Method for controlling plant diseases
Patent Information
- Application Number
- JP2024509183
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Priority Date
- 2023-03-23
- Filing Date
- 2023-03-23
- Publication Date
- 2026-02-05
AI Technical Summary
Current methods for controlling plant diseases are inadequate in effectively managing and preventing the spread of diseases in plants, particularly soybean rust, which can lead to significant crop losses.
A compound represented by formula (I) or its N-oxide/salt, which is applied to plants or soil, exhibits excellent control effects against plant diseases, including soybean rust, by treating the plants or soil where soybeans are cultivated.
The compound effectively controls plant diseases, providing a method for managing and preventing the spread of diseases such as soybean rust, thereby protecting crop yields.
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Abstract
Description
Plant disease control method
[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application No. 2022-048030 (filed March 24, 2022), the entire contents of which are incorporated herein by reference.
[0002] The present invention relates to a method for controlling plant diseases.
[0003] Patent Document 1 describes biphenyl compounds as plant disease control agents.
[0004] WO 2008 / 053044
[0005] An object of the present invention is to provide an excellent method for controlling plant diseases.
[0006] The present inventors have conducted studies to find an excellent method for controlling plant diseases and have found that a compound represented by the following formula (I) has excellent control activity against plant diseases.
[0007] [1] Formula (I) [wherein R1 represents a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from group B, a 3-7 membered non-aromatic heterocyclic group optionally having one or more substituents selected from group B, a methyl group having one or more substituents selected from group C, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group optionally have one or more substituents selected from group E}, or NR29R30, n represents 0, 1 or 2, R2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, OR6, SR7, S(O)R8, S(O)2R9, NRR11, C(O)R12, a nitro group, a cyano group, or a halogen atom, p represents 0, 1, or 2, and when p is 2, two R2s may be the same or different, R3 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have one or more substituents selected from Group B), a phenyl group, a 5-6 membered aromatic heterocyclic group (the phenyl group and the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from Group D), OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom; q represents 1, 2, or 3; when q is 2 or 3, two or three R3s may be the same or different; R4 and R5 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, OR22, SR23, S(O)R24, S(O)2R25, NR26R27, C(O)R28, a nitro group, a cyano group, a halogen atom, or a hydrogen atom;R6, R7, R10, R22, R23, R26, and R29 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R8, R9, R24, R25, and R30 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; R11 and R27 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group (the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group are optionally substituted with one or more halogen atoms), or a hydrogen atom; R12, R19, and R28 are the same or different and represent a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, or a C2-C8 dialkylamino group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms); R13, R14, R15, R16, and R21 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group optionally have one or more substituents selected from Group A), a phenyl group, or a 5-6 membered aromatic heterocyclic group (the phenyl group and the 5-6 membered aromatic heterocyclic group optionally have one or more substituents selected from Group D),R17 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D}, a (C1-C6 alkyl)carbonyl group, or a (C1-C6 alkoxy)carbonyl group {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group are optionally substituted with one or more halogen atoms}, R18 and R20 are the same or different and represent a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, or a hydrogen atom, Adjacent pairs of R3 and R4 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally have one or more substituents selected from Group E); and two adjacent pairs of R3 and R3 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally have one or more substituents selected from Group E).Group A: the group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group D}, a halogen atom, a cyano group, a nitro group, and a hydroxy group. Group B: a group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms), a hydroxy group, a halogen atom, and a cyano group. Group C: the group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group B}, a phenyl group, and a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group D}.Group D: a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a (C1-C6 alkyl)carbonylamino group, a (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkyl the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group, and the (C1-C6 alkoxy)carbonylamino group are optionally substituted with one or more halogen atoms}, the group consisting of a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, an amino group, a nitro group, a cyano group, a hydroxy group, and a halogen atom. Group E: a group consisting of a C1-C6 open chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, {the C1-C6 open chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a hydroxy group, a halogen atom, and a cyano group.] (hereinafter referred to as the present compound X) or an N-oxide thereof, or a salt thereof (hereinafter the compound represented by formula (I) or the N-oxide thereof, or a salt thereof will be referred to as the present compound Y).[2] The method according to [1], wherein the compound represented by formula (I) or an N-oxide thereof, or a salt thereof is a compound in which R1 is a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from group B, or a methyl group having one or more substituents selected from group C (hereinafter referred to as the present compound N), or an N-oxide thereof, or a salt thereof (hereinafter referred to as the present compound). [3] In [1] or [2], the compound represented by formula (I) or its N-oxide, or a salt thereof, is a C2-C6 chain hydrocarbon group, R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms or a halogen atom, R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an aliphatic acid, a hydroxyl group ...
[0022] The method according to [1] or [2], wherein R4 and R5 are an amino group, a hydroxy group, or a halogen atom, and two adjacent R3 and R3 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), and R4 and R5 are the same or different and are a halogen atom or a hydrogen atom, or an N-oxide thereof, or a salt thereof. [4] Use of the compound according to any one of [1] to [3], an N-oxide thereof, or a salt thereof for controlling plant diseases. [5] A method for controlling soybean rust fungus by applying the compound according to any one of [1] to [3], an N-oxide thereof, or a salt thereof to soybeans or the soil in which soybeans are grown. [6] A compound represented by formula (II) [wherein R1a represents a C2-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group optionally substituted with one or more halogen atoms, a phenyl group, or a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group are optionally substituted with one or more halogen atoms}, R3a represents a C1-C3 alkyl group, a C1-C3 alkoxy group, a cyclopropyl group {the cyclopropyl group is optionally substituted with one or more halogen atoms}, or a halogen atom, qa represents 1, 2, or 3, when qa is 2 or 3, two or three R3a's may be the same or different, and R4a and R5a represent hydrogen atoms.] (hereinafter referred to as compound D of the present invention), or an N-oxide or a salt thereof (hereinafter compound D of the present invention, the N-oxide, or a salt thereof will be referred to as the compound of the present invention). [7] An agricultural chemical composition containing the compound according to [6] or its N-oxide, or a salt thereof, and an inert carrier. [8] 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 [6] or its N-oxide, or a salt 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 regulator; Group (d): a repellent ingredient. [9] A method for controlling plant diseases, which comprises applying an effective amount of the compound according to [6] or its N-oxide, or a salt thereof, or an effective amount of the composition according to [8] to a plant or soil in which the plant is grown.
[10] Use of the compound according to [6] or its N-oxide, or a salt thereof, or the composition according to [8], for controlling plant diseases.
[11] A seed or a vegetative reproductive organ carrying an effective amount of the compound according to [6], its N-oxide, or a salt thereof, or an effective amount of the composition according to [8].
[0008] According to the present invention, plant diseases can be controlled.
[0009] The substituents of the present invention will be explained. A halogen atom refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, or when a substituent has two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different. In this specification, the expressions "optionally substituted with one or more substituents selected from Group X" or "optionally having one or more substituents selected from Group X" (X means any one of A, B, C, D, E, A1, B1, C1, E1, B2, C2, and E2) mean that when two or more substituents selected from Group X are present, these substituents may be the same or different. In this specification, the expression "CX-CY" means that the number of carbon atoms is X to Y. For example, the expression "C1-C6" means that the number of carbon atoms is 1 to 6. A chain hydrocarbon group refers to an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Examples of alkylsulfanyl groups include methylsulfanyl, ethylsulfanyl, isopropylsulfanyl, and hexylsulfanyl groups.Examples of alkylsulfinyl groups include methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, and hexylsulfinyl groups. Examples of alkylsulfonyl groups include methanesulfonyl, ethanesulfonyl, isopropanesulfonyl, and hexanesulfonyl groups. Examples of alkylcarbonyl groups include acetyl and propionyl groups. Examples of alkoxycarbonyl groups include methoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl groups. Examples of alicyclic hydrocarbon groups include cycloalkyl or cycloalkenyl groups. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of cycloalkenyl groups include cyclopentenyl and cyclohexenyl groups. Examples of aryl groups include phenyl and naphthyl groups. Examples of the aromatic heterocyclic group include 5-membered aromatic heterocyclic groups such as a pyrrolyl group, a furanyl 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; and 6-membered aromatic heterocyclic groups such as a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, and a tetrazinyl group. Examples of non-aromatic heterocyclic groups include aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, thiazolinyl, oxazolidinyl, thiazolidinyl, isoxazolinyl, isoxazolidinyl, isothiazolinyl, isothiazolidinyl, dioxolanyl, dioxanyl, piperidyl, piperazinyl, morpholinyl, thiomorpholinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, azepanyl, oxepanyl, and thiepanyl groups.
[0010] The compound Y or the compound of the present invention may exist in one or more stereoisomers. Stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.
[0011] The compound represented by the present compound X or the present compound D, or an N-oxide thereof, may form an acid addition salt such as a hydrochloride, a sulfate, a nitrate, a phosphate, an acetate, or a benzoate when mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid.
[0012] In the present compound Y, the compound in which adjacent R3 and R4, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may have one or more substituents selected from Group E) is specifically represented by formula (IA): wherein R1, R2, R5, n and p have the same meaning as in [1], R3B and R3C are the same or different and have the same meaning as R3 in [1] or represent a hydrogen atom, and R3A and R4, together with the carbon atom to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may have one or more substituents selected from Group E).
[0013] In the present compound Y, the compound in which two adjacent R3 and R3, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), a benzene ring, or a 5-6-membered aromatic heterocycle (the benzene ring and the 5-6-membered aromatic heterocycle may have one or more substituents selected from Group E) is specifically represented by the following: 1) in formula (IA), R1, R2, R4, R5, n, and p have the same meaning as in [1], R3C has the same meaning as R3 in [1] or represents a hydrogen atom, a compound in which R3A and R3B, together with the carbon atom to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), a benzene ring, or a 5-6-membered aromatic heterocycle (the benzene ring and the 5-6-membered aromatic heterocycle may have one or more substituents selected from Group E); or 2) in formula (IA), R1, R2, R4, R5, n, and p have the same meaning as in [1], R3A has the same meaning as R3 in [1] or represents a hydrogen atom, A compound in which R3B and R3C, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may have one or more substituents selected from Group E).
[0014] Embodiments of the present compound X include the following compounds. [Embodiment X1] A compound of the present compound X, in which R1 is a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from group A. [Embodiment X2] A compound of the present compound X, in which R1 is a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from group B. [Embodiment X3] A compound of the present compound X, in which R1 is a methyl group having one or more substituents selected from group C. [Embodiment X4] A compound of the present compound X, in which R1 is a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, or a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from group B. [Embodiment X5] A compound of the present compound X, in which R1 is a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, or a methyl group having one or more substituents selected from group C. [Aspect X6] A compound of the present compound X, wherein R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect X7] A compound of the present compound X, wherein R2 is a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B. [Aspect X8] A compound of the present compound X, wherein R2 is OR6, SR7, S(O)R8, S(O)2R9, NRR11, C(O)R12, a nitro group, or a cyano group. [Aspect X9] A compound of the present compound X, wherein R2 is a halogen atom. [Aspect X10] A compound of the present compound X, wherein R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect X11] A compound of the present compound X, wherein R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A. [Aspect X12] A compound of the present compound X, wherein R3 is a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B). [Aspect X13] A compound of the present compound X, wherein R3 is a phenyl group or a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may have one or more substituents selected from Group D).[Aspect X14] A compound of the present compound X, wherein R3 is OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, or a hydroxy group. [Aspect X15] A compound of the present compound X, wherein R3 is a halogen atom. [Aspect X16] A compound of the present compound X, wherein R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom. [Aspect X17] A compound of the present compound X, in which R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, or a halogen atom. [Aspect X18] A compound of the present compound X, in which adjacent R3 and R4, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B). [Aspect X19] A compound of the present compound X, in which adjacent R3 and R4, together with the carbon atoms to which they are bonded, form a benzene ring or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally having one or more substituents selected from Group E). [Aspect X20] A compound in which, in the compound X, two adjacent pairs of R3 and R3, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B). [Aspect X21] A compound in the compound X, where two adjacent pairs of R3 and R3, together with the carbon atoms to which they are bonded, form a benzene ring or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally have one or more substituents selected from Group E). [Aspect X22] A compound in the compound X, where R4 and R5 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom.[Aspect X23] A compound of this compound X in which R4 and R5 are the same or different and represent a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, a halogen atom, or a hydrogen atom. [Aspect X24] A compound of this compound X in which R4 and R5 are the same or different and represent OR22, SR23, S(O)R24, S(O)2R25, NR26R27, C(O)R28, a nitro group, a cyano group, a halogen atom, or a hydrogen atom. [Aspect X25] A compound of this compound X in which R4 and R5 are the same or different and represent a halogen atom or a hydrogen atom. [Aspect X26] A compound of this compound X in which R4 and R5 are a hydrogen atom. [Aspect X27] A compound of this compound X in which n is 0. [Aspect X28] A compound of this compound X in which n is 1. [Aspect X29] The compound X in which n is 2. [Aspect X30] The compound X in which p is 0. [Aspect X31] The compound X in which p is 1. [Aspect X32] The compound X in which p is 2. [Aspect X33] The compound X in which q is 1. [Aspect X34] The compound X in which q is 2. [Aspect X35] The compound X in which q is 3. [Aspect X36] In Compound X, R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom; R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom; two adjacent R3s and R3s, together with the carbon atoms to which they are bonded, may form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B}; and R4 and R5 are the same or different and are a halogen atom, or a hydrogen atom.[Aspect X37] In Compound X, p is 0; R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, or a halogen atom; two adjacent R3s and R3s, together with the carbon atoms to which they are bonded, may form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B); and R4 and R5 are the same or different and are hydrogen atoms. [Aspect X38] In Compound X, R1 is a C2-C6 open chain hydrocarbon group, R2 is a C1-C6 open chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, R3 is a C1-C6 open chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom, two adjacent R3s and R3s may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B), and R4 and R5 are the same or different and are a halogen atom, or a hydrogen atom. [Aspect X39] A method for controlling soybean rust fungi by treating soybeans or the soil in which soybeans are grown with the present compound X. [Aspect X40] A method for controlling soybean rust fungi by treating soybeans or the soil in which soybeans are grown with the compound represented by Aspect X38. [Aspect X41] A compound in which R1 is a 3-7 membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B. [Aspect X42] A compound in which R1 is a C6-C10 aryl group optionally having one or more substituents selected from Group E. [Aspect X43] A compound in which R1 is a 5-10 membered aromatic heterocyclic group optionally having one or more substituents selected from Group E. [Aspect X44] A compound in which R1 is NR29R30.[Aspect X45] In Compound X, R1 is a C2-C6 chain hydrocarbon group, a C6-C10 aryl group, or a 5- to 10-membered aromatic heterocyclic group (the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may have one or more substituents selected from Group E), R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms or a halogen atom, R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2 Compounds in which R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom, and two adjacent R3 and R3 may be joined together with the carbon atoms to which they are bonded to form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), and R4 and R5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect X46] In Compound X, R1 is a C6-C10 aryl group optionally having one or more substituents selected from Group E, R2 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a halogen atom, and R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR 21. Compounds in which R4 and R5 are the same or different and are a halogen atom, and two adjacent R3 and R3 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B), and R4 and R5 are the same or different and are a halogen atom, or a hydrogen atom.[Aspect X47] In Compound X, R1 is a 5-10 membered aromatic heterocyclic group optionally having one or more substituents selected from Group E, R2 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a halogen atom, R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NO A compound in which R21 is a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom, and two adjacent R3 and R3, together with the carbon atoms to which they are bonded, may form a C5-C6 alicyclic hydrocarbon or a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B), and R4 and R5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect X48] A method for controlling soybean rust fungi by treating soybeans or the soil in which soybeans are grown with the compound represented by Aspect X45. [Aspect X49] A method for controlling soybean rust fungi by treating soybeans or the soil in which soybeans are grown with any of Aspects X1 to X38, Aspects X41 to X47, or the present compound X, or an N-oxide thereof, or a salt thereof.
