Phenyl compound and method for controlling plant diseases

Abstract

The present invention provides a control method effective against plant diseases. In the present invention, compounds represented by Formula (I) (wherein Z represents a C1-C6 chain hydrocarbon group or the like, Q represents a group represented by Q1, a group represented by Q2, or a group represented by Q3 (wherein # represents a binding site to the phenyl group, and · represents a binding site to the sulfur atom), Q1, Q2, Q3, R1, R2, R3, R4, and R5 are the same or different and represent a C1-C6 chain hydrocarbon group or the like, R6, R7, R8, and R9 are the same or different and represent a hydrogen atom or the like, and n represents 0, 1 or 2) can be used to control plant diseases.

Description

Technical Field

[0001] This application claims priority and the benefit thereof to Japanese Patent Application No. 2020-075879 filed on April 22, 2020, the entire contents of which are incorporated herein by reference. The present invention relates to a phenyl compound and a method for controlling plant diseases.

Background Art

[0002] Patent Document 1 describes phenylpyrazole compounds for use as insecticides, acaricides and nematicides.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present invention is to provide an excellent method for controlling plant diseases.

Means for Solving the Problems

[0005] As a result of investigations to find an excellent method for controlling plant diseases, the present inventors have found that the compound represented by the following formula (I) has excellent control efficacy against plant diseases. That is, the present invention is as follows.

[0006] 〔1〕 Formula (I):

Chemical Formula

Chemical formula

Chemical formula

Chemical formula

[10] or its N-oxide or a salt thereof. A method for controlling plant diseases by treating an effective amount of the compound according to any one of [6] to

[10] , or its N-oxide or salts thereof, on a plant or the soil in which the plant is cultivated. 〔13〕 Use of the compound according to any one of [6] to

[10] , or its N-oxide or salts thereof, for controlling plant diseases. 〔14〕 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 [6] to

[10] , or its N-oxide or salts thereof: Group (a): The group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): Fungicidal active ingredients; Group (c): Plant growth regulating ingredients; Group (d): Repellent ingredients. 〔15〕 Seeds or vegetative reproductive organs holding an effective amount of the compound represented by formula (I) according to any one of [1] to [5], or its N-oxide or salts thereof, the compound according to any one of [6] to

[10] , or its N-oxide or salts thereof, or the composition according to

[14] . 〔16〕 Formula (III):

Chemical formula

Advantages of the Invention

[0007] According to the present invention, plant diseases can be controlled.

Modes for Carrying Out the Invention

[0008] The substituents in the present invention will be described. The halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When the substituent is substituted with two or more halogen atoms or groups, those halogen atoms or groups may be the same or different from each other. The notation "CY-CW" in this specification means that the number of carbon atoms is from Y to W. For example, the notation "C1-C6" means that the number of carbon atoms is from 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 3-butenyl group, a 4-pentenyl group, and a 5-hexenyl group. 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, and a 5-hexynyl group.

[0009] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0010] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group. Examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group. Examples of the alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group. Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.

[0011] Examples of the aryl group include a phenyl group, an indenyl group, an indanyl group, a naphthyl group, and a tetrahydronaphthyl group. Examples of the 5- to 10-membered aromatic heterocyclic group include a 5-membered aromatic heterocyclic group, a 6-membered aromatic heterocyclic group, a 9-membered aromatic heterocyclic group, and a 10-membered aromatic heterocyclic group. Examples of the 5-membered aromatic heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, and a thiadiazolyl group. Examples of the 6-membered aromatic heterocyclic group include a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, and a tetrazinyl group. Examples of the 9-membered aromatic heterocyclic group include an indolyl group, an indazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzothiophenyl group, and a benzofuranyl group. Examples of the 10-membered aromatic heterocyclic group include a quinolyl group, an isoquinolyl group, a quinazolinyl group, and a quinoxalinyl group.

[0012] Examples of the C4-C7 carbocyclic ring include a cyclobutene ring, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, a benzene ring, and a cycloheptene ring. Examples of the 5- to 7-membered heterocycle include a furan ring, a dihydrofuran ring, a thiophene ring, a dihydrothiophene ring, a pyrrole ring, a dihydropyrrole ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a 1,3-dioxole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyran ring, and a dihydropyran ring.

[0013] In this specification, "R 1A , R 2A , R 3A , R 4A and R 5A At least one of is not a hydrogen atom" is replaced with "R 1A , R 2A , R 3A , R 4A and R 5A is a hydrogen atom."

[0014] The compound, the compound of the present invention, and intermediate A may have one or more stereoisomers. The stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0015] The present compound or the compound of the present invention may form an acid addition salt such as a hydrochloride, a sulfate, a nitrate, a phosphate, an acetate or a benzoate by mixing with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid.

[0016] The embodiments of the present compound N include the following compounds.

[0017] [Aspect 1] In the compound N, R 1 , R 2 , R 3 , R 4 and R 5is the same or different and is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, a hydrogen atom, a halogen atom, -OR 10 , -C(O)NR 20 R 21 , -NR 22 C(O)R 23 , -C(O)N(OR 24 )R 25 , -N(OR 26 )C(O)R 27 , or -NR 33 C(O)OR 34 is a compound. 〔Aspect 2〕In this compound N, R 2 , R 3 , and R 4 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, a hydrogen atom, a halogen atom, -OR 10 , -C(O)NR 20 R 21 , -NR 22 C(O)R 23 , -C(O)N(OR 24 )R 25 , -N(OR 26 )C(O)R 27 , or -NR 33 C(O)OR 34 wherein R 1 and R 5 are the same or different and are a hydrogen atom or a halogen atom. 〔Aspect 3〕In this compound N, R 1 and R 5 are the same or different and are a hydrogen atom or a halogen atom, and R 2 and R 4 are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10 , or -NR 33 C(O)OR 34 wherein R 3is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a hydrogen atom, a halogen atom, -OR which may be substituted with one or more halogen atoms 10 , or -NR 33 C(O)OR 34 and is a compound [Aspect 4] In Aspect 1, R 10 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10 membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group F {the 5-10 membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms}, R 20 , R 21 , R 22 , R 24 , and R 26 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 23 , R 25 , and R 27 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from Group G}, R 33 is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, R 34 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms and is a compound Group F: a group consisting of a C6-C10 aryl group which may be substituted with one or more substituents selected from Group G, and a halogen atom Group G: a group consisting of a C1-C3 alkoxy group, a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group [Aspect 5] In Aspect 1, R 10 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10 membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group F {the 5-10 membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms}, R 20 , R 21 , R22 , R 24 , and R 26 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, and R 23 , R 25 , and R 27 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}, and R 33 is a hydrogen atom, and R 34 is a C1-C3 chain hydrocarbon group. [Aspect 6] In aspect 3, R 10 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms} which may be substituted with one or more substituents selected from group F, and R 20 , R 21 , R 22 , R 24 , and R 26 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, and R 23 , R 25 , and R 27 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}, and R 33 is a hydrogen atom, and R 34 is a C1-C3 chain hydrocarbon group. [Aspect 7] In this compound N, R 1 and R 5 are each a hydrogen atom, and R 2 and R 4 are the same or different and are a hydrogen atom or a halogen atom, and R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms or a halogen atom. 〔Aspect 8〕A compound in which, in the present compound N, Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from Group A. 〔Aspect 9〕A compound in which, in the present compound N, Z is a C1-C6 chain hydrocarbon group or a pyridyl group. 〔Aspect 10〕A compound in which, in the present compound N, Z is a C1-C6 chain hydrocarbon group. 〔Aspect 11〕In Aspect 4, a compound in which Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from Group A. 〔Aspect 12〕In Aspect 4, a compound in which Z is a C1-C6 chain hydrocarbon group or a pyridyl group. 〔Aspect 13〕In Aspect 4, a compound in which Z is a C1-C6 chain hydrocarbon group. 〔Aspect 14〕In Aspect 6, a compound in which Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from Group A. 〔Aspect 15〕In Aspect 6, a compound in which Z is a C1-C6 chain hydrocarbon group or a pyridyl group. 〔Aspect 16〕In Aspect 6, a compound in which Z is a C1-C6 chain hydrocarbon group. 〔Aspect 17〕In Aspect 7, a compound in which Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from Group A. 〔Aspect 18〕In Aspect 7, a compound in which Z is a C1-C6 chain hydrocarbon group or a pyridyl group. 〔Aspect 19〕A compound in which, in the present compound N, n is 1 or 2. 〔Aspect 20〕A compound in which, in the present compound N, n is 2. 〔Aspect 21〕In Aspect 15, a compound in which n is 2. 〔Aspect 22〕In Aspect 17, a compound in which n is 2. 〔Aspect 23〕In Aspect 18, a compound in which n is 2. 〔Aspect 24〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein Q is a group represented by Q1 or a group represented by Q2. 〔Aspect 25〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein Q is a group represented by Q1. 〔Aspect 26〕In any one of Aspects 1 to 23 or this Compound N, R 6 and R 7 are each a hydrogen atom. 〔Aspect 27〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein R 8 is a hydrogen atom. 〔Aspect 28〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein R 9 is a hydrogen atom. 〔Aspect 29〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein R 6 , R 7 , R 8 and R 9 are each a hydrogen atom. 〔Aspect 30〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein Q is a group represented by Q1 or a group represented by Q2, and R 6 , R 7 , and R 8 are each a hydrogen atom. 〔Aspect 31〕A compound in any one of Aspects 1 to 23 or this Compound N, wherein Q is a group represented by Q1, and R 6 and R 7 are each a hydrogen atom. 〔Aspect 32〕A compound in any one of Aspects 1 to 18 or this Compound N, wherein Q is a group represented by Q1 or a group represented by Q3, and n is 0 or 2. 〔Aspect 33〕A compound in any one of Aspects 1 to 18 or this Compound N, wherein Q is a group represented by Q3, and n is 2. 〔Aspect 34〕A compound in any one of Aspects 1 to 18 or this Compound N, wherein Q is a group represented by Q1 or a group represented by Q3, n is 0 or 2, and R 6 , R 7 and R 9 are each a hydrogen atom. 〔Aspect 35〕In any of Aspect 1 to Aspect 18 or this Compound N, Q is a group represented by Q3, n is 2, and R 9 is a hydrogen atom.

[0018] 〔Aspect 36〕In this Compound N, a compound in which Q is a group represented by Q1 or a group represented by Q2, and n is 0 or 2. 〔Aspect 37〕In this Compound N, a compound in which Q is a group represented by Q1 or a group represented by Q2, and n is 2. 〔Aspect 38〕In this Compound N, a compound in which Q is a group represented by Q1 or a group represented by Q3, and n is 2. 〔Aspect 39〕In this Compound N, a compound in which Q is a group represented by Q1, and n is 0 or 2. 〔Aspect 40〕In this Compound N, a compound in which Q is a group represented by Q3, and n is 2. 〔Aspect 41〕In any of Aspect 36 to Aspect 40 or this Compound N, a compound in which Z is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group E, or a C3-C6 cycloalkyl group. 〔Aspect 42〕In any of Aspect 36 to Aspect 40 or this Compound N, a compound in which Z is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from the group consisting of a methoxy group and a halogen atom}. 〔Aspect 43〕In Aspect 41, R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom, and R 10 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. 〔Aspect 44〕In Aspect 41, R 1 and R 5 are each a hydrogen atom, R 2 and R 4 are the same or different and are a hydrogen atom or a halogen atom, R3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom (provided that R 1 , R 2 , R 3 , R 4 and R 5 at least one of which is not a hydrogen atom). [Aspect 45] In Aspect 42, R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom, and R 10 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. [Aspect 46] In Aspect 42, R 1 and R 5 are each a hydrogen atom, R 2 and R 4 are the same or different and are a hydrogen atom or a halogen atom, and R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom (provided that R 1 , R 2 , R 3 , R 4 and R 5 at least one of which is not a hydrogen atom). [Aspect 47] In any of Aspects 36 to 40 or of this Compound N, Z is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 1 , R 2 , R 3 , R 4 and R 5 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, a hydrogen atom, a halogen atom, -OR 10 , or -NHC(O)OR 34 , and R 10is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F2, or a phenyl group optionally substituted with one or more substituents selected from group G, and R 34 is a C1-C6 chain hydrocarbon group. Group F2: A group consisting of a phenyl group optionally substituted with one or more substituents selected from group G, and a halogen atom.

[0019] Examples of the compound N of the present invention include the following compounds.

[0020] 〔Aspect A1〕In the compound N of the present invention, R 1A and R 5A are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22B C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33B C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom). 〔Aspect A2〕In the compound N of the present invention, R 1A and R 5A are the same or different and are a hydrogen atom or a fluorine atom (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom). 〔Aspect A3〕In the compound N of the present invention, R 1A and R 5A are each a hydrogen atom (provided that at least one of R 1A , R 2A , R 3A , R4A and R 5A wherein at least one of them is not a hydrogen atom). [Aspect A4] In the compound N of the present invention, R 2A and R 4A are the same or different and may be a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom). [Aspect A5] In the compound N of the present invention, R 2A and R 4A are the same or different and may be a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom). [Aspect A6] In the compound N of the present invention, R 3A is a C1-C6 linear hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 linear hydrocarbon group and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms}, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A, -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom) is a compound. [Aspect A7] In the compound N of the present invention, R 3A is a C3-C6 cycloalkyl group, a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom) is a compound. [Aspect A8] In the compound N of the present invention, R 1A and R 5A are the same or different and are a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22B C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33B C(O)OR 34A , and R 2A and R 4A are the same or different and are a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A)C(O)R 27A 、 or -NR 33A C(O)OR 34A wherein R 3A is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom). 〔Aspect A9〕In the compound N of the present invention, R 1A and R 5A are the same or different and are a hydrogen atom or a fluorine atom, and R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A wherein R 3A is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, -OR 10A , -C(O)NR 20A R 21A , -NR22A C(O)R 23A 、 -C(O)N(OR 24A )R 25A 、 -N(OR 26A )C(O)R 27A 、 or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom). A compound. [Aspect A10] In the compound N of the present invention, R 1A and R 5A are the same or different and are a hydrogen atom or a fluorine atom, R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A , and R 3A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom). A compound. [Aspect A11] In the compound N of the present invention, R 1A and R 5A are each a hydrogen atom, R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A , and R 3Ais a C3-C6 cycloalkyl group, a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A or -NR 33A C(O)OR 34A (provided that at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom) is a compound. 〔Aspect A12〕In the compound N of the present invention, R 1A and R 5A are each a hydrogen atom, R 2A and R 4A are the same or different and are a hydrogen atom or a halogen atom, and R 3A is a C1-C6 linear hydrocarbon group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom (provided that at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom) is a compound. 〔Aspect A13〕In Aspect A8, R 10A is a C3-C6 cycloalkyl group, a C1-C6 linear hydrocarbon group optionally substituted with one or more substituents selected from Group F A , or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may be substituted with a linear hydrocarbon group optionally substituted with one or more halogen atoms}, R 20A , R 21A , R 22A , R 24A , and R 26A are the same or different and are a C1-C6 linear hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 22B is a C1-C6 linear hydrocarbon group or a C3-C6 cycloalkyl group, and R 23A , R 23B , R 25A , and R 27A are the same or different and are a C1-C6 linear hydrocarbon group, a C3-C6 cycloalkyl group, or Group G AA phenyl group which may be substituted with one or more substituents selected from R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, and R 33B is a C1-C6 chain hydrocarbon group or a cyclopropyl group, and R 34A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. A compound. Group F A : Group G A A group consisting of a C6-C10 aryl group which may be substituted with one or more substituents selected from or a halogen atom. Group G A : A group consisting of a C1-C3 alkoxy group, a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group. 〔Aspect A14〕In Aspect A9, R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F A or a 5- to 10-membered aromatic heterocyclic group {the 5- to 10-membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms}, and R 20A , R 21A , R 22A , R 24A , and R 26A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, and R 23A , R 23B , R 25A , and R 27A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group which may be substituted with one or more substituents selected from Group G A , and R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, and R 34A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. A compound. 〔Aspect A15〕In Aspect A10, R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F AA C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected therefrom, or a 5- to 10-membered aromatic heterocyclic group {the 5- to 10-membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group optionally substituted with one or more halogen atoms}, R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, and R 34A is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect A16] In Aspect A11, R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F A or a 5- to 10-membered aromatic heterocyclic group {the 5- to 10-membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group optionally substituted with one or more halogen atoms}, and R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, and R 34A is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect A17] In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E A . [Aspect A18] In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group or a pyridyl group. [Aspect A19] In Aspect A9, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E A . [Aspect A20] In Aspect A10, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E A . 〔Aspect A21〕In aspect A11, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E A A compound which is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E 〔Aspect A22〕In aspect A13, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E A A compound which is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E 〔Aspect A23〕In aspect A14, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E A A compound which is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E 〔Aspect A24〕In aspect A15, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E A A compound which is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E 〔Aspect A25〕In aspect A16, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E A A compound which is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E 〔Aspect A26〕In aspect A15, Z A is a C2-C6 chain hydrocarbon group or a pyridyl group 〔Aspect A27〕In aspect A15, Z A is a C2-C6 chain hydrocarbon group or a pyridyl group, R 33A is a hydrogen atom, and R 34A is a C1-C3 chain hydrocarbon group 〔Aspect A28〕In aspect A12, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group E AA compound which is a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected therefrom. 〔Aspect A29〕In aspect A12, Z A is a C2-C6 chain hydrocarbon group or a pyridyl group. 〔Aspect A30〕In the compound N of the present invention, a compound in which m is 1 or 2. 〔Aspect A31〕In the compound N of the present invention, a compound in which m is 2. 〔Aspect A32〕In aspect A28, a compound in which m is 2. 〔Aspect A33〕In aspect A29, a compound in which m is 2. 〔Aspect A34〕In any one of aspects A1 to A33 or the compound N of the present invention, Q A is the group represented by Q A 1 or the group represented by Q A 2. 〔Aspect A35〕In any one of aspects A1 to A33 or the compound N of the present invention, Q A is the group represented by Q A 1. 〔Aspect A36〕In any one of aspects A1 to A33 or the compound N of the present invention, R 6A and R 7A are each a hydrogen atom. 〔Aspect A37〕In any one of aspects A1 to A33 or the compound N of the present invention, a compound in which R 8A is a hydrogen atom. 〔Aspect A38〕In any one of aspects A1 to A33 or the compound N of the present invention, a compound in which R 9A is a hydrogen atom. 〔Aspect A39〕In any one of aspects A1 to A33 or the compound N of the present invention, R 6A , R 7A , R 8A and R 9A are each a hydrogen atom. 〔Aspect A40〕In any one of aspects A1 to A33 or the compound N of the present invention, Q A is the group represented by Q A 1 or the group represented by Q A 2, and R 6A , R 7A , and R8A A compound in which each of them is a hydrogen atom. 〔Aspect A41〕In any one of Aspect A1 to Aspect A33 or the compound N of the present invention, Q A is Q A a group represented by Q 6A and R 7A A compound in which each of them is a hydrogen atom. 〔Aspect A42〕In any one of Aspect A1 to Aspect A29 or the compound N of the present invention, Q A is Q A a group represented by Q A 3 or a group represented by Q 〔Aspect A43〕In any one of Aspect A1 to Aspect A29 or the compound N of the present invention, Q A is Q A a group represented by Q 〔Aspect A44〕In any one of Aspect A1 to Aspect A29 or the compound N of the present invention, Q A is Q A a group represented by Q 〔Aspect A45〕In any one of Aspect A1 to Aspect A29 or the compound N of the present invention, Q A is Q A a group represented by Q A 3 or a group represented by Q 6A 、R 7A and R 9A A compound in which each of them is a hydrogen atom. 〔Aspect A46〕In any one of Aspect A1 to Aspect A29 or the compound N of the present invention, Q A is Q A a group represented by Q 9A A compound in which is a hydrogen atom. 〔Aspect A47〕In any one of Aspect A30, Aspect A31, or the compound N of the present invention, Q A is Q A a group represented by Q 1A and R 5A are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, or -OR 10A and R2A and R 4A are the same or different and are each a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NHC(O)OR 34A wherein R 3A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or -OR 10A wherein R 10A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, and R 34A is a C1-C3 chain hydrocarbon group.

[0021] 〔Aspect B1〕In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group. 〔Aspect B2〕In the compound N of the present invention, Z A is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms. 〔Aspect B3〕In the compound N of the present invention, Q A is the group represented by Q A 1 or the group represented by Q A 2, and m is 0 or 2. 〔Aspect B4〕In the compound N of the present invention, Q A is the group represented by Q A 1 or the group represented by Q A 2, and m is 2. 〔Aspect B5〕In the compound N of the present invention, Q A is the group represented by Q A 1 or the group represented by Q A 3, and m is 2. 〔Aspect B6〕In the compound N of the present invention, Q A is the group represented by Q A 1, and m is 0 or 2. 〔Aspect B7〕In the compound N of the present invention, Q A is the group represented by Q A 3, and m is 2. 〔Aspect B8〕In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group represented by Q A 1 or the group represented by Q A 2, and m is 0 or 2. 〔Aspect B9〕In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group represented by Q A 1 or the group represented by Q A 2, and m is 2. 〔Aspect B10〕In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group represented by Q A 1 or the group represented by Q A 3, and m is 2. 〔Aspect B11〕In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group represented by Q A 1, and m is 0 or 2. 〔Aspect B12〕In the compound N of the present invention, Z A is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group represented by Q A 3, and m is 2. 〔Aspect B13〕In the compound N of the present invention, Z A is a C2-C5 chain hydrocarbon group optionally substituted with one or more halogen atoms, and Q A is the group represented by Q A 1 or the group represented by Q A 2, and m is 0 or 2. 〔Aspect B14〕In the compound N of the present invention, Z A is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms, and Q A is the group represented by Q A 1 or the group represented by Q A 2, and a compound in which m is 2. 〔Aspect B15〕In the compound N of the present invention, Z A is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms, and Q A is the group represented by Q A 1 or the group represented by Q A 3, and a compound in which m is 2. 〔Aspect B16〕In the compound N of the present invention, Z A is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms, and Q A is the group represented by Q A 1, and a compound in which m is 0 or 2. 〔Aspect B17〕In the compound N of the present invention, Z A is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms, and Q A is the group represented by Q A 3, and a compound in which m is 2. 〔Aspect B18〕In any one of Aspect B1 to Aspect B17 or the compound N of the present invention, R 1A and R 5A are each a hydrogen atom, and R 2A and R 4A are the same or different and are a hydrogen atom or a halogen atom. 〔Aspect B19〕In any one of Aspect B1 to Aspect B17 or the compound N of the present invention, R 3A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10A , a hydrogen atom, or a halogen atom, and R 10A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. 〔Aspect B20〕In any one of Aspect B1 to Aspect B17 or the compound N of the present invention, R 1A and R 5Ais a hydrogen atom, respectively, and R 2A and R 4A are the same or different and are a hydrogen atom or a halogen atom, and R 3A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10A , a hydrogen atom, or a halogen atom (provided that R 1A , R 2A , R 3A , R 4A and R 5A at least one of which is not a hydrogen atom). 〔Aspect B21〕In any of Aspect B1 to Aspect B17 or the compound N of the present invention, R 1A , R 3A , R 4A and R 5A are hydrogen atoms, respectively, R 2A is -OR 10A , and R 10A is a methyl group substituted with a phenyl group which may be substituted with one or more substituents selected from Group C A .

[0022] Next, the production method of the present compound and the compound of the present invention will be described.

[0023] Production Method A The compound represented by the formula (I-b) (hereinafter referred to as compound (I-b)) or the compound represented by the formula (I-c) (hereinafter referred to as compound (I-c)) can be produced by reacting the compound represented by the formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent.

Chemical formula

[0024] First, the method for producing compound (I-b) from compound (I-a) will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of these. Examples of the oxidizing agent used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. In the reaction, the oxidizing agent is usually used in a ratio of 1 to 1.2 moles per 1 mole of compound (I-a). When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be added as necessary. Examples of the base used in the reaction include sodium carbonate. The base is usually used in a ratio of 0.01 to 1 mole per 1 mole of compound (I-a). Examples of the catalyst used in the reaction include tungstic acid and sodium tungstate. The catalyst is usually used in a ratio of 0.01 to 0.5 mole per 1 mole of compound (I-a). The reaction temperature is usually in the range of -20 to 80°C. The reaction time is usually in the range of 0.1 to 12 hours. After completion of the reaction, water is added to the reaction mixture, and extraction is carried out with an organic solvent. The organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium hydrogen carbonate) as necessary. By drying and concentrating this organic layer, compound (I-b) can be obtained.

[0025] Next, a method for producing compound (I-c) from compound (I-b) will be described. Compound (I-c) can be produced by reacting compound (I-b) with an oxidizing agent. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of these. Examples of the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide. In the reaction, the oxidizing agent is usually used in a ratio of 1 to 2 moles per 1 mole of the compound (I-b). When using hydrogen peroxide as the oxidizing agent, a base or a catalyst may be added as necessary. Examples of the base used in the reaction include sodium carbonate. The base is usually used in a ratio of 0.01 to 1 mole per 1 mole of the compound (I-b). Examples of the catalyst used in the reaction include sodium tungstate. The catalyst is usually used in a ratio of 0.01 to 0.5 mole per 1 mole of the compound (I-b). The reaction temperature is usually in the range of -20 to 120 °C. The reaction time is usually in the range of 0.1 to 12 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium hydrogen carbonate) as necessary. The compound (I-c) can be obtained by drying and concentrating this organic layer.

[0026] Also, the compound (I-c) can be produced in a one-pot reaction by reacting the compound (I-a) with an oxidizing agent. The reaction can be carried out according to the method for producing the compound (I-c) from the compound (I-b), using the oxidizing agent in a ratio of usually 2 to 5 moles per 1 mole of the compound (I-a).

[0027] Production Method B The compound represented by the formula (IA-a) (hereinafter referred to as compound (IA-a)) can be produced by reacting the compound represented by the formula (M-1) (hereinafter referred to as compound (M-1)) with the compound represented by the formula (M-2) (hereinafter referred to as compound (M-2)) in the presence of a copper catalyst and a base.

Chemical formula

[0028] Production Method C The compound represented by the formula (I-a1) (hereinafter referred to as compound (I-a1)) can be produced by reacting the compound represented by the formula (M-3) (hereinafter referred to as compound (M-3)) with the compound represented by the formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of a base.

Chemical formula

[0029] Production Method D The compound (IA-a) can be produced by reacting a compound represented by the formula (M-4) (hereinafter referred to as the compound (M-4)) with a compound represented by the formula (R-2) (hereinafter referred to as the compound (R-2)) in the presence of a base.

Chemical formula

[0030] Production method E The compound represented by formula (IA-a2) (hereinafter referred to as compound (IA-a2)) can be produced by carrying out a first step of reacting the compound represented by formula (IA-a1) (hereinafter referred to as compound (IA-a1)) with butyllithium or isopropylmagnesium chloride to obtain a compound represented by formula (M-5) (hereinafter referred to as compound (M-5)), and a second step of reacting compound (M-5) with a halogenating agent to obtain compound (IA-a2). [Chemical formula] [In the formula, M 1 represents a lithium atom or MgCl, R 3B represents a halogen atom, and the other symbols have the same meanings as described above.

[0031] The first step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; and mixtures of two or more of these. For the reaction, butyllithium or isopropylmagnesium chloride is usually used in a ratio of 1 to 10 moles per 1 mole of compound (IA-a1). The reaction temperature is usually in the range of -78 to 80 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the obtained compound (M-5) can be used in the second step without performing post-treatment operations.

[0032] The second step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; and mixtures of two or more of these. Examples of the halogenating agent used in the reaction include iodine, bromine, N-bromosuccinimide, N-chlorosuccinimide, and N-fluorobis(phenylsulfonyl)amine. In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles per 1 mole of the compound (M-5). The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is dried and concentrated to obtain the compound (IA-a2).

[0033] Production Method F The compound represented by the formula (IB-a) (hereinafter referred to as compound (IB-a)) can be produced by reacting the compound represented by the formula (M-6) (hereinafter referred to as compound (M-6)) with the compound represented by the formula (R-3) (hereinafter referred to as compound (R-3)).

Chemical formula

[0034] Production Method G The compound represented by formula (I-d) (hereinafter referred to as compound (I-d)) can be produced by reacting the compound represented by formula (M-13) (hereinafter referred to as compound (M-13)) with the compound represented by formula (R-5) (hereinafter referred to as compound (R-5)). [Chemical formula] [In the formula, X 3 represents a chlorine atom, a bromine atom, or -OR 34 , and the other symbols represent the same meanings as described above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of these. In the reaction, compound (R-5) is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-13). A base may be used in the reaction as needed. Examples of the base used in the reaction include organic bases; alkali metal carbonates; and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-13). The reaction temperature is usually in the range of 0 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is dried and concentrated to obtain compound (I-d). Compound (M-13) can be produced according to Production Method B, Production Method C, or Production Method D. Compound (R-5) is a commercially available compound or can be produced using known methods.

