compound represented by formula (I-10) (hereinafter referred to as compound (I-10)) can also be produced by reacting the compound represented by formula (A7) (hereinafter referred to as compound (A7)) and the compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base. [During the ceremony, W 2 R is a leaving group such as a fluorine atom, a chlorine atom, a bromine atom, or a trifluoromethanesulfonyloxy group. 2drepresents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, and a C6-C10 aryl group {the C6-C10 aryl group may be substituted with one or more substituents selected from group G}, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; imidazolinones; sulfoxides; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal bicarbonates; metal carboxylates; metal alkoxides; metal hydrides; and metal hydroxides. In the reaction, compound (M6) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A7). The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-10) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M6) can be a commercially available compound or can be produced according to known methods.

[0031] Reference Manufacturing Method H The compound represented by formula (A11) (hereinafter referred to as compound (A11)) can be produced by reacting the compound represented by formula (A8) (hereinafter referred to as compound (A8)) with a diazotizing agent in the presence of a base. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; and mixtures of two or more of these. Examples of diazotizing agents used in the reaction include 4-methylbenzenesulfonyl azide, 4-acetamidobenzenesulfonate azide, 4-dodecylbenzenesulfonate azide, methanesulfonyl azide, imidazole-1-sulfonyl azide hydrochloride, and 2-azide-1,3-dimethylimidazolinium hexafluorophosphate. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal bicarbonates; metal carboxylates; metal alkoxides; metal hydroxides; and metal hydrides. The reaction typically involves using 1 to 10 moles of diazotizing agent and 1 to 10 moles of base per mole of compound (A8). The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, compound (A11) can be isolated by mixing the reaction mixture with water, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.

[0032] Reference Manufacturing Method I: The compound represented by formula (A12) (hereinafter referred to as compound (A12)) can be produced by reacting compound (A11) with a reducing agent. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; and mixtures of two or more of these. Examples of reducing agents used in the reaction include triphenylphosphine and tributylphosphine. In the reaction, the reducing agent is usually used in a ratio of 1 to 10 moles per mole of compound (A11). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (A12) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it. Note that compound (A12) can also be used in the next step without being isolated from the reaction mixture.

[0033] The compound represented by formula (A13) in the reference manufacturing method J (hereinafter referred to as compound (A13)) can be produced by reacting compound (A12) in the presence of a base. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; metal bicarbonates; alkaline earth metal carbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, the base is usually used in a ratio of 1 to 10 moles per mole of compound (A12). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (A13) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it.

[0034] Manufacturing method K-1 The compound represented by formula (I-14) (hereinafter referred to as compound (I-14)) can be produced by reacting compound (A13) and the compound represented by formula (M7) (hereinafter referred to as compound (M7)) in the presence of a base. [In the formula, L 2 The symbols represent leaving groups such as fluorine, chlorine, bromine, iodine, methanesulfonyloxy, 4-methylbenzenesulfonyloxy, and trifluoromethanesulfonyloxy, while the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; metal bicarbonates; alkaline earth metal carbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, compound (M7) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A13). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-14) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting it with an organic solvent, and drying and concentrating the organic layer. Compound (M7) is either a commercially available compound or can be produced according to known methods.

[0035] Manufacturing method K-2 Compound (I-14) can also be produced by reacting compound (A12) and compound (M7) in the presence of a base. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; metal bicarbonates; alkaline earth metal carbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, compound (M7) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A12). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-14) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it.

[0036] Manufacturing method L-1 Compound (A8) can be produced by reacting the compound represented by formula (A9) (hereinafter referred to as compound (A9)) with the compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; metal bicarbonates; alkaline earth metal carbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, compound (M8) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A9). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (A7) can be isolated by post-treatment operations such as mixing the reaction mixture with hydrochloric acid water, extracting with an organic solvent, drying the organic layer, and concentrating it. Compounds (A9) and (M8) are commercially available compounds or can be produced according to known methods.

[0037] Manufacturing Method L-2 Compound (A8) can also be manufactured by a step (Step L-2-1) in which compound (A10) is reacted with a chlorinating agent to obtain a compound represented by formula (IM10) (hereinafter referred to as compound (IM10)), and a step (Step L-2-2) in which compound (IM10) obtained in Step L-2-1 is reacted with a compound represented by formula (M9) (hereinafter referred to as compound (M9)), or a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a Lewis acid and a base, and then reacted with an acidic aqueous solution to decarboxylate it. [In the formula, the symbols have the same meaning as above.]

[0038] First, step L-2-1 will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; and mixtures of two or more of these. Examples of chlorinating agents used in the reaction include thionyl chloride, oxalyl chloride, phosphorus oxychloride, triphosgene, diphosgene, phosgene, and sulfuryl chloride. Such chlorinating agents are usually used in a ratio of 1 to 10 moles per mole of compound (A10). The reaction may also be carried out in the presence of a catalyst. An example of a catalyst is DMF. When the reaction is carried out in the presence of a catalyst, the catalyst is usually used in a ratio of 0.01 to 1 mole per mole of compound (A10). The reaction temperature is usually in the range of -80 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (IM10) can be isolated by workup. Alternatively, the reaction mixture after the reaction is complete may be used directly in step L-2-2, or the mixture obtained by concentrating the reaction mixture may be used in step L-2-2.

[0039] Next, step L-2-2 will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; esters; and mixtures of two or more of these. Examples of Lewis acids used in the reaction include magnesium chloride and magnesium ethoxide. Examples of bases used in the reaction include organic bases; alkaline earth metal carbonates; alkali metal carbonates; alkali metal bicarbonates; metal carboxylates; and metal hydroxides. In the reaction, compound (M9) or compound (M10) is usually used in a ratio of 1 to 10 moles, Lewis acid in a ratio of 1 to 10 moles, and base in a ratio of 1 to 10 moles per mole of compound (A10). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours.

[0040] Next, the resulting reaction mixture is mixed with an acidic aqueous solution (e.g., hydrochloric acid) to cause decarboxylation and produce compound (A8). After the reaction is complete, compound (A8) can be isolated by extracting the reaction mixture with an organic solvent and performing post-treatment operations such as washing, drying, and concentrating the organic layer. The reaction conditions (solvent, reaction temperature, reaction time, etc.) for steps L-2-1 and L-2-2 may be the same or different. Steps L-2-1 and L-2-2 may be carried out simultaneously by mixing compound (A10), a chlorinating agent, a base, a Lewis acid, and compound (M9) or compound (M10), or step L-2-1 may be carried out first and then step L-2-2. Alternatively, step L-2-2 may be started between the start and finish of step L-2-1. Compounds (M9) and (M10) are commercially available compounds or can be produced according to known methods.

[0041] Manufacturing Method M The compound represented by formula (I-16) (hereinafter referred to as compound (I-16)) and the compound represented by formula (I-17) (hereinafter referred to as compound (I-17)) can be produced by reacting the compound represented by formula (I-15) (hereinafter referred to as compound (I-15)) with an oxidizing agent. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of oxidizing agents used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, tert-butyl peroxide, cumene hydroperoxide, peracetic acid, trifluoroperacetic acid, 3-chloroperbenzoic acid, magnesium monoperoxyphthalate hexahydrate, dimethyldioxirane, etc. In the reaction, the oxidizing agent is usually used in a ratio of 0.5 to 5 moles per mole of compound (I-15). When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be used as needed. When a base is used in the reaction, an example of a base is sodium carbonate, and the base is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-15). When a catalyst is used in the reaction, for example, sodium tungstate is used as the catalyst, and typically 0.01 to 0.5 moles of the catalyst are used per mole of compound (I-15). The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture is mixed with a reducing agent such as an aqueous sodium sulfite solution, extracted with an organic solvent, and the organic layer is dried and concentrated to isolate compound (I-16) or compound (I-17).

[0042] Manufacturing Method N The compound represented by formula (I-19) (hereinafter referred to as compound (I-19)) and the compound represented by formula (I-20) (hereinafter referred to as compound (I-20)) can be produced by reacting the compound represented by formula (I-18) (hereinafter referred to as compound (I-18)) with an oxidizing agent. [In the formula, R 15is a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, or a C3-C6 cycloalkyl group {the C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, or C3-C6 cycloalkyl group may be substituted with one or more substituents selected from group E}, Het is a 5-10 membered aromatic heterocycle or a 3-10 membered non-aromatic heterocycle, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of oxidizing agents used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, peracetic acid, trifluoroperacetic acid, 3-chloroperbenzoic acid, magnesium monoperoxyphthalate hexahydrate, and dimethyldioxirane. Typically, 0.5 to 5 moles of the oxidizing agent are used per mole of compound (I-18). When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be used as needed. When a base is used, for example, sodium carbonate is used, typically in a ratio of 0.01 to 1 mole of the base per mole of compound (I-18). When a catalyst is used, for example, sodium tungstate is used, typically in a ratio of 0.01 to 0.5 moles of the catalyst per mole of compound (I-18). The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture can be mixed with a reducing agent such as an aqueous sodium sulfite solution, extracted with an organic solvent, and then the organic layer can be dried and concentrated to isolate compound (I-19) or compound (I-20).

[0043] Manufacturing Method O-1 The compound represented by formula (I-21) (hereinafter referred to as compound (I-21)) can be produced by reacting compound (A13) and the compound represented by formula (M11) (hereinafter referred to as compound (M11)) in the presence of a base. [In the formula, L 3X represents a leaving group such as a fluorine atom, chlorine atom, bromine atom, or iodine atom. 3 represents an oxygen atom or a sulfur atom, and other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; metal bicarbonates; alkaline earth metal carbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, compound (M11) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A13). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-21) can be isolated by mixing the reaction mixture with water, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (M11) is either a commercially available compound or can be produced according to known methods.

[0044] Manufacturing method O-2 Compound (I-21) can also be produced by reacting compound (A12) and compound (M11) in the presence of a base. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; metal bicarbonates; alkaline earth metal carbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, compound (M11) is usually used in a ratio of 1 to 10 moles and base in a ratio of 1 to 10 moles per mole of compound (A12). The reaction temperature is usually in the range of -20 to 200°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-21) can be isolated by post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, drying the organic layer, and concentrating it.

[0045] Manufacturing Method O-3 The compound represented by formula (I-24) (hereinafter referred to as compound (I-24)) can be produced by reacting compound (I-22) with a methylene agent. [In the formula, the symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, and mixtures of two or more of these. Examples of methylene agents used in the reaction include μ-chloro-μ-methylene[bis(cyclopentadienyl)titanium]dimethylaluminum (hereinafter referred to as Tebbe reagent), bis(cyclopentadienyl)dimethyltitanium (hereinafter referred to as Petasis reagent), or methyltriphenylphosphonium bromide. In the reaction, the methylene agent is usually used in a ratio of 1 to 10 moles per mole of compound (I-22). When methyltriphenylphosphonium bromide is used as the methylene agent, compound (I-24) can be produced by reacting it with a base. Examples of bases used in the reaction include n-butyllithium, and the base is usually used in a ratio of 1 to 10 moles per mole of compound (I-22). The reaction temperature is typically in the range of -78 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture is mixed with water, extracted with an organic solvent, and the organic layer is dried and concentrated to isolate compound (I-24).

[0046] The compound of the present invention can be mixed with or used in combination with one or more components selected from the groups (a), (b), (c), (d), (e), and (f) below (hereinafter referred to as "the component"). Mixing or used in combination means using the compound of the present invention and the component simultaneously, separately, or at intervals of time. When the compound of the present invention and the component are used simultaneously, the compound of the present invention and the component may be contained in separate formulations or in a single formulation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the groups (d) and (f) below (i.e., the component), and the compound of the present invention.

[0047] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, string organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncoupling agents, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, This group consists of inhibitors of III and IV, voltage-gated sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chord-sound organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal components. These are described in the IRAC classification based on the mechanism of action.

[0048] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., anilinopyridine fungicides), signaling inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., triazole-based DMI fungicides), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-point contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These are described in the FRAC classification based on mechanism of action.

[0049] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).

[0050] Group (d) is the group of ingredients that reduce drug-induced harm.

[0051] Group (e) is a group of synergistic agents that enhance the efficacy of other drugs when used in combination.