[0015] The present compound X also includes the following compounds: [Aspect Z1] Formula (IAA) [Wherein, R1 is a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A1, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a 3-7 membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B1, a methyl group, a phenyl group, a 5-6 membered aromatic heterocyclic group having one or more substituents selected from Group C1 {the phenyl group and the 5-6 membered aromatic heterocyclic group optionally have one or more substituents selected from Group E1}, or NR29R30, n is 0, 1 or 2, R2C is a fluorine atom or a hydrogen atom, R3A and R3C are the same or different and are a C1-C3 alkyl group optionally having one or more halogen atoms, a halogen atom, or a hydrogen atom, R3B is a C1-C3 alkyl group optionally having one or more halogen atoms or a halogen atom, and R29 and R30 are the same or different and are a C1-C6 alkyl group optionally having one or more halogen atoms. Group A1: A group consisting of a cyclopropyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group optionally have one or more substituents selected from Group E1), and a halogen atom. Group B1: A group consisting of a C1-C3 alkyl group, optionally having one or more halogen atoms, and a halogen atom. Group C1: A group consisting of a cyclopropyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group optionally have one or more substituents selected from Group E1), and a halogen atom. Group E1: A group consisting of a C1-C3 alkyl group, optionally having one or more halogen atoms, and a halogen atom. [Aspect Z2] A compound represented by the formula (I): in Aspect Z1, RA and RC are the same or different and are a methyl group, a halogen atom, or a hydrogen atom, optionally having one or more halogen atoms, and RB is a methyl group or a halogen atom, optionally having one or more halogen atoms.[Aspect Z3] A compound in Aspect Z1 wherein RA and RC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, optionally having one or more halogen atoms, and RB is a methyl group or a halogen atom, optionally having one or more halogen atoms. [Aspect Z4] A compound in Aspect Z1 wherein RA and RC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, optionally having one or more halogen atoms, and RB is a methyl group, a fluorine atom, or a chlorine atom, optionally having one or more halogen atoms. [Aspect Z5] A compound in Aspect Z1 wherein RA and RC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, optionally having one or more halogen atoms, and RB is a methyl group, a fluorine atom, or a chlorine atom, optionally having one or more halogen atoms. [Aspect Z6] A compound in Aspect Z1 wherein RA and RC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, optionally having one or more halogen atoms, and RB is a methyl group, a fluorine atom, or a chlorine atom, optionally having one or more halogen atoms. [Aspect Z7] A compound in Aspect Z1 wherein R3A is a methyl group, a fluorine atom, or a hydrogen atom, R3B is a methyl group, a fluorine atom, or a chlorine atom which may have one or more halogen atoms, and R3C is a fluorine atom or a hydrogen atom. [Aspect Z8] A compound in Aspect Z1 wherein R3A and R3C are the same or different and are a fluorine atom or a hydrogen atom, and R3B is a methyl group, a fluorine atom, or a chlorine atom which may have one or more halogen atoms. [Aspect Z9] A compound in Aspect Z1 wherein R3A and R3C are the same or different and are a fluorine atom or a hydrogen atom, and R3B is a methyl group, a fluorine atom, or a chlorine atom. [Aspect Z10] A compound in Aspect Z1 wherein R3A and R3C are the same or different and are a fluorine atom or a hydrogen atom, and R3B is a fluorine atom or a chlorine atom. [Aspect Z11] A compound in Aspect Z1 in which R3A and R3C are the same or different and are a fluorine atom or a hydrogen atom, and R3B is a chlorine atom. [Aspect Z12] A compound in Aspect Z1 in which R2C is a hydrogen atom. [Aspect Z13] A compound in Aspect Z2 in which R2C is a hydrogen atom. [Aspect Z14] A compound in Aspect Z3 in which R2C is a hydrogen atom.[Aspect Z15] A compound in Aspect Z4 in which R2C is a hydrogen atom. [Aspect Z16] A compound in Aspect Z5 in which R2C is a hydrogen atom. [Aspect Z17] A compound in Aspect Z6 in which R2C is a hydrogen atom. [Aspect Z18] A compound in Aspect Z7 in which R2C is a hydrogen atom. [Aspect Z19] A compound in Aspect Z8 in which R2C is a hydrogen atom. [Aspect Z20] A compound in Aspect Z9 in which R2C is a hydrogen atom. [Aspect Z21] A compound in Aspect Z10 in which R2C is a hydrogen atom. [Aspect Z22] A compound in Aspect Z11 in which R2C is a hydrogen atom. [Aspect Z23] The compound in any of Aspects Z1 to Z22, wherein R1 is a C2-C4 chain hydrocarbon group optionally having one or more substituents selected from Group A1, a C3-C4 cycloalkyl group optionally having one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B1, a methyl group having one or more substituents selected from Group C1, a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group E1), or NR29R30, and R29 and R30 are the same or different and are C1-C3 alkyl groups. [Aspect Z24] The compound in any of Aspects Z1 to Z22, wherein R1 is a C2-C4 alkyl group optionally having one or more fluorine atoms, a C3-C4 cycloalkyl group optionally having one or more fluorine atoms, a methyl group having one or more substituents selected from Group C1, a 5- or 6-membered aromatic heterocyclic group (the 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group E1), or NR29R30, and R29 and R30 are the same or different and are C1-C3 alkyl groups. [Aspect Z25] The compound in any of Aspects Z1 to Z22, wherein R1 is a C2-C4 alkyl group optionally having one or more fluorine atoms, a 5- or 6-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B2, a methyl group having one or more substituents selected from Group C2, a 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group E2), or NR29R30, and R29 and R30 are the same or different and are C1-C3 alkyl groups.Group B2: A group consisting of a methyl group optionally having one or more fluorine atoms and a halogen atom. Group C2: A group consisting of a cyclopropyl group, a phenyl group, a 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group E2), and a halogen atom, each optionally having one or more fluorine atoms. Group E2: A group consisting of a methyl group optionally having one or more fluorine atoms and a halogen atom. [Aspect Z26] A compound in any of Aspects Z1 to Z22, wherein R1 is a C2-C4 chain hydrocarbon group optionally having one or more substituents selected from Group A1. [Aspect Z27] A compound in any of Aspects Z1 to Z22, wherein R1 is a C3-C4 cycloalkyl group optionally having one or more halogen atoms. [Aspect Z28] A compound in any of Aspects Z1 to Z22, wherein R1 is a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B1. [Aspect Z29] A compound in any one of Aspects Z1 to Z22, wherein R1 is a methyl group having one or more substituents selected from Group C1. [Aspect Z30] A compound in any one of Aspects Z1 to Z22, wherein R1 is a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group E1). [Aspect Z31] A compound in any one of Aspects Z1 to Z22, wherein R1 is NR29R30, and R29 and R30 are the same or different and are C1-C3 alkyl groups. [Aspect Z32] A compound in any one of Aspects Z1 to Z22, wherein R1 is a C2-C4 alkyl group optionally having one or more fluorine atoms. [Aspect Z33] A compound in any one of Aspects Z1 to Z22, wherein R1 is a C3-C4 cycloalkyl group optionally having one or more fluorine atoms. [Aspect Z34] A compound in any one of Aspects Z1 to Z22, wherein R1 is a 5- or 6-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B2. [Aspect Z35] A compound in any one of Aspects Z1 to Z22, wherein R1 is a methyl group having one or more substituents selected from Group C2. [Aspect Z36] A compound in any one of Aspects Z1 to Z22, wherein R1 is a 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group E2).
[0016] The following compounds are examples of the present compound.
[0017] [Aspect 1] The present compound, wherein R1 is a C2-C6 open chain hydrocarbon group optionally having one or more substituents selected from Group A. [Aspect 2] The present compound, wherein R1 is a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B. [Aspect 3] The present compound, wherein R1 is a methyl group having one or more substituents selected from Group C. [Aspect 4] The present compound, wherein R1 is a C2-C6 open chain hydrocarbon group optionally having one or more substituents selected from Group A, or a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B. [Aspect 5] The present compound, wherein R1 is a C2-C6 open chain hydrocarbon group optionally having one or more substituents selected from Group A, or a methyl group having one or more substituents selected from Group C. [Aspect 6] The present compound, wherein R2 is a C1-C6 open chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect 7] The present compound, wherein R2 is a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B. [Aspect 8] The present compound, wherein R2 is OR6, SR7, S(O)R8, S(O)2R9, NRR11, C(O)R12, a nitro group, or a cyano group. [Aspect 9] The present compound, wherein R2 is a halogen atom. [Aspect 10] The present compound, wherein R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect 11] The present compound, wherein R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A. [Aspect 12] The present compound, wherein R3 is a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B). [Aspect 13] The present compound, wherein R3 is a phenyl group or a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may have one or more substituents selected from Group D).[Aspect 14] The compound of the present invention, wherein R3 is OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, or a hydroxy group. [Aspect 15] The compound of the present invention, wherein R3 is a halogen atom. [Aspect 16] The compound of the present invention, wherein R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom. [Aspect 17] The present compound, wherein R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, or a halogen atom. [Aspect 18] The present compound, wherein adjacent R3 and R4, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B). [Aspect 19] The present compound, wherein adjacent R3 and R4, together with the carbon atoms to which they are bonded, form a benzene ring or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally having one or more substituents selected from Group E). [Aspect 20] The present compound, wherein two adjacent pairs of R3 and R3, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5-6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B). [Aspect 21] The present compound, wherein two adjacent pairs of R3 and R3, together with the carbon atoms to which they are bonded, form a benzene ring or a 5-6-membered aromatic heterocycle (the benzene ring and the 5-6-membered aromatic heterocycle optionally have one or more substituents selected from Group E). [Aspect 22] The present compound, wherein R4 and R5 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom.[Aspect 23] The compound in which R4 and R5 are the same or different and represent a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, a halogen atom, or a hydrogen atom. [Aspect 24] The compound in which R4 and R5 are the same or different and represent OR22, SR23, S(O)R24, S(O)2R25, NR26R27, C(O)R28, a nitro group, a cyano group, a halogen atom, or a hydrogen atom. [Aspect 25] The compound in which R4 and R5 are the same or different and represent a halogen atom or a hydrogen atom. [Aspect 26] The compound in which R4 and R5 are a hydrogen atom. [Aspect 27] The compound in which n is 0. [Aspect 28] The compound in which n is 1. [Aspect 29] The compound in which n is 2. [Aspect 30] The compound wherein p is 0. [Aspect 31] The compound wherein p is 1. [Aspect 32] The compound wherein p is 2. [Aspect 33] The compound wherein q is 1. [Aspect 34] The compound wherein q is 2. [Aspect 35] The compound wherein q is 3. [Aspect 36] In the present compound, R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom; R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom; two adjacent R3s and R3s may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B}; and R4 and R5 are the same or different and are a halogen atom, or a hydrogen atom.[Embodiment 37] In the present compound, p is 0, R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, or a halogen atom, two adjacent R3s and R3s may be combined with the carbon atoms to which they are bonded to form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B}, and R4 and R5 are the same or different and are hydrogen atoms. [Aspect 38] In the present compound, R1 is a C2-C6 chain hydrocarbon group, R2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, R3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR13, SR14, S(O)R15, S(O)2R16, NR17R18, C(O)R19, C(R20)=NOR21, a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom, two adjacent R3 and R3 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle optionally having one or more substituents selected from Group B}, and R4 and R5 are the same or different and are a halogen atom, or a hydrogen atom. [Aspect 39] A method for controlling soybean rust fungi, which comprises treating soybeans or the soil in which soybeans are grown with the present compound. [Aspect 40] A method for controlling soybean rust fungi, which comprises treating soybeans or the soil in which soybeans are grown with the compound shown in Aspect 38.