[0035] Production Method H The compound represented by formula (I-e) (hereinafter referred to as compound (I-e)) can be produced by reacting the compound represented by formula (M-14) (hereinafter referred to as compound (M-14)) with compound (R-5). [Chemical formula] [In the formula, the symbols represent the same meanings as described above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of these. In the reaction, compound (R-5) is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-14). A base may be used in the reaction as needed. Examples of the base used in the reaction include organic bases; alkali metal carbonates; and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-14). The reaction temperature is usually in the range of 0 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is dried and concentrated to obtain compound (I-e). Compound (M-14) can be produced according to Production Method B, Production Method C, or Production Method D. Compound (R-5) is a commercially available compound or can be produced using a known method.

[0036] Production Method I The compound represented by formula (IC-a) (hereinafter referred to as compound (IC-a)) can be produced by reacting the compound represented by formula (M-15) (hereinafter referred to as compound (M-15)) with compound (R-2) in the presence of a base. [Chemical formula] [In the formula, the symbols represent the same meanings as described above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; amides; esters; sulfoxides; ketones; 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 hydroxides; and alkali metal hydrides. In the reaction, the compound (R-2) is usually used in a ratio of 1 to 10 moles and the base is usually used in a ratio of 1 to 10 moles per 1 mole of the compound (M-15). The reaction temperature is usually in the range of 0 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction mixture is extracted with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (IC-a). The compound (M-15) can be produced according to the methods described in J. Med. Chem., 2017, 60, 10205. or Org. Lett., 2002, 4, 2485.

[0037] Production method J The compound represented by the formula (I-f) (hereinafter referred to as compound (I-f)) can be produced by reacting the compound represented by the formula (M-16) (hereinafter referred to as compound (M-16)) with the compound represented by the formula (R-6) (hereinafter referred to as compound (R-6)).

Chemical formula

[0038] Production method K The compound represented by formula (I-g) (hereinafter referred to as compound (I-g)) can be produced by reacting the compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) with compound (R-6).

Chemical formula

[0039] Production method L The compound represented by formula (I-h) (hereinafter referred to as compound (I-h)) can be produced by reacting the compound represented by formula (I-i) (hereinafter referred to as compound (I-i)) with the compound represented by formula (R-7) (hereinafter referred to as compound (R-7)).

Chemical formula

[0040] Production Method M The compound represented by formula (I-j) (hereinafter referred to as compound (I-j)) can be produced by reacting the compound represented by formula (I-o) (hereinafter referred to as compound (I-o)) with compound (R-7).

Chemical formula

[0041] Production Method N The compound represented by formula (I-k) (hereinafter referred to as compound (I-k)) can be produced by carrying out a first step of reacting the compound represented by formula (M-20) (hereinafter referred to as compound (M-20)) with a halogenating agent to obtain the compound represented by formula (M-21) (hereinafter referred to as compound (M-21)), and a second step of reacting compound (M-21) with the compound represented by formula (R-8) (hereinafter referred to as compound (R-8)) to obtain compound (I-k). Compound (I-k) can also be produced by reacting compound (M-20) with compound (R-8) in the presence of a condensing agent.

Chemical formula

[0042] The first step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of these. Examples of the halogenating agent used in the reaction include thionyl chloride and oxalyl chloride. In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-20). A base may be used in the reaction as necessary. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-20). The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the obtained compound (M-21) can be used in the second step without performing a post-treatment operation.

[0043] The second step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of these. In the reaction, compound (R-8) is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-21). A base may be used in the reaction as necessary. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-21). The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is dried and concentrated to obtain compound (I-k). Compound (R-8) is a commercially available compound or can be produced using known methods.

[0044] Next, a method for producing compound (I-k) by reacting compound (M-20) with compound (R-8) in the presence of a condensing agent will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of these. Examples of the condensing agent used in the reaction include 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, N,N'-dicyclohexylcarbodiimide, and N,N'-carbonyldiimidazole. In the reaction, the condensing agent is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-20). A base may be used in the reaction as needed. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-20). The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is dried and concentrated to obtain compound (I-k).

[0045] Production Method O The compound represented by formula (I-m) (hereinafter referred to as compound (I-m)) can be produced by carrying out a first step of reacting compound (M-20) with a halogenating agent to obtain compound (M-21), and a second step of reacting compound (M-21) with the compound represented by formula (R-9) (hereinafter referred to as compound (R-9)) to obtain compound (I-m). Further, compound (I-m) can also be produced by reacting compound (M-20) with compound (R-9) in the presence of a condensing agent.

Chemical formula

[0046] Production Method P The compound represented by formula (I-n) (hereinafter referred to as compound (I-n)) can be produced by carrying out a first step of reacting the compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) with a halogenating agent to obtain a compound represented by formula (M-23) (hereinafter referred to as compound (M-23)), and a second step of reacting compound (M-23) with compound (R-8) to obtain compound (I-n). Further, compound (I-n) can also be produced by reacting compound (M-22) with compound (R-8) in the presence of a condensing agent. [Chemical formula] [In the formula, the symbols have the same meanings as described above.] These reactions can be carried out according to Production Method N, using compound (M-22) instead of compound (M-20).

[0047] Production Method Q The compound represented by formula (I-p) (hereinafter referred to as compound (I-p)) can be produced by carrying out a first step of reacting compound (M-22) with a halogenating agent to obtain compound (M-23), and a second step of reacting compound (M-23) with compound (R-9) to obtain compound (I-p). Further, compound (I-p) can also be produced by reacting compound (M-22) with compound (R-9) in the presence of a condensing agent. [Chemical formula] [In the formula, the symbols have the same meanings as described above.] These reactions can be carried out according to production method N using compound (M-22) instead of compound (M-20) and using compound (R-9) instead of compound (R-8).

[0048] The compound represented by formula (IA-a4) (hereinafter referred to as compound (IA-a4)) can be produced by carrying out a first step of reacting the compound represented by formula (IA-a3) (hereinafter referred to as compound (IA-a3)) with butyllithium or isopropylmagnesium chloride to obtain a compound represented by formula (M-24) (hereinafter referred to as compound (M-24)), and a second step of reacting compound (M-24) with a fluorinating agent to obtain compound (IA-a4).

Chemical formula

[0049] The first step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, and mixtures of two or more of these. For the reaction, butyllithium or isopropylmagnesium chloride is usually used in a ratio of 1 to 10 moles per 1 mole of compound (IA-a3). The reaction temperature is usually in the range of -78 to 80 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the obtained compound (M-24) can be used in the second step without performing a post-treatment operation.

[0050] The second step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, and mixtures of two or more of these. Examples of the fluorinating agent used in the reaction include N-fluorobis(phenylsulfonyl)amine. For the reaction, the fluorinating agent is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-24). The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is dried and concentrated to obtain the compound (IA-a4). The compound (IA-a3) can be produced according to Production Method B, Production Method C, or Production Method D.

[0051] Production Method R The compound (I-i) can be produced by reacting a compound represented by the formula (M-25) (hereinafter referred to as compound (M-25)) with a compound represented by the formula (R-10) (hereinafter referred to as compound (R-10)).

Chemical formula

[0052] Production Method S The compound (I-o) can be produced by reacting a compound represented by the formula (M-26) (hereinafter referred to as compound (M-26)) with compound (R-10).

Chemical formula

[0053] Production Method T 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 methods described in US Patent Application Publication No. 2018 / 0009778 or International Publication No. 2016 / 121970.

[0054] Next, the production methods of the present compound and the intermediates of the compound of the present invention will be described.

[0055] Reference Production Method A Compound (M-1) can be produced by reacting the compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) with an acid or a base.

Chemical Formula

[0056] Reference Production Method B Compound (M-7) can be produced by carrying out a first step of reacting the compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) with butyllithium or isopropylmagnesium chloride to obtain a compound represented by formula (M-9) (hereinafter referred to as compound (M-9)), and a second step of reacting compound (M-9) with a disulfide or a thiosulfonate ester to obtain compound (M-7).

Chemical Formula

[0057] Reference Production Method C The compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) can be produced by reacting the compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) with a sulfurizing agent.

Chemical formula

[0058] Reference Production Method D Compound (M-10) can be produced by reacting the compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) with the compound represented by formula (R-4) (hereinafter referred to as compound (R-4)).

Chemical formula

[0059] Reference Production Method E Compound (M-25) can be produced by reacting the compound represented by formula (I-q) (hereinafter referred to as compound (I-q)) with zinc.

Chemical formula

[0060] Reference Production Method F Compound (M-26) can be produced by reacting the compound represented by formula (I-r) (hereinafter referred to as compound (I-r)) with zinc.

Chemical formula

[0061] Reference Production Method G Compound (M-20) can be produced by hydrolyzing the compound represented by formula (M-27) (hereinafter referred to as compound (M-27)). [Chemical formula] [In the formula, the symbols represent the same meanings as described above.] The reaction can be carried out according to the method described in J. Am. Chem. Soc. 2006, 128, 3536. Compound (M-27) can be produced according to Production Method B, Production Method C, or Production Method D.

[0062] Reference Production Method H Compound (M-22) can be produced by hydrolyzing the compound represented by formula (M-28) (hereinafter referred to as compound (M-28)). [Chemical formula] [In the formula, the symbols represent the same meanings as described above.] The reaction can be carried out according to the method described in J. Am. Chem. Soc. 2006, 128, 3536. Compound (M-28) can be produced according to Production Method B, Production Method C, or Production Method D.

[0063] The present compound or 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 use or combined use means using this compound or the compound of the present invention and this component simultaneously, separately, or with a time interval. When using this compound or the compound of the present invention and this component simultaneously, this compound or the compound of the present invention and this component may be contained in separate formulations, or may be contained in one formulation. 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 this compound or the compound of the present invention.

[0064] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multi-site inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut intima disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport system complexes I, II, III, and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients. These are described in the classification based on the mode of action of IRAC.

[0065] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These are described in the classification based on the mode of action of FRAC.

[0066] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).

[0067] Group (d) is a group of repellent components.

[0068] Examples of the combination of this component with this compound or the compound of the present invention are described below. For example, alanycarb + SX means the combination of alanycarb and SX. The abbreviation SX means any one of the compounds SX1 to SX42 described in the examples, which is this compound or the compound of the present invention. Further, all the components described below are known components and can be obtained from commercially available preparations or produced by known methods. When this component is a microorganism, it can also be obtained from a microorganism depository institution. The numbers in parentheses represent CAS RN (registered trademark).

[0069] The combination of this component of group (a) with this compound or the compound of the present invention: Abamectin + SX, Acephate + SX, Acequinocyl + SX, Acetamiprid + SX, Acetoprole + SX, Acrinathrin + SX, Acynonapyr + SX, Afidopyropen + SX, Afoxolaner + SX, Alanycarb + SX, Aldicarb + SX, Allethrin + SX, Alpha-cypermethrin + SX, Alpha-endosulfan + SX, Aluminium phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, 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, Chinomethionat + 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, Cyproflanilide + SX, Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-methyl + SX, Diafenthiuron + SX, Diazinon + SX, Dichlorvos + SX, Dicloromezotiaz + 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, Ethiofencarb + SX, Ethion + SX, Ethiprole + SX, Ethoprophos + SX, Etofenprox + SX, Etoxazole + SX, Extract of Artemisia absinthium + SX, Extract of Azadirachta indica + SX, Extract of Cassia nigricans + SX, Extract of Clitoria ternatea + SX, Extract of Symphytum officinale + SX, Extract or simulated blend of Chenopodium ambrosioides + SX, Extract of Tanacetum vulgare + SX, Extract of Urtica dioica + SX, 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, Flufenoprox + 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, 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, nicofluprole + SX, nicotine + SX, nicotine-sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, oil of the seeds of Chenopodium anthelminticum + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + 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, spiropidion + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + S, X, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene constituents of the extract of Chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodium + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX,Triazamate + SX, Triazophos + SX, Trichlorfon + SX, Triflumezopyrim + SX, Triflumuron + SX, Trimethacarb + SX, Tyclopyrazoflor + SX, Vamidothion + SX, Wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, Xylylcarb + SX, Zeta-cypermethrin + SX, Zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, 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, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + 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, 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, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, BT crop protein Cry1Ab + SX,BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT crop protein Cry1A.105 + SX, BT crop protein Cry2Ab + SX, BT crop protein Vip3A + SX, 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 GV strain V22 + SX, Cryptophlebia leucotreta 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 NPV + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX, Orgyia pseudotsugata NPV + SX, Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua mNPV + SX, Spodoptera littoralis mNPV + SX, 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. Kurstaki 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 rinogensis 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。,

[0070] Combination of the main component of the above group (b) with the present compound or 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, chinomethionat + SX, chitin + SX, chloroinconazide + 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, Extract of Melaleuca alternifolia + SX, Extract of Reynoutria sachalinensis + SX, Extract of the cotyledons of lupine plantlets ("BLAD") + SX, Extract of Allium sativum + SX, Extract of Equisetum arvense + SX, Extract of Tropaeolum majus + 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, Fentin acetate + SX, Fentin chloride + SX,Triphenyltin 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, Fosetyl-aluminium + 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, Isofetamid + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Leaves and bark of Quercus + 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, Methyltetraprole + 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, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinoffumelin + SX, quinoxyfen + SX, quintozene + SX, Saponins of Chenopodium quinoa + 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, yellow 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-chloro-4-(2-fluorophenoxy)-2-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro, -4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl)-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl)-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, 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, 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, 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, (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, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX,Bacillus amyloliquefaciens (Aveo™ 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 lichenifor, Bacillus amyloliquefaciens 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。,

[0071] Combination of the present component of group (c) with the present compound or the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol + SX,Dichlorprop + SX, Dikegulac + SX, Dimethipin + SX, Diquat + SX, Ethephon + SX, Ethychlozate + SX, Flumetralin + SX, Flurprimidol + SX, Forchlorfenuron + SX, Formononetin + SX, Gibberellin A + SX, Gibberellin A3 + SX, Inabenfide + SX, Kinetin + SX, Lipochitooligosaccharide SP104 + SX, Maleic hydrazide + SX, Mefluidide + SX, Mepiquat-chloride + SX, Oxidized glutathione + SX, Paclobutrazol + SX, Pendimethalin + SX, Prohexandione-calcium + SX, Prohydrojasmon + SX, Pyraflufen-ethyl + SX, Sintofen + SX, Sodium 1-naphthaleneacetate + SX, Sodium cyanate + 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。,

[0072] Combination of the present component of group (d) with the present compound or the compound of the present invention: Anthraquinone + SX, Deet + SX, Icaridin + SX。

[0073] The ratio of the present compound or the compound of the present invention to the present component is not particularly limited, but examples of the weight ratio (present compound or compound of the present invention: present component) include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0074] The present compound or the compound of the present invention can be mixed or used in combination with chemical fertilizers (such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.).

[0075] The present compound, the compound of the present invention or composition A can control plant diseases caused by phytopathogenic microorganisms such as fungi, oomycetes, phytomyxea, bacteria, etc. Examples of fungi include Ascomycota, Basidiomycota, Blastocladiomycota, Chytridiomycota, Mucoromycota and Olpidiomycota. Specifically, for example, the following are included. The content in parentheses indicates the scientific name of the phytopathogenic microorganism that causes each disease.

[0076] Diseases of rice: rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing and withering disease (Sclerophthora macrospora), false blast and ear blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae); Diseases of wheat: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), stripe rust (Puccinia striiformis), stem rust (Puccinia graminis), leaf rust (Puccinia recondita), pink snow mold (Microdochium nivale, Microdochium majus), snow scald (Typhula incarnata, Typhula ishikariensis), loose smut (Ustilago tritici), bunt (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Stagonospora nodorum), tan spot (Pyrenophora tritici-repentis), damping-off caused by Rhizoctonia solani, take-all (Gaeumannomyces graminis), blast (Pyricularia graminis-tritici); Diseases of barley: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), stripe rust (Puccinia striiformis), stem rust (Puccinia graminis), leaf rust (Puccinia hordei), loose smut (Ustilago nuda), leaf scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), spot blotch (Cochliobolus sativus), leaf stripe (Pyrenophora graminea), Ramularia leaf spot (Ramularia collo-cygni), damping-off caused by Rhizoctonia solani; Diseases of maize: rust (Puccinia sorghi), southern rust (Puccinia polysora), gray leaf spot (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 verticillioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma disease (Physoderma maydis); Diseases of cotton: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola); Diseases of coffee: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); Diseases of rapeseed: sclerotinia rot (Sclerotinia sclerotiorum), black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae); Diseases of sugarcane: rust (Puccinia melanocephala, Puccinia kuehnii), smut (Ustilago scitaminea); Diseases of sunflower: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Diseases of citrus fruits: citrus melanose (Diaporthe citri), citrus scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), Phytophthora blight (Phytophthora parasitica, Phytophthora citrophthora), black mold rot (Aspergillus niger); Diseases of apples: Monilinia rot (Monilinia mali), Valsa canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), apple scab (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), Marssonina leaf blotch (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), Phytophthora blight (Phytophthora cactorum), cedar apple rust (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Diseases of Japanese pears: pear scab (Venturia nashicola, Venturia pirina), Alternaria leaf spot (Alternaria alternata Japanese pear pathotype), pear rust (Gymnosporangium haraeanum); Diseases of peaches: brown rot (Monilinia fructicola), scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), leaf curl (Taphrina deformans); Diseases of grapes: anthracnose (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola); Diseases of persimmons: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf spot (Cercospora kaki, Mycosphaerella nawae); Diseases of figs: rust (Phakopsora nishidana); Diseases of cucurbits: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Didymella bryoniae), brown spot (Corynespora cassiicola), Fusarium wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), Phytophthora blight (Phytophthora capsici), damping-off (Pythium sp.); Diseases of tomatoes: early blight (Alternaria solani), leaf mold (Cladosporium fulvum), Septoria leaf spot (Pseudocercospora fuligena), Phytophthora blight (Phytophthora infestans), powdery mildew (Leveillula taurica); Diseases of eggplants: phomopsis blight (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 onions: rust (Puccinia allii); Diseases of soybeans: purple blotch (Cercospora kikuchii), black spot (Elsinoe glycines), black dot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown leaf spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), target spot (Cercospora sojina), sclerotinia rot (Sclerotinia sclerotiorum), powdery mildew (Microsphaera diffusa), Phytophthora root and stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death syndrome (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis complex (Diaporthe longicolla); Diseases of kidney beans: sclerotinia rot (Sclerotinia sclerotiorum), rust (Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Diseases of peanuts: black leaf spot (Cercospora personata), brown leaf spot (Cercospora arachidicola), southern blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani); Diseases of potatoes: early blight (Alternaria solani), late blight (Phytophthora infestans), pink rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), Verticillium wilt (Verticillium albo - atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), wart disease (Synchytrium endobioticum); Diseases of strawberries: powdery mildew (Sphaerotheca humuli); Diseases of tea: reticulum disease (Exobasidium reticulatum), white spot disease (Elsinoe leucospila), ring spot disease (Pestalotiopsis sp.), anthracnose (Colletotrichum theae - sinensis); Diseases of tobacco: brown spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), Phytophthora blight (Phytophthora nicotianae); Diseases of sugar beets: leaf spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root rot (Aphanomyces cochlioides), rust (Uromyces betae); Diseases of roses: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases of chrysanthemums: Septoria leaf spot (Septoria chrysanthemi - indici), white rust (Puccinia horiana); Diseases of onions: white leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), sclerotial rot (Botrytis squamosa); Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); Diseases of radishes: black spot (Alternaria brassicicola); Diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red rot (Pythium aphanidermatum); Diseases of bananas: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola); Diseases of lentils: Ascochyta disease (Ascochyta lentis); Diseases of chickpeas: Ascochyta disease (Ascochyta rabiei); Diseases of peppers: anthracnose (Colletotrichum scovillei); Diseases of mangoes: anthracnose (Colletotrichum acutatum); Diseases of fruit trees: white root rot (Rosellinia necatrix), purple root rot (Helicobasidium mompa); Diseases of fruits such as apples and pears after harvest: Mucor rot (Mucor piriformis); Seed diseases or diseases in the early growth stage 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 spp. (e.g., Polymyxa betae and Polymyxa graminis); Diseases caused by bacteria: Seedling blight of rice (Burkholderia plantarii), Angular leaf spot of cucumber (Pseudomonas syringae pv. lachrymans), Bacterial wilt of eggplant (Ralstonia solanacearum), Citrus canker (Xanthomonas citri), Soft rot of Chinese cabbage (Erwinia carotovora), Common scab of potato (Streptomyces scabiei), Goss's wilt of corn (Clavibacter michiganensis), Pierce's disease of grape, olive, peach, etc. (Xylella fastidiosa), Crown gall of Rosaceae plants such as apple, peach, strawberry, etc. (Agrobacterium tumefaciens).

[0077] As a method for controlling plant diseases of the present invention, an effective amount of the present compound, the compound of the present invention or Composition A is applied to plants or the soil in which the plants are cultivated. Examples of the application methods include foliar application, soil application and seed treatment.

[0078] The present compound, the compound of the present invention, or Composition A is usually mixed with an inert carrier such as a solid carrier or a liquid carrier, and if necessary, a surfactant and other formulation adjuvants are added to formulate it into emulsions, oils, powders, granules, wettable powders, granule wettable powders, flowables, dry flowables, microcapsules, etc. These formulations usually contain the present compound, the compound of the present invention, or Composition A in a weight ratio of 0.1 to 99%.

[0079] Examples of the solid carrier include fine powders and granular materials such as 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, superphosphate, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc., nylon resins such as nylon-6, nylon-11, nylon-66, etc., polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, etc.).

[0080] Examples of the liquid carrier include water, alcohols (such as methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (such as acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (such as toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (such as hexane, cyclohexane, kerosene, gas oil, etc.), esters (such as ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (such as acetonitrile, isobutyronitrile, etc.), ethers (such as 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 (such as DMF, N,N-dimethylacetamide, etc.), sulfoxides (such as DMSO, etc.), propylene carbonate, and vegetable oils (such as soybean oil, cottonseed oil, etc.).

[0081] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates. Specifically, Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (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 (registered trademark) X 45, AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark) etc. can be mentioned.

[0082] Examples of other formulation adjuvants include fixing agents, dispersants, coloring agents, stabilizers, etc. Specifically, for example, casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol) can be mentioned.

[0083] In the present invention, plants include the whole plant and specific parts of the plant. Examples of specific parts of the plant include foliage, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0084] The vegetative reproductive organ means an organ among the roots, stems, leaves, etc. of a plant that has the ability to grow when the part is separated from the main body and placed in the soil. Examples of vegetative reproductive organs include tuberous root, creeping root, bulb, corm (or solid bulb), tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. Note that stolons are sometimes called runners, propagules are also called bulbils, and are divided into broad buds and bulbils. Vine cutting means the shoots (a general term for leaves and stems) of sweet potatoes, yams, etc. Bulbs, corms, tubers, rhizomes, cane cuttings, rhizophores, or tuberous roots are collectively called bulbs. The cultivation of yams begins by planting tubers in the soil, and the tubers used are generally called seed tubers.

[0085] Examples of seed treatment include treating the seeds or vegetative reproductive organs with the present compound, the compound of the present invention, or Composition A. Specifically, for example, a spraying treatment in which a suspension of the present compound, the compound of the present invention, or Composition A is atomized and sprayed onto the seed surface or the surface of the vegetative reproductive organ, a coating treatment in which the present compound, the compound of the present invention, or Composition A is applied to the seeds or vegetative reproductive organs, a dipping treatment in which the seeds are immersed in a chemical solution of the present compound, the compound of the present invention, or Composition A for a certain period of time, and a method of coating the seeds or vegetative reproductive organs with a carrier containing the present compound, the compound of the present invention, or Composition A (film coating treatment, pellet coating treatment, etc.). Among the above-mentioned vegetative reproductive organs, seed tubers are particularly mentioned. When treating seeds or vegetative reproductive organs with Composition A, Composition A can be treated as one formulation on the seeds or vegetative reproductive organs, or Composition A can be treated on the seeds or vegetative reproductive organs in multiple times as different formulations. As a method of treating Composition A in multiple times as different formulations, for example, a formulation containing only this compound or the compound of the present invention as an active ingredient is treated, and after the seeds or vegetative reproductive organs are air-dried, a formulation containing this component is treated; and a method of treating a formulation containing this compound and this component or the compound of the present invention and this component as an active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating a formulation containing this component other than the treated this component is mentioned. The seeds or vegetative reproductive organs holding this compound, the compound of the present invention or Composition A in the present invention mean those in a state where this compound, the compound of the present invention or Composition A is adhered to the surface of the seeds or vegetative reproductive organs. The above-mentioned seeds or vegetative reproductive organs holding this compound, the compound of the present invention or Composition A may have materials other than this compound, the compound of the present invention or Composition A adhered thereto before and after this compound, the compound of the present invention or Composition A is adhered to the seeds or vegetative reproductive organs. Also, when Composition A adheres to the surface of seeds or vegetative reproductive organs as a layer, the layer is composed of one layer or a plurality of layers. Also, in the case of being composed of a plurality of layers, each layer is a layer containing one or more active ingredients, or is composed of a layer containing one or more active ingredients and a layer not containing an active ingredient. The seeds or vegetative reproductive organs holding this compound, the compound of the present invention or Composition A can be obtained, for example, by applying a formulation containing this compound, the compound of the present invention or Composition A to the seeds or vegetative reproductive organs by the above-mentioned seed treatment method.

[0086] The application amount of this compound, the compound of the present invention or Composition A varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc. However, in the case of foliage treatment or soil treatment, 1000m 2The amount is generally 1 to 500 g. In the case of seed treatment, the amount of the present compound, the compound of the present invention or Composition A is generally 0.001 to 100 g per 1 Kg of seeds. When the present compound, the compound of the present invention or Composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water and applied so that the active ingredient concentration becomes 0.01 to 10,000 ppm, and powders, granules, etc. are usually applied as they are.

[0087] The present compound, the compound of the present invention or Composition A can be used as a plant disease control agent in agricultural fields such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0088] Maize (dent corn, flint corn, soft corn, popcorn, waxy corn, sweet corn, field corn), rice (long grain rice, short grain rice, medium grain rice, japonica rice, tropical japonica rice, indica rice, javanica rice, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, glutinous barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oats type, spring oats type), sorghum, cotton (upland cotton, pima cotton), soybean (fully mature seed harvest variety, edamame variety, green forage variety, each indeterminate growth type, determinate growth type, semi-determinate growth type), peanut, buckwheat, sugar beet (for sugar production, for feed, root vegetable, leaf vegetable, for fuel), rapeseed (winter rapeseed type, spring rapeseed type), sunflower (for oil extraction, for food, for ornamental), sugarcane, tobacco, camphor tree, mulberry, Solanaceae vegetables (eggplant, tomato, pepper, pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard spinach, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), Liliaceae vegetables (scallion, onion, garlic, asparagus, etc.), Apiaceae vegetables (carrot, parsley, celery, American cow parsnip, etc.), Chenopodiaceae vegetables (spinach, lamb's quarters, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, pomaceous fruits (apple, pear, Japanese pear, Chinese pear, quince, quince, etc.), stone fruits (peach, plum, nectarine, Japanese apricot, apricot, apricot, prune, etc.), citrus fruits (mandarin orange, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster mushroom, fig, olive, loquat, banana, coffee, date palm, coconut palm, ornamental plants, forest plants, grasses,Forage grasses, etc.

[0089] The above plants are not particularly limited as long as they are commonly cultivated varieties. The above plants include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants imparted with resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants capable of synthesizing selective toxins such as those known in the genus Bacillus such as Bacillus thuringiensis; and plants that can synthesize gene fragments that partially match endogenous genes derived from harmful insects and impart specific insecticidal activity by inducing gene silencing (RNAi; RNA interference) in the target harmful insect body.

Example

[0090] The following manufacturing examples, reference manufacturing examples, formulation examples, and test examples are provided to more specifically illustrate the present invention, but the present invention is not limited to these examples. In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, Bu represents a butyl group, i-Bu represents an isobutyl group, s-Bu represents a sec-butyl group, t-Bu represents a tert-butyl group, c-Bu represents a cyclobutyl group, Pen represents a pentyl group, i-Pen represents an isopentyl group, neo-Pen represents a neopentyl group, c-Hex represents a cyclohexyl group, Allyl represents an allyl group, Ph represents a phenyl group, 2-Py represents a 2-pyridyl group, 3-Py represents a 3-pyridyl group, and 4-Py represents a 4-pyridyl group. When the phenyl group or pyridyl group has a substituent, the substituent is indicated together with the substitution position before the symbol. For example, 2-CN-Ph represents a 2-cyanophenyl group, 3,4-F2-Ph represents a 3,4-difluorophenyl group, and 4-(OMe)-Ph represents a 4-methoxyphenyl group.

[0091] Manufacturing examples of the present compound and the compounds of the present invention are shown.

[0092] Reference Manufacturing Example 1 To a mixture of 2.2 g of dimethylsulfamoylpyrazole and 20 mL of THF, 5.3 mL of butyllithium (2.6 M, hexane solution) was added dropwise at -78°C, and the mixture was stirred at -78°C for 30 minutes. 1.8 g of diethyldisulfide was added to the resulting mixture, and the mixture was stirred at room temperature for 4 hours. An aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.0 g of Intermediate MA1-1 represented by the following formula.

