Phenylacetic acid derivatives, their uses and intermediates for their production

Abstract

The present invention provides a compound having an excellent control effect against pests. A compound represented by formula (1) of the present invention (in the formula, Q represents a group indicated by Q1 or a group indicated by Q2 (● represents a binding site with a benzene ring), E represents a C5-C6 cycloalkenyl group or the like, L represents an oxygen atom or NH, the combination of R1 and n represents a combination or the like in which R1 is a hydrogen atom and n is 1, and R2 represents a methyl group or the like), an N-oxide thereof, or an agriculturally acceptable salt thereof has an excellent control effect against pests.

Description

[Technical Field]

[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application No. 2020-015186 (filed January 31, 2020), the entire contents of which are incorporated herein by reference. The present invention relates to phenylacetic acid derivatives, their uses and intermediates for the preparation thereof. [Background technology]

[0002] Patent Document 1 describes phenylacetic acid derivatives. [Prior art documents] [Non-patent literature]

[0003] [Patent Document 1] European Patent Application Publication No. 422597 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a compound having excellent pesticidal activity against pests. [Means for solving the problem]

[0005] The present inventors have conducted research to find a compound having excellent control activity against pests, and as a result have found that a compound represented by the following formula (I) has excellent control activity against pests. That is, the present invention is as follows. [1] Formula (I): [ka] [During the ceremony, Q represents a group represented by Q1 or a group represented by Q2 (● represents the bonding site to the benzene ring); [ka] E is a C5-C6 cycloalkenyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group, each of which may be substituted with one or more substituents selected from Group D (the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group A), R 7 -C≡C-, R 5 -ON=C(R 4 )-, R 8 -N=C(R 4 )- or R 6 represents O-, L represents an oxygen atom or NH; R 1 and the combination of n is R 1 is a hydrogen atom and n is 1; or R 1 represents a combination in which n is 0, and n is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a methoxy group, a cyclopropyl group, or a halogen atom; R 2 represents a methyl group, a cyclopropyl group, or a halogen atom; R 4 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 5 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, or R 18 represents -CH2-, R 7 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, or a 5- or 6-membered aromatic heterocyclic group {the 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group C}, R 6 represents a methyl group substituted with one or more substituents selected from group F, a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C4 cycloalkyl group optionally substituted with one or more substituents selected from group D, or R 13 R 4 represents NC(O)-, R 8 and R 13 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, or R 10 -(CH2) m - represents m represents 1 or 2; R 10 and R 18 are the same or different and represent a phenyl group or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}. Group A: a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group D, a C1-C6 alkylthio group optionally substituted with one or more substituents selected from Group F, OR 14 , C(O)R 11 , C(O)OR 11 , N.R. 11 R 9 , C(R 9 )=N-OR 11 the group consisting of a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group E}, a halogen atom, a cyano group, and a nitro group. R 9 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R11 and R 14 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group D, a phenyl group, or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group C}. Group C: a group consisting of C1-C3 chain hydrocarbon groups, C3-C4 cycloalkyl groups, C1-C3 alkoxy groups, and C1-C3 alkylthio groups (the C1-C3 chain hydrocarbon groups, C3-C4 cycloalkyl groups, C1-C3 alkoxy groups, and C1-C3 alkylthio groups may be substituted with one or more halogen atoms), halogen atoms, cyano groups, nitro groups, and hydroxy groups. Group D: A group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group. Group E: a group consisting of C1-C3 open chain hydrocarbon groups, C3-C4 cycloalkyl groups, C1-C3 alkoxy groups, and C1-C3 alkylthio groups {the C3-C4 cycloalkyl groups, C1-C3 alkoxy groups, and C1-C3 alkylthio groups may be substituted with one or more halogen atoms}, halogen atoms, cyano groups, nitro groups, and hydroxy groups. Group F: a group consisting of a C3-C4 cycloalkyl group, a C1-C3 alkoxy group, and a halogen atom. (hereinafter referred to as compound N of the present invention), or an N-oxide or an agriculturally acceptable salt thereof (hereinafter, a compound represented by formula (I) or an N-oxide or an agriculturally acceptable salt thereof will be referred to as compound of the present invention). [2] E is a C5-C6 cycloalkenyl group optionally substituted with one or more substituents selected from Group D, a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group H}, R 7 -C≡C-, R 5 -ON=C(R 4 )- or R 6 O-, R4 is a C1-C3 alkyl group or a hydrogen atom, R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or R 18 -CH2-, R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or R 13 R 4 NC(O)-, R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 11 and R 13 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 14 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from group G, R 18 is a phenyl group or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group G}, or an N-oxide or an agriculturally acceptable salt thereof. Group G: a group consisting of C1-C3 chain hydrocarbon groups, C1-C3 alkoxy groups {the C1-C3 chain hydrocarbon groups and the C1-C3 alkoxy groups may be substituted with one or more halogen atoms}, halogen atoms, and cyano groups. Group H: C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents, C3-C4 cycloalkyl groups optionally substituted with one or more halogen atoms, OR 14 , halogen atoms, cyano groups, C(R 4 )=N-OR 11 a phenyl group, and a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [3] E is R 7 -C≡C-, R 5 -ON=C(R 4 )-, R 6 O-, a phenyl group, a pyridyl group, a thienyl group, a furanyl group, a pyrimidinyl group, a thiadiazolyl group, or a pyrazolyl group {the phenyl group, the pyridyl group, the thienyl group, the furanyl group, the pyrimidinyl group, the thiadiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group I}, R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or R 18 -CH2-, R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, R 11 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, R 14 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from group G, R 18is a phenyl group optionally substituted with one or more substituents selected from group G, or an N-oxide or an agriculturally acceptable salt thereof, according to [2]. Group I: a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a cyclopropyl group, OR 14 , halogen atoms, cyano groups, C(R 4 )=N-OR 11 a phenyl group, a pyridyl group, and a pyrazolyl group {the phenyl group, the pyridyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group G}. [4] E is R 7 -C≡C-, a phenyl group, a pyridyl group, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the phenyl group, the pyridyl group, the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J}, or a pyrimidinyl group {the pyrimidinyl group is optionally substituted with one or more substituents selected from Group K}, R 7 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a cyclopropyl group, or an N-oxide or an agriculturally acceptable salt thereof according to [2]. Group J: C1-C6 chain hydrocarbon groups, C1-C3 alkoxy groups {the C1-C6 chain hydrocarbon groups and the C1-C3 alkoxy groups may be substituted with one or more substituents selected from Group F}, cyclopropyl groups, halogen atoms, cyano groups, C(R 4 )=N-OR 11 a phenyl group, a pyridyl group, and a pyrazolyl group {the phenyl group, the pyridyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group G}. Group K: A group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenoxy group optionally substituted with one or more substituents selected from Group G, and a halogen atom. [5] R 1is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, n is 0, The compound according to any one of [1] to [4], or an N-oxide or an agriculturally acceptable salt thereof. [6] Q is a group represented by Q1, R 1 is a methyl group, n is 0, The compound according to any one of [1] to [4], or an N-oxide or an agriculturally acceptable salt thereof. [7] A pesticide composition containing the compound according to any one of [1] to [6], or an N-oxide or an agriculturally acceptable salt thereof, and an inert carrier. [8] A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound according to any one of [1] to [6], or an N-oxide or an agriculturally acceptable salt thereof: Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): Fungicidally active ingredients; Group (c): Plant growth regulating components; Group (d): repellent ingredients. [9] A method for controlling pests, which comprises treating a plant or soil with an effective amount of the compound according to any one of [1] to [6], or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to [8].

[10] A method for controlling soybean rust fungus having an F129L amino acid substitution in mitochondrial cytochrome b protein, comprising applying an effective amount of the compound according to any one of [1] to [6], or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to [8] to soybeans or soil in which soybeans are grown.

[11] Use of the compound according to any one of [1] to [6], or an N-oxide or agriculturally acceptable salt thereof, or the composition according to [8] for controlling pests.

[12] A seed or a vegetative reproductive organ carrying an effective amount of the compound according to any one of [1] to [6], or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to [8].

[13] Formula (II): [ka] [During the ceremony, Q and E B The combination of Q is a group represented by Q1, and E B But R 12 C(O)-, R 12 C(=N-OH)-, or a halogen atom; or Q is a group represented by Q2, and E B But R 12 C(O)-, R 12 represents a combination of C(=N-OH)-, a bromine atom, or an iodine atom; The group represented by Q1 and the group represented by Q2 each represent a group represented by the following formula (● represents a bonding site to a benzene ring): [ka] L represents an oxygen atom or NH; R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a methoxy group, a cyclopropyl group, or a halogen atom; R 12 represents a C1-C3 alkyl group. A compound represented by the formula (hereinafter referred to as intermediate A). [Effects of the Invention]

[0006] The present invention makes it possible to control pests. DETAILED DESCRIPTION OF THE INVENTION

[0007] The substituents in the present invention will be explained. 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, these halogen atoms may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, and decyl groups. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, and 9-decenyl groups. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, a 5-hexynyl group, and a 9-decynyl group.

[0008] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.

[0009] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of cycloalkenyl groups include cyclopentenyl and cyclohexenyl groups.

[0010] Aryl groups include, for example, phenyl, indenyl, indanyl, naphthyl, and tetrahydronaphthyl groups. Examples of aromatic heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, indazolyl, benzimidazolyl, imidazopyridyl, benzothiophenyl, benzofuranyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl groups.

[0011] The terms used in this specification will be explained below. Soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, resulting in the F129L amino acid substitution, and is therefore resistant to QoI fungicides.

[0012] The compound of the present invention and intermediate A may exist as one or more stereoisomers. Stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio. Examples of geometric isomers include the following structures. [ka]

[0013] The compound of the present invention or its N-oxide may form an acid addition salt such as a hydrochloride, sulfate, nitrate, phosphate, acetate, or benzoate when mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid.

[0014] The following compounds are examples of the compound N of the present invention.

[0015] [Aspect 1] In the compound N of the present invention, E is R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect 2] In the compound N of the present invention, E is R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 3] In the compound N of the present invention, E is R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Embodiment 4] In the compound N of the present invention, E is R 7 -C≡C- and R 7 is a C1-C6 alkyl group or a cyclopropyl group. [Embodiment 5] A compound of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from group A in compound N of the present invention. [Embodiment 6] A compound of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group I in Compound N of the present invention. [Embodiment 7] A compound of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from group J in compound N of the present invention. [Embodiment 8] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, Group J1 includes C1-C3 alkyl groups, C1-C3 alkoxy groups (the C1-C3 alkyl groups and the C1-C3 alkoxy groups may be substituted with one or more halogen atoms), halogen atoms, cyano groups, and C(R 9 )=N-OR11 A compound that is a group consisting of: [Embodiment 9] In the compound N of the present invention, E is a group represented by formula (III): [ka] is a group represented by R 24 and R 28 are the same or different and represent a halogen atom or a hydrogen atom, R 25 and R 27 are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, C(O)R 11 , C(R 9X )=N-OR 11X , a halogen atom, a cyano group, or a hydrogen atom; R 9X and R 11X are the same or different and represent a C1-C3 alkyl group, R 26 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect 10] In aspect 9, R 24 , R 26 , and R 28 are the same or different and are a fluorine atom or a hydrogen atom, R 25 and R 27 are the same or different, and C(R 9X )=N-OR 11X , a halogen atom, a cyano group, or a hydrogen atom. [Embodiment 11] A compound of the present invention, wherein E is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group A. [Embodiment 12] A compound of the present invention, wherein E is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H in compound N of the present invention. [Embodiment 13] A compound of the present invention, wherein E is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I in Compound N of the present invention. [Embodiment 14] In compound N of the present invention, E is a pyridyl group optionally substituted with one or more substituents selected from Group J2, or a pyrimidinyl group optionally substituted with one or more substituents selected from Group K, Group J2 is a C1-C3 alkyl group, 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}, a halogen atom, and C(R 9X )=N-OR 11Y is a group consisting of R 11Y is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F. [Aspect 15] In compound N of the present invention, E is a pyridyl group optionally substituted with one or more substituents selected from Group J3, or a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, Group J3 is a group consisting of a C1-C3 alkyl group, 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}, and a halogen atom; Group K1 is a group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenoxy group optionally substituted with one or more substituents selected from Group G1, and a halogen atom; The group G1 is a compound that is a group consisting of a cyano group and a halogen atom. [Aspect 16] In the compound N of the present invention, E is a thienyl group, a furanyl group, a thiadiazolyl group, or a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group J4}, Group J4 is a compound selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, and a halogen atom. [Aspect 17] In the compound N of the present invention, E is a thienyl group, a furanyl group, a thiadiazolyl group, or a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group J5}, Group J5 includes compounds which are the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, and a halogen atom. [Embodiment 18] In the compound N of the present invention, E is a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a group represented by formula (IV-4), a group represented by formula (IV-5), a group represented by formula (IV-6), or a group represented by formula (IV-7), [ka] R 15 and R 16 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom; R 17 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; A compound in which A is a phenyl group or a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more substituents selected from group G}. [Aspect 19] Compound N of the present invention, wherein E is a group represented by formula (IV-1), a group represented by formula (IV-2), or a group represented by formula (IV-3), and A is a phenyl group optionally substituted with one or more halogen atoms. [Aspect 20] Compounds of the present invention N, wherein E is a pyridyl group optionally substituted with one or more substituents selected from Group J2, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J4}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a group represented by formula (IV-4), a group represented by formula (IV-5), a group represented by formula (IV-6), or a group represented by formula (IV-7). [Aspect 21] A compound of the present invention, wherein E is a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), or a group represented by formula (IV-3), and A is a phenyl group optionally substituted with one or more halogen atoms. [Embodiment 22] In the compound N of the present invention, E is R 5 -ON=C(R 4 )- and R 4 is a C1-C3 alkyl group or a hydrogen atom, and R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or R 18 -CH2- and R 18 is a phenyl group or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Embodiment 23] In the compound N of the present invention, E is R 5-ON=C(R 4 )- and R 4 is a C1-C3 alkyl group or a hydrogen atom, and R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or R 18 -CH2- and R 18 is a phenyl group optionally substituted with one or more substituents selected from group G. [Embodiment 24] In the compound N of the present invention, E is R 5 -ON=C(R 4 )- and R 4 is a methyl group or a hydrogen atom, and R 5 is a C1-C4 alkyl group, a C3-C4 cycloalkyl group, or R 18 -CH2- and R 18 is a phenyl group {the phenyl group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms and a halogen atom}. [Embodiment 25] In the compound N of the present invention, E is R 6 O- and R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or R 13 R 4 A compound that is NC(O)-. [Embodiment 26] In the compound N of the present invention, E is R 6 O- and R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Embodiment 27] In the compound N of the present invention, E is R 6 O- and R 6 is a C2-C6 chain hydrocarbon group. [Embodiment 28] In the compound N of the present invention, E is R 6 O- and R 6 is a C2-C6 alkyl group. [Embodiment 29] A compound of the present invention, wherein E is a C5-C6 cycloalkenyl group optionally substituted with one or more substituents selected from group D, in compound N of the present invention. [Aspect 30] A compound of the present invention, wherein E is a C5-C6 cycloalkenyl group optionally substituted with one or more halogen atoms in Compound N of the present invention. [Embodiment 31] A compound of the present invention, wherein E is a C5-C6 cycloalkenyl group in compound N. [Embodiment 32] Compound N of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group A, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group A. [Embodiment 33] Compound N of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group I, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Embodiment 34] Compound N of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group J, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I. [Aspect 35] Compound N of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group J1, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I. [Aspect 36] Compounds of the present invention N, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a pyridyl group optionally substituted with one or more substituents selected from Group J2, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J4}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a group represented by formula (IV-4), a group represented by formula (IV-5), a group represented by formula (IV-6), or a group represented by formula (IV-7). [Aspect 37] A compound of compound N of the present invention, wherein E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), or a group represented by formula (IV-3), and A is a phenyl group optionally substituted with one or more halogen atoms. [Aspect 38] A compound of the present invention, wherein E is a group represented by formula (III), a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), or a group represented by formula (IV-3), and A is a phenyl group optionally substituted with one or more halogen atoms. [Embodiment 39] In embodiment 38, R 24 , R 26 , and R 28 are the same or different and are fluorine atoms or hydrogen atoms, and R 25 and R 27 are the same or different, and C(R 9X )=N-OR 11X , a halogen atom, a cyano group, or a hydrogen atom. [Aspect 40] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group A, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group A, or R 7 -C≡C- and R 7is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect 41] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group I, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect 42] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Aspect 43] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Aspect 44] In compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a pyridyl group optionally substituted with one or more substituents selected from Group J2, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J4}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a group represented by formula (IV-4), a group represented by formula (IV-5), a group represented by formula (IV-6), a group represented by formula (IV-7), or R 7-C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Aspect 45] In compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), or R 7 -C≡C- and R 7 is a C1-C6 alkyl group or a cyclopropyl group, and A is a phenyl group optionally substituted with one or more halogen atoms. [Aspect 46] In compound N of the present invention, E is a group represented by formula (III), a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), or R 7 -C≡C- and R 7 is a C1-C6 alkyl group or a cyclopropyl group, and A is a phenyl group optionally substituted with one or more halogen atoms. [Embodiment 47] In embodiment 46, R 24 , R 26 , and R 28 are the same or different and are fluorine atoms or hydrogen atoms, and R 25 and R 27 are the same or different, and C(R 9X )=N-OR 11X , a halogen atom, a cyano group, or a hydrogen atom. [Aspect 48] In compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group A, a 5-6 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group A, a C5-C6 cycloalkenyl group optionally substituted with one or more substituents selected from Group D, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect 49] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group I, a 5-6 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, a C5-C6 cycloalkenyl group optionally substituted with one or more halogen atoms, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect 50] In the compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J, a 5-6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I, or a C5-C6 cycloalkenyl group optionally substituted with one or more halogen atoms. , or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Aspect 51] In compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a 5-6 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group I, a C5-C6 cycloalkenyl group optionally substituted with one or more halogen atoms, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Aspect 52] In compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a pyridyl group optionally substituted with one or more substituents selected from Group J2, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J4}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a group represented by formula (IV-4), a group represented by formula (IV-5), a group represented by formula (IV-6), a group represented by formula (IV-7), a C5-C6 cycloalkenyl group, or R 7 -C≡C- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group. [Aspect 53] In compound N of the present invention, E is a phenyl group optionally substituted with one or more substituents selected from Group J1, a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a C5-C6 cycloalkenyl group, or R 7 -C≡C- and R 7 is a C1-C6 alkyl group or a cyclopropyl group, and A is a phenyl group optionally substituted with one or more halogen atoms. [Aspect 54] In compound N of the present invention, E is a group represented by formula (III), a pyridyl group optionally substituted with one or more substituents selected from Group J3, a pyrimidinyl group optionally substituted with one or more substituents selected from Group K1, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from Group J5}, a group represented by formula (IV-1), a group represented by formula (IV-2), a group represented by formula (IV-3), a C5-C6 cycloalkenyl group, or R 7 -C≡C- and R 7 is a C1-C6 alkyl group or a cyclopropyl group, and A is a phenyl group optionally substituted with one or more halogen atoms. [Embodiment 55] In embodiment 54, R 24 , R 26 , and R 28 are the same or different and are fluorine atoms or hydrogen atoms, and R 25 and R 27 are the same or different, and C(R 9X )=N-OR 11X , a halogen atom, a cyano group, or a hydrogen atom. [Embodiment 56] In the compound N of the present invention, E is a phenyl group, a 5- or 6-membered aromatic heterocyclic group (the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group J1), R 7 -C≡C- or R 6 O- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group, and R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F. [Embodiment 57] In the compound N of the present invention, E is a phenyl group, a 5- or 6-membered aromatic heterocyclic group (the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group J1), R 7 -C≡C- or R 6 O- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group, and R6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Embodiment 58] In the compound N of the present invention, E is a phenyl group, a 5- or 6-membered aromatic heterocyclic group (the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group J1), R 7 -C≡C- or R 6 O- and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group, and R 6 is a C2-C6 alkyl group.

[0016] [Aspect 59] In the compound N of the present invention, E is a C5-C6 cycloalkenyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group A1), R 7 -C≡C-, R 5 -ON=C(R 4 )- or R 6 O- and R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, a phenyl group optionally substituted with one or more substituents selected from group C, or R 18 -CH2- and R 6 is a methyl group substituted with one or more substituents selected from group F, a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C4 cycloalkyl group optionally substituted with one or more substituents selected from group D, and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, and group A1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, OR 14a , C(O)R 11a, C(R 9 )=N-OR 11a , a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group, and a nitro group; R 11a represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, and R 14a represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a phenyl group, or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}. [Aspect 60] In the compound N of the present invention, E is a C5-C6 cycloalkenyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group A2), R 7 -C≡C-, R 5 -ON=C(R 4 )- or R 6 O- and R 4 is a methyl group or a hydrogen atom, and R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F1, a C3-C6 cycloalkyl group, a phenyl group, or R 18 -CH2- and R 6 is (c-Pr)CH2-, a C2-C6 chain hydrocarbon group, or a C3-C4 cycloalkyl group, and R 7 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 18 is a phenyl group or a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more substituents selected from Group C1}, and Group A2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, OR 14bGroup C1 represents a group consisting of a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms and a halogen atom; Group F1 represents a group consisting of a C3-C4 cycloalkyl group and a halogen atom; R 14b represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from Group C1. [Embodiment 61] In the compound N of the present invention, E is R 5 -ON=C(R 4 )- and R 4 is a methyl group or a hydrogen atom, and R 5 is a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or R 18 -CH2- and R 18 is a phenyl group or a pyridyl group {the phenyl group and the pyridyl group may be substituted with one or more substituents selected from Group C1}.

[0017] [Aspect 62] In any one of Aspects 1 to 61 or the present compound N, R 1 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, and n is 0. [Aspect 63] In any one of Aspects 1 to 61 or the present compound N, R 1 A compound in which is a methyl group and n is 0. [Aspect 64] In any one of Aspects 1 to 61 or the present compound N, R 1 A compound in which is a hydrogen atom and n is 1. [Aspect 65] In any one of Aspects 1 to 61 or the present compound N, R 1 is a hydrogen atom, n is 1, and R 2 is a methyl group or a halogen atom. [Aspect 66] In any one of Aspects 1 to 61 or Compound N of the present invention, R 1is a hydrogen atom, n is 1, and R 2 is a methyl group. [Aspect 67] In any one of Aspects 1 to 61 or the present compound N, R 1 is a hydrogen atom, n is 1, and R 2 A compound in which the atom is chlorine. [Aspect 68] In any one of Aspects 1 to 61 or the present compound N, R 1 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, n is 0, and Q is a group represented by Q1. [Aspect 69] In any one of Aspects 1 to 61 or Compound N of the present invention, R 1 A compound in which is a methyl group, n is 0, and Q is a group represented by Q1. [Aspect 70] In any one of Aspects 1 to 61 or Compound N of the present invention, R 1 is a hydrogen atom, n is 1, and Q is a group represented by Q1. [Aspect 71] In any one of Aspects 1 to 61 or the present compound N, R 1 is a hydrogen atom, n is 1, and R 2 is a methyl group or a halogen atom, and Q is a group represented by Q1. [Aspect 72] In any one of Aspects 1 to 61 or the present compound N, R 1 is a hydrogen atom, n is 1, and R 2 A compound in which is a methyl group and Q is a group represented by Q1. [Aspect 73] In any one of Aspects 1 to 61 or the present compound N, R 1 is a hydrogen atom, n is 1, and R 2 A compound in which is a chlorine atom and Q is a group represented by Q1. [Aspect 74] In any one of Aspects 1 to 61 or the present compound N, R 1 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, n is 0, and Q is a group represented by Q2. [Aspect 75] In any one of Aspects 1 to 61 or Compound N of the present invention, R1 A compound in which is a methyl group, n is 0, and Q is a group represented by Q2. [Aspect 76] In any one of Aspects 1 to 61 or Compound N of the present invention, R 1 A compound in which is a hydrogen atom, n is 1, and Q is a group represented by Q2. [Aspect 77] In any one of Aspects 1 to 61 or the present compound N, R 1 is a hydrogen atom, n is 1, and R 2 is a methyl group or a halogen atom, and Q is a group represented by Q2. [Aspect 78] In any one of Aspects 1 to 61 or Compound N of the present invention, R 1 is a hydrogen atom, n is 1, and R 2 A compound in which is a methyl group and Q is a group represented by Q2. [Aspect 79] In any one of Aspects 1 to 61 or Compound N of the present invention, R 1 is a hydrogen atom, n is 1, and R 2 A compound in which is a chlorine atom and Q is a group represented by Q2. [Aspect 80] In the compound N of the present invention, E is a C5-C6 cycloalkenyl group optionally substituted with one or more substituents selected from Group D, a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group H}, R 7 -C≡C-, R 5 -ON=C(R 4 )- or R 6 O- and R 4 is a C1-C3 alkyl group or a hydrogen atom, and R 5 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}, or R 18 -CH2- and R 6is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or R 13 R 4 NC(O)- and R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, and R 11 and R 13 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, and R 14 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from group G, and R 18 is a phenyl group or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group G}, the group G is a group consisting of a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group (the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms), a halogen atom, and a cyano group; Group H is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, OR 14 , halogen atoms, cyano groups, C(R 4 )=N-OR 11 , a phenyl group, and a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}. [Embodiment 81] Group H is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, OR 14, halogen atoms, cyano groups, C(R 4 )=N-OR 11 , a phenyl group, and a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G}.