[0018] Examples of Compound D of the present invention include the following compounds. [Aspect D1] Compound D of the present invention, wherein R1a is a C2-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect D2] Compound D of the present invention, wherein R1a is a cyclopropyl group optionally substituted with one or more halogen atoms. [Aspect D3] Compound D of the present invention, wherein R1a is a phenyl group optionally substituted with one or more halogen atoms. [Aspect D4] Compound D of the present invention, wherein R1a is a 5- to 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms. [Aspect D5] Compound D of the present invention, wherein R3a is a C1-C3 alkyl group. [Aspect D6] Compound D of the present invention, wherein R3a is a C1-C3 alkoxy group. [Aspect D7] Compound D of the present invention, wherein R3a is a cyclopropyl group optionally substituted with one or more halogen atoms. [Aspect D8] Compound D of the present invention, wherein R3a is a halogen atom. [Aspect D9] A compound of the present invention, wherein qa is 1. [Aspect D10] A compound of the present invention, wherein qa is 2. [Aspect D11] A compound of the present invention, wherein qa is 3. [Aspect D12] A compound of the present invention, wherein R1a is a C2-C3 alkyl group. [Aspect D13] A compound of the present invention, wherein R1a is a cyclopropyl group. [Aspect D14] A compound of the present invention, wherein R1a is a phenyl group. [Aspect D15] A compound of the present invention, wherein R1a is a 5- to 6-membered aromatic heterocyclic group. [Aspect D16] A compound of the present invention, wherein R1a is a C2-C3 alkyl group, a phenyl group, or a 5- to 6-membered aromatic heterocyclic group. [Aspect D17] A compound of the present invention, wherein R1a is a C2-C3 alkyl group, or a phenyl group. [Aspect D18] Compound D of the present invention, wherein R1a is a C2-C3 alkyl group or a 5- or 6-membered aromatic heterocyclic group. [Aspect D19] Compound D of the present invention, wherein R1a is a phenyl group or a 5- or 6-membered aromatic heterocyclic group. [Aspect D20] Compound D of the present invention, wherein R3a is a C1-C3 alkyl group or a halogen atom.[Aspect D21] A compound of Compound D of the present invention wherein R1a is a C2-C3 alkyl group, a phenyl group, or a 5- or 6-membered aromatic heterocyclic group, and R3a is a C1-C3 alkyl group or a halogen atom. [Aspect D22] A compound of Aspects D1 to D4, D12 to 19, or Compound D of the present invention wherein R3a is a C1-C3 alkyl group or a halogen atom. [Aspect D23] A compound of Aspects D1 to D4, D12 to 19, or Compound D of the present invention wherein R3a is a C1-C3 alkyl group. [Aspect D24] A compound of Aspects D1 to D4, D12 to 19, or Compound D of the present invention wherein R3a is a halogen atom. [Aspect D25] A method for controlling soybean rust, which comprises applying Compound D of the present invention to soybeans or the soil in which soybeans are grown. [Aspect D26] A method for controlling soybean rust, which comprises treating soybeans or the soil in which soybeans are grown with the compound represented by Aspect D21.
[0019] The following compounds are also examples of the compound D of the present invention: [Aspect C1] Formula (IIA) A compound represented by the formula: (wherein R1a is a C2-C3 alkyl group optionally substituted with one or more halogen atoms, or a cyclopropyl group optionally substituted with one or more halogen atoms, R3aA and R3aC are the same or different and are a C1-C3 alkyl group, a halogen atom, or a hydrogen atom, and R3aB is a C1-C3 alkyl group or a halogen atom.) [Aspect C2] A compound in Aspect C1 wherein R3aA and R3aC are the same or different and are a methyl group, a halogen atom, or a hydrogen atom, and R3aB is a methyl group or a halogen atom. [Aspect C3] A compound in Aspect C1 wherein R3aA and R3aC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, and R3aB is a methyl group or a halogen atom. [Aspect C4] A compound in Aspect C1 wherein R3aA and R3aC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, and R3aB is a methyl group, a fluorine atom, or a chlorine atom. [Aspect C5] A compound in Aspect C1 wherein R3aA and R3aC are the same or different and are a methyl group, a fluorine atom, or a hydrogen atom, and R3aB is a methyl group or a chlorine atom. [Aspect C6] A compound in Aspect C1 wherein R3aA and R3aC are the same or different and are a fluorine atom or a hydrogen atom, and R3aB is a methyl group or a chlorine atom. [Aspect C7] A compound in Aspect C1 wherein R3aA is a fluorine atom or a hydrogen atom, R3aB is a methyl group or a chlorine atom, and R3aC is a hydrogen atom. [Aspect C8] A compound in any of Aspects C1 to C7 wherein R1a is a C2-C3 alkyl group optionally substituted with one or more halogen atoms. [Aspect C9] The compound in any one of Aspects C1 to C7, wherein R 1a is an ethyl group or a propyl group. [Aspect C10] The compound in any one of Aspects C1 to C7, wherein R 1a is a cyclopropyl group.
[0020] Next, a method for producing the compound Y (including the compound of the present invention) will be described.
[0021] Production Method A A compound represented by formula (I-b) (hereinafter referred to as compound (I-b)) or a compound represented by formula (I-c) (hereinafter referred to as compound (I-c)) can be produced by reacting a compound represented by formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent. [In the formula, R represents a C2-C6 chain hydrocarbon group selected from Group A which may have one or more substituents, a C3-C8 alicyclic hydrocarbon group selected from Group B which may have one or more substituents, a 3-7 membered non-aromatic heterocyclic group selected from Group B which may have one or more substituents, a methyl group having one or more substituents selected from Group C, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may have one or more substituents selected from Group E}, and the other symbols have the same meanings as above.]
[0022] First, a method for producing compound (I-b) from compound (I-a) will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile and propionitrile (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 oxidizing agents used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be added as necessary. Examples of bases used in the reaction include sodium carbonate. When a base is used in the reaction, the base is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-a). Examples of catalysts used in the reaction include sodium tungstate. When a catalyst is used in the reaction, the catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (I-a). In the reaction, the oxidizing agent is typically used in a ratio of 1 to 1.2 moles per mole of compound (I-a). The reaction temperature is typically in the range of -20 to 80°C. The reaction time is typically in the range of 0.1 to 12 hours. After completion of the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent. The organic layer is washed, as necessary, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate). The organic layer is dried and concentrated to obtain compound (I-b).
[0023] Next, a method for producing compound (I-c) from compound (I-b) will be described. The reaction is typically carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of these. Examples of oxidizing agents used in the reaction include mCPBA and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be added as necessary. Examples of bases used in the reaction include sodium carbonate. When a base is used in the reaction, the base is typically used in a ratio of 0.01 to 1 mole per mole of compound (I-b). Examples of catalysts used in the reaction include sodium tungstate. When a catalyst is used in the reaction, the catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (I-b). The oxidizing agent is typically used in a ratio of 1 to 2 moles per mole of compound (I-b). The reaction temperature is typically within 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, which is then extracted with an organic solvent. The organic layer is washed, if necessary, with an aqueous solution of a reducing agent (e.g., sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate). The organic layer is dried and concentrated to obtain compound (I-c).
[0024] Compound (I-c) can also be produced in a one-step reaction (one-pot) by reacting compound (I-a) with an oxidizing agent. The reaction can be carried out using the oxidizing agent in a proportion of usually 2 to 5 moles per mole of compound (I-a) in accordance with the method for producing compound (I-c) from compound (I-b).
[0025] Production Method B Compound (I-a) can be produced by reacting a compound represented by formula (B1) (hereinafter referred to as compound (B1)) with a compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a base. [In the formula, X51 represents a chlorine atom, a bromine atom, an iodine atom, a mesyloxy group, or a triflyloxy group, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane (hereinafter referred to as DME) (hereinafter referred to as ethers); halogenated hydrocarbons; amides such as dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as NMP) (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles; water; and mixtures of two or more thereof. Examples of the base include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate (hereinafter referred to as alkali metal hydrogencarbonates); sodium hydride and tripotassium phosphate. A metal catalyst and / or a ligand may be used in the reaction, if necessary. Examples of the metal catalyst include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile)copper(I) hexafluorophosphate, and copper(I) 2-thiophenecarboxylate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and palladium catalysts such as palladium acetate, tris(dibenzylideneacetone)dipalladium(0), tetrakis(triphenylphosphine)palladium(0), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. When a metal catalyst is used in the reaction, the metal catalyst is usually used in a ratio of 0.01 to 1 mole per mole of compound (B1).Examples of the ligand include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, and N,N-dimethylglycine hydrochloride. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole per mole of compound (B1). In the reaction, compound (M1) is usually used in a ratio of 1 to 10 moles and base is usually used in a ratio of 1 to 10 moles per mole of compound (B1). 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 48 hours. After completion of the reaction, compound (I-a) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (M1) is known or can be produced according to known methods.
[0026] Production Method C The compound represented by formula (I) can be produced by reacting a compound represented by formula (B2) (hereinafter referred to as compound (B2)) with a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a palladium catalyst and a base. [In the formula, X represents a chlorine atom, a bromine atom, an iodine atom, or a triflyloxy group; M represents B(OH) or a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group; and the other symbols are as defined above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, dimethyl sulfoxide (hereinafter referred to as DMSO), water, and mixtures of two or more thereof. Examples of palladium catalysts used in the reaction include palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, sodium fluoride, and tripotassium phosphate. In the reaction, compound (M2) is usually used in a ratio of 0.5 to 2 moles, palladium catalyst is usually used in a ratio of 0.01 to 0.3 moles, and base is usually used in a ratio of 1 to 10 moles per mole of compound (B2). The reaction temperature is usually in the range of 0 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After completion of the reaction, the compound represented by formula (I) can be isolated by post-treatment procedures such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M2) is known or can be produced by a method similar to that known.
[0027] Production Method D The compound represented by formula (I) can be produced by reacting a compound represented by formula (B3) (hereinafter referred to as compound (B3)) with a compound represented by formula (M3) (hereinafter referred to as compound (M3)) in the presence of a palladium catalyst and a base. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method C, using compound (B3) instead of compound (B2) and compound (M3) instead of compound (M2). Compound (M3) is known or can be produced in accordance with a known method.
[0028] Production Method E Compound (I-a) can be produced by reacting a compound represented by formula (B4) (hereinafter referred to as compound (B4)) with a compound represented by formula (M4) (hereinafter referred to as compound (M4)) in the presence of a base. [In the formula, X53 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a mesyloxy group, or a triflyloxy group, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, amides, water, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, organic bases, sodium hydride, and tripotassium phosphate. When X53 represents a bromine atom, an iodine atom, or a triflyloxy group, a metal catalyst and a ligand may be added as necessary. Examples of metal catalysts used in the reaction include palladium catalysts such as palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride. When a metal catalyst is used in the reaction, the metal catalyst is typically used in a ratio of 0.01 to 1 mole per mole of compound (B4). Examples of ligands used in the reaction include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole per mole of compound (B4). In the reaction, compound (M4) is usually used in a ratio of 1 to 10 moles and a base is usually used in a ratio of 1 to 10 moles per mole of compound (B4). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-a) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.Compound (M4) is known or can be produced according to a known method.
[0029] Production Method F A compound represented by formula (I-e) (hereinafter referred to as compound (I-e)) can be produced by reacting a compound represented by formula (B6) (hereinafter referred to as compound (B6)) with a compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base. [In the formula, R29X represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R30X represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; R29X and R30X, together with the nitrogen atom to which they are bonded, may form a 3-7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B, or a 5-10-membered aromatic heterocyclic ring optionally having one or more substituents selected from Group E; the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures of two or more thereof. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, sodium hydride, and tripotassium phosphate. In the reaction, compound (M6) is usually used in a ratio of 1 to 10 moles and base is usually used in a ratio of 1 to 10 moles per mole of compound (B6). 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 48 hours. After completion of the reaction, compound (I-e) can be isolated by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M6) is known or can be produced according to known methods.
[0030] Reference Production Method A Compound (B1) can be produced by reacting compound (B4) with a sulfiding agent. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method E, except that a sulfurizing agent such as hydrogen sulfide is used in place of compound (M4).
[0031] Reference Production Method B Compound (B4) can be produced by reacting a compound represented by formula (C1) (hereinafter referred to as compound (C1)) with compound (M2) in the presence of a palladium catalyst and a base. [In the formula, X represents a bromine atom, an iodine atom, or a triflyloxy group, and the other symbols have the same meanings as above.] The reaction can be carried out using compound (C1) instead of compound (B2) in accordance with Production Method C. Compound (C1) is known or can be produced in accordance with a known method.