Chemical formula

[0093] Reference Production Example 1-1 The compounds produced according to Reference Production Example 1 and their physical property values are shown below. Formula (MA1) [Chemical formula] In the compound represented by, R 6 , R 7 , and a compound in which the combination of Z is any of the combinations described in [Table MA1].

[0094] [Table 1] Intermediate MA1-2: 1 1H-NMR (CDCl3) δ: 7.61 (1H, d), 6.16 (1H, d), 3.02 (6H, s), 2.91 (2H, dd), 1.74 (2H, m), 1.06 (3H, t). Intermediate MA1-3: 1 1H-NMR (CDCl3) δ: 7.63 (1H, d), 6.09 (1H, d), 3.01 (6H, s), 2.49 (3H, s). Intermediate MA1-4: 1 1H-NMR (CDCl3) δ: 7.62 (1H, d), 6.28 (1H, d), 3.45 (1H, m), 3.03 (6H, s), 1.36 (6H, d). Intermediate MA1-5: 1 1H-NMR (CDCl3) δ: 7.62 (1H, d), 6.16 (1H, d), 3.02 (6H, s), 2.93 (2H, dd), 1.70 (2H, m), 1.48 (2H, m), 0.94 (3H, t). Intermediate MA1-6: 1H-NMR (CDCl3) δ: 7.61 (1H, d), 6.14 (1H, d), 3.02 (6H, s), 2.81 (2H, d), 1.96 (1H, m), 1.06 (6H, d). Intermediate MA1-7: 1 H-NMR (CDCl3) δ: 7.61 (1H, d), 6.16 (1H, d), 3.02 (6H, s), 2.92 (2H, dd), 1.71 (2H, m), 1.47 - 1.29 (4H, m), 0.91 (3H, t). Intermediate MA1-8: 1 H-NMR (CDCl3) δ: 7.62 (1H, d), 6.16 (1H, d), 3.02 (6H, s), 2.93 (2H, m), 1.74 (1H, m), 1.63 - 1.57 (2H, m), 0.93 (6H, d). Intermediate MA1-9: 1 H-NMR (CDCl3) δ: 7.61 (1H, d), 6.26 (1H, d), 3.20 (1H, m), 3.03 (6H, s), 2.07 - 2.00 (2H, m), 1.83 - 1.76 (2H, m), 1.65 - 1.26 (6H, m). Intermediate MA1-10: 1 H-NMR (CDCl3) δ: 7.61 (1H, d), 6.23 (1H, d), 5.88 (1H, m), 5.24 (1H, m), 5.17 (1H, m), 3.58 (2H, m), 3.02 (6H, s). Intermediate MA1-11: 1 H-NMR (CDCl3) δ: 7.57 - 7.51 (3H, m), 7.42 - 7.37 (3H, m), 5.78 (1H, d), 3.04 (6H, s). Intermediate MA1-12: 1 H-NMR (CDCl3) δ: 7.52 (2H, m), 7.47 (1H, d), 6.94 (2H, m), 5.56 (1H, d), 3.84 (3H, s), 3.04 (6H, s). Intermediate MA1-13:1 1H-NMR (CDCl3) δ: 7.54 (1H, d), 7.45 (2H, m), 7.36 (2H, m), 5.85 (1H, d), 3.05 (6H, s). Intermediate MA1-14: 1 1H-NMR (CDCl3) δ: 7.52 (1H, d), 7.42 - 7.36 (2H, m), 6.98 - 6.94 (2H, m), 5.74 (1H, d), 3.84 (3H, s), 3.04 (6H, s). Intermediate MA1-15: 1 1H-NMR (CDCl3) δ: 7.59 (1H, d), 7.48 (1H, m), 7.40 (1H, m), 7.32 (1H, m), 7.26 (1H, m), 5.89 (1H, d), 3.05 (6H, s). Intermediate MA1-16: 1 1H-NMR (CDCl3) δ: 8.46 (2H, m), 7.75 (1H, d), 7.05 (2H, m), 6.57 (1H, d), 3.07 (6H, s). Intermediate MA1-17: 1 1H-NMR (CDCl3) δ: 8.45 (1H, m), 7.73 (1H, d), 7.57 (1H, m), 7.12 - 7.08 (2H, m), 6.60 (1H, d), 3.04 (6H, s). Intermediate MA1-18: 1 1H-NMR (CDCl3) δ: 7.56 (1H, d), 3.08 (6H, s), 2.90 (2H, t), 1.62 (2H, m), 1.01 (3H, t).

[0095] Reference Production Example 2 A mixture of 3.0 g of Intermediate MA1-1 and 30 mL of trifluoroacetic acid was stirred at 50 °C for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.9 g of Intermediate MA2-1 represented by the following formula. [Chemical formula] Intermediate MA2-1: 1 H-NMR (CDCl3) δ: 7.62 (1H, d), 6.37 (1H, d), 2.90 (2H, q), 1.30 (3H, t).

[0096] Reference Production Example 2-1 The compounds produced according to Reference Production Example 2 and their physical property values are shown below. Formula (MA2) [Chemical formula] In the compound represented by, R 6 , R 7 , and a compound in which the combination of Z is any of the combinations described in [Table MA2].

[0097] [Table 2] Intermediate MA2-2: 1 H-NMR (CDCl3) δ: 7.62 (1H, d), 6.35 (1H, d), 2.86 (2H, dd), 1.65 (2H, m), 1.00 (3H, t). Intermediate MA2-3: 1 H-NMR (CDCl3) δ: 7.60 (1H, d), 6.31 (1H, d), 2.51 (3H, s). Intermediate MA2-4: 1 H-NMR (CDCl3) δ: 7.65 (1H, d), 6.41 (1H, d), 3.28 (1H, m), 1.29 (6H, d). Intermediate MA2-5: 1 H-NMR (CDCl3) δ: 7.59 (1H, d), 6.35 (1H, d), 2.88 (2H, dd), 1.62 (2H, m), 1.42 (2H, m), 0.90 (3H, t). Intermediate MA2-6: 11H-NMR (CDCl3) δ: 7.65 (1H, br s), 6.37 (1H, br s), 2.83 (2H, d), 1.86 (1H, m), 1.02 (6H, d). Intermediate MA2-7: 1 1H-NMR (CDCl3) δ: 7.58 (1H, d), 6.34 (1H, d), 2.88 (2H, dd), 1.64 (2H, m), 1.43 - 1.26 (4H, m), 0.88 (3H, t). Intermediate MA2-8: 1 1H-NMR (CDCl3) δ: 7.59 (1H, d), 6.34 (1H, d), 2.89 (2H, dd), 1.70 (1H, m), 1.52 (2H, m), 0.89 (6H, d). Intermediate MA2-9: 1 1H-NMR (CDCl3) δ: 7.60 (1H, d), 6.39 (1H, d), 3.03 - 2.94 (1H, m), 2.01 - 1.93 (2H, m), 1.79 - 1.71 (2H, m), 1.63 - 1.55 (1H, m), 1.41 - 1.18 (5H, m). Intermediate MA2-10: 1 1H-NMR (CDCl3) δ: 7.62 (1H, br s), 6.38 (1H, br s), 5.89 (1H, m), 5.11 - 5.03 (2H, m), 3.50 (2H, m). Intermediate MA2-11: 1 1H-NMR (CDCl3) δ: 7.54 (1H, d), 7.28 - 7.14 (5H, m), 6.43 (1H, d). Intermediate MA2-12: 1 1H-NMR (CDCl3) δ: 7.54 (1H, br s), 7.34 (2H, m), 6.83 (2H, m), 6.31 (1H, br s), 3.78 (3H, s). Intermediate MA2-13: 11H-NMR (CDCl3) δ: 7.60 (1H, d), 7.26 - 7.15 (4H, m), 6.44 (1H, d). Intermediate MA2-14: 1 1H-NMR (CDCl3) δ: 7.63 (1H, d), 7.19 (1H, m), 6.96 (1H, m), 6.90 - 6.81 (2H, m), 6.48 (1H, d), 3.92 (3H, s). Intermediate MA2-15: 1 1H-NMR (CDCl3) δ: 7.67 (1H, d), 7.38 - 7.33 (1H, m), 7.12 - 7.05 (2H, m), 6.89 - 6.84 (1H, m), 6.55 (1H, d). Intermediate MA2-16: 1 1H-NMR (CDCl3) δ: 8.37 (2H, m), 7.74 (1H, d), 6.89 (2H, m), 6.60 (1H, d). Intermediate MA2-17: 1 1H-NMR (CDCl3) δ: 8.44 (1H, d), 7.70 (1H, m), 7.50 (1H, m), 7.07 - 6.98 (2H, m), 6.56 (1H, d). Intermediate MA2-18: 1 1H-NMR (CDCl3) δ: 10.56 (1H, br s), 7.48 (1H, d), 2.79 (2H, t), 1.62 (2H, m), 1.00 (3H, t).

[0098] Reference Production Example 3 To a mixture of 3.0 g of 1-(4-chlorophenyl)-1H-pyrazol-3-ol and 6.0 mL of pyridine, 5.0 g of trifluoromethanesulfonic anhydride was added dropwise at 0 °C, and the mixture was stirred at 0 °C for 2 hours. Aqueous sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 5.3 g of Intermediate MA3-1 represented by the following formula.

Chemical Structure

[0099] Reference Production Example 4 A mixture of 1.4 g of Intermediate MA2-2, 2.6 g of 3-iodoaniline, 1.5 g of copper(I) iodide, 1.4 g of trans-N,N'-dimethylcyclohexane-1,2-diamine, 2.8 g of potassium carbonate, and 25 mL of DMF was stirred at 80°C for 10 hours. Water was added to the resulting mixture and filtered. The filtrate was extracted with ethyl acetate, and the obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 70:30) to obtain 2.2 g of Intermediate MA4-1 represented by the following formula. [Chemical formula] Intermediate MA4-1: 1 H-NMR (CDCl3) δ: 7.82 (1H, d), 7.18 (1H, t), 7.09 (1H, t), 6.97 (1H, m), 6.57 (1H, m), 6.38 (1H, d), 3.81 (2H, br s), 2.99 (2H, m), 1.74 (2H, m), 1.04 (3H, t).

[0100] Reference Production Example 4-1 The compounds produced according to Reference Production Example 4 and their physical property values are shown below. Formula (MA4) [Chemical formula] In the compound represented by, R 1 , R 2 , R 3 , R 4 , and R 5 Compounds in which the combination of is any of the combinations described in [Table MA4].

[0101] [Table 3] Intermediate MA4-2: 1H-NMR (CDCl3) δ: 7.72 (1H, d), 7.42 (2H, m), 6.72 (2H, m), 6.37 (1H, d), 3.72 (2H, br s), 2.97 (2H, m), 1.73 (2H, m), 1.03 (3H, t). Intermediate MA4-3: 1 H-NMR (CDCl3) δ: 7.72 (1H, d), 7.37 (1H, m), 7.21 (1H, m), 6.81 (1H, t), 6.37 (1H, d), 3.76 (2H, br s), 2.98 (2H, t), 1.74 (2H, m), 1.03 (3H, t). Intermediate MA4-4: 1 H-NMR (CDCl3) δ: 8.12 (2H, m), 7.95 (1H, d), 7.74 (2H, m), 6.44 (1H, d), 4.39 (2H, q), 3.05 (2H, t), 1.77 (2H, m), 1.41 (3H, t), 1.06 (3H, t). Intermediate MA4-5: 1 H-NMR (CDCl3) δ: 8.27 (1H, m), 7.95 - 7.92 (3H, m), 7.52 (1H, t), 6.44 (1H, d), 4.42 (2H, q), 3.04 (2H, t), 1.77 (2H, m), 1.42 (3H, t), 1.05 (3H, t).

[0102] Reference Production Example 5 A mixture of 7.8 g of Intermediate MA4-5, 2.9 g of potassium hydroxide, 40 mL of ethanol, and 20 mL of water was stirred at 50 °C for 4 hours. 30 mL of 2.0 M hydrochloric acid was added to the resulting mixture and stirred for 1 hour. The resulting mixture was filtered, and the obtained solid was dried under reduced pressure to obtain 5.8 g of Intermediate MA5-1 represented by the following formula.

Chemical formula

[0103] Reference Production Example 5-1 Using Intermediate MA4-4 instead of Intermediate MA4-5 and following Reference Production Example 5, Intermediate MA5-2 represented by the following formula was obtained.

Chemical Formula

[0104] Reference Production Example 6 A mixture of 4.2 g of the compound IIA-150 of the present invention, 0.8 g of ammonium chloride, 2.8 g of zinc, 20 mL of THF, and 10 mL of water was stirred at 0 °C for 2 hours. After filtering the resulting mixture, the obtained filtrate was extracted with MTBE. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.8 g of Intermediate MA6-1 represented by the following formula.

Chemical Formula

[0105] Reference Production Example 6-1 Using Compound IIA-149 of the present invention instead of Compound IIA-150, Intermediate MA6-2 represented by the following formula was obtained according to Reference Production Example 6.

Chemical formula

[0106] Production Example 1 A mixture of 0.38 g of Intermediate MA2-1, 0.78 g of 4-iodotoluene, 0.46 g of copper(I) iodide, 0.43 g of trans-N,N'-dimethylcyclohexane-1,2-diamine, 0.87 g of potassium carbonate, and 10 mL of DMF was stirred at 80 °C for 4 hours. Water was added to the resulting mixture and it was filtered. The filtrate was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 20:1) to obtain 0.61 g of Compound IIA-1 of the present invention represented by the following formula.

Chemical formula

[0107] Production Example 1-1 The compounds produced according to Production Example 1 and their physical property values are shown below. Formula (A1)

Chemical formula

[0108]

Table 4

[0109]

Table 5

[0110]

Table 6

[0111] Production Example 2 A mixture of 1.0 g of Intermediate MA3-1, 1.0 g of sodium ethanethiolate, and 10 mL of DMF was stirred at 120 °C for 5 hours. Aqueous sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 1.3 g of a crude product of Compound IIA-60 of the present invention represented by the following formula. [Chemical formula] Compound IIA-60 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.61 (2H, m), 7.40 (2H, m), 6.42 (1H, d), 3.05 (2H, q), 1.39 (3H, t).

[0112] Production Example 3 To a mixture of 0.27 g of the compound IIA-37 of the present invention and 10 mL of THF, 0.58 mL of butyllithium (2.6 M, hexane solution) was added dropwise at -78 °C, and the mixture was stirred at -78 °C for 30 minutes. 0.65 g of 1,2-dibromo-1,1,2,2-tetrachloroethane was added to the resulting mixture, and after stirring for 30 minutes, the mixture was stirred at room temperature for 4 hours. An aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 98:2) to obtain 0.16 g of the compound IIA-61 of the present invention represented by the following formula. [Chemical formula] Compound IIA-61 of the present invention: 1 H-NMR (CDCl3) δ: 7.83 (1H, d), 7.33 (2H, m), 6.42 (1H, d), 3.08 (2H, q), 1.41 (3H, t).

[0113] Production Example 4 To a mixture of 0.22 g of the compound IIA-1 of the present invention and 5 mL of chloroform, 0.25 g of mCPBA (purity 75%, 25% water-containing) was added at 0 °C, and the mixture was stirred at 0 °C for 2 hours. An aqueous sodium sulfite solution was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 50:50) to obtain 0.21 g of the compound IIA-62 of the present invention represented by the following formula. [Chemical formula] Compound IIA-62 of the present invention: 1 H-NMR (CDCl3) δ: 7.97 (1H, d), 7.56 (2H, m), 7.27 (2H, m), 6.93 (1H, d), 3.21 - 3.06 (2H, m), 2.40 (3H, s), 1.33 (3H, t).

[0114] Production Example 4-1 The compounds produced according to Production Example 4 and their physical property values are shown below. Formula (A2)

Chemical formula

[0115]

Table 7

[0116]

Table 8

[0117] Production Example 5 To a mixture of 0.22 g of the compound IIA-1 of the present invention and 5 mL of chloroform, 0.54 g of mCPBA (purity 75%, 25% water content) was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. An aqueous sodium sulfite solution was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 80:20) to obtain 0.25 g of the compound IIA-65 of the present invention represented by the following formula. [Chemical formula] Compound IIA-65 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.60 (2H, m), 7.29 (2H, m), 6.98 (1H, d), 3.35 (2H, q), 2.41 (3H, s), 1.39 (3H, t).

[0118] Production Example 5-1 Compounds produced according to Production Example 5 and their physical property values are shown below. Formula (A3) [Chemical formula] In the compound represented by, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are any of the combinations described in [Table IIA3-1], [Table IIA3-2], [Table IIA3-3], [Table IIA3-4], [Table IIA3-5] and [Table IA3].

[0119]

Table 9

[0120] [Table 10] Compound IIA-95 of the present invention: 11H-NMR (CDCl3) δ: 8.01 (1H, d), 7.45 (1H, m), 7.39 (1H, m), 7.29 (1H, m), 6.97 (1H, m), 3.35 (2H, q), 2.31 (3H, s), 1.40 (3H, t). Compound IIA-96 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.52 (1H, m), 7.43 (1H, m), 7.05 (1H, t), 6.98 (1H, d), 2.95 (3H, s), 3.35 (2H, q), 1.40 (3H, t). Compound IIA-97 of the present invention: 1 1H-NMR (CDCl3) δ: 8.07 (1H, d), 7.76 (1H, m), 7.70 (1H, m), 7.63 (1H, m), 7.06 (1H, d), 3.37 (2H, q), 1.41 (3H, t). Compound IIA-98 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.44 (2H, m), 7.02 (1H, d), 3.35 (2H, q), 1.40 (3H, t). Compound IIA-99 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.46 (2H, m), 7.03 (1H, d), 3.36 (2H, q), 1.41 (3H, t). Compound IIA-100 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.29 (2H, m), 7.00 (1H, d), 3.51 (2H, q), 2.24 (3H, t), 1.40 (3H, t). Compound IIA-101 of the present invention: 1 1H-NMR (CDCl3) δ: 8.00 (1H, d), 7.33 (2H, m), 7.02 (1H, d), 6.86 (1H, m), 3.36 (2H, q), 1.41 (3H, t). Compound IIA-102 of the present invention: 1 1H-NMR (CDCl3) δ: 8.05 (1H, d), 7.48 (2H, m), 7.07 (1H, d), 3.37 (2H, q), 1.41 (3H, t). Compound IIA-103 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.34 (2H, m), 7.00 (1H, d), 4.05 (3H, t), 3.35 (2H, q), 1.40 (3H, t). Compound IIA-104 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.30 (2H, m), 1.89 (2H, m), 1.06 (3H, t). Compound IIA-105 of the present invention: 1 1H-NMR (CDCl3) δ: 7.94 (1H, d), 7.60 (2H, m), 7.30 - 7.28 (2H, m), 6.97 (1H, d), 3.31 (2H, m), 2.41 (3H, s), 1.89 (2H, m), 1.04 (3H, t). Compound IIA-106 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.64 (2H, m), 7.50 (2H, m), 6.97 (1H, d), 3.31 (2H, m), 1.88 (2H, m), 1.36 (9H, s), 1.05 (3H, t). Compound IIA-107 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.45 (1H, m), 7.39 (1H, m), 7.30 (1H, m), 6.98 (1H, d), 3.31 (2H, m), 2.33 (3H, s), 1.89 (2H, m), 1.06 (3H, t). Compound IIA-108 of the present invention: 11H-NMR (CDCl3) δ: 7.98 (1H, d), 7.63 (1H, m), 7.56 - 7.46 (2H, m), 7.01 (1H, d), 3.31 (2H, m), 1.89 (2H, m), 1.07 (3H, t). Compound IIA-109 of the present invention: 1 1H-NMR (CDCl3) δ: 8.07 (1H, d), 7.76 (1H, m), 7.70 (1H, m), 7.63 (1H, m), 7.04 (1H, d), 3.32 (2H, m), 1.90 (2H, m), 1.07 (3H, t). Compound IIA-110 of the present invention: 1 1H-NMR (CDCl3) δ: 7.94 (1H, d), 7.29 (2H, m), 6.99 (1H, d), 3.31 (2H, m), 2.24 (3H, t), 1.89 (2H, m), 1.06 (3H, t). Compound IIA-111 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.46 (2H, m), 7.02 (1H, d), 3.31 (2H, m), 1.89 (2H, m), 1.07 (3H, t). Compound IIA-112 of the present invention: 1 1H-NMR (CDCl3) δ: 8.04 (1H, d), 7.48 (2H, m), 7.06 (1H, d), 3.32 (2H, m), 1.89 (2H, m), 1.08 (3H, t). Compound IIA-113 of the present invention: 1 1H-NMR (CDCl3) δ: 8.07 (1H, d), 7.89 (2H, m), 7.78 (2H, m), 7.40 (1H, d), 3.32 (2H, m), 8.90 (2H, m), 1.07 (3H, t). Compound IIA-114 of the present invention: 11H-NMR (CDCl3) δ: 7.99 (1H, d), 7.69 (2H, m), 7.47 (2H, m), 7.00 (1H, d), 3.45 (1H, m), 1.41 (6H, d). Compound IIA-115 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.33 (2H, m), 1.83 (2H, m), 1.46 (2H, m), 0.93 (3H, t). Compound IIA-116 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.25 (2H, d), 2.39 (1H, m), 1.11 (6H, d). Compound IIA-117 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.32 (2H, m), 1.85 (2H, m), 1.44 - 1.28 (4H, m), 0.89 (3H, t). Compound IIA-118 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.33 (2H, m), 1.77 - 1.66 (3H, m), 0.92 (6H, d). Compound IIA-119 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.69 (2H, m), 7.48 (2H, m), 6.98 (1H, d), 3.17 (1H, m), 2.18 (2H, m), 1.90 (2H, m), 1.73 - 1.13 (6H, m). Compound IIA-120 of the present invention: 11H-NMR (CDCl3) δ: 7.96 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 6.97 (1H, d), 5.90 (1H, m), 5.41 (1H, dd), 5.32 (1H, d), 4.05 (2H, d). Compound IIA-121 of the present invention: 1 1H-NMR (CDCl3) δ: 8.88 (2H, m), 7.95 - 7.91 (3H, m), 7.62 (2H, m), 7.45 (2H, m), 7.05 (1H, d). Compound IIA-122 of the present invention: 1 1H-NMR (CDCl3) δ: 8.72 (1H, m), 8.31 (1H, d), 8.00 - 7.95 (2H, m), 7.63 (2H, m), 7.51 (1H, m), 7.43 (2H, m), 7.19 (1H, d). Compound IIA-123 of the present invention: 1 1H-NMR (CDCl3) δ: 7.98 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.01 (1H, d), 3.35 (2H, q), 1.40 (3H, t). Compound IIA-124 of the present invention: 1 1H-NMR (CDCl3) δ: 8.01 (1H, d), 7.43 (2H, m), 7.03 (1H, d), 3.36 (2H, q), 1.41 (3H, t).

[0121] [Table 11] Compound IIA-125 of the present invention: 1 1H-NMR (DMSO-D6) δ: 8.78 (1H, d), 7.56 - 7.33 (8H, m), 7.12 - 7.07 (2H, m), 5.21 (2H, s), 3.41 - 3.37 (2H, m), 1.73 - 1.64 (2H, m), 0.96 (3H, t). Compound IIA-126 of the present invention: 11H-NMR (DMSO-D6) δ: 8.77 (1H, d), 7.54-7.53 (1H, m), 7.48-7.47 (2H, m), 7.37 (2H, d), 7.21 (2H, d), 7.09-7.06 (2H, m), 5.16 (2H, s), 3.40-3.37 (2H, m), 2.31 (3H, s), 1.73-1.64 (2H, m), 0.96 (3H, t). Compound IIA-127 of the present invention: 1 1H-NMR (DMSO-D6) δ: 8.77 (1H, d), 7.55-7.55 (1H, m), 7.49-7.47 (2H, m), 7.30-7.26 (3H, m), 7.16 (1H, d), 7.10-7.07 (2H, m), 5.16 (2H, s), 3.40-3.35 (2H, m), 2.33 (3H, s), 1.73-1.64 (2H, m), 0.96 (3H, t). Compound IIA-128 of the present invention: 1 1H-NMR (DMSO-D6) δ: 8.78 (1H, d), 7.58-7.57 (1H, m), 7.50-7.49 (2H, m), 7.45 (1H, d), 7.29-7.20 (3H, m), 7.14-7.11 (1H, m), 7.08 (1H, d), 5.19 (2H, s), 3.41-3.35 (2H, m), 2.36 (3H, s), 1.73-1.64 (2H, m), 0.96 (3H, t). Compound IIA-129 of the present invention: 1 1H-NMR (DMSO-D6) δ: 8.79 (1H, d), 8.17 (1H, t), 7.85-7.82 (2H, m), 7.70-7.63 (2H, m), 7.43 (1H, d), 7.31-7.28 (1H, m), 7.09 (1H, d), 3.39-3.33 (2H, m), 1.72-1.63 (2H, m), 0.95 (3H, t). Compound IIA-130 of the present invention: 11H-NMR (DMSO-D6) δ: 8.79 (1H, d), 8.60 - 8.59 (1H, m), 8.29 (1H, dd), 7.85 - 7.81 (2H, m), 7.66 (1H, t), 7.35 (1H, d), 7.32 - 7.29 (1H, m), 7.09 (1H, d), 3.40 - 3.32 (2H, m), 1.72 - 1.63 (2H, m), 0.95 (3H, t). Compound IIA-132 of the present invention: 1 1H-NMR (CDCl3) δ: 7.98 (1H, d), 7.74 (1H, s), 7.63 (2H, t), 7.54 (1H, t), 7.44 - 7.40 (2H, m), 7.31 - 7.29 (1H, m), 7.02 - 6.98 (2H, m), 5.19 (2H, s), 3.33 - 3.29 (2H, m), 1.94 - 1.84 (2H, m), 1.06 (3H, t). Compound IIA-133 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.78 (1H, br s), 7.70 - 7.64 (2H, m), 7.53 (1H, t), 7.44 - 7.40 (2H, m), 7.32 - 7.29 (1H, m), 7.00 - 6.97 (2H, m), 5.17 (2H, s), 3.33 - 3.29 (2H, m), 1.94 - 1.84 (2H, m), 1.06 (3H, t). Compound IIA-134 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 (1H, d), 7.41 - 7.37 (2H, m), 7.32 (1H, t), 7.29 - 7.26 (1H, m), 7.04 - 6.97 (4H, m), 6.89 (1H, dd), 5.12 (2H, s), 3.83 (3H, s), 3.33 - 3.29 (2H, m), 1.93 - 1.84 (2H, m), 1.06 (3H, t). Compound IIA-135 of the present invention: 11H-NMR (CDCl3) δ: 7.95 (1H, d), 7.45 - 7.36 (5H, m), 7.20 - 7.15 (1H, m), 7.08 - 7.05 (2H, m), 7.01 - 6.99 (1H, m), 6.97 (1H, d), 3.32 - 3.28 (2H, m), 1.92 - 1.83 (2H, m), 1.05 (3H, t). Compound IIA-136 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.36 (1H, t), 7.26 - 7.23 (1H, m), 7.20 (1H, t), 6.97 (1H, d), 6.84 - 6.82 (1H, m), 4.75 - 4.68 (1H, m), 3.33 - 3.29 (2H, m), 2.52 - 2.45 (2H, m), 2.24 - 2.14 (2H, m), 1.94 - 1.84 (3H, m), 1.78 - 1.66 (1H, m), 1.05 (3H, t).

[0122]

Table 12

[0123]

Table 13

[0124]

Table 14

[0125] Production Example 6 A mixture of 1.03 g of 4-chlorobenzene thiocarboxamide, 0.92 g of S-ethyl 2-bromothioacetate, and 15 mL of ethanol was stirred at 80 °C for 8 hours. The resulting mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 98:2) to obtain 0.42 g of the compound IIB-1 of the present invention represented by the following formula. [Chemical formula] Compound IIB-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.89 (2H, m), 7.40 (2H, m), 7.04 (1H, s), 3.09 (2H, q), 1.37 (3H, t).

[0126] Production Example 6-1 The compounds produced according to Production Example 6 and their physical property values are shown below. Formula (B1) [Chemical formula] In the compound represented by, Z, R 1 , R 2 , R 3 , R 4 , R 5 , and R 8 The compound in which the combination of and is the combination described in [Table IIB1].

[0127] [Table 15] Compound IIB-2 of the present invention: 1 H-NMR (CDCl3) δ: 7.84 (2H, m), 7.23 (2H, m), 6.98 (1H, s), 3.05 (2H, m), 1.73 (2H, m), 1.04 (3H, t).

[0128] Production Example 7 To a mixture of 0.42 g of the compound IIB-1 of the present invention and 5 mL of chloroform, 1.2 g of mCPBA (purity 75%, 25% water content) was added at 0 °C, and the mixture was stirred at room temperature for 2 hours. An aqueous sodium sulfite solution was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 80:20) to obtain 93 mg of the compound IIB-3 of the present invention represented by the following formula. [Chemical formula] Compound IIB-3 of the present invention: 1 H-NMR (CDCl3) δ: 8.12 (1H, s), 7.93 (2H, m), 7.46 (2H, m), 3.40 (2H, q), 1.37 (3H, t).