[0018] Next, the method for producing the compound of the present invention will be described.

[0019] Manufacturing method A The compound represented by formula (A1) (hereinafter referred to as compound (A1)) can be produced by reacting a compound represented by formula (B1) (hereinafter referred to as compound (B1)) with a compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a palladium catalyst and a base. [ka] [In the formula, E 1 represents a C6-C10 aryl group or a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group A}, M 1 represents B(OH)2 or a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, and X 51 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, or a triflyloxy group, and the other symbols have the same meanings as above. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane (hereinafter referred to as ethers); halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles); water, and mixtures of two or more of these. The palladium catalyst used in the reaction includes, for example, {1,1'-bis(diphenylphosphino)ferrocene}palladium(II) dichloride. Examples of the base used in the reaction include organic bases such as triethylamine and 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); sodium fluoride and tripotassium phosphate. In the reaction, the compound (M1) is usually used in a proportion of 1 to 10 moles, the palladium catalyst is usually used in a proportion of 0.01 to 1 mole, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B1). The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, compound (A1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M1) is known or can be produced according to a known method.

[0020] Manufacturing method B Compound (A1) can be produced by reacting a compound represented by formula (B2) (hereinafter referred to as compound (B2)) with a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a palladium catalyst and a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction can be carried out in accordance with Production Method A, using compound (M2) instead of compound (B1) and compound (B2) instead of compound (M1). Compound (M2) is known or can be produced according to a known method.

[0021] Manufacturing method C The compound represented by formula (A2) (hereinafter referred to as compound (A2)) can be produced by reacting compound (B1) with a compound represented by formula (M3) (hereinafter referred to as compound (M3)) in the presence of a metal catalyst and a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, or a mixture of two or more of these. Examples of the metal catalyst used in the reaction include bis(triphenylphosphine)palladium(II) dichloride (hereinafter referred to as PdCl2(PPh3)2) and copper(I) iodide. Examples of the base used in the reaction include organic bases. In the reaction, the compound (M3) is usually used in a proportion of 1 to 10 moles, the metal catalyst is usually used in a proportion of 0.01 to 1 mole, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B1). The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, compound (A2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M3) is known or can be produced according to a known method.

[0022] Manufacturing method D The compound represented by formula (A3) (hereinafter referred to as compound (A3)) can be produced by reacting a compound represented by formula (B3) (hereinafter referred to as compound (B3)) with a compound represented by formula (M4) (hereinafter referred to as compound (M4)) or a salt thereof. [ka] (wherein the symbols have the same meanings as defined above.) Examples of salts of compound (M4) include hydrochloride and sulfate. The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols such as methanol and ethanol (hereinafter referred to as alcohols), and mixtures of two or more of these. A base may be added to the reaction, if necessary. Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrogen carbonates; sodium hydride and tripotassium phosphate. In the reaction, the compound (M4) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B3). The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (A3) can also be produced according to the method described in WO 1998 / 043949 and the like. Compound (M4) is known or can be produced according to a known method.

[0023] Manufacturing method E The compound represented by formula (A4) (hereinafter referred to as compound (A4)) can be produced by reacting compound (B3) with a compound represented by formula (M5) (hereinafter referred to as compound (M5)) or a salt thereof. [ka] (wherein the symbols have the same meanings as defined above.) Examples of salts of compound (M5) include hydrochloride and sulfate. The reaction can be carried out according to Production Method D, using compound (M5) instead of compound (M4). Compound (M5) is known or can be produced according to a known method.

[0024] Manufacturing method F Compound (A3) can be produced by reacting a compound represented by formula (B4) (hereinafter referred to as compound (B4)) with a compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride, and tripotassium phosphate. In the reaction, the compound (M6) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B4). The reaction temperature is usually within the range of −20 to 150° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M6) is known or can be produced according to a known method.

[0025] Manufacturing method H The compound represented by formula (A5) (hereinafter referred to as compound (A5)) can be produced by reacting compound (B1) with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a metal catalyst and a base. [ka] [In the formula, Z 1 is a nitrogen atom or CR 51 represents Z 2 is a nitrogen atom or CR 52 represents Z 3 is a nitrogen atom or CR 53 represents Z 4 is a nitrogen atom or CR 54 (However, Z 1 , Z 2 , Z 3 , and Z 4 (except when all are nitrogen atoms), R 51 , R 52 , R 53 and R 54 are the same or different and are each a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, a C1-C6 alkylthio group optionally substituted with one or more substituents selected from group F, OR 14 , C(O)R 11 , C(O)OR 11 , N.R. 11 R 9 , C(R 9 )=N-OR 11, a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group, a nitro group, or a hydrogen atom, and other symbols have the same meanings as above. The reaction is usually carried out in a solvent, such as ethers, hydrocarbons, amides, water, or a mixture of two or more of these. Examples of metal catalysts used in the reaction include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile)copper(I) hexafluorophosphate, and copper(I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium fluoride, and tripotassium phosphate. If necessary, a ligand and / or an alkali metal halide may be used in the reaction. Examples of the ligand include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole per mole of compound (B1). Examples of the alkali metal halide include potassium fluoride, sodium fluoride, lithium chloride, sodium chloride, etc. When an alkali metal halide is used in the reaction, the alkali metal halide is usually used in a proportion of 0.1 to 5 moles per mole of compound (B1). In the reaction, the compound (M8) is usually used in a proportion of 1 to 10 moles, the metal catalyst is usually used in a proportion of 0.01 to 2 moles, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B1). The reaction temperature is usually in the range of −20° C. to 200° C. The reaction time is usually in the range of 0.1 to 48 hours. After the reaction is complete, compound (A5) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatments such as drying and concentrating the organic layer. Compound (M8) is known or can be produced according to a known method.

[0026] Manufacturing method I The compound represented by formula (A6) (hereinafter referred to as compound (A6)) can be produced by reacting a compound represented by formula (B5) (hereinafter referred to as compound (B5)) with a compound represented by formula (M9) (hereinafter referred to as compound (M9)) in the presence of phosphines and azodiesters. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbon ethers, halogenated hydrocarbons, amides, esters, nitriles, or a mixture of two or more of these. Examples of phosphines include triphenylphosphine and trimethylphosphine. Azodiesters include, for example, diethyl azodicarboxylate, diisopropyl azodicarboxylate, and bis(2-methoxyethyl) azodicarboxylate. In the reaction, the compound (M9) is usually used in a ratio of 1 to 10 moles, the phosphine is usually used in a ratio of 1 to 10 moles, and the azodiester is usually used in a ratio of 1 to 10 moles, relative to 1 mole of the compound (B5). The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (A6) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M9) is known or can be produced according to a known method.

[0027] Manufacturing method J Compound (A6) can also be produced by reacting compound (B5) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride, and tripotassium phosphate. In the reaction, the compound (M10) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B5). The reaction temperature is usually within the range of −20 to 150° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (A6) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M10) is known or can be produced according to a known method.

[0028] Manufacturing method K The compound represented by formula (A7) (hereinafter referred to as compound (A7)) can be produced by a step (hereinafter referred to as step (K-1)) of reacting a compound represented by formula (B6) (hereinafter referred to as compound (B6)) with a compound represented by formula (M11) (hereinafter referred to as compound (M11)) in the presence of a base to obtain a compound represented by formula (B7) (hereinafter referred to as compound (B7)), and a step (hereinafter referred to as step (K-2)) of reacting compound (B7) with a compound represented by formula (M12) (hereinafter referred to as compound (M12)) in the presence of a base. [ka] [In the formula, R 55 represents a C1-C4 alkyl group, and X 52 represents an iodine atom, a methoxysulfonyloxy group, a mesyloxy group, or a tosyloxy group, and the other symbols have the same meanings as above.]

[0029] The step (K-1) is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, amides, and mixtures of two or more of these. The base used in the reaction includes, for example, sodium hydride. In the reaction, the compound (M11) is usually used in a proportion of 1 mole to 10 moles, and the base is usually used in a proportion of 0.5 moles to 5 moles, relative to 1 mole of the compound (B6). The reaction time is usually within a range of 5 minutes to 72 hours, and the reaction temperature is usually within a range of -20°C to 100°C. After the reaction is complete, the compound (B7) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and then performing post-treatment such as drying and concentrating the organic layer. The compound (B6) and the compound (M11) are commercially available compounds, or can be prepared according to known methods.

[0030] The step (K-2) is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, and sodium hydride. In the reaction, the compound (M12) is usually used in a proportion of 1 to 10 moles and the base is usually used in a proportion of 1 to 20 moles per mole of the compound (B7). The reaction temperature is usually within the range of −20 to 100° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (A7) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M12) is a commercially available compound, or can be prepared according to known methods.

[0031] Manufacturing method L The compound represented by formula (A8) (hereinafter referred to as compound (A8)) can be produced by a step (hereinafter referred to as step (L-1)) of reacting a compound represented by formula (B8) (hereinafter referred to as compound (B8)) with a compound represented by formula (M13) (hereinafter referred to as compound (M13)) in the presence of a base to obtain a compound represented by formula (B9) (hereinafter referred to as compound (B9)), and a step (hereinafter referred to as step (L-2)) of reacting compound (B9) with compound (M12) in the presence of a base. [ka] [In the formula, R 56 represents a t-butyl group or an isopentyl group, and the other symbols have the same meanings as above.

[0032] Step (L-1) is usually carried out in a solvent, such as ethers, amides, alcohols, and mixtures of two or more of these. Examples of the base used in the reaction include sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide. In the reaction, the compound (M13) is usually used in a proportion of 1 mole to 10 moles, and the base is usually used in a proportion of 1 mole to 5 moles, relative to 1 mole of the compound (B8). The reaction time is usually within a range of 5 minutes to 72 hours, and the reaction temperature is usually within a range of -20°C to 100°C. After the reaction is complete, the compound (B9) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer. The compound (B8) and the compound (M13) are commercially available compounds, or can be prepared according to known methods.

[0033] Step (L-2) can be carried out according to step (K-2) of production method K, using compound (B9) instead of compound (B7).

[0034] Manufacturing method M The compound represented by formula (A9) (hereinafter referred to as compound (A9)) can be produced by reacting compound (B1) with a compound represented by formula (M15) (hereinafter referred to as compound (M15)) in the presence of a palladium catalyst and a base. [ka] [In the formula, E 2 represents a C5-C6 cycloalkenyl group optionally substituted with one or more substituents selected from group D, and the other symbols have the same meanings as above. The reaction is usually carried out in a solvent, such as ethers, hydrocarbons, amides, water, or a mixture of two or more thereof. Examples of the palladium catalyst used in the reaction include tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate, and palladium(II) acetylacetonate. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydrogen carbonates. If necessary, a ligand and / or an alkali metal halide may be used in the reaction. Examples of the ligand include tri-tert-butylphosphine tetrafluoroborate, triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole per mole of compound (B1). Examples of alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride, and sodium chloride. When an alkali metal halide is used in the reaction, the alkali metal halide is usually used in a proportion of 0.1 to 5 moles per mole of compound (B1). In the reaction, the compound (M15) is usually used in a proportion of 1 to 10 moles, the palladium catalyst is usually used in a proportion of 0.01 to 1 mole, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of the compound (B1). The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, compound (A9) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (A9) can also be produced according to the method described in Chem. Commun., 2013, 49, 4794. Compound (M15) is known or can be produced according to a known method.

[0035] Manufacturing method N The N-oxide of the compound represented by formula (I) can be produced by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be carried out, for example, according to the method described in U.S. Patent Application Publication No. 2018 / 0009778 or WO 2016 / 121970.

[0036] Reference manufacturing method 1 The compound represented by formula (B12) (hereinafter referred to as compound (B12)) can be produced by a step (hereinafter referred to as step (1-1)) of reacting a compound represented by formula (B10) (hereinafter referred to as compound (B10)) with compound (M11) in the presence of a base to obtain a compound represented by formula (B11) (hereinafter referred to as compound (B11)), and a step (hereinafter referred to as step (1-2)) of reacting compound (B11) with compound (M12) in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.)

[0037] Step (1-1) can be carried out according to step (K-1) of production method K, using compound (B10) instead of compound (B6).

[0038] Step (1-2) can be carried out according to step (K-2) of production method K, using compound (B11) instead of compound (B7).

[0039] Reference manufacturing method 2 The compound represented by formula (B15) (hereinafter referred to as compound (B15)) can be produced by a step (hereinafter referred to as step (2-1)) of reacting a compound represented by formula (B13) (hereinafter referred to as compound (B13)) with compound (M13) in the presence of a base to obtain a compound represented by formula (B14) (hereinafter referred to as compound (B14)), and a step (hereinafter referred to as step (2-2)) of reacting compound (B14) with compound (M12) in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.)

[0040] Step (2-1) can be carried out according to step (L-1) of production method L, using compound (B13) instead of compound (B8).

[0041] Step (2-2) can be carried out according to step (K-2) of production method K, using compound (B14) instead of compound (B7).

[0042] Reference manufacturing method 3 The compound represented by formula (B16) (hereinafter referred to as compound (B16)) can be produced by reacting compound (B1) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, sulfoxides (hereinafter referred to as sulfoxides) such as dimethyl sulfoxide (hereinafter referred to as DMSO), nitriles, and mixtures of two or more of these. Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, and tripotassium phosphate. The palladium catalyst includes, for example, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. In the reaction, bis(pinacolato)diboron is usually used in a proportion of 1 to 5 moles, a base is usually used in a proportion of 1 to 5 moles, and a palladium catalyst is usually used in a proportion of 0.01 to 0.5 moles, relative to 1 mole of compound (B1). The reaction temperature is usually within the range of 0 to 150°C, and the reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (B16) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

[0043] Reference manufacturing method 4 The compound (B5) can be produced by oxidizing the compound (B16). [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, or a mixture of two or more thereof. Examples of the oxidizing agent used in the reaction include metachloroperbenzoic acid and aqueous hydrogen peroxide. When hydrogen peroxide water is used as the oxidizing agent, a base may be added as necessary. Bases include sodium hydroxide and potassium hydroxide. In the reaction, the oxidizing agent is usually used in a proportion of 1 to 5 moles per mole of compound (B16). When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 5 moles per mole of compound (B16). The reaction temperature is usually within the range of −20 to 120° C., and the reaction time is usually within the range of 0.1 to 48 hours. After the reaction is completed, compound (B5) can be isolated by adding water and a reducing agent such as sodium thiosulfate to the reaction mixture, extracting with an organic solvent, and performing post-treatment such as drying and concentrating the organic layer.

[0044] Reference manufacturing method 5 The compound represented by formula (B17) (hereinafter referred to as compound (B17)) can be produced by reacting compound (B1) with a compound represented by formula (M14) (hereinafter referred to as compound (M14)). [ka] [In the formula, R 57 represents a methyl group or an ethyl group, and the other symbols have the same meanings as above.] The reaction can be carried out, for example, according to the method described in WO 2016 / 123253.

[0045] Reference manufacturing method 6 Compound (B4) can be produced by reacting compound (B3) with hydroxylamine or a salt thereof. [ka] (wherein the symbols have the same meanings as defined above.) Examples of salts of hydroxylamine include hydrochloride and sulfate salts. The reaction can be carried out according to Production Method D, using hydroxylamine in place of compound (M4).

[0046] The compound of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as the present components) selected from the group consisting of the following groups (a), (b), (c), and (d): The above-mentioned mixed or concomitant use means that the compound of the present invention and the present ingredient are used simultaneously, separately, or with an interval between them. When the compound of the present invention and this ingredient are used simultaneously, the compound of the present invention and this ingredient may be contained in separate preparations or may be contained in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), 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, glutamatergic chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin synthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complex I, II, The group consisting of inhibitors of genotypes III and IV, voltage-gated sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients are described in the IRAC mechanism-based classification.

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

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

[0050] Group (d) is a group of repellent ingredients.

[0051] Examples of combinations of the present ingredient and the compound of the present invention are described below: For example, alanycarb + SX means a combination of alanycarb and SX. The abbreviation SX refers to any one of the compounds of the present invention selected from the compound group SX1 to SX316 described in the Examples. The present components described below are all known components and can be obtained from commercially available preparations or produced by known methods. When the present components are microorganisms, they can also be obtained from bacterial depositories. The numbers in parentheses represent CAS RNs (registered trademarks).

[0052] Combination of the present component of the above group (a) with the compound of the present invention: Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + 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, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, Bifenazate + SX, bifenthrin + SX, bioallethrin + SX, bioresmethrin + SX,Bistrifluron + 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, 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, cyromazine + SX, dazomet + SX, deltamethrin + SX Demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + 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, ethifencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, Artemisia absinthium extract + SX, Cassia nigricans extract (extract of Cassia nigricans) + SX, Clitoria ternatea extract (extract of Clitoria ternatea) + SX, Comfrey extract (extract of Symphytum officinale) + SX, Chenopodium ambrosioides extract (extracts or simulated blend of Chenopodium ambrosioides) + SX, Tansy extract (extract of Tanacetum vulgare) + SX, Stinging nettle extract (extract of Urtica dioica) + SX, Mistletoe extract (extract of Viscum album) + SX, Famphur + SX, Fenamiphos + SX, Fenazaquin + SX, Fenbutatin oxide + SX, Fenitrothion + 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, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, Flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + 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, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoprocarb + SX SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + 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, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, momfluorothrin + SX, Monocrotophos + SX, moxidectin + SX, naled + SX, neem oil + SX, nicotine + SX, nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, Chenopodium anthelminticum seed oil + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX,Phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, Pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + 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 + SX, spinetoram + SX, spinosad + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, taufluvalinate, (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, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX,Triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + 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, 4-chloro-5-[2,2-difluoro-2-(3,4,5-trifluorophenyl)ethoxy]-2-methylphenyl 2,2,2-trifluoroethyl sulfoxide (1632218-00-8) + SX, 4-fluoro-5-[2,2-difluoro-2-(3,4,5-trifluorophenyl)ethoxy]-2-methylphenyl 2,2,2-trifluoroethyl sulfoxide (1632217-98-1) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX,(3R)-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate (2249718-27-0) + SX, BT crop protein Cry1Ab (BT crop protein Cry1Ab) + SX, BT crop protein Cry1Ac (BT crop protein Cry1Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein Cry3A (BT crop protein Cry3A) + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulosis virus strain BV-0001 + SX, Anticarsia gemmatalis mNPV + SX, Autographa californica mNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella granulosis virus V22 strain (GV strain V22) + SX,Cryptophlebia leucotreta granulosis virus (GV) + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera NPV strain BV-0003 + SX, Helicoverpa zea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis nucleopolyhedrosis virus (NPV) + SX, Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrosis virus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua nucleopolyhedrosis virus (mNPV) + SX, Spodoptera littoralis mNPV + SX, Spodoptera litura NPV + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX,Bacillus firmus strain I-1582 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus sphaericus serotype strain H5a5b + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain 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 Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kursaki strain EG234 + 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 rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria 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 thoynei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, 2-chloro-N-cyclopropyl-5-{1-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-1H-pyrazol-4-yl}-N-methylpyridine-3-carboxamide (1771741-86-6) + 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, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (907187-07-9) + SX, 3-(4'-fluoro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one (1031385-91-7) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, 1,4-dimethyl-2-[2-(3-pyridinyl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, cyproflanilide + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX. ,

[0053] Combination of the present component of the above group (b) with the compound 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, blasticidin 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, chloroneb + ​​SX, chlorothalonil + SX, chlozolinate + SX,Colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, Diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemorph + SX,Dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, tea tree extract (from Melaleuca alternifolia) + SX, Japanese knotweed extract (from Reynoutria sachalinensis) + SX, lupine seedling cotyledon extract (from the cotyledons of lupine plantlets ("BLAD")) + SX, garlic extract (from Allium sativum) + SX, horsetail extract (from Equisetum arvense) + SX, Nasturtium extract (Tropaeolum majus extract) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, triphenyltin acetate (fentin acetate) + SX, triphenyltin chloride (fentin chloride) + SX, triphenyltin hydroxide (fentin hydroxide) + SX,Ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxystrobin + SX, fluindapyr + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, Fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetylaluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + 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, Isofleucine + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Oak Leaves and Bark Quercus bark + SX, mancozeb + SX, mandestrobin + SX, mandipropamid + SX, maneb + ​​SX, mefentrifluconazole + SX, mepanipyrim + SX, mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX Metrafenone + SX, metyltetraprole + SX, mineral oils + SX, myclobutanil + SX, naftifine + SX,Nuarimol + SX, octhilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + 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, pyriophenone + SX, Pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, quinoa saponins + 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, thifluzamide + 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, triticonazole + SX, validamycin + SX, valifenalate + SX, vinclozolin + SX, mustard powder + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, 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-choro-4-(2-fluorophenoxy)-2-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-choro-4-(2-fluorophenoxy)-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-[4-(1-hydrox, y-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, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one (1616664-98-2) + 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, 4-({6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]pyridin-3-yl}oxy)benzonitrile (2046300-61-0) + 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, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + 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, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens (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, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376210-00-1) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376209-13-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376210-02-3) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376209-40-2) + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376209-15-1) + SX, N'-(2-choro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2, -methoxylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + 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, クロロインコナジド(chloroinconazide) + 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-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, N-[2-(difluoromethoxy)phenyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, N-[2-(difluoromethoxy)-4-fluorophenyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX。,

[0054] Combination of the present component of the above group (c) with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + 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 Decane-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 hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexandione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, streptomycin + SX, thidiazuron + SX, Triapenthenol + SX, Tribufos + SX, Trinexapac-ethyl + SX, Uniconazole-P + SX,2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + 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. ,

[0055] Combination of the present component of the above group (d) with the compound of the present invention: Anthraquinone + SX, deet + SX, icaridin + SX.

[0056] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) of 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, and the like.

[0057] The compound of the present invention is effective against pests, such as plant pathogenic microorganisms, harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.

[0058] The compound of the present invention can control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, Phytomyxea, and bacteria. Examples of fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following: The scientific name of the plant pathogenic microorganism that causes each disease is shown in parentheses.

[0059] Rice diseases: blast (Pyricularia oryzae), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellow dwarf disease (Sclerophthora macrospora), rhizobacterial blast and panicle blight (Epicoccum nigrum), seedling damping-off (Trichoderma viride, Rhizopus oryzae); Wheat diseases: Powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), pink snow blight (Microdochium nivale, Microdochium majus), snow blight (Typhula incarnata, Typhula ishikariensis), naked smut (Ustilago tritici), smut (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), leaf spot (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), seedling damping-off (Rhizoctonia solani) caused by Rhizoctonia fungi, damping-off (Gaeumannomyces graminis), rice blast (Pyricularia graminis-tritici); Barley diseases: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), naked smut (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), Ramularia leaf spot (Ramularia collo-cygni), seedling damping-off (Rhizoctonia solani); Corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty leaf blight (Setosphaeria turcica), tropical rust (Physopella zeae), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), ear smut (Ustilago maydis), Physoderma maydis; Cotton diseases: Anthracnose (Colletotrichum gossypii), White mold (Ramularia areola), Black spot (Alternaria macrospora, Alternaria gossypii), Black root rot (Thielaviopsis basicola); Coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); Diseases of rapeseed: Sclerotinia sclerotiorum, Alternaria brassicae, Phoma lingam, light leaf spot (Pyrenopeziza brassicae); Sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); Sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Citrus diseases: black spot (Diaporthe citri), common scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger; Apple diseases: Monilinia blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: black scab (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red scab (Gymnosporangium haraeanum); Peach diseases: brown rot (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), leaf curl (Taphrina deformans); Grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola); Persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf drop (Cercospora kaki, Mycosphaerella nawae); Fig diseases: Rust (Phakopsora nishidana); Cucurbit diseases: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora capsici), seedling damping-off (Pythium sp.); Tomato diseases: ring blight (Alternaria solani), leaf mold (Cladosporium fulvum), sooty mold (Pseudocercospora fuligena), late blight (Phytophthora infestans), powdery mildew (Leveillula taurica); Eggplant diseases: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida); Diseases of leeks: rust (Puccinia allii); Soybean diseases: purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis complex (Diaporthe longicolla); Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Peanut diseases: black leaf spot (Cercospora personata), brown spot (Cercospora arachidicola), white blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Pea diseases: powdery mildew (Erysiphe pisi), root rot (Fusarium solani); Potato diseases: summer blight (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), canker (Synchytrium endobioticum); Strawberry diseases: Powdery mildew (Sphaerotheca humuli); Tea diseases: Net blight (Exobasidium reticulatum), White scab (Elsinoe leucospila), Ring spot (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis); Tobacco diseases: red star (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); Diseases of sugar beet: Cercospora beticola, leaf rot (Thanaphorus cucumeris), root rot (Thanaphorus cucumeris), black root disease (Aphanomyces cochlioides), rust (Uromyces betae); Rose diseases: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Chrysanthemum diseases: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); Onion diseases: white spotted leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotial rot (Botrytis squamosa); Diseases of various crops: Gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, Seedling damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); Radish diseases: black spot (Alternaria brassicicola); Lawngrass diseases: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red blight (Pythium aphanidermatum); Banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola); Lentil diseases: Ascochyta disease (Ascochyta lentis); Chickpea diseases: Ascochyta disease (Ascochyta rabiei); Diseases of bell pepper: anthracnose (Colletotrichum scovillei); Mango diseases: Anthracnose (Colletotrichum acutatum); Fruit tree diseases: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa); Post-harvest diseases of apples, pears, and other fruits: Mucor rot (Mucor piriformis); Seed diseases or early growth diseases caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.; Viral diseases: big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by Polymyxa species (e.g., Polymyxa betae and Polymyxa graminis); Diseases caused by bacteria: rice seedling blight (Burkholderia plantarii), cucumber spot (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), corn Goss's wilt (Clavibacter michiganensis), Pierce's disease (Xylella fastidiosa) of grapes, olives, peaches, etc., and crown gall (Agrobacterium tumefaciens) of Rosaceae plants such as apples, peaches, and cherries.