[0032] Reference Production Method C A compound represented by formula (C3) (hereinafter referred to as compound (C3)) can be produced by reacting a compound represented by formula (C2) (hereinafter referred to as compound (C2)) with compound (M1) in the presence of a base. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method B, except that compound (C2) is used in place of compound (B1). Compound (C2) is known or can be produced in accordance with a known method.
[0033] Reference Production Example D A compound represented by formula (C4) (hereinafter referred to as compound (C4)) or a compound represented by formula (C5) (hereinafter referred to as compound (C5)) can be produced by reacting compound (C3) with an oxidizing agent. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method A, except that compound (C3) is used in place of compound (I-a) and compound (C4) is used in place of compound (I-b).
[0034] Reference Production Method E The compound represented by formula (C6) (hereinafter referred to as compound (C6)) can be produced by reacting compound (B2) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method C, except that bis(pinacolato)diboron is used in place of Compound (M2).
[0035] Reference Production Method F Compound (B6) can be produced from a compound represented by formula (C10) (hereinafter referred to as compound (C10)). [In the formula, X represents SH or S(O)OH, and the other symbols have the same meanings as defined above.] The reaction can be carried out in accordance with the method described in WO 2016 / 204096 or the method described in Tetrahedron Letters, 2017, 58, 2244-2247. Compound (C10) is known or can be produced in accordance with a known method.
[0036] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate formulations or in a single formulation. One aspect of the present invention is a composition containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (i.e., the present component), and the compound of the present invention. Another 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) (i.e., the present component), and the compound of the present invention.
[0037] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of classes 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, acaricidal, and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.
[0038] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.
[0039] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).
[0040] Group (d) is a group of repellent ingredients.
[0041] Examples of combinations of the present component and the compound of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to any one of the present compounds selected from the compound group SX1 to SX54. The present components described below are all known components and can be obtained from commercially available preparations or produced by known methods. When the present component is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).
[0042] Combinations of the present ingredient of the above group (a) with the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX,Bioresmethrin + SX, bistrifluron + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, cartap hydrochloride + SX, cartap + SX Chinomethionate + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A 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, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, Dinotefuran + SX, disodium octaborate + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX,Dried leaves of Dryopteris filix (mas) + SX, emamectin benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethifencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX. Etoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX, Viscum album extract + SX, Famphur + SX, Fenamiphos + SX Fenazaquin + SX,Fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, Flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX,Furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, Imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX Kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX,Lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, Methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine sulfate + SX, Nitenpyram + SX, Novaluron + SX, Noviflumuron + SX,Chenopodium anthelminticum seed oil + 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, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, Tebupirimfos + SX, Teflubenzuron + SX, Tefluthrin + SX, Temephos + SX, Terbufos + SX,Terpene constituents of the extract of Chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, Thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, Triflumuron + SX, trimethacarb + SX,Tyclopyrazoflor + SX, umifoxolaner + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, 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, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX,N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 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 Cry1Ac (BT crop protein Cry1Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein mCry3A (BT crop protein mCry3A) + SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab) + SX, BT crop protein Cry3Bb (BT crop protein Cry3Bb) + SX, BT crop protein Cry34Ab1 / Cry35Ab1 (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 SX, Helicoverpa armigera NPV strain BV-0003 + SX,Helicoverpa zea nucleopolyhedrosis virus (NPV) + SX, Lymantria dispar nucleopolyhedrosis virus (NPV) + SX, Mamestra brassicae nucleopolyhedrosis virus (NPV) + SX, Mamestra configurata nucleopolyhedrosis virus (NPV) + SX, Neodiprion abietis nucleopolyhedrosis virus (NPV) + SX, Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrovirus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (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 firmus strain NCIM2637 + SX SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX,Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306) + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX,Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX,Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX,Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,
[0043] Combinations of the present ingredient of the above group (b) with the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX, 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, tea tree extract (Melaleuca alternifolia) + SX, extract of Reynoutria sachalinensis (Japanese knotweed) + SX, extract of the cotyledons of lupine plantlets ("BLAD") + SX, garlic extract (Allium sativum extract) + SX, horsetail extract (Equisetum arvense extract) + SX, nasturtium extract (Tropaeol majus extract) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX,Fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, Fosetyl + SX, fosetyl-aluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX,Guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX Isofetamide + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak 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, metarylpicoxamid + SX,Metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, Oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, Potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX,Probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, Pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, quinoa saponins Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX,Simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, 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,マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX,4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX,methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, 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-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX,3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX,1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,(5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX,N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, Agrobacterium strain K1026 + SX, Agrobacterium strain K84 + SX amyloliquefaciens strain PTA-4838 (Aveo(TM) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX,Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX,Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX,Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX,Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,
[0044] Combinations of the present ingredient in group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, Cyclanilide + SX,Daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A + SX, gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + 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. ,
[0045] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.
[0046] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like.
[0047] The present compound, the present compound Y, the compound of the present invention, or composition A can control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, Phytomyxea, and bacteria. Examples of fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following: The scientific name of the plant pathogenic microorganism that causes each disease is shown in parentheses.
[0048] Diseases of 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 panicle blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), sheath blight-like symptoms (red sclerotium pathogen (Waitea circinata), brown sclerotium pathogen (Ceratobasidium setariae), brown sheath blight pathogen (Thanatephorus cucumeris)); Diseases of wheat: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), brown rust (Puccinia recondita), pink snow mold (Microdochium nivale, Microdochium majus), snow scab (Typhula incarnata, Typhula ishikariensis), large snow scab (Sclerotinia borealis), brown snow rot (Pythium spp.), loose smut (Ustilago tritici), common bunt (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Stagonospora nodorum), tan spot (Pyrenophora tritici-repentis), seedling blight caused by Rhizoctonia solani, foot rot (Gaeumannomyces graminis), blast (Pyricularia graminis-tritici);Barley diseases: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), ear bunt (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), leaf spot (Ramularia collo-cygni), seedling damping-off (Rhizoctonia solani); corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty blight (Setosphaeria turcica), tropical rust (Physopella zeae), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma maydis, tar spot (Phyllachora maydis);Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola); coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); rapeseed diseases: sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae); sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger;Apple diseases: Monilinia mali, canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: black spot (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red spot (Gymnosporangium haraeanum); Peach diseases: brown rot (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), leaf crinkle (Taphrina deformans); grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola); persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf drop (Cercospora kaki, Mycosphaerella nawae); fig diseases: rust (Phakopsora nishidana);Cucurbit diseases: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Blight (Didymella bryoniae), Brown spot (Corynespora cassiicola), Blight (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Late blight (Phytophthora capsici), Damping-off (Pythium sp.), Root rot (Phomopsis sp.); Tomato diseases: Ring spot (Alternaria solani), Leaf mold (Cladosporium fulvum), Sooty mold (Pseudocercospora fuligena), Late blight (Phytophthora infestans), Powdery mildew (Leveillula taurica); Eggplant diseases: Brown spot (Phomopsis vexans), Powdery mildew (Erysiphe cichoracearum); Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida); Diseases of leeks: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotial rot (Botrytis squamosa);Soybean diseases: Purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Diseases of peanuts: black spot (Cercospora personata), brown spot (Cercospora arachidicola), southern blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);Potato diseases: summer blight (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), canker (Synchytrium endobioticum); strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum); tea diseases: net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), ring spot (Pestalotiopsis Diseases of tobacco: red spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); Diseases of sugar beet: brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root rot (Aphanomyces cochlioides), rust (Uromyces betae); Diseases of rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases of chrysanthemum: brown spot (Septoria chrysanthemi indici), white rust (Puccinia horiana); Onion diseases: white spotted leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotial rot (Botrytis squamosa);Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), southern blight (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); diseases of radish: black spot (Alternaria brassicicola); diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), and red blight (Pythium aphanidermatum); diseases of banana: Sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola); diseases of lentil: Ascochyta (Ascochyta lentis); Chickpea diseases: Ascochyta (Ascochyta rabiei); Bell pepper diseases: Anthracnose (Colletotrichum scovillei); Mango diseases: Anthracnose (Colletotrichum acutatum); Sweet potato diseases: Root rot (Diaporthe destruens); Fruit tree diseases: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa); Post-harvest diseases of apples, pears, etc.: Mucor rot (Mucor piriformis); Seed diseases or diseases in the early stages of growth caused by species of the genera 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 the Polymyxa genus (e.g., Polymyxa betae and Polymyxa graminis);Diseases caused by bacteria: rice seedling bacterial blight (Burkholderia plantarii), rice inner glume browning disease (Pantoea ananatis), rice bacterial leaf blight (Xanthomonas oryzae pv. oryzae.), cucumber bacterial spot (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), corn Goss's wilt (Clavibacter michiganensis), Pierce's disease (Xylella fastidiosa) of grapes, olives, peaches, etc., and crown gall (Agrobacterium tumefaciens) of Rosaceae plants such as apples, peaches, and cherries. ;
[0049] The soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, resulting in the F129L amino acid substitution, and is therefore resistant to QoI fungicides.
[0050] The method for controlling plant diseases of the present invention is carried out by applying an effective amount of the present compound, the present compound Y, the present compound, or composition A to plants or the soil in which plants are grown. Examples of the treatment method include foliage treatment, soil treatment, and seed treatment.
[0051] The present compound, the present compound Y, the compound of the present invention, or composition A is typically mixed with an inert carrier such as a solid carrier or a liquid carrier and a surfactant, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate the compound into an aqueous suspension, oil suspension, oil concentrate, emulsifiable concentrate, emulsion, microemulsion, microcapsule, wettable powder, water dispersible granule, dust, granule, or other formulation. The compound is not limited to these formulations, and can also be formulated into the dosage forms described in "Manual on development and use of FAO and WHO Specifications for pesticides," FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the present compound, the present compound Y, the compound of the present invention, or composition A.
[0052] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
[0053] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).
[0054] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).
[0055] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc., and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.
[0056] Furthermore, an adjuvant can be used as a component that enhances or supports the efficacy of the present compound, the present compound Y, the compound of the present invention, or composition A. Specific examples of such adjuvants include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).
[0057] In the present invention, plants include whole plants and specific parts of plants, such as stems, leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.
[0058] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that can grow when separated from the main body and placed in soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, and tuberous roots are collectively called bulbils. Potato cultivation begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
[0059] Seedlings include seedlings and saplings.
[0060] Examples of methods for controlling plant diseases by applying an effective amount of the present compound, the present compound Y, the compound of the present invention, or composition A to soil include methods of applying an effective amount of the present compound, the present compound Y, the compound of the present invention, or composition A to soil before or after planting a plant. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), plant base treatment (spraying in planting holes, mixing in plant base soil, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (spraying in planting furrows, mixing in planting furrow soil), row treatment (row spraying, row soil mixing, row spraying in the growing season), row treatment at sowing (row spraying at sowing, mixing in row soil at sowing), overall treatment (overall soil spraying, overall soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (foliar spraying of granules during the growing season, spraying under the crown or around the main trunk, soil surface spraying, soil surface mixing, seeding hole spraying, furrow surface spraying, spraying between plants), and others. Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling bed treatments (seedling bed spraying, seedling bed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (hilling soil mixing, plowing in, topsoil mixing, rain-drop soil mixing, planting position treatment, granular inflorescence spraying, paste fertilizer mixing).
[0061] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the present compound, Compound Y, the compound of the present invention, or Composition A. More specifically, examples include spray treatments in which a suspension of the present compound, Compound Y, the compound of the present invention, or Composition A is sprayed onto the surface of seeds or vegetative reproductive organs; smear treatments in which the present compound, Compound Y, the compound of the present invention, or Composition A is applied to seeds or vegetative reproductive organs; immersion treatments in which seeds or vegetative reproductive organs are immersed in a solution of the present compound for a certain period of time; and methods of coating seeds or vegetative reproductive organs with a carrier containing the present compound, Compound Y, the compound of the present invention, or Composition A (film coating treatment, pellet coating treatment, etc.). Seed potatoes are particularly examples of the above-mentioned vegetative reproductive organs. In the present invention, seeds or vegetative reproductive organs carrying the present compound, Compound Y, the compound of the present invention, or Composition A refer to seeds or vegetative reproductive organs to which the present compound, Compound Y, the compound of the present invention, or Composition A is attached. The seeds or vegetative reproductive organs carrying the present compound, compound Y, the compound of the present invention, or composition A may have materials other than the present compound, compound Y, the compound of the present invention, or composition A attached to them before or after the present compound, compound Y, the compound of the present invention, or composition A is attached to the seeds or vegetative reproductive organs. Furthermore, when composition A is attached to the surface of the seeds or vegetative reproductive organs as a layer, the layer may consist of one layer or multiple layers. Furthermore, when multiple layers are attached, each layer may contain one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer containing no active ingredients. The seeds or vegetative reproductive organs carrying the present compound, compound Y, the compound of the present invention, or composition A can be obtained, for example, by applying a formulation containing the present compound, compound Y, the compound of the present invention, or composition A to the seeds or vegetative reproductive organs by the seed treatment method described above.