[0052] Group (f) consists of acetyl-CoA carboxylase (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, photosynthesis (photosystem II) inhibitors, photosystem I electron converters, protoporphyrinogen oxidase (PPO) inhibitors, phytoene desaturation system (PDS) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors, carotenoid biosynthesis inhibitors, EPSP synthase inhibitors, glutamine synthase inhibitors, dihydropteroic acid (DHP) synthase inhibitors, microtubule polymerization inhibitors, mitosis / microtubule formation inhibitors, very long-chain fatty acid (VLCFA) inhibitors, cellulose synthesis inhibitors, uncoupling agents, lipid synthesis inhibitors, indoleacetic acid-like activators, auxin transfer inhibitors, and other herbicidal active ingredients. These are described in the classification based on the mechanism of action of HRAC.

[0053] Examples of combinations of this component and the compounds of the present invention are described below. For example, alanycarb + SX means a combination of alanycarb and SX. The abbreviation SX means any one of the compounds of the present invention selected from the compound group SX1 to SX335 and the compounds of the present invention 1 to 121, which will be described later. Furthermore, all of the components of this component described below are known components and can be obtained from commercially available formulations or manufactured by known methods. If the component is a microorganism, it can also be obtained from a microbial depositary. The numbers in parentheses represent CAS RN (registered trademark).

[0054] Combinations of the above group (a) components with the compounds of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Bentioflumin + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX,Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Bisulflufen + SX, Borax + SX, Boric acid + SX, Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium phosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride + SX, Cartap + SX, Chinomethionate + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chloropicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chromafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanamycin A + SX, Coumaphos + SX, Cryolite + SX,Cyanophos + SX, Cyantraniliprole + SX, Cybenzoxasulfyl + SX, Cyclaniliprole + SX, Cyclobutrifluram + SX, Cycloprothrin + SX, Cycloxaprid + SX, Cyenopyrafen + SX, Cyetpyrafen + SX, Cyflumetofen + SX, Cyfluthrin + SX, Cyhalodiamide + SX, Cyhalothrin + SX, Cyhexatin + SX, Cypermethrin + SX, Cyphenothrin + SX, Cyproflanilide + SX, Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-methyl + SX, Diafenthiuron + SX, Diazinon + SX, Dichlorvos + SX, Dichloromezotiaz + SX, Dicofol + SX, Diclotophos + SX, Diflovidazin + SX, Diflubenzuron + SX, Dimefluthrin + SX, Dimethoate + SX, Dimethylvinphos + SX, Dimpropyridaz + SX, Dinotefuran + SX, Disodium octaborate + SX,Disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, dried leaves of Dryopteris filix-mas + SX, emamectin-benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethiofencarb + SX, ethion + SX, Ethiprole + SX, Ethoprophos + SX, Etofenprox + SX, Ethoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX Mistletoe extract (extract of Viscum album) + SX,Fanflu + SX, Fenamiphos + SX, Fenazaquin + SX, Fenbutatin oxide + SX, Fenitrothion + SX, Fenmezoditiaz + SX, Fenobucarb + SX, Fenoxycarb + SX, Fenpropathrin + SX, Fenpyroximate + SX, Fenthion + SX, Fenvalerate + SX, Fipronil + SX, Flometoquin + SX, Flonicamid + SX, Fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX,Formetanate + SX, Fosthiazate + SX, Furamethrin + SX, Furathiocarb + SX, Gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, Halfenprox + SX, Halofenozide + SX, Heptafluthrin + SX, Heptenophos + SX, Hexaflumuron + SX, Hexythiazox + SX, Potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflualanam + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, Isoxathion + SX, Ivermectin + SX, Cadesrin + SX, Kappatefluthrin + SX, Kappa-bifenthrin + SX,Kinoprene + SX, lambda-cyhalothrin + SX, Ledprona + SX, Lenoremycin + SX, Lepimectin + SX, Lime sulfur + SX, Lotilaner + SX, Lufenuron + SX, Machine oil + SX, Malathion + SX, Mecarbam + SX, Meperfluthrin + SX, Metaflumizone + SX, Metam + SX, Methamidophos + SX, Methidathion + SX, Methiocarb + SX, Methomyl + SX, Methoprene + SX, Methoxychlor + SX, Methoxyfenozide + SX, Methyl bromide + SX, Metofluthrin + SX, Metolcarb + SX, Methoxadiazone + SX, Mevinphos + SX, Milbemectin + SX, Milbemycin oxime + SX, Mivorilaner + SX, Modoflaner + SX, Momfluorothrin + SX, Monocrotophos + SX, Moxidectin + SX, Naled + SX, Nicofluprole + SX, Nicotine + SX, Nicotine sulfate + SX, Nitenpyram + SX,Novaluron + SX, Noviflumuron + SX, Oil of the seeds of Chenopodium anthelminticum + SX, Omethoate + SX, Oxamyl + SX, Oxazosulfyl + SX, Oxidemeton-methyl + SX, Parathion + SX, Parathion-methyl + SX, Permethrin + SX, Phenothrin + SX, Phenthoate + SX, Phorate + SX, Phosalone + SX, Phosmet + SX, Phosphamidone + SX, Phosphine + SX, Phoxim + SX, Pioxaniliprole + SX, Piperflanilide + SX, Pirimicarb + SX, Pirimiphos-methyl + SX, Prallethrin + SX, Profenofos + SX, Profluthrin + SX, Propargite + SX, Propetamphos + SX, Propoxur + SX, Polypropylene glycol alginate + SX, Prothiofos + SX, Pyflubumide + SX, Pymetrozine + SX, Pyraclofos + SX, Pyrethrins + SX, Pyridaben + SX, Pyridalyl + SX,Pyridafenthion + SX, Pyrifluquinazone + SX, Pyrimidifen + SX, Pyriminostrobin + SX, Pyriprole + SX, Pyriproxyfen + SX, Quinalphos + SX, Resmethrin + SX, Rotenone + SX, Ryanodine + SX, Sarolaner + SX, Selamectin + SX, Sigma-cypermethrin + SX, Silafluofen + SX, Sodium borate + SX, Sodium metaborate metaborate) + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfiflumin + SX, sulfuramide + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX,Tefluthrin + SX, Temephos + SX, Terbufos + SX, Terpene constituents of the extract of chenopodium ambrosioides near ambrosioides + SX, Tetrachlorantraniliprole + SX, Tetrachlorvinphos + SX, Tetradifon + SX, Tetramethrin + SX, Tetramethylfluthrin + SX, Tetraniliprole + SX, Theta-cypermethrin + SX, Thiacloprid + SX, Thiamethoxam + SX, Thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodium + SX, tiapyrachlor + SX, tigolaner + SX, tiorantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, Trichlorfon + SX, Trifluenfuronate + SX,Triflumezopyrim + SX, Triflumuron + SX, Trimethacarb + SX, Tyclopyrazoflor + SX, Umifoxolaner + SX, Vadescana + SX, Vamidothion + SX, Wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, Xylylcarb + SX, Zeta-cypermethrin + SX, Zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, Bacillus thuringiensis-derived Cry1Ab protein + SX,Cry1Ac protein from Bacillus thuringiensis + SX, Cry1Fa protein from Bacillus thuringiensis + SX, Cry1A.105 protein from Bacillus thuringiensis + SX, Cry2Ab protein from Bacillus thuringiensis + SX, Vip3A protein from Bacillus thuringiensis + SX, mCry3A protein from Bacillus thuringiensis + SX, Cry3Ab protein from Bacillus thuringiensis SX, Bacillus thuringiensis Cry3Ab protein + SX, Bacillus thuringiensis Cry3Bb protein + SX, Bacillus thuringiensis Cry34Ab1 / Cry35Ab1 protein + SX, Adoxophyes orana GV (granulovirus) strain BV-0001 + SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus) + SX,Autographa californica MNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cytoplasmic polyhedron virus + SX, Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003 + SX, Helicoverpa zea NPV) + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX, Orgyia pseudotsugata NPV + SX, Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua MNPV + SX,Spodoptera littoralis MNPV + SX, Spinach snail (Spodoptera litura NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain BD#32 + SX CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX,Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX,Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX,Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,

[0055] Combinations of the main component from group (b) above with the compounds of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, Benzovindiflupyr + SX, Binapacryl + SX, Biphenyl + SX, Bitertanol + SX, Bixafen + SX, Blastoicidin-S + SX, Bordeaux mixture + SX, Boscalid + SX, Bromothalonil + SX, Bromuconazole + SX, Bupirimate + SX, Captafol + SX, Captan + SX, Carbendazim + SX, Carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX, chloroinconazide + SX, chloroneb + ​​SX,Chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, basic copper chloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, diclobentiazox + SX, Diclofluanid + SX, Diclocymet + SX, Diclomezine + SX, Dichloran + SX, Dietofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + SX, Dimethirimol + SX, Dimethomorph + SX, Dimoxystrobin + SX, Diniconazole + SX, Diniconazole-M + SX, Dinocap + SX, Dipotassium hydrogen phosphite + SX, dipymetitrone + SX, dithianon + SX,Dodecylbenzenesulfonic acid bisethylenediamine copper(II) complex salt + SX, Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epoxiconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Garlic extract (Allium sativum) + SX, Extract of the cotyledons of lupine plantlets ("BLAD") + SX, Horsetail extract (Equisetum arvense) + SX, Tea tree extract (extract of Melaleuca alternifolia) + SX, Japanese knotweed extract (extract of Reynoutria sachalinensis) + SX, Nasturtium extract (extract of Tropaeolum majus) + SX, Famoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Feneptamidoquin + SX, Fenfuram + SX, Fenhexamide + SX, Fenopyramid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamide + SX,Fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, fentin acetate + SX, fentin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, Fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetyl-aluminium + SX,Fuberidazole + SX, furalaxyl + SX, furametpyr + SX, galquin + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX, Iprovalicarb + SX, Isofetamide + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isothianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Leaves and bark of Quercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamide + SX, Maneb + ​​SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX,Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metarylpicoxamide + SX, Metconazole + SX, Methasulfocarb + SX, Methylam + SX, Metominostrobin + SX, Metrafenone + SX, Methyltetraprole + SX, Myclobutanil + SX, Naftifine + SX, Nuarimol + SX, Octylinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX, Oxathiapiprolin + SX, Oxine-copper + SX, Oxolinic acid + SX, Oxpoconazole + SX, Oxpoconazole fumarate + SX, Oxcarboxin + SX, Oxytetracycline + SX, Pefurazoate + SX, Penconazole + SX, Pencycuron + SX, Penflufen + SX, Penthiopyrad + SX, Phenamacril + SX, Phosphorous acid + SX, Phthalide + SX, Picarbutrazox + SX, Picoxystrobin + SX, Piperalin + SX,Polyoxins + SX, Potassium hydrogencarbonate + SX, Potassium dihydrogenphosphite + SX, Probenazole + SX, Prochloraz + SX, Procymidone + SX, Propamidine + SX, Propamocarb + SX, Propiconazole + SX, Propineb + ​​SX, Proquinazid + SX, Prothiocarb + SX, Prothioconazole + SX, Pydiflumetofen + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyrifenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, Quinofumelin + SX, Quinoxyfen + SX, Quintozene + SX,Quinoa saponins (Saponins of Chenopodium quinoa) + SX, Seboctylamine + SX, Sedaxane + SX, Silthiofam + SX, Simeconazole + SX, Sodium hydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, tifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, Tridemorph + SX, Trifloxystrobin + SX, Triflumizole + SX, Triforine + SX,トリチコナゾール(triticonazole) + SX, バリダマイシン(validamycin) + SX, バリフェナレート(valifenalate) + SX, ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX,N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX,2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX,3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX,4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX,1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, methyl (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]prop-2-enoate + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX,Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX,Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX,Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX,Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX,Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,

[0056] Combinations of the main component from group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, Cyclanilide + SX,Daminozide + SX, Decan-1-ol + SX, Dichlorprop + SX, Dikegulac + SX, Dimethipin + SX, Diquat + SX, Ethephon + SX, Ethychlozate + SX, Flumetralin + SX, Flurprimidol + SX, Forchlorfenuron + SX, Formononetin + SX, Gibberellin A + SX, Gibberellin A3 + SX, Inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat-chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione-calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintofen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, Thidiazuron + SX, Tripenthenol + SX, Tribufos + SX, Trinexapac-ethyl + SX,Uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate methyl + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX。,