[0129] Production Example 7-1 The compounds produced according to Production Example 7 and their physical property values are shown below. Formula (B3) [Chemical formula] In the compound represented by, Z, R 1 , R 2 , R 3 , R 4 , R 5 , and R 8 are compounds in which the combination is the combination described in [Table IIB3].

[0130]

Table 16

[0131] Reference Production Example 7 A mixture of 1.35 g of 4-fluoro-3-(trifluoromethyl)phenylacetyl bromide, 0.5 g of O-ethyl thiocarbamate, and 5 mL of ethanol was stirred at 85 °C for 5 hours. The resulting mixture was concentrated under reduced pressure. To the obtained residue, 5 mL of toluene and 0.73 g of Lawesson's reagent were sequentially added, and the mixture was stirred at 110 °C for 8 hours. Saturated brine was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.34 g of Intermediate MC1-1 represented by the following formula. [Chemical formula] Intermediate MC1-1: 1 1H-NMR (CDCl3) δ: 7.76 - 7.73 (1H, m), 7.71 - 7.67 (1H, m), 7.37 - 7.32 (1H, m), 6.73 (1H, s).

[0132] Reference Production Example 7-1 Using 4-fluoro-3-bromophenylacetyl bromide instead of 4-fluoro-3-(trifluoromethyl)phenylacetyl bromide, 1 g of Intermediate MC1-2 was obtained according to Reference Production Example 7. [Chemical formula] Intermediate MC1-2: 1 1H-NMR (CDCl3) δ: 7.66 (1H, dd), 7.28 - 7.25 (1H, m), 7.17 (1H, dd), 6.75 (1H, s).

[0133] Production Example 8 A mixture of 0.34 g of Intermediate MC1-1, 0.14 mL of 1-iodopropane, 0.25 g of potassium carbonate, and 5 mL of acetone was stirred at 80 °C for 5 hours. The resulting mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 40:60) to obtain 0.38 g of Compound IC-1 represented by the following formula. [Chemical formula] This compound IC-1: 1 H-NMR (CDCl3) δ: 8.13 - 8.11 (1H, m), 8.06 - 8.03 (1H, m), 7.35 (1H, s), 7.26 - 7.21 (1H, m), 3.26 (2H, t), 1.90 - 1.81 (2H, m), 1.11 - 1.07 (3H, m).

[0134] Production Example 8-1 The compounds produced according to Production Example 8 and their physical property values are shown below. Formula (C1)

Chemical Structure

[0135]

Table 17

[0136] This compound IC-2: 1 H-NMR (CDCl3) δ: 7.83 (2H, dt), 7.38 (2H, dt), 7.35 (1H, s), 3.77 - 3.69 (1H, m), 1.88 - 1.68 (2H, m), 1.47 (3H, d), 1.06 (3H, t). This compound IC-3: 1 H-NMR (CDCl3) δ: 7.85 - 7.81 (2H, m), 7.40 - 7.36 (2H, m), 7.36 (1H, s), 3.95 - 3.84 (1H, m), 1.48 (6H, d). This compound IC-4: 1H-NMR (CDCl3) δ: 7.82 (2H, dt), 7.20 (1H, s), 6.94 (2H, dt), 3.85 (3H, s), 3.24 (2H, t), 1.89 - 1.80 (2H, m), 1.08 (3H, t). IC-5 of this compound 1 H-NMR (CDCl3) δ: 7.79 - 7.76 (2H, m), 7.28 (1H, s), 7.22 - 7.20 (2H, m), 3.24 (2H, t), 2.38 (3H, s), 1.89 - 1.80 (2H, m), 1.08 (3H, t). IC-6 of this compound 1 H-NMR (CDCl3) δ: 7.93 - 7.89 (2H, m), 7.34 (1H, s), 7.26 - 7.24 (2H, m), 3.29 (2H, q), 1.48 (3H, t). IC-7 of this compound 1 H-NMR (CDCl3) δ: 7.78 - 7.74 (2H, m), 7.55 - 7.51 (2H, m), 7.34 (1H, s), 3.25 (2H, t), 1.89 - 1.80 (2H, m), 1.08 (3H, t). IC-8 of this compound 1 H-NMR (CDCl3) δ: 8.00 (1H, s), 7.70 (1H, d), 7.46 (1H, d), 7.36 (1H, s), 3.29 (2H, q), 1.48 (3H, t). IC-9 of this compound 1 H-NMR (CDCl3) δ: 7.79 (2H, d), 7.28 (1H, s), 7.22 (2H, d), 3.24 (2H, t), 2.63 (2H, t), 1.89 - 1.80 (2H, m), 1.65 - 1.58 (2H, m), 1.41 - 1.32 (2H, m), 1.07 (3H, t), 0.93 (3H, t). IC-10 of this compound 1H-NMR (CDCl3) δ: 7.80 (1H, dd), 7.66 (1H, d), 7.62 (1H, s), 7.37 (1H, t), 7.19 (1H, td), 3.24 (2H, t), 1.89 - 1.80 (2H, m), 1.07 (3H, t). Compound IC-11: 1 H-NMR (CDCl3) δ: 7.57 (1H, d), 7.27 - 7.21 (3H, m), 7.12 (1H, s), 3.24 (2H, t), 2.45 (3H, s), 1.88 - 1.79 (2H, m), 1.06 (3H, t). Compound IC-12: 1 H-NMR (CDCl3) δ: 8.00 (2H, d), 7.66 (2H, d), 7.45 (1H, d), 3.27 (2H, t), 1.91 - 1.82 (2H, m), 1.09 (3H, t). Compound IC-13: 1 H-NMR (CDCl3) δ: 7.81 (2H, d), 7.43 (2H, d), 7.29 (1H, s), 3.25 (2H, t), 1.89 - 1.80 (2H, m), 1.35 (9H, s), 1.07 (3H, t). Compound IC-14: 1 H-NMR (CDCl3) δ: 7.88 - 7.83 (2H, m), 7.27 (1H, s), 7.12 - 7.06 (2H, m), 3.25 (2H, t), 1.90 - 1.80 (2H, m), 1.08 (3H, t). Compound IC-15: 1H-NMR (CDCl3) δ: 8.05 (1H, s), 7.80 (1H, d), 7.45 (1H, d), 7.36 (1H, s), 7.27 (1H, t), 3.26 (2H, t), 1.90 - 1.80 (2H, m), 1.08 (3H, t). Compound IC-16: 1H-NMR (CDCl3) δ: 7.66 - 7.60 (2H, m), 7.39 - 7.34 (2H, m), 7.04 - 6.99 (1H, m), 3.30 (2H, q), 1.48 (3H, t). This compound IC-17: 1 H-NMR (CDCl3) δ: 7.66 - 7.59 (2H, m), 7.41 - 7.34 (2H, m), 7.04 - 6.99 (1H, m), 3.26 (2H, t), 1.90 - 1.81 (2H, m), 1.08 (3H, t). This compound IC-19: 1 H-NMR (CDCl3) δ: 7.56 - 7.53 (2H, m), 7.30 (1H, s), 7.22 - 7.18 (1H, m), 3.25 (2H, t), 2.30 (3H, s), 1.90 - 1.80 (2H, m), 1.08 (3H, t). This compound IC-20: 1 H-NMR (CDCl3) δ: 7.65 - 7.59 (2H, m), 7.40 - 7.35 (2H, m), 7.06 - 7.01 (1H, m), 3.48 (2H, t), 2.95 - 2.83 (2H, m). This compound IC-21: 1H-NMR (CDCl3) δ: 7.74 (2H, dt), 7.63 (2H, dt), 7.36 (1H, s), 3.28 (2H, q), 1.48 (3H, t). This compound IC-22: 1H-NMR (CDCl3) δ: 7.76 (2H, dt), 7.53 (2H, dt), 7.35 (1H, s), 3.28 (2H, q), 1.48 (3H, t). This compound IC-23: 1 H-NMR (CDCl3) δ: 7.68 (1H, dd), 7.59 - 7.52 (2H, m), 7.38 (1H, s), 3.29 (2H, q), 1.48 (3H, t). This compound IC-24: 11H-NMR (CDCl3) δ: 7.68 (1H, dd), 7.59-7.51 (2H, m), 7.37 (1H, s), 3.26 (2H, t), 1.90-1.81 (2H, m), 1.08 (3H, t).

[0137] Production Example 9 To a mixture of 0.2 g of this compound IC-26 and 5 mL of chloroform, 0.4 g of mCPBA (purity 75%, 25% water content) was added at 0 °C, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture, 10 mL of a saturated aqueous sodium thiosulfate solution was added and stirred for 1 hour, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 80:20) to obtain 0.2 g of the compound IIC-1 of the present invention represented by the following formula. [Chemical formula] Compound IIC-1 of the present invention: 1 1H-NMR (CDCl3) δ: 7.87 (2H, d), 7.82 (1H, s), 7.44 (2H, d), 3.51 (2H, q), 1.44 (3H, t).

[0138] Production Example 9-1 The compounds produced according to Production Example 9 and their physical property values are shown below. Formula (C3) [Chemical formula] In the compound represented by, Z, R 1 , R 2 , R 3 , R 4 , and R 5 wherein the combination of and is any combination described in [Table IIC3] and [Table IC3].

[0139] [Table 18] Compound IIC-2 of the present invention: 11H-NMR (CDCl3) δ: 7.89 - 7.86 (2H, m), 7.84 - 7.83 (1H, m), 7.45 - 7.42 (2H, m), 3.48 - 3.46 (1H, m), 2.17 - 2.14 (1H, m), 1.70 - 1.63 (1H, m), 1.45 (3H, d), 1.06 (3H, t). Compound IIC-3 of the present invention: 1 1H-NMR (CDCl3) δ: 7.87 (2H, d), 7.84 (1H, s), 7.45 - 7.41 (2H, m), 3.73 - 3.66 (1H, m), 1.47 (6H, d). Compound IIC-4 of the present invention: 1 1H-NMR (CDCl3) δ: 7.87 (2H, dt), 7.82 (1H, s), 7.44 (2H, dt), 3.48 - 3.44 (2H, m), 1.97 - 1.87 (2H, m), 1.08 (3H, t). Compound IIC-5 of the present invention: 1 1H-NMR (CDCl3) δ: 7.87 (2H, dt), 7.82 (1H, s), 7.44 (2H, dt), 3.50 - 3.46 (2H, m), 1.90 - 1.82 (2H, m), 1.53 - 1.43 (2H, m), 0.94 (3H, t). Compound IIC-6 of the present invention: 1 1H-NMR (CDCl3) δ: 7.86 (2H, dt), 7.68 (1H, s), 6.98 (2H, dt), 3.87 (3H, s), 3.47 - 3.43 (2H, m), 1.96 - 1.87 (2H, m), 1.08 (3H, t). Compound IIC-7 of the present invention: 1 1H-NMR (CDCl3) δ: 7.82 (2H, d), 7.76 (1H, s), 7.45 - 7.41 (2H, m), 3.48 - 3.44 (2H, m), 2.40 (3H, s), 1.96 - 1.87 (2H, m), 1.08 (3H, t). Compound IIC-8 of the present invention: 11H-NMR (CDCl3) δ: 7.96 (2H, dt), 7.84 (1H, s), 7.31 (2H, d), 3.51 (2H, q), 1.44 (3H, t). Compound IIC-9 of the present invention: 1 1H-NMR (CDCl3) δ: 7.83 (1H, s), 7.80 (2H, dt), 7.43 (2H, t), 3.48 - 3.44 (2H, m), 1.97 - 1.87 (2H, m), 1.08 (3H, t). Compound IIC-10 of the present invention: 1 1H-NMR (CDCl3) δ: 8.05 (1H, d), 7.86 (1H, s), 7.75 (1H, dd), 7.53 (1H, d), 3.52 (2H, q), 1.45 (3H, t). Compound IIC-11 of the present invention: 1 1H-NMR (CDCl3) δ: 7.83 (2H, d), 7.76 (1H, s), 7.30 - 7.28 (2H, m), 3.48 - 3.44 (2H, m), 2.66 (2H, t), 1.96 - 1.86 (2H, m), 1.66 - 1.59 (2H, m), 1.42 - 1.33 (2H, m), 1.07 (3H, t), 0.94 (3H, t). Compound IIC-12 of the present invention: 1 1H-NMR (CDCl3) δ: 8.13 (1H, s), 7.80 (1H, d), 7.70 (1H, d), 7.44 - 7.40 (1H, m), 7.29 - 7.27 (1H, m), 3.48 - 3.45 (2H, m), 1.97 - 1.88 (2H, m), 1.08 (3H, t). Compound IIC-13 of the present invention: 1 1H-NMR (CDCl3) δ: 8.17 (1H, dd), 8.11 (1H, m), 7.86 (1H, s), 7.31 (1H, t), 3.49 - 3.45 (2H, m), 1.97 - 1.88 (2H, m), 1.10 (3H, t). Compound IIC-14 of the present invention: 11H-NMR (CDCl3) δ: 8.08 (1H, t), 7.64 (1H, s), 7.59 - 7.56 (1H, m), 7.43 (1H, t), 7.36 - 7.28 (1H, m), 3.48 - 3.44 (2H, m), 2.46 (3H, s), 1.96 - 1.87 (2H, m), 1.07 (3H, t). Compound IIC-15 of the present invention: 1 1H-NMR (CDCl3) δ: 8.05 (2H, d), 7.94 (1H, s), 7.72 (2H, d), 3.49 - 3.45 (2H, m), 1.98 - 1.88 (2H, m), 1.09 (3H, t). Compound IIC-16 of the present invention: 1 1H-NMR (CDCl3) δ: 7.85 (2H, dt), 7.77 (1H, s), 7.48 (2H, dt), 3.48 - 3.44 (2H, m), 1.95 - 1.86 (2H, m), 1.36 (9H, s), 1.07 (3H, t). Compound IIC-17 of the present invention: 1 1H-NMR (CDCl3) δ: 7.93 - 7.90 (2H, m), 7.77 (1H, s), 7.18 - 7.13 (2H, m), 3.48 - 3.44 (2H, m), 1.97 - 1.88 (2H, m), 1.09 (3H, t). Compound IIC-18 of the present invention: 1 1H-NMR (CDCl3) δ: 8.10 (1H, s), 7.85 (1H, s), 7.84 (1H, d), 7.54 (1H, d), 7.34 (1H, t), 3.49 - 3.45 (2H, m), 1.97 - 1.87 (2H, m), 1.09 (3H, t). Compound IIC-19 of the present invention: 1 1H-NMR (CDCl3) δ: 7.66 - 7.60 (2H, m), 7.39 - 7.34 (2H, m), 7.04 - 6.99 (1H, m), 3.30 (2H, q), 1.48 (3H, t). Compound IIC-20 of the present invention: 11H-NMR (CDCl3) δ: 7.66 - 7.59 (2H, m), 7.39 - 7.34 (2H, m), 7.04 - 6.99 (1H, m), 3.26 (2H, t), 1.90 - 1.81 (2H, m), 1.08 (3H, t). Compound IIC-21 of the present invention: 1 1H-NMR (CDCl3) δ: 7.79 (1H, s), 7.60 - 7.57 (2H, m), 7.28 - 7.24 (1H, m), 3.51 (2H, q), 2.32 (3H, s), 1.44 (3H, t,). Compound IIC-22 of the present invention: 1 1H-NMR (CDCl3) δ: 7.78 (1H, s), 7.61 - 7.57 (2H, m), 7.28 - 7.24 (1H, m), 3.48 - 3.44 (2H, m), 2.33 (3H, s), 1.97 - 1.87 (2H, m), 1.08 (3H, t). Compound IIC-23 of the present invention: 1 1H-NMR (CDCl3) δ: 7.81 (1H, s), 7.66 - 7.63 (1H, m), 7.62 - 7.58 (1H, m), 7.45 - 7.39 (1H, m), 7.12 - 7.06 (1H, m), 3.52 - 3.35 (2H, m), 3.04 - 2.61 (2H, m). Compound IIC-24 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, s), 7.80 (2H, d), 7.66 (2H, d), 3.51 (2H, q), 1.44 (3H, t). Compound IIC-25 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, s), 7.80 (2H, d), 7.59 (2H, d), 3.51 (2H, q), 1.44 (3H, t). Compound IIC-26 of the present invention: 11H-NMR (CDCl3) δ: 7.87 (1H, s), 7.72 (1H, dd), 7.64 (1H, dd), 7.58 (1H, dd), 3.52 (2H, q), 1.45 (3H, t). Compound IIC-27 of the present invention: 1 1H-NMR (CDCl3) δ: 7.86 (1H, s), 7.72 (1H, dd), 7.64 (1H, dd), 7.58 (1H, dd), 3.48 - 3.44 (2H, m), 1.95 - 1.89 (2H, m), 1.09 (3H, t).

[0140] [Table 19] Compound IC-31 of the present invention: 1 1H-NMR (CDCl3) δ: 7.94 - 7.92 (2H, m), 7.83 (1H, s), 7.48 - 7.41 (3H, m), 3.49 - 3.45 (2H, m), 1.97 - 1.88 (2H, m), 1.08 (3H, t). Compound IC-32 of the present invention: 1 1H-NMR (CDCl3) δ: 7.94 - 7.91 (2H, m), 7.82 (1H, s), 7.49 - 7.39 (3H, m), 3.39 (3H, s).

[0141] Production Example 10 To a mixture of 0.30 g of Intermediate MA4-1, 0.16 mL of pyridine and 10 mL of chloroform, 0.18 g of ethyl chloroformate was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. Water was added to the obtained mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 60:40) to obtain 0.25 g of Compound IIA-137 of the present invention represented by the following formula. [Chemical formula] Compound IIA-137 of the present invention: 11H-NMR (CDCl3) δ: 7.88 (1H, d), 7.78 (1H, br s), 7.38 - 7.26 (3H, m), 6.70 (1H, br s), 6.40 (1H, d), 3.80 (3H, s), 3.01 (2H, m), 1.75 (2H, m), 1.04 (3H, t).

[0142] Production Example 10-1 The compounds produced according to Production Example 10 and their physical property values are shown below. Formula (A1) [Chemical formula] In the compound represented by, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 A compound in which the combination of is any of the combinations described in [Table IIA1-3].

[0143] [Table 20] Compound of the present invention IIA-138: 1 1H-NMR (CDCl3) δ: 7.88 (1H, d), 7.79 (1H, br s), 7.38 - 7.26 (3H, m), 6.68 (1H, br s), 6.39 (1H, d), 4.24 (2H, q), 3.01 (2H, m), 1.75 (2H, m), 1.33 (3H, t), 1.04 (3H, t). Compound of the present invention IIA-139: 1 1H-NMR (CDCl3) δ: 7.88 (1H, d), 7.80 (1H, br s), 7.38 - 7.26 (3H, m), 6.64 (1H, br s), 6.39 (1H, d), 5.03 (1H, m), 3.01 (2H, m), 1.75 (2H, m), 1.31 (6H, d), 1.04 (3H, t). Compound IIA-140 of the present invention: 1 H-NMR (CDCl3) δ: 7.81 (1H, d), 7.61 (2H, m), 7.45 (2H, m), 6.65 (1H, br s), 6.40 (1H, d), 3.79 (3H, s), 3.00 (2H, m), 1.75 (2H, m), 1.04 (3H, t). Compound IIA-141 of the present invention: 1 H-NMR (CDCl3) δ: 7.81 (1H, d), 7.60 (2H, m), 7.45 (2H, m), 6.62 (1H, br s), 6.39 (1H, d), 4.24 (2H, q), 3.00 (2H, m), 1.75 (2H, m), 1.32 (3H, t), 1.04 (3H, t). Compound IIA-142 of the present invention: 1 H-NMR (CDCl3) δ: 7.81 (1H, d), 7.60 (2H, m), 7.45 (2H, m), 6.58 (1H, br s), 6.40 (1H, d), 5.03 (1H, m), 3.00 (2H, m), 1.75 (2H, m), 1.31 (6H, d), 1.04 (3H, t).

[0144] Production Example 11 To a mixture of 0.5 g of Intermediate MA4-3, 0.32 mL of pyridine and 10 mL of chloroform, 0.24 g of acetyl chloride was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain 0.47 g of Compound IIA-179 of the present invention represented by the following formula.

Chemical formula

[0145] Production Example 11-1 The compounds produced according to Production Example 11 and their physical property values are shown below. Formula (A1)

Chemical formula

[0146]

Table 21

[0147] Production Example 12 A mixture of 0.26 g of Intermediate MA5-2, 0.16 g of p-toluidine, 0.38 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.24 g of 4-dimethylaminopyridine, and 10 mL of chloroform was stirred at room temperature for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 3:1) to obtain 0.29 g of Compound IIA-189 of the present invention represented by the following formula. [Chemical formula] Compound IIA-189 of the present invention: 1H-NMR (CDCl3) δ: 8.05 (1H, m), 7.93 (1H, d), 7.90 (1H, br s), 7.78 (2H, m), 7.60 (1H, m), 7.46 - 7.40 (2H, m), 7.31 (2H, m), 6.42 (1H, d), 3.01 (2H, t), 2.44 (3H, s), 1.76 (2H, m), 1.05 (3H, t).

[0148] Production Example 12-1 The compounds produced according to Production Example 12 and their physical property values are shown below. Formula (A1) [Chemical formula] In the compound represented by, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 A compound in which the combination of is any combination described in [Table IIA1-5].

[0149] [Table 22] Compound IIA-190 of the present invention: 1 H-NMR (CDCl3) δ: 8.18 (1H, m), 8.96 (1H, d), 7.90 (1H, br s), 7.83 (1H, m), 7.75 (1H, m), 7.58 - 7.53 (3H, m), 6.93 (2H, m), 6.45 (1H, d), 3.83 (3H, s), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t). Compound IIA-191 of the present invention: 11H-NMR (CDCl3) δ: 8.20 (1H, m), 7.98 (1H, br s), 7.96 (1H, d), 7.84 (1H, m), 7.76 (1H, m), 7.64 (2H, m), 7.57 (1H, t), 7.36 (2H, m), 6.47 (1H, d), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t). Compound IIA-192 of the present invention: 1 1H-NMR (CDCl3) δ: 8.18 (1H, m), 8.97 - 8.92 (2H, m), 7.87 - 7.81 (2H, m), 7.74 (1H, m), 7.56 (1H, t), 7.50 (1H, m), 7.31 (1H, t), 7.16 (1H, m), 6.46 (1H, d), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t). Compound IIA-193 of the present invention: 1 1H-NMR (CDCl3) δ: 7.66 (1H, d), 7.63 - 7.60 (2H, m), 7.27 - 7.07 (7H, m), 6.35 (1H, d), 3.52 (3H, s), 3.00 (2H, t), 1.74 (2H, m), 1.04 (3H, t). Compound IIA-194 of the present invention: 1 1H-NMR (CDCl3) δ: 8.05 (1H, m), 7.94 (1H, d), 7.80 (1H, m), 7.63 (1H, m), 7.49 (1H, t), 6.44 (1H, d), 6.36 (1H, br s), 3.01 (2H, t), 2.93 (1H, m), 1.75 (2H, m), 1.05 (3H, t), 0.90 (2H, m), 0.66 (2H, m). Compound IIA-195 of the present invention: 11H-NMR (CDCl3) δ: 8.08 (1H, m), 7.95 (1H, d), 7.81 (1H, m), 7.64 (1H, m), 7.50 (1H, t), 6.44 (1H, d), 6.23 (1H, br s), 3.45 (2H, m), 3.02 (2H, t), 1.76 (2H, m), 1.67 (2H, m), 1.05 (3H, t), 1.01 (3H, t). Compound IIA-196 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, m), 7.90 (1H, d), 7.81 (1H, m), 7.57 (1H, m), 7.48 (1H, t), 6.42 (1H, d), 3.58 (3H, s), 3.39 (3H, s), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t). Compound IIA-197 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97-7.93 (3H, m), 7.83 (1H, br s), 7.80 (2H, m), 7.65 (2H, m), 7.39 (2H, m), 7.17 (1H, m), 6.45 (1H, d), 3.05 (2H, t), 1.78 (2H, m), 1.06 (3H, t). Compound IIA-198 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.82 (2H, m), 7.72 (2H, m), 6.43 (1H, d), 6.27 (1H, br s), 3.03 (2H, t), 2.92 (1H, m), 1.77 (2H, m), 1.05 (3H, t), 0.89 (2H, m), 0.65 (2H, m). Compound IIA-199 of the present invention: 11H-NMR (CDCl3) δ: 7.92 (1H, d), 7.82 (2H, m), 7.71 (2H, m), 6.43 (1H, d), 3.56 (3H, s), 3.39 (3H, s), 3.04 (2H, t), 1.77 (2H, m), 1.05 (3H, t).

[0150] Production Example 13 To a mixture of 2.5 g of Intermediate MA6-1, 0.8 mL of pyridine, and 30 mL of chloroform, 1.1 mL of benzoyl chloride was added dropwise at 0 °C, and the mixture was stirred at 0 °C for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.3 g of the compound IIA-203 of the present invention represented by the following formula.

Chemical formula

[0151] Production Example 13-1 Instead of Intermediate MA6-1, Intermediate MA6-2 was used, and according to Production Example 13, the compound IIA-204 of the present invention represented by the following formula was obtained.

Chemical formula

[0152] Production Example 14 To a mixture of 1.1 g of the compound IIA-203 of the present invention, 0.6 g of potassium carbonate, and 15 mL of DMF, 0.6 g of iodomethane was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1) to obtain 1.1 g of the compound IIA-200 of the present invention represented by the following formula.

Chemical formula

[0153] Production Example 14-1 Instead of the compound IIA-203 of the present invention, the compound IIA-204 of the present invention was used, and according to Production Example 14, the compound IIA-201 of the present invention represented by the following formula was obtained.

Chemical formula

[0154] Production Example 15 To a mixture of 2.0 g of the compound IIA-40 of the present invention and 20 mL of THF, 3.2 mL of butyllithium (2.8 M, hexane solution) was added dropwise at -78°C, and the mixture was stirred at -78°C for 30 minutes. To the resulting mixture, a mixture of 3.1 g of N-fluorobis(phenylsulfonyl)amine and 20 mL of THF was added at -78°C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 20:1) to obtain 1.2 g of the compound IIA-202 of the present invention represented by the following formula.

Chemical formula

[0155] Examples of the present compound and the compound of the present invention produced according to the above production method and production examples are shown below.

[0156] Formula (L-1)

Chemical formula

[0157] Combination A consists of substituent numbers A1 to A2717. The substituent numbers A1 to A2717 refer to R 1C , R 2C , R 3C , R 4C , R 5C and Z C in the compound represented by formula (L-1), and are hereinafter denoted as [substituent number; R 1C , R 2C , R 3C , R 4C , R 5C , Z C . For example, the substituent number A5 refers to the combination in which R 1C , R 2C , R 4C and R 5C are each a hydrogen atom, R 3C is a methyl group, and Z C is an ethyl group.