[0062] The application rate of the present compound, the present compound Y, the compound of the present invention, or Composition A varies depending on weather conditions, formulation, application time, application method, application location, target disease, target crop, etc., but is usually 1 to 500 g per 1,000 m2 in the case of foliar application or soil application. In the case of seed treatment, the amount of the present compound, the present compound Y, the compound of the present invention, or Composition A is usually 0.001 to 100 g per kg of seeds. When the present compound, the present compound Y, the compound of the present invention, or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable powder, etc., it is usually diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm before application, and dusts, granules, etc. are usually applied as is.
[0063] The present compound, the present compound Y, the compound of the present invention, or composition A can be used as an agent for controlling plant diseases in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.
[0064] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, 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, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,
[0065] The above-mentioned plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred 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 that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.
[0066] The present invention will be explained in more detail below by showing Production Examples, Reference Production Examples, Formulation Examples and Test Examples, but the present invention is not limited to these examples.
[0067] 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, Ph represents a phenyl group, Bn represents a benzyl group, N-pyrrolidinyl represents an N-pyrrolidinyl group, and 2-pyrimidyl represents a 2-pyrimidyl group. "Ph" represents a 2-pyrazinyl group, "4-pyrimidyl" represents a 4-pyrimidyl group, "2-Py" represents a 2-pyridyl group, "3-Py" represents a 3-pyridyl group, "4-Py" represents a 4-pyridyl group, "2-furyl" represents a 2-furyl group, "3-furyl" represents a 3-furyl group, "2-thienyl" represents a 2-thienyl group, and "3-thienyl" represents a 3-thienyl group. If Ph has a substituent, the substituent and its position are written before the symbol. For example, 3,5-diF-Ph represents a 3,5-difluorophenyl group.
[0068] When the physical properties of the compound were measured by gas chromatography (GC) / mass spectrometry (MS) (hereinafter referred to as GCMS), the measured molecular ion value [M] and retention time (hereinafter referred to as RT) are recorded. The GC conditions are as follows: [GC analysis conditions] Instrument: HP 7890A (Agilent) Column: HP-5MS (0.25 μm × 0.25 mm × 30 m) (Agilent) Injection port temperature: 250°C Control mode: linear velocity, pressure: 14.7 psi, linear velocity: 23.98 cm / sec Carrier gas: helium Flow rate: 1 mL / min Injection volume: 1.0 μL (split ratio 200:1) Oven temperature: 70°C (2 min) → 15°C / min → 300°C (2.67 min) [MS analysis conditions] Detector: 5975C inert XL MSD (Agilent) Ionization method: EI Ionization voltage: 69.9 eV, ion source temperature: 230°C
[0069] When the physical properties of a compound were measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H]+, [M+H+MeCN]+, or [M-H]- and retention time (hereinafter referred to as RT) are reported. The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) were as follows. [LC Conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: Two LC-20AD (Shimadzu Corporation) pumps (high-pressure gradient) Gradient conditions: Solution was delivered at the concentration gradient described in [Table LC1].
[0070] [MS conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization method: DUIS
[0071] First, a production example of the compound Y (including the compound of the present invention) will be shown.
[0072] Preparation Example 1 A mixture of 0.43 g of 1-bromo-3-(ethylsulfanyl)benzene, 0.33 g of 4-chlorophenylboronic acid, 0.15 g of {1,1'-bis(diphenylphosphino)ferrocene}dichloropalladium(II), 1.28 g of tripotassium phosphate, 4 mL of DME, and 0.1 mL of water was stirred under reflux for 8 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 0.22 g of Compound 1 represented by the following formula: Compound 1: 1H-NMR (CDCl3) δ: 7.52-7.48 (3H, m), 7.43-7.39 (2H, m), 7.37-7.34 (2H, m), 7.33-7.29 (1H, m), 3.00 (2H, q), 1.35 (3H, t).
[0073] Preparation Example 1-1 The compound prepared in accordance with Preparation Example 1 and its physical properties are shown below. Formula (A-1) (hereinafter referred to as compound (A-1)), wherein n, R1, R2A, R2B, R2C, R2D, R3A, R3B, R3C, R4 and R5 are any combination described in [Table A-1] and [Table A-1A].
[0074] [Table A-1]
[0075] [Table A-1A]
[0076] Compound 2: 1H-NMR (CDCl3) δ: 7.45 (1H, br s), 7.39-7.30 (3H, m), 7.19 (2H, d), 3.01 (2H, q), 1.35 (3H, t). Compound 5: 1H-NMR (CDCl3) δ: 7.51-7.50 (1H, m), 7.37-7.33 (2H, m), 7.33-7.20 (4H, m), 3.00 (2H, q), 2.31 (3H, d), 1.35 (3H, t). Compound 6: 1H-NMR (CDCl3) δ: 7.50-7.47 (1H, m), 7.36-7.28 (4H, m), 7.02 (1H, dq), dt), 7.40-7.23 (5H, m), 2.99 (2H, q), 2.40 (3H, s), 1.34 (3H, t). Compound 8: 1H-NMR (CDCl3) δ: 7.49-7.27 (7H, m), 3.00 (2H, q), 1.35 (3H, t). Compound 9: 1H-NMR (CDCl3) δ: 7.46 (1H, t), 7.33-7.26 (3H, m), 2. dt), 7.21-7.16 (2H, m), 2.96 (2H, t), 1.34 (3H, t). 1.71 (2H, dq), 1.05 (3H, t). Compound 14: 1H-NMR (CDCl3) δ: 7.50 (1H, br s), 7.36-7.27 (3H, m), 7.27-7.19 (3H, m), 2.95 (2H, t), 2.31 (3H, d), 1.71 (2H, dq), 1.04 (3H, t). Compound 19: 1H-NMR (CDCl3) δ: 7.52 (1H, dd), 7.36 (1H, dt), 7.33 (1H, td), 7.29 (1H, dt), 7.19 (2H, br s), 7.01 (1H, br s), 2.95 (2H, dd), 2.38 (6H, br s), 1.70 (2H, td), 1.04 (3H, t). Compound 33: 1H-NMR (CDCl3) δ: 7.47 (1H, td), 7.38-7.29 (3H, m), 7.10-7.01 (2H, m), 2.95 (2H, t), 2.23 (3H, br s), 1.71 (2H, td), 1.05 (3H, t). Compound 34: 1H-NMR (CDCl3) δ: 7.53-7.52 (1H, m), 7.39-7.17 (6H, m), 2.94 (2H, t), 2.33 (3H, s), 2.31 (3H, s), 1.70 (2H, td), 1.04 (3H, t). Compound 35: 1H-NMR (CDCl3) δ: 7.53 (1H, t), 7.43 (1H, br s), d), 2.98 (2H, t), 1.71-1.63 (2H, m), 1.53-1.43 (2H, m), 0.94 (3H, t). Compound 41: 1H-NMR (CDCl3) δ: 7.38-7.26 (5H, m), 3.00-2.82 (6H, m), 2.16-2.08 (2H, m), 1.70 (2H, td), 1.03 (3H, t). Compound 42: 1H-NMR (CDCl3) δ: 7.45-7.44 (1H, m), 7.39-7.29 (3H, m), 7.19 (2H, d), 2.98 (2H, t), 1.71-1.63 (2H, m), 1.53-1.43 (2H, m), 0.94 (3H, t). (2H, d), 3.24 (1H, td), 1.74-1.51 (2H, m), 1.31 (3H, d), 1.03 (3H, t). Compound 43: 1H-NMR (CDCl3) δ: 7.36-7.25 (9H, m), 7.09 (2H, d), 4.15 (2H, s). Compound 44: 1H-NMR (CDCl3) δ: 7.49 (1H, td), 7.41 (1H, dt), 7.37 (1H, td), 7.27 (1H, dt), 7.19 (2H, d), 2.27-2.20 (1H, m), 1.15-1.10 (2H, m), 0.76-0.71 (2H, m). Compound 45: GCMS: 357 [M] +, RT = 19.4 min. Compound 46: GCMS: 331 [M] +, RT = 17.4 min. Compound 55: GCMS: 288 [M] +, RT = 13.1 min. Compound 56: GCMS: 324 [M] +, RT = 12.8 min. Compound 60: GCMS: 382 [M] +, RT = 18.1 min. Compound 61: GCMS: 360 [M] +, RT = 19.6 min. Compound 62: GCMS: 310 [M] +, RT = 16.6 min. Compound 66: 1H-NMR (CDCl3) δ: 7.43-7.41 (1H, m), 7.38-7.31 (2H, m), 7.29-7.25 (1H, m), 7.19-7.14 (2H, m), 2.98-2.93 (2H, m), 1.77-1.66 (2H, m), 1.05 (3H, t). Compound 67: 1H-NMR (CDCl3) δ: 7.49-7.47 (1H, m), 7.40-7.30 (3H, m), 7.12-7.04 (2H, m), 6.83-6.76 (1H, m), 2.96 (2H, t), 1.76-1.66 (2H, m), 1.05 (3H, t). Compound 72: 1H-NMR (CDCl3) δ: 7.28-7.18 (4H, m), 7.05-6.95 (2H, m), 2.95 (2H, t), 2.31 (3H, d), 1.78-1.66 (2H, m), 1.05 (3H, t).Compound 75: LCMS: 367 [M+H] +, RT = 2.00 min Compound 76: GCMS: 366 [M] +, RT = 17.8 min Compound 77: LCMS: 367 [M+H] +, RT = 2.06 min Compound 78: LCMS: 366 [M+H] +, RT = 2.10 min Compound 79: LCMS: 366 [M+H] +, RT = 2.07 min Compound 80: LCMS: 366 [M+H] +, RT = 2.08 min.
[0077] Preparation Example 2: To a mixture of 0.44 g of Compound 2 and 4 mL of chloroform, 0.50 g of mCPBA (75% purity, 25% water content) was added at 0°C and stirred at room temperature for 3 hours. To the resulting mixture, 10 mL of saturated aqueous sodium thiosulfate solution and 10 mL of saturated aqueous sodium bicarbonate solution were added, and the mixture was stirred for 1 hour, followed by extraction with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 0.23 g of Compound 4 and 0.15 g of Compound 26, which are represented by the following formula: Compound 4: 1H-NMR (CDCl3) δ: 8.07 (1H, t), 7.95 (1H, dt), 7.82 (1H, ddd), 7.69 (1H, t), 7.28-7.23 (2H, m), 3.18 (2H, q), 1.33 (3H, t).
[0078] Compound 26: 1H-NMR (CDCl3) δ: 7.83-7.81 (1H, m), 7.67-7.57 (3H, m), 7.29-7.23 (2H, m), 3.01-2.93 (1H, m), 2.85-2.77 (1H, m), 1.25 (3H, t).
[0079] Preparation Example 2-1 Compounds prepared according to Preparation Example 2 and their physical properties are shown below: Compound (A-1) in which n, R1, R2A, R2B, R2C, R2D, R3A, R3B, R3C, R4 and R5 are any combinations described in [Table A-2] and [Table A-2A].