[0057] Combinations of the above group (d) components with the compounds of the present invention: allidochlor + SX, benoxacor + SX, cloquintocet + SX, cloquintocet-mexyl + SX, cyometrinil + SX, cyprosulfamide + SX, dichlormid + SX, dicyclonone + SX, dimepiperate + SX, disulfoton + SX, dymron + SX, fenchlorazole + SX, fenchlorazole-ethyl + SX, fenchlorrim + SX, Flurazole + SX, Furilazole + SX, Fluxofenim + SX, Hexim + SX, Isoxadifen + SX, Isoxadifen-ethyl + SX, Jiecaowan + SX, Jiecaoxi + SX, Mecoprop + SX, Mefenpyr + SX, Mefenpyr-ethyl + SX, Mefenpyr-diethyl + SX, Mephenate + SX, Metocamifen + SX, Oxabetrinil + SX, 1,8-Naphthalic Anhydride + SX, octane-1,8-diamine + SX, AD-67 (4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5] decane) + SX, CL-304415 (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) + SX, CSB (1-bromo-4-[(chloromethyl)sulfonyl]benzene) + SX, DKA-24 (2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-(2-propenyl)acetamide) + SX, MG191 (2-(dichloromethyl)-2-methyl-1,3-dioxolane) + SX, MG-838 (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) + SX, PPG-1292 (2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide) + SX, R-28725 (3-(dichloroacetyl)-2,2-dimethyl-1,3-oxazolidine) + SX, R-29148 (3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine) + SX, TI-35 (1-(dichloroacetyl)azepane) + SX。.

[0058] Combinations of the main component from group (e) above with the compound of the present invention: 1-dodecyl-1H-imidazole + SX, N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboximide + SX, bucarpolate + SX, N,N-dibutyl-4-chlorobenzenesulfonamide + SX, dietholate + SX, diethylmaleate + SX, Jiajizengxiaolin + SX, octachlorodipropyl ether + SX, perbutin + SX, piperonyl butoxide + SX, piperonyl cyclonene + SX, piprotal + SX, propyl isome + SX, safroxan + SX, sesamex + SX, sesamolin + SX, sulfoxide + SX, Verbutin + SX, DMC (1,1-bis(4-chlorophenyl)ethanol) + SX, FDMC (1,1-bis(4-chlorophenyl)-2,2,2-trifluoroethanol) + SX, ETN (1,2-epoxy-1,2,3,4-tetrahydronaphthalene) + SX, ETP (1,1,1-trichloro-2,3-expoxypropane) + SX, PSCP (phenylsaligenin cyclic phosphate) + SX, TBPT (S,S,S-tributyl phosphorotrithioate) + SX,TPP (triphenyl phosphate) + SX。,

[0059] Combinations of the main component from group (f) above with the compound of the present invention: 2,3,6-TBA (2,3,6-trichlorobenzoic acid) + SX,2,3,6-TBA-dimethylammonium + SX,2,3,6-TBA-lithium salt + SX,2,3,6-TBA-potassium salt + SX,2,3,6-TBA-sodium salt + SX,2,4-D + SX,2,4-D choline salt + SX,2,4-D biproamine + SX,2,4-D doboxyl + SX,2,4-D 2-ethylhexyl (2,4-D-2-ethylhexyl) + SX, 2,4-D 3-butoxypropyl (2,4-D-3-butoxypropyl) + SX, 2,4-D ammonium (2,4-D-ammonium) + SX, 2,4-D butotyl (2,4-D-butotyl) + SX, 2,4-D butyl (2,4-D-butyl) + SX, 2,4-D diethylammonium (2,4-D-diethylammonium) + SX, 2,4-D dimethylammonium (2,4-D-dimethylammonium) + SX, 2,4-D diolamine (2,4-D-diolamine) + SX, 2,4-D dodecylammonium (2,4-D-dodecylammonium) + SX, 2,4-D ethyl (2,4-D-ethyl) + SX, 2,4-D-heptylammonium + SX, 2,4-D-isobutyl + SX, 2,4-D-isooctyl + SX, 2,4-D-isopropyl + SX, 2,4-D-isopropylammonium + SX, 2,4-D-lithium salt + SX, 2,4-D-meptyl + SX,2,4-D-methyl + SX, 2,4-D-octyl + SX, 2,4-D-pentyl + SX, 2,4-D-propyl + SX, 2,4-D-sodium + SX, 2,4-D-tefuryl + SX, 2,4-D-tetradecylammonium + SX, 2,4-D-triethylammonium + SX, 2,4-D-tris(2-hydroxypropyl)ammonium + SX, 2,4-D-trolamine + SX, 2,4-DB+SX, 2,4-DB choline salt + SX, 2,4-DB biproamine + SX, 2,4-DB butyl + SX, 2,4-DB dimethylammonium + SX, 2,4-DB isooctyl + SX, 2,4-DB potassium salt + SX, 2,4-DB sodium salt + SX, acetochlor + SX, acifluorfen + SX, acifluorfen-sodium + SX, acroniphen + SX, ACN (2-amino-3-chloronaphthalene-1,4-dione) + SX, alachlor + SX, alloxydim + SX, ametryn + SX, amicarbazone + SX, amidosulfuron + SX, aminocyclopyrachlor + SX,Aminocyclopyrachlor-methyl + SX, Aminocyclopyrachlor-potassium salt + SX, Aminopyralid + SX, Aminopyralid choline salt + SX, Aminopyralid-potassium salt + SX, Aminopyralid-tripromine + SX, Amiprophos-methyl + SX, Amitrol + SX, Anilofos + SX, Asulam + SX, Atrazine + SX, Azafenidin + SX, Azimsulfuron + SX, Beflubutamid + SX, Benazolin-ethyl + SX, Bencarbazone + SX, Benfluralin + SX, Benfuresate + SX, Benquitrione + SX, Bensulfuron + SX, Bensulfuron-methyl + SX, Bensulide + SX, Bentazon + SX, Benthiocarb + SX, Benzfendizone + SX, Benzobicyclon + SX, Benzofenap + SX, Benzthiazuron + SX, Bialafos + SX, Bicyclopyrone + SX, Bifenox + SX, Bipyrazone + SX, Bispyribac + SX,Bispyribac-sodium + SX, Bixlozone + SX, Bromacil + SX, Bromobutide + SX, Bromofenoxim + SX, Bromoxynil + SX, Bromoxynil-octanoate + SX, Butachlor + SX, Butafenacil + SX, Butamifos + SX, Butroxydim + SX, Butyrate + SX, Cafenstrole + SX, Carbetamide + SX, Carfentrazone + SX, Carfentrazone-ethyl + SX, Chlomethoxyfen + SX, Chloramben + SX, Chloridazon + SX, Chlorimuron + SX, Chlorimuron-ethyl + SX, Chlorbromuron + SX, Chlortoluron + SX, Chlorxuron + SX, Chlorpropham + SX, Chlorsulfuron + SX, Chlorthal-dimethyl + SX, Chlorthiamid + SX, Cinflubrolin + SX, Cinidone + SX, Cinidone-ethyl + SX, Cinmethylin + SX, Cinosulfuron + SX, Clethodim + SX, Clodinafop + SX,Clodinafop-propargyl + SX, Clomazone + SX, Clomeprop + SX, Clopyralid + SX, Clopyralid choline salt + SX, Clopyralid-methyl + SX, Clopyralid-olamine + SX, Clopyralid-potassium + SX, Clopyralid-tris(2-hydroxypropyl)ammonium + SX, Cloransulam + SX, Cloransulam-methyl + SX, Cumyluron + SX, Cyanazine + SX, Cycloate + SX, Cyclopyranil + SX, Cyclopyrimorate + SX, Cyclosulfamuron + SX, Cycloxydim + SX, Cyhalofop + SX, Cyhalofop-butyl + SX, Cypyrafluone + SX, Dalapon + SX, Dazomet + SX, Desmedipham + SX, Desmetryn + SX, Dialate + SX, Dicamba + SX, Dicamba choline salt + SX, Dicamba-biproamine + SX, Dicanba trolamine salt + SX, Dicanba diglycolamine salt + SX,Dicamba-dimethylammonium + SX, Dicamba-diolamine + SX, Dicamba-isopropylammonium + SX, Dicamba-methyl + SX, Dicamba-olamine + SX, Dicamba-potassium + SX, Dicamba-sodium + SX, Diclobenil + SX, Dichlorprop choline salt + SX, Dichlorprop-biproamine + SX, Dichlorprop-2-ethylhexyl + SX, Dichlorprop-butotyl + SX, Dichlorprop-dimethylammonium + SX, Dichlorprop-ethylammonium + SX, Dichlorprop-isoctyl + SX, Dichlorprop-methyl + SX, Dichlorprop-P + SX, Dichlorprop-P choline salt + SX, Dichlorprop-P-biproamine + SX, Dichlorprop-P-etexyl + SX, Dichlorprop-P-dimethylammonium + SX, Dichlorprop-potassium salt + SX, Dichlorprop-sodium salt + SX, Diclofop + SX,Diclofop-methyl + SX, Diclosulam + SX, Difenoxuron + SX, Difenzoquat + SX, Difenzoquat metilsulfate + SX, Diflufenican + SX, Diflufenzopyr + SX, Diflufenzopyr sodium + SX, Dimefuron + SX, Dimepiperate + SX, Dimesulfazet + SX, Dimethachlor + SX, Dimethametryn + SX, Dimethenamid + SX, dimethenamid-P + SX, dinitramine + SX, dinoseb + SX, dinoterb + SX, dioxopyritrione + SX, diphenamid + SX, diquat-dibromide + SX, DSMA (disodium methylarsonate) + SX, dithiopyr + SX, diuron + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, epiriphenacil + SX, esprocarb + SX, ethalfluralin + SX, ethametsulfuron + SX, ethametsulfuron-methyl + SX, ethidimuron + SX, ethofumesate + SX, ethoxyfen-ethyl + SX,Ethoxysulfuron + SX, etobenzanid + SX, fenoxaprop + SX, fenoxaprop-ethyl + SX, fenoxaprop-P + SX, fenoxaprop-P-ethyl + SX, fenoxasulfone + SX, fenpyrazone + SX, fenquinotrione + SX, fentrazamide + SX, fenuron + SX, feproxydim + SX, flamprop-M + SX, flazasulfuron + SX, florasulam + SX, florpyrauxifen + SX, florpyrauxifen-benzyl + SX, fluazifop + SX, fluazifop-butyl + SX, fluazifop-P + SX, fluazifop-P-butyl + SX, fluazolate + SX, flucarbazone + SX, flucarbazone-sodium + SX, flucetosulfuron + SX, fluchloraminopyr + SX, fluchloraminopyr-tefuryl + SX, flufenacet + SX, flufenoximacil + SX, flufenpyr + SX, flufenpyr-ethyl + SX, flumetsulam + SX,Flumetslam + SX, Flumiclorac + SX, Flumiclorac-pentyl + SX, Flumioxazin + SX, Fluometuron + SX, Fluoroglycofen-ethyl + SX, Flupoxam + SX, Flupropanate + SX, Flupyrsulfuron + SX, Flupyrsulfuron-methyl-sodium + SX, Flurenol + SX, Fluridone + SX, Flurochloridone + SX, Fluroxypyr + SX, Fluroxypyr-butometyl + SX, Fluroxypyr-meptyl + SX, Flurtamone + SX, Flusulfinam + SX, Fluthiacet + SX, Fluthiacet-methyl + SX, Fomesafen + SX, Fomesafen-sodium + SX, Foramsulfuron + SX, Fosamine + SX, Glufosinate + SX, Glufosinate-ammonium + SX, Glufosinate-P + SX, Glufosinate-P-ammonium salt + SX, Glufosinate-P-sodium salt + SX, Glyphosate + SX, Glyphosate choline salt + SX,Glyphosate-isopropylammonium + SX, Glyphosate-biproamine + SX, Glyphosate-ammonium salt + SX, Glyphosate-diammonium salt + SX, Glyphosate-potassium salt + SX, Glyphosate-sodium salt + SX, Glyphosate-trimesium + SX, Halauxifen + SX, Halauxifen-benzyl + SX, Halauxifen-methyl + SX, Halosafen + SX, Halosulfuron + SX, Halosulfuron-methyl + SX, Haloxyfop + SX, Haloxyfop-etotyl + SX, Haloxyfop-methyl + SX, Haloxyfop-P + SX, Haloxyfop-P-etotyl + SX, Haloxyfop-P-methyl + SX, Hexazinone + SX, Icafolin + SX, Icafolin-methyl + SX, Imazametabenz + SX, Imazametabenz-methyl + SX, Imazamox + SX, Imazamox-ammonium salt + SX, imazamox-sodium + SX, imazapic + SX,imazapic-ammonium + SX, imazapyr + SX, imazapyr-ammonium + SX, imazapyr-isopropylammonium + SX, imazaquin + SX, imazaquin-ammonium + SX, imazethapyr + SX, imazethapyr-ammonium + SX, imazosulfuron + SX, indanofan + SX, indaziflam + SX, indolauxipyr + SX, indolauxipyr-cyanomethyl + SX, iodosulfuron + SX, Iodosulfuron-methyl-sodium + SX, Iofensulfuron + SX, Iofensulfuron-sodium + SX, Ioxynil + SX, Ioxynil-octanoate + SX, Ipfencarbazone + SX, Iptriazopyrid + SX, Isoproturon + SX, Isouron + SX, Isoxaben + SX, Isoxachlortole + SX, Isoxaflutole + SX, Lactofen + SX, Lenacil + SX, Linuron + SX, maleic hydrazide + SX, MCPA choline salt + SX,MCPA-biproamine + SX, MCPA-etexyl + SX, MCPA-butotyl + SX, MCPA-butyl + SX, MCPA-dimethylammonium + SX, MCPA-diolamine + SX, MCPA-ethyl + SX, MCPA-isobutyl + SX, MCPA-isoctyl + SX, MCPA-isopropyl + SX, MCPA-methyl + SX, MCPA-olamine + SX, MCPA-sodium + SX, MCPA-trolamine + SX, MCPB (4-(4-chloro-2-methylphenoxy)butanoic acid) + SX, MCPB choline salt + SX, MCPB-biproamine + SX, MCPB-ethyl + SX, MCPB-methyl + SX, MCPB-sodium + SX, mecoprop choline salt + SX, mecoprop-biproamine + SX, mecoprop-2-ethylhexyl + SX, mecoprop-dimethylammonium + SX, mecoprop-diolamine + SX, mecoprop-ethadyl + SX, Mecoprop-isoctyl + SX, Mecoprop-methyl + SX,Mecoprop-potassium salt + SX, Mecoprop-sodium salt + SX, Mecoprop-trolamine salt + SX, Mecoprop-P + SX, Mecoprop-P choline salt + SX, Mecoprop-P 2-ethylhexyl + SX, Mecoprop-P-dimethylammonium + SX, Mecoprop-P-isobutyl + SX, Mecoprop-P-potassium salt + SX, Mefenacet + SX, Mesosulfuron + SX, Mesosulfuron-methyl + SX, mesotrione + SX, metam + SX, metamifop + SX, metamitron + SX, metazachlor + SX, metazosulfuron + SX, metabenzthiazuron + SX, methiozolin + SX, methyldymron + SX, metobromuron + SX, metolachlor + SX, metoxuron + SX, metosulam + SX, metproxybicyclone + SX, metribuzin + SX, Methosulfuron + SX, Methosulfuron-methyl + SX, Molinate + SX, Monolinuron + SX,Naproanilide + SX, Napropamide + SX, Napropamide-M + SX, Naptalam + SX, Neburon + SX, Nicosulfuron + SX, Norflurazon + SX, Oleic acid + SX, Orbencarb + SX, Orthosulfamuron + SX, Oryzalin + SX, Oxadiargyl + SX, Oxadiazon + SX, Oxasulfuron + SX, Oxaziclomefone + SX, Oxyfluorfen + SX, paraquat + SX, paraquat-dichloride + SX, pebulate + SX, pelargonic acid + SX, pendimethalin + SX, penoxsulam + SX, pentanochlor + SX, pentoxazone + SX, petoxamid + SX, phenisopham + SX, phenmedipham + SX, picloram, picolinafen + SX, picolinafen + SX, pinoxaden + SX, piperophos + SX, Pretilachlor + SX, Primisulfuron + SX, Primisulfuron-methyl + SX, Prodiamine + SX,Profluazol + SX, Propoxydim + SX, Prometon + SX, Prometrin + SX, Propachlor + SX, Propanil + SX, Propaquizafop + SX, Propazine + SX, Profam + SX, Propisochlor + SX, Propoxycarbazone + SX, Propoxycarbazone sodium + SX, Propyrisulfuron + SX, Propyzamide + SX, Prosulfocarb + SX, Prosulfuron + SX, Pyraclonil + SX, Pyraquinate + SX, pyrasulfotole + SX, pyrazolynate + SX, pyrazosulfuron + SX, pyrazosulfuron-ethyl + SX, pyrazoxyfen + SX, pyribenzoxim + SX, pyributicarb + SX, pyridafol + SX, pyridate + SX, pyriflubenzoxim + SX, pyriftalid + SX, pyriminobac + SX, pyriminobac-methyl + SX, pyrimisulfan + SX, pyrithiobac + SX, pyrithiobac-sodium + SX,Pyroxasulfone + SX, Pyroxsulam + SX, Quinclorac + SX, Quinmerac + SX, Quizalofop + SX, Quizalofop-ethyl + SX, Quizalofop-tefuryl + SX, Quizalofop-P + SX, Quizalofop-P-ethyl + SX, Quizalofop-P-tefuryl + SX, Rimisoxafen + SX, Rimsulfuron + SX, Saflufenacil + SX, Setoxydim + SX, EPTC (S-ethyl N,N-dipropylcarbamothioate) + SX, Siduron + SX, Simazine + SX, Simetryn + SX, S-metolachlor + SX, MSMA (sodium hydrogen methylarsonate) + SX, Sulcotrione + SX, Sulfentrazone + SX, Sulfometuron + SX, Sulfometuron-methyl + SX, Sulfosulfuron + SX, Swep + SX, TCA (2,2,2-trichloroacetic acid) + SX, TCA-ammonium + SX, TCA calcium + SX, TCA ethadyl + SX, TCA magnesium + SX, TCA sodium + SX, tebutam + SX,Tebuthiuron + SX, Tefuryltrione + SX, Tembotrione + SX, Tepraloxydim + SX, Terbacil + SX, Terbumeton + SX, Terbuthylazine + SX, Terbutryn + SX, Tetflupyrolimet + SX, Thaxtomin A + SX, Thenylchlor + SX, Thiazopyr + SX, Thiidiazimin + SX, Thiencarbazone + SX, Thiencarbazone-methyl + SX, thifensulfuron + SX, thifensulfuron-methyl + SX, tiafenacil + SX, tiocarbazil + SX, tolpyralate + SX, topramezone + SX, tralkoxydim + SX, triafamone + SX, tri-allate + SX, triasulfuron + SX, triaziflam + SX, tribenuron + SX, tribenuron-methyl + SX, triclopyr + SX, triclopyr-butotyl + SX, Triclopyr-ethyl + SX, Triclopyr-triethylammonium + SX, Tridiphane + SX, Trietazine + SX,Trifloxysulfuron + SX, Trifloxysulfuron-sodium + SX, Trifludimoxazin + SX, Trifluralin + SX, Triflusulfuron + SX, Triflusulfuron-methyl + SX, Tripyrasulfone + SX, Tritosulfuron + SX, Vernolate + SX, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione + SX, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-3-(methylthio)-4-(trifluoromethyl)benzamide + SX, 2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methanesulfonyl)-4-(trifluoromethyl)benzamide + SX, 1-{2-chloro-6-[(5-chloropyrimidin-2-yl)oxy]phenyl}-4,4,4-trifluorobutan-1-one (2052297-97-7) + SX. ,