[0158] Combination A [substituent number; R 1C , R 2C , R 3C , R 4C , R 5C , Z C : [A1;H,H,F,H,H,Et],[A2;H,H,Cl,H,H,Et],[A3;H,H,Br,H,H,Et],[A4;H,H,I,H,H,Et],[A5;H,H,Me,H,H,Et],[A6;H,H,OMe,H,H,Et],[A7;H,H,CF3,H,H,Et],[A8;H,H,CHF2,H,H,Et],[A9;H,H,NO2,H,H,Et],[A10;H,H,F,H,H,Pr],[A11;H,H,Cl,H,H,Pr],[A12;H,H,Br,H,H,Pr],[A13;H,H,I,H,H,Pr],[A14;H,H,Me,H,H,Pr],[A15;H,H,OMe,H,H,Pr],[A16;H,H,CF3,H,H,Pr],[A17;H,H,CHF2,H,H,Pr],[A18;H,H,NO2,H,H,Pr],[A19;H,H,F,H,H,i-Pr],[A20;H,H,Cl,H,H,i-Pr],[A21;H,H,Br,H,H,i-Pr],[A22;H,H,I,H,H,i-Pr],[A23;H,H,Me,H,H,i-Pr],[A24;H,H,OMe,H,H,i-Pr],[A25;H,H,CF3,H,H,i-Pr],[A26;H,H,CHF2,H,H,i-Pr],[A27;H,H,NO2,H,H,i-Pr],[A28;H,H,F,H,H,c-Pr],[A29;H,H,Cl,H,H,c-Pr],[A30;H,H,Br,H,H,c-Pr],[A31;H,H,I,H,H,c-Pr],[A32;H,H,Me,H,H,c-Pr],[A33;H,H,OMe,H,H,c-Pr],[A34;H,H,CF3,H,H,c-Pr],[A35;H,H,CHF2,H,H,c-Pr],[A36;H,H,NO2,H,H,c-Pr],[A37;H,H,F,H,H,Bu],[A38;H,H,Cl,H,H,Bu],[A39;H,H,Br,H,H,Bu],[A40;H,H,I,H,H,Bu],[A41;H,H,Me,H,H,Bu],[A42;H,H,OMe,H,H,Bu],[A43;H,H,CF3,H,H,Bu],[A44;H,H,CHF2,H,H,Bu],[A45;H,H,NO2,H,H,Bu],[A46;H,H,F,H,H,i-Bu],[A47;H,H,Cl,H,H,i-Bu],[A48;H, H, Br, H, H, i-Bu], [A49; H, H, I, H, H, i-Bu], [A50; H, H, Me, H, H, i-Bu], [A51; H, H, OMe, H, H, i-Bu], [A52; H, H, CF3, H, H, i-Bu], [A53; H, H, CHF2, H, H, i-Bu], [A54; H, H, NO2, H, H, i-Bu], [A55; H, H, F, H, H, CH2CF3], [A56; H, H, Cl, H, H, CH2CF3], [A57; H, H, Br, H, H, CH2CF3], [A58; H, H, I, H, H, CH2CF3], [A59; H, H, Me, H, H, CH2CF3], [A60; H, H, OMe, H, H, CH2CF3], [A61; H, H, CF3, H, H, CH2CF3], [A62; H, H, CHF2, H, H, CH2CF3], [A63; H, H, NO2, H, H, CH2CF3], [A64; H, H, F, H, H, CF2CH3], [A65; H, H, Cl, H, H, CF2CH3], [A66; H, H, Br, H, H, CF2CH3], [A67; H, H, I, H, H, CF2CH3], [A68; H, H, Me, H, H, CF2CH3], [A69; H, H, OMe, H, H, CF2CH3], [A70; H, H, CF3, H, H, CF2CH3], [A71; H, H, CHF2, H, H, CF2CH3], [A72; H, H, NO2, H, H, CF2CH3], [A73; H, H, F, H, H, 2-Py], [A74; H, H, Cl, H, H, 2-Py], [A75; H, H, Br, H, H, 2-Py], [A76; H, H, I, H, H, 2-Py], [A77; H, H, Me, H, H, 2-Py], [A78; H, H, OMe, H, H, 2-Py], [A79; H, H, CF3, H, H, 2-Py], [A80; H, H, CHF2, H, H, 2-Py], [A81; H, H, NO2, H, H, 2-Py], [A82; H, H, F, H, H, 3-Py], [A83; H, H, Cl, H, H, 3-Py], [A84; H, H, Br, H, H, 3-Py], [A85; H, H, I, H, H, 3-Py], [A86; H, H, Me, H, H, 3-Py], [A87; H, H, OMe, H, H, 3-Py], [A88; H, H, CF3, H, H, 3-Py], [A89; H, H, CHF2, H, H, 3-Py], [A90; H, H, NO2, H, H, 3-Py], [A91;H,H,F,H,H,4-Py],[A92;H,H,Cl,H,H,4-Py],[A93;H,H,Br,H,H,4-Py],[A94;H,H,I,H,H,4-Py],[A95;H,H,Me,H,H,4-Py],[A96;H,H,OMe,H,H,4-Py],[A97;H,H,CF3,H,H,4-Py],[A98;H,H,CHF2,H,H,4-Py],[A99;H,H,NO2,H,H,4-Py],[A100;H,F,H,H,H,Et],; [A101;H,F,F,H,H,Et],[A102;H,F,Cl,H,H,Et],[A103;H,F,Br,H,H,Et],[A104;H,F,I,H,H,Et],[A105;H,F,Me,H,H,Et],[A106;H,F,OMe,H,H,Et],[A107;H,F,CF3,H,H,Et],[A108;H,F,CHF2,H,H,Et],[A109;H,F,NO2,H,H,Et],[A110;H,F,H,H,H,Pr],[A111;H,F,F,H,H,Pr],[A112;H,F,Cl,H,H,Pr],[A113;H,F,Br,H,H,Pr],[A114;H,F,I,H,H,Pr],[A115;H,F,Me,H,H,Pr],[A116;H,F,OMe,H,H,Pr],[A117;H,F,CF3,H,H,Pr],[A118;H,F,CHF2,H,H,Pr],[A119;H,F,NO2,H,H,Pr],[A120;H,F,H,H,H,i-Pr],[A121;H,F,F,H,H,i-Pr],[A122;H,F,Cl,H,H,i-Pr],[A123;H,F,Br,H,H,i-Pr],[A124;H,F,I,H,H,i-Pr],[A125;H,F,Me,H,H,i-Pr],[A126;H,F,OMe,H,H,i-Pr],[A127;H,F,CF3,H,H,i-Pr],[A128;H,F,CHF2,H,H,i-Pr],[A129;H,F,NO2,H,H,i-Pr],[A130;H,F,H,H,H,c-Pr],[A131;H,F,F,H,H,c-Pr],[A132;H,F,Cl,H,H,c-Pr],[A133;H,F,Br,H,H,c-Pr],[A134;H,F,I,H,H,c-Pr],[A135;H,F,Me,H,H,c-Pr],[A136;H,F,OMe,H,H,c-Pr],[A137;H,F,CF3,H,H,c-Pr],[A138;H,F,CHF2,H,H,c-Pr],[A139;H,F,NO2,H,H,c-Pr],[A140;H,F,H,H,H,Bu],[A141;H,F,F,H,H,Bu],[A142;H,F,Cl,H,H,Bu],[A143;H,F,Br,H,H,Bu],[A144;H,F,I,H,H,Bu],[A145;H,F,Me,H,H,Bu],[A146;[H, F, OMe, H, H, Bu], [A147; H, F, CF3, H, H, Bu], [A148; H, F, CHF2, H, H, Bu], [A149; H, F, NO2, H, H, Bu], [A150; H, F, H, H, H, i - Bu], [A151; H, F, F, H, H, i - Bu], [A152; H, F, Cl, H, H, i - Bu], [A153; H, F, Br, H, H, i - Bu], [A154; H, F, I, H, H, i - Bu], [A155; H, F, Me, H, H, i - Bu], [A156; H, F, OMe, H, H, i - Bu], [A157; H, F, CF3, H, H, i - Bu], [A158; H, F, CHF2, H, H, i - Bu], [A159; H, F, NO2, H, H, i - Bu], [A160; H, F, H, H, H, CH2CF3], [A161; H, F, F, H, H, CH2CF3], [A162; H, F, Cl, H, H, CH2CF3], [A163; H, F, Br, H, H, CH2CF3], [A164; H, F, I, H, H, CH2CF3], [A165; H, F, Me, H, H, CH2CF3], [A166; H, F, OMe, H, H, CH2CF3], [A167; H, F, CF3, H, H, CH2CF3], [A168; H, F, CHF2, H, H, CH2CF3], [A169; H, F, NO2, H, H, CH2CF3], [A170; H, F, H, H, H, CF2CH3], [A171; H, F, F, H, H, CF2CH3], [A172; H, F, Cl, H, H, CF2CH3], [A173; H, F, Br, H, H, CF2CH3], [A174; H, F, I, H, H, CF2CH3], [A175; H, F, Me, H, H, CF2CH3], [A176; H, F, OMe, H, H, CF2CH3], [A177; H, F, CF3, H, H, CF2CH3], [A178; H, F, CHF2, H, H, CF2CH3], [A179; H, F, NO2, H, H, CF2CH3], [A180; H, F, H, H, H, 2 - Py], [A181; H, F, F, H, H, 2 - Py], [A182; H, F, Cl, H, H, 2 - Py], [A183; H, F, Br, H, H, 2 - Py], [A184; H, F, I, H, H, 2 - Py], [A185; H, F, Me, H, H, 2 - Py], [A186; H, F, OMe, H, H, 2 - Py], [A187;H,F,CF3,H,H,2-Py],[A188;H,F,CHF2,H,H,2-Py],[A189;H,F,NO2,H,H,2-Py],[A190;H,F,H,H,H,3-Py],[A191;H,F,F,H,H,3-Py],[A192;H,F,Cl,H,H,3-Py],[A193;H,F,Br,H,H,3-Py],[A194;H,F,I,H,H,3-Py],[A195;H,F,Me,H,H,3-Py],[A196;H,F,OMe,H,H,3-Py],[A197;H,F,CF3,H,H,3-Py],[A198;H,F,CHF2,H,H,3-Py],[A199;H,F,NO2,H,H,3-Py],[A200;H,F,H,H,H,4-Py],[A201;H,F,F,H,H,4-Py],[A202;H,F,Cl,H,H,4-Py],[A203;H,F,Br,H,H,4-Py],[A204;H,F,I,H,H,4-Py],[A205;H,F,Me,H,H,4-Py],[A206;H,F,OMe,H,H,4-Py],[A207;H,F,CF3,H,H,4-Py],[A208;H,F,CHF2,H,H,4-Py],[A209;H,F,NO2,H,H,4-Py],[A210;H,Cl,H,H,H,Et],[A211;H,Cl,F,H,H,Et],; [A212; H, Cl, Cl, H, H, Et], [A213; H, Cl, Br, H, H, Et], [A214; H, Cl, I, H, H, Et], [A215; H, Cl, Me, H, H, Et], [A216; H, Cl, OMe, H, H, Et], [A217; H, Cl, CF3, H, H, Et], [A218; H, Cl, CHF2, H, H, Et], [A219; H, Cl, NO2, H, H, Et], [A220; H, Cl, H, H, H, Pr], [A221; H, Cl, F, H, H, Pr], [A222; H, Cl, Cl, H, H, Pr], [A223; H, Cl, Br, H, H, Pr], [A224; H, Cl, I, H, H, Pr], [A225; H, Cl, Me, H, H, Pr], [A226; H, Cl, OMe, H, H, Pr], [A227; H, Cl, CF3, H, H, Pr], [A228; H, Cl, CHF2, H, H, Pr], [A229; H, Cl, NO2, H, H, Pr], [A230; H, Cl, H, H, H, i-Pr], [A231; H, Cl, F, H, H, i-Pr], [A232; H, Cl, Cl, H, H, i-Pr], [A233; H, Cl, Br, H, H, i-Pr], [A234; H, Cl, I, H, H, i-Pr], [A235; H, Cl, Me, H, H, i-Pr], [A236; H, Cl, OMe, H, H, i-Pr], [A237; H, Cl, CF3, H, H, i-Pr], [A238; H, Cl, CHF2, H, H, i-Pr], [A239; H, Cl, NO2, H, H, i-Pr], [A240; H, Cl, H, H, H, c-Pr], [A241; H, Cl, F, H, H, c-Pr], [A242; H, Cl, Cl, H, H, c-Pr], [A243; H, Cl, Br, H, H, c-Pr], [A244; H, Cl, I, H, H, c-Pr], [A245; H, Cl, Me, H, H, c-Pr], [A246; H, Cl, OMe, H, H, c-Pr], [A247; H, Cl, CF3, H, H, c-Pr], [A248; H, Cl, CHF2, H, H, c-Pr], [A249; H, Cl, NO2, H, H, c-Pr], [A250; H, Cl, H, H, H, Bu], [A251; H, Cl, F, H, H, Bu], [A252; H, Cl, Cl, H, H, Bu], [A253; H, Cl, Br, H, H, Bu], [A254; H, Cl, I, H, H, Bu], [A255;H, Cl, Me, H, H, Bu], [A256; H, Cl, OMe, H, H, Bu], [A257; H, Cl, CF3, H, H, Bu], [A258; H, Cl, CHF2, H, H, Bu], [A259; H, Cl, NO2, H, H, Bu], [A260; H, Cl, H, H, H, i - Bu], [A261; H, Cl, F, H, H, i - Bu], [A262; H, Cl, Cl, H, H, i - Bu], [A263; H, Cl, Br, H, H, i - Bu], [A264; H, Cl, I, H, H, i - Bu], [A265; H, Cl, Me, H, H, i - Bu], [A266; H, Cl, OMe, H, H, i - Bu], [A267; H, Cl, CF3, H, H, i - Bu], [A268; H, Cl, CHF2, H, H, i - Bu], [A269; H, Cl, NO2, H, H, i - Bu], [A270; H, Cl, H, H, H, CH2CF3], [A271; H, Cl, F, H, H, CH2CF3], [A272; H, Cl, Cl, H, H, CH2CF3], [A273; H, Cl, Br, H, H, CH2CF3], [A274; H, Cl, I, H, H, CH2CF3], [A275; H, Cl, Me, H, H, CH2CF3], [A276; H, Cl, OMe, H, H, CH2CF3], [A277; H, Cl, CF3, H, H, CH2CF3], [A278; H, Cl, CHF2, H, H, CH2CF3], [A279; H, Cl, NO2, H, H, CH2CF3], [A280; H, Cl, H, H, H, CF2CH3], [A281; H, Cl, F, H, H, CF2CH3], [A282; H, Cl, Cl, H, H, CF2CH3], [A283; H, Cl, Br, H, H, CF2CH3], [A284; H, Cl, I, H, H, CF2CH3], [A285; H, Cl, Me, H, H, CF2CH3], [A286; H, Cl, OMe, H, H, CF2CH3], [A287; H, Cl, CF3, H, H, CF2CH3], [A288; H, Cl, CHF2, H, H, CF2CH3], [A289; H, Cl, NO2, H, H, CF2CH3], [A290; H, Cl, H, H, H, 2 - Py], [A291; H, Cl, F, H, H, 2 - Py], [A292; H, Cl, Cl, H, H, 2 - Py], [A293; H, Cl, Br, H, H, 2 - Py], [A294; H, Cl, I, H, H, 2 - Py], [A295;H, Cl, Me, H, H, 2-Py], [A296; H, Cl, OMe, H, H, 2-Py], [A297; H, Cl, CF3, H, H, 2-Py], [A298; H, Cl, CHF2, H, H, 2-Py], [A299; H, Cl, NO2, H, H, 2-Py], [A300; H, Cl, H, H, H, 3-Py], [A301; H, Cl, F, H, H, 3-Py], [A302; H, Cl, Cl, H, H, 3-Py], [A303; H, Cl, Br, H, H, 3-Py], [A304; H, Cl, I, H, H, 3-Py], [A305; H, Cl, Me, H, H, 3-Py], [A306; H, Cl, OMe, H, H, 3-Py], [A307; H, Cl, CF3, H, H, 3-Py], [A308; H, Cl, CHF2, H, H, 3-Py], [A309; H, Cl, NO2, H, H, 3-Py], [A310; H, Cl, H, H, H, 4-Py], [A311; H, Cl, F, H, H, 4-Py], [A312; H, Cl, Cl, H, H, 4-Py], [A313; H, Cl, Br, H, H, 4-Py], [A314; H, Cl, I, H, H, 4-Py], [A315; H, Cl, Me, H, H, 4-Py], [A316; H, Cl, OMe, H, H, 4-Py], [A317; H, Cl, CF3, H, H, 4-Py], [A318; H, Cl, CHF2, H, H, 4-Py], [A319; H, Cl, NO2, H, H, 4-Py], [A320; H, Br, H, H, H, Et], [A321; H, Br, F, H, H, Et], [A322; H, Br, Cl, H, H, Et], [A323; H, Br, Br, H, H, Et], [A324; H, Br, I, H, H, Et], [A325; H, Br, Me, H, H, Et], [A326; H, Br, OMe, H, H, Et], [A327; H, Br, CF3, H, H, Et], [A328; H, Br, CHF2, H, H, Et], [A329; H, Br, NO2, H, H, Et], [A330; H, Br, H, H, H, Pr], [A331; H, Br, F, H, H, Pr], [A332; H, Br, Cl, H, H, Pr], [A333; H, Br, Br, H, H, Pr], [A334; H, Br, I, H, H, Pr], [A335; H, Br, Me, H, H, Pr], [A336; H, Br, OMe, H, H, Pr], [A337;H, Br, CF3, H, H, Pr], [A338; H, Br, CHF2, H, H, Pr], [A339; H, Br, NO2, H, H, Pr], [A340; H, Br, H, H, H, i-Pr], [A341; H, Br, F, H, H, i-Pr], [A342; H, Br, Cl, H, H, i-Pr], ; [A343; H, Br, Br, H, H, i-Pr], [A344; H, Br, I, H, H, i-Pr], [A345; H, Br, Me, H, H, i-Pr], [A346; H, Br, OMe, H, H, i-Pr], [A347; H, Br, CF3, H, H, i-Pr], [A348; H, Br, CHF2, H, H, i-Pr], [A349; H, Br, NO2, H, H, i-Pr], [A350; H, Br, H, H, H, c-Pr], [A351; H, Br, F, H, H, c-Pr], [A352; H, Br, Cl, H, H, c-Pr], [A353; H, Br, Br, H, H, c-Pr], [A354; H, Br, I, H, H, c-Pr], [A355; H, Br, Me, H, H, c-Pr], [A356; H, Br, OMe, H, H, c-Pr], [A357; H, Br, CF3, H, H, c-Pr], [A358; H, Br, CHF2, H, H, c-Pr], [A359; H, Br, NO2, H, H, c-Pr], [A360; H, Br, H, H, H, Bu], [A361; H, Br, F, H, H, Bu], [A362; H, Br, Cl, H, H, Bu], [A363; H, Br, Br, H, H, Bu], [A364; H, Br, I, H, H, Bu], [A365; H, Br, Me, H, H, Bu], [A366; H, Br, OMe, H, H, Bu], [A367; H, Br, CF3, H, H, Bu], [A368; H, Br, CHF2, H, H, Bu], [A369; H, Br, NO2, H, H, Bu], [A370; H, Br, H, H, H, i-Bu], [A371; H, Br, F, H, H, i-Bu], [A372; H, Br, Cl, H, H, i-Bu], [A373; H, Br, Br, H, H, i-Bu], [A374; H, Br, I, H, H, i-Bu], [A375; H, Br, Me, H, H, i-Bu], [A376; H, Br, OMe, H, H, i-Bu], [A377; H, Br, CF3, H, H, i-Bu], [A378; H, Br, CHF2, H, H, i-Bu], [A379; H, Br, NO2, H, H, i-Bu], [A380; H, Br, H, H, H, CH2CF3], [A381; H, Br, F, H, H, CH2CF3], [A382; H, Br, Cl, H, H, CH2CF3], [A383; H, Br, Br, H, H, CH2CF3], [A384;H, Br, I, H, H, CH2CF3], [A385; H, Br, Me, H, H, CH2CF3], [A386; H, Br, OMe, H, H, CH2CF3], [A387; H, Br, CF3, H, H, CH2CF3], [A388; H, Br, CHF2, H, H, CH2CF3], [A389; H, Br, NO2, H, H, CH2CF3], [A390; H, Br, H, H, H, CF2CH3], [A391; H, Br, F, H, H, CF2CH3], [A392; H, Br, Cl, H, H, CF2CH3], [A393; H, Br, Br, H, H, CF2CH3], [A394; H, Br, I, H, H, CF2CH3], [A395; H, Br, Me, H, H, CF2CH3], [A396; H, Br, OMe, H, H, CF2CH3], [A397; H, Br, CF3, H, H, CF2CH3], [A398; H, Br, CHF2, H, H, CF2CH3], [A399; H, Br, NO2, H, H, CF2CH3], [A400; H, Br, H, H, H, 2-Py], [A401; H, Br, F, H, H, 2-Py], [A402; H, Br, Cl, H, H, 2-Py], [A403; H, Br, Br, H, H, 2-Py], [A404; H, Br, I, H, H, 2-Py], [A405; H, Br, Me, H, H, 2-Py], [A406; H, Br, OMe, H, H, 2-Py], [A407; H, Br, CF3, H, H, 2-Py], [A408; H, Br, CHF2, H, H, 2-Py], [A409; H, Br, NO2, H, H, 2-Py], [A410; H, Br, H, H, H, 3-Py], [A411; H, Br, F, H, H, 3-Py], [A412; H, Br, Cl, H, H, 3-Py], [A413; H, Br, Br, H, H, 3-Py], [A414; H, Br, I, H, H, 3-Py], [A415; H, Br, Me, H, H, 3-Py], [A416; H, Br, OMe, H, H, 3-Py], [A417; H, Br, CF3, H, H, 3-Py], [A418; H, Br, CHF2, H, H, 3-Py], [A419; H, Br, NO2, H, H, 3-Py], [A420; H, Br, H, H, H, 4-Py], [A421; H, Br, F, H, H, 4-Py], [A422; H, Br, Cl, H, H, 4-Py], [A423; H, Br, Br, H, H, 4-Py], [A424;H, Br, I, H, H, 4-Py], [A425; H, Br, Me, H, H, 4-Py], [A426; H, Br, OMe, H, H, 4-Py], [A427; H, Br, CF3, H, H, 4-Py], [A428; H, Br, CHF2, H, H, 4-Py], [A429; H, Br, NO2, H, H, 4-Py], [A430; H, CF3, H, H, H, Et], [A431; H, CF3, F, H, H, Et], [A432; H, CF3, Cl, H, H, Et], [A433; H, CF3, Br, H, H, Et], [A434; H, CF3, I, H, H, Et], [A435; H, CF3, Me, H, H, Et], [A436; H, CF3, OMe, H, H, Et], [A437; H, CF3, CF3, H, H, Et], [A438; H, CF3, CHF2, H, H, Et], [A439; H, CF3, NO2, H, H, Et], [A440; H, CF3, H, H, H, Pr], [A441; H, CF3, F, H, H, Pr], [A442; H, CF3, Cl, H, H, Pr], [A443; H, CF3, Br, H, H, Pr], [A444; H, CF3, I, H, H, Pr], [A445; H, CF3, Me, H, H, Pr], [A446; H, CF3, OMe, H, H, Pr], [A447; H, CF3, CF3, H, H, Pr], [A448; H, CF3, CHF2, H, H, Pr], [A449; H, CF3, NO2, H, H, Pr], [A450; H, CF3, H, H, H, i-Pr], [A451; H, CF3, F, H, H, i-Pr], [A452; H, CF3, Cl, H, H, i-Pr], [A453; H, CF3, Br, H, H, i-Pr], [A454; H, CF3, I, H, H, i-Pr], [A455; H, CF3, Me, H, H, i-Pr], [A456; H, CF3, OMe, H, H, i-Pr], [A457; H, CF3, CF3, H, H, i-Pr], [A458; H, CF3, CHF2, H, H, i-Pr], [A459; H, CF3, NO2, H, H, i-Pr], [A460; H, CF3, H, H, H, c-Pr], [A461; H, CF3, F, H, H, c-Pr], [A462; H, CF3, Cl, H, H, c-Pr], [A463; H, CF3, Br, H, H, c-Pr], [A464; H, CF3, I, H, H, c-Pr], [A465;H, CF3, Me, H, H, c-Pr], [A466; H, CF3, OMe, H, H, c-Pr], [A467; H, CF3, CF3, H, H, c-Pr], [A468; H, CF3, CHF2, H, H, c-Pr], [A469; H, CF3, NO2, H, H, c-Pr], [A470; H, CF3, H, H, H, Bu], [A471; H, CF3, F, H, H, Bu], [A472; H, CF3, Cl, H, H, Bu], [A473; H, CF3, Br, H, H, Bu], [A474; H, CF3, I, H, H, Bu], [A475; H, CF3, Me, H, H, Bu], [A476; H, CF3, OMe, H, H, Bu], [A477; H, CF3, CF3, H, H, Bu], [A478; H, CF3, CHF2, H, H, Bu], [A479; H, CF3, NO2, H, H, Bu], [A480; H, CF3, H, H, H, i-Bu], [A481; H, CF3, F, H, H, i-Bu], [A482; H, CF3, Cl, H, H, i-Bu], [A483; H, CF3, Br, H, H, i-Bu], [A484; H, CF3, I, H, H, i-Bu], [A485; H, CF3, Me, H, H, i-Bu], [A486; H, CF3, OMe, H, H, i-Bu], [A487; H, CF3, CF3, H, H, i-Bu], [A488; H, CF3, CHF2, H, H, i-Bu], [A489; H, CF3, NO2, H, H, i-Bu], [A490; H, CF3, H, H, H, CH2CF3], [A491; H, CF3, F, H, H, CH2CF3], [A492; H, CF3, Cl, H, H, CH2CF3], [A493; H, CF3, Br, H, H, CH2CF3], ; [A494;H,CF3,I,H,H,CH2CF3],[A495;H,CF3,Me,H,H,CH2CF3],[A496;H,CF3,OMe,H,H,CH2CF3],[A497;H,CF3,CF3,H,H,CH2CF3],[A498;H,CF3,CHF2,H,H,CH2CF3],[A499;H,CF3,NO2,H,H,CH2CF3],[A500;H,CF3,H,H,H,CF2CH3],[A501;H,CF3,F,H,H,CF2CH3],[A502;H,CF3,Cl,H,H,CF2CH3],[A503;H,CF3,Br,H,H,CF2CH3],[A504;H,CF3,I,H,H,CF2CH3],[A505;H,CF3,Me,H,H,CF2CH3],[A506;H,CF3,OMe,H,H,CF2CH3],[A507;H,CF3,CF3,H,H,CF2CH3],[A508;H,CF3,CHF2,H,H,CF2CH3],[A509;H,CF3,NO2,H,H,CF2CH3],[A510;H,CF3,H,H,H,2-Py],[A511;H,CF3,F,H,H,2-Py],[A512;H,CF3,Cl,H,H,2-Py],[A513;H,CF3,Br,H,H,2-Py],[A514;H,CF3,I,H,H,2-Py],[A515;H,CF3,Me,H,H,2-Py],[A516;H,CF3,OMe,H,H,2-Py],[A517;H,CF3,CF3,H,H,2-Py],[A518;H,CF3,CHF2,H,H,2-Py],[A519;H,CF3,NO2,H,H,2-Py],[A520;H,CF3,H,H,H,3-Py],[A521;H,CF3,F,H,H,3-Py],[A522;H,CF3,Cl,H,H,3-Py],[A523;H,CF3,Br,H,H,3-Py],[A524;H,CF3,I,H,H,3-Py],[A525;H,CF3,Me,H,H,3-Py],[A526;H,CF3,OMe,H,H,3-Py],[A527;H,CF3,CF3,H,H,3-Py],[A528;H,CF3,CHF2,H,H,3-Py],[A529;H,CF3,NO2,H,H,3-Py],[A530;H,CF3,H,H,H,4-Py],[A531;H,CF3,F,H,H,4-Py],[A532;H, CF3, Cl, H, H, 4-Py], [A533; H, CF3, Br, H, H, 4-Py], [A534; H, CF3, I, H, H, 4-Py], [A535; H, CF3, Me, H, H, 4-Py], [A536; H, CF3, OMe, H, H, 4-Py], [A537; H, CF3, CF3, H, H, 4-Py], [A538; H, CF3, CHF2, H, H, 4-Py], [A539; H, CF3, NO2, H, H, 4-Py], [A540; H, NO2, H, H, H, Et], [A541; H, NO2, F, H, H, Et], [A542; H, NO2, Cl, H, H, Et], [A543; H, NO2, Br, H, H, Et], [A544; H, NO2, I, H, H, Et], [A545; H, NO2, Me, H, H, Et], [A546; H, NO2, OMe, H, H, Et], [A547; H, NO2, CF3, H, H, Et], [A548; H, NO2, CHF2, H, H, Et], [A549; H, NO2, NO2, H, H, Et], [A550; H, NO2, H, H, H, Pr], [A551; H, NO2, F, H, H, Pr], [A552; H, NO2, Cl, H, H, Pr], [A553; H, NO2, Br, H, H, Pr], [A554; H, NO2, I, H, H, Pr], [A555; H, NO2, Me, H, H, Pr], [A556; H, NO2, OMe, H, H, Pr], [A557; H, NO2, CF3, H, H, Pr], [A558; H, NO2, CHF2, H, H, Pr], [A559; H, NO2, NO2, H, H, Pr], [A560; H, NO2, H, H, H, i-Pr], [A561; H, NO2, F, H, H, i-Pr], [A562; H, NO2, Cl, H, H, i-Pr], [A563; H, NO2, Br, H, H, i-Pr], [A564; H, NO2, I, H, H, i-Pr], [A565; H, NO2, Me, H, H, i-Pr], [A566; H, NO2, OMe, H, H, i-Pr], [A567; H, NO2, CF3, H, H, i-Pr], [A568; H, NO2, CHF2, H, H, i-Pr], [A569; H, NO2, NO2, H, H, i-Pr], [A570; H, NO2, H, H, H, c-Pr], [A571; H, NO2, F, H, H, c-Pr], [A572; H, NO2, Cl, H, H, c-Pr], [A573;H, NO2, Br, H, H, c-Pr], [A574; H, NO2, I, H, H, c-Pr], [A575; H, NO2, Me, H, H, c-Pr], [A576; H, NO2, OMe, H, H, c-Pr], [A577; H, NO2, CF3, H, H, c-Pr], [A578; H, NO2, CHF2, H, H, c-Pr], [A579; H, NO2, NO2, H, H, c-Pr], [A580; H, NO2, H, H, H, Bu], [A581; H, NO2, F, H, H, Bu], [A582; H, NO2, Cl, H, H, Bu], [A583; H, NO2, Br, H, H, Bu], [A584; H, NO2, I, H, H, Bu], [A585; H, NO2, Me, H, H, Bu], [A586; H, NO2, OMe, H, H, Bu], [A587; H, NO2, CF3, H, H, Bu], [A588; H, NO2, CHF2, H, H, Bu], [A589; H, NO2, NO2, H, H, Bu], [A590; H, NO2, H, H, H, i-Bu], [A591; H, NO2, F, H, H, i-Bu], [A592; H, NO2, Cl, H, H, i-Bu], [A593; H, NO2, Br, H, H, i-Bu], [A594; H, NO2, I, H, H, i-Bu], [A595; H, NO2, Me, H, H, i-Bu], [A596; H, NO2, OMe, H, H, i-Bu], [A597; H, NO2, CF3, H, H, i-Bu], [A598; H, NO2, CHF2, H, H, i-Bu], [A599; H, NO2, NO2, H, H, i-Bu], [A600; H, NO2, H, H, H, CH2CF3], [A601; H, NO2, F, H, H, CH2CF3], [A602; H, NO2, Cl, H, H, CH2CF3], [A603; H, NO2, Br, H, H, CH2CF3], [A604; H, NO2, I, H, H, CH2CF3], [A605; H, NO2, Me, H, H, CH2CF3], [A606; H, NO2, OMe, H, H, CH2CF3], [A607; H, NO2, CF3, H, H, CH2CF3], [A608; H, NO2, CHF2, H, H, CH2CF3], [A609; H, NO2, NO2, H, H, CH2CF3], [A610; H, NO2, H, H, H, CF2CH3], [A611; H, NO2, F, H, H, CF2CH3], [A612;H, NO2, Cl, H, H, CF2CH3],; [A613; H, NO2, Br, H, H, CF2CH3], [A614; H, NO2, I, H, H, CF2CH3], [A615; H, NO2, Me, H, H, CF2CH3], [A616; H, NO2, OMe, H, H, CF2CH3], [A617; H, NO2, CF3, H, H, CF2CH3], [A618; H, NO2, CHF2, H, H, CF2CH3], [A619; H, NO2, NO2, H, H, CF2CH3], [A620; H, NO2, H, H, H, 2 - Py], [A621; H, NO2, F, H, H, 2 - Py], [A622; H, NO2, Cl, H, H, 2 - Py], [A623; H, NO2, Br, H, H, 2 - Py], [A624; H, NO2, I, H, H, 2 - Py], [A625; H, NO2, Me, H, H, 2 - Py], [A626; H, NO2, OMe, H, H, 2 - Py], [A627; H, NO2, CF3, H, H, 2 - Py], [A628; H, NO2, CHF2, H, H, 2 - Py], [A629; H, NO2, NO2, H, H, 2 - Py], [A630; H, NO2, H, H, H, 3 - Py], [A631; H, NO2, F, H, H, 3 - Py], [A632; H, NO2, Cl, H, H, 3 - Py], [A633; H, NO2, Br, H, H, 3 - Py], [A634; H, NO2, I, H, H, 3 - Py], [A635; H, NO2, Me, H, H, 3 - Py], [A636; H, NO2, OMe, H, H, 3 - Py], [A637; H, NO2, CF3, H, H, 3 - Py], [A638; H, NO2, CHF2, H, H, 3 - Py], [A639; H, NO2, NO2, H, H, 3 - Py], [A640; H, NO2, H, H, H, 4 - Py], [A641; H, NO2, F, H, H, 4 - Py], [A642; H, NO2, Cl, H, H, 4 - Py], [A643; H, NO2, Br, H, H, 4 - Py], [A644; H, NO2, I, H, H, 4 - Py], [A645; H, NO2, Me, H, H, 4 - Py], [A646; H, NO2, OMe, H, H, 4 - Py], [A647; H, NO2, CF3, H, H, 4 - Py], [A648; H, NO2, CHF2, H, H, 4 - Py], [A649; H, NO2, NO2, H, H, 4 - Py], [A650; H, OCH2Ph, H, H, H, Et], [A651;[H, OCH2Ph, F, H, H, Et], [A652; H, OCH2Ph, Cl, H, H, Et], [A653; H, OCH2Ph, Br, H, H, Et], [A654; H, OCH2Ph, I, H, H, Et], [A655; H, OCH2Ph, Me, H, H, Et], [A656; H, OCH2Ph, OMe, H, H, Et], [A657; H, OCH2Ph, CF3, H, H, Et], [A658; H, OCH2Ph, CHF2, H, H, Et], [A659; H, OCH2Ph, NO2, H, H, Et], [A660; H, OCH2Ph, H, H, H, Pr], [A661; H, OCH2Ph, F, H, H, Pr], [A662; H, OCH2Ph, Cl, H, H, Pr], [A663; H, OCH2Ph, Br, H, H, Pr], [A664; H, OCH2Ph, I, H, H, Pr], [A665; H, OCH2Ph, Me, H, H, Pr], [A666; H, OCH2Ph, OMe, H, H, Pr], [A667; H, OCH2Ph, CF3, H, H, Pr], [A668; H, OCH2Ph, CHF2, H, H, Pr], [A669; H, OCH2Ph, NO2, H, H, Pr], [A670; H, OCH2Ph, H, H, H, i-Pr], [A671; H, OCH2Ph, F, H, H, i-Pr], [A672; H, OCH2Ph, Cl, H, H, i-Pr], [A673; H, OCH2Ph, Br, H, H, i-Pr], [A674; H, OCH2Ph, I, H, H, i-Pr], [A675; H, OCH2Ph, Me, H, H, i-Pr], [A676; H, OCH2Ph, OMe, H, H, i-Pr], [A677; H, OCH2Ph, CF3, H, H, i-Pr], [A678; H, OCH2Ph, CHF2, H, H, i-Pr], [A679; H, OCH2Ph, NO2, H, H, i-Pr], [A680; H, OCH2Ph, H, H, H, c-Pr], [A681; H, OCH2Ph, F, H, H, c-Pr], [A682; H, OCH2Ph, Cl, H, H, c-Pr], [A683; H, OCH2Ph, Br, H, H, c-Pr], [A684; H, OCH2Ph, I, H, H, c-Pr], [A685; H, OCH2Ph, Me, H, H, c-Pr], [A686; H, OCH2Ph, OMe, H, H, c-Pr], [A687;[H, OCH2Ph, CF3, H, H, c-Pr], [A688]; [H, OCH2Ph, CHF2, H, H, c-Pr], [A689]; [H, OCH2Ph, NO2, H, H, c-Pr], [A690]; [H, OCH2Ph, H, H, H, Bu], [A691]; [H, OCH2Ph, F, H, H, Bu], [A692]; [H, OCH2Ph, Cl, H, H, Bu], [A693]; [H, OCH2Ph, Br, H, H, Bu], [A694]; [H, OCH2Ph, I, H, H, Bu], [A695]; [H, OCH2Ph, Me, H, H, Bu], [A696]; [H, OCH2Ph, OMe, H, H, Bu], [A697]; [H, OCH2Ph, CF3, H, H, Bu], [A698]; [H, OCH2Ph, CHF2, H, H, Bu], [A699]; [H, OCH2Ph, NO2, H, H, Bu], [A700]; [H, OCH2Ph, H, H, H, i-Bu], [A701]; [H, OCH2Ph, F, H, H, i-Bu], [A702]; [H, OCH2Ph, Cl, H, H, i-Bu], [A703]; [H, OCH2Ph, Br, H, H, i-Bu], [A704]; [H, OCH2Ph, I, H, H, i-Bu], [A705]; [H, OCH2Ph, Me, H, H, i-Bu], [A706]; [H, OCH2Ph, OMe, H, H, i-Bu], [A707]; [H, OCH2Ph, CF3, H, H, i-Bu], [A708]; [H, OCH2Ph, CHF2, H, H, i-Bu], [A709]; [H, OCH2Ph, NO2, H, H, i-Bu], [A710]; [H, OCH2Ph, H, H, H, CH2CF3], [A711]; [H, OCH2Ph, F, H, H, CH2CF3], [A712]; [H, OCH2Ph, Cl, H, H, CH2CF3], [A713]; [H, OCH2Ph, Br, H, H, CH2CF3], [A714]; [H, OCH2Ph, I, H, H, CH2CF3], [A715]; [H, OCH2Ph, Me, H, H, CH2CF3], [A716]; [H, OCH2Ph, OMe, H, H, CH2CF3], [A717]; [H, OCH2Ph, CF3, H, H, CH2CF3], [A718]; [H, OCH2Ph, CHF2, H, H, CH2CF3], [A719]; [H, OCH2Ph, NO2, H, H, CH2CF3], [A720]; [H, OCH2Ph, H, H, H, CF2CH3], [A721]; [H, OCH2Ph, F, H, H, CF2CH3], [A722;[H, OCH2Ph, Cl, H, H, CF2CH3], [A723; H, OCH2Ph, Br, H, H, CF2CH3], [A724; H, OCH2Ph, I, H, H, CF2CH3], [A725; H, OCH2Ph, Me, H, H, CF2CH3], [A726; H, OCH2Ph, OMe, H, H, CF2CH3], [A727; H, OCH2Ph, CF3, H, H, CF2CH3], [A728; H, OCH2Ph, CHF2, H, H, CF2CH3], [A729; H, OCH2Ph, NO2, H, H, CF2CH3], [A730; H, OCH2Ph, H, H, H, 2-Py], [A731; H, OCH2Ph, F, H, H, 2-Py], [A732; H, OCH2Ph, Cl, H, H, 2-Py], [A733; H, OCH2Ph, Br, H, H, 2-Py], [A734; H, OCH2Ph, I, H, H, 2-Py], [A735; H, OCH2Ph, Me, H, H, 2-Py], [A736; H, OCH2Ph, OMe, H, H, 2-Py], [A737; H, OCH2Ph, CF3, H, H, 2-Py], [A738; H, OCH2Ph, CHF2, H, H, 2-Py], [A739; H, OCH2Ph, NO2, H, H, 2-Py], [A740; H, OCH2Ph, H, H, H, 3-Py], [A741; H, OCH2Ph, F, H, H, 3-Py], [A742; H, OCH2Ph, Cl, H, H, 3-Py], ; [A743; H, OCH2Ph, Br, H, H, 3-Py], [A744; H, OCH2Ph, I, H, H, 3-Py], [A745; H, OCH2Ph, Me, H, H, 3-Py], [A746; H, OCH2Ph, OMe, H, H, 3-Py], [A747; H, OCH2Ph, CF3, H, H, 3-Py], [A748; H, OCH2Ph, CHF2, H, H, 3-Py], [A749; H, OCH2Ph, NO2, H, H, 3-Py], [A750; H, OCH2Ph, H, H, H, 4-Py], [A751; H, OCH2Ph, F, H, H, 4-Py], [A752; H, OCH2Ph, Cl, H, H, 4-Py], [A753; H, OCH2Ph, Br, H, H, 4-Py], [A754; H, OCH2Ph, I, H, H, 4-Py], [A755; H, OCH2Ph, Me, H, H, 4-Py], [A756; H, OCH2Ph, OMe, H, H, 4-Py], [A757; H, OCH2Ph, CF3, H, H, 4-Py], [A758; H, OCH2Ph, CHF2, H, H, 4-Py], [A759; H, OCH2Ph, NO2, H, H, 4-Py], [A760; H, F, H, F, H, Et], [A761; H, F, F, F, H, Et], [A762; H, F, Cl, F, H, Et], [A763; H, F, Br, F, H, Et], [A764; H, F, I, F, H, Et], [A765; H, F, Me, F, H, Et], [A766; H, F, OMe, F, H, Et], [A767; H, F, CF3, F, H, Et], [A768; H, F, CHF2, F, H, Et], [A769; H, F, NO2, F, H, Et], [A770; H, F, H, F, H, Pr], [A771; H, F, F, F, H, Pr], [A772; H, F, Cl, F, H, Pr], [A773; H, F, Br, F, H, Pr], [A774; H, F, I, F, H, Pr], [A775; H, F, Me, F, H, Pr], [A776; H, F, OMe, F, H, Pr], [A777; H, F, CF3, F, H, Pr], [A778; H, F, CHF2, F, H, Pr], [A779; H, F, NO2, F, H, Pr], [A780; H, F, H, F, H, i-Pr], [A781; H, F, F, F, H, i-Pr], [A782; H, F, Cl, F, H, i-Pr], [A783;H,F,Br,F,H,i-Pr],[A784;H,F,I,F,H,i-Pr],[A785;H,F,Me,F,H,i-Pr],[A786;H,F,OMe,F,H,i-Pr],[A787;H,F,CF3,F,H,i-Pr],[A788;H,F,CHF2,F,H,i-Pr],[A789;H,F,NO2,F,H,i-Pr],[A790;H,F,H,F,H,c-Pr],[A791;H,F,F,F,H,c-Pr],[A792;H,F,Cl,F,H,c-Pr],[A793;H,F,Br,F,H,c-Pr],[A794;H,F,I,F,H,c-Pr],[A795;H,F,Me,F,H,c-Pr],[A796;H,F,OMe,F,H,c-Pr],[A797;H,F,CF3,F,H,c-Pr],[A798;H,F,CHF2,F,H,c-Pr],[A799;H,F,NO2,F,H,c-Pr],[A800;H,F,H,F,H,Bu],[A801;H,F,F,F,H,Bu],[A802;H,F,Cl,F,H,Bu],[A803;H,F,Br,F,H,Bu],[A804;H,F,I,F,H,Bu],[A805;H,F,Me,F,H,Bu],[A806;H,F,OMe,F,H,Bu],[A807;H,F,CF3,F,H,Bu],[A808;H,F,CHF2,F,H,Bu],[A809;H,F,NO2,F,H,Bu],[A810;H,F,H,F,H,i-Bu],[A811;H,F,F,F,H,i-Bu],[A812;H,F,Cl,F,H,i-Bu],[A813;H,F,Br,F,H,i-Bu],[A814;H,F,I,F,H,i-Bu],[A815;H,F,Me,F,H,i-Bu],[A816;H,F,OMe,F,H,i-Bu],[A817;H,F,CF3,F,H,i-Bu],[A818;H,F,CHF2,F,H,i-Bu],[A819;H,F,NO2,F,H,i-Bu],[A820;H,F,H,F,H,CH2CF3],[A821;H,F,F,F,H,CH2CF3],[A822;H,F,Cl,F,H,CH2CF3],[A823;H,F,Br,F,H,CH2CF3],[A824;H,F,I,F,H,CH2CF3],[A825;H,F,Me,F,H,CH2CF3],[A826;[H,F,OMe,F,H,CH2CF3],[A827;H,F,CF3,F,H,CH2CF3],[A828;H,F,CHF2,F,H,CH2CF3],[A829;H,F,NO2,F,H,CH2CF3],[A830;H,F,H,F,H,CF2CH3],[A831;H,F,F,F,H,CF2CH3],[A832;H,F,Cl,F,H,CF2CH3],[A833;H,F,Br,F,H,CF2CH3],[A834;H,F,I,F,H,CF2CH3],[A835;H,F,Me,F,H,CF2CH3],[A836;H,F,OMe,F,H,CF2CH3],[A837;H,F,CF3,F,H,CF2CH3],[A838;H,F,CHF2,F,H,CF2CH3],[A839;H,F,NO2,F,H,CF2CH3],[A840;H,F,H,F,H,2-Py],[A841;H,F,F,F,H,2-Py],[A842;H,F,Cl,F,H,2-Py],[A843;H,F,Br,F,H,2-Py],[A844;H,F,I,F,H,2-Py],[A845;H,F,Me,F,H,2-Py],[A846;H,F,OMe,F,H,2-Py],[A847;H,F,CF3,F,H,2-Py],[A848;H,F,CHF2,F,H,2-Py],[A849;H,F,NO2,F,H,2-Py],[A850;H,F,H,F,H,3-Py],[A851;H,F,F,F,H,3-Py],[A852;H,F,Cl,F,H,3-Py],[A853;H,F,Br,F,H,3-Py],[A854;H,F,I,F,H,3-Py],[A855;H,F,Me,F,H,3-Py],[A856;H,F,OMe,F,H,3-Py],[A857;H,F,CF3,F,H,3-Py],[A858;H,F,CHF2,F,H,3-Py],[A859;H,F,NO2,F,H,3-Py],[A860;H,F,H,F,H,4-Py],[A861;H,F,F,F,H,4-Py],[A862;H,F,Cl,F,H,4-Py],[A863;H,F,Br,F,H,4-Py],[A864;H,F,I,F,H,4-Py],[A865;H,F,Me,F,H,4-Py],[A866;H,F,OMe,F,H,4-Py],[A867;H,F,CF3,F,H,4-Py],[A868;H,F,CHF2,F,H,4-Py],[A869;H,F,NO2,F,H,4-Py],; [A870;H,Cl,H,F,H,Et],[A871;H,Cl,F,F,H,Et],[A872;H,Cl,Cl,F,H,Et],[A873;H,Cl,Br,F,H,Et],[A874;H,Cl,I,F,H,Et],[A875;H,Cl,Me,F,H,Et],[A876;H,Cl,OMe,F,H,Et],[A877;H,Cl,CF3,F,H,Et],[A878;H,Cl,CHF2,F,H,Et],[A879;H,Cl,NO2,F,H,Et],[A880;H,Cl,H,F,H,Pr],[A881;H,Cl,F,F,H,Pr],[A882;H,Cl,Cl,F,H,Pr],[A883;H,Cl,Br,F,H,Pr],[A884;H,Cl,I,F,H,Pr],[A885;H,Cl,Me,F,H,Pr],[A886;H,Cl,OMe,F,H,Pr],[A887;H,Cl,CF3,F,H,Pr],[A888;H,Cl,CHF2,F,H,Pr],[A889;H,Cl,NO2,F,H,Pr],[A890;H,Cl,H,F,H,i-Pr],[A891;H,Cl,F,F,H,i-Pr],[A892;H,Cl,Cl,F,H,i-Pr],[A893;H,Cl,Br,F,H,i-Pr],[A894;H,Cl,I,F,H,i-Pr],[A895;H,Cl,Me,F,H,i-Pr],[A896;H,Cl,OMe,F,H,i-Pr],[A897;H,Cl,CF3,F,H,i-Pr],[A898;H,Cl,CHF2,F,H,i-Pr],[A899;H,Cl,NO2,F,H,i-Pr],[A900;H,Cl,H,F,H,c-Pr],[A901;H,Cl,F,F,H,c-Pr],[A902;H,Cl,Cl,F,H,c-Pr],[A903;H,Cl,Br,F,H,c-Pr],[A904;H,Cl,I,F,H,c-Pr],[A905;H,Cl,Me,F,H,c-Pr],[A906;H,Cl,OMe,F,H,c-Pr],[A907;H,Cl,CF3,F,H,c-Pr],[A908;H,Cl,CHF2,F,H,c-Pr],[A909;H,Cl,NO2,F,H,c-Pr],[A910;H,Cl,H,F,H,Bu],[A911;H,Cl,F,F,H,Bu],[A912;H,Cl,Cl,F,H,Bu],[A913;H, Cl, Br, F, H, Bu], [A914; H, Cl, I, F, H, Bu], [A915; H, Cl, Me, F, H, Bu], [A916; H, Cl, OMe, F, H, Bu], [A917; H, Cl, CF3, F, H, Bu], [A918; H, Cl, CHF2, F, H, Bu], [A919; H, Cl, NO2, F, H, Bu], [A920; H, Cl, H, F, H, i - Bu], [A921; H, Cl, F, F, H, i - Bu], [A922; H, Cl, Cl, F, H, i - Bu], [A923; H, Cl, Br, F, H, i - Bu], [A924; H, Cl, I, F, H, i - Bu], [A925; H, Cl, Me, F, H, i - Bu], [A926; H, Cl, OMe, F, H, i - Bu], [A927; H, Cl, CF3, F, H, i - Bu], [A928; H, Cl, CHF2, F, H, i - Bu], [A929; H, Cl, NO2, F, H, i - Bu], [A930; H, Cl, H, F, H, CH2CF3], [A931; H, Cl, F, F, H, CH2CF3], [A932; H, Cl, Cl, F, H, CH2CF3], [A933; H, Cl, Br, F, H, CH2CF3], [A934; H, Cl, I, F, H, CH2CF3], [A935; H, Cl, Me, F, H, CH2CF3], [A936; H, Cl, OMe, F, H, CH2CF3], [A937; H, Cl, CF3, F, H, CH2CF3], [A938; H, Cl, CHF2, F, H, CH2CF3], [A939; H, Cl, NO2, F, H, CH2CF3], [A940; H, Cl, H, F, H, CF2CH3], [A941; H, Cl, F, F, H, CF2CH3], [A942; H, Cl, Cl, F, H, CF2CH3], [A943; H, Cl, Br, F, H, CF2CH3], [A944; H, Cl, I, F, H, CF2CH3], [A945; H, Cl, Me, F, H, CF2CH3], [A946; H, Cl, OMe, F, H, CF2CH3], [A947; H, Cl, CF3, F, H, CF2CH3], [A948; H, Cl, CHF2, F, H, CF2CH3], [A949; H, Cl, NO2, F, H, CF2CH3], [A950; H, Cl, H, F, H, 2 - Py], [A951; H, Cl, F, F, H, 2 - Py], [A952; H, Cl, Cl, F, H, 2 - Py], [A953;H, Cl, Br, F, H, 2-Py], [A954; H, Cl, I, F, H, 2-Py], [A955; H, Cl, Me, F, H, 2-Py], [A956; H, Cl, OMe, F, H, 2-Py], [A957; H, Cl, CF3, F, H, 2-Py], [A958; H, Cl, CHF2, F, H, 2-Py], [A959; H, Cl, NO2, F, H, 2-Py], [A960; H, Cl, H, F, H, 3-Py], [A961; H, Cl, F, F, H, 3-Py], [A962; H, Cl, Cl, F, H, 3-Py], [A963; H, Cl, Br, F, H, 3-Py], [A964; H, Cl, I, F, H, 3-Py], [A965; H, Cl, Me, F, H, 3-Py], [A966; H, Cl, OMe, F, H, 3-Py], [A967; H, Cl, CF3, F, H, 3-Py], [A968; H, Cl, CHF2, F, H, 3-Py], [A969; H, Cl, NO2, F, H, 3-Py], [A970; H, Cl, H, F, H, 4-Py], [A971; H, Cl, F, F, H, 4-Py], [A972; H, Cl, Cl, F, H, 4-Py], [A973; H, Cl, Br, F, H, 4-Py], [A974; H, Cl, I, F, H, 4-Py], [A975; H, Cl, Me, F, H, 4-Py], [A976; H, Cl, OMe, F, H, 4-Py], [A977; H, Cl, CF3, F, H, 4-Py], [A978; H, Cl, CHF2, F, H, 4-Py], [A979; H, Cl, NO2, F, H, 4-Py], ; [A980;H,Br,H,F,H,Et],[A981;H,Br,F,F,H,Et],[A982;H,Br,Cl,F,H,Et],[A983;H,Br,Br,F,H,Et],[A984;H,Br,I,F,H,Et],[A985;H,Br,Me,F,H,Et],[A986;H,Br,OMe,F,H,Et],[A987;H,Br,CF3,F,H,Et],[A988;H,Br,CHF2,F,H,Et],[A989;H,Br,NO2,F,H,Et],[A990;H,Br,H,F,H,Pr],[A991;H,Br,F,F,H,Pr],[A992;H,Br,Cl,F,H,Pr],[A993;H,Br,Br,F,H,Pr],[A994;H,Br,I,F,H,Pr],[A995;H,Br,Me,F,H,Pr],[A996;H,Br,OMe,F,H,Pr],[A997;H,Br,CF3,F,H,Pr],[A998;H,Br,CHF2,F,H,Pr],[A999;H,Br,NO2,F,H,Pr],[A1000;H,Br,H,F,H,i-Pr],[A1001;H,Br,F,F,H,i-Pr],[A1002;H,Br,Cl,F,H,i-Pr],[A1003;H,Br,Br,F,H,i-Pr],[A1004;H,Br,I,F,H,i-Pr],[A1005;H,Br,Me,F,H,i-Pr],[A1006;H,Br,OMe,F,H,i-Pr],[A1007;H,Br,CF3,F,H,i-Pr],[A1008;H,Br,CHF2,F,H,i-Pr],[A1009;H,Br,NO2,F,H,i-Pr],[A1010;H,Br,H,F,H,c-Pr],[A1011;H,Br,F,F,H,c-Pr],[A1012;H,Br,Cl,F,H,c-Pr],[A1013;H,Br,Br,F,H,c-Pr],[A1014;H,Br,I,F,H,c-Pr],[A1015;H,Br,Me,F,H,c-Pr],[A1016;H,Br,OMe,F,H,c-Pr],[A1017;H,Br,CF3,F,H,c-Pr],[A1018;H,Br,CHF2,F,H,c-Pr],[A1019;H,Br,NO2,F,H,c-Pr],[A1020;H,Br,H,F,H,Bu],[A1021;H,Br,F,F,H,Bu],[A1022;H, Br, Cl, F, H, Bu], [A1023; H, Br, Br, F, H, Bu], [A1024; H, Br, I, F, H, Bu], [A1025; H, Br, Me, F, H, Bu], [A1026; H, Br, OMe, F, H, Bu], [A1027; H, Br, CF3, F, H, Bu], [A1028; H, Br, CHF2, F, H, Bu], [A1029; H, Br, NO2, F, H, Bu], [A1030; H, Br, H, F, H, i - Bu], [A1031; H, Br, F, F, H, i - Bu], [A1032; H, Br, Cl, F, H, i - Bu], [A1033; H, Br, Br, F, H, i - Bu], [A1034; H, Br, I, F, H, i - Bu], [A1035; H, Br, Me, F, H, i - Bu], [A1036; H, Br, OMe, F, H, i - Bu], [A1037; H, Br, CF3, F, H, i - Bu], [A1038; H, Br, CHF2, F, H, i - Bu], [A1039; H, Br, NO2, F, H, i - Bu], [A1040; H, Br, H, F, H, CH2CF3], [A1041; H, Br, F, F, H, CH2CF3], [A1042; H, Br, Cl, F, H, CH2CF3], [A1043; H, Br, Br, F, H, CH2CF3], [A1044; H, Br, I, F, H, CH2CF3], [A1045; H, Br, Me, F, H, CH2CF3], [A1046; H, Br, OMe, F, H, CH2CF3], [A1047; H, Br, CF3, F, H, CH2CF3], [A1048; H, Br, CHF2, F, H, CH2CF3], [A1049; H, Br, NO2, F, H, CH2CF3], [A1050; H, Br, H, F, H, CF2CH3], [A1051; H, Br, F, F, H, CF2CH3], [A1052; H, Br, Cl, F, H, CF2CH3], [A1053; H, Br, Br, F, H, CF2CH3], [A1054; H, Br, I, F, H, CF2CH3], [A1055; H, Br, Me, F, H, CF2CH3], [A1056; H, Br, OMe, F, H, CF2CH3], [A1057; H, Br, CF3, F, H, CF2CH3], [A1058; H, Br, CHF2, F, H, CF2CH3], [A1059; H, Br, NO2, F, H, CF2CH3], [A1060;H, Br, H, F, H, 2-Py], [A1061; H, Br, F, F, H, 2-Py], [A1062; H, Br, Cl, F, H, 2-Py], [A1063; H, Br, Br, F, H, 2-Py], [A1064; H, Br, I, F, H, 2-Py], [A1065; H, Br, Me, F, H, 2-Py], [A1066; H, Br, OMe, F, H, 2-Py], [A1067; H, Br, CF3, F, H, 2-Py], [A1068; H, Br, CHF2, F, H, 2-Py], [A1069; H, Br, NO2, F, H, 2-Py], [A1070; H, Br, H, F, H, 3-Py], [A1071; H, Br, F, F, H, 3-Py], [A1072; H, Br, Cl, F, H, 3-Py], [A1073; H, Br, Br, F, H, 3-Py], [A1074; H, Br, I, F, H, 3-Py], [A1075; H, Br, Me, F, H, 3-Py], [A1076; H, Br, OMe, F, H, 3-Py], [A1077; H, Br, CF3, F, H, 3-Py], [A1078; H, Br, CHF2, F, H, 3-Py], [A1079; H, Br, NO2, F, H, 3-Py], [A1080; H, Br, H, F, H, 4-Py], [A1081; H, Br, F, F, H, 4-Py], [A1082; H, Br, Cl, F, H, 4-Py], [A1083; H, Br, Br, F, H, 4-Py], [A1084; H, Br, I, F, H, 4-Py], [A1085; H, Br, Me, F, H, 4-Py], [A1086; H, Br, OMe, F, H, 4-Py], [A1087; H, Br, CF3, F, H, 4-Py], [A1088; H, Br, CHF2, F, H, 4-Py], [A1089; H, Br, NO2, F, H, 4-Py], ; [A1090;H,CF3,H,F,H,Et],[A1091;H,CF3,F,F,H,Et],[A1092;H,CF3,Cl,F,H,Et],[A1093;H,CF3,Br,F,H,Et],[A1094;H,CF3,I,F,H,Et],[A1095;H,CF3,Me,F,H,Et],[A1096;H,CF3,OMe,F,H,Et],[A1097;H,CF3,CF3,F,H,Et],[A1098;H,CF3,CHF2,F,H,Et],[A1099;H,CF3,NO2,F,H,Et],[A1100;H,CF3,H,F,H,Pr],[A1101;H,CF3,F,F,H,Pr],[A1102;H,CF3,Cl,F,H,Pr],[A1103;H,CF3,Br,F,H,Pr],[A1104;H,CF3,I,F,H,Pr],[A1105;H,CF3,Me,F,H,Pr],[A1106;H,CF3,OMe,F,H,Pr],[A1107;H,CF3,CF3,F,H,Pr],[A1108;H,CF3,CHF2,F,H,Pr],[A1109;H,CF3,NO2,F,H,Pr],[A1110;H,CF3,H,F,H,i-Pr],[A1111;H,CF3,F,F,H,i-Pr],[A1112;H,CF3,Cl,F,H,i-Pr],[A1113;H,CF3,Br,F,H,i-Pr],[A1114;H,CF3,I,F,H,i-Pr],[A1115;H,CF3,Me,F,H,i-Pr],[A1116;H,CF3,OMe,F,H,i-Pr],[A1117;H,CF3,CF3,F,H,i-Pr],[A1118;H,CF3,CHF2,F,H,i-Pr],[A1119;H,CF3,NO2,F,H,i-Pr],[A1120;H,CF3,H,F,H,c-Pr],[A1121;H,CF3,F,F,H,c-Pr],[A1122;H,CF3,Cl,F,H,c-Pr],[A1123;H,CF3,Br,F,H,c-Pr],[A1124;H,CF3,I,F,H,c-Pr],[A1125;H,CF3,Me,F,H,c-Pr],[A1126;H,CF3,OMe,F,H,c-Pr],[A1127;H,CF3,CF3,F,H,c-Pr],[A1128;H,CF3,CHF2,F,H,c-Pr],[A1129;H, CF3, NO2, F, H, c-Pr], [A1130; H, CF3, H, F, H, Bu], [A1131; H, CF3, F, F, H, Bu], [A1132; H, CF3, Cl, F, H, Bu], [A1133; H, CF3, Br, F, H, Bu], [A1134; H, CF3, I, F, H, Bu], [A1135; H, CF3, Me, F, H, Bu], [A1136; H, CF3, OMe, F, H, Bu], [A1137; H, CF3, CF3, F, H, Bu], [A1138; H, CF3, CHF2, F, H, Bu], [A1139; H, CF3, NO2, F, H, Bu], [A1140; H, CF3, H, F, H, i-Bu], [A1141; H, CF3, F, F, H, i-Bu], [A1142; H, CF3, Cl, F, H, i-Bu], [A1143; H, CF3, Br, F, H, i-Bu], [A1144; H, CF3, I, F, H, i-Bu], [A1145; H, CF3, Me, F, H, i-Bu], [A1146; H, CF3, OMe, F, H, i-Bu], [A1147; H, CF3, CF3, F, H, i-Bu], [A1148; H, CF3, CHF2, F, H, i-Bu], [A1149; H, CF3, NO2, F, H, i-Bu], [A1150; H, CF3, H, F, H, CH2CF3], [A1151; H, CF3, F, F, H, CH2CF3], [A1152; H, CF3, Cl, F, H, CH2CF3], [A1153; H, CF3, Br, F, H, CH2CF3], [A1154; H, CF3, I, F, H, CH2CF3], [A1155; H, CF3, Me, F, H, CH2CF3], [A1156; H, CF3, OMe, F, H, CH2CF3], [A1157; H, CF3, CF3, F, H, CH2CF3], [A1158; H, CF3, CHF2, F, H, CH2CF3], [A1159; H, CF3, NO2, F, H, CH2CF3], [A1160; H, CF3, H, F, H, CF2CH3], [A1161; H, CF3, F, F, H, CF2CH3], [A1162; H, CF3, Cl, F, H, CF2CH3], [A1163; H, CF3, Br, F, H, CF2CH3], [A1164; H, CF3, I, F, H, CF2CH3], [A1165; H, CF3, Me, F, H, CF2CH3], [A1166;H, CF3, OMe, F, H, CF2CH3], [A1167; H, CF3, CF3, F, H, CF2CH3], [A1168; H, CF3, CHF2, F, H, CF2CH3], [A1169; H, CF3, NO2, F, H, CF2CH3], [A1170; H, CF3, H, F, H, 2-Py], [A1171; H, CF3, F, F, H, 2-Py], [A1172; H, CF3, Cl, F, H, 2-Py], [A1173; H, CF3, Br, F, H, 2-Py], [A1174; H, CF3, I, F, H, 2-Py], [A1175; H, CF3, Me, F, H, 2-Py], [A1176; H, CF3, OMe, F, H, 2-Py], [A1177; H, CF3, CF3, F, H, 2-Py], [A1178; H, CF3, CHF2, F, H, 2-Py], [A1179; H, CF3, NO2, F, H, 2-Py], [A1180; H, CF3, H, F, H, 3-Py], [A1181; H, CF3, F, F, H, 3-Py], [A1182; H, CF3, Cl, F, H, 3-Py], [A1183; H, CF3, Br, F, H, 3-Py], [A1184; H, CF3, I, F, H, 3-Py], [A1185; H, CF3, Me, F, H, 3-Py], [A1186; H, CF3, OMe, F, H, 3-Py], [A1187; H, CF3, CF3, F, H, 3-Py], [A1188; H, CF3, CHF2, F, H, 3-Py], [A1189; H, CF3, NO2, F, H, 3-Py], [A1190; H, CF3, H, F, H, 4-Py], [A1191; H, CF3, F, F, H, 4-Py], [A1192; H, CF3, Cl, F, H, 4-Py], [A1193; H, CF3, Br, F, H, 4-Py], [A1194; H, CF3, I, F, H, 4-Py], [A1195; H, CF3, Me, F, H, 4-Py], [A1196; H, CF3, OMe, F, H, 4-Py], [A1197; H, CF3, CF3, F, H, 4-Py], [A1198; H, CF3, CHF2, F, H, 4-Py], [A1199; H, CF3, NO2, F, H, 4-Py], ; [A1200; H, NO2, H, F, H, Et], [A1201; H, NO2, F, F, H, Et], [A1202; H, NO2, Cl, F, H, Et], [A1203; H, NO2, Br, F, H, Et], [A1204; H, NO2, I, F, H, Et], [A1205; H, NO2, Me, F, H, Et], [A1206; H, NO2, OMe, F, H, Et], [A1207; H, NO2, CF3, F, H, Et], [A1208; H, NO2, CHF2, F, H, Et], [A1209; H, NO2, NO2, F, H, Et], [A1210; H, NO2, H, F, H, Pr], [A1211; H, NO2, F, F, H, Pr], [A1212; H, NO2, Cl, F, H, Pr], [A1213; H, NO2, Br, F, H, Pr], [A1214; H, NO2, I, F, H, Pr], [A1215; H, NO2, Me, F, H, Pr], [A1216; H, NO2, OMe, F, H, Pr], [A1217; H, NO2, CF3, F, H, Pr], [A1218; H, NO2, CHF2, F, H, Pr], [A1219; H, NO2, NO2, F, H, Pr], [A1220; H, NO2, H, F, H, i-Pr], [A1221; H, NO2, F, F, H, i-Pr], [A1222; H, NO2, Cl, F, H, i-Pr], [A1223; H, NO2, Br, F, H, i-Pr], [A1224; H, NO2, I, F, H, i-Pr], [A1225; H, NO2, Me, F, H, i-Pr], [A1226; H, NO2, OMe, F, H, i-Pr], [A1227; H, NO2, CF3, F, H, i-Pr], [A1228; H, NO2, CHF2, F, H, i-Pr], [A1229; H, NO2, NO2, F, H, i-Pr], [A1230; H, NO2, H, F, H, c-Pr], [A1231; H, NO2, F, F, H, c-Pr], [A1232; H, NO2, Cl, F, H, c-Pr], [A1233; H, NO2, Br, F, H, c-Pr], [A1234; H, NO2, I, F, H, c-Pr], [A1235; H, NO2, Me, F, H, c-Pr], [A1236; H, NO2, OMe, F, H, c-Pr], [A1237; H, NO2, CF3, F, H, c-Pr], [A1238; H, NO2, CHF2, F, H, c-Pr], [A1239;H, NO2, NO2, F, H, c-Pr], [A1240; H, NO2, H, F, H, Bu], [A1241; H, NO2, F, F, H, Bu], [A1242; H, NO2, Cl, F, H, Bu], [A1243; H, NO2, Br, F, H, Bu], [A1244; H, NO2, I, F, H, Bu], [A1245; H, NO2, Me, F, H, Bu], [A1246; H, NO2, OMe, F, H, Bu], [A1247; H, NO2, CF3, F, H, Bu], [A1248; H, NO2, CHF2, F, H, Bu], [A1249; H, NO2, NO2, F, H, Bu], [A1250; H, NO2, H, F, H, i-Bu], [A1251; H, NO2, F, F, H, i-Bu], [A1252; H, NO2, Cl, F, H, i-Bu], [A1253; H, NO2, Br, F, H, i-Bu], [A1254; H, NO2, I, F, H, i-Bu], [A1255; H, NO2, Me, F, H, i-Bu], [A1256; H, NO2, OMe, F, H, i-Bu], [A1257; H, NO2, CF3, F, H, i-Bu], [A1258; H, NO2, CHF2, F, H, i-Bu], [A1259; H, NO2, NO2, F, H, i-Bu], [A1260; H, NO2, H, F, H, CH2CF3], [A1261; H, NO2, F, F, H, CH2CF3], [A1262; H, NO2, Cl, F, H, CH2CF3], [A1263; H, NO2, Br, F, H, CH2CF3], [A1264; H, NO2, I, F, H, CH2CF3], [A1265; H, NO2, Me, F, H, CH2CF3], [A1266; H, NO2, OMe, F, H, CH2CF3], [A1267; H, NO2, CF3, F, H, CH2CF3], [A1268; H, NO2, CHF2, F, H, CH2CF3], [A1269; H, NO2, NO2, F, H, CH2CF3], [A1270; H, NO2, H, F, H, CF2CH3], [A1271; H, NO2, F, F, H, CF2CH3], [A1272; H, NO2, Cl, F, H, CF2CH3], [A1273; H, NO2, Br, F, H, CF2CH3], [A1274; H, NO2, I, F, H, CF2CH3], [A1275; H, NO2, Me, F, H, CF2CH3], [A1276;H, NO2, OMe, F, H, CF2CH3], [A1277; H, NO2, CF3, F, H, CF2CH3], [A1278; H, NO2, CHF2, F, H, CF2CH3], [A1279; H, NO2, NO2, F, H, CF2CH3], [A1280; H, NO2, H, F, H, 2-Py], [A1281; H, NO2, F, F, H, 2-Py], [A1282; H, NO2, Cl, F, H, 2-Py], [A1283; H, NO2, Br, F, H, 2-Py], [A1284; H, NO2, I, F, H, 2-Py], [A1285; H, NO2, Me, F, H, 2-Py], [A1286; H, NO2, OMe, F, H, 2-Py], [A1287; H, NO2, CF3, F, H, 2-Py], [A1288; H, NO2, CHF2, F, H, 2-Py], [A1289; H, NO2, NO2, F, H, 2-Py], [A1290; H, NO2, H, F, H, 3-Py], [A1291; H, NO2, F, F, H, 3-Py], [A1292; H, NO2, Cl, F, H, 3-Py], [A1293; H, NO2, Br, F, H, 3-Py], [A1294; H, NO2, I, F, H, 3-Py], [A1295; H, NO2, Me, F, H, 3-Py], [A1296; H, NO2, OMe, F, H, 3-Py], [A1297; H, NO2, CF3, F, H, 3-Py], [A1298; H, NO2, CHF2, F, H, 3-Py], [A1299; H, NO2, NO2, F, H, 3-Py], [A1300; H, NO2, H, F, H, 4-Py], [A1301; H, NO2, F, F, H, 4-Py], [A1302; H, NO2, Cl, F, H, 4-Py], [A1303; H, NO2, Br, F, H, 4-Py], [A1304; H, NO2, I, F, H, 4-Py], [A1305; H, NO2, Me, F, H, 4-Py], [A1306; H, NO2, OMe, F, H, 4-Py], [A1307; H, NO2, CF3, F, H, 4-Py], [A1308; H, NO2, CHF2, F, H, 4-Py], [A1309; H, NO2, NO2, F, H, 4-Py], ; [A1310;H,OCH2Ph,H,F,H,Et],[A1311;H,OCH2Ph,F,F,H,Et],[A1312;H,OCH2Ph,Cl,F,H,Et],[A1313;H,OCH2Ph,Br,F,H,Et],[A1314;H,OCH2Ph,I,F,H,Et],[A1315;H,OCH2Ph,Me,F,H,Et],[A1316;H,OCH2Ph,OMe,F,H,Et],[A1317;H,OCH2Ph,CF3,F,H,Et],[A1318;H,OCH2Ph,CHF2,F,H,Et],[A1319;H,OCH2Ph,NO2,F,H,Et],[A1320;H,OCH2Ph,H,F,H,Pr],[A1321;H,OCH2Ph,F,F,H,Pr],[A1322;H,OCH2Ph,Cl,F,H,Pr],[A1323;H,OCH2Ph,Br,F,H,Pr],[A1324;H,OCH2Ph,I,F,H,Pr],[A1325;H,OCH2Ph,Me,F,H,Pr],[A1326;H,OCH2Ph,OMe,F,H,Pr],[A1327;H,OCH2Ph,CF3,F,H,Pr],[A1328;H,OCH2Ph,CHF2,F,H,Pr],[A1329;H,OCH2Ph,NO2,F,H,Pr],[A1330;H,OCH2Ph,H,F,H,i-Pr],[A1331;H,OCH2Ph,F,F,H,i-Pr],[A1332;H,OCH2Ph,Cl,F,H,i-Pr],[A1333;H,OCH2Ph,Br,F,H,i-Pr],[A1334;H,OCH2Ph,I,F,H,i-Pr],[A1335;H,OCH2Ph,Me,F,H,i-Pr],[A1336;H,OCH2Ph,OMe,F,H,i-Pr],[A1337;H,OCH2Ph,CF3,F,H,i-Pr],[A1338;H,OCH2Ph,CHF2,F,H,i-Pr],[A1339;H,OCH2Ph,NO2,F,H,i-Pr],[A1340;H,OCH2Ph,H,F,H,c-Pr],[A1341;H,OCH2Ph,F,F,H,c-Pr],[A1342;H,OCH2Ph,Cl,F,H,c-Pr],[A1343;H,OCH2Ph,Br,F,H,c-Pr],[A1344;H,OCH2Ph,I,F,H,c-Pr],[A1345;[H, OCH2Ph, Me, F, H, c-Pr], [A1346]; [H, OCH2Ph, OMe, F, H, c-Pr], [A1347]; [H, OCH2Ph, CF3, F, H, c-Pr], [A1348]; [H, OCH2Ph, CHF2, F, H, c-Pr], [A1349]; [H, OCH2Ph, NO2, F, H, c-Pr], [A1350]; [H, OCH2Ph, H, F, H, Bu], [A1351]; [H, OCH2Ph, F, F, H, Bu], [A1352]; [H, OCH2Ph, Cl, F, H, Bu], [A1353]; [H, OCH2Ph, Br, F, H, Bu], [A1354]; [H, OCH2Ph, I, F, H, Bu], [A1355]; [H, OCH2Ph, Me, F, H, Bu], [A1356]; [H, OCH2Ph, OMe, F, H, Bu], [A1357]; [H, OCH2Ph, CF3, F, H, Bu], [A1358]; [H, OCH2Ph, CHF2, F, H, Bu], [A1359]; [H, OCH2Ph, NO2, F, H, Bu], [A1360]; [H, OCH2Ph, H, F, H, i-Bu], [A1361]; [H, OCH2Ph, F, F, H, i-Bu], [A1362]; [H, OCH2Ph, Cl, F, H, i-Bu], [A1363]; [H, OCH2Ph, Br, F, H, i-Bu], [A1364]; [H, OCH2Ph, I, F, H, i-Bu], [A1365]; [H, OCH2Ph, Me, F, H, i-Bu], [A1366]; [H, OCH2Ph, OMe, F, H, i-Bu], [A1367]; [H, OCH2Ph, CF3, F, H, i-Bu], [A1368]; [H, OCH2Ph, CHF2, F, H, i-Bu], [A1369]; [H, OCH2Ph, NO2, F, H, i-Bu], [A1370]; [H, OCH2Ph, H, F, H, CH2CF3], [A1371]; [H, OCH2Ph, F, F, H, CH2CF3], [A1372]; [H, OCH2Ph, Cl, F, H, CH2CF3], [A1373]; [H, OCH2Ph, Br, F, H, CH2CF3], [A1374]; [H, OCH2Ph, I, F, H, CH2CF3], [A1375]; [H, OCH2Ph, Me, F, H, CH2CF3], [A1376]; [H, OCH2Ph, OMe, F, H, CH2CF3], [A1377]; [H, OCH2Ph, CF3, F, H, CH2CF3], [A1378]; [H, OCH2Ph, CHF2, F, H, CH2CF3], [A1379;[H, OCH2Ph, NO2, F, H, CH2CF3], [A1380; H, OCH2Ph, H, F, H, CF2CH3], [A1381; H, OCH2Ph, F, F, H, CF2CH3], [A1382; H, OCH2Ph, Cl, F, H, CF2CH3], [A1383; H, OCH2Ph, Br, F, H, CF2CH3], [A1384; H, OCH2Ph, I, F, H, CF2CH3], [A1385; H, OCH2Ph, Me, F, H, CF2CH3], [A1386; H, OCH2Ph, OMe, F, H, CF2CH3], [A1387; H, OCH2Ph, CF3, F, H, CF2CH3], [A1388; H, OCH2Ph, CHF2, F, H, CF2CH3], [A1389; H, OCH2Ph, NO2, F, H, CF2CH3], [A1390; H, OCH2Ph, H, F, H, 2-Py], [A1391; H, OCH2Ph, F, F, H, 2-Py], [A1392; H, OCH2Ph, Cl, F, H, 2-Py], [A1393; H, OCH2Ph, Br, F, H, 2-Py], [A1394; H, OCH2Ph, I, F, H, 2-Py], [A1395; H, OCH2Ph, Me, F, H, 2-Py], [A1396; H, OCH2Ph, OMe, F, H, 2-Py], [A1397; H, OCH2Ph, CF3, F, H, 2-Py], [A1398; H, OCH2Ph, CHF2, F, H, 2-Py], [A1399; H, OCH2Ph, NO2, F, H, 2-Py], [A1400; H, OCH2Ph, H, F, H, 3-Py], [A1401; H, OCH2Ph, F, F, H, 3-Py], [A1402; H, OCH2Ph, Cl, F, H, 3-Py], [A1403; H, OCH2Ph, Br, F, H, 3-Py], [A1404; H, OCH2Ph, I, F, H, 3-Py], [A1405; H, OCH2Ph, Me, F, H, 3-Py], [A1406; H, OCH2Ph, OMe, F, H, 3-Py], [A1407; H, OCH2Ph, CF3, F, H, 3-Py], [A1408; H, OCH2Ph, CHF2, F, H, 3-Py], [A1409; H, OCH2Ph, NO2, F, H, 3-Py], [A1410; H, OCH2Ph, H, F, H, 4-Py], [A1411; H, OCH2Ph, F, F, H, 4-Py], [A1412;[H, OCH2Ph, Cl, F, H, 4-Py], [A1413; H, OCH2Ph, Br, F, H, 4-Py], [A1414; H, OCH2Ph, I, F, H, 4-Py], [A1415; H, OCH2Ph, Me, F, H, 4-Py], [A1416; H, OCH2Ph, OMe, F, H, 4-Py], [A1417; H, OCH2Ph, CF3, F, H, 4-Py], [A1418; H, OCH2Ph, CHF2, F, H, 4-Py], [A1419; H, OCH2Ph, NO2, F, H, 4-Py], ; [A1420;F,H,H,H,H,Et],[A1421;F,H,F,H,H,Et],[A1422;F,H,Cl,H,H,Et],[A1423;F,H,Br,H,H,Et],[A1424;F,H,I,H,H,Et],[A1425;F,H,Me,H,H,Et],[A1426;F,H,OMe,H,H,Et],[A1427;F,H,CF3,H,H,Et],[A1428;F,H,CHF2,H,H,Et],[A1429;F,H,NO2,H,H,Et],[A1430;F,H,H,H,H,Pr],[A1431;F,H,F,H,H,Pr],[A1432;F,H,Cl,H,H,Pr],[A1433;F,H,Br,H,H,Pr],[A1434;F,H,I,H,H,Pr],[A1435;F,H,Me,H,H,Pr],[A1436;F,H,OMe,H,H,Pr],[A1437;F,H,CF3,H,H,Pr],[A1438;F,H,CHF2,H,H,Pr],[A1439;F,H,NO2,H,H,Pr],[A1440;F,H,H,H,H,i-Pr],[A1441;F,H,F,H,H,i-Pr],[A1442;F,H,Cl,H,H,i-Pr],[A1443;F,H,Br,H,H,i-Pr],[A1444;F,H,I,H,H,i-Pr],[A1445;F,H,Me,H,H,i-Pr],[A1446;F,H,OMe,H,H,i-Pr],[A1447;F,H,CF3,H,H,i-Pr],[A1448;F,H,CHF2,H,H,i-Pr],[A1449;F,H,NO2,H,H,i-Pr],[A1450;F,H,H,H,H,c-Pr],[A1451;F,H,F,H,H,c-Pr],[A1452;F,H,Cl,H,H,c-Pr],[A1453;F,H,Br,H,H,c-Pr],[A1454;F,H,I,H,H,c-Pr],[A1455;F,H,Me,H,H,c-Pr],[A1456;F,H,OMe,H,H,c-Pr],[A1457;F,H,CF3,H,H,c-Pr],[A1458;F,H,CHF2,H,H,c-Pr],[A1459;F,H,NO2,H,H,c-Pr],[A1460;F,H,H,H,H,Bu],[A1461;F,H,F,H,H,Bu],[A1462;F,H,Cl,H,H,Bu],[A1463;[F, H, Br, H, H, Bu], [A1464; F, H, I, H, H, Bu], [A1465; F, H, Me, H, H, Bu], [A1466; F, H, OMe, H, H, Bu], [A1467; F, H, CF3, H, H, Bu], [A1468; F, H, CHF2, H, H, Bu], [A1469; F, H, NO2, H, H, Bu], [A1470; F, H, H, H, H, i-Bu], [A1471; F, H, F, H, H, i-Bu], [A1472; F, H, Cl, H, H, i-Bu], [A1473; F, H, Br, H, H, i-Bu], [A1474; F, H, I, H, H, i-Bu], [A1475; F, H, Me, H, H, i-Bu], [A1476; F, H, OMe, H, H, i-Bu], [A1477; F, H, CF3, H, H, i-Bu], [A1478; F, H, CHF2, H, H, i-Bu], [A1479; F, H, NO2, H, H, i-Bu], [A1480; F, H, H, H, H, CH2CF3], [A1481; F, H, F, H, H, CH2CF3], [A1482; F, H, Cl, H, H, CH2CF3], [A1483; F, H, Br, H, H, CH2CF3], [A1484; F, H, I, H, H, CH2CF3], [A1485; F, H, Me, H, H, CH2CF3], [A1486; F, H, OMe, H, H, CH2CF3], [A1487; F, H, CF3, H, H, CH2CF3], [A1488; F, H, CHF2, H, H, CH2CF3], [A1489; F, H, NO2, H, H, CH2CF3], [A1490; F, H, H, H, H, CF2CH3], [A1491; F, H, F, H, H, CF2CH3], [A1492; F, H, Cl, H, H, CF2CH3], [A1493; F, H, Br, H, H, CF2CH3], [A1494; F, H, I, H, H, CF2CH3], [A1495; F, H, Me, H, H, CF2CH3], [A1496; F, H, OMe, H, H, CF2CH3], [A1497; F, H, CF3, H, H, CF2CH3], [A1498; F, H, CHF2, H, H, CF2CH3], [A1499; F, H, NO2, H, H, CF2CH3], [A1500; F, H, H, H, H, 2-Py], [A1501; F, H, F, H, H, 2-Py], [A1502; F, H, Cl, H, H, 2-Py], [A1503;F, H, Br, H, H, 2-Py], [A1504; F, H, I, H, H, 2-Py], [A1505; F, H, Me, H, H, 2-Py], [A1506; F, H, OMe, H, H, 2-Py], [A1507; F, H, CF3, H, H, 2-Py], [A1508; F, H, CHF2, H, H, 2-Py], [A1509; F, H, NO2, H, H, 2-Py], [A1510; F, H, H, H, H, 3-Py], [A1511; F, H, F, H, H, 3-Py], [A1512; F, H, Cl, H, H, 3-Py], [A1513; F, H, Br, H, H, 3-Py], [A1514; F, H, I, H, H, 3-Py], [A1515; F, H, Me, H, H, 3-Py], [A1516; F, H, OMe, H, H, 3-Py], [A1517; F, H, CF3, H, H, 3-Py], [A1518; F, H, CHF2, H, H, 3-Py], [A1519; F, H, NO2, H, H, 3-Py], [A1520; F, H, H, H, H, 4-Py], [A1521; F, H, F, H, H, 4-Py], [A1522; F, H, Cl, H, H, 4-Py], [A1523; F, H, Br, H, H, 4-Py], [A1524; F, H, I, H, H, 4-Py], [A1525; F, H, Me, H, H, 4-Py], [A1526; F, H, OMe, H, H, 4-Py], [A1527; F, H, CF3, H, H, 4-Py], [A1528; F, H, CHF2, H, H, 4-Py], [A1529; F, H, NO2, H, H, 4-Py], ;