[0080] [Table A-2]
[0081] [Table A-2A]
[0082] Compound 3: 1H-NMR (CDCl3) δ: 8.09 (1H, t), 7.90 (1H, ddd), 7.84 (1H, ddd), 7.66 (1H, t), 7.55 (2H, ddd), 7.46 (2H, ddd), 3.17 (2H, q), 1.32 (3H, t). Compound 11: 1H-NMR (CDCl3) δ: 8.09 (1H, t), 7.88 (1H, dt), 7.84 (1H, dt), 7.64 (1H, t), 7.32-7.28 (3H, m), 3.17 (2H, q), 2.34 (3H, d), 1.32 (3H, t). Compound 12: 1H-NMR (CDCl3) δ: 7.82-7.82 (1H, m), 7.68 (1H, dt), 7.60-7.52 (2H, m), 7.33-7.24 (3H, m), 3.01-2.91 (1H, m), 2.88-2.76 (1H, m), 2.33 (3H, d), 1.24 (3H, t). Compound 15: 1H-NMR (CDCl3) δ: 8.07 (1H, q), 7.89 (1H, dq), 7.83 (1H, dq), 7.63 (1H, t), 7.35 (1H, t), 7.06 (1H, dd), 7.01 (1H, dd), 3.16 (2H, q), 2.41 (3H, s), 1.32 (3H, t). Compound 16: 1H-NMR (CDCl3) δ: 7.76 (1H, br s), 7.69-7.64 (1H, m), 7.61-7.55 (2H, m), 7.35 (1H, t), 7.04 (1H, dt), 6.99 (1H, dd), 3.00-2.90 (1H, m), 2.86-2.77 (1H, m), 2.40 (3H, s), 1.24 (3H, t). Compound 17: 1H-NMR (CDCl3) δ: 8.11 (1H, t), 7.88-7.84 (2H, m), 7.62 (1H, t), 7.52 (2H, d), 7.29 (2H, d), 3.16 (2H, q), 2.42 (3H, s), 1.31 (3H, t). Compound 18: 1H-NMR (CDCl3) δ: 7.83 (1H, td), 7.70 (1H, dt), 7.59-7.50 (4H, m), 7.27 (2H, d), 3.00-2.90 (1H, m), 2.86-2.76 (1H, m), 2.41 (3H, s), 1.23 (3H, t). Compound 20: 1H-NMR (CDCl3) δ: 8.06 (1H, t), 7.95 (1H, dq), 7.81 (1H, dq), 7.68 (1H, td), 7.28-7.23 (2H, m), 3.14-3.10 (2H, m), 1.83-1.75 (2H, m), 1.03 (3H, t). Compound 21: 1H-NMR (CDCl3) δ: 7.84-7.83 (1H, m), 7.67-7.62 (1H, m), 7.62-7.58 (2H, m), 7.29-7.24 (2H, m), 2.85-2.79 (2H, m), 1.91-1.79 (1H, m), 1.76-1.65 (1H, m), 1.08 (3H, t). Compound 22: GCMS: 298 [M] +, RT = 17.6 min Compound 23: 1H-NMR (CDCl3) δ: 7.84-7.34 (7H, m), 3.01-2.89 (1H, m), 2.86-2.73 (1H, m), 1.24 (3H, t). Compound 24: 1H-NMR (CDCl3) δ: 8.09 (1H, t), 7.88 (1H, dq), 7.83 (1H, dq), 7.63 (1H, t), 7.32-7.25 (3H, m), 3.13-3.09 (2H, m), 2.34 (3H, d), 1.83-1.73 (2H, m), 1.02 (3H, t). Compound 25: 1H-NMR (CDCl3) δ: 7.83 (1H, t), 7.68 (1H, dt), 7.61-7.55 (2H, m), 7.34-7.24 (3H, m), 2.89-2.75 (2H, m), 2.33 (3H, d), 1.89-1.80 (1H, m), 1.76-1.65 (1H, m), 1.07 (3H, t). Compound 27: 1H-NMR (CDCl3) δ: 8.14 (1H, t), 7.95 (1H, dq), 7.89 (1H, dq), 7.77-7.67 (5H, m), 3.18 (2H, q), 1.33 (3H, t). Compound 28: 1H-NMR (CDCl3) δ: 7.89 (1H, td), 7.75-7.71 (5H, m), 7.63 (1H, td), 7.59 (1H, dt), 3.01-2.93 (1H, m), 2.87-2.78 (1H, m), 1.25 (3H, t). Compound 29: 1H-NMR (CDCl3) δ: 8.04 (1H, t), 7.84 (1H, dq), 7.79 (1H, dq), 7.61 (1H, t), 7.12-7.07 dt), 7.55 (1H, td), 7.51 (1H, dt), 7.11-7.08 (2H, m), 6.90 (1H, d), 6.02 (2H, s), 3.00-2.90 (1H, m), 2.85-2.76 (1H, m), 1.24 (3H, t). Compound 31: 1H-NMR (CDCl3) δ: 8.11 (1H, t), 7.86 (1H, dt), 7.55 (1H, td), 7.51 (1H, dt), 7.11-7.08 (2H, m), 6.90 (1H, d), 6.02 (2H, s), 3.00-2.90 (1H, m), 2.85-2.76 (1H, m), 1.24 (3H, t). 3H, t), 7.61 (1H, t), 7.24 (2H, br s), 7.06 (1H, s), 3.14-3.08 (2H, m), 2.40 (6H, s), 1.82-1.73 (2H, m), 1.01 (3H, t). 32: 1H-NMR (CDCl3) δ: 7.85 (1H, t), 7.70 (1H, dt), 7.58-7.52 (2H, m), 7.24 (2H, br s), 7.04 (1H, br s), 2.89-2.75 (2H, m), 2.39 (6H, s), 1.90-1.78 (1H, m), 1.78-1.66 (1H, m), 1.06 (3H, t). This compound 36: 1H-NMR (CDCl3) δ: 8.06 (1H, t), 7.91 (1H, dq), 7.81 (1H, dq), 7.65 (1H, t), 7.1H-NMR (CDCl3) δ: 7.82 (1H, dd), 7.67-7.56 (3H, m), 7.13 (2H, d), 2.87-2.76 (2H, m), 2.24 (3H, s), 1.90-1.79 (1H, m), 1.77-1.66 (1H, m), 1.07 (3H, t). Compound 38: 1H-NMR (CDCl3) δ: 8.10 (1H, t), 7.88-7.82 (2H, m), 7.64-7.58 (1H, m), 7.41 (1H, d), 7.36 (1H, dd), 7.24 (1H, d), 3.12-3.08 (2H, m), 2.35 (3H, s), 2.32 (3H, s), 1.82-1.73 (2H, m), 1.01 (3H, t). 1H-NMR (CDCl3) δ: 8.10 (1H, t), 7.87-7.83 (2H, m), 7.61 (1H, t), 7.49 (1H, s), 7.39 (1H, dd), 7.33 (1H, d), 3.13-3.08 (2H, m), 2.98 (4H, q), 4H, t), 2.18-2.10 (2H, m), 1.82-1.73 (2H, m), 1.00 (3H, t). 1H-NMR (CDCl3) δ: 7.84 (1H, td), 7.70 (1H, dt), 7.58-7.53 (2H, m), 7.49 (1H, br s), 7.40 (1H, dd), 7.31 (1H, d), 2.96 (4H, q), 2.89-2.75 (2H, m), 2.17-2.09 (2H, m), 1.88-1.65 (2H, m), 1.06 (3H, t).Compound 47: GCMS: 344 [M]+, RT = 18.2 min Compound 48: LCMS: 329 [M+H] +, RT = 2.16 min Compound 49: GCMS: 344 [M] +, RT = 17.9 min Compound 50: LCMS: 329 [M+H] +, RT = 2.14 min Compound 51: LCMS: 379 [M+H] +, RT = 2.22 min Compound 52: LCMS: 363 [M+H] +, RT = 2.17 min Compound 53: GCMS: 328 [M] +, RT = 18.1 min Compound 54: LCMS: 313 [M+H] +, RT = 1.98 min Compound 57: GCMS: 320 [M] +, RT = 14.5 min Compound 58: GCMS: 356 [M] +, RT = 14.2 min Compound 59: GCMS: 340 [M] +, RT = 14.3 min Compound 63: GCMS: 414 [M] +, RT = 19.5 min Compound 64: LCMS: 393 [M+H] +, RT = 2.29 min Compound 65: LCMS: 384 [M+H+MeCN] +, RT = 2.15 min Compound 68: LCMS: 281 [M+H] +, RT = 1.91 min Compound 69: GCMS: 296 [M]+, RT = 16.2 min Compound 70: LCMS: 299 [M+H] +, RT = 1.96 min Compound 71: GCMS: 314 [M] +, RT = 16.3 min Compound 73: GCMS: 310 [M] +, RT = 16.8 min Compound 74: LCMS: 295 [M+H] +, RT = 2.08 min.
[0083] Reference Production Example 1 Under an argon atmosphere, a mixture of 10.0 g of 1-bromo-3-(propylsulfanyl)benzene, 1.6 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 13.2 g of bis(pinacolato)diboron, 8.5 g of potassium acetate, and 100 mL of DMSO was stirred at 90°C for 8 hours. The resulting mixture was cooled to room temperature, and water was added thereto, followed by filtration. MTBE was added to the resulting filtrate, and the mixture was washed successively with water and saturated brine. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 10.2 g of Intermediate 1 represented by the following formula: Intermediate 1: 1H-NMR (CDCl3) δ: 7.77 (1H, br s), 7.60 (1H, ddd), 7.42 (1H, ddd), 7.29 (1H, dd), 2.92 (2H, t), 1.66 (2H, td), 1.34 (12H, s), 1.02 (3H, t).
[0084] The present compounds and examples of the present compounds produced according to the above-mentioned production methods and production examples are shown below: Compounds represented by formula (A-1), in which n is 0, R2A, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in combination A (hereinafter referred to as compound group SX1).
[0085] Combination A consists of substituent numbers A1 to A660. Substituent numbers A1 to A660 represent combinations of R1, R3A, R3B, R3C, R4, and R5 in the compound represented by formula (A-1), and are hereinafter referred to as [substituent numbers: R1, R3A, R3B, R3C, R4, R5]. For example, substituent number A5 represents a combination in which R1 is an ethyl group, R3A, R3B, and R3C are each methyl groups, and R4 and R5 are hydrogen atoms.