[0060] The ratio of the compound of the present invention to the component of this invention is not particularly limited, but examples of weight ratios (compound of the present invention:component of this invention) include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0061] The following are some examples of pests and diseases that can be controlled by the compounds of the present invention, but they are not limited to these. Weeds of the Urticaceae family: Urtica urens Weeds of the Polygonaceae family: Polygonum convolvulus, Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Polygonum longisetum, Polygonum aviculare, Polygonum arenastrum, Polygonum cuspidatum, Rumex japonicus, Rumex crispus, Rumex obtusifolius, Rumex acetosa Weeds of the Portulacaceae family: Portulaca oleracea Weeds of the Caryophyllaceae family: Stellaria media, Stellaria aquatica, Cerastium holosteoides, Cerastium glomeratum, Spergula arvensis, Silene gallica Weeds of the Molluginaceae family: Mollugo verticillata Weeds of the Chenopodiaceae family: Chenopodium album, Chenopodium ambrosioides, Bassia scoparia, Salsola kali, Atriplex spp.

[0062] Amaranthaceae weeds: Amaranthus retroflexus, Amaranthus viridis, Amaranthus lividus, Amaranthus spinosus, Amaranthus hybridus, Amaranthus palmeri, Amaranthus patulus, Water hemp (Amaranthus tuberculatus = Amaranthus rudis = Amaranthus tamariscinus), American amaranth (Amaranthus blitoides), dwarf amaranth (Amaranthus deflexus), Amaranthus quitensis, Alternanthera philoxeroides, and Alternanthera Papaveraceae weeds: *Papaver sessilis*, *Alternanthera tenella* (Sanguinaria) Papaveraceae weeds: *Papaver rhoeas*, *Papaver dubium*, *Argemone mexicana* Brassicaceae weeds: *Raphanus raphanistrum*, *Raphanus sativus*, *Sinapis arvensis*, *Capsella bursa-pastoris*, *Brassica juncea*, *Brassica napus*, *Descurainia pinnata*, *Rorippa islandica*, *Rorippa sylvestris*, *Thlaspi arvense*, *Myagrum* Rugosum, Lepidium virginicum, Coronopus didymusCapparaceae weed: Cleome affinis

[0063] Leguminous weeds (Fabaceae): Aeschynomene indica, Zigzag joint vetch (Aeschynomene rudis), American horned vetch (Sesbania exaltata), Cassia obtusifolia, Cassia occidentalis, Desmodium tortuosum, Desmodium adscendens, Desmodium illinoense, White clover (Trifolium repens), Pueraria lobata, Vicia angustifolia, Indigofera hirsuta, Indigofera truxillensis, Wild cowpea (Vigna sinensis) Oxalidaceae weeds: Oxalis Oxalis corniculata, Oxalis stricta, Oxalis oxyptera Geraniaceae weeds: Geranium carolinense, Erodium cicutarium Euphorbiaceae weeds: Euphorbia helioscopia, Euphorbia maculata, Euphorbia humistrata, Euphorbia esula, Euphorbia heterophylla, Euphorbia brasiliensis, Acalypha australis, Croton glandulosus, Croton lobatus, Phyllanthus corcovadensis), castor bean (Ricinus communis)

[0064] Malvaceae weeds: Abutilon theophrasti, Sida rhombifolia, Sida cordifolia, Sida spinosa, Sida glaziovii, Sida santaremnensis, Hibiscus trionum, Anoda cristata, Malvastrum coromandelianum Onagraceae weeds: Ludwigia epilobioides, Ludwigia octovalvis, Ludwigia decurrens, Oenothera biennis, Oenothera laciniata Weeds of the Sterculiaceae family: Waltheria indica Weeds of the Violaceae family: Viola arvensis, Viola tricolor Weeds of the Cucurbitaceae family: Sicyos angulatus, Echinocystis lobata, Momordica charantia Weeds of the Lythraceae family: Ammannia multiflora, Ammannia auriculata, Ammannia coccinea, Lythrum salicaria, Rotala indica Weeds of the Elatinaceae family: Elatine Triandra, California Waterwort (Elatine californica)