[0060] Examples of harmful arthropods, harmful nematodes, and harmful mollusks include the following:

[0061] Hemiptera: Small brown planthopper (Laodelphax striatellus), Brown planthopper (Nilaparvata lugens), White-backed planthopper (Sogatella furcifera), Corn planthopper (Peregrinus maidis), Yellow leafhopper (Javesella pellucida), Black horned planthopper (Perkinsiella saccharicida), Tagosodes orizicolus and other Delphacidae; Green rice leafhopper (Nephotettix cincticeps), Taiwanese green rice leafhopper (Nephotettix virescens), Black-striped green rice leafhopper (Nephotettix nigropictus), Lightning leafhopper (Recilia dorsalis), Tea green leafhopper (Empoasca onukii), Potato leafhopper (Empoasca Cicadellidae, such as the corn leafhopper (Dalbulus fabae), the white leafhopper (Cofana spectra), and Amrasca biguttula biguttula; Aphrophoridae, such as the European spittlebug (Philaenus spumarius); Cercopidae, such as Mahanarva posticata and Mahanarva fimbriolata;Black bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), willow aphid (Aphis spiraecola), green peach aphid (Myzus persicae), strawberry aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat collar aphid (Rhopalosiphum padi, corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari), Japanese black aphid (Tetraneura nigriabdominalis), cotton boll aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum), English grain aphid (Sitobion avenae), and other aphids (Aphididae); grapevine aphid (Daktulosphaira vitifoliae), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera Phylloxeridae, such as (Russelae);Adelgidae, such as the Japanese hemlock aphid (Adelges tsugae), the balsam woolly aphid (Adelges piceae), and the small brown aphid (Aphrastasia pectinatae); the rice black bug (Scotinophara lurida), the black paddy bug (Scotinophara coarctata), the green grass bug (Nezara antennata), the spiny spotted bug (Eysarcoris aeneus), the large spiny spotted bug (Eysarcoris lewisi), the white spotted bug (Eysarcoris ventralis), the purple spotted bug (Eysarcoris annamita), the brown marmorated stink bug (Halyomorpha halys), and the southern green stink bug (Nezara Pentatomidae (Pentatomidae) such as the brown stink bug (Euschistus heros), the red-banded stink bug (Piezodorus guildinii), the red-banded stink bug (Oebalus pugnax), and the Dichelops melacanthus; Cydnidae (Scaptocoris castanea) and the like; Alydidae (Riptortus clavatus), the spider stink bug (Leptocorisa chinensis), and the narrow-legged stink bug (Leptocorisa acuta); Coreidae (Celetus punctiger, Leptoglossus australis), and the long-legged stink bug (Cavelerius Lygaeidae, including the common long-horned bug (Togo hemipterus), the American long-horned bug (Blissus leucopterus), and others;Miridae (Miridae) such as the red-bearded green rice bug (Trigonotylus caelestialium), the red-striped rice bug (Stenotus rubrovittatus), the long-spined wheat rice bug (Stenodema calcarata), and the rusty rice bug (Lygus lineolaris); Aleyrodidae (Aleyrodidae) such as the greenhouse whitefly (Trialeurodes vaporariorum), the tobacco whitefly (Bemisia tabaci), the citrus whitefly (Dialeurodes citri), the citrus spine whitefly (Aleurocanthus spiniferus), the tea spine whitefly (Aleurocanthus camelliae), and the Japanese oak leaf whitefly (Pealius euryae); Diaspididae, such as Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, and Unaspis citri; Coccidae, such as Ceroplastes rubens; Margarodidae, such as Icerya purchasi and Icerya seychellarum;Pseudococcidae, such as the eggplant mealybug (Phenacoccus solani), the sable mealybug (Phenacoccus solenopsis), the wisteria mealybug (Planococcus kraunhiae), the mulberry mealybug (Pseudococcus comstocki), the citrus mealybug (Planococcus citri), the moth mealybug (Pseudococcus calceolariae), the long-legged mealybug (Pseudococcus longispinus), and the tuttlemey bug (Brevennia rehi); the citrus psyllid (Diaphorina citri), the citrus psyllid (Trioza erytreae), the pear psyllid (Cacopsylla pyrisuga), and the Chinese pear psyllid (Cacopsylla Psyllidae, such as the Japanese chinensis, the potato psyllid (Bactericera cockerelli), and the cacopsylla (Cacopsylla pyricola); Tingidae, such as the plane tree earworm (Corythucha ciliata), the goldenrod earworm (Corythucha marmorata), the pear earworm (Stephanitis nashi), and the azalea earworm (Stephanitis pyrioides); Cimicidae, such as the bedbug (Cimex lectularius) and the net bug (Cimex hemipterus); Cicadidae, such as the Brazilian assassin bug (Triatoma infestans), the giant assassin bug (Triatoma rubrofasciata), Triatoma dimidiata, and the Venezuelan assassin bug (Rhodonius Reduviidae, such as Triatomine bugs (e.g., Triatomine spp.), Triatomine spp., ...

[0062] Lepidoptera: Chilo suppressalis, Dark-headed stem borer, Chilo polychrysus, White stem borer, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Rice leaf borer, Cnaphalocrocis medinalis, Marasmia patnalis, Rice casino borer, Marasmia exigua, Cotton borer, Notarcha derogata, European corn borer, Ostrinia furnacalis, European corn borer, Hellula undalis, Black-spotted corn borer, Herpetogramma luctuosale, Rice stalk moth, Nymphula Crambidae, such as the Japanese corn moth (Elasmopalpus lignosellus), the Indian meal moth (Plodia interpunctella), the Japanese two-spotted moth (Euzophera batangensis), and the Japanese striped moth (Cadra cautella);Common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm (Mamestra brassicae), rice armyworm (Sesamia inferens), armyworm (Spodoptera mauritia), two-banded cutworm (Naranga aenescens), Spodoptera frugiperda, African armyworm (Spodoptera exempta), Spodoptera cosmioides, semi-tropical armyworm (Spodoptera eridania), cutworm moth (Agrotis ipsilon), silver ringworm (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean looper (Chrysodeixis includens), Trichoplusia Heliothis spp., such as the false tobacco budworm (Heliothis virescens), Helicoverpa spp., such as the cotton bollworm (Helicoverpa armigera) and the corn earworm (Helicoverpa zea), Noctuidae, such as the velvet bean caterpillar (Anticarsia gemmatalis), cotton leafworm (Alabama argillacea), and hop wine borer (Hydraecia immanis); Pieridae, such as the cabbage white butterfly (Pieris rapae);Pear fruit moth (Grapholita molesta), plum fruit moth (Grapholita dimorpha), bean fruit moth (Leguminivora glycinivorella), azuki bean pea moth (Matsumuraeses azukivora), apple smaller tortrix (Adoxophyes orana fasciata), tea smaller tortrix (Adoxophyes honmai), tea tortrix (Homona magnanima), green tea tortrix (Archips fuscocupreanus), codling moth (Cydia pomonella), sugar candy moth (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit borer (Citripestis sagittiferella), European grape wine moth (Lobesia Tortricidae (Tortricidae) such as Caloptilia theivora and Phyllonorycter ringoniella; Gracilariae (Gracillariidae) such as Caloptilia theivora and Phyllonorycter ringoniella; Carposinidae (Carposinidae) such as Carposina sasakii; Lyonetiidae (Lyonetiidae) such as Leucoptera coffeella, Lyonetia clerkella, and Lyonetia prunifoliella; Lymantriidae (Lymantria spp.) such as Lymantria dispar and Euproctis spp. such as Euproctis pseudoconspersa; Plutellidae (Plutellidae) such as Plutella xylostella;Gelechiidae (Gelechiidae) such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absoluta; Arctiidae (Arctiidae) such as Hyphantria cunea; Castniidae (Castniidae) such as Telchin licus; Cossidae (Cossus insularis); Geometridae (Geometridae) such as Ascotis selenaria; Limacodidae (Limaculidae) such as Parasa lepida; and Stathmopoda Stathmopodidae such as Acherontia masinissa; Sphingidae such as Acherontia lachesis; Sesiidae such as Nokona feralis, Synanthedon hector, and Synanthedon tenuis; Hesperiidae such as Parnara guttata; Tineidae such as Tinea translucens and Tineola bisselliella;

[0063] Thysanoptera: Thripidae, such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, and Scirtothrips perseae; Phlaeothripidae, such as Haplothrips aculeatus.

[0064] Diptera: Anthomyiidae (such as Delia platura, Delia antiqua, and Pegomya cunicularia); Ulidiidae (such as Tetanops myopaeformis); Agromyzidae (such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola); Chloropidae (such as Chlorops oryzae); Bactrocera cucurbitae (such as Bactrocera cucurbitae) and Bactrocera citri (such as Bactrocera cucurbitae). Tephritidae, such as Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, and Rhacochlaena japonica; Ephydridae, such as Hydrellia griseola, Hydrellia philippina, and Hydrellia sasakii; Drosophila suzukii, Drosophila melanogaster; Drosophilidae, such as Drosophila melanogaster; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata; Sciaridae, such as Bradysia difformis;Cecidomyiidae (Cicedomyiidae) such as Mayetiola destructor and Orseolia oryzae; Diopsidae (Diopsis macrophthalma); Glossinidae (Tsetse flies) such as Glossina palpalis and Glossina morsitans; Simuliidae (Simuliidae) such as Simulium japonicum and Simulium damnosum; Phlebotominae (Sandflies); Tipulidae (Crane flies) such as Tipula aino, Common crane fly (Tipula oleracea), and European crane fly (Tipula paludosa); Culex pipiens pallens and Culex pipiens pallens tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles Culicidae (such as Prosimulium yezoensis and Simulium ornatum); Tabanidae (such as Tabanus trigonus);Muscidae, such as the house fly (Musca domestica), the giant house fly (Muscina stabulans), the stable fly (Stomoxys calcitrans), and the horn fly (Haematobia irritans); Calliphoridae; Sarcophagidae; Chironomidae, such as the giant midge (Chironomus plumosus), the Japanese midge (Chironomus yoshimatsui), and the gray midge (Glyptotendipes tokunagai); Fannidae;

[0065] Coleoptera: Diabrotica spp., for example, the western corn rootworm (Diabrotica virgifera virgifera), the southern corn rootworm (Diabrotica undecimpunctata howardi), the northern corn rootworm (Diabrotica barberi), and the Mexican corn rootworm (Diabrotica virgifera zeae), bean leaf beetles (Cerotoma trifurcata) such as the banded cucumber beetle (Diabrotica balteata) and the cucumber beetle (Diabrotica speciosa), the spotted neck leaf beetle (Oulema melanopus), the cucumber leaf beetle (Aulacophora femoralis), the striped flea beetle (Phyllotreta striolata), the cabbage leaf beetle (Phyllotreta cruciferae), and the western black leaf beetle (Phyllotreta Chrysomelidae, such as the cabbage stem beetle (Psylliodes chrysocephala), hop beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn beetle (Chaetocnema pulicaria), sweet potato leaf beetle (Chaetocnema confinis), potato beetle (Epitrix cucumeris), rice spur beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-spotted tortoise beetle (Laccoptera quadrimaculata), and tobacco flea beetle (Epitrix hirtipennis); seed corn beetle (Stenolophus lecontei), Slender Seed Corn Beetle (Clivina impressifrons), and other ground beetles (Carabidae);Scarabaeidae beetles such as the cuprea beetle (Anomala cuprea), the rufocuprea beetle (Anomala rufocuprea), the albopilosa beetle (Anomala albopilosa), the Japanese beetle (Popillia japonica), the long-legged scarab beetle (Heptophylla picea), the European chafer (Rhizotrogus majalis), the black marmorated beetle (Tomarus gibbosus), the black scarab beetle (Holotrichia spp.), the June beetle (Phyllophaga crinita), and other Phyllophaga spp., and Diloboderus spp. such as Diloboderus abderus; Anthriibidae beetles such as the boll weevil (Araecerus coffeae); The family Aponidae includes the sweet potato weevil (Cylas formicarius); the family Bruchidae includes the Brazilian bean weevil (Zabrotes subfasciatus); the family Scolytidae includes the pine bark beetle (Tomicus piniperda) and the coffee berry borer (Hypothenemus hampei);Potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), granaria weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white grain weevil (Rhabdoscelus lineaticollis), boll weevil (Anthonomus grandis), grass band weevil (Sphenophorus venatus), southern cornbill bug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust gourd weevil (Scepticus The Aracanthus spp. (Aracanthus spp.) such as Aracanthus griseus, Scepticus uniformis, Aracanthus mourei, and the cotton root borer (Eutinobothrus brasiliensis) are included in the Curculionidae family; the Tenebrionidae (Tribolium castaneum, Tribolium confusum, Alphitobius diaperinus, and the like); the Coccinellidae (Coccinellidae) (Epilachna vigintioctopunctata, and the like); the Flat-headed Beetle (Lyctus brunneus), the Long-horned Bostrychidea (Rhizopertha dominica); Ptinidae; Cerambycidae, such as Anoplophora malasiaca, Migdolus fryanus, and Aromia bungii;Elateridae beetles such as the Okinawan wireworm beetle (Melanotus okinawensis), the brown-headed wireworm beetle (Agriotes fuscicollis), the comb beetle (Melanotus legatus), the foot-striped wireworm beetle (Anchastus spp.), the Conoderus spp., the Ctenicera spp., the Limonius spp., and the Aeolus spp.; Staphylinidae beetles such as the blue-leaf earwig beetle (Paederus fuscipes); the small-leaved earwig beetle (Anthrenus verbasci) and the white-striped earwig beetle (Dermestes Dermestidae, such as Trogoderma granarium (Trogoderma maculates) and Lasioderma serricorne (tobacco beetle), Anobiidae, such as Stegobium paniceum (Anobiidae); Laemophloeidae, such as Cryptolestes ferrugineus (Laemophloeidae); Silvanidae, such as Oryzaephilus surinamensis (Sawtooth beetle), and Nitidulidae, such as Brassicogethes aeneus (Blossom beetle);

[0066] Orthoptera: Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red locust (Nomadacris septemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two-striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged grasshopper (Camnula pellucida), Desert grasshopper (Schistocerca The grasshoppers (Acrididae) include the common locust (Oxya gregaria), yellow-winged locust (Gastrimargus musicus), sparse-throated locust (Austracris guttulosa), oriental grasshopper (Oxya yezoensis), long-winged locust (Oxya japonica), and Taiwan grasshopper (Patanga succincta); the grasshoppers (Gryllotalpidae) include the common house cricket (Gryllotalpa orientalis); the field crickets (Gryllidae) include the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and the katydids (Tettigoniidae) include the Mormon cricket (Anabrus simplex).

[0067] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata; Atta spp. such as Atta capiguara; Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Argentine ant, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole Camponotus spp. such as Camponotus noda, Pheidole megacephala, Camponotus japonicus, and Camponotus obscuripes; Pogonomyrmex spp. such as Pogonomyrmex occidentalis; Wasmania spp. such as Wasmania auropunctata; and Formicidae such as Anoplolepis gracilipes; Vespa mandarinia, Vespa simillima, Vespa analis, and Vespa Vespidae, such as the Japanese paper wasp (Polistes velutina) and the Japanese paper wasp (Polistes jokahamae); Siricidae, such as the Japanese wood wasp (Urocerus gigas); and Bethylidae.

[0068] Order Blattodea: Ectobiidae, such as the German cockroach (Blattella germanica); Blattidae, such as the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the American cockroach (Periplaneta australasiae), the brown cockroach (Periplaneta brunnea), and the Asian cockroach (Blatta orientalis); Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, and Neotermes Termites of the family Termitidae, such as the Satsuma termite (Glyptotermes satsumensis), Nakajima termite (Glyptotermes nakajimai), Katan termite (Glyptotermes fuscus), Hodotermopsis sjostedti, Koshu termite (Coptotermes guangzhouensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Formosan termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Snocapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.

[0069] Order Siphonaptera: Family Pulicidae such as human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), chicken flea (Echidnophaga gallinacea), etc.; Family Hectopsyllidae such as sand flea (Tunga penetrans); Family Ceratophyllidae such as European rat flea (Nosopsyllus fasciatus).

[0070] Psocodae: Pediculidae, such as the head louse (Pediculus humanus capitis); Pthiridae, such as the pubic louse (Pthirus pubis); Haematopinidae, such as the cow louse (Haematopinus eurysternus) and the pig louse (Haematopinus suis); Linognathidae, such as the cow louse (Linognathus vituli), the sheep trunk louse (Linognathus ovillus), and the woolly cow louse (Solenopotes capillatus); Bovicola bovis, Bovicola ovis, Bovicola breviceps, Damalinia Bovicoliidae, such as the genera Trichodectes canis and Felicola subrostratus; Menoponidae, such as the chicken louse Menopon gallinae, the chicken louse Menacanthus stramineus, and the Trinoton spp.; Trimenoponidae, such as the Cummingsia spp.; Trogiidae, such as the striped booklice Trogium pulsatorium; Liposcelis corrodens and the flat-headed booklice Liposcelis Liposcelidae or Liposcelididae, such as Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.

[0071] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

[0072] Acari: Tetranychidae, such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligonychus spp.; Aculops pelekassi, Aculops citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, and Aculus spp. Eriophyidae, such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae, such as Polyphagotarsonemus latus; Tenuipalpidae, such as Brevipalpus phoenicis; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Rocky Mountain wood tick (Dermacentor andersoni), Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Western black-legged tick (Ixodes pacificus), Ixodes holocyclus, Ixodes ricinus, Lone star tick (Amblyomma Ixodidae ticks such as Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, and Rhipicephalus decoloratus; Argasidae ticks such as Argas persicus, Ornithodoros hermsi, and Ornithodoros turicata; Acaridae ticks such as Tyrophagus putrescentiae and Tyrophagus similis; Dermatophagoides farinae and Dermatophagoides pteronyssinus. Pyroglyphidae, such as Pteronyssinus;Cheyletidae, such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, and Cheyletiella yasguri; Psoroptidae, such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, and Chorioptes spp.; Sarcoptidae, such as Notoedres cati, Notoedres muris, and Sarcoptes scabiei; Listrophorus Listrophoridae such as Dermanyssus gibbus; Dermanyssidae such as Dermanyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum and Ornithonyssus bacoti; Varroidae such as Varroa jacobsoni; Demodex canis and Demodex cati; Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium scutellaris Trombiculidae, such as scutellare;

[0073] Araneae: Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii. Polydesmida: Paradoxosomatidae, including Oxidus gracilis and Nedyopus tambanus. Isopoda: Armadillidiidae, including Armadillidium vulgare. Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus. Gastropoda: Limacidae, such as Limax marginatus and Limax flavus; Philomycidae, such as Meghimatium bilineatum; Ampullariidae, such as Pomacea canaliculata;

[0074] Nematoda: Aphelenchoididae, such as the rice root-lesion nematode (Aphelenchoides besseyi); Pratylenchidae, such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, and Radopholus similis; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, soybean cyst nematode (Heterodera glycines), and potato cyst nematode (Globodera Heteroderidae such as Globodera pallida (potato white cyst nematode) and Rotylenchulus reniformis (Hoplolaimidae) such as Nothotylenchus acris (strawberry root nematode) and Ditylenchus dipsaci (sea nematode) such as Anguinidae; Tylenchulidae such as Tylenchulus semipenetrans (citrus root nematode) such as Xiphinema index (grape nematode); Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus (pine wood nematode).

[0075] The harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes that have reduced chemical sensitivity or have developed chemical resistance to insecticides, acaricides, molluscicides, and nematodes.

[0076] The compound of the present invention or Composition A is usually mixed with an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier, and, if necessary, surfactants and other formulation adjuvants are added to formulate it into an emulsion, oil, dust, granule, wettable powder, water dispersible granule, flowable, dry flowable, microcapsule, aerosol, poison bait, resin formulation, paste formulation, foam, carbon dioxide formulation, etc. These formulations may also be processed into mosquito coils, electric mosquito mats, liquid mosquito repellent formulations, smoke formulations, fumigants, and sheet formulations for use. These formulations usually contain 0.01 to 95% by weight of the compound of the present invention or Composition A.

[0077] Examples of solid carriers used in formulation include fine powders and granules of clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, etc.).

[0078] Examples of liquid carriers include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, diesel, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, acetone, methyl methyl ketone, methyl methyl naphthalene, etc.), and the like. Examples of suitable solvents include diisobutyl dipicate, propylene glycol monomethyl ether acetate, etc., nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, 1,4-dioxane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc.), amides (DMF, N,N-dimethylacetamide, etc.), sulfoxides (DMSO, etc.), propylene carbonate, and vegetable oils (soybean oil, cottonseed oil, etc.).

[0079] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

[0080] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.

[0081] Other formulation adjuvants include adhesives, dispersants, colorants, and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol). Specifically, Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0082] Examples of the substrate for the resin preparation include vinyl chloride polymers and polyurethanes, and these substrates may contain, as needed, plasticizers such as phthalate esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, and stearic acid. Resin preparations are obtained by kneading compounds into the substrate using a conventional kneading device and then molding the mixture by injection molding, extrusion molding, press molding, or the like. If necessary, the mixture can be further processed, for example, through molding and cutting processes, into resin preparations in the form of plates, films, tapes, nets, strings, or the like. These resin preparations are processed into, for example, animal collars, animal ear tags, sheet preparations, attractants, and gardening supports. Examples of base materials for poison bait include grain flour, vegetable oil, sugar, and crystalline cellulose, and, if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, agents to prevent accidental ingestion by children and pets such as chili pepper powder, and pest-attracting flavors such as cheese flavoring, onion flavoring, and peanut oil may also be added.

[0083] In the present invention, the plant includes the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0084] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that have the ability to grow when separated from the main body and placed in soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs are a collective term for bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, or tuberous roots. Potato cultivation begins by planting the tubers in soil, and the tubers used are generally called seed potatoes.

[0085] An example of a method for controlling pests by applying an effective amount of the compound of the present invention or composition A to soil is a method in which an effective amount of the compound of the present invention or composition A is applied to soil before or after planting a plant. More specifically, for example, planting hole treatment (planting hole spraying, planting hole treatment soil incorporation), plant base treatment (plant base spraying, plant base soil incorporation, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (planting furrow spraying, planting furrow soil incorporation), row treatment (row spraying, row soil incorporation, row spraying during the growing period), row treatment at sowing (row spraying at sowing, row soil incorporation at sowing), overall treatment (overall soil spraying, overall soil incorporation), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (granular foliar spray during the growing period, spraying under the crown or around the main trunk, soil surface spraying, soil surface incorporation, seeding hole spraying, furrow surface spraying, inter-row spraying), Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding with chemicals), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding with chemicals), seedbed treatments (seedling bed spraying, seedbed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (mixing culture soil, plowing in, mixing topsoil, mixing soil where rain falls, planting position treatment, spraying granular inflorescences, mixing paste fertilizer).

[0086] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the compound of the present invention or composition A. More specifically, examples include spray treatments in which a suspension of the compound of the present invention or composition A is sprayed onto the surface of seeds or vegetative reproductive organs in mist form, smear treatments in which seeds or vegetative reproductive organs are coated with the compound of the present invention or composition A, immersion treatments in which seeds are immersed in a solution of the compound of the present invention or composition A for a certain period of time, and methods in which seeds or vegetative reproductive organs are coated with a carrier containing the compound of the present invention or composition A (film coating treatment, pellet coating treatment, etc.). The vegetative reproductive organs mentioned above particularly include seed potatoes. When applying Composition A to seeds or vegetative reproductive organs, the seeds or vegetative reproductive organs can be treated with a single formulation of Composition A, or the seeds or vegetative reproductive organs can be treated with multiple separate formulations of Composition A. Examples of methods of treating with multiple separate formulations of Composition A include a method of treating with a formulation containing only the compound of the present invention as an active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this ingredient; and a method of treating with a formulation containing the compound of the present invention and this ingredient as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this ingredient other than the ingredient that has already been treated. In the present invention, the seeds or vegetative reproductive organs carrying the compound of the present invention or composition A refer to seeds or vegetative reproductive organs in a state in which the compound of the present invention or composition A is attached to the surface of the seeds or vegetative reproductive organs. The seeds or vegetative reproductive organs carrying the compound of the present invention or composition A may have materials other than the compound of the present invention or composition A attached thereto before or after the compound of the present invention or composition A is attached to the seeds or vegetative reproductive organs. When composition A is attached to the surface of a seed or vegetative reproductive organ in the form of a layer, the layer may consist of one or more layers. When the composition consists of multiple layers, each layer may contain one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer containing no active ingredients. Seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A can be obtained, for example, by applying a formulation containing the compound of the present invention or Composition A to seeds or vegetative reproductive organs by the seed treatment method described above.