[0086] [R1,R3A,R3B,R3C,R4,R5]: [A1;Et,Me,H,H,H,H]、[A2;Et,H,Me,H,H,H]、[A3;Et,Me,Me,H,H,H]、[ A4;Et,Me,H,Me,H,H]、[A5;Et,Me,Me,Me,H,H]、[A6;Et,F,H,H,H,H]、[ A7;Et,H,F,H,H,H]、[A8;Et,F,F,H,H,H]、[A9;Et,F,H,F,H,H]、[A10;E t,F,F,F,H,H]、[A11;Et,Cl,H,H,H,H]、[A12;Et,H,Cl,H,H,H]、[A13;E t,Cl,Cl,H,H,H]、[A14;Et,Cl,H,Cl,H,H]、[A15;Et,Cl,Cl,Cl,H,H]、[ A16;Et,Br,H,H,H,H]、[A17;Et,H,Br,H,H,H]、[A18;Et,Br,Br,H,H,H] 、[A19;Et,Br,H,Br,H,H]、[A20;Et,Br,Br,Br,H,H]、[A21;Et,I,H,H,H ,H]、[A22;Et,H,I,H,H,H]、[A23;Et,I,I,H,H,H]、[A24;Et,I,H,I,H,H] 、[A25;Et,I,I,I,H,H]、[A26;Et,Et,H,H,H,H]、[A27;Et,H,Et,H,H,H] 、[A28;Et,Et,H,Et,H,H]、[A29;Et,CF3,H,H,H,H]、[A30;Et,H,CF3,H, H,H]、[A31;Et,CF3,H,CF3,H,H]、[A32;Et,c-Pr,H,H,H,H]、[A33;Et,H ,c-Pr,H,H,H]、[A34;Et,OMe,H,H,H,H]、[A35;Et,H,OMe,H,H,H]、[A36; Et,OMe,H,OMe,H,H]、[A37;Et,SMe,H,H,H,H]、[A38;Et,H,SMe,H,H,H] 、[A39;Et,S(O)Me,H,H,H,H]、[A40;Et,H,S(O)Me,H,H,H]、[A41;Et,S( O)2Me,H,H,H,H]、[A42;Et,H,S(O)2Me,H,H,H]、[A43;Et,C(O)OMe,H,H ,H,H]、[A44;Et,H,C(O)OMe,H,H,H]、[A45;Et,C(O)Me,H,H,H]、[A46;Et,H,C(O)Me,H,H,H]、[A47;Et,CN,H,H,H,H]、[A48;Et,H,CN,H,H,H]、[A49;Et,NO2,H,H,H,H]、[A50;Et,H,NO2,H,H,H]、[A51;Et,NH2,H,H,H,H]、[A52;Et,H,NH2,H,H,H]、[A53;Et,NMe2,H,H,H,H]、[A54;Et,H,NMe2,H,H,H]、[A55;Et,Ph,H,H,H,H]、[A56;Et,H,Ph,H,H,H]、[A57;Et,OPh,H,H,H,H]、[A58;Et,H,OPh,H,H,H]、[A59;Et,Me,F,H,H,H]、[A60;Et,Me,H,F,H,H]、[A61;Et,Me,F,F,H,H]、[A62;Et,Me,Cl,H,H,H]、[A63;Et,Me,H,Cl,H,H]、[A64;Et,Me,Cl,Cl,H,H]、[A65;Et,Me,Br,H,H,H]、[A66;Et,Me,H,Br,H,H]、[A67;Et,Me,Br,Br,H,H]、[A68;Et,Me,I,H,H,H]、[A69;Et,Me,H,I,H,H]、[A70;Et,Me,I,I,H,H]、[A71;Et,Me,F,Me,H,H]、[A72;Et,Me,Cl,Me,H,H]、[A73;Et,Me,Br,Me,H,H]、[A74;Et,Me,I,Me,H,H]、[A75;Et,Me,Me,F,H,H]、[A76;Et,Me,Me,Cl,H,H]、[A77;Et,Me,Me,Br,H,H]、[A78;Et,Me,Me,I,H,H]、[A79;Et,F,Me,H,H,H]、[A80;Et,F,Me,F,H,H]、[A81;Et,Cl,Me,H,H,H]、[A82;Et,Cl,Me,Cl,H,H]、[A83;Et,Br,Me,H,H,H]、[A84;Et,Br,Me,Br,H,H]、[A85;Et,I,Me,H,H,H]、[A86;Et,I,Me,I,H,H]、[A87;Et,F,Cl,H,H,H]、[A88;Et,F,H,Cl,H,H]、[A89;Et,F,Cl,Cl,H,H]、[A90;Et,F,Br,H,H,H]、[A91;Et,F,H,Br,H,H]、[A92;Et,F,Br,Br,H,H]、[A93;Et,F,I,H,H,H]、[A94;Et,F,H,I,H,H]、[A95;Et,F,I,I,H,H]、[A96;Et,F,F,F,H,H]、[A97;Et,F,Cl,F,H,H]、[A98;Et,F,Br,F,H,H]、[A99;Et,F,I,F,H,H]、[A100;Et,F,F,Cl,H,H]、[A101;Et,F,F,Br,H,H]、[A102;Et,F,F,I,H,H]、[A103;Et,Cl,F,H,H,H]、[A104;Et,Cl,F,Cl,H,H]、[A105;Et,Br,F,H,H,H]、[A106;Et,Br,F,Br,H,H]、[A107;Et,I,F,H,H,H]、[A108;Et,I,F,I,H,H]、[A109;Et,Cl,Br,H,H,H]、[A110;Et,Cl,H,Br,H,H]、[A111;Et,Cl,Br,Br,H,H]、[A112;Et,Cl,I,H,H,H]、[A113;Et,Cl,H,I,H,H]、[A114;Et,Cl,I,I,H,H]、[A115;Et,Br,Cl,H,H,H]、[A116;Et,Br,Cl,Br,H,H]、[A117;Et,I,Cl,H,H,H]、[A118;Et,I,Cl,I,H,H]、[A119;Et,Cl,Cl,Br,H,H]、[A120;Et,Cl,Cl,I,H,H]、[A121;Et,Cl,Br,Cl,H,H]、[A122;Et,Cl,I,Cl,H,H]、[A123;Et,Br,I,H,H,H]、[A124;Et,Br,H,I,H,H]、[A125;Et,Br,I,I,H,H]、[A126;Et,Br,Br,I,H,H]、[A127;Et,Br,I,Br,H,H]、[A128;Et,Me,Me,H,F,H]、[A129;Et,Me,H,Me,F,H]、[A130;Et,Me,Me,Me,F,H]、[A131;Et,F,F,H,F,H]、[A132;Et,F,H,F,F,H]、[A133;Et,Cl,Cl,H,F,H]、[A134;Et,Cl,H,Cl,F,H]、[A135;Et,Br,Br,H,F,H]、[A136;Et,Br,H,Br,F,H]、[A137;Et,I,I,H,F,H]、[A138;Et,I,H,I,F,H]、[A139;Et,F,Me,F,F,H]、[A140;Et,F,F,F,F,H]、[A141;Et,F,Cl,F,F,H]、[A142;Et,F,Br,F,F,H]、[A143;Et,F,I,F,F,H]、[A144;Pr,Me,H,H,H,H]、[A145;Pr,H,Me,H,H,H]、[A146;Pr,Me,Me,H,H,H]、[A147;Pr,Me,H,Me,H,H]、[A148;Pr,Me,Me,Me,H,H]、[A149;Pr,F,H,H,H,H]、[A150;Pr,H,F,H,H,H]、[A151;Pr,F,F,H,H,H]、[A152;Pr,F,H,F,H,H]、[A153;Pr,F,F,F,H,H]、[A154;Pr,Cl,H,H,H,H]、[A155;Pr,H,Cl,H,H,H]、[A156;Pr,Cl,Cl,H,H,H]、[A157;Pr,Cl,H,Cl,H,H]、[A158;Pr,Cl,Cl,Cl,H,H]、[A159;Pr,Br,H,H,H,H]、[A160;Pr,H,Br,H,H,H]、[A161;Pr,Br,Br,H,H,H]、[A162;Pr,Br,H,Br,H,H]、[A163;Pr,Br,Br,Br,H,H]、[A164;Pr,I,H,H,H,H]、[A165;Pr,H,I,H,H,H]、[A166;Pr,I,I,H,H,H]、[A167;Pr,I,H,I,H,H]、[A168;Pr,I,I,I,H,H]、[A169;Pr,Et,H,H,H,H]、[A170;Pr,H,Et,H,H,H]、[A171;Pr,Et,H,Et,H,H]、[A172;Pr,CF3,H,H,H,H]、[A173;Pr,H,CF3,H,H,H]、[A174;Pr,CF3,H,CF3,H,H]、[A175;Pr,c-Pr,H,H,H,H]、[A176;Pr,H,c-Pr,H,H,H]、[A177;Pr,OMe,H,H,H,H]、[A178;Pr,H,OMe,H,H,H]、[A179;Pr,OMe,H,OMe,H,H]、[A180;Pr,SMe,H,H,H,H]、[A181;Pr,H,SMe,H,H,H]、[A182;Pr,S(O)Me,H,H,H,H]、[A183;Pr,H,S(O)Me,H,H,H]、[A184;Pr,S(O)2Me,H,H,H,H]、[A185;Pr,H,S(O)2Me,H,H,H]、[A186;Pr,C(O)OMe,H,H,H,H] [A187;Pr,H,C(O)OMe,H,H,H] [A188;Pr,C(O)Me,H,H,H,H] [A189;Pr,H,C(O)Me,H,H,H] [A190;Pr,CN,H,H,H,H] [A191;P r,H,CN,H,H,H] [A192;Pr,NO2,H,H,H,H] [A193;Pr,H,NO2,H,H,H] [A194;Pr,NH2,H,H,H,H] [A195;Pr,H,NH2,H,H,H] [A196;Pr,NMe2,H,H,H,H]、 [A197;Pr,H,NMe2,H,H,H]、[A198;Pr,Ph,H,H,H,H]、[A199;Pr,H,Ph,H,H,H]、[A200;Pr,OPh,H,H,H,H]、[A201;Pr,H,OPh,H,H,H]、[A202;Pr,Me,F,H, H,H] [A203;Pr,Me,H,F,H,H] [A204;Pr,Me,F,F,H,H] [A205;Pr,Me,Cl,H,H,H] [A206;Pr,Me,H,Cl,H,H] [A207;Pr,Me,Cl,Cl,H,H] [A208;Pr,Me ,Br,H,H,H] [A209;Pr,Me,H,Br,H,H] [A210;Pr,Me,Br,Br,H,H] [A211;Pr,Me,I,H,H,H] [A212;Pr,Me,H,I,H,H] [A213;Pr,Me,I,I,H,H] [A214; Pr,Me,F,Me,H,H]、[A215;Pr,Me,Cl,Me,H,H]、[A216;Pr,Me,Br,Me,H,H]、[A217;Pr,Me,I,Me,H,H]、[A218;Pr,Me,Me,F,H,H]、[A219;Pr,Me,Me,Cl,H ,H] [A220;Pr,Me,Me,Br,H,H] [A221;Pr,Me,Me,I,H,H] [A222;Pr,F,Me,H,H,H] [A223;Pr,F,Me,F,H,H] [A224;Pr,Cl,Me,H,H,H] [A225;Pr,Cl, Me,Cl,H,H] [A226;Pr,Br,Me,H,H,H] [A227;Pr,Br,Me,Br,H,H] [A228;Pr,I,Me,H,H,H] [A229;Pr,I,Me,I,H,H] [A230;Pr,F,Cl,H,H,H] [A231;Pr,F,H,Cl,H,H]、[A232;Pr,F,Cl,Cl,H,H]、[A233;Pr,F,Br,H,H,H]、[A234;Pr,F,H,Br,H,H]、[A235;Pr,F,Br,Br,H,H]、[A236;Pr,F,I,H,H,H]、[A237;Pr,F,H,I,H,H]、[A238;Pr,F,I,I,H,H]、[A239;Pr,F,F,F,H,H]、[A240;Pr,F,Cl,F,H,H]、[A241;Pr,F,Br,F,H,H]、[A242;Pr,F,I,F,H,H]、[A243;Pr,F,F,Cl,H,H]、[A244;Pr,F,F,Br,H,H]、[A245;Pr,F,F,I,H,H]、[A246;Pr,Cl,F,H,H,H]、[A247;Pr,Cl,F,Cl,H,H]、[A248;Pr,Br,F,H,H,H]、[A249;Pr,Br,F,Br,H,H]、[A250;Pr,I,F,H,H,H]、[A251;Pr,I,F,I,H,H]、[A252;Pr,Cl,Br,H,H,H]、[A253;Pr,Cl,H,Br,H,H]、[A254;Pr,Cl,Br,Br,H,H]、[A255;Pr,Cl,I,H,H,H]、[A256;Pr,Cl,H,I,H,H]、[A257;Pr,Cl,I,I,H,H]、[A258;Pr,Br,Cl,H,H,H]、[A259;Pr,Br,Cl,Br,H,H]、[A260;Pr,I,Cl,H,H,H]、[A261;Pr,I,Cl,I,H,H]、[A262;Pr,Cl,Cl,Br,H,H]、[A263;Pr,Cl,Cl,I,H,H]、[A264;Pr,Cl,Br,Cl,H,H]、[A265;Pr,Cl,I,Cl,H,H]、[A266;Pr,Br,I,H,H,H]、[A267;Pr,Br,H,I,H,H]、[A268;Pr,Br,I,I,H,H]、[A269;Pr,Br,Br,I,H,H]、[A270;Pr,Br,I,Br,H,H]、[A271;Pr,Me,Me,H,F,H]、[A272;Pr,Me,H,Me,F,H]、[A273;Pr,Me,Me,Me,F,H]、[A274;Pr,F,F,H,F,H]、[A275;Pr,F,H,F,F,H]、[A276;Pr,Cl,Cl,H,F,H]、[A277;Pr,Cl,H,Cl,F,H]、[A278;Pr,Br,Br,H,F,H]、[A279;Pr,Br,H,Br,F,H]、[A280;Pr,I,I,H,F,H]、[A281;Pr,I,H,I,F,H]、[A282;Pr,F,Me,F,F,H]、[A283;Pr,F,F,F,F,H]、[A284;Pr,F,Cl,F,F,H]、[A285;Pr,F,Br,F,F,H]、[A286;Pr,F,I,F,F,H]、[A287;CH=CH2,Me,Me,H,H,H]、[A288;CH=CH2,Me,H,Me,H,H]、[A289;CH=CH2,Me,Me,Me,H,H]、[A290;CH=CH2,F,F,H,H,H]、[A291;CH=CH2,F,H,F,H,H]、[A292;CH=CH2,Cl,Cl,H,H,H]、[A293;CH=CH2,Cl,H,Cl,H,H]、[A294;CH=CH2,Br,Br,H,H,H]、[A295;CH=CH2,Br,H,Br,H,H]、[A296;CH=CH2,I,I,H,H,H]、[A297;CH=CH2,I,H,I,H,H]、[A298;CH=CH2,F,Me,F,H,H]、[A299;CH=CH2,F,F,F,H,H]、[A300;CH=CH2,F,Cl,F,H,H]、[A301;CH=CH2,F,Br,F,H,H]、[A302;CH=CH2,F,I,F,H,H]、[A303;CH=CH2,Me,Me,H,H,H]、[A304;CH=CHCH3,Me,Me,H,H,H]、[A305;CH=CHCH3,Me,H,Me,H,H]、[A306;CH=CHCH3,Me,Me,Me,H,H]、[A307;CH=CHCH3,F,F,H,H,H]、[A308;CH=CHCH3,F,H,F,H,H]、[A309;CH=CHCH3,Cl,Cl,H,H,H]、[A310;CH=CHCH3,Cl,H,Cl,H,H]、[A311;CH=CHCH3,Br,Br,H,H,H]、[A312;CH=CHCH3,Br,H,Br,H,H]、[A313;CH=CHCH3,I,I,H,H,H]、[A314;CH=CHCH3,I,H,I,H,H]、[A315;CH=CHCH3,F,Me,F,H,H]、[A316;CH=CHCH3,F,F,F,H,H]、[A317;CH=CHCH3,F,Cl,F,H,H]、[A318;CH=CHCH3,F,Br,F,H,H]、[A319;CH=CHCH3,F,I,F,H,H]、[A320;CH=CHCH3,Me,Me,H,H,H]、[A321;CH2CH=CH2,Me,Me,H,H,H]、[A322;CH2CH=CH2,Me,H,Me,H,H]、[A323;CH2CH=CH2,Me,Me,Me,H,H]、[A324;CH2CH=CH2,F,F,H,H,H]、[A325;CH2CH=CH2,F,H,