[0065] Apiaceae weeds: Oenanthe javanica, Daucus carota, Conium maculatum Araliaceae weeds: Hydrocotyle sibthorpioides, Hydrocotyle ranunculoides Ceratophyllaceae weeds: Ceratophyllum demersum Cabombaceae weeds: Cabomba caroliniana Haloragaceae weeds: Myriophyllum aquaticum, Myriophyllum verticillatum, Watermillfoil species (Myriophyllum spicatum, Myriophyllum heterophyllum, etc.) Sapindaceae weeds: Cardiospermum halicacabum Primulaceae weeds: Anagallis arvensis Asclepiadaceae weeds: Asclepias syriaca, Ampelamus albidus Rubiaceae weeds: Galium aparine, Galium spurium var. echinospermon, Spermacoce latifolia, Richardia brasiliensis, Borreria alata

[0066] Convolvulaceae weeds: Morning glory (Ipomoea nil), American morning glory (Ipomoea hederacea), round-leaved morning glory (Ipomoea purpurea), round-leaved American morning glory (Ipomoea hederacea var. integriuscula), bean morning glory (Ipomoea lacunosa), star morning glory (Ipomoea triloba), field morning glory (Ipomoea acuminata), ivy vine (Ipomoea hederifolia), cypress vine (Ipomoea coccinea), quamoclit, Ipomoea grandifolia, Ipomoea aristolochiaefolia, maple-leaf morning glory (Ipomoea cairica), European morning glory (Convolvulus) Weeds of the Boraginaceae family: Forget-me-not (Myosotis arvensis), Convolvulus (Calystegia hederacea), Convolvulus (Calystegia japonica), Ivy-leaf Convolvulus (Merremia hederacea), Hairy wood rose (Merremia aegyptia), Roadside wood rose (Merremia cissoides), Ipomoea purpurea (Jacquemontia tamnifolia) Weeds of the Lamiaceae family: Lamium purpureum, Lamium amplexicaule, Leonotis nepetaefolia, Scented bitter grass (Hyptis suaveolens), Hyptis lophanta, Leonurus *Sibiricus*, *Stachys arvensis*

[0067] Solanaceae weeds: Datura stramonium, Solanum nigrum, Solanum americanum, Solanum ptycanthum, Solanum sarrachoides, Solanum rostratum, Solanum aculeatissimum, Solanum sisymbriifolium, Solanum carolinense, Physalis angulata, Physalis subglabrata, Nicandra physalodes Scrophulariaceae weeds: Veronica hederaefolia, Veronica Weeds of the Plantaginaceae family: Plantago asiatica, Plantago lanceolata, Plantago major, Water chickweed (Callitriche palustris)

[0068] Asteraceae weeds: Cocklebur (Xanthium pensylvanicum), Giant Cocklebur (Xanthium occidentale), Spiny Cocklebur (Xanthium italicum), Wild Sunflower (Helianthus annuus), Chamomile (Matricaria chamomilla), Dog Chamomile (Matricaria perforata), Corn Marigold (Chrysanthemum segetum), White Daisy (Matricaria matricarioides), Mugwort (Artemisia princeps), European Mugwort (Artemisia vulgaris), Chinese Mugwort (Artemisia verlotorum), Tall Goldenrod (Solidago altissima), Common Dandelion (Taraxacum officinale), Garcinia ciliata, Small-leaved Daisy (Galinsoga parviflora), Senecio (Vulgaris), Senecio brasiliensis, Senecio grisebachii, Conyza bonariensis, Conyza smatrensis, Conyza canadensis, Ambrosia artemisiifolia, Ambrosia trifida, Bidens tripartita, Bidens pilosa, Bidens frondosa, Bidens subalternans, Cirsium arvense, Cirsium vulgare, Silybum marianum, Carduus nutans, Lactuca (Serriola), Sonchus oleraceus, Prickly sow thistle (Sonchus asper), Beach creeping oxeye (Wedelia)glauca), perforated blackfoot (Melampodium perfoliatum), pale red sedge (Emilia sonchifolia), salt-leaved daisy (Tagetes minuta), paracles (Blainvillea latifolia), kotobuki daisy (Tridax procumbens), yerba porosa (Porophyllum ruderale), Paraguay star bark (Acanthospermum australe), bristle star bark (Acanthospermum hispidum), balloon vine (Cardiospermum halicacabum), cuckoo thistle (Ageratum conyzoides), common bone set (Eupatorium perfoliatum), dando ragwort (Erechtites hieracifolia), American everlasting (Gamochaeta spicata), white-leaved cudweed (Gnaphalium spicatum), Jaegeria hitora hirta, Parthenium hysterophorus, Siegesbeckia orientalis, Soliva sessilis, Eclipta prostrata, Eclipta alba, Centipeda minima

[0069] Alismataceae weeds: Sagittaria pygmaea, Sagittaria trifolia, Sagittaria sagittifolia, Sagittaria montevidensis, Sagittaria aginashi, Alisma canaliculatum, Alisma plantago-aquatica Limnocharitaceae weeds: Limnocharis flava Hydrocharitaceae weeds: Limnobium spongia, Hydrollilla verticillata, Najas guadalupensis Araceae weeds: Pistia stratiotes Lemnaceae weeds: Lemna aoukikusa (Lemna paucicostata, Lemna aequinoctialis), Spirodela polyrhiza, Wolffia spp.) Potamogetonaceae weeds: Potamogeton distinctus, pondweeds (Potamogeton crispus, Potamogeton illinoensis, Stuckenia pectinata, etc.) Liliaceae weeds: Wild onion (Allium canadense), wild garlic (Allium vineale), wild onion (Allium macrostemon) Pontederiaceae weeds: Water hyacinth (Eichhornia crassipes), American dwarf Keisak)

[0070] Grass weeds (Poaceae): Barnyard grass (Echinochloa crus-galli), Echinochloa oryzicola, Echinochloa crus-galli var. formosensis, Late watergrass (Echinochloa oryzoides), Small barnyard grass (Echinochloa colona), Gulf cockspur (Echinochloa crus-pavonis), Foxtail grass (Setaria viridis), Autumn foxtail grass (Setaria faberi), Golden foxtail grass (Setaria glauca), American foxtail grass (Setaria geniculata), Digitaria ciliaris, Large crabgrass (Digitaria sanguinalis), Jamaican crabgrass (Digitaria horizontalis), Japanese pampas grass (Digitaria insularis), Eleusine indica, Annual bluegrass (Poa annual grass (Poa annua), large-leaved bluegrass (Poa trivialis), long-leaved grass (Poa pratensis), sparrow's gun (Alopecurus aequalis), black grass (Alopecurus myosuroides), wild oat (Avena fatua), halepense (Sorghum halepense), shattercane (Sorghum vulgare), sorghum repens, ryegrass (Agropyron repens), ryegrass (Lolium multiflorum), slender ryegrass (Lolium perenne), ryegrass (Lolium rigidum), dog ryegrass (Bromus catharticus), wild tea flea (Bromus sterilis), sparrow's tea flea (Bromus japonicus), black grass (Bromus secalinus), horse tea flea (Bromus tectorum), narrow-leaved ryegrass (Hordeum jubatum), goat's ryegrass (Aegilops) Phalaris arundinacea, Phalaris canariiminor), silky bentgrass (Apera spica-venti), large sedge (Panicum dichotomiflorum), Texas panicum (Panicum texanum), Guinea sedge (Panicum maximum), American sedge (Brachiaria platyphylla), ruziziensis (Brachiaria ruziziensis), Alexander grass (Brachiaria plantaginea), Suriname grass (Brachiaria decumbens), Palisade grass (Brachiaria brizantha), Columbia grass (Brachiaria humidicola), cenchrus echinatus, dwarf sedge (Cenchrus pauciflorus), narcolepsy (Eriochloa villosa), pennisetum setosum, African grass (Chloris gayana), large grass (Chloris virgata), large dwarf grass (Eragrostis pilosa), Ruby grass (Rhynchelytrum repens), Sea horn grass (Dactyloctenium aegyptium), Taiwan grass (Ischaemum rugosum), Isachne globosa, Wild rice (Oryza sativa), American barnyard grass (Paspalum notatum), Coastal sand barnyard grass (Paspalum maritimum), Yellow barnyard grass (Paspalum distichum), Chrysanthemum grass (Pennisetum clandestinum), Narrow-leaved barnyard grass (Pennisetum setosum), Horned barnyard grass (Rottboellia cochinchinensis), Dracaena chinensis, Giant barnyard grass (Leptochloa fascicularis), Thread barnyard grass (Leptochloa filiformis), Amazon sprung top (Leptochloa Panicoides), Ashikaki (Leersia japonica), Sayanukagusa (Leersia(Sayanuka), Leersia oryzoides, Glyceria leptorrhiza, Glyceria acutiflora, Glyceria maxima, Agrostis gigantea, Agrostis stolonifera, Cynodon dactylon, Dactylis glomerata, Eremochloa ophiuroides, Festuca arundinacea, Festuca rubra, Imperata cylindrica, Miscanthus sinensis, Panicum virgatum, Zoysia japonica

[0071] Cyperaceae weeds: Cyperus microiria, Cyperus iria, Cyperus compressus, Cyperus difformis, Cyperus flaccidus, Cyperus globosus, Cyperus nipponicus, Cyperus odoratus, Cyperus serotinus, Cyperus rotundus, Cyperus esculentus, Kyllinga gracillima, Kyllinga brevifolia, Fimbristylis miliacea, Fimbristylis Equisetaceae weeds: Equisetum arvense, Equisetum palustre Salviniaceae weeds: Salvinia natans; Azollaceae weeds: Azolla japonica, Azolla pinnataMarsileaceae weeds: Marsilea quadrifolia. Others: Filamentous algae (Pithophora, Cladophora), mosses, liverworts, hornworts, cyanobacteria, ferns, and suckers of perennial crops (pomes, stony fruits, berries, nuts, citrus fruits, hops, grapes, etc.).