[0087] When the compound of the present invention or composition A is used for controlling pests in the agricultural field, the application rate is 10,000 m 2The amount of the compound of the present invention is usually 1 to 10,000 g per kg of seed or vegetative reproductive organ. When treating seeds or vegetative reproductive organs, the compound of the present invention is usually applied in an amount within the range of 0.001 to 100 g per kg of seed or vegetative reproductive organ. When the compound of the present invention or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate, etc., it is usually applied after being diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm, and granules, dusts, etc. are usually applied as is.

[0088] Alternatively, the resin preparation can be processed into a sheet or string shape and wrapped around the crop, stretched around the crop, or spread on the soil around the base of the plant.

[0089] When the compound of the present invention or composition A is used to control harmful arthropods living in houses, the application rate is 1 / 2 m / day for surface treatment. 2 The amount of the compound of the present invention per 1 m2 of treatment space is usually 0.01 to 1000 mg. 3 When the compound of the present invention or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate or the like, it is usually applied after diluting with water so that the active ingredient concentration is 0.1 to 10,000 ppm, whereas oil solutions, aerosols, fumigants, poison baits and the like are applied as is.

[0090] The compound of the present invention or Composition A can be used as an agent for controlling harmful organisms in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0091] Corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, Solanaceae vegetables (eggplant, tomato, bell pepper, chili pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae vegetables (radish, turnip, 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.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (horseshoe, etc.). vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, taro, pome fruits (apples, European pears, Japanese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (unshu mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, loquats, bananas, coffee, dates, coconuts, tea, mulberry, ornamental plants, forest plants, lawn grass, pasture grass.

[0092] The above plants also include genetically modified crops. [Example]

[0093] The present invention will be explained in more detail below by showing Production Examples, Reference Production Examples, Formulation Examples and Test Examples, but the present invention is not limited to these examples.

[0094] In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, Bu represents a butyl group, i-Bu represents an isobutyl group, t-Bu represents a tert-butyl group, Pen represents a pentyl group, c-Pr represents a cyclopropyl group, c-Bu represents a cyclobutyl group, c-Pen represents a cyclopentyl group, c-Hex represents a cyclohexyl group, and Ph represents a phenyl group.

[0095] First, examples of the preparation of the compounds of the present invention will be shown.

[0096] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [MH] - and retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0097] [LC conditions] Column: L-column 2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 254nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0mL / min Pump: LC-20AD (Shimadzu Corporation) 2 units (high pressure gradient) Gradient conditions: The solution is delivered at the concentration gradient shown in [Table LC1].

[0098] [Table 1]

[0099] [MS conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization method: DUIS

[0100] Reference manufacturing example 1 To a mixture of 19.4 g of methyl 2-(5-bromo-2-methylphenyl)acetate (prepared by the method described in WO 2019 / 016269), 14.7 mL of methyl formate, and 150 mL of dimethoxyethane, 19.7 g of potassium tert-butoxide was added at 0°C and stirred at room temperature for 1 hour. 1N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 100 mL of DMF was added to the resulting residue and stirred. 9.9 g of potassium carbonate and 6.8 mL of dimethyl sulfate were then added sequentially at 0°C and stirred at room temperature for 5 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 14.2 g of intermediate 1 represented by the following formula: [ka] Intermediate 1: 1 H-NMR (CDCl3) δ: 7.56 (1H, s), 7.33 (1H, dd), 7.24 (1H, d), 7.09 (1H, d), 3.84 (3H, s), 3.70 (3H, s), 2.12 (3H, s).

[0101] Reference manufacturing example 1-1 The compounds prepared according to Reference Preparation Example 1 and their physical properties are shown below. [ka] Intermediate 1-2: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.38-7.35 (2H, m), 7.29-7.26 (1H, m), 3.87 (3H, s), 3.72 (3H, s).

[0102] Reference manufacturing example 1-2 The compounds that can be produced according to Reference Production Example 1 are shown below. Formula (M1-a): [ka] In the compound represented by the formula 1 , R 22 , and R 23 A compound in which any of the combinations described in [Table A1] is present.

[0103] [Table 2]

[0104] Reference manufacturing example 1-3 The compounds prepared according to Reference Preparation Example 1 and their physical properties are shown below. In the compound represented by formula (M1-a), R 1 , R 22 , and R 23 A compound in which any of the combinations described in [Table A14] is present. [Table 3] Intermediate 1-4: 1 H-NMR (CDCl3) δ: 7.50 (1H, s), 7.37 (1H, dd), 7.28 (1H, d), 6.78 (1H, d), 3.83 (3H, s), 3.76 (3H, s), 3.69 (3H, s). Intermediate 1-8: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.51 (1H, s), 7.23-7.15 (2H, m), 3.86 (3H, s), 3.74 (3H, s), 2.38 (3H, s). Intermediate 1-10: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.27 (1H, s), 7.24 (1H, s), 7.05 (1H, s), 3.86 (3H, s), 3.74 (3H, s), 2.33 (3H, s).

[0105] Reference manufacturing example 2 A mixture of 3.3 g of intermediate 1, 4.7 g of bis(pinacolato)diboron, 0.85 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 7.4 g of potassium phosphate tripotassium, and 30 mL of dimethoxyethane was stirred at 80°C for 10 hours. The resulting mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain intermediate 2 represented by the following formula: [ka] Intermediate 2: 1 H-NMR (CDCl3) δ: 7.67 (1H, dd), 7.55 (1H, s), 7.54 (1H, d), 7.23 (1H, d), 3.80 (3H, s), 3.68 (3H, s), 2.19 (3H, s), 1.32 (12H, s).

[0106] Reference manufacturing example 3 A mixture of 5.0 g of intermediate 1, 0.61 g of bis(triphenylphosphine)palladium(II) dichloride, 7.0 mL of tributyl(1-ethoxyvinyl)tin, and 30 mL of 1,4-dioxane was stirred at 100°C for 5 hours. 1N hydrochloric acid was added to the resulting mixture, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 2:3) to obtain 3.41 g of intermediate 3 represented by the following formula: [ka] Intermediate 3: 1 H-NMR (CDCl3) δ: 7.82 (1H, dd), 7.71 (1H, d), 7.60 (1H, s), 7.31 (1H, d), 3.84 (3H, s), 3.71 (3H, s), 2.57 (3H, s), 2.24 (3H, s).

[0107] Reference manufacturing example 4 To a mixture of 1.0 g of intermediate 3, 0.28 g of hydroxylamine hydrochloride, and 12 mL of methanol, 0.64 mL of pyridine was added at 0°C and stirred at room temperature for 2.5 hours. The resulting mixture was diluted with ethyl acetate and washed successively with water and saturated brine. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with a mixed solvent of ethyl acetate and hexane (2:3) to obtain 0.91 g of intermediate 4, represented by the following formula: [ka] Intermediate 4: 1 H-NMR (CDCl3) δ: 8.78 (1H, s), 7.59 (1H, s), 7.48 (1H, dd), 7.38 (1H, d), 7.23 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 2.19 (3H, s).

[0108] Reference manufacturing example 4-1 The compounds prepared according to Reference Preparation Example 4 and their physical properties are shown below. [ka] Intermediate 4-2: 1 H-NMR (CDCl3) δ: 9.01 (1H, br s), 8.11 (1H, s), 7.59 (1H, s), 7.45 (1H, dd), 7.31 (1H, d), 7.23 (1H, d), 3.81 (3H, s), 3.70 (3H, s), 2.19 (3H, s).

[0109] Reference manufacturing example 5 To a mixture of 20.0 g of methyl 2-(5-bromo-2-methylphenyl)acetate (prepared by the method described in WO 2019 / 016269), 13.2 mL of isoamyl nitrite, and 160 mL of THF, 25.4 mL of sodium methoxide (28% methanol solution) was added and stirred at room temperature for 7 hours. 1N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 6.51 g of intermediate 5 represented by the following formula: [ka] Intermediate 5: 1 H-NMR (CDCl3) δ: 9.25 (1H, s), 7.45 (1H, dd), 7.29 (1H, d), 7.15 (1H, d), 3.87 (3H, s), 2.17 (3H, s).

[0110] Reference manufacturing example 6 To a mixture of 6.51 g of intermediate 5, 4.0 g of potassium carbonate, and 60 mL of DMF, 2.7 mL of dimethyl sulfate was added at 0°C and stirred at room temperature for 2 hours. Aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:9) to obtain 4.83 g of intermediate 6, which is represented by the following formula: [ka] Intermediate 6: 1 H-NMR (CDCl3) δ: 7.42 (1H, dd), 7.23 (1H, d), 7.12 (1H, d), 4.06 (3H, s), 3.88 (3H, s), 2.13 (3H, s).

[0111] Reference manufacturing example 7 To a mixture of 2.0 g of intermediate 6 and 20 mL of methanol, 1.2 mL of methylamine (9.8 M methanol solution) was added and stirred at room temperature overnight. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.99 g of intermediate 7 represented by the following formula: [ka] Intermediate 7: 1 H-NMR (CDCl3) δ: 7.40 (1H, dd), 7.22 (1H, d), 7.10 (1H, d), 6.78 (1H, br s), 3.97 (3H, s), 2.94 (3H, d), 2.12 (3H, s).

[0112] Reference manufacturing example 8 A mixture of 4.5 g of intermediate 2, 4.0 g of metachloroperbenzoic acid, 20 mL of acetonitrile, 20 mL of ethanol, and 20 mL of water was stirred at room temperature for 15 minutes. Aqueous sodium thiosulfate and aqueous sodium bicarbonate solutions were added to the resulting mixture, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure to obtain 4.5 g of intermediate 8, which is represented by the following formula: [ka] Intermediate 8: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.08 (1H, d), 6.71 (1H, dd), 6.60 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.09 (3H, s).

[0113] Manufacturing Example 1 Under a nitrogen atmosphere, a mixture of 0.30 g of intermediate 1, 0.04 g of PdCl2(PPh3)2, 0.29 g of 1-pentyne, 3.2 mL of tetrabutylammonium fluoride (1 mol / L THF solution), and 3 mL of THF was stirred at 80°C for 3 hours. Sodium bicarbonate water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:2) to obtain 0.22 g of the present invention compound 1-3, represented by the following formula: [ka] Compounds 1-3 of the present invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.25-7.23 (1H, m), 7.15-7.12 (2H, m), 3.82 (3H, s), 3.69 (3H, s), 2.36 (2H, t), 2.15 (3H, s), 1.65-1.58 (2H, m), 1.03 (3H, t).

[0114] Manufacturing Example 1-1 The compounds produced in accordance with Production Example 1 and their physical properties are shown below.

[0115] Formula (1a): [ka] In the compound represented by the formula 7 Compound 1-2 of the present invention, wherein is a substituent as shown below. Compound 1-2 of the present invention (R 7 :c-Pr) : 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.23-7.21 (1H, m), 7.13-7.10 (2H, m), 3.81 (3H, s), 3.68 (3H, s), 2.14 (3H, s), 1.46-1.39 (1H, m), 0.85-0.75 (4H, m).

[0116] Manufacturing Example 1-2 The compounds produced in accordance with Production Example 1 and their physical properties are shown below.

[0117] Formula (2a): [ka] In the compound represented by the formula 7 and a compound in which L is any combination described in [Table A9].

[0118] [Table 4] Compounds 1-4 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, dd), 7.14 (1H, d), 7.12 (1H, d), 4.04 (3H, s), 3.86 (3H, s), 2.15 (3H, s), 1.46-1.38 (1H, m), 0.88-0.81 (2H, m), 0.80-0.75 (2H, m). Compounds 1-5 of the present invention: 1 H-NMR (CDCl3) δ: 7.31 (1H, dd), 7.14 (1H, d), 7.12 (1H, d), 4.04 (3H, s), 3.86 (3H, s), 2.15 (3H, s), 1.29 (9H, s). Compounds 1-6 of the present invention: 1 H-NMR (CDCl3) δ: 7.28 (1H, dd), 7.13 (1H, d), 7.11 (1H, d), 6.71 (1H, br s), 3.95 (3H, s), 2.92 (3H, d), 2.15 (3H, s), 1.45-1.36 (1H, m), 0.87-0.79 (2H, m), 0.79-0.72 (2H, m). Compounds 1-7 of the present invention: 1 H-NMR (CDCl3) δ: 7.29 (1H, dd), 7.14-7.11 (2H, m), 6.72 (1H, br s), 3.95 (3H, s), 2.92 (3H, d), 2.15 (3H, s), 1.28 (9H, s).

[0119] Formula (3a): [ka] In the compound represented by the formula 1 , R 7 , R 22 , and R 23 A compound in which any of the combinations described in [Table A11] is present.

[0120] [Table 5] Compound 1-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.31-7.28 (1H, m), 7.24-7.21 (2H, m), 3.84 (3H, s), 3.69 (3H, s), 1.46-1.38 (1H, m), 0.89-0.75 (4H, m). Compounds 1-8 of the present invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.32-7.28 (1H, m), 7.25-7.22 (2H, m), 3.84 (3H, s), 3.69 (3H, s), 1.29 (9H, s). Compounds 1-9 of the present invention: 1 H-NMR (CDCl3) δ: 7.49 (1H, s), 7.31 (1H, dd), 7.19 (1H, d), 6.80 (1H, d), 3.81 (3H, s), 3.77 (3H, s), 3.67 (3H, s), 1.45-1.38 (1H, m), 0.85-0.74 (4H, m). Compounds 1-10 of the present invention: 1 H-NMR (CDCl3) δ: 7.50 (1H, s), 7.31 (1H, dd), 7.19 (1H, d), 6.80 (1H, d), 3.81 (3H, s), 3.77 (3H, s), 3.67 (3H, s), 1.29 (9H, s). Compounds 1-11 of the present invention: 1H-NMR (CDCl3) δ: 7.52 (1H, s), 7.13 (1H, s), 7.11 (1H, s), 7.01 (1H, s), 3.84 (3H, s), 3.72 (3H, s), 2.30 (3H, s), 1.47-1.39 (1H, m), 0.87-0.81 (2H, m), 0.81-0.75 (2H, m). Compounds 1-12 of the present invention: 1 H-NMR (CDCl3) δ: 7.53 (1H, s), 7.14-7.11 (2H, m), 7.01-6.98 (1H, m), 3.84 (3H, s), 3.72 (3H, s), 2.30 (3H, s), 1.29 (9H, s). Compounds 1-13 of the present invention: 1 H-NMR (CDCl3) δ: 7.52 (1H, s), 7.30 (1H, d), 7.17-7.07 (2H, m), 3.84 (3H, s), 3.72 (3H, s), 2.37 (3H, s), 1.52-1.43 (1H, m), 0.90-0.83 (2H, m), 0.82-0.75 (2H, m).

[0121] Manufacturing Example 2 Under a nitrogen atmosphere, a mixture of 0.50 g of intermediate 1, 0.43 g of 3-acetylphenylboronic acid, 0.13 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 1.12 g of tripotassium phosphate, 10 mL of dimethoxyethane, and 0.1 mL of water was stirred at 80°C for 5 hours. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:2) to obtain 0.55 g of the present invention compound 2-1 represented by the following formula. [ka] Compound 2-1 of the present invention: 1H-NMR (CDCl3) δ: 8.17 (1H, t), 7.90 (1H, dq), 7.79 (1H, dq,), 7.62 (1H, s), 7.53-7.48 (2H, m), 7.38 (1H, d), 7.33 (1H, d), 3.85 (3H, s), 3.73 (3H, s), 2.65 (3H, s), 2.24 (3H, s).

[0122] Manufacturing Example 2-1 The compounds produced according to Production Example 2 and their physical properties are shown below.

[0123] Formula (1b): [ka] In the compound represented by the formula 1 , R 24 , R 25 , R 26 , R 27 , and R 28 A compound in which any of the combinations listed in [Table A2] is present.

[0124] [Table 6] Compound 2-2 of the present invention: 1 H-NMR (CDCl3) δ: 7.70-7.64 (4H, m), 7.62 (1H, s), 7.47 (1H), 7.36-7.32 (2H, m), 3.85 (3H, s), 3.73 (3H, s), 2.24 (3H, s). Compound 2-3 of the present invention: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.60-7.56 (2H, m), 7.47-7.39 (3H, m), 7.35-7.29 (3H, m), 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s). Compound 2-4 of the present invention: 1H-NMR (CDCl3) δ: 7.60 (1H, s), 7.41 (1H, dt), 7.33-7.29 (2H, m), 7.17-7.13 (1H, m), 7.10-7.04 (1H, m), 7.00-6.92 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.23 (3H, s). This compound 2-5: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.41 (1H, dd), 7.32-7.30 (2H, m), 7.12-7.08 (2H, m), 6.79-6.72 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.22 (3H, s). This compound 2-6: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.36 (1H, dd), 7.32-7.30 (1H, m), 7.26-7.25 (1H, m), 7.18 (2H, dd), 3.86 (3H, s), 3.73 (3H, s), 2.23 (3H, s). This compound 2-7: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.47-7.42 (2H, m), 7.31-7.25 (3H, m), 7.20-7.10 (2H, m), 3.84 (3H, s), 3.72 (3H, s), 2.23 (3H, s). This compound 2-8: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.44 (1H, dd), 7.37-7.29 (5H, m), 7.02-6.97 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.22 (3H, s). This compound 2-9: 1H-NMR (CDCl3) δ: 7.60 (1H, s), 7.53-7.49 (2H, m), 7.41 (1H, dd), 7.30 (1H, d), 7.28-7.26 (1H, m), 6.97-6.93 (2H, m), 3.84 (3H, s), 3.83 (3H, s), 3.72 (3H, s), 2.21 (3H, s). This compound 2-10: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.35-7.30 (2H, m), 7.27-7.19 (2H, m), 6.99-6.91 (2H, m), 3.82 (3H, s), 3.71 (3H, s), 2.23 (3H, s). Compound 2-11 of this invention: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.54-7.51 (2H, m), 7.40 (1H, dd), 7.29-7.27 (2H, m), 7.11-7.06 (2H, m), 3.83 (3H, s), 3.71 (3H, s), 2.21 (3H, s). This compound 2-12: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.51-7.48 (2H, m), 7.42-7.27 (5H, m), 3.81 (3H, s), 3.71 (3H, s), 2.21 (3H, s). This compound 2-13: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.49-7.43 (3H, m), 7.33-7.21 (4H, m), 3.83 (3H, s), 3.71 (3H, s), 2.38 (3H, s), 2.21 (3H, s). This compound 2-14: 1H-NMR (CDCl3) δ: 7.82 (1H, s), 7.76 (1H, d), 7.62 (1H, s), 7.57-7.50 (2H, m), 7.46 (1H, dd), 7.35-7.32 (2H, m), 3.85 (3H, s), 3.73 (3H, s), 2.24 (3H, s). This compound 2-15: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.56 (1H, t), 7.47-7.42 (2H, m), 7.35-7.26 (4H, m), 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s). This compound 2-16: 1 H-NMR (CDCl3) δ: 7.72 (1H, d), 7.61 (1H, s), 7.57-7.53 (1H, m), 7.43 (1H, d), 7.34-7.30 (2H, m), 7.23-7.21 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.24 (3H, s). This compound 2-17: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.44-7.39 (2H, m), 7.31-7.28 (2H, m), 7.25-7.21 (1H, m), 7.09-7.04 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.23 (3H, s). This compound 2-18: 1 H-NMR (CDCl3) δ: 7.86 (1H, t), 7.81 (1H, dq), 7.62 (1H, s), 7.59 (1H, dt), 7.51 (1H, t), 7.43 (1H, dd), 7.34-7.32 (2H, m), 3.86 (3H, s), 3.73 (3H, s), 2.24 (3H, s). This compound 2-19: 1H-NMR (CDCl3) δ: 7.83 (1H, t), 7.61 (1H, s), 7.60-7.55 (2H, m), 7.47 (1H, dd), 7.40 (1H, t), 7.35 (1H, d), 7.30 (1H, d), 4.01 (3H, s), 3.83 (3H, s), 3.72 (3H, s), 2.26 (3H, s), 2.23 (3H, s). This compound 2-20: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.58-7.55 (2H, m), 7.48-7.32 (6H, m), 3.86 (3H, s), 3.73 (3H, s). This compound 2-21: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.50-7.41 (4H, m), 7.34-7.29 (1H, m), 7.22-7.12 (2H, m), 3.87 (3H, s), 3.73 (3H, s). This compound 2-22: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.42 (1H, dt), 7.32-7.30 (2H, m), 7.22-7.18 (1H, m), 7.12-7.08 (2H, m), 3.85 (3H, s), 3.72 (3H, s), 2.23 (3H, s). This compound 2-23: 1 H-NMR (CDCl3) δ: 7.58 (1H, s), 7.29-7.28 (2H, m), 7.24-7.19 (2H, m), 6.79-6.74 (2H, m), 3.83 (3H, s), 3.77 (3H, s), 3.71 (3H, s), 2.22 (3H, s). This compound 2-24: 1H-NMR (CDCl3) δ: 7.59 (1H, s), 7.34-7.28 (2H, m), 7.25-7.20 (2H, m), 7.15-7.14 (1H, m), 7.08-7.03 (1H, m), 3.84 (3H, s), 3.71 (3H, s), 2.25 (3H, s).

[0125] Equation (1c):

change

[0126] Table 7 This compound 3-1: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.46 (1H, dd), 7.35 (1H, d,), 7.25-7.22 (3H, m), 7.05 (1H, dd), 3.84 (3H, s), 3.71 (3H, s), 2.19 (3​​H, s). This compound 3-2: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.39 (1H, dd), 7.29 (1H, d), 7.20 (1H, d), 7.04 (1H, d), 6.70-6.68 (1H, m), 3.83 (3H, s), 3.71 (3H, s), 2.49 (3H, d), 2.17 (3H, s). Compound 3-3 of this invention: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.35 (1H, dd), 7.25-7.21 (2H, m), 7.01 (1H, d), 6.85 (1H, d), 3.84 (3H, s), 3.71 (3H, s), 2.18 (3H, s). This compound 3-4: 1H-NMR (CDCl3) δ: 7.60 (1H, s), 7.45 (1H, dd), 7.40-7.39 (1H, m), 7.37-7.34 (3H, m), 7.26-7.24 (1H, m), 3.84 (3H, s), 3.71 (3H, s), 2.20 (3H, s). Compounds 3-5 of the present invention: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.44 (1H, dd), 7.33 (1H, d), 7.29 (1H, d), 7.11 (1H, d), 7.05 (1H, d), 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s). Compounds 3-6 of the present invention: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.52 (1H, dd), 7.43-7.42 (2H, m), 7.26-7.23 (1H, m), 6.58 (1H, d), 6.44 (1H, dd), 3.83 (3H, s), 3.71 (3H, s), 2.19 (3H, s). Compounds 3-7 of the present invention: 1 H-NMR (CDCl3) δ: 7.69-7.68 (1H, m), 7.59 (1H, s), 7.45-7.44 (1H, m), 7.34 (1H, dd), 7.24-7.22 (2H, m), 6.68-6.67 (1H, m), 3.83 (3H, s), 3.71 (3H, s), 2.19 (3H, s).

[0127] Manufacturing Example 2-2 The compounds that can be produced according to Production Example 2 are shown below. In the compound represented by formula (1b), R 1 , R 24 , R 25 , R 26 , R 27 , and R 28 A compound in which any of the combinations described in [Table A10] is present. [Table 8]

[0128] Manufacturing Example 2-3 The compounds produced according to Production Example 2 and their physical properties are shown below.

[0129] In the compound represented by formula (1b), R 1 , R 24 , R 25 , R 26 , R 27 , and R 28 A compound in which any of the combinations described in [Table A12] is present.

[0130] [Table 9] Compound 2-25 of the present invention: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.33 (2H, s), 7.24 (1H, s), 7.12-7.04 (1H, m), 6.92-6.86 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.24 (3H, s). Compound 2-26 of the present invention: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.36-7.33 (2H, m), 7.24 (1H, s), 7.07-6.98 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.25 (3H, s). Compound 2-27 of the present invention: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.40 (1H, d), 7.33-7.25 (2H, m), 6.97-6.84 (2H, m), 3.85 (3H, s), 3.72 (3H, s), 2.24 (3H, s). Compound 2-32 of the present invention: 1H-NMR (CDCl3) δ: 7.61 (1H, s), 7.41-7.34 (2H, m), 7.31-7.26 (3H, m), 7.22-7.15 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.22 (3H, s). This compound 2-33: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.44-7.36 (2H, m), 7.31-7.26 (2H, m), 6.94-6.85 (2H, m), 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s). This compound 2-34: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.41-7.30 (2H, m), 7.26-7.24 (1H, m), 7.18-7.12 (1H, m), 7.03-6.96 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.23 (3H, s). This compound 2-35: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.36-7.27 (2H, m), 7.20 (1H, s), 3.85 (3H, s), 3.72 (3H, s), 2.25 (3H, s). This compound 2-36: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.55-7.38 (5H, m), 7.14-7.08 (2H, m), 3.87 (3H, s), 3.74 (3H, s). This compound 2-37: 1 H-NMR (CDCl3) δ: 7.62 (1H, s), 7.55 (1H, t), 7.51-7.41 (4H, m), 7.38-7.30 (2H, m), 3.87 (3H, s), 3.74 (3H, s). This compound 2-38: 1H-NMR (CDCl3) δ: 7.62 (1H, s), 7.50-7.33 (5H, m), 7.29-7.24 (1H, m), 7.07-7.01 (1H, m), 3.87 (3H, s), 3.74 (3H, s). Compound 2-39 of the present invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.53-7.44 (3H, m), 7.36 (1H, d), 7.09 (2H, t), 6.98 (1H, d), 3.83 (3H, s), 3.83 (3H, s), 3.72 (3H, s). Compound 2-40 of the present invention: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.54-7.50 (1H, m), 7.44 (1H, td), 7.39 (1H, t), 7.30-7.24 (1H, m), 7.17 (1H, td), 7.12 (1H, m), 6.99 (1H, d), 3.84 (3H, s), 3.83 (3H, s), 3.72 (3H, s). Compound 2-43 of the present invention: 1 H-NMR (CDCl3) δ: 7.61 (1H, s), 7.45 (1H, dd), 7.34-7.28 (3H, m), 7.18 (1H, dt), 7.12 (1H, t), 6.86 (1H, dd), 3.85 (3H, s), 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s).