[0159] [A1530;H,H,H,H,H,Et],[A1531;H,H,H,H,H,Pr],[A1532;H,H,H,H,H,i-Pr],[A1533;H,H,H,H,H,c-Pr],[A1534;H,H,H,H,H,Bu],[A1535;H,H,H,H,H,i-Bu],[A1536;H,H,H,H,H,2-Py],[A1537;H,H,H,H,H,3-Py],[A1538;H,H,H,H,H,4-Py],[A1539;H,H,H,H,H,CH2CF3],[A1540;H,H,H,H,H,CF2CH3],[A1541;H,H,H,H,H,Me],[A1542;H,H,F,H,H,Me],[A1543;H,H,Cl,H,H,Me],[A1544;H,H,Br,H,H,Me],[A1545;H,H,I,H,H,Me],[A1546;H,H,Me,H,H,Me],[A1547;H,H,OMe,H,H,Me],[A1548;H,H,CF3,H,H,Me],[A1549;H,H,CHF2,H,H,Me],[A1550;H,H,NO2,H,H,Me],[A1551;H,H,H,H,H,Ph],[A1552;H,H,F,H,H,Ph],[A1553;H,H,Cl,H,H,Ph],[A1554;H,H,Br,H,H,Ph],[A1555;H,H,I,H,H,Ph],[A1556;H,H,Me,H,H,Ph],[A1557;H,H,OMe,H,H,Ph],[A1558;H,H,CF3,H,H,Ph],[A1559;H,H,CHF2,H,H,Ph],[A1560;H,H,NO2,H,H,Ph],[A1561;H,F,H,H,H,Me],[A1562;H,F,F,H,H,Me],[A1563;H,F,Cl,H,H,Me],[A1564;H,F,Br,H,H,Me],[A1565;H,F,I,H,H,Me],[A1566;H,F,Me,H,H,Me],[A1567;H,F,OMe,H,H,Me],[A1568;H,F,CF3,H,H,Me],[A1569;H,F,CHF2,H,H,Me],[A1570;H,F,NO2,H,H,Me],[A1571;H,F,H,H,H,Ph],[A1572;H,F,F,H,H,Ph],[A1573;H,F,Cl,H,H,Ph],[A1574;H,F,Br,H,H,Ph],[A1575;H,F,I,H,H,Ph],[A1576;H,F,Me,H,H,Ph],[A1577;H,F,OMe,H,H,Ph],[A1578;H,F,CF3,H,H,Ph],[A1579;H,F,CHF2,H,H,Ph],[A1580;H,F,NO2,H,H,Ph],[A1581;H,Cl,H,H,H,Me],[A1582;H,Cl,F,H,H,Me],[A1583;H,Cl,Cl,H,H,Me],[A1584;H,Cl,Br,H,H,Me],[A1585;H,Cl,I,H,H,Me],[A1586;H,Cl,Me,H,H,Me],[A1587;H,Cl,OMe,H,H,Me],[A1588;H,Cl,CF3,H,H,Me],[A1589;H,Cl,CHF2,H,H,Me],[A1590;H,Cl,NO2,H,H,Me],[A1591;H,Cl,H,H,H,Ph],[A1592;H,Cl,F,H,H,Ph],[A1593;H,Cl,Cl,H,H,Ph],[A1594;H,Cl,Br,H,H,Ph],[A1595;H,Cl,I,H,H,Ph],[A1596;H,Cl,Me,H,H,Ph],[A1597;H,Cl,OMe,H,H,Ph],[A1598;H,Cl,CF3,H,H,Ph],[A1599;H,Cl,CHF2,H,H,Ph],[A1600;H,Cl,NO2,H,H,Ph],[A1601;H,Br,H,H,H,Me],[A1602;H,Br,F,H,H,Me],[A1603;H,Br,Cl,H,H,Me],[A1604;H,Br,Br,H,H,Me],[A1605;H,Br,I,H,H,Me],[A1606;H,Br,Me,H,H,Me],[A1607;H,Br,OMe,H,H,Me],[A1608;H,Br,CF3,H,H,Me],[A1609;H,Br,CHF2,H,H,Me],[A1610;H,Br,NO2,H,H,Me],[A1611;H,Br,H,H,H,Ph],[A1612;H,Br,F,H,H,Ph],[A1613;H,Br,Cl,H,H,Ph],[A1614;H,Br,Br,H,H,Ph],[A1615;H,Br,I,H,H,Ph],[A1616;H,Br,Me,H,H,Ph],[A1617;H, Br, OMe, H, H, Ph], [A1618; H, Br, CF3, H, H, Ph], [A1619; H, Br, CHF2, H, H, Ph], [A1620; H, Br, NO2, H, H, Ph], ; [A1621;H,CF3,H,H,H,Me],[A1622;H,CF3,F,H,H,Me],[A1623;H,CF3,Cl,H,H,Me],[A1624;H,CF3,Br,H,H,Me],[A1625;H,CF3,I,H,H,Me],[A1626;H,CF3,Me,H,H,Me],[A1627;H,CF3,OMe,H,H,Me],[A1628;H,CF3,CF3,H,H,Me],[A1629;H,CF3,CHF2,H,H,Me],[A1630;H,CF3,NO2,H,H,Me],[A1631;H,CF3,H,H,H,Ph],[A1632;H,CF3,F,H,H,Ph],[A1633;H,CF3,Cl,H,H,Ph],[A1634;H,CF3,Br,H,H,Ph],[A1635;H,CF3,I,H,H,Ph],[A1636;H,CF3,Me,H,H,Ph],[A1637;H,CF3,OMe,H,H,Ph],[A1638;H,CF3,CF3,H,H,Ph],[A1639;H,CF3,CHF2,H,H,Ph],[A1640;H,CF3,NO2,H,H,Ph],[A1641;H,NO2,H,H,H,Me],[A1642;H,NO2,F,H,H,Me],[A1643;H,NO2,Cl,H,H,Me],[A1644;H,NO2,Br,H,H,Me],[A1645;H,NO2,I,H,H,Me],[A1646;H,NO2,Me,H,H,Me],[A1647;H,NO2,OMe,H,H,Me],[A1648;H,NO2,CF3,H,H,Me],[A1649;H,NO2,CHF2,H,H,Me],[A1650;H,NO2,NO2,H,H,Me],[A1651;H,NO2,H,H,H,Ph],[A1652;H,NO2,F,H,H,Ph],[A1653;H,NO2,Cl,H,H,Ph],[A1654;H,NO2,Br,H,H,Ph],[A1655;H,NO2,I,H,H,Ph],[A1656;H,NO2,Me,H,H,Ph],[A1657;H,NO2,OMe,H,H,Ph],[A1658;H,NO2,CF3,H,H,Ph],[A1659;H,NO2,CHF2,H,H,Ph],[A1660;H,NO2,NO2,H,H,Ph],[A1661;H,OCH2Ph,H,H,H,Me],[A1662;[H, OCH2Ph, F, H, H, Me], [A1663]; [H, OCH2Ph, Cl, H, H, Me], [A1664]; [H, OCH2Ph, Br, H, H, Me], [A1665]; [H, OCH2Ph, I, H, H, Me], [A1666]; [H, OCH2Ph, Me, H, H, Me], [A1667]; [H, OCH2Ph, OMe, H, H, Me], [A1668]; [H, OCH2Ph, CF3, H, H, Me], [A1669]; [H, OCH2Ph, CHF2, H, H, Me], [A1670]; [H, OCH2Ph, NO2, H, H, Me], [A1671]; [H, OCH2Ph, H, H, H, Ph], [A1672]; [H, OCH2Ph, F, H, H, Ph], [A1673]; [H, OCH2Ph, Cl, H, H, Ph], [A1674]; [H, OCH2Ph, Br, H, H, Ph], [A1675]; [H, OCH2Ph, I, H, H, Ph], [A1676]; [H, OCH2Ph, Me, H, H, Ph], [A1677]; [H, OCH2Ph, OMe, H, H, Ph], [A1678]; [H, OCH2Ph, CF3, H, H, Ph], [A1679]; [H, OCH2Ph, CHF2, H, H, Ph], [A1680]; [H, OCH2Ph, NO2, H, H, Ph], [A1681]; [H, F, H, F, H, Me], [A1682]; [H, F, F, F, H, Me], [A1683]; [H, F, Cl, F, H, Me], [A1684]; [H, F, Br, F, H, Me], [A1685]; [H, F, I, F, H, Me], [A1686]; [H, F, Me, F, H, Me], [A1687]; [H, F, OMe, F, H, Me], [A1688]; [H, F, CF3, F, H, Me], [A1689]; [H, F, CHF2, F, H, Me], [A1690]; [H, F, NO2, F, H, Me], [A1691]; [H, F, H, F, H, Ph], [A1692]; [H, F, Cl, F, H, Ph], [A1693]; [H, F, Br, F, H, Ph], [A1694]; [H, F, I, F, H, Ph], [A1695]; [H, F, Me, F, H, Ph], [A1696]; [H, F, OMe, F, H, Ph], [A1697]; [H, F, CF3, F, H, Ph], [A1698]; [H, F, CHF2, F, H, Ph], [A1699]; [H, F, NO2, F, H, Ph], [A1700]; [H, Cl, H, F, H, Me], [A1701]; [H, Cl, F, F, H, Me], [A1702];H, Cl, F, F, H, Me], [A1703; H, Cl, Cl, F, H, Me], [A1704; H, Cl, Br, F, H, Me], [A1705; H, Cl, I, F, H, Me], [A1706; H, Cl, Me, F, H, Me], [A1707; H, Cl, OMe, F, H, Me], [A1708; H, Cl, CF3, F, H, Me], [A1709; H, Cl, CHF2, F, H, Me], [A1710; H, Cl, NO2, F, H, Me], [A1711; H, Cl, H, F, H, Ph], [A1712; H, Cl, F, F, H, Ph], [A1713; H, Cl, Cl, F, H, Ph], [A1714; H, Cl, Br, F, H, Ph], [A1715; H, Cl, I, F, H, Ph], [A1716; H, Cl, Me, F, H, Ph], [A1717; H, Cl, OMe, F, H, Ph], [A1718; H, Cl, CF3, F, H, Ph], [A1719; H, Cl, CHF2, F, H, Ph], [A1720; H, Cl, NO2, F, H, Ph],; [A1721;H,Br,H,F,H,Me],[A1722;H,Br,F,F,H,Me],[A1723;H,Br,Cl,F,H,Me],[A1724;H,Br,Br,F,H,Me],[A1725;H,Br,I,F,H,Me],[A1726;H,Br,Me,F,H,Me],[A1727;H,Br,OMe,F,H,Me],[A1728;H,Br,CF3,F,H,Me],[A1729;H,Br,CHF2,F,H,Me],[A1730;H,Br,NO2,F,H,Me],[A1731;H,Br,H,F,H,Ph],[A1732;H,Br,F,F,H,Ph],[A1733;H,Br,Cl,F,H,Ph],[A1734;H,Br,Br,F,H,Ph],[A1735;H,Br,I,F,H,Ph],[A1736;H,Br,Me,F,H,Ph],[A1737;H,Br,OMe,F,H,Ph],[A1738;H,Br,CF3,F,H,Ph],[A1739;H,Br,CHF2,F,H,Ph],[A1740;H,Br,NO2,F,H,Ph],[A1741;H,CF3,H,F,H,Me],[A1742;H,CF3,F,F,H,Me],[A1743;H,CF3,Cl,F,H,Me],[A1744;H,CF3,Br,F,H,Me],[A1745;H,CF3,I,F,H,Me],[A1746;H,CF3,Me,F,H,Me],[A1747;H,CF3,OMe,F,H,Me],[A1748;H,CF3,CF3,F,H,Me],[A1749;H,CF3,CHF2,F,H,Me],[A1750;H,CF3,NO2,F,H,Me],[A1751;H,CF3,H,F,H,Ph],[A1752;H,CF3,F,F,H,Ph],[A1753;H,CF3,Cl,F,H,Ph],[A1754;H,CF3,Br,F,H,Ph],[A1755;H,CF3,I,F,H,Ph],[A1756;H,CF3,Me,F,H,Ph],[A1757;H,CF3,OMe,F,H,Ph],[A1758;H,CF3,CF3,F,H,Ph],[A1759;H,CF3,CHF2,F,H,Ph],[A1760;H,CF3,NO2,F,H,Ph],[A1761;H,NO2,H,F,H,Me],[A1762;H,NO2,F,F,H,Me],[A1763;H, NO2, Cl, F, H, Me], [A1764; H, NO2, Br, F, H, Me], [A1765; H, NO2, I, F, H, Me], [A1766; H, NO2, Me, F, H, Me], [A1767; H, NO2, OMe, F, H, Me], [A1768; H, NO2, CF3, F, H, Me], [A1769; H, NO2, CHF2, F, H, Me], [A1770; H, NO2, NO2, F, H, Me], [A1771; H, NO2, H, F, H, Ph], [A1772; H, NO2, F, F, H, Ph], [A1773; H, NO2, Cl, F, H, Ph], [A1774; H, NO2, Br, F, H, Ph], [A1775; H, NO2, I, F, H, Ph], [A1776; H, NO2, Me, F, H, Ph], [A1777; H, NO2, OMe, F, H, Ph], [A1778; H, NO2, CF3, F, H, Ph], [A1779; H, NO2, CHF2, F, H, Ph], [A1780; H, NO2, NO2, F, H, Ph], [A1781; H, OCH2Ph, H, F, H, Me], [A1782; H, OCH2Ph, F, F, H, Me], [A1783; H, OCH2Ph, Cl, F, H, Me], [A1784; H, OCH2Ph, Br, F, H, Me], [A1785; H, OCH2Ph, I, F, H, Me], [A1786; H, OCH2Ph, Me, F, H, Me], [A1787; H, OCH2Ph, OMe, F, H, Me], [A1788; H, OCH2Ph, CF3, F, H, Me], [A1789; H, OCH2Ph, CHF2, F, H, Me], [A1790; H, OCH2Ph, NO2, F, H, Me], [A1791; H, OCH2Ph, H, F, H, Ph], [A1792; H, OCH2Ph, F, F, H, Ph], [A1793; H, OCH2Ph, Cl, F, H, Ph], [A1794; H, OCH2Ph, Br, F, H, Ph], [A1795; H, OCH2Ph, I, F, H, Ph], [A1796; H, OCH2Ph, Me, F, H, Ph], [A1797; H, OCH2Ph, OMe, F, H, Ph], [A1798; H, OCH2Ph, CF3, F, H, Ph], [A1799; H, OCH2Ph, CHF2, F, H, Ph], [A1800; H, OCH2Ph, NO2, F, H, Ph], [A1801;F,H,H,H,H,Me],[A1802;F,H,F,H,H,Me],[A1803;F,H,Cl,H,H,Me],[A1804;F,H,Br,H,H,Me],[A1805;F,H,I,H,H,Me],[A1806;F,H,Me,H,H,Me],[A1807;F,H,OMe,H,H,Me],[A1808;F,H,CF3,H,H,Me],[A1809;F,H,CHF2,H,H,Me],[A1810;F,H,NO2,H,H,Me],[A1811;F,H,H,H,H,Ph],[A1812;F,H,F,H,H,Ph],[A1813;F,H,Cl,H,H,Ph],[A1814;F,H,Br,H,H,Ph],[A1815;F,H,I,H,H,Ph],[A1816;F,H,Me,H,H,Ph],[A1817;F,H,OMe,H,H,Ph],[A1818;F,H,CF3,H,H,Ph],[A1819;F,H,CHF2,H,H,Ph],[A1820;F,H,NO2,H,H,Ph],;