[0072] The weeds mentioned above are not limited to intraspecies mutations. That is, they also include those with reduced sensitivity (or resistance) to specific herbicides. Reduced sensitivity may be due to mutations at the target site (site of action mutations) or to factors other than site of action mutations (non-site of action mutations). Site of action mutations include those in which amino acid substitutions occur in the target site protein due to mutations in the nucleic acid sequence portion (open reading frame) corresponding to the amino acid sequence of the protein, and those in which the target site protein is overexpressed due to mutations such as deletion of suppressor sequences in the promoter region, amplification of enhancer sequences, or increase in the copy number of the gene. Factors causing reduced sensitivity due to non-site of action mutations include increased metabolism, malabsorption, impaired translocation, and excretion. Examples of factors causing increased metabolism include increased activity of metabolic enzymes such as cytochrome P450 monooxygenase (CYP), aryl acylamidase (AAA), esterase, glutathione S transferase (GST), and cyanoalanine nitrilase. Extrusion from the system can be attributed to transport to vacuoles by ABC transporters. Examples of herbicide-resistant weeds include the following: Glyphosate resistance: Examples of reduced weed susceptibility due to site of action mutations include weeds with mutations in the EPSPS gene that cause one or more of the following amino acid substitutions: Thr102Ile, Pro106Ser, Pro106Ala, Pro106Leu, Pro106Thr. In particular, weeds possessing both Thr102Ile and Pro106Ser, and those possessing both Thr102Ile and Pro106Thr are noteworthy. Glyphosate-resistant weeds with these site of action mutations, such as goosegrass, ryegrass, ryegrass, ryegrass, and Bidens subalternans, are effectively controlled. Similarly, an example of glyphosate resistance involving the site of action is an increase in the copy number of the EPSPS gene (PNAS, 2018 115 (13) 3332-3337). This invention provides effective control over glyphosate-resistant varieties of Amaranthus philoxeroides, water hemp, and Kochia japonica, which have increased copy numbers of the EPSPS gene.Examples of reduced weed susceptibility due to non-point mutations include glyphosate-resistant varieties such as Erigeron annuus, Erigeron strumarium, and Erigeron philoxeroides, which involve the ABC transporter, and these can be effectively controlled by the present invention. Furthermore, as a non-point mutation, Echinochloa crus-galli, which has reduced susceptibility to glyphosate due to increased expression of aldoketo reductase, is known (Plant Physiology 181, 1519-1534), and this can also be effectively controlled by the present invention. ALS inhibitor herbicide resistance: Examples of reduced weed susceptibility due to point mutations include weeds with mutations in the ALS gene that cause one or more of the following amino acid substitutions. Ala122Thr, Ala122Val, Ala122Tyr, Pro197Ser, Pro197His, Pro197Thr, Pro197Arg, Pro197Leu, Pro197Gln, Pro197Ala, Pro197Ile, Ala205Val, Ala205Phe, Asp376Glu, Asp376Gln, Asp376Asn, Arg377His, Trp574Leu, Trp574Gly, Trp574Met, Ser653Thr, Ser653Asn, Ser635Ile, Gly654Glu, Gly645Asp. The present invention effectively controls ALS inhibitor-resistant Amaranthus philoxeroides, Amaranthus longifolius, Amaranthus serrata, water hemp, Kochia japonica, etc., which have these site mutations. Examples of reduced weed susceptibility due to non-point mutations include weeds that have become resistant to ALS inhibitors due to the involvement of CYP or GST, and these can be effectively controlled by the present invention. Examples of such weeds include barnyard grass with overexpression of CYP81A10 or CYP81A1v1, barnyard grass with overexpression of CYP81A12 or CYP81A21, and Japanese hawkweed with overexpression of GSTF1 or GSTU2. ACCase inhibitor resistance: Examples of reduced weed susceptibility due to point mutations include weeds with mutations in the ACCase gene that cause one or more of the following amino acid substitutions.Ile1781Ala, Ile1781Leu, Ile1781Val, Ile1781Thr, Leu1818Phe, Trp1999Cys, Trp1999Leu, Trp1999Ser, Ala2004Val, Trp2027Cys, Trp2027Leu, Ile2041Asn, Ile2041Asp, Ile2041Val, Ile2041Thr, Asp2078Gly, Asp2078Glu, Cys2088Arg, Cys2088Phe, Gly2096Ala, Gly2096Ser. The present invention effectively controls ACCase-resistant weeds having these site-of-action mutations. Similarly, an example of ACCase inhibitor resistance involving the site of action is increased expression of ACCase genes (Pest Manag. Sci. 2017 Nov;73(11):2227-2235). An example of reduced weed susceptibility due to non-site mutations is weeds that have become resistant to ACCase inhibitors due to the involvement of CYP or GST, and these can be effectively controlled by the present invention. Examples of such weeds include barnyard grass with overexpression of CYP81A10 or CYP81A1v1, barnyard grass with overexpression of CYP81A12, CYP81A21, or CYP709C69, and Japanese laurel with overexpression of GSTF1 or GSTU2. PPO inhibitor resistance: An example of reduced weed susceptibility due to site mutations is weeds with mutations in the PPO gene that cause one or more of the following amino acid substitutions. These mutations are known as or predicted to become resistance mutations to carfentrazone ethyl, homesaphene, or lactofen.Arg128Leu, Arg128Met, Arg128Gly, Arg128His, Arg128Ala, Arg128Cys, Arg128Glu, Arg128Ile, Arg128Lys, Arg128Asn, Arg128Gln, Arg128Ser, Arg128Thr, Arg128Val, Arg128Tyr, Gly210 missing, Ala210 missing, Gly210Thr, Ala210Thr, Gly211 missing, Gly114Glu, Ser149Ile, Val361Ala, Gly399Ala (all amino acid numbers are standardized using the PPO2 sequence of Amaranthus palmeri). Phe454Leu, Phe454Ile, and Phe454Val in the PPO1 gene of Kochia scoparia are also known as resistance mutations to saflufenacil and carfentrazone (WSSA & SWSS joint meeting, 2024). Normally, weeds have two PPO genes, PPO1 and PPO2, but the aforementioned mutations may be present in either the PPO1 or PPO2 gene, or in both. Preferably, the mutation is in the PPO2 gene. For example, Arg128Met means that there is a mutation at the 128th amino acid. In the PPO2 gene of ragweed, this mutation corresponds to the 98th position (Weed Science 60, 335-344), and is known as Arg98Leu, but this Arg98 is synonymous with Arg128 in this specification.In the PPO genes of the weeds targeted for control in this invention, Arg128Met and Arg128Gly are known in Amaranthus philoxeroides (Pest Management Science 73, 1559-1563), Arg128Gly is known in the PPO2 of water hemp (Pest Management Science, 2019; 75: 3235-3244), Arg128Ile and Arg128Lys are known in the PPO2 of water hemp (Pest Management Science, 2019; 75: 3235-3244), Arg128His is known as Arg132His in the PPO2 of Elymus (WSSA annual meeting, 2018), and Gly114Glu, Ser149Ile, Val361Ala and Gly399Ala are known in the PPO2 of Amaranthus philoxeroides (Frontiers (Plant Science 10, Article 568 and Plants 2023, 12(9), 1886) Ala210Thr is known as Ala212Thr in PPO1 of goosegrass (Pest Management Science, doi: 10.1002 / ps.5703). The present invention effectively controls PPO inhibitor-resistant weeds having these site mutations, but the PPO inhibitor-resistant weeds that are controlled are not limited to these. In other words, not only are Amaranthus philoxeroides (also known as amaranth) with mutations in PPO1 or PPO2 such as Arg128Leu, Arg128Met, Arg128Gly, Arg128His, Arg128Ala, Arg128Cys, Arg128Glu, Arg128Ile, Arg128Lys, Arg128Asn, Arg128Gln, Arg128Ser, Arg128Thr, Arg128Val, Arg128Tyr, Gly210 deficiency, Ala210 deficiency, Gly210Thr, Ala210Thr, Gly211 deficiency, Gly114Glu, Ser149Ile, or Gly399Ala effectively controlled, but also, for example, water hemp, ragweed, and Euphorbia hemp with the same mutations.Examples of reduced weed susceptibility due to non-point mutations include water hemp and Amaranthus oleifera that have become resistant to PPO inhibitors due to the involvement of CYP or GST, and water hemp that have become resistant to carfentrazone ethyl (PLOS ONE, doi: 10.1371 / journal.pone.0215431). These can be effectively controlled by the present invention. Auxin herbicide resistance: An example of a point mutation is a mutation that causes Gly-Asn in the degron region of the AUX / IAA gene. This invention allows for the effective control of Kochia scoparia, Amaranthus oleifera, and water hemp that possess this mutation. Examples of non-point mutations include Amaranthus oleifera resistant to dicamba, in which the involvement of CYP is suggested, and water hemp resistant to 2,4-D. These can be effectively controlled by the present invention. The same applies to non-point mutations involving GST. HPPD inhibitor resistance: An example of HPPD inhibitor resistance involving the site of action is increased expression of the HPPD gene (Frontiers in Plant Science, 2017, 8: 555). Examples of reduced weed susceptibility due to non-site of action mutations include water hemp and Amaranthus philoxeroides, which have become resistant to HPPD inhibitors due to the involvement of CYP or GST, and these can be effectively controlled by the present invention. Examples of such weeds include Amaranthus philoxeroides with overexpression of CYP72A219, CYP81B, and CYP81E8. Photosystem II inhibitor resistance: An example of reduced weed susceptibility due to site of action mutations is weeds with mutations in the psbA gene that cause one or more of the following amino acid substitutions: Val219Ile, Ser264Gly, Ser264Ala, Phe274Val. The present invention effectively controls amaranth and water hemp that are resistant to photosystem II inhibitors and possess these site-of-action mutations. Examples of reduced susceptibility of weeds due to non-site-of-action mutations include amaranth and water hemp, which are resistant to photosystem II inhibitors due to the involvement of CYP, GST, or AAA, and the present invention effectively controls these.One example of such a mutation is that of oatmeal overexpressing CYP71R4. Glutamate synthase inhibitor resistance: An example of reduced weed susceptibility due to site-of-action mutations is weeds with mutations in the glutamine synthase gene that cause an amino acid substitution at Asp171Asn. The present invention effectively controls glutamine synthase inhibitor-resistant weeds such as Amaranthus philoxeroides and water hemp that possess this mutation. An example of glutamine synthase inhibitor resistance involving the site of action is an increase in the copy number of the glutamine synthase gene (Weed Science, 2022, 70.4: 370-379). An example of reduced weed susceptibility due to non-site-of-action mutations is Amaranthus philoxeroides and water hemp that have become glufosinate-resistant due to the involvement of CYP or GST, and the present invention effectively controls these weeds. Examples of such weeds include Amaranthus philoxeroides, which overexpresses CYP72A219, CYP81B, and CYP81E8. Resistant weeds are also effectively controlled even if they "stack" resistance to two or more of the above groups (any two, any three, any four, any five, any six, any seven, or any eight). An example of a stacked resistant weed is water hemp, which is resistant to all of photosystem II inhibitors, HPPD inhibitors, 2,4-D, PPO inhibitors, ALS inhibitors, and glyphosate, and this too is effectively controlled. The above stacking may be due to a combination of site-of-action mutations, a combination of non-site-of-action mutations, or a combination of site-of-action and non-site-of-action mutations.

[0073] The compound or composition A of the present invention is typically used by mixing it with an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier and a surfactant, and adding formulation aids such as binders, dispersants, and stabilizers as needed, to formulate it into aqueous suspensions, oily suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, granular wettable powders, powders, granules, tablets, aerosols, resin formulations, etc. It is not limited to these formulations, but can also be formulated and used in the dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain the compound or composition A of the present invention in an amount of 0.0001 to 99% by weight.

[0074] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0075] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0076] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0077] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).

[0078] Other pharmaceutical additives include binders, dispersants, colorants, and stabilizers. Specifically, examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and dibutylhydroxytoluene.

[0079] Furthermore, adjuvants can be used as components to enhance or support the efficacy of the compounds of the present invention. Specifically, examples include Nimbus®, Assist®, Aureo®, Iharol®, Silwet L-77®, BreakThru®, SundanceII®, Induce®, Penetrator®, AgriDex®, Lutensol A8®, NP-7®, Triton®, Nufilm®, Emulgator NP7®, Emulad®, TRITON X 45®, AGRAL 90®, AGROTIN®, ARPON®, EnSpray N®, and BANOLE®.

[0080] The compound of the present invention can be used in agricultural land where useful plants are cultivated to control weeds in said agricultural land. Examples of the useful plants mentioned above include the following:

[0081] Corn (Horsetail, hard-grain, soft-grain, popping, glutinous, sweet, field corn), rice (long-grain, short-grain, medium-grain, Japonica, tropical Japonica, Indica, Javanica, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each with winter wheat type and spring wheat type), barley (two-row barley (= malting barley), six-row barley, hulless barley, glutinous barley, each with winter barley type and spring barley type), rye (winter rye type, spring rye) ), Triticare (winter Triticare type, spring Triticare type), oats (winter oat type, spring oat type), sorghum, cotton (Upland variety, Pima variety), soybeans (mature seed harvest varieties, edamame varieties, green harvest varieties, each with infinite growth type, finite growth type, and semi-finite growth type), peanuts, buckwheat, sugar beets (for sugar production, for animal feed, root vegetables, leafy vegetables, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflowers (for oil extraction, for food, for ornamental purposes), sugarcane, tobacco, tea plants, mulberry, nightshade vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radishes, turnips, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Apiaceae vegetables (carrots, parsley, celery, angelica tree, etc.), Amaranthaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, sorghum Potatoes, pomelo (apples, European pears, Japanese pears, Chinese pears, quince, marzipan, etc.), drupes (peaches, plums, nectarines, apricots, cherries, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Grasses, pasture grasses.

[0082] The useful plants listed above are not limited to any commonly cultivated varieties. These include plants that can be produced through natural cross-pollination, plants that can arise from spontaneous mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants conferred with resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutol, ALS (acetolactate synthase) inhibitors such as imazetapyr and thifensulfuron-methyl, EPSP (5-enolpyruvirshikimate-3-phosphate synthase) inhibitors, glutamine synthase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or herbicides such as dicamba; plants capable of synthesizing selective toxins known from the Bacillus genus, such as Bacillus thuringiensis; and plants that can be conferred with specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) within the target harmful insect.