[0131] Formula (2b): [ka] In the compound represented by the formula 24 , R 25 , R 26 , R 27 , and R 28 A compound in which any of the combinations described in [Table A13] is present.

[0132] [Table 10] Compound 2-41 of the present invention: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.56-7.50 (2H, m), 7.28 (2H, d), 7.14-7.07 (3H, m), 3.87 (3H, s), 3.75 (3H, s), 2.42 (3H, s). Compound 2-42 of the present invention: 1 H-NMR (CDCl3) δ: 7.58 (1H, s), 7.44 (1H, td), 7.33-7.27 (3H, m), 7.21-7.10 (3H, m), 3.86 (3H, s), 3.75 (3H, s), 2.42 (3H, s).

[0133] Manufacturing Example 3 Under a nitrogen atmosphere, a mixture of 0.30 g of intermediate 2, 0.21 g of 2-bromopyridine, 0.07 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 0.27 g of tripotassium phosphate, 6 mL of dimethoxyethane, and 0.1 mL of water was stirred at 80°C for 5 hours. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to obtain 0.15 g of the present invention compound 4-1 represented by the following formula. [ka] Compound 4-1 of the present invention: 1 H-NMR (CDCl3) δ: 8.66 (1H, td), 7.85 (1H, dd), 7.76 (1H, d), 7.72-7.70 (2H, m), 7.60 (1H, s), 7.33 (1H, d), 7.20-7.16 (1H, m), 3.83 (3H, s), 3.70 (3H, s), 2.23 (3H, s).

[0134] Manufacturing Example 3-1 The compounds produced according to Production Example 3 and their physical properties are shown below.

[0135] Formula (1d): [ka] In the compound represented by the formula 29 , R 30 , R 31 , and R 32 A compound in which any of the combinations described in [Table A4] is present. [Table 11] Compound 4-2 of the present invention: 1 H-NMR (CDCl3) δ: 7.84 (1H, dd), 7.73 (1H, d), 7.61-7.57 (2H, m), 7.49 (1H, d), 7.31 (1H, d), 7.04 (1H, d), 3.82 (3H, s), 3.70 (3H, s), 2.60 (3H, s), 2.22 (3H, s). Compound 4-3 of the present invention: 1 H-NMR (CDCl3) δ: 7.86 (1H, dd), 7.83-7.77 (2H, m), 7.61-7.59 (2H, m), 7.32 (1H, d), 6.81 (1H, dd), 3.83 (3H, s), 3.71 (3H, s), 2.23 (3H, s). Compound 4-4 of the present invention: 1 H-NMR (CDCl3) δ: 7.94 (1H, dd), 7.90-7.84 (2H, m), 7.80 (1H, d), 7.62 (1H, s), 7.55 (1H, dd), 7.35 (1H, d), 3.84 (3H, s), 3.71 (3H, s), 2.24 (3H, s). Compound 4-5 of the present invention: 1 H-NMR (CDCl3) δ: 8.51 (1H, d), 7.80 (1H, dd), 7.71-7.68 (2H, m), 7.60 (1H, s), 7.45-7.40 (1H, m), 7.32 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.23 (3H, s). Compounds 4-6 of the present invention:1 H-NMR (CDCl3) δ: 8.48 (1H, td), 7.86 (1H, dt), 7.77 (1H, t), 7.60 (1H, s), 7.43 (1H, ddd), 7.33 (1H, d), 7.22-7.18 (1H, m), 3.81 (3H, s), 3.69 (3H, s), 2.24 (3H, s). This compound 4-7: 1 H-NMR (CDCl3) δ: 8.91 (1H, dd), 7.94-7.89 (2H, m), 7.83-7.80 (2H, m), 7.62 (1H, s), 7.36 (1H, d), 3.83 (3H, s), 3.71 (3H, s), 2.25 (3H, s). This compound 4-8: 1 H-NMR (CDCl3) δ: 7.92 (1H, dd), 7.76 (1H, d), 7.61-7.57 (2H, m), 7.31 (2H, dd), 6.64 (1H, dd), 4.02 (3H, s), 3.83 (3H, s), 3.71 (3H, s), 2.23 (3H, s).

[0136] Formula (1c) shows the される compound において and Eが[Table A5] and the のsubstituent group である compound.

[0137] Table 12

[0138] Table 13 This compound 5-1: 1 H-NMR (CDCl3) δ: 8.77 (2H, d), 8.31 (1H, d), 8.20 (1H, s), 7.61 (1H, s), 7.35 (1H, d), 7.15-7.11 (1H, m), 3.82 (3H, s), 3.70 (3H, s), 2.25 (3H, s). This compound 5-2:1 H-NMR (CDCl3) δ: 8.61 (1H, d), 8.31 (1H, dd), 8.19 (1H, d), 7.60 (1H, s), 7.33 (1H, d), 7.00 (1H, d), 3.82 (3H, s), 3.69 (3H, s), 2.56 (3H, s), 2.24 (3H, s). This compound 5-3: 1 H-NMR (CDCl3) δ: 8.99 (1H, d), 8.37 (1H, dd), 8.25 (1H, d), 7.63 (1H, d), 7.45 (1H, d), 7.37 (1H, t), 3.84 (3H, s), 3.71 (3H, s), 2.26 (3H, s). This compound 5-4: 1 H-NMR (CDCl3) δ: 9.01 (1H, d), 8.60 (1H, dd), 8.46 (1H, d), 7.89 (1H, dd), 7.79 (1H, d), 7.62 (1H, s), 7.37 (1H, d), 3.85 (3H, s), 3.72 (3H, s), 2.25 (3H, s). Compound 5-5 of this invention: 1 H-NMR (CDCl3) δ: 8.79 (1H, d), 7.91 (1H, dd), 7.81 (1H, d), 7.61 (1H, s), 7.34 (1H, d), 7.11 (1H, d), 4.07 (2H, s), 3.84 (3H, s), 3.71 (3H, s), 2.24 (3H, s), 1.05 (9H, s). This compound 5-6: 1 H-NMR (CDCl3) δ: 8.80 (1H, d), 7.95 (1H, dd), 7.85 (1H, d), 7.63-7.31 (7H, m), 3.85 (3H, s), 3.72 (3H, s), 2.27 (3H, s). This compound 5-7: 1H-NMR (CDCl3) δ: 8.79 (1H, s), 7.94 (1H, dd), 7.89-7.85 (2H, m), 7.62 (1H, s), 7.52-7.45 (2H, m), 7.41-7.34 (3H, m), 3.85 (3H, s), 3.71 (3H, s), 2.26 (3H, s). This compound 5-8: 1 H-NMR (CDCl3) δ: 7.84 (1H, d), 7.75 (1H, s), 7.63 (1H, s), 7.38 (1H, d), 3.86 (3H, s), 3.72 (3H, s), 2.27 (3H, s). This compound 5-9: 1 H-NMR (CDCl3) δ: 7.78 (1H, dd), 7.70 (1H, d), 7.61 (1H, s), 7.34 (1H, d), 3.85 (3H, s), 3.71 (3H, s), 2.71 (3H, s), 2.24 (3H, s). This compound 5-10: 1 H-NMR (CDCl3) δ: 7.80 (1H, dd), 7.69 (1H, d), 7.62 (1H, s), 7.32 (1H, d), 3.85 (3H, s), 3.72 (3H, s), 2.24 (3H, s), 1.48 (9H, s). This compound 5-11: 1 H-NMR (CDCl3) δ: 8.39-8.37 (2H, m), 7.89 (1H, dd), 7.80 (1H, d), 7.64 (1H, s), 7.52-7.47 (3H, m), 7.37 (1H, d), 3.86 (3H, s), 3.73 (3H, s), 2.26 (3H, s). This compound 5-12: 1 H-NMR (CDCl3) δ: 7.93-7.86 (3H, m), 7.79 (1H, d), 7.65 (1H, s), 7.38 (1H, d), 6.92 (1H, tt), 3.87 (3H, s), 3.74 (3H, s), 2.27 (3H, s). This compound 5-13: 1 H-NMR (CDCl3) δ: 7.67 (1H, dd), 7.58 (1H, s), 7.54 (1H, d), 7.49 (1H, d), 7.22 (1H, d), 6.46 (1H, d), 3.81 (3H, s), 3.69 (3H, s), 2.18 (3H, s), 1.61 (9H, s). This compound 5-14: 1 H-NMR (CDCl3) δ: 7.64 (1H, dd), 7.57 (1H, s), 7.54 (1H, d), 7.36 (1H, d), 7.25-7.22 (1H, m), 6.49 (1H, d), 4.10 (2H, t), 3.81 (3H, s), 3.69 (3H, s), 2.19 (3H, s), 1.96-1.87 (2H, m), 0.93 (3H, t). This compound 5-15: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.53 (1H, d), 7.32-7.27 (1H, m), 7.24 (1H, dd), 7.15 (1H, d), 6.27 (1H, d), 4.00 (2H, d), 3.85 (3H, s), 3.72 (3H, s), 2.23 (3H, s), 1.24-1.18 (1H, m), 0.50-0.45 (2H, m), 0.22-0.18 (2H, m). This compound 5-16: 1 H-NMR (CDCl3) δ: 8.84 (1H, dd), 8.55 (1H, dd), 7.88-7.85 (1H, m), 7.62 (1H, s), 7.45 (1H, dd), 7.35-7.31 (3H, m), 3.85 (3H, s), 3.73 (3H, s), 2.24 (3H, s). This compound 5-17: 1H-NMR (CDCl3) δ: 9.12 (1H, dd), 7.96 (1H, dd), 7.87-7.83 (2H, m), 7.62 (1H, s), 7.49 (1H, dd), 7.39 (1H, d), 3.84 (3H, s), 3.71 (3H, s), 2.26 (3H, s). This compound 5-18: 1 H-NMR (CDCl3) δ: 7.60 (1H, s), 7.52 (1H, d), 7.30 (1H, d), 7.23 (1H, dd), 7.14 (1H, d), 6.25 (1H, d), 4.10-4.06 (2H, m), 3.85 (3H, s), 3.72 (3H, s), 2.24 (3H, s), 1.89-1.80 (2H, m), 0.84 (3H, t). This compound 5-19: 1 H-NMR (CDCl3) δ: 7.64 (1H, dd), 7.58 (1H, s), 7.55-7.54 (1H, m), 7.50 (1H, d), 7.24 (1H, d), 6.51 (1H, d), 4.02 (2H, d), 3.81 (3H, s), 3.69 (3H, s), 2.19 (3H, s), 1.35-1.30 (1H, m), 0.67-0.62 (2H, m), 0.40-0.36 (2H, m). This compound 5-20: 1 H-NMR (CDCl3) δ: 7.89 (1H, dd), 7.77 (1H, d), 7.61 (1H, s), 7.35 (1H, d), 3.85 (3H, s), 3.71 (3H, s), 2.24 (3H, s), 1.47 (9H, s).

[0139] Manufacturing example 4 A mixture of 0.30 g of intermediate 1, 0.1 mL of pyrazole, 0.20 g of copper(I) iodide, 0.29 g of potassium carbonate, 0.17 mL of trans-N,N-dimethylcyclohexane-1,2-diamine, and 10 mL of DMF was stirred at 120°C for 5 hours under a nitrogen atmosphere. The resulting mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 0.20 g of the present invention compound 6-1 represented by the following formula. [ka] Compound 6-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.89 (1H, d), 7.69 (1H, d), 7.60 (1H, s), 7.53 (1H, dd), 7.45 (1H, d), 7.29 (1H, d), 6.43 (1H, t), 3.84 (3H, s), 3.71 (3H, s), 2.20 (3H, s).

[0140] Manufacturing Example 4-1 The compounds produced according to Production Example 4 and their physical properties are shown below.

[0141] Formula (1f): [ka] In the compound represented by the formula 33 is a substituent listed in [Table A6]. [Table 14] Compound 6-2 of the present invention: 1 H-NMR (CDCl3) δ: 7.74 (1H, d), 7.58 (1H, s), 7.48 (1H, dd), 7.40 (1H, d), 7.24 (1H, s), 6.05 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 2.05-2.00 (1H, m), 0.98-0.93 (2H, m), 0.80-0.76 (2H, m). This compound 6-3: 1 H-NMR (CDCl3) δ: 7.74 (1H, d), 7.59 (1H, s), 7.51 (1H, dd), 7.39 (1H, d), 7.26-7.24 (1H, m), 6.27 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 1.36 (9H, s). Compound 6-4 of this invention: 1 H-NMR (CDCl3) δ: 7.77 (1H, d), 7.58 (1H, s), 7.48 (1H, dd), 7.41 (1H, d), 7.27-7.25 (1H, m), 6.21 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.37 (3H, s), 2.19 (3H, s). Compound 6-5 of this invention: 1 H-NMR (CDCl3) δ: 7.90 (1H, d), 7.60 (1H, s), 7.54 (1H, dd), 7.45 (1H, d), 7.32 (1H, d), 6.68 (1H, d), 3.85 (3H, s), 3.71 (3H, s), 2.22 (3H, s). This compound 6-6: 1 H-NMR (CDCl3) δ: 7.92-7.89 (3H, m), 7.62-7.60 (2H, m), 7.52 (1H, d), 7.44-7.37 (2H, m), 7.34-7.29 (2H, m), 6.74 (1H, d), 3.85 (3H, s), 3.72 (3H, s), 2.21 (3H, s). This compound 6-7: 1 H-NMR (CDCl3) δ: 7.91 (1H, d), 7.84 (2H, dt), 7.61 (1H, s), 7.59 (1H, dd), 7.51 (1H, d), 7.38 (2H, dt), 7.31 (1H, d), 6.71 (1H, d), 3.85 (3H, s), 3.72 (3H, s), 2.21 (3H, s). Compounds 6-8 of the present invention: 1 H-NMR (CDCl3) δ: 7.94 (1H, d), 7.90-7.84 (1H, m), 7.61 (1H, s), 7.59 (1H, dd), 7.50 (1H, d), 7.31 (1H, d), 7.06-6.99 (1H, m), 6.85 (1H, dd), 3.85 (3H, s), 3.72 (3H, s), 2.22 (3H, s).

[0142] Manufacturing Example 5 To a mixture of 0.95 g of 1-(4-chlorophenyl)-1H-pyrazol-3-ol and 10 mL of chloroform, 0.88 mL of trifluoroacetic anhydride and 0.74 mL of triethylamine were added sequentially at 0°C, followed by stirring at room temperature for 1 hour. Water was added to the resulting mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Under a nitrogen atmosphere, 0.8 g of Intermediate 2, 0.18 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 1.53 g of tripotassium phosphate, and 10 mL of dimethoxyethane were added sequentially to the resulting residue, followed by stirring at 80°C for 9 hours. Ethyl acetate was added to the resulting mixture, followed by washing sequentially with water and saturated brine. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.12 g of the present compound 7-1 represented by the following formula. [ka] Compound 7-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.82 (1H, d), 7.71 (1H, dd), 7.66-7.64 (3H, m), 7.59 (1H, s), 7.38-7.35 (2H, m), 7.27 (1H, d), 6.69 (1H, d), 3.78 (3H, s), 3.69 (3H, s), 2.21 (3H, s).

[0143] Manufacturing Example 6 To a mixture of 0.25 g of Intermediate 3, 0.16 g of O-benzylhydroxylamine hydrochloride, and 3 mL of methanol was added 0.16 mL of pyridine at 0°C and stirred at room temperature for 4 hours. The resulting mixture was diluted with ethyl acetate and washed successively with water and saturated brine. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.35 g of the present compound 8-1 represented by the following formula: [ka] Compound 8-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.52 (1H, dd), 7.38 (6H, m), 7.20 (1H, d), 5.22 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.24 (3H, s), 2.18 (3H, s).

[0144] Manufacturing Example 6-1 The compounds prepared according to Preparation Example 6 and their physical properties are shown below. Formula (1h): [ka] In the compound represented by the formula 4 and R 5 A compound in which any of the combinations described in [Table A7] is present.

[0145] [Table 15] Compound 8-2 of the present invention: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.51 (1H, dd), 7.39 (1H, d), 7.21 (1H, d), 3.99 (2H, d), 3.82 (3H, d), 3.70 (3H, d), 2.23 (3H, s), 2.18 (3H, s), 1.24-1.17 (1H, m), 0.57-0.53 (2H, m), 0.32-0.30 (2H, m). This compound 8-3: 1 H-NMR (CDCl3) δ: 7.58 (1H, s), 7.53 (1H, dd), 7.39 (1H, d), 7.22 (1H, d), 4.78 (2H, d), 3.82 (3H, s), 3.70 (3H, s), 2.47 (1H, t), 2.23 (3H, s), 2.18 (3H, s). This compound 8-4: 1 H-NMR (CDCl3) δ: 8.10 (1H, s), 7.57 (1H, s), 7.47-7.29 (7H, m), 7.22 (1H, d), 5.19 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.18 (3H, s). Compound 8-5 of this invention: 1 H-NMR (CDCl3) δ: 8.07 (1H, s), 7.57 (1H, s), 7.45 (1H, dd), 7.30 (1H, d), 7.22 (1H, d), 3.97 (2H, d), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 1.23-1.16 (1H, m), 0.60-0.54 (2H, m), 0.34-0.29 (2H, m). Compound 8-6 of this invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.53 (1H, dd), 7.38 (1H, d), 7.20 (1H, d), 4.46-4.40 (1H, m), 3.82 (3H, s), 3.70 (3H, s), 2.19 (3H, s), 2.18 (3H, s), 1.29 (6H, d). This compound 8-7: 1 H-NMR (CDCl3) δ: 8.01 (1H, s), 7.57 (1H, s), 7.45 (1H, dd), 7.30 (1H, d), 7.22 (1H, d), 4.46-4.40 (1H, m), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 1.28 (6H, d). Compound 8-8 of this invention: 1 H-NMR (CDCl3) δ: 8.02 (1H, s), 7.57 (1H, s), 7.44 (1H, dd), 7.31 (1H, d), 7.23 (1H, d), 3.95 (3H, s), 3.83 (3H, s), 3.70 (3H, s), 2.19 (3H, s). This compound 8-9: 1 H-NMR (CDCl3) δ: 8.03 (1H, s), 7.57 (1H, s), 7.45 (1H, d), 7.31 (1H, s), 7.22 (1H, d), 4.20 (2H, q), 3.83 (3H, s), 3.70 (3H, s), 2.19 (3H, s), 1.31 (3H, t). Compounds 8-10 of this invention: 1 H-NMR (CDCl3) δ: 8.04 (1H, s), 7.57 (1H, s), 7.45 (1H, dd), 7.31 (1H, d), 7.22 (1H, d), 4.10 (2H, t), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 1.72 (2H, td), 0.97 (3H, t). Compounds 8-11 of this invention: 1H-NMR (CDCl3) δ: 8.03 (1H, s), 7.57 (1H, s), 7.45 (1H, dd), 7.30 (1H, d), 7.22 (1H, d), 4.14 (2H, t), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 1.76-1.64 (2H, m), 1.43-1.31 (4H, m), 0.96-0.86 (3H, m). This compound 8-12: 1 H-NMR (CDCl3) δ: 8.05 (1H, s), 7.57 (1H, s), 7.45 (1H, dd), 7.30 (1H, d), 7.22 (1H, d), 3.91 (2H, d), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 2.09-1.98 (1H, m), 0.95 (6H, d). This compound 8-13: 1 H-NMR (CDCl3) δ: 8.10 (1H, s), 7.58 (1H, s), 7.46 (1H, dd), 7.30 (1H, d), 7.25 (1H, d), 4.64-4.55 (2H, m), 3.84 (3H, s), 3.71 (3H, s), 2.20 (3H, s). This compound 8-14: 1 H-NMR (CDCl3) δ: 8.12 (1H, s), 7.58 (1H, s), 7.46 (1H, dd), 7.30 (1H, d), 7.24 (1H, d), 4.50 (2H, q), 3.84 (3H, s), 3.70 (3H, s), 2.20 (3H, s). This compound 8-15: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.50 (1H, dd), 7.39 (1H, d), 7.21 (1H, d), 3.97 (3H, s), 3.82 (3H, s), 3.69 (3H, s), 2.19 (3H, s), 2.18 (3H, s). This compound 8-16: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.51 (1H, dd), 7.39 (1H, d), 7.21 (1H, d), 4.22 (2H, q), 3.82 (3H, s), 3.70 (3H, s), 2.20 (3H, s), 2.18 (3H, s), 1.31 (3H, t). This compound 8-17: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.51 (1H, dd), 7.38 (1H, d), 7.21 (1H, d), 4.16 (2H, t), 3.82 (3H, s), 3.69 (3H, s), 2.20 (3H, s), 2.18 (3H, s), 1.76-1.65 (2H, m), 1.41-1.32 (4H, m), 0.94-0.88 (3H, m). This compound 8-18: 1 H-NMR (CDCl3) δ: 7.65 (1H, dd), 7.60 (1H, s), 7.52 (1H, d), 7.35-7.25 (5H, m), 7.04-6.99 (1H, m), 3.84 (3H, s), 3.71 (3H, s), 2.42 (3H, s), 2.21 (3H, s). This compound 8-19: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.50 (1H, dd), 7.38 (1H, d), 7.21 (1H, d), 3.95 (3H, s), 3.81 (3H, s), 3.69 (3H, s), 2.71 (2H, q), 2.18 (3H, s), 1.13 (3H, t). This compound 8-20: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.51 (1H, dd), 7.38 (1H, d), 7.21 (1H, d), 4.21 (2H, q), 3.82 (3H, s), 3.70 (3H, s), 2.72 (2H, q), 2.18 (3H, s), 1.30 (3H, t), 1.13 (3H, t). Compound 8-21 of the present invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.52 (1H, dd), 7.38 (1H, d), 7.20 (1H, d), 4.21-4.14 (1H, m), 3.82 (3H, s), 3.69 (3H, s), 2.20 (3H, s), 2.18 (3H, s), 2.03-1.93 (2H, m), 1.79-1.69 (2H, m), 1.58-1.28 (6H, m).

[0146] Manufacturing Example 7 A mixture of 0.04 g of sodium hydride (60% oil) and 3 mL of DMF was stirred at 0°C for 30 minutes. To the resulting mixture, 0.25 g of Intermediate 4 was added under ice-cooling, and the mixture was stirred at room temperature for 4 hours. 0.16 mL of (bromomethyl)cyclobutane was added to the resulting mixture at 0°C, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 0.20 g of the present invention compound 9-1, represented by the following formula: [ka] Compound 9-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.51 (1H, d), 7.38 (1H, s), 7.20 (1H, d), 4.15 (2H, d), 3.82 (3H, s), 3.70 (3H, s), 2.75-2.67 (1H, m), 2.20 (3H, s), 2.18 (3H, s), 2.10-2.04 (2H, m), 1.96-1.79 (4H, m).

[0147] Manufacturing Example 7-1 The compounds produced according to Production Example 7 and their physical properties are shown below. In the compound represented by formula (1h), R 4 and R5 [Table A8] describes the combination of のいずれかの and せである compounds.

[0148] Table 16 Compound 9-2 of this invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.52 (1H, dd), 7.39-7.37 (2H, m), 7.24-7.17 (4H, m), 5.23 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.39 (3H, s), 2.23 (3H, s), 2.18 (3H, s). Compound 9-3 of this invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.52 (1H, dd), 7.39 (1H, d), 7.23-7.21 (4H, m), 7.11 (1H, d), 5.19 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.23 (3H, s), 2.18 (3H, s). Compound 9-4 of this invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.52 (1H, dd), 7.38 (1H, d), 7.31 (2H, d), 7.20 (1H, d), 7.16 (2H, d), 5.17 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.35 (3H, s), 2.22 (3H, s), 2.18 (3H, s). Compound 9-5 of this invention: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.52 (1H, dd), 7.47-7.43 (1H, m), 7.38 (1H, d), 7.30-7.25 (1H, m), 7.20 (1H, d), 7.14-7.10 (1H, m), 7.07-7.03 (1H, m), 5.29 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.23 (3H, s), 2.18 (3H, s). Compound 9-6 of the present invention: 1 H-NMR (CDCl3) δ:7.58-7.50 (3H, m), 7.39 (1H, d), 7.20 (2H, dd), 7.04 (1H, d), 5.32 (2H, s), 3.81 (3H, s), 3.69 (3H, s), 2.56 (3H, s), 2.30 (3H, s), 2.17 (3H, s).