[0160] [A1821;H,NHC(O)OMe,H,H,H,Et],[A1822;H,NHC(O)OMe,F,H,H,Et],[A1823;H,NHC(O)OMe,Cl,H,H,Et],[A1824;H,NHC(O)OMe,Br,H,H,Et],[A1825;H,NHC(O)OMe,I,H,H,Et],[A1826;H,NHC(O)OMe,Me,H,H,Et],[A1827;H,NHC(O)OMe,OMe,H,H,Et],[A1828;H,NHC(O)OMe,CF3,H,H,Et],[A1829;H,NHC(O)OMe,CHF2,H,H,Et],[A1830;H,NHC(O)OMe,NO2,H,H,Et],[A1831;H,NHC(O)OMe,H,H,H,Pr],[A1832;H,NHC(O)OMe,F,H,H,Pr],[A1833;H,NHC(O)OMe,Cl,H,H,Pr],[A1834;H,NHC(O)OMe,Br,H,H,Pr],[A1835;H,NHC(O)OMe,I,H,H,Pr],[A1836;H,NHC(O)OMe,Me,H,H,Pr],[A1837;H,NHC(O)OMe,OMe,H,H,Pr],[A1838;H,NHC(O)OMe,CF3,H,H,Pr],[A1839;H,NHC(O)OMe,CHF2,H,H,Pr],[A1840;H,NHC(O)OMe,NO2,H,H,Pr],[A1841;H,NHC(O)OMe,H,H,H,i-Pr],[A1842;H,NHC(O)OMe,F,H,H,i-Pr],[A1843;H,NHC(O)OMe,Cl,H,H,i-Pr],[A1844;H,NHC(O)OMe,Br,H,H,i-Pr],[A1845;H,NHC(O)OMe,I,H,H,i-Pr],[A1846;H,NHC(O)OMe,Me,H,H,i-Pr],[A1847;H,NHC(O)OMe,OMe,H,H,i-Pr],[A1848;H,NHC(O)OMe,CF3,H,H,i-Pr],[A1849;H,NHC(O)OMe,CHF2,H,H,i-Pr],[A1850;H,NHC(O)OMe,NO2,H,H,i-Pr],[A1851;H,NHC(O)OMe,H,H,H,c-Pr],[A1852;H,NHC(O)OMe,F,H,H,c-Pr],[A1853;[H, NHC(O)OMe, Cl, H, H, c-Pr], [A1854]; [H, NHC(O)OMe, Br, H, H, c-Pr], [A1855]; [H, NHC(O)OMe, I, H, H, c-Pr], [A1856]; [H, NHC(O)OMe, Me, H, H, c-Pr], [A1857]; [H, NHC(O)OMe, OMe, H, H, c-Pr], [A1858]; [H, NHC(O)OMe, CF3, H, H, c-Pr], [A1859]; [H, NHC(O)OMe, CHF2, H, H, c-Pr], [A1860]; [H, NHC(O)OMe, NO2, H, H, c-Pr], [A1861]; [H, NHC(O)OMe, H, H, H, Bu], [A1862]; [H, NHC(O)OMe, F, H, H, Bu], [A1863]; [H, NHC(O)OMe, Cl, H, H, Bu], [A1864]; [H, NHC(O)OMe, Br, H, H, Bu], [A1865]; [H, NHC(O)OMe, I, H, H, Bu], [A1866]; [H, NHC(O)OMe, Me, H, H, Bu], [A1867]; [H, NHC(O)OMe, OMe, H, H, Bu], [A1868]; [H, NHC(O)OMe, CF3, H, H, Bu], [A1869]; [H, NHC(O)OMe, CHF2, H, H, Bu], [A1870]; [H, NHC(O)OMe, NO2, H, H, Bu], [A1871]; [H, NHC(O)OMe, H, H, H, i-Bu], [A1872]; [H, NHC(O)OMe, F, H, H, i-Bu], [A1873]; [H, NHC(O)OMe, Cl, H, H, i-Bu], [A1874]; [H, NHC(O)OMe, Br, H, H, i-Bu], [A1875]; [H, NHC(O)OMe, I, H, H, i-Bu], [A1876]; [H, NHC(O)OMe, Me, H, H, i-Bu], [A1877]; [H, NHC(O)OMe, OMe, H, H, i-Bu], [A1878]; [H, NHC(O)OMe, CF3, H, H, i-Bu], [A1879]; [H, NHC(O)OMe, CHF2, H, H, i-Bu], [A1880]; [H, NHC(O)OMe, H, H, H, CH2CF3], [A1881]; [H, NHC(O)OMe, F, H, H, CH2CF3], [A1882]; [H, NHC(O)OMe, Cl, H, H, CH2CF3], [A1883]; [A1884;[H, NHC(O)OMe, Br, H, H, CH2CF3], [A1885; H, NHC(O)OMe, I, H, H, CH2CF3], [A1886; H, NHC(O)OMe, Me, H, H, CH2CF3], [A1887; H, NHC(O)OMe, OMe, H, H, CH2CF3], [A1888; H, NHC(O)OMe, CF3, H, H, CH2CF3], [A1889; H, NHC(O)OMe, CHF2, H, H, CH2CF3], [A1890; H, NHC(O)OMe, NO2, H, H, CH2CF3], [A1891; H, NHC(O)OMe, H, H, H, CF2CH3], [A1892; H, NHC(O)OMe, F, H, H, CF2CH3], [A1893; H, NHC(O)OMe, Cl, H, H, CF2CH3], [A1894; H, NHC(O)OMe, Br, H, H, CF2CH3], [A1895; H, NHC(O)OMe, I, H, H, CF2CH3], [A1896; H, NHC(O)OMe, Me, H, H, CF2CH3], [A1897; H, NHC(O)OMe, OMe, H, H, CF2CH3], [A1898; H, NHC(O)OMe, CF3, H, H, CF2CH3], [A1899; H, NHC(O)OMe, CHF2, H, H, CF2CH3], [A1900; H, NHC(O)OMe, NO2, H, H, CF2CH3], [A1901; H, NHC(O)OMe, H, H, H, 2-Py], [A1902; H, NHC(O)OMe, F, H, H, 2-Py], [A1903; H, NHC(O)OMe, Cl, H, H, 2-Py], [A1904; H, NHC(O)OMe, Br, H, H, 2-Py], [A1905; H, NHC(O)OMe, I, H, H, 2-Py], [A1906; H, NHC(O)OMe, Me, H, H, 2-Py], [A1907; H, NHC(O)OMe, OMe, H, H, 2-Py], [A1908; H, NHC(O)OMe, CF3, H, H, 2-Py], [A1909; H, NHC(O)OMe, CHF2, H, H, 2-Py], [A1910; H, NHC(O)OMe, NO2, H, H, 2-Py], [A1911; H, NHC(O)OMe, H, H, H, 3-Py], [A1912; H, NHC(O)OMe, F, H, H, 3-Py], [A1913; H, NHC(O)OMe, Cl, H, H, 3-Py], [A1914;H, NHC(O)OMe, Br, H, H, 3-Py], [A1915; H, NHC(O)OMe, I, H, H, 3-Py], [A1916; H, NHC(O)OMe, Me, H, H, 3-Py], [A1917; H, NHC(O)OMe, OMe, H, H, 3-Py], [A1918; H, NHC(O)OMe, CF3, H, H, 3-Py], [A1919; H, NHC(O)OMe, CHF2, H, H, 3-Py], [A1920; H, NHC(O)OMe, NO2, H, H, 3-Py], [A1921; H, NHC(O)OMe, H, H, H, 4-Py], [A1922; H, NHC(O)OMe, F, H, H, 4-Py], [A1923; H, NHC(O)OMe, Cl, H, H, 4-Py], [A1924; H, NHC(O)OMe, Br, H, H, 4-Py], [A1925; H, NHC(O)OMe, I, H, H, 4-Py], [A1926; H, NHC(O)OMe, Me, H, H, 4-Py], [A1927; H, NHC(O)OMe, OMe, H, H, 4-Py], [A1928; H, NHC(O)OMe, CF3, H, H, 4-Py], [A1929; H, NHC(O)OMe, CHF2, H, H, 4-Py], [A1930; H, NHC(O)OMe, NO2, H, H, 4-Py], [A1931; H, NHC(O)OMe, H, F, H, Et], [A1932; H, NHC(O)OMe, F, F, H, Et], [A1933; H, NHC(O)OMe, Cl, F, H, Et], [A1934; H, NHC(O)OMe, Br, F, H, Et], [A1935; H, NHC(O)OMe, I, F, H, Et], [A1936; H, NHC(O)OMe, Me, F, H, Et], [A1937; H, NHC(O)OMe, OMe, F, H, Et], [A1938; H, NHC(O)OMe, CF3, F, H, Et], [A1939; H, NHC(O)OMe, CHF2, F, H, Et], [A1940; H, NHC(O)OMe, NO2, F, H, Et], [A1941; H, NHC(O)OMe, H, F, H, Pr], [...