[0083] The weed control method of the present invention includes the step of applying an effective amount of the compound of the present invention to weeds or to a place where weeds grow or are likely to grow. The weed control method of the present invention applies to an area of ​​10,000 m² where weeds are to be controlled. 2 Typically, 5 to 5,000 g, preferably 10 to 1,000 g, of the compound of the present invention is used per application. When applying the compound of the present invention or composition A, spraying equipment can be used. Examples of equipment used for application include hand-cranked sprayers, power sprayers, Pankle sprayers, manned aircraft (such as manned helicopters), unmanned aircraft (such as radio-controlled helicopters and drones), tractors, planters, etc. Alternatively, application may be done by hand without using spraying equipment.

[0084] In the weed control method of the present invention, the compound of the present invention is usually used in the form of composition A. Examples of the weed control method of the present invention include applying composition A to the stems and leaves of weeds, applying composition A to the soil surface where weeds grow or are likely to grow, mixing composition A into the soil where weeds grow, and applying the herbicidal composition of the present invention to the surface water of flooded paddy fields where weeds grow or are likely to grow. Methods of applying composition A include uniform area treatment or selective spot treatment. Even if a small amount of composition A is scattered in areas where weeds do not grow or are unlikely to grow due to drift or transpiration, it is included in spot treatment as long as it is not a uniform area treatment. Furthermore, spot treatment is not only considered when all areas where weeds grow or are likely to grow in a continuous area of ​​cultivated useful plants are selectively treated. In other words, even if a portion of the cultivation area is treated as a whole, or if a portion of an area where weeds are growing or are likely to grow is not treated with composition A, if there are areas that have been spot-treated within a continuous area of ​​cultivation of useful plants, it is included as spot treatment. Spot treatment may be carried out while avoiding useful plants, or it may be carried out based only on the location of weeds, regardless of the location of useful plants.

[0085] Specific examples of spot treatment methods are given below. Spot treatment may be performed in a cultivation area of ​​useful plants by a sprayer walking, or by a sprayer riding on a ground-based vehicle or flying vehicle, visually spraying composition A using a handheld nozzle or a robotic arm nozzle. Furthermore, spot treatment may be performed by mapping areas where weeds are growing or are likely to grow in advance, and spraying the compound of the present invention or composition A based on the map information. In spraying based on map information, in addition to the above method, spot treatment may be performed by automatically or manually opening and closing the nozzle on the boom or a robotic arm nozzle while the sprayer is moving or flying, based on the sprayer's position information (obtained by GPS, etc.) and the map information. The map information may be created based on image information taken by a manned or unmanned flying object, etc., or it may be created visually by an observer walking on the ground, an observer riding on a ground-based vehicle, or an observer riding on a flying vehicle. Furthermore, a mobile or flying sprayer may be equipped with a function to detect areas where weeds are growing or are likely to grow, and spot treatment may be performed using the boom or robotic arm while performing real-time mapping. Such technologies are described in patent documents (for example, International Publication No. 2018 / 001893, International Publication No. 2018 / 036909) and non-patent documents (for example, Crop Protection 26, 270-277, Weed Technology 17, 711-717, Applied Engineering in Agriculture 30, 143-152). These technologies are a form of emerging agriculture, also known as precision agriculture, smart agriculture, or digital agriculture, and the non-uniform spraying pattern resulting from the spot treatment is also called VRA (Variable Rate Application) in the terminology of this emerging agriculture. Areas where weeds are likely to grow may be estimated based on the fact that the weeds formed vegetation patches during past growing seasons, or they may be estimated from the distribution of buried seeds. The distribution of buried seeds may be investigated by soil sampling or estimated by remote sensing.

[0086] The present invention will be described in more detail below with reference to manufacturing examples, reference manufacturing examples, formulation examples, and test examples, but the present invention is not limited to these examples. In this specification, cPy represents a cyclopropyl group and iPr represents an isopropyl group.

[0087] First, we will show examples of the production of the compound of the present invention and its intermediate.

[0088] Reference Manufacturing Example 1: Intermediate product 1 was manufactured according to the following scheme (STEP 1 and STEP 2).

[0089] STEP 1: Preparation of ethyl 2-diazo-3-(2-(difluoromethoxy)-6-fluorophenyl)-3-oxopropanoate acetonitrile solution (hereinafter referred to as Solution A) A mixture of 5.01 g of ethyl 2-(difluoromethoxy)-6-fluoro-β-oxobenzenepropanoate, 2.20 g of triethylamine, and 45.3 mL of acetonitrile was mixed with 4.35 g of 4-acetamidobenzenesulfonate and 8.8 mL of acetonitrile under ice cooling. This mixture was stirred at room temperature for 3 hours. The resulting slurry was filtered, and the filtrate was further washed with 30 mL of acetonitrile. The resulting filtrate was used as Solution A in STEP 2.

[0090] STEP 2: Preparation of ethyl 3-(2-difluoromethoxy)-6-fluorophenyl)-2-hydrazineylidene-3-oxopropanoate To solution A obtained in STEP 1, 4.94 g of tributylphosphine was added under ice cooling and stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure, and the residue was subjected to silica gel chromatography (hexane:ethyl acetate = 2:1) to obtain 4.56 g of intermediate 1 shown in the following formula. Intermediate 1: 1 H-NMR (CDCl3) δ: 7.43-7.31 (1H, m), 7.04-6.93 (2H, m), 6.47 (1H, m), 4.37 (1.5H, q), 4.16 (0.5H, q), 1.38 (2.25H, t), 1.16 (0.75H, t).

[0091] Preparation Example 1-1 503 mg of intermediate 1, 671 mg of potassium carbonate, 294 mg of sodium iodide, 352 mg of 2-(chloromethyl)-5-fluoropyridine, and 5.5 mL of DMF were mixed at room temperature, and the resulting mixture was stirred at 40°C for 5 hours. After cooling to room temperature, water was added to the resulting mixture and extracted with methyl tert-butyl ether (hereinafter referred to as MTBE). The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain 210 mg of compound 2 of the present invention, shown by the following formula. Compound 2 of the present invention: 1 H-NMR (CDCl3) δ: 8.45 (1H, d), 7.63 (1H, dd), 7.52 (1H, dd), 7.41 (1H, td), 7.30 (1H, dd), 7.21 (1H, dd), 6.74 (1H, t), 5.72 (2H, s), 4.47 (2H, q), 1.43 (3H, t).

[0092] Preparation Example 1-2 505 mg of intermediate 1, 464 mg of potassium carbonate, 238 mg of sodium iodide, 396 mg of 2-chloro-5-(chloromethyl)thiazole, and 5.5 mL of DMF were mixed at room temperature, and the resulting mixture was stirred at 40°C for 4.5 hours. After cooling to room temperature, water was added to the resulting mixture and extracted with methyl tert-butyl ether (hereinafter referred to as MTBE). The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain 98 mg of compound 25 of the present invention, represented by the following formula. Compound 25 of the present invention: 1 H-NMR (CDCl3) δ: 7.74 (1H, dd), 7.61 (1H, s), 7.40 (1H, dd), 7.28-7.25 (1H, m), 6.73 (1H, t), 5.69 (2H, d), 4.47 (2H, q), 1.43 (3H, t).

[0093] Preparation Example 2-1 133 mg of Compound 2 of the present invention was mixed with 0.6 mL of 2 M lithium hydroxide aqueous solution and 3.0 mL of THF, and stirred at room temperature for 1.5 hours. MTBE and water were added to the resulting mixture, and it was extracted with 1 M sodium hydroxide aqueous solution. 10% hydrochloric acid was added to the resulting aqueous layer, and then it was extracted with ethyl acetate. The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 111 mg of Compound 27 of the present invention, represented by the following formula. Compound 27 of the present invention: 1 H-NMR (CDCl3) δ: 8.42 (1H, s), 7.89-7.79 (2H, m), 7.46-7.36 (2H, m), 7.38 (1H, d), 6.72 (1H, t), 5.96 (2H, s).

[0094] Preparation Example 2-2 64 mg of compound 25 of the present invention was mixed with 0.2 mL of 2 M lithium hydroxide aqueous solution and 1.0 mL of THF, and stirred at room temperature for 4 hours. MTBE and water were added to the resulting mixture, and it was extracted with 1 M sodium hydroxide aqueous solution. 10% hydrochloric acid was added to the resulting aqueous layer, and then it was extracted with ethyl acetate. The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 54 mg of compound 53 of the present invention, represented by the following formula. Compound 53 of the present invention: 1 H-NMR (CDCl3) δ: 7.93 (1H, dd), 7.67 (1H, s), 7.62 (1H, d), 7.44 (1H, dd), 6.73 (1H, t), 5.96 (2H, s).

[0095] Reference Manufacturing Example 2: Intermediate 2 was manufactured according to the following scheme. A mixture of 4.16 g of ethyl 3-(2,6-difluorophenyl)-3-oxopropanoate, 2.23 g of triethylamine, and 35.02 g of acetonitrile was added to a mixture of 4.65 g of 4-acetamidobenzenesulfone azide and 5.66 g of acetonitrile under ice cooling, and the mixture was stirred at room temperature for 2 hours. To the resulting slurry, 3.55 g of tributylphosphine was added under ice cooling, and the mixture was stirred at room temperature for 6 hours. Water was added to the resulting mixture, and it was extracted with MTBE. The resulting organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain 3.71 g of intermediate 2, shown in the following formula. Intermediate 2: 1 H-NMR (CDCl3) δ: 7.43-7.18 (1H, m), 6.96-6.85 (2H, m), 4.37 (1.7H, q), 4.21 (0.3H, m), 1.38 (2.5H, t), 1.20 (0.5H, t).

[0096] Preparation Example 5: 450 mg of intermediate 2, 486 mg of potassium carbonate, 53 mg of sodium iodide, 341 mg of 5-chloro-2-(chloromethyl)pyridine, and 5.9 mL of DMF were mixed at room temperature and stirred at 40°C for 3 hours. After cooling to room temperature, water was added to the resulting mixture and extracted with MTBE. The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain 323 mg of compound 22 of the present invention, represented by the following formula. Compound 22 of the present invention: 1 H-NMR (CDCl3) δ: 8.55 (1H, d), 7.68-7.56 (2H, m), 7.32 (1H, d), 7.21 (1H, d), 7.06 (1H, dd), 5.69 (2H, s), 4.48 (2H, q), 1.44 (3H, t).

[0097] Preparation Example 6 332 mg of the present invention compound 22, 4.6 mL of DMF, and 1.12 g of sodium methylsulfinate were mixed at room temperature and then stirred at 90°C for 10 hours. After cooling to room temperature, water was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:2) to obtain 299 mg of the present invention compound 55, represented by the following formula. Compound 55 of the present invention: 1 H-NMR (CDCl3) δ: 8.54 (1H, d), 8.41 (1H, dd), 7.94 (1H, dd), 7.81 (1H, dd), 7.68 (1H, dd), 7.26-7.23 (1H, m), 5.77 (2H, s), 4.48 (2H, q), 3.69 (3H, s), 1.43 (3H, t).

[0098] Preparation Example 7 A mixture of 900 mg of ethyl 3-(2-bromo-6-fluorophenyl)-2-hydrazineylidene-3-oxopropanoate and 9.5 mL of DMF was mixed with 785 mg of potassium carbonate and 552 mg of 5-chloro-2-(chloromethyl)pyridine at room temperature. The resulting mixture was stirred at 40°C for 4.5 hours. Water was added to the resulting mixture and extracted with MTBE. The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain 346 mg of compound 23 of the present invention, represented by the following formula. Compound 23 of the present invention: 1 H-NMR (CDCl3) δ: 8.55 (1H, d), 7.68-7.62 (2H, m), 7.50 (1H, dd), 7.40 (1H, dd), 7.19 (1H, d), 5.68 (2H, s), 4.48 (2H, q), 1.44 (3H, t).