[0149] Manufacturing Example 8 A mixture of 0.45 g of Intermediate 8, 0.23 g of butanol, 0.62 g of bis(2-methoxyethyl) azodicarboxylate, 0.64 g of triphenylphosphine, and 5 mL of chloroform was stirred at room temperature for 1 hour. The resulting mixture was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.21 g of the present invention compound 10-1 represented by the following formula. [ka] Compound 10-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.11 (1H, d), 6.77 (1H, dd), 6.67 (1H, d), 3.92 (2H, t), 3.82 (3H, s), 3.70 (3H, s), 2.10 (3H, s), 1.77-1.70 (2H, m), 1.52-1.43 (2H, m), 0.96 (3H, t).

[0150] Manufacturing Example 8-1 The compounds produced according to Production Example 8 and their physical properties are shown below. Formula (1k): [ka] In the compound represented by the formula 6 Compounds 10-2 to 10-8 of the present invention each represent a substituent as shown below. Compound 10-2 of the present invention (R 6 :Pr): 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.11 (1H, d), 6.77 (1H, dd), 6.67 (1H, d), 3.88 (2H, t), 3.82 (3H, s), 3.70 (3H, s), 2.10 (3H, s), 1.83-1.74 (2H, m), 1.02 (3H, t). Compound 10-3 of the present invention (R 6 :CH2CHMe2): 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.11 (1H, d), 6.77 (1H, dd), 6.66 (1H, d), 3.82 (3H, s), 3.70 (3H, s), 3.68 (2H, d), 2.10 (3H, s), 2.09-2.00 (1H, m), 1.00 (6H, d). Compound 10-4 of the present invention (R 6 :CH2CH3): 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.11 (1H, d), 6.77 (1H, dd), 6.67 (1H, d), 4.00 (2H, q), 3.82 (3H, s), 3.70 (3H, s), 2.10 (3H, s), 1.38 (3H, t). Compound 10-5 of the present invention (R 6 :CH2(c-Pr)): 1H-NMR (CDCl3) δ: 7.54 (1H, s), 7.11 (1H, d), 6.78 (1H, dd), 6.67 (1H, d), 3.82 (3H, s), 3.76 (2H, d), 3.70 (3H, s), 2.10 (3H, s), 1.29-1.23 (1H, m), 0.6-0.60 (2H, m), 0.34-0.30 (2H, m). This compound 10-6(R 6 :CH2CH2OMe): 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.11 (1H, d), 6.80 (1H, dd), 6.70 (1H, d), 4.10-4.08 (2H, m), 3.82 (3H, s), 3.74-3.70 (2H, m), 3.69 (3H, s), 3.44 (3H, s), 2.10 (3H, s). This compound 10-7(R 6 :Pen): 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 7.10 (1H, d), 6.76 (1H, dd), 6.66 (1H, d), 3.91 (2H, t), 3.82 (3H, s), 3.69 (3H, s), 2.09 (3H, s), 1.80-1.71 (2H, m), 1.46-1.31 (4H, m), 0.91 (3H, t). This compound 10-8(R 6 :CH2CH2F): 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.13 (1H, d), 6.80 (1H, dd), 6.70 (1H, d), 4.73 (2H, dt), 4.18 (2H, dt), 3.82 (3H, s), 3.69 (3H, s), 2.10 (3H, s).

[0151] Manufacturing example 9 Under a nitrogen atmosphere, a mixture of 0.30 g of intermediate 1, 0.43 g of cyclohexene, 0.13 g of acetylacetonate palladium(II), 0.16 g of diisopropylamine, 0.06 g of tri-tert-butylphosphine tetrafluoroborate, and 3 mL of N,N'-dimethylpropyleneurea was stirred at 130 °C for 5 hours. The resulting mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:2) to obtain 0.20 g of the present invention compound 3-8 represented by the following formula. [ka] Inventive compound 3-8: LCMS: 287 [M+H] + , RT = 2.27 minutes

[0152] Manufacturing Example 9-1 The compounds prepared according to Preparation Example 9 and their physical properties are shown below. [ka] Compounds 3-9 of the present invention: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 7.29 (1H, dd), 7.18-7.15 (2H, m), 6.12-6.10 (1H, m), 3.81 (3H, s), 3.69 (3H, s), 2.70-2.65 (2H, m), 2.53-2.47 (2H, m), 2.16 (3H, s), 2.02-1.97 (2H, m).

[0153] Manufacturing Example 10 Under a nitrogen atmosphere, 0.25 g of Intermediate 8, 0.23 g of potassium carbonate, and 5 mL of acetonitrile were mixed with 0.17 mL of dimethylcarbamoyl chloride at 0°C and stirred at room temperature for 7 hours. A saturated aqueous solution of sodium bicarbonate was added to the resulting mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to obtain 0.27 g of the present invention compound 11-1, represented by the following formula: [ka] Compound 11-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.18 (1H, d), 6.99 (1H, dd), 6.87 (1H, d), 3.81 (3H, s), 3.69 (3H, s), 3.07 (3H, s), 3.00 (3H, s), 2.14 (3H, s).

[0154] Manufacturing Example 10-1 The compounds prepared according to Preparation Example 10 and their physical properties are shown below. [ka] Compound 11-2 of the present invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 7.18 (1H, d), 7.00 (1H, dd), 6.88 (1H, d), 3.81 (3H, s), 3.69 (3H, s), 3.46-3.32 (4H, m), 2.14 (3H, s), 1.26-1.15 (6H, m).

[0155] [ka] Compound 11-3 of the present invention: 1H-NMR (CDCl3) δ: 7.53 (1H, s), 7.41-7.31 (4H, m), 7.28-7.21 (1H, m), 7.17 (1H, d), 7.02-6.97 (1H, m), 6.85 (1H, s), 3.80 (3H, s), 3.67 (3H, s), 3.41 (3H, s), 2.13 (3H, s).

[0156] Next, examples of the compounds of the present invention and intermediates produced according to any of the production examples described in the Examples and the production methods described in this specification are shown below.

[0157] Formula (1A): [ka] In the compound represented by the formula (hereinafter referred to as compound (1A)), Q is Q1, and R 1 is a methyl group, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX1).

[0158] Group X: Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, (CH2)3CH3, CH2CH(CH3)2, CH(CH3)CH2CH3, t-Bu, CH2c-Pr, (CH2)4CH3, (CH2)2CH(CH3)2, CH(CH3)(CH2)2CH3, CH(CH2CH3)CH2CH3, CH2CH(CH3)CH2CH3, C(CH3)2CH2CH3, CH2t-Bu, CH2c-Bu, CH2c-Pen, (CH2)2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopropyl)methyl, 1-cyclopropylethyl, (CH2)3c-Pr, (CH2)5CH3, (CH2)3CH(CH3)2, (CH2)2CH(CH3)CH2CH3, CH2CH(CH3)(CH2)2CH3, CH(CH3)(CH2)3CH3, CH2CH(CH2CH3)2, heptyl, CH2CH=CH2, CH2CH=CHCH3, CH2CH=C(CH3)2, CH2CH=CF2, CH2CH=CCl2, CH2CH=CHCH2CH3, CH2CH=CH(CH2)2CH3, CH2C(CH3)=CH2, CH2C(CH3)=CHCH3, CH2C(CH3)=C(CH3)2, CH2C(CH3)=CHCH2CH 3,CH2CF=CH2,CH2CF=CHCH3,CH2CF=C(CH3)2,CH2CF=CF2,CH2CF=CHCH2CH3,CH2CF=CH(CH2)2CH3,CH2CCl=C H2,CH2CCl=CHCH3,CH2CCl=C(CH3)2,CH2CCl=CCl2,CH2CCl=CHCH2CH3,CH2CCl=CH(CH2)2CH3,(CH2)2CH= CH2,(CH2)2CH=CHCH3,(CH2)2CH=CHCH2CH3,(CH2)2CH=C(CH3)2,(CH2)2C(CH3)=CH2,(CH2)2C(CH3)=CHC H3,(CH2)3CH=CH2,(CH2)3C(CH3)=CH2,(CH2)4CH=CH2,CH2C≡CH,CH2C≡CCH3,CH2C≡CCH2CH3,CH2C≡Cc-Pr, The group consisting of (CH2)2C≡CH, (CH2)2C≡CCH3, (CH2)2C≡CCH2CH3, (CH2)3C≡CH, (CH2)3C≡CCH3, CH2Cl, CH2Br, CH2OCH3, CH2OCH2CH3, CH2O(CH2)2CH3, CHF2, CF3, CH2CF3, CH2CHF2, CH2CH2CHF2, CH2CH2CF3, CH2CF2CF3, (CH2)2CF2CF3, CH2(CF2)2CF3, (CH2)2CF(CF3)2, (CH2)2(CF2)5CF3, CF3, CF2CHF(CF3), CF2CHF(OCF3), CH2CF2CF2H.

[0159] In compound (1A), Q is Q1 and R 1 is a chlorine atom, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX2). In compound (1A), Q is Q1 and R 1 is a fluorine atom, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX3). In compound (1A), Q is Q1 and R 1 is an ethyl group, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX4). In compound (1A), Q is Q1 and R 1 is a cyclopropyl group, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX5). In compound (1A), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX6). In compound (1A), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX7). In compound (1A), Q is Q2, L is NH, and R 1 is a methyl group, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX8). In compound (1A), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 7 is any substituent selected from group X (hereinafter referred to as compound group SX9).

[0160] Formula (1B): [ka] In the compound represented by the formula (hereinafter referred to as compound (1B)), Q is Q1, and R 1 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX10).

[0161] Combination A consists of substituent numbers ZA1 to ZA312. Substituent numbers ZA1 to ZA312 refer to R in compound (1B), compound represented by formula (1D), compound represented by formula (1F), compound represented by formula (1I), compound represented by formula (1M), compound represented by formula (1N), compound represented by formula (1O), compound represented by formula (1P), compound represented by formula (1Q), compound represented by formula (1R), compound represented by formula (1S), compound represented by formula (1T), compound represented by formula (2C), and compound represented by formula (2E). X2 , R X3 , R X4 , R X5 , and R X6 The following represents a combination of [substituent number; R X2 , R X3 , R X4 , R X5 , R X6 For example, the substituent number ZA2 is R X2 is a methyl group, and R X3 , R X4 , R X5 , and R X6 is a hydrogen atom.

[0162] Combination A [ZA1;H,H,H,H,H],[ZA2;Me,H,H,H,H],[ZA3;F,H,H,H,H],[ZA4;Cl,H,H,H,H],[ZA5;OMe,H,H,H,H],[ZA6;CF3,H,H,H,H],[ZA7;H,Me,H,H,H],[ZA8;H,Et,H,H,H],[ZA9;H,Pr,H,H,H],[ZA10;H,i-Pr,H,H,H],[ZA11;H,t-Bu,H,H,H],[ZA12;H,OMe,H,H,H],[ZA13;H,OEt,H,H,H],[ZA14;H,OPr,H,H,H],[ZA15;H,Oi-Pr,H,H,H],[ZA16;H,CF3,H,H,H],[ZA17;H,CF2H,H,H,H],[ZA18;H,CFH2,H,H,H],[ZA19;H,F,H,H,H],[ZA20;H,Cl,H,H,H],[ZA21;H,Br,H,H,H],[ZA22;H,CN,H,H,H],[ZA23;H,Ph,H,H,H],[ZA24;H,OPh,H,H,H],[ZA25;H,c-Pr,H,H,H],[ZA26;H,c-Pen,H,H,H],[ZA27;H,c-Hex,H,H,H],[ZA28;H,H,Me,H,H],[ZA29;H,H,Et,H,H],[ZA30;H,H,Pr,H,H],[ZA31;H,H,i-Pr,H,H],[ZA32;H,H,t-Bu,H,H],[ZA33;H,H,OMe,H,H],[ZA34;H,H,OEt,H,H],[ZA35;H,H,OPr,H,H],[ZA36;H,H,Oi-Pr,H,H],[ZA37;H,H,CF3,H,H],[ZA38;H,H,CF2H,H,H],[ZA39;H,H,CFH2,H,H],[ZA40;H,H,F,H,H],[ZA41;H,H,Cl,H,H],[ZA42;H,H,Br,H,H],[ZA43;H,H,CN,H,H],[ZA44;H,H,Ph,H,H],[ZA45;H,H,OPh,H,H],[ZA46;H,H,c-Pr,H,H],[ZA47;H,H,c-Pen,H,H],[ZA48;H,H,c-Hex,H,H],[ZA49;H,H,H,H,F],[ZA50;Me,H,H,H,F],[ZA51;F,H,H,H,F],[ZA52;Cl,H,H,H,F],[ZA53;H,Me,H,H,F],[ZA54;H,Et,H,H,F],[ZA55;H,Pr,H,H,F],[ZA56;H,i-Pr,H,H,F],[ZA57;H,t-Bu,H,H,F],[ZA58;H,OMe,H,H,F],[ZA59;H,OEt,H,H,F],[ZA60;H,OPr,H,H,F],[ZA61;H,Oi-Pr,H,H,F],[ZA62;H,CF3,H,H,F],[ZA63;H,CF2H,H,H,F],[ZA64;H,CFH2,H,H,F],[ZA65;H,F,H,H,F],[ZA66;H,Cl,H,H,F],[ZA67;H,Br,H,H,F],[ZA68;H,CN,H,H,F],[ZA69;H,Ph,H,H,F],[ZA70;H,OPh,H,H,F],[ZA71;H,c-Pr,H,H,F],[ZA72;H,c-Pen,H,H,F],[ZA73;H,c-Hex,H,H,F],[ZA74;H,H,Me,H,F],[ZA75;H,H,Et,H,F],[ZA76;H,H,Pr,H,F],[ZA77;H,H,i-Pr,H,F],[ZA78;H,H,t-Bu,H,F],[ZA79;H,H,OMe,H,F],[ZA80;H,H,OEt,H,F],[ZA81;H,H,OPr,H,F],[ZA82;H,H,Oi-Pr,H,F],[ZA83;H,H,CF3,H,F],[ZA84;H,H,CF2H,H,F],[ZA85;H,H,CFH2,H,F],[ZA86;H,H,F,H,F],[ZA87;H,H,Cl,H,F],[ZA88;H,H,Br,H,F],[ZA89;H,H,CN,H,F],[ZA90;H,H,Ph,H,F],[ZA91;H,H,OPh,H,F],[ZA92;H,H,c-Pr,H,F],[ZA93;H,H,c-Pen,H,F],[ZA94;H,H,c-Hex,H,F],[ZA95;H,H,H,H,Cl],[ZA96;Me,H,H,H,Cl],[ZA97;F,H,H,H,Cl],[ZA98;Cl,H,H,H,Cl],[ZA99;H,Me,H,H,Cl],[ZA100;H,Et,H,H,Cl],[ZA101;H,Pr,H,H,Cl],[ZA102;H,i-Pr,H,H,Cl],[ZA103;H,t-Bu,H,H,Cl],[ZA104;H,OMe,H,H,Cl],[ZA105;H,OEt,H,H,Cl],[ZA106;H,OPr,H,H,Cl],[ZA107;H,Oi-Pr,H,H,Cl],[ZA108;H,CF3,H,H,Cl],[ZA109;H,CF2H,H,H,Cl],[ZA110;H,CFH2,H,H,Cl],[ZA111;H,F,H,H,Cl],[ZA112;H,Cl,H,H,Cl],[ZA113;H,Br,H,H,Cl],[ZA114;H,CN,H,H,Cl],[ZA115;H,Ph,H,H,Cl],[ZA116;H,OPh,H,H,Cl],[ZA117;H,c-Pr,H,H,Cl],[ZA118;H,H,H,F,F],[ZA119;F,H,H,F,F],[ZA120;H,H,Me,H,Cl],[ZA121;H,H,Et,H,Cl],[ZA122;H,H,Pr,H,Cl],[ZA123;H,H,i-Pr,H,Cl],[ZA124;H,H,t-Bu,H,Cl],[ZA125;H,H,OMe,H,Cl],[ZA126;H,H,OEt,H,Cl],[ZA127;H,H,OPr,H,Cl],[ZA128;H,H,Oi-Pr,H,Cl],[ZA129;H,H,CF3,H,Cl],[ZA130;H,H,CF2H,H,Cl],[ZA131;H,H,CFH2,H,Cl],[ZA132;H,H,F,H,Cl],[ZA133;H,H,Cl,H,Cl],[ZA134;H,H,Br,H,Cl],[ZA135;H,H,CN,H,Cl],[ZA136;H,H,Ph,H,Cl],[ZA137;H,H,OPh,H,Cl],[ZA138;H,H,c-Pr,H,Cl],[ZA139;H,H,c-Pen,H,Cl],[ZA140;H,H,c-Hex,H,Cl],[ZA141;H,H,H,H,Me],[ZA142;Me,H,H,H,Me],[ZA143;F,H,H,H,Me],[ZA144;Cl,H,H,H,Me],[ZA145;H,Me,H,H,Me],[ZA146;H,Et,H,H,Me],[ZA147;H,Pr,H,H,Me],[ZA148;H,i-Pr,H,H,Me],[ZA149;H,t-Bu,H,H,Me],[ZA150;H,OMe,H,H,Me],[ZA151;H,OEt,H,H,Me],[ZA152;H,OPr,H,H,Me],[ZA153;H,Oi-Pr,H,H,Me],[ZA154;H,CF3,H,H,Me],[ZA155;H,CF2H,H,H,Me],[ZA156;H,CFH2,H,H,Me],[ZA157;H,F,H,H,Me],[ZA158;H,Cl,H,H,Me],[ZA159;H,Br,H,H,Me],[ZA160;H,CN,H,H,Me],[ZA161;H,Ph,H,H,Me],[ZA162;H,OPh,H,H,Me],[ZA163;H,c-Pr,H,H,Me],[ZA164;H,c-Pen,H,H,Me],[ZA165;H,c-Hex,H,H,Me],[ZA166;H,H,Me,H,Me],[ZA167;H,H,Et,H,Me],[ZA168;H,H,Pr,H,Me],[ZA169;H,H,i-Pr,H,Me],[ZA170;H,H,t-Bu,H,Me],[ZA171;H,H,OMe,H,Me],[ZA172;H,H,OEt,H,Me],[ZA173;H,H,OPr,H,Me],[ZA174;H,H,Oi-Pr,H,Me],[ZA175;H,H,CF3,H,Me],[ZA176;H,H,CF2H,H,Me],[ZA177;H,H,CFH2,H,Me],[ZA178;H,H,F,H,Me],[ZA179;H,H,Cl,H,Me],[ZA180;H,H,Br,H,Me],[ZA181;H,H,CN,H,Me],[ZA182;H,H,Ph,H,Me],[ZA183;H,H,OPh,H,Me],[ZA184;H,H,c-Pr,H,Me],[ZA185;H,H,c-Pen,H,Me],[ZA186;H,H,c-Hex,H,Me],[ZA187;H,H,H,H,OMe],[ZA188;Me,H,H,H,OMe],[ZA189;F,H,H,H,OMe],[ZA190;Cl,H,H,H,OMe],[ZA191;H,Me,H,H,OMe],[ZA192;H,Et,H,H,OMe],[ZA193;H,Pr,H,H,OMe],[ZA194;H,i-Pr,H,H,OMe],[ZA195;H,t-Bu,H,H,OMe],[ZA196;H,OMe,H,H,OMe],[ZA197;H,OEt,H,H,OMe],[ZA198;H,OPr,H,H,OMe],[ZA199;H,Oi-Pr,H,H,OMe],[ZA200;H,CF3,H,H,OMe], [ZA201;H,CF2H,H,H,OMe],[ZA202;H,CFH2,H,H,OMe],[ZA203;H,F,H,H,OMe],[ZA204;H,Cl,H,H,OMe],[ZA205;H,Br,H,H,OMe],[ZA206;H,CN,H,H,OMe],[ZA207;H,Ph,H,H,OMe],[ZA208;H,OPh,H,H,OMe],[ZA209;H,c-Pr,H,H,OMe],[ZA210;H,c-Pen,H,H,OMe],[ZA211;H,c-Hex,H,H,OMe],[ZA212;H,H,Me,H,OMe],[ZA213;H,H,Et,H,OMe],[ZA214;H,H,Pr,H,OMe],[ZA215;H,H,i-Pr,H,OMe],[ZA216;H,H,t-Bu,H,OMe],[ZA217;H,H,OMe,H,OMe],[ZA218;H,H,OEt,H,OMe],[ZA219;H,H,OPr,H,OMe],[ZA220;H,H,Oi-Pr,H,OMe],[ZA221;H,H,CF3,H,OMe],[ZA222;H,H,CF2H,H,OMe],[ZA223;H,H,CFH2,H,OMe],[ZA224;H,H,F,H,OMe],[ZA225;H,H,Cl,H,OMe],[ZA226;H,H,Br,H,OMe],[ZA227;H,H,CN,H,OMe],[ZA228;H,H,Ph,H,OMe],[ZA229;H,H,OPh,H,OMe],[ZA230;H,H,c-Pr,H,OMe],[ZA231;H,H,c-Pen,H,OMe],[ZA232;H,H,c-Hex,H,OMe],[ZA233;H,H,H,H,CF3],[ZA234;Me,H,H,H,CF3],[ZA235;F,H,H,H,CF3],[ZA236;Cl,H,H,H,CF3],[ZA237;H,Me,H,H,CF3],[ZA238;H,Et,H,H,CF3],[ZA239;H,Pr,H,H,CF3],[ZA240;H,i-Pr,H,H,CF3],[ZA241;H,t-Bu,H,H,CF3],[ZA242;H,OMe,H,H,CF3],[ZA243;H,OEt,H,H,CF3],[ZA244;H,OPr,H,H,CF3],[ZA245;H,Oi-Pr,H,H,CF3],[ZA246;H,CF3,H,H,CF3],[ZA247;H,CF2H,H,H,CF3],[ZA248;H,CFH2,H,H,CF3],[ZA249;H,F,H,H,CF3],[ZA250;H,Cl,H,H,CF3],[ZA251;H,Br,H,H,CF3],[ZA252;H,CN,H,H,CF3],[ZA253;H,Ph,H,H,CF3],[ZA254;H,OPh,H,H,CF3],[ZA255;H,c-Pr,H,H,CF3],[ZA256;H,c-Pen,H,H,CF3],[ZA257;H,c-Hex,H,H,CF3],[ZA258;H,H,Me,H,CF3],[ZA259;H,H,Et,H,CF3],[ZA260;H,H,Pr,H,CF3],[ZA261;H,H,i-Pr,H,CF3],[ZA262;H,H,t-Bu,H,CF3],[ZA263;H,H,OMe,H,CF3],[ZA264;H,H,OEt,H,CF3],[ZA265;H,H,OPr,H,CF3],[ZA266;H,H,Oi-Pr,H,CF3],[ZA267;H,H,CF3,H,CF3],[ZA268;H,H,CF2H,H,CF3],[ZA269;H,H,CFH2,H,CF3],[ZA270;H,H,F,H,CF3],[ZA271;H,H,Cl,H,CF3],[ZA272;H,H,Br,H,CF3],[ZA273;H,H,CN,H,CF3],[ZA274;H,H,Ph,H,CF3],[ZA275;H,H,OPh,H,CF3],[ZA276;H,H,c-Pr,H,CF3],[ZA277;H,H,c-Pen,H,CF3],[ZA278;H,H,c-Hex,H,CF3],[ZA279;H,F,F,H,H],[ZA280;H,F,H,F,H],[ZA281;H,F,F,F,H],[ZA282;F,F,F,H,H],[ZA283;F,F,H,F,H],[ZA284;F,H,F,H,F],[ZA285;F,F,F,F,F],[ZA286;F,F,H,F,F],[ZA287;H,OMe,H,OMe,H],[ZA288;H,F,Cl,H,H],[ZA289;H,F,Me,H,H],[ZA290;H,F,OMe,H,H],[ZA291;H,F,CF3,H,H],[ZA292;H,Cl,F,H,H],[ZA293;H,Cl,Cl,H,H],[ZA294;H,Cl,Me,H,H],[ZA295;H,Cl,OMe,H,H],[ZA296;H,Cl,CF 3,H,H],[ZA297;H,Me,F,H,H],[ZA298;H,Me,Cl,H,H],[ZA299;H,Me,Me,H,H],[ZA300;H,Me,OMe,H,H], [ZA301;H,Me,CF3,H,H],[ZA302;H,OMe,F,H,H],[ZA303;H,OMe,Cl,H,H],[ZA304;H,OMe,Me,H,H],[ZA305;H,OMe,OMe,H,H],[ZA306;H,OMe,CF3,H, H],[ZA307;H,CF3,F,H,H],[ZA308;H,CF3,Cl,H,H],[ZA309;H,CF3,F,H,H],[ZA310;H,CF3,Cl,H,H],[ZA311;H,CF3,F,H,H],[ZA312;H,Cl,H,Cl,H];

[0163] In compound (1B), Q is Q1 and R 1 is a chlorine atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX11). In compound (1B), Q is Q1 and R 1 is a fluorine atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX12). In compound (1B), Q is Q1 and R 1 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX13). In compound (1B), Q is Q1 and R1 is a cyclopropyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX14). In compound (1B), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX15). In compound (1B), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX16). In compound (1B), Q is Q2, L is NH, and R 1 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX17). In compound (1B), Q is Q2, L is NH, and R 1 is a chlorine atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX18).