Claims

1. Formula (I): 【Chemical 1】 〔Wherein, Z represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 5-6 membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group A {the C3-C6 cycloalkyl group, the phenyl group, and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group E}, Q represents a group represented by Q1, a group represented by Q2, or a group represented by Q3 (# represents the bonding site to the phenyl group, and ● represents the bonding site to the sulfur atom), 【Chemical 2】 R 1 、R 2 、R 3 、R 4 and R 5 are the same or different and may be substituted with one or more substituents selected from Group D, C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, phenyl group, 5-6 membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group E}, hydrogen atom, halogen atom, nitro group, cyano group, -OR 10 , -C(O)R 12 , -CR 13 =N-O-R 14 , -C(O)NR 20 R 21 , -NR 22 C(O)R 23 , or -C(O)N(OR 24 )R25, R6, R 7 , R 8 and R 9 are the same or different and each represents a hydrogen atom or a fluorine atom, R 10 、R 12 、R 13 、R 14 、R 20、R 21 、R 22 、R 23 、R 24 、and R 25 are the same or different and may be a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a 5-6 membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, and the 5-6 membered aromatic heterocyclic group may be substituted with one or more halogen atoms} or a hydrogen atom, which may be substituted with one or more substituents selected from Group D. n represents 0, 1 or 2. Group A: A group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group {the C3-C6 cycloalkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, a halogen atom, and a cyano group. Group C: A group consisting of a C1-C3 chain hydrocarbon group and a halogen atom. Group D: A group consisting of a C1-C3 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, a phenyl group, a 5-6 membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C}, a halogen atom, and a cyano group. Group E: 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}, and a halogen atom.〕 A method for controlling plant diseases by treating a plant or the soil in which the plant is cultivated with a compound represented by the formula (I) or its N-oxide or salts thereof.

2. In Claim 1, the compound represented by the formula (I) or its N-oxide or salts thereof is such that Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 5-6 membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, and the 5-6 membered aromatic heterocyclic group may be substituted with one or more halogen atoms}, R 1 、R 2 、R 3 、R 4 and R 5 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group {the C3-C6 cycloalkyl group and the phenyl group may be substituted with one or more halogen atoms}, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10 , -C(O)NR 20 R 21 , or -NR 22 C(O)R23, R 10 is a C1-C3 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F, R 21 is a phenyl group which may be substituted with one or more halogen atoms, R 20 and R 22 are each a hydrogen atom, R23 is a phenyl group which may be substituted with one or more halogen atoms, a C1-C4 chain hydrocarbon group, or a C3-C6 cycloalkyl group, The method according to claim 1, wherein the group F is a compound which is a phenyl group which may be substituted with one or more substituents selected from group C and a halogen atom, or an N-oxide thereof or a salt thereof.

3. In claim 1, the compound represented by formula (I) or an N-oxide thereof or a salt thereof is, R 6 、 R 7 、 R 8 and R 9 The method according to claim 1 or claim 2, wherein R 6 7 8 9 are each a hydrogen atom, a compound thereof, an N-oxide thereof, or a salt thereof.

4. In claim 1, the compound represented by formula (I) or an N-oxide thereof or a salt thereof is, Q is a group represented by Q1 or a group represented by Q2, R 6 , R 7 and R 8 is a compound in which each of them is a hydrogen atom, or an N-oxide thereof, or a salt thereof, according to the method of claim 1 or claim 2.

5. In claim 1, the compound represented by formula (I) or an N-oxide thereof or a salt thereof is, Q is a group represented by Q1, R 6 and R 7 The method according to claim 1 or claim 2, which is a compound in which each of them is a hydrogen atom, or its N-oxide, or a salt thereof.

6. Formula (II): 【Chemical Formula 3】 [Wherein, Q A and the combination of m is Q A is Q A a group represented by 1 or Q A a group represented by 2, m represents a combination of 0, 1 or 2; or, Q A is Q A is a group represented by 3, m represents a combination of 1 or 2, Q A the group represented by 1, Q A the group represented by 2, and Q A The group represented by 3 each represents a group represented by the following formula (where # represents the bonding site with the phenyl group and ● represents the bonding site with the sulfur atom). [Chemical Formula 4] R 6A 、R 7A 、R 8A and R 9A are the same or different and each represents a hydrogen atom or a fluorine atom, Z A represents a C2-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5- to 6-membered aromatic heterocyclic group {the C2-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more halogen atoms}, R 3A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR10A, or -NR 22A C(O)R23A, R 2A and R 4A are the same or different and may be a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR10AA, -C(O)NR 20A R 21A , or -NR 22A C(O)R23B, R 1A and R 5A are the same or different and each represents a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, or -OR10A, However, R 1A , R 2A , R 3A , R 4A and R 5A at least one of which is not a hydrogen atom, R10A represents a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, R21A represents a phenyl group which may be substituted with one or more halogen atoms, R20A and R22A are the same or different and represent a C1-C3 chain hydrocarbon group or a hydrogen atom, R23A represents a phenyl group which may be substituted with one or more halogen atoms, a C1-C6 chain hydrocarbon group, or a C3-C6 cycloalkyl group, R10AA represents a C1-C3 chain hydrocarbon group which may be substituted with one phenyl group {the phenyl group may be substituted with one or more methyl groups}, R23B represents a C1-C4 chain hydrocarbon group or a cyclopropyl group.] A compound represented by or an N-oxide thereof or a salt thereof.

7. R6A and R7A are the same or different and are a hydrogen atom or a fluorine atom, R8A and R9A are each a hydrogen atom, ZA is a C2-C5 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may be substituted with one or more halogen atoms}, R 3A is a C1-C5 chain hydrocarbon group, a C3-C5 cycloalkyl group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10A , or -NR 22A C(O)R23A, and R 2A and R 4A are the same or different and are a C1-C3 chain hydrocarbon group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR10AA, -C(O)NR 20A R 21A or -NR 22A C(O)R23B, and R 1A and R 5A are the same or different and are each a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, or -OR10A, However, R 1A , R 2A , R 3A , R 4A and R 5A at least one of which is not a hydrogen atom, R20A and R22A are each a hydrogen atom, The compound according to claim 6, or its N-oxide or salts thereof, wherein R23A is a phenyl group which may be substituted with one or more halogen atoms, a C1-C4 chain hydrocarbon group, or a C3-C6 cycloalkyl group.

8. R 6A 、 R 7A 、 R 8A and R 9A are each a hydrogen atom, the compound according to claim 6 or claim 7, or an N-oxide thereof, or a salt thereof.

9. Q A is Q A the group represented by 1 or Q A the group represented by 2, and m is 0, 1 or 2 R 6A 、 R 7A and R 8A are each a hydrogen atom, the compound or its N-oxide or salts thereof according to claim 6 or claim 7.

10. Q A is Q A is a group represented by 1, and m is 0, 1 or 2, R 6A and R 7A are each a hydrogen atom, a compound or an N-oxide thereof or a salt thereof according to claim 6 or claim 7.

11. A plant disease control composition containing the compound according to any one of claims 6 to 10, or its N-oxide or salts thereof.

12. A method for controlling plant diseases by treating an effective amount of the compound according to any one of claims 6 to 10, or its N-oxide or salts thereof, on a plant or the soil in which the plant is cultivated.

13. Use of the compound according to any one of claims 6 to 10, or its N-oxide or salts thereof, for controlling plant diseases.

14. A composition containing 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 claims 6 to 10, or its N-oxide or salts thereof: Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient; Group (b): a fungicidal active ingredient; Group (c): a plant growth regulating ingredient; Group (d): a repellent ingredient.

15. Seeds or vegetative reproductive organs holding an effective amount of the compound represented by formula (I) according to any one of claims 1 to 5, or its N-oxide or salts thereof, the compound according to any one of claims 6 to 10, or its N-oxide or salts thereof, or the composition according to claim 14.

16. Formula (III): 【Chemical Formula 5】 〔In the formula, R 6B and R 7B are the same or different and each represents a hydrogen atom or a fluorine atom, Z B represents a C3-C6 chain hydrocarbon group or a C4-C6 cycloalkyl group {the C3-C6 chain hydrocarbon group and the C4-C6 cycloalkyl group may be substituted with one or more halogen atoms}. The compound represented by.

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