[0099] Preparation Example 8: 200 mg of the present invention compound 23, 67 mg of zinc cyanide, 81 mg of tetrakis(triphenylphosphine)palladium, and 1.6 mL of DMF were mixed at room temperature and then stirred at 120°C for 4 hours. After cooling to room temperature, the resulting mixture was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:2) to obtain 89 mg of the present invention compound 56, represented by the following formula. Compound 56 of the present invention: 1 H-NMR (CDCl3) δ: 8.53 (1H, d), 7.91 (1H, d), 7.83 (1H, d), 7.76 (1H, d), 7.68 (1H, dd), 7.28 (1H, d), 5.74 (2H, s), 4.49 (2H, q), 1.44 (3H, t).

[0100] Preparation Example 9: 1.14 g of intermediate 1, 1.03 g of potassium carbonate, 158 mg of sodium iodide, 788 mg of 2-(chloromethyl)-5-(methylthio)pyridine, and 10.18 g of DMF were mixed at room temperature, and the resulting mixture was stirred at 40°C for 8.5 hours. After cooling to room temperature, water was added to the resulting mixture and extracted with MTBE. The resulting organic layer was sequentially washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain 463 mg of compound 63 of the present invention, represented by the following formula. Compound 63 of the present invention: 1 H-NMR (CDCl3) δ: 8.45 (1H, d), 7.62 (1H, dd), 7.55-7.49 (2H, m), 7.19 (1H, dd), 7.16 (1H, d), 6.74 (1H, t), 5.69 (2H, s), 4.47 (2H, q), 2.49 (3H, s), 1.43 (3H, t).

[0101] Preparation Example 10 A mixture of 275 mg of the present invention compound 63 and 6.56 g of chloroform was mixed with 222 mg of 3-chloroperbenzoic acid (>65%) under ice cooling, and then stirred at room temperature for 3 hours. A 10% aqueous solution of sodium bisulfite was added to the resulting mixture and extracted with chloroform. The resulting organic layer was sequentially washed with satu...

Claims

Equation (I) [During the ceremony, R 1 This represents a 3-10 membered heterocyclic group which may be substituted with one or more substituents selected from group A. R 2 This includes hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, carboxyl groups, aminocarbonyl groups, and aminosulfonyl groups. C1-C6 chain hydrocarbon group {The C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, C3-C8 alicyclic hydrocarbon group {The C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, -Z 2 R 2a base, -C(=O)R ２ａ base, -C(=O)OR ２ａ group, -C(=O)NR ２ａ R ２ｂ base, -SO ２ NR ２ａ R ２ｂ base, C6-C10 aryl group, 5-10 member aromatic heterocyclic group, 5-10 member non-aromatic heterocyclic group, C6-C10 aryloxy group {The C6-C10 aryl group, the 5-10 member aromatic heterocyclic group, the 5-10 member non-aromatic heterocyclic group, and the C6-C10 aryloxy group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 This represents, Z ２ is an oxygen atom, -S(O) ｎ -, or -NR 2ｂ - represents, R ２ａ This represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, R ２ｂ This represents a hydrogen atom, a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, n represents 0, 1, or 2. R 3 , R 4 , and R 5 These are the same or different hydrogen atoms, halogen atoms, cyano groups, nitro groups, amino groups, hydroxyl groups, formyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthio groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups C1-C6 hydrocarbon group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)sulfinyl group, (C1-C6 alkyl)sulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl The group, the (C1-C6 alkoxy)carbonyl group, the C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)sulfinyl group, the (C1-C6 alkyl)sulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F, C3-C8 alicyclic hydrocarbon C6-C10 aryl group {The C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, C6-C10 aryl group, 5-10 member aromatic heterocyclic group, 5-10 member non-aromatic heterocyclic group, C6-C10 aryloxy group {The C6-C10 aryl group, the 5-10 member aromatic heterocyclic group, the 5-10 member non-aromatic heterocyclic group, and the C6-C10 aryloxy group may be substituted with one or more substituents selected from group G}, or C(R 8 ) = N - OR 9 This represents, R 6 , and R 7 R represents the same or different hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, C1-C3 alkoxy group, or C1-C3 alkylthio group {the C1-C3 alkyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted with one or more halogen atoms}, or R 6 and R 7 These two groups combine to represent an oxo group, a thioxo group, or a methylidene group. R 8 This represents a hydrogen atom, a C1-C6 alkyl group {the C1-C6 alkyl group may be substituted with one or more substituents selected from group H}, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group I}, R 9 This represents a hydrogen atom or a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group I}, R 10 This represents a hydrogen atom, a C1-C10 chain hydrocarbon group {the C1-C10 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, or a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J}, R 11 This represents a C1-C10 chain hydrocarbon group {the C1-C10 chain hydrocarbon group may be substituted with one or more substituents selected from group F}, a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, a benzyl group {the phenyl portion of the benzyl group may be substituted with one or more substituents selected from group G, and the methylene portion may be substituted with one or more substituents selected from group J}, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, R 12 This represents a 5-10 member aromatic heterocyclic group {the 5-10 member aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, X 1 and X 2 These represent the same or different oxygen or sulfur atoms. Y 1 is, Z 1 R 10 group, NHS(O)2R 11 , or NHR 12 This represents, Z 1 This represents an oxygen atom or a sulfur atom. 　 Group A: Halogen atom, cyano group, nitro group, hydroxyl group, amino group, formyl group, hydroxyl group, aminocarbonyl group, aminosulfonyl group, C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C2-C6 alkenyloxy group, C2-C6 alkynyloxy group, C1-C6 alkylthio group, C2-C6 alkenylthio group, C2-C6 alkynylthio group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, ( C2-C8 dialkylamino)carbonyl group, C1-C6 alkylsulfinyl group, C2-C6 alkenylsulfinyl group, C2-C6 alkynylsulfinyl group, C1-C6 alkylsulfonyl group, C2-C6 alkenylsulfonyl group, C2-C6 alkynylsulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C2-C6 alkenyloxy group, the C2-C6 alkynyloxy group, the C1-C6 alkylthio group, the C2-C6 alkenyl Luthio group, the C2-C6 alkynylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C2-C6 alkenylsulfinyl group, the C2-C6 alkynylsulfinyl group, the C1-C6 alkylsulfonyl group, the C2-C6 alkenylsulfonyl group, the C2-C6 alkynylsulfonyl group, the (C1-C 6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group may be substituted with one or more substituents selected from group F}, C3-C6 cycloalkyloxy group, C3-C6 cycloalkenyloxy group, C3-C6 cycloalkylthio group, C3-C6 cycloalkenylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkenylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C3-C6 cycloalkenylsulfonyl group, C3-C6 alicyclic hydrocarbon group {the C3-C6 cycloalkyloxy group,The C3-C6 cycloalkenyloxy group, the C3-C6 cycloalkylthio group, the C3-C6 cycloalkenylthio group, the C3-C6 cycloalkylsulfinyl group, the C3-C6 cycloalkenylsulfinyl group, the C3-C6 cycloalkylsulfonyl group, the C3-C6 cycloalkenylsulfonyl group, and the C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from group E}, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group, 5-10 membered non-aromatic heterocyclic group {the C6-C10 aryl group, the 5-10 membered aromatic heterocyclic group, and the 5-10 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, and C(R, 13 ) = N - OR 14 A group consisting of these elements. R 13 This represents a hydrogen atom, a C1-C6 alkyl group {the C1-C6 alkyl group may be substituted with one or more substituents selected from group H}, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group I}, R 14 This represents a hydrogen atom or a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group I}. 　 Group E: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group F: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {The C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group G: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, formyl groups, aminocarbonyl groups, C1-C3 alkyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {The C1-C3 alkyl group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group H: A group consisting of halogen atoms, cyano groups, nitro groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group I: A group consisting of halogen atoms, cyano groups, nitro groups, formyl groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C3-C5 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {The C1-C3 alkyl group, the C3-C5 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. Group J: A group consisting of halogen atoms, cyano groups, C1-C6 alkyl groups, C1-C6 alkoxy groups, and C1-C6 alkylthio groups {the C1-C6 alkyl group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group may be substituted with one or more halogen atoms}. Compounds shown (However, R 2 , R 3 , R 4 , and R 5 Compounds in which hydrogen atoms are present; and, R 2 , R 3 , and R 4 is a hydrogen atom, R 5 (Excluding compounds in which the atom is a chlorine atom.) Or its salt. Group E is a group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C1-C3 alkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups {the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. The compound or salt thereof according to claim 1, wherein group F is the group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the (C1-C3 alkoxy)carbonyl group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}. X 1 and X 2 The compound or salt thereof according to claim 1 or 2, wherein the compound is an oxygen atom. Y 1 However, OR 10 group, NHS(O)2R 11 , or NHR 12 The compound or salt thereof according to any one of claims 1 to 3. Y 1 However, OR 10 A compound or salt thereof according to any one of claims 1 to 3, which is a base. R 6 , and R 7 However, the same or different hydrogen atoms, halogen atoms, cyano groups, C1-C3 alkyl groups, or C1-C3 alkoxy groups {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, or R 6 and R 7 The compound or salt thereof according to any one of claims 1 to 5, wherein the two groups combine to form an oxo group. R 6 , and R 7 The compound or salt thereof according to any one of claims 1 to 5, wherein the compound is a hydrogen atom. R 3 , R 4 , and R 5 The compound or salt thereof according to any one of claims 1 to 7, wherein the hydrogen atom, halogen atom, cyano group, C1-C3 alkyl group, and C1-C3 alkoxy group are the same or different in phase {the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more substituents selected from group F}. R 3 , R 4 , and R 5 The compound or salt thereof according to any one of claims 1 to 7, wherein the compound is a hydrogen atom. R ２ However, halogen atoms, cyano groups, C1-C3 alkyl groups, C2-C3 alkenyl groups, C2-C3 alkynyl groups, C1-C3 alkoxy groups, C2-C3 alkenyloxy groups, C2-C3 alkynyloxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, C1-C3 alkylsulfonyl groups {the C1-C3 alkyl group, the C2-C3 alkenyl group, the C2-C3 alkynyl group, the C1-C3 alkoxy group, the C2-C3 alkenyloxy group, the C2-C3 alkynyloxy group, the C1-C3 alkylthio group, the (C1-C3 alkyl)carbonyl group, the (C1 C3-C5 cycloalkyl group, C3-C5 alkylsulfinyl group, and C3-C5 alkylsulfonyl group may be substituted with one or more substituents selected from group F}, C3-C5 cycloalkyl group, C3-C5 cycloalkyloxy group, C3-C5 cycloalkylthio group, C3-C5 cycloalkylsulfinyl group, C3-C5 cycloalkylsulfonyl group {the C3-C5 cycloalkyl group, C3-C5 cycloalkyloxy group, C3-C5 cycloalkylthio group, C3-C5 cycloalkylsulfinyl group, and C3-C5 cycloalkylsulfonyl group may be substituted with one or more substituents selected from group E}, or C(R 8 ) = N - OR 9 The compound or salt thereof according to any one of claims 1 to 9. R ２ The compound or salt thereof according to any one of claims 1 to 9, wherein the compound is a halogen atom, a cyano group, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, or a C1-C3 alkylsulfonyl group {the C1-C3 alkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from group F}. R 1 The compound or salt thereof according to any one of claims 1 to 11, wherein the compound is a 5-6 member aromatic heterocyclic group which may be substituted with one or more substituents selected from group A {the heteroatoms constituting the 5-6 member aromatic heterocyclic group are nitrogen atoms, oxygen atoms, or sulfur atoms, and the number of heteroatoms is 1, 2, 3, or 4}. 　 A herbicidal composition comprising a compound or salt thereof according to any one of claims 1 to 12 and an inert carrier. 　 A method for controlling weeds, comprising the step of applying a compound or salt thereof described in any one of claims 1 to 12 to weeds or soil in which weeds grow. 　 Use of a compound or salt thereof according to any one of claims 1 to 12 for controlling weeds. 　 A composition containing one or more components selected from the group consisting of group (d) and group (f), and a compound or salt thereof as described in any one of claims 1 to 12: Group (d): Ingredients that reduce drug-induced harm; Group (f): herbicidal active ingredients.

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