[0164] Formula (1C): [ka] In the compound represented by the formula (hereinafter referred to as compound (1C)), R 1 is a methyl group, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX19). In compound (1C), Q is Q1 and R 1 is a chlorine atom, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX20). In compound (1C), Q is Q1 and R 1 is a fluorine atom, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX21). In compound (1C), Q is Q1 and R 1 is an ethyl group, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX22). In compound (1C), Q is Q1 and R 1 is a cyclopropyl group, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX23). In compound (1C), Q is Q1 and R 1 is a methyl group, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX24). In compound (1C), Q is Q1 and R 1 is a chlorine atom, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX25). In compound (1C), Q is Q1 and R 1 is a fluorine atom, and R 4is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX26). In compound (1C), Q is Q1 and R 1 is an ethyl group, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX27). In compound (1C), Q is Q1 and R 1 is a cyclopropyl group, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX28). In compound (1C), Q is Q1 and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX29). In compound (1C), Q is Q1 and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX30). In compound (1C), Q is Q1 and R 1 is a fluorine atom, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX31). In compound (1C), Q is Q1 and R 1 is an ethyl group, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX32). In compound (1C), Q is Q1 and R 1 is a cyclopropyl group, and R 4 is a hydrogen atom, and R 5is any substituent selected from group X (hereinafter referred to as compound group SX33). In compound (1C), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX34). In compound (1C), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX35). In compound (1C), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX36). In compound (1C), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX37). In compound (1C), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX38). In compound (1C), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX39). In compound (1C), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a methyl group, and R 5is any substituent selected from group X (hereinafter referred to as compound group SX40). In compound (1C), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX41). In compound (1C), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX42). In compound (1C), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX43). In compound (1C), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX44). In compound (1C), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter referred to as compound group SX45).

[0165] Formula (1D): [ka] In the compound represented by the formula (hereinafter referred to as compound (1D)), Q is Q1, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5, and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX46). In compound (1D), Q is Q1 and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX47). In compound (1D), Q is Q1 and R 1 is a fluorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX48). In compound (1D), Q is Q1 and R 1 is an ethyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX49). In compound (1D), Q is Q1 and R 1 is a cyclopropyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX50). In compound (1D), Q is Q1 and R 1 is a methyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6is any one of the combinations described in Combination A (hereinafter referred to as compound group SX51). In compound (1D), Q is Q1 and R 1 is a chlorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX52). In compound (1D), Q is Q1 and R 1 is a fluorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX53). In compound (1D), Q is Q1 and R 1 is an ethyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX54). In compound (1D), Q is Q1 and R 1 is a cyclopropyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX55). In compound (1D), Q is Q1 and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6is any one of the combinations described in Combination A (hereinafter referred to as compound group SX56). In compound (1D), Q is Q1 and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX57). In compound (1D), Q is Q1 and R 1 is a fluorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX58). In compound (1D), R 1 is an ethyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX59). In compound (1D), Q is Q1 and R 1 is a cyclopropyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX60). In compound (1D), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6is any one of the combinations described in Combination A (hereinafter referred to as compound group SX61). In compound (1D), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX62). In compound (1D), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX63). In compound (1D), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX64). In compound (1D), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX65). In compound (1D), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , RX5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX66). In compound (1D), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX67). In compound (1D), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX68). In compound (1D), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX69). In compound (1D), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX70). In compound (1D), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , RX4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX71). In compound (1D), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX72).

[0166] Formula (1E): [ka] In the compound represented by the formula (hereinafter referred to as compound (1E)), Q is Q1, and R 1 is a methyl group, and R 4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX73). In compound (1E), Q is Q1 and R 1 is a chlorine atom, and R 4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX74). In compound (1E), Q is Q1 and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX75). In compound (1E), Q is Q1 and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX76). In compound (1E), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX77). In compound (1E), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX78). In compound (1E), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX79). In compound (1E), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX80). In compound (1E), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX81). In compound (1E), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX82). In compound (1E), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX83). In compound (1E), Q is Q2, L is NH, and R 1 is a chlorine atom, and R4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter referred to as compound group SX84).

[0167] Formula (1F): [ka] In the compound represented by the formula (hereinafter referred to as compound (1F)), Q is Q1, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX85). In compound (1F), Q is Q1 and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX86). In compound (1F), Q is Q1 and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX87). In compound (1F), Q is Q1 and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX88). In compound (1F), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX89). In compound (1F), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX90). In compound (1F), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX91). In compound (1F), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX92). In compound (1F), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6is any one of the combinations described in Combination A (hereinafter referred to as compound group SX93). In compound (1F), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX94). In compound (1F), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX95). In compound (1F), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX96).

[0168] Formula (1G): [ka] In the compound represented by the formula (hereinafter referred to as compound (1G)), Q is Q1, and R 1 is a methyl group, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX97).

[0169] Group Y: Et, Pr, i-Pr, (CH2)3CH3, CH2CH(CH3)2, CH(CH3)CH2CH3, t-Bu, CH2c-Pr, (CH2)4CH3, (CH2)2CH(CH3)2, CH(CH3)(CH2)2CH3, CH(CH2CH3)CH2CH3, CH2CH(CH3)CH2CH3, C(CH3)2CH2CH3, CH2t-Bu, CH2c-Bu, CH2c-Pen, (CH2)2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopropyl)methyl, 1-cyclopropylethyl, (CH2)3c-Pr, (CH2)5CH3, (CH2)3CH(CH3)2, (CH2)2CH(CH3)CH2CH3, CH2CH(CH3)(CH2)2CH3, CH(CH3)(CH2)3CH3, CH2CH(CH2CH3)2, heptyl, CH2CH=CH2, CH2CH=CHCH3, CH2CH=C(CH3)2, CH2CH=CF2, CH2CH=CCl2, CH2CH=CHCH2CH3, CH2CH=CH(CH2)2CH3, CH2C(CH3)=CH2, CH2C(CH3)=CHCH3, CH2C(CH3)=C(CH3)2, CH2C(CH3)=CHCH2CH 3,CH2CF=CH2,CH2CF=CHCH3,CH2CF=C(CH3)2,CH2CF=CF2,CH2CF=CHCH2CH3,CH2CF=CH(CH2)2CH3,CH2CCl=C H2,CH2CCl=CHCH3,CH2CCl=C(CH3)2,CH2CCl=CCl2,CH2CCl=CHCH2CH3,CH2CCl=CH(CH2)2CH3,(CH2)2CH= CH2,(CH2)2CH=CHCH3,(CH2)2CH=CHCH2CH3,(CH2)2CH=C(CH3)2,(CH2)2C(CH3)=CH2,(CH2)2C(CH3)=CHC H3,(CH2)3CH=CH2,(CH2)3C(CH3)=CH2,(CH2)4CH=CH2,CH2C≡CH,CH2C≡CCH3,CH2C≡CCH2CH3,CH2C≡Cc-Pr, (CH2)2C≡CH,(CH2)2C≡CCH3,(CH2)2C≡CCH2CH3,(CH2)3C≡CH,(CH2)3C≡CCH3,CH2Cl,CH2Br, CH2OCH3,CH2OCH2CH3,CH2CH2OCH3,CH2O(CH2)2CH3,CHF2,CF3,CH2CF3,CH2CHF2,CH2CH2F,C H2CH2CH2F,CH2CH2CHF2,CH2CH2CF3,CH2CF2CF3,(CH2)2CF2CF3,CH2(CF2)2CF3,(CH2)2CF( A group consisting of CF3)2,(CH2)2(CF2)5CF3,CF3,CF2CHF(CF3),CF2CHF(OCF3),CH2CF2CF2H,c-Pr,c-Bu.

[0170] In compound (1G), Q is Q1 and R 1 is a chlorine atom, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX98). In compound (1G), Q is Q1 and R 1 is a fluorine atom, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX99). In compound (1G), Q is Q1 and R 1 is an ethyl group, and R 6is any substituent selected from group Y (hereinafter referred to as compound group SX100). In compound (1G), Q is Q1 and R 1 is a cyclopropyl group, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX101). In compound (1G), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX102). In compound (1G), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX103). In compound (1G), Q is Q2, L is NH, and R 1 is a methyl group, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX104). In compound (1G), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX105).

[0171] Formula (1H): [ka] In the compound represented by the formula (hereinafter referred to as compound (1H)), Q is Q1, and R 1 is a methyl group, and R 4 is a methyl group, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX106). In compound (1H), Q is Q1 and R 1 is a chlorine atom, and R 4 is a methyl group, and R 13is any substituent selected from group X (hereinafter referred to as compound group SX107). In compound (1H), Q is Q1 and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX108). In compound (1H), Q is Q1 and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX109). In compound (1H), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a methyl group, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX110). In compound (1H), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a methyl group, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX111). In compound (1H), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX112). In compound (1H), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX113). In compound (1H), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a methyl group, and R 13is any substituent selected from group X (hereinafter referred to as compound group SX114). In compound (1H), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a methyl group, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX115). In compound (1H), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX116). In compound (1H), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter referred to as compound group SX117).

[0172] Formula (1I): [ka] In the compound represented by the formula (hereinafter referred to as compound (1I)), Q is Q1, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX118). In compound (1I), Q is Q1 and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX119). In compound (1I), Q is Q1 and R 1 is a methyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX120). In compound (1I), Q is Q1 and R 1 is a chlorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX121). In compound (1I), Q is Q1 and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX122). In compound (1I), Q is Q1 and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX123). In compound (1I), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX124). In compound (1I), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX125). In compound (1I), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX126). In compound (1I), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX127). In compound (1I), Q is Q2, L is an oxygen atom, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX128). In compound (1I), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6is any one of the combinations described in Combination A (hereinafter referred to as compound group SX129). In compound (1I), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX130). In compound (1I), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a methyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX131). In compound (1I), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX132). In compound (1I), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is an ethyl group, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX133). In compound (1I), Q is Q2, L is NH, and R 1 is a methyl group, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5, and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX134). In compound (1I), Q is Q2, L is NH, and R 1 is a chlorine atom, and R 4 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 , and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX135).

[0173] Formula (1J): [ka] [wherein G represents any one of formulae G1 to G35.] [ka] [ka] [ka] 〕 In the compound represented by the formula (hereinafter referred to as compound (1J)), Q is Q1, and R 1 is a methyl group, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 and is any one of the combinations described in Combination B (hereinafter referred to as compound group SX136).

[0174] Combination B consists of substituent numbers ZB1 to ZB1539. Substituent numbers ZB1 to ZB1539 refer to the structure of G in compound (1J) and the substituent R corresponding to the structure of G. X7 , R X8 , R X9 and R X10 The following represents a combination of [substituent number; G, R X7 ,R X8 ,RX9 ,R X10 For example, the substituent number ZB2 is G1, and R X7 is a methyl group, and R X8 , R X9 and R X10 is a hydrogen atom.

[0175] Combination B [ZB1;G1,H,H,H,H],[ZB2;G1,Me,H,H,H],[ZB3;G1,Et,H,H,H],[ZB4;G1,Pr,H,H,H],[ZB5;G1,i-Pr,H,H,H],[ZB6;G1,c-Pr,H,H,H],[ZB7;G1,Ph,H,H,H],[ZB8;G1,OMe,H,H,H],[ZB9;G1,OEt,H,H,H],[ZB10;G1,OPh,H,H,H],[ZB11;G1,CF3,H,H,H],[ZB12;G1,F,H,H,H],[ZB13;G1,Cl,H,H,H],[ZB14;G1,Br,H,H,H],[ZB15;G1,CN,H,H,H],[ZB16;G1,H,Me,H,H],[ZB17;G1,H,Et,H,H],[ZB18;G1,H,Pr,H,H],[ZB19;G1,H,i-Pr,H,H],[ZB20;G1,H,c-Pr,H,H],[ZB21;G1,H,Ph,H,H],[ZB22;G1,H,OMe,H,H],[ZB23;G1,H,OEt,H,H],[ZB24;G1,H,OPh,H,H],[ZB25;G1,H,CF3,H,H],[ZB26;G1,H,F,H,H],[ZB27;G1,H,Cl,H,H],[ZB28;G1,H,Br,H,H],[ZB29;G1,H,CN,H,H],[ZB30;G1,H,H,Me,H],[ZB31;G1,H,H,Et,H],[ZB32;G1,H,H,Pr,H],[ZB33;G1,H,H,i-Pr,H],[ZB34;G1,H,H,c-Pr,H],[ZB35;G1,H,H,Ph,H],[ZB36;G1,H,H,OMe,H],[ZB37;G1,H,H,OEt,H],[ZB38;G1,H,H,OPh,H],[ZB39;G1,H,H,CF3,H],[ZB40;G1,H,H,F,H],[ZB41;G1,H,H,Cl,H],[ZB42;G1,H,H,Br,H],[ZB43;G1,H,H,CN,H],[ZB44;G1,H,H,H,Me],[ZB45;G1,H,H,H,Et],[ZB46;G1,H,H,H,Pr],[ZB47;G1,H,H,H,i-Pr],[ZB48;G1,H,H,H,c-Pr],[ZB49;G1,H,H,H,Ph],[ZB50;G1,H,H,H,OMe],[ZB51;G1,H,H,H,OEt],[ZB52;G1,H,H,H,OPh],[ZB53;G1,H,H,H,CF3],[ZB54;G1,H,H,H,F],[ZB55;G1,H,H,H,Cl],[ZB56;G1,H,H,H,Br],[ZB57;G1,H,H,H,CN],[ZB58;G2,H,H,H,H],[ZB59;G2,Me,H,H,H],[ZB60;G2,Et,H,H,H],[ZB61;G2,Pr,H,H,H],[ZB62;G2,i-Pr,H,H,H],[ZB63;G2,c-Pr,H,H,H],[ZB64;G2,Ph,H,H,H],[ZB65;G2,OMe,H,H,H],[ZB66;G2,OEt,H,H,H],[ZB67;G2,OPh,H,H,H],[ZB68;G2,CF3,H,H,H],[ZB69;G2,F,H,H,H],[ZB70;G2,Cl,H,H,H],[ZB71;G2,Br,H,H,H],[ZB72;G2,CN,H,H,H],[ZB73;G2,H,Me,H,H],[ZB74;G2,H,Et,H,H],[ZB75;G2,H,Pr,H,H],[ZB76;G2,H,i-Pr,H,H],[ZB77;G2,H,c-Pr,H,H],[ZB78;G2,H,Ph,H,H],[ZB79;G2,H,OMe,H,H],[ZB80;G2,H,OEt,H,H],[ZB81;G2,H,OPh,H,H],[ZB82;G2,H,CF3,H,H],[ZB83;G2,H,F,H,H],[ZB84;G2,H,Cl,H,H],[ZB85;G2,H,Br,H,H],[ZB86;G2,H,CN,H,H],[ZB87;G2,H,H,Me,H],[ZB88;G2,H,H,Et,H],[ZB89;G2,H,H,Pr,H],[ZB90;G2,H,H,i-Pr,H],[ZB91;G2,H,H,c-Pr,H],[ZB92;G2,H,H,Ph,H],[ZB93;G2,H,H,OMe,H],[ZB94;G2,H,H,OEt,H],[ZB95;G2,H,H,OPh,H],[ZB96;G2,H,H,CF3,H],[ZB97;G2,H,H,F,H],[ZB98;G2,H,H,Cl,H],[ZB99;G2,H,H,Br,H],[ZB100;G2,H,H,CN,H],[ZB101;G2,H,H,H,Me],[ZB102;G2,H,H,H,Et],[ZB103;G2,H,H,H,Pr],[ZB104;G2,H,H,H,i-Pr],[ZB105;G2,H,H,H,c-Pr],[ZB1 06;G2,H,H,H,Ph],[ZB107;G2,H,H,H,OMe],[ZB108;G2,H,H,H,OEt],[ZB1 09;G2,H,H,H,OPh],[ZB110;G2,H,H,H,CF3],[ZB111;G2,H,H,H,F],[ZB1 12;G2,H,H,H,Cl],[ZB113;G2,H,H,H,Br],[ZB114;G2,H,H,H,CN],[ZB115 ;G3,H,H,H,H],[ZB116;G3,Me,H,H,H],[ZB117;G3,Et,H,H,H],[ZB118;G 3,Pr,H,H,H],[ZB119;G3,i-Pr,H,H,H],[ZB120;G3,c-Pr,H,H,H],[ZB121 ;G3,Ph,H,H,H],[ZB122;G3,OMe,H,H,H],[ZB123;G3,OEt,H,H,H],[ZB12 4;G3,OPh,H,H,H],[ZB125;G3,CF3,H,H,H],[ZB126;G3,F,H,H,H],[ZB127 ;G3,Cl,H,H,H],[ZB128;G3,Br,H,H,H],[ZB129;G3,CN,H,H,H],[ZB130; G3,H,Me,H,H],[ZB131;G3,H,Et,H,H],[ZB132;G3,H,Pr,H,H],[ZB133;G3 ,H,i-Pr,H,H],[ZB134;G3,H,c-Pr,H,H],[ZB135;G3,H,Ph,H,H],[ZB136 ;G3,H,OMe,H,H],[ZB137;G3,H,OEt,H,H],[ZB138;G3,H,OPh,H,H],[ZB13 9;G3,H,CF3,H,H],[ZB140;G3,H,F,H,H],[ZB141;G3,H,Cl,H,H],[ZB142 ;G3,H,Br,H,H],[ZB143;G3,H,CN,H,H],[ZB144;G3,H,H,Me,H],[ZB145;G 3,H,H,Et,H],[ZB146;G3,H,H,Pr,H],[ZB147;G3,H,H,i-Pr,H],[ZB148;G 3,H,H,c-Pr,H],[ZB149;G3,H,H,Ph,H],[ZB150;G3,H,H,OMe,H],[ZB151;G3,H,H,OEt,H],[ZB152;G3,H,H,OPh,H],[ZB153;G3,H,H,CF3,H],[ZB15 4;G3,H,H,F,H],[ZB155;G3,H,H,Cl,H],[ZB156;G3,H,H,Br,H],[ZB157; G3,H,H,CN,H],[ZB158;G3,H,H,H,Me],[ZB159;G3,H,H,H,Et],[ZB160;G 3,H,H,H,Pr],[ZB161;G3,H,H,H,i-Pr],[ZB162;G3,H,H,H,c-Pr],[ZB163 ;G3,H,H,H,Ph],[ZB164;G3,H,H,H,OMe],[ZB165;G3,H,H,H,OEt],[ZB16 6;G3,H,H,H,OPh],[ZB167;G3,H,H,H,CF3],[ZB168;G3,H,H,H,F],[ZB169 ;G3,H,H,H,Cl],[ZB170;G3,H,H,H,Br],[ZB171;G3,H,H,H,CN],[ZB172; G4,H,H,H,-],[ZB173;G4,Me,H,H,-],[ZB174;G4,Et,H,H,-],[ZB175;G4, Pr,H,H,-],[ZB176;G4,i-Pr,H,H,-],[ZB177;G4,c-Pr,H,H,-],[ZB178; G4,Ph,H,H,-],[ZB179;G4,OMe,H,H,-],[ZB180;G4,OEt,H,H,-],[ZB181 ;G4,OPh,H,H,-],[ZB182;G4,CF3,H,H,-],[ZB183;G4,F,H,H,-],[ZB184 ;G4,Cl,H,H,-],[ZB185;G4,Br,H,H,-],[ZB186;G4,CN,H,H,-],[ZB187;G 4,H,Me,H,-],[ZB188;G4,H,Et,H,-],[ZB189;G4,H,Pr,H,-],[ZB190;G4 ,H,i-Pr,H,-],[ZB191;G4,H,c-Pr,H,-],[ZB192;G4,H,Ph,H,-],[ZB193; G4,H,OMe,H,-],[ZB194;G4,H,OEt,H,-],[ZB195;G4,H,OPh,H,-],[ZB19 6;G4,H,CF3,H,-],[ZB197;G4,H,F,H,-],[ZB198;G4,H,Cl,H,-],[ZB199;G4,H,Br,H,-],[ZB200;G4,H,CN,H,-],[ZB201;G4,H,H,Me,-],[ZB202;G 4,H,H,Et,-],[ZB203;G4,H,H,Pr,-],[ZB204;G4,H,H,i-Pr,-],[ZB205; G4,H,H,c-Pr,-],[ZB206;G4,H,H,Ph,-],[ZB207;G4,H,H,OMe,-],[ZB20 8;G4,H,H,OEt,-],[ZB209;G4,H,H,OPh,-],[ZB210;G4,H,H,CF3,-],[ZB2 11;G4,H,H,F,-],[ZB212;G4,H,H,Cl,-],[ZB213;G4,H,H,Br,-],[ZB214 ;G4,H,H,CN,-],[ZB215;G5,H,H,H,-],[ZB216;G5,Me,H,H,-],[ZB217;G 5,Et,H,H,-],[ZB218;G5,Pr,H,H,-],[ZB219;G5,i-Pr,H,H,-],[ZB220; G5,c-Pr,H,H,-],[ZB221;G5,Ph,H,H,-],[ZB222;G5,OMe,H,H,-],[ZB223 ;G5,OEt,H,H,-],[ZB224;G5,OPh,H,H,-],[ZB225;G5,CF3,H,H,-],[ZB2 26;G5,F,H,H,-],[ZB227;G5,Cl,H,H,-],[ZB228;G5,Br,H,H,-],[ZB229 ;G5,CN,H,H,-],[ZB230;G5,H,Me,H,-],[ZB231;G5,H,Et,H,-],[ZB232; G5,H,Pr,H,-],[ZB233;G5,H,i-Pr,H,-],[ZB234;G5,H,c-Pr,H,-],[ZB23 5;G5,H,Ph,H,-],[ZB236;G5,H,OMe,H,-],[ZB237;G5,H,OEt,H,-],[ZB2 38;G5,H,OPh,H,-],[ZB239;G5,H,CF3,H,-],[ZB240;G5,H,F,H,-],[ZB2 41;G5,H,Cl,H,-],[ZB242;G5,H,Br,H,-],[ZB243;G5,H,CN,H,-],[ZB24 4;G5,H,H,Me,-],[ZB245;G5,H,H,Et,-],[ZB246;G5,H,H,Pr,-],[ZB247;G5,H,H,i-Pr,-],[ZB248;G5,H,H,c-Pr,-],[ZB249;G5,H,H,Ph,-],[ZB250;G5,H,H,OMe,-],[ZB251;G5,H,H,OEt,-],[ZB252;G5,H,H,OPh,-],[ZB253;G5,H,H,CF3,-],[ZB254;G5,H,H,F,-],[ZB255;G5,H,H,Cl,-],[ZB256;G5,H,H,Br,-],[ZB257;G5,H,H,CN,-],[ZB258;G6,H,H,H,-],[ZB259;G6,Me,H,H,-],[ZB260;G6,Et,H,H,-],[ZB261;G6,Pr,H,H,-],[ZB262;G6,i-Pr,H,H,-],[ZB263;G6,c-Pr,H,H,-],[ZB264;G6,Ph,H,H,-],[ZB265;G6,OMe,H,H,-],[ZB266;G6,OEt,H,H,-],[ZB267;G6,OPh,H,H,-],[ZB268;G6,CF3,H,H,-],[ZB269;G6,F,H,H,-],[ZB270;G6,Cl,H,H,-],[ZB271;G6,Br,H,H,-],[ZB272;G6,CN,H,H,-],[ZB273;G6,H,Me,H,-],[ZB274;G6,H,Et,H,-],[ZB275;G6,H,Pr,H,-],[ZB276;G6,H,i-Pr,H,-],[ZB277;G6,H,c-Pr,H,-],[ZB278;G6,H,Ph,H,-],[ZB279;G6,H,OMe,H,-],[ZB280;G6,H,OEt,H,-],[ZB281;G6,H,OPh,H,-],[ZB282;G6,H,CF3,H,-],[ZB283;G6,H,F,H,-],[ZB284;G6,H,Cl,H,-],[ZB285;G6,H,Br,H,-],[ZB286;G6,H,CN,H,-],[ZB287;G6,H,H,Me,-],[ZB288;G6,H,H,Et,-],[ZB289;G6,H,H,Pr,-],[ZB290;G6,H,H,i-Pr,-],[ZB291;G6,H,H,c-Pr,-],[ZB292;G6,H,H,Ph,-],[ZB293;G6,H,H,OMe,-],[ZB294;G6,H,H,OEt,-],[ZB295;G6,H,H,OPh,-],[ZB296;G6,H,H,CF3,-],[ZB297;G6,H,H,F,-],[ZB298;G 6,H,H,Cl,-],[ZB299;G6,H,H,Br,-],[ZB300;G6,H,H,CN,-],[ZB301;G7,H ,H,H,-],[ZB302;G7,Me,H,H,-],[ZB303;G7,Et,H,H,-],[ZB304;G7,Pr,H ,H,-],[ZB305;G7,i-Pr,H,H,-],[ZB306;G7,c-Pr,H,H,-],[ZB307;G7,Ph, H,H,-],[ZB308;G7,OMe,H,H,-],[ZB309;G7,OEt,H,H,-],[ZB310;G7,OPh ,H,H,-],[ZB311;G7,CF3,H,H,-],[ZB312;G7,F,H,H,-],[ZB313;G7,Cl,H, H,-],[ZB314;G7,Br,H,H,-],[ZB315;G7,CN,H,H,-],[ZB316;G7,H,Me,H, -],[ZB317;G7,H,Et,H,-],[ZB318;G7,H,Pr,H,-],[ZB319;G7,H,i-Pr,H,- ],[ZB320;G7,H,c-Pr,H,-],[ZB321;G7,H,Ph,H,-],[ZB322;G7,H,OMe,H, -],[ZB323;G7,H,OEt,H,-],[ZB324;G7,H,OPh,H,-],[ZB325;G7,H,CF3,H, -],[ZB326;G7,H,F,H,-],[ZB327;G7,H,Cl,H,-],[ZB328;G7,H,Br,H,-], [ZB329;G7,H,CN,H,-],[ZB330;G7,H,H,Me,-],[ZB331;G7,H,H,Et,-],[ZB 332;G7,H,H,Pr,-],[ZB333;G7,H,H,i-Pr,-],[ZB334;G7,H,H,c-Pr,-],[ ZB335;G7,H,H,Ph,-],[ZB336;G7,H,H,OMe,-],[ZB337;G7,H,H,OEt,-],[Z B338;G7,H,H,OPh,-],[ZB339;G7,H,H,CF3,-],[ZB340;G7,H,H,F,-],[ZB3 41;G7,H,H,Cl,-],[ZB342;G7,H,H,Br,-],[ZB343;G7,H,H,CN,-],[ZB344;G8,H,H,H,-],[ZB345;G8,Me,H,H,-],[ZB346;G8,Et,H,H,-],[ZB347;G8,Pr,H,H,-],[ZB348;G8,i-Pr,H,H,-],[ZB349;G8,c-Pr,H,H,-],[ZB350;G8,Ph,H,H,-],[ZB351;G8,OMe,H,H,-],[ZB352;G8,OEt,H,H,-],[ZB353;G8,OPh,H,H,-],[ZB354;G8,CF3,H,H,-],[ZB355;G8,F,H,H,-],[ZB356;G8,Cl,H,H,-],[ZB357;G8,Br,H,H,-],[ZB358;G8,CN,H,H,-],[ZB359;G8,H,Me,H,-],[ZB360;G8,H,Et,H,-],[ZB361;G8,H,Pr,H,-],[ZB362;G8,H,i-Pr,H,-],[ZB363;G8,H,c-Pr,H,-],[ZB364;G8,H,Ph,H,-],[ZB365;G8,H,OMe,H,-],[ZB366;G8,H,OEt,H,-],[ZB367;G8,H,OPh,H,-],[ZB368;G8,H,CF3,H,-],[ZB369;G8,H,F,H,-],[ZB370;G8,H,Cl,H,-],[ZB371;G8,H,Br,H,-],[ZB372;G8,H,CN,H,-],[ZB373;G8,H,H,Me,-],[ZB374;G8,H,H,Et,-],[ZB375;G8,H,H,Pr,-],[ZB376;G8,H,H,i-Pr,-],[ZB377;G8,H,H,c-Pr,-],[ZB378;G8,H,H,Ph,-],[ZB379;G8,H,H,OMe,-],[ZB380;G8,H,H,OEt,-],[ZB381;G8,H,H,OPh,-],[ZB382;G8,H,H,CF3,-],[ZB383;G8,H,H,F,-],[ZB384;G8,H,H,Cl,-],[ZB385;G8,H,H,Br,-],[ZB386;G8,H,H,CN,-],[ZB387;G9,H,H,H,-],[ZB388;G9,Me,H,H,-],[ZB389;G9,Et,H,H,-],[ZB390;G9,Pr,H,H,-],[ZB391;G9,i-Pr,H,H,-],[ZB392;G9,c-Pr,H,H,-],[ZB393;G9,Ph,H,H,-],[ZB394;G9,OMe,H,H,-],[ZB395;G9,OEt,H,H,-],[ZB396;G9,OPh,H,H,-],[ZB397;G9,CF3,H,H,-],[ZB398;G9,F,H,H,-],[ZB399;G9,Cl,H,H,-],[ZB400;G9,Br,H,H,-],[ZB401;G9,CN,H,H,-],[ZB402;G9,H,Me,H,-],[ZB403;G9,H,Et,H,-],[ZB404;G9,H,Pr,H,-],[ZB405;G9,H,i-Pr,H,-],[ZB406;G9,H,c-Pr,H,-],[ZB407;G9,H,Ph,H,-],[ZB408;G9,H,OMe,H,-],[ZB409;G9,H,OEt,H,-],[ZB410;G9,H,OPh,H,-],[ZB411;G9,H,CF3,H,-],[ZB412;G9,H,F,H,-],[ZB413;G9,H,Cl,H,-],[ZB414;G9,H,Br,H,-],[ZB415;G9,H,CN,H,-],[ZB416;G9,H,H,Me,-],[ZB417;G9,H,H,Et,-],[ZB418;G9,H,H,Pr,-],[ZB419;G9,H,H,i-Pr,-],[ZB420;G9,H,H,c-Pr,-],[ZB421;G9,H,H,Ph,-],[ZB422;G9,H,H,OMe,-],[ZB423;G9,H,H,OEt,-],[ZB424;G9,H,H,OPh,-],[ZB425;G9,H,H,CF3,-],[ZB426;G9,H,H,F,-],[ZB427;G9,H,H,Cl,-],[ZB428;G9,H,H,Br,-],[ZB429;G9,H,H,CN,-],[ZB430;G10,H,H,H,-],[ZB431;G10,Me,H,H,-],[ZB432;G10,Et,H,H,-],[ZB433;G10,Pr,H,H,-],[ZB434;G10,i-Pr,H,H,-],[ZB435;G10,c-Pr,H,H,-],[ZB436;G10,Ph,H,H,-],[ZB437;G10,OMe,H,H,-],[ZB438;G10,OEt,H,H,-],[ZB439;G10,OPh,H,H,-],[ZB440;G10,CF3,H,H,-],[ZB441;G10,F,H,H,-],[ZB442;G10,Cl,H,H,-],[ZB443;G10,Br,H,H,-],[ZB444;G10,CN,H,H,-],[ZB445;G10,H,Me,H,-],[ZB446;G10,H,Et,H,-],[ZB447;G10,H,Pr,H,-],[ZB448;G10,H,i-Pr,H,-],[ZB449;G10,H,c-Pr,H,-],[ZB450;G10,H,Ph,H,-],[ZB451;G10,H,OMe,H,-],[ZB452;G10,H,OEt,H,-],[ZB453;G10,H,OPh,H,-],[ZB454;G10,H,CF3,H,-],[ZB455;G10,H,F,H,-],[ZB456;G10,H,Cl,H,-],[ZB457;G10,H,Br,H,-],[ZB458;G10,H,CN,H,-],[ZB459;G10,H,H,Me,-],[ZB460;G10,H,H,Et,-],[ZB461;G10,H,H,Pr,-],[ZB462;G10,H,H,i-Pr,-],[ZB463;G10,H,H,c-Pr,-],[ZB464;G10,H,H,Ph,-],[ZB465;G10,H,H,OMe,-],[ZB466;G10,H,H,OEt,-],[ZB467;G10,H,H,OPh,-],[ZB468;G10,H,H,CF3,-],[ZB469;G10,H,H,F,-],[ZB470;G10,H,H,Cl,-],[ZB471;G10,H,H,Br,-],[ZB472;G10,H,H,CN,-],[ZB473;G11,H,H,H,-],[ZB474;G11,H,Me,H,-],[ZB475;G11,H,Et,H,-],[ZB476;G11,H,Pr,H,-],; 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;G12,c-Pen,H,H,-],[ZB1336;G12,c-Hex,H,H,-],[ZB1337;G12,1-Me-(c-Pr),H,H,-],[ZB1338;G12,1-F-(c-Pr),H,H,-],[ZB1339;G12,2,2-F2-(c-Pr),H,H,-],[ZB1340;G12,I,H,H,-],[ZB1341;G12,CH2CN,H,H,-],[ZB1342;G12,CH2OMe,H,H,-],[ZB1343;G12,CH2SMe,H,H,-],[ZB1344;G12,c-hexen-1-yl,H,H,-],[ZB1345;G12,OPr,H,H,-],[ZB1346;G12,O(i-Pr),H,H,-],[ZB1347;G12,OCHF2,H,H,-],[ZB1348;G12,SCF3,H,H,-],[ZB1349;G12,C(Me)=NOMe,H,H,-],[ZB1350;G12,H,t-Bu,H,-],[ZB1351;G12,H,c-Bu,H,-],[ZB1352;G12,H,c-Pen,H,-],[ZB1353;G12,H,CCH,H,-],[ZB1354;G12,H,CH2OMe,H,-],[ZB1355;G12,H,I,H,-],[ZB1356;G12,H,S(i-Pr),H,-],[ZB1357;G12,Me,Me,H,-],[ZB1358;G12,Pr,Me,H,-],[ZB1359;G12,i-Pr,Me,H,-],[ZB1360;G12,CHF2,Me,H,-],[ZB1361;G12,CF3,Me,H,-],[ZB1362;G12,c-Pr,Me,H,-],[ZB1363;G12,c-Hex,Me,H,-],[ZB1364;G12,OMe,Me,H,-],[ZB1365;G12,O(i-Pr),Me,H,-],[ZB1366;G12,F,Me,H,-],[ZB1367;G12,Cl,Me,H,-],[ZB1368;G12,Br,Me,H,-],[ZB1369;G12,i-Pr,F,H,-],[ZB1370;G12,Me,F,H,-],[ZB1371;G12,Pr,F,H,-],[ZB1372;G12,CHF2,F,H,-],[ZB1373;G12,CF3,F,H,-],[ZB1374;G12,c-Pr,F,H,-],[ZB1375;G12,c-Hex,F,H,-],[ZB1376;G12,OMe,F,H,-],[ZB1377;G12,O(i-Pr),F,H,-],[ZB1378;G12,F,F,H,-],[ZB1379;G12,Cl,F,H,-],[ZB1380;G12,Br,F,H,-],[ZB1381;G12,Pr,Cl,H,-],[ZB1382;G12,i-Pr,Cl,H,-],[ZB1383;G12,c-Hex,Cl,H,-],[ZB1384;G12,Cl,Cl,H,-],[ZB1385;G12,O(i-Pr),Cl,H,-],[ZB1386;G12,Me,Cl,H,-],[ZB1387;G12,CHF2,Cl,H,-],[ZB1388;G12,CF3,Cl,H,-],[ZB1389;G12,c-Pr,Cl,H,-],[ZB1390;G12,OMe,Cl,H,-],[ZB1391;G12,F,Cl,H,-],[ZB1392;G12,Br,Cl,H,-],[ZB1393;G12,Me,Br,H,-],[ZB1394;G12,c-Hex,Br,H,-],[ZB1395;G12,Pr,Br,H,-],[ZB1396;G12,i-Pr,Br,H,-],[ZB1397;G12,CHF2,Br,H,-],[ZB1398;G12,CF3,Br,H,-],[ZB1399;G12,c-Pr,Br,H,-],[ZB1400;G12,OMe,Br,H,-],[ZB1401;G12,O(i-Pr),Br,H,-],[ZB1402;G12,F,Br,H,-],[ZB1403;G12,Cl,Br,H,-],[ZB1404;G12,Br,Br,H,-],[ZB1405;G22,H,Bu,-,-],[ZB1406;G22,H,CH2(i-Pr),-,-],[ZB1407;G22,H,c-Bu,-,-],[ZB1408;G22,H,c-Pen,-,-],[ZB1409;G22,H,c-Hex,-,-],[ZB1410;G22,H,c-hexen-1-yl,-,-],[ZB1411;G22,H,CHF2,-,-],[ZB1412;G22,H,CF2CF3,-,-],[ZB1413;G22,H,CH=CH2,-,-],[ZB1414;G22,H,C(Me)=CH2,-,-],[ZB1415;G22,H,CC(c-Pr),-,-],[ZB1416;G22,H,CC(i-Pr),-,-],[ZB1417;G22,H,CC(Me),-,-],[ZB1418;G22,H,CH=NOMe,-,-],[ZB1419;G22,H,C(Me)=NOMe,-,-],[ZB1420;G22,H,CH2O(i-Pr),-,-],[ZB1421;G22,H,CH2OEt,-,-],[ZB1422;G22,H,CH2OPh,-,-],[ZB1423;G22,Me,H,-,-],[ZB1424;G22,Et,H,-,-],[ZB1425;G22,Pr,H,-,-],[ZB1426;G22,Bu,H,-,-],[ZB1427;G22,CH2(i-Pr),H,-,-],[ZB1428;G22,c-Bu,H,-,-],[ZB1429;G22,c-Pen,H,-,-],[ZB1430;G22,c-Hex,H,-,-],[ZB1431;G22,c-hexen-1-yl,H,-,-],[ZB1432;G22,CHF2,H,-,-],[ZB1433;G22,CF2CF3,H,-,-],[ZB1434;G22,CN,H,-,-],[ZB1435;G22,OMe,H,-,-],[ZB1436;G22,CH=CH2,H,-,-],[ZB1437;G22,C(Me)=CH2,H,-,-],[ZB1438;G22,CC(c-Pr),H,-,-],[ZB1439;G22,CC(i-Pr),H,-,-],[ZB1440;G22,CC(Me),H,-,-],[ZB1441;G22,CH=NOMe,H,-,-],[ZB1442;G22,C(Me)=NOMe,H,-,-],[ZB1443;G22,CH2O(i-Pr),H,-,-],[ZB1444;G22,CH2OEt,H,-,-],[ZB1445;G22,CH2OPh,H,-,-],[ZB1446;G22,Me,Me,-,-],[ZB1447;G22,Me,Et,-,-],[ZB1448;G22,Me,i-Pr,-,-],[ZB1449;G22,Me,c-Pr,-,-],[ZB1450;G22,Me,c-Hex,-,-],[ZB1451;G22,Me,CHF2,-,-],[ZB1452;G22,Me,CF3,-,-],[ZB1453;G22,Me,F,-,-],[ZB1454;G22,Me,Cl,-,-],[ZB1455;G22,Me,Br,-,-],[ZB1456;G22,Cl,Me,-,-],[ZB1457;G22,Cl,Et,-,-],[ZB1458;G22,Cl,i-Pr,-,-],[ZB1459;G22,Cl,c-Pr,-,-],[ZB1460;G22,Cl,c-Hex,-,-],[ZB1461;G22,Cl,CHF2,-,-],[ZB1462;G22,Cl,CF3,-,-],[ZB1463;G22,Cl,F,-,-],[ZB1464;G22,Cl,Cl,-,-],[ZB1465;G22,Cl,Br,-,-],[ZB1466;G22,F,Me,-,-],[ZB1467;G22,F,Et,-,-],[ZB1468;G22,F,i-Pr,-,-],[ZB1469;G22,F,c-Pr,-,-],[ZB1470;G22,F,c-Hex,-,-],[ZB1471;G22,F,CHF2,-,-],[ZB1472;G22,F,CF3,-,-],[ZB1473;G22,F,F,-,-],[ZB1474;G22,F,Cl,-,-],[ZB1475;G22,F,Br,-,-],[ZB1476;G35,Me,H,-,-],[ZB1477;G35,Et,H,-,-],[ZB1478;G35,Pr,H,-,-],[ZB1479;G35,Bu,H,-,-],[ZB1480;G35,i-Pr,H,-,-],[ZB1481;G35,C(Me)=CH2,H,-,-],[ZB1482;G35,CHF2,H,-,-],[ZB1483;G35,CF3,H,-,-],[ZB1484;G35,c-Pr,H,-,-],[ZB1485;G35,c-Pen,H,-,-],[ZB1486;G35,c-Hex,H,-,-],[ZB1487;G35,C(Me)=NOH,H,-,-],[ZB1488;G35,C(Me)=NOEt,H,-,-],[ZB1489;G35,F,H,-,-],[ZB1490;G35,Cl,H,-,-],[ZB1491;G35,Br,H,-,-],[ZB1492;G35,Me,Cl,-,-],[ZB1493;G35,Et,Cl,-,-],[ZB1494;G35,Pr,Cl,-,-],[ZB1495;G35,Bu,Cl,-,-],[ZB1496;G35,i-Pr,Cl,-,-],[ZB1497;G35,C(Me)=CH2,Cl,-,-],[ZB1498;G35,CHF2,Cl,-,-],[ZB1499;G35,CF3,Cl,-,-],[ZB1500;G35,c-Pr,Cl,-,-],[ZB1501;G35,c-Pen,Cl,-,-],[ZB1502;G35,c-Hex,Cl,-,-],[ZB1503;G35,C(Me)=NOH,Cl,-,-],[ZB1504;G35,C(Me)=NOEt,Cl,-,-],[ZB1505;G35,F,Cl,-,-],[ZB1506;G35,Cl,Cl,-,-],[ZB1507;G35,Br,Cl,-,-],[ZB1508;G35,Me,Br,-,-],[ZB1509;G35,Et,Br,-,-],[ZB1510;G35,Pr,Br,-,-],[ZB1511;G35,Bu,Br,-,-],[ZB1512;G35,i-Pr,Br,-,-],[ZB1513;G35,C(Me)=CH2,Br,-,-],[ZB1514;G35,CHF2,Br,-,-],[ZB1515;G35,CF3,Br,-,-],[ZB1516;G35,c-Pr,Br,-,-],[ZB1517;G35,c-Pen,Br,-,-],[ZB1518;G35,c-Hex,Br,-,-],[ZB1519;G35,C(Me)=NOH,Br,-,-],[ZB1520;G35,C(Me)=NOEt,Br,-,-],[ZB1521;G35,F,Br,-,-],[ZB1522;G35,Cl,Br,-,-],[ZB1523;G35,Br,Br,-,-],[ZB1524;G35,Me,Me,-,-],[ZB1525;G35,Et,Me,-,-],[ZB1526;G35,Pr,Me,-,-],[ZB1527;G35,Bu,Me,-,-],[ZB1528;G35,i-Pr,Me,-,-],[ZB1529;G35,C(Me)=CH2,Me,-,-],[ZB1530;G35,CHF2,Me,-,-],[ZB1531;G35,CF3,Me,-,-],[ZB1532;G35,c-Pr,Me,-,-],[ZB1533;G35,c-Pen,Me,-,-],[ZB1534;G35,c-Hex,Me,-,-],[ZB1535;G35,C(Me)=NOH,Me,-,-],[ZB1536;G35,C(Me)=NOEt,Me,; -,-],[ZB1537;G35,F,Me,-,-],[ZB1538;G35,Cl,Me,-,-],[ZB1539;G35,Br,Me,-,-]

[0176] In compound (1J), Q is Q1 and R 1 is a chlorine atom, and the structure of G and the R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX137). In compound (1J), Q is Q1 and R 1 is a fluorine atom, and the structure of G and R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX138). In compound (1J), Q is Q1 and R 1 is an ethyl group, and the structure of G and the R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX139). In compound (1J), Q is Q1 and R 1 is a cyclopropyl group, and the structure of G and R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX140). In compound (1J), Q is Q2, L is an oxygen atom, and R 1is a methyl group, and the structure of G and the R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX141). In compound (1J), Q is Q2, L is an oxygen atom, and R 1 is a chlorine atom, and the structure of G and the R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX142). In compound (1J), Q is Q2, L is NH, and R 1 is a methyl group, and the structure of G and the R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX143). In compound (1J), Q is Q2, L is NH, and R 1 is a chlorine atom, and the structure of G and the R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX144).

[0177] Formula (1K): [ka] In the compound represented by the formula (hereinafter referred to as compound (1K)), Q is Q1, and R 1 is a methyl group, and R X11 , R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 and R X19is any one of the combinations described in Combination C (hereinafter referred to as compound group SX145).

[0178] The combination C consists of substituent numbers ZC1 to ZC30. The substituent numbers ZC1 to ZC30 are the R X11 , R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 and R X19 The following represents a combination of [substituent number; R X11 ,R X12 ,R X13 ,R X14 ,R X15 ,R X16 ,R X17 ,R X18 ,R X19 For example, the substituent number ZC2 is R X11 is a methyl group, and R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 and R X19 is a hydrogen atom.

[0179] Combination C: [ZC1; H, H, H, H, H, H, H, H, H], [ZC2; Me, H, H, H, H, H, H, H], [ZC3; F, H, H, H, H, H, H, H], [ZC4; Cl, H, H, H, H, H, H, H], [ZC5; H, F, F, H, H, H, H, H], [ZC6; Me, F, F, H, H, H, H, H], [ZC7; F, F, F, H, H, H, H, H], [ZC8; Cl, F, F, H, H, H, H, H], [ZC9; H, H, H, H, H, H, H, F, F], [ZC10; Me, H, H, H, H, H, H, F, F], [ZC11; F, H, H, H, H, H, H, F, F], [ZC12; Cl, H, H, H, H, H, H, F, F], [ZC13; H, Cl, Cl, H, H, H, H, H], [ZC14; Me, Cl, Cl, H, H, H, H, H], [ZC15; F, Cl, Cl, H, H, H, H, H], [ZC16; Cl, Cl, Cl, H, H, H, H, H], [ZC17; H, H, H, H, H, H, H, Cl, Cl], [ZC18; Me, H, H, H, H, H, H, Cl, Cl], [ZC19; F, H, H, H, H, H, H, Cl, Cl], [ZC20; Cl, H, H, H, H, H, H, Cl, Cl], [ZC21; H, H, H, F, F, H, H, H], [ZC22; H, H, H, Me, Me, H, H, H], [ZC23; H, H, H, Cl, Cl, H, H, H], [ZC24; H, H, H, i-Pr, H, H, H, H], [ZC25; H, H, H, CHF2, H, H, H, H],...

Claims

1. Formula (I): 【Chemistry 1】 [During the ceremony, Q represents a group represented by Q1 or a group represented by Q2 (● represents a bonding site to a benzene ring); 【Chemistry 2】 E is R 7 -C≡C-, a phenyl group, a pyridyl group, a thienyl group, a furanyl group, a thiadiazolyl group, a pyrazolyl group {the phenyl group, the pyridyl group, the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are optionally substituted with one or more substituents selected from group J}, or a pyrimidinyl group {the pyrimidinyl group is optionally substituted with one or more substituents selected from group K}, L represents an oxygen atom or NH; R 1 and the combination of n is R 1 is a hydrogen atom and n is 1; or R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a methoxy group, a cyclopropyl group, or a halogen atom, and n is 0; R 2 represents a methyl group, a cyclopropyl group, or a halogen atom; R 7 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a cyclopropyl group. Group F: a group consisting of a C3-C4 cycloalkyl group, a C1-C3 alkoxy group, and a halogen atom. Group G: a group consisting of a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, a halogen atom, and a cyano group. Group J: a group consisting of C1-C6 chain hydrocarbon groups, C1-C3 alkoxy groups {the C1-C6 chain hydrocarbon groups and the C1-C3 alkoxy groups may be substituted with one or more substituents selected from group F}, a cyclopropyl group, a halogen atom, a cyano group, C(R 4 )═N—OR 11 , a phenyl group, a pyridyl group, and a pyrazolyl group {the phenyl group, the pyridyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group G}. R 4 represents a C1-C3 alkyl group or a hydrogen atom; R 11 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, or a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms. Group K: a group consisting of a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenoxy group which may be substituted with one or more substituents selected from Group G, and a halogen atom. or an N-oxide or an agriculturally acceptable salt thereof.

2. R 1 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom; n is 0; 2. A compound according to claim 1, or an N-oxide or an agriculturally acceptable salt thereof.

3. Q is a group represented by Q1, R 1 is a methyl group, n is 0; 2. A compound according to claim 1, or an N-oxide or an agriculturally acceptable salt thereof.

4. 4. An agricultural chemical composition comprising a compound according to any one of claims 1 to 3, or an N-oxide or an agriculturally acceptable salt thereof, and an inert carrier.

5. A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and a compound according to any one of claims 1 to 3, or an N-oxide or an agriculturally acceptable salt thereof: Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): repellent components.

6. A method for controlling pests, which comprises applying to plants or soil an effective amount of the compound according to any one of claims 1 to 3, or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to claim 5.

7. A method for controlling soybean rust fungus having an amino acid substitution of F129L in mitochondrial cytochrome b protein, comprising applying an effective amount of the compound according to any one of claims 1 to 3, or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to claim 5 to soybeans or soil in which soybeans are grown.

8. Use of a compound according to any one of claims 1 to 3, or an N-oxide or an agriculturally acceptable salt thereof, or a composition according to claim 5, for controlling pests.

9. A seed or vegetative reproductive organ carrying an effective amount of a compound according to any one of claims 1 to 3, or an N-oxide or an agriculturally acceptable salt thereof, or a composition according to claim 5.

10. Formula (II): 【Chemistry 3】 [During the ceremony, Q and E Ｂ The combination of Q is a group represented by Q1, Ｂ But, R 12 C(O)-, R 12 C(=N-OH)-, or a halogen atom; or Q is a group represented by Q2, Ｂ But, R 12 C(O)-, R 12 C(═N—OH)—, a bromine atom, or an iodine atom; A group represented by Q1 and a group represented by Q2 each represent a group represented by the following formula (● represents a bonding site to a benzene ring): 【Chemistry 4】 L represents an oxygen atom or NH; R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a methoxy group, a cyclopropyl group, or a halogen atom; R 12 represents a C1-C3 alkyl group. A compound represented by the formula:

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