F,H,H]、[A326;CH2CH=CH2,Cl,Cl,H,H,H]、[A327;CH2CH=CH2,Cl,H,Cl,H,H]、[A328;CH2CH=CH2,Br,Br,H,H,H]、[A329;CH2CH=CH2,Br,H,Br,H,H]、[A330;CH2CH=CH2,I,I,H,H,H]、[A331;CH2CH=CH2,I,H,I,H,H]、[A332;CH2CH=CH2,F,Me,F,H,H]、[A333;CH2CH=CH2,F,F,F,H,H]、[A334;CH2CH=CH2,F,Cl,F,H,H]、[A335;CH2CH=CH2,F,Br,F,H,H]、[A336;CH2CH=CH2,F,I,F,H,H]、[A337;CH2CH=CH2,Me,Me,H,H,H]、[A338;i-Pr,Me,Me,H,H,H]、[A339;i-Pr,Me,H,Me,H,H]、[A340;i-Pr,Me,Me,Me,H,H]、[A341;i-Pr,F,F,H,H,H]、[A342;i-Pr,F,H,F,H,H]、[A343;i-Pr,Cl,Cl,H,H,H]、[A344;i-Pr,Cl,H,Cl,H,H]、[A345;i-Pr,Br,Br,H,H,H]、[A346;i-Pr,Br,H,Br,H,H]、[A347;i-Pr,I,I,H,H,H]、[A348;i-Pr,I,H,I,H,H]、[A349;i-Pr,F,Me,F,H,H]、[A350;i-Pr,F,F,F,H,H]、[A351;i-Pr,F,Cl,F,H,H]、[A352;i-Pr,F,Br,F,H,H]、[A353;i-Pr,F,I,F,H,H]、[A354;i-Pr,Me,Me,H,H,H]、[A355;Bu,Me,Me,H,H,H]、[A356;Bu,Me,H,Me,H,H]、[A357;Bu,Me,Me,Me,H,H]、[A358;Bu,F,F,H,H,H]、[A359;Bu,F,H,F,H,H]、[A360;Bu,Cl,Cl,H,H,H]、[A361;Bu,Cl,H,Cl,H,H]、[A362;Bu,Br,Br,H,H,H]、[A363;Bu,Br,H,Br,H,H]、[A364;Bu,I,I,H,H,H]、[A365;Bu,I,H,I,H,H]、[A366;Bu,F,Me,F,H,H]、[A367;Bu,F,F,F,H,H]、[A368;Bu,F,Cl,F,H,H]、[A369;Bu,F,Br,F,H,H]、[A370;Bu,F,I,F,H,H]、[A371;Bu,Me,Me,H,H,H]、[A372;i-Bu,Me,Me,H,H,H]、[A373;i-Bu,Me,H,Me,H,H]、[A374;i-Bu,Me,Me,Me,H,H]、[A375;i-Bu,F,F,H,H,H]、[A376;i-Bu,F,H,F,H,H]、[A377;i-Bu,Cl,Cl,H,H,H]、[A378;i-Bu,Cl,H,Cl,H,H]、[A379;i-Bu,Br,Br,H,H,H]、[A380;i-Bu,Br,H,Br,H,H]、[A381;i-Bu,I,I,H,H,H]、[A382;i-Bu,I,H,I,H,H]、[A383;i-Bu,F,Me,F,H,H]、[A384;i-Bu,F,F,F,H,H]、[A385;i-Bu,F,Cl,F,H,H]、[A386;i-Bu,F,Br,F,H,H]、[A387;i-Bu,F,I,F,H,H]、[A388;i-Bu,Me,Me,H,H,H]、[A389;s-Bu,Me,Me,H,H,H]、[A390;s-Bu,Me,H,Me,H,H]、[A391;s-Bu,Me,Me,Me,H,H]、[A392;s-Bu,F,F,H,H,H]、[A393;s-Bu,F,H,F,H,H]、[A394;s-Bu,Cl,Cl,H,H,H]、[A395;s-Bu,Cl,H,Cl,H,H]、[A396;s-Bu,Br,Br,H,H,H]、[A397;s-Bu,Br,H,Br,H,H]、[A398;s-Bu,I,I,H,H,H]、[A399;s-Bu,I,H,I,H,H]、[A400;s-Bu,F,Me,F,H,H]、[A401;s-Bu,F,F,F,H,H]、[A402;s-Bu,F,Cl,F,H,H]、[A403;s-Bu,F,Br,F,H,H]、[A404;s-Bu,F,I,F,H,H]、[A405;s-Bu,Me,Me,H,H,H]、[A406;c-Pr,Me,Me,H,H,H]、[A407;c-Pr,Me,H,Me,H,H]、[A408;c-Pr,Me,Me,Me,H,H]、[A409;c-Pr,F,F,H,H,H]、[A410;c-Pr,F,H,F,H,H]、[A411;c-Pr,Cl,Cl,H,H,H]、[A412;c-Pr,Cl,H,Cl,H,H]、[A413;c-Pr,Br,Br,H,H,H]、[A414;c-Pr,Br,H,Br,H,H]、[A415;c-Pr,I,I,H,H,H]、[A416;c-Pr,I,H,I,H,H]、[A417;c-Pr,F,Me,F,H,H]、[A418;c-Pr,F,F,F,H,H]、[A419;c-Pr,F,Cl,F,H,H]、[A420;c-Pr,F,Br,F,H,H]、[A421;c-Pr,F,I,F,H,H]、[A422;c-Pr,Me,Me,H,H,H]、[A423;CH2(c-Pr),Me,Me,H,H,H]、[A424;CH2(c-Pr),Me,H,Me,H,H]、[A425;CH2(c-Pr),Me,Me,Me,H,H]、[A426;CH2(c-Pr),F,F,H,H,H]、[A427;CH2(c-Pr),F,H,F,H,H]、[A428;CH2(c-Pr),Cl,Cl,H,H,H]、[A429;CH2(c-Pr),Cl,H,Cl,H,H]、[A430;CH2(c-Pr),Br,Br,H,H,H]、[A431;CH2(c-Pr),Br,H,Br,H,H]、[A432;CH2(c-Pr),I,I,H,H,H]、[A433;CH2(c-Pr),I,H,I,H,H]、[A434;CH2(c-Pr),F,Me,F,H,H]、[A435;CH2(c-Pr),F,F,F,H,H]、[A436;CH2(c-Pr),F,Cl,F,H,H]、 [A437;CH2(c-Pr),F,Br,F,H,H]、[A438;CH2(c-Pr),F,I,F,H,H]、[A439;CH2(c-Pr),Me,Me,H,H,H]、[A440;Bn,Me,Me,H,H,H]、[A441;Bn,Me,H,Me,H,H]、[A442;Bn,Me,Me,Me,H,H]、[A443;Bn,F,F,H,H,H]、[A444;Bn,F,H,F,H,H]、[A445;Bn,Cl,Cl,H,H,H]、[A446;Bn,Cl,H,Cl,H,H]、[A447;Bn,Br,Br,H,H,H]、[A448;Bn,Br,H,Br,H,H]、[A449;Bn,I,I,H,H,H]、[A450;Bn,I,H,I,H,H]、[A451;Bn,F,Me,F,H,H]、[A452;Bn,F,F,F,H,H]、[A453;Bn,F,Cl,F,H,H]、[A454;Bn,F,Br,F,H,H]、[A455;Bn,F,I,F,H,H]、[A456;Bn,Me,Me,H,H,H]、[A457;Ph,Me,Me,H,H,H]、[A458;Ph,Me,H,Me,H,H]、[A459;Ph,Me,Me,Me,H,H]、[A460;Ph,F,F,H,H,H]、[A461;Ph,F,H,F,H,H]、[A462;Ph,Cl,Cl,H,H,H]、[A463;Ph,Cl,H,Cl,H,H]、[A464;Ph,Br,Br,H,H,H]、[A465;Ph,Br,H,Br,H,H]、[A466;Ph,I,I,H,H,H]、[A467;Ph,I,H,I,H,H]、[A468;Ph,F,Me,F,H,H]、[A469;Ph,F,F,F,H,H]、[A470;Ph,F,Cl,F,H,H]、[A471;Ph,F,Br,F,H,H]、[A472;Ph,F,I,F,H,H]、[A473;Ph,Me,Me,H,H,H]、[A474;2-Py,Me,Me,H,H,H]、[A475;2-Py,Me,H,Me,H,H]、[A476;2-Py,Me,Me,Me,H,H]、[A477;2-Py,F,F,H,H,H]、[A478;2-Py,F,H,F,H,H]、[A479;2-Py,Cl,Cl,H,H,H]、[A480;2-Py,Cl,H,Cl,H,H]、[A481;2-Py,Br,Br,H,H,H]、[A482;2-Py,Br,H,Br,H,H]、[A483;2-Py,I,I,H,H,H]、[A484;2-Py,I,H,I,H,H]、[A485;2-Py,F,Me,F,H,H]、[A486;2-Py,F,F,F,H,H]、[A487;2-Py,F,Cl,F,H,H]、[A488;2-Py,F,Br,F,H,H]、[A489;2-Py,F,I,F,H,H]、[A490;2-Py,Me,Me,H,H,H]、[A491;3-Py,Me,Me,H,H,H]、[A492;3-Py,Me,H,Me,H,H]、[A493;3-Py,Me,Me,Me,H,H]、[A494;3-Py,F,F,H,H,H]、[A495;3-Py,F,H,F,H,H]、[A496;3-Py,Cl,Cl,H,H,H]、[A497;3-Py,Cl,H,Cl,H,H]、[A498;3-Py,Br,Br,H,H,H]、[A499;3-Py,Br,H,Br,H,H]、[A500;3-Py,I,I,H,H,H]、[A501;3-Py,I,H,I,H,H]、[A502;3-Py,F,Me,F,H,H]、[A503;3-Py,F,F,F,H,H]、[A504;3-Py,F,Cl,F,H,H]、[A505;3-Py,F,Br,F,H,H]、[A506;3-Py,F,I,F,H,H]、[A507;3-Py,Me,Me,H,H,H]、[A508;4-Py,Me,Me,H,H,H]、[A509;4-Py,Me,H,Me,H,H]、[A510;4-Py,Me,Me,Me,H,H]、[A511;4-Py,F,F,H,H,H]、[A512;4-Py,F,H,F,H,H]、[A513;4-Py,Cl,Cl,H,H,H]、[A514;4-Py,Cl,H,Cl,H,H]、[A515;4-Py,Br,Br,H,H,H]、[A516;4-Py,Br,H,Br,H,H]、[A517;4-Py,I,I,H,H,H]、[A518;4-Py,I,H,I,H,H]、[A519;4-Py,F,Me,F,H,H]、[A520;4-Py,F,F,F,H,H]、[A521;4-Py,F,Cl,F,H,H]、[A522;4-Py,F,Br,F,H,H]、[A523;4-Py,F,I,F,H,H]、[A524;4-Py,Me,Me,H,H,H]、[A525;2-Pyrimidyl,Me,Me,H,H,H]、[A526;2-Pyrimidyl,Me,H,Me,H,H]、[A527;2-Pyrimidyl,Me,Me,Me,H,H]、[A528;2-Pyrimidyl,F,F,H,H,H]、[A529;2-Pyrimidyl,F,H,F,H,H]、[A530;2-Pyrimidyl,Cl,Cl,H,H,H]、[A531;2-Pyrimidyl,Cl,H,Cl,H,H]、[A532;2-Pyrimidyl,Br,Br,H,H,H]、[A533;2-Pyrimidyl,Br,H,Br,H,H]、[A534;2-Pyrimidyl,I,I,H,H,H]、[A535;2-Pyrimidyl,I,H,I,H,H]、[A536;2-Pyrimidyl,F,Me,F,H,H]、[A537;2-Pyrimidyl,F,F,F,H,H]、[A538;2-Pyrimidyl,F,Cl,F,H,H]、[A539;2-Pyrimidyl,F,Br,F,H,H]、[A540;2-Pyrimidyl,F,I,F,H,H]、[A541;2-Pyrimidyl,Me,Me,H,H,H]、[A542;4-Pyrimidyl,Me,Me,H,H,H]、[A543;4-Pyrimidyl,Me,H,Me,H,H]、[A544;4-Pyrimidyl,Me,Me,Me,H,H]、[A545;4-Pyrimidyl,F,F,H,H,H]、[A546;4-Pyrimidyl,F,H,F,H,H]、[A547;4-Pyrimidyl,Cl,Cl,H,H,H]、[A548;4-Pyrimidyl,Cl,H,Cl,H,H]、[A549;4-Pyrimidyl,Br,Br,H,H,H]、[A550;4-Pyrimidyl,Br,H,Br,H,H]、[A551;4-Pyrimidyl,I,I,H,H,H]、[A552;4-Pyrimidyl,I,H,I,H,H]、[A553;4-Pyrimidyl,F,Me,F,H,H]、[A554;4-Pyrimidyl,F,F,F,H,H]、[A555;4-Pyrimidyl,F,Cl,F,H,H]、[A556;4-Pyrimidyl,F,Br,F,H,H]、[A557;4-Pyrimidyl,F,I,F,H,H]、[A558;4-Pyrimidyl,Me,Me,H,H,H]、[A559;2-Pyradinyl,Me,Me,H,H,H]、[A560;2-Pyradinyl,Me,H,Me,H,H]、[A561;2-Pyradinyl,Me,Me,Me,H,H]、[A562;2-Pyradinyl,F,F,H,H,H]、[A563;2-Pyradinyl,F,H,F,H,H]、[A564;2-Pyradinyl,Cl,Cl,H,H,H]、[A565;2-Pyradinyl,Cl,H,Cl,H,H]、[A566;2-Pyradinyl,Br,Br,H,H,H]、[A567;2-Pyradinyl,Br,H,Br,H,H]、[A568;2-Pyradinyl,I,I,H,H,H]、[A569;2-Pyradinyl,I,H,I,H,H]、[A570;2-Pyradinyl,F,Me,F,H,H]、[A571;2-Pyradinyl,F,F,F,H,H]、[A572;2-Pyradinyl,F,Cl,F,H,H]、[A573;2-Pyradinyl,F,Br,F,H,H]、[A574;2-Pyradinyl,F,I,F,H,H]、[A575;2-Pyradinyl,Me,Me,H,H,H]、[A576;2-furyl,Me,Me,H,H,H]、[A577;2-furyl,Me,H,Me,H,H]、[A578;2-furyl,Me,Me,Me,H,H]、[A579;2-furyl,F,F,H,H,H]、[A580;2-furyl,F,H,F,H,H]、[A581;2-furyl,Cl,Cl,H,H,H]、[A582;2-furyl,Cl,H,Cl,H,H]、[A583;2-furyl,Br,Br,H,H,H]、[A584;2-furyl,Br,H,Br,H,H]、[A585;2-furyl,I,I,H,H,H]、[A586;2-furyl,I,H,I,H,H]、[A587;2-furyl,F,Me,F,H,H]、[A588;2-furyl,F,F,F,H,H]、[A589;2-furyl,F,Cl,F,H,H]、[A590;2-furyl,F,Br,F,H,H]、[A591;2-furyl,F,I,F,H,H]、[A592;2-furyl,Me,Me,H,H,H]、[A593;3-furyl,Me,Me,H,H,H]、[A594;3-furyl,Me,H,Me,H,H]、[A595;3-furyl,Me,Me,Me,H,H]、[A596;3-furyl,F,F,H,H,H]、[A597;3-furyl,F,H,F,H,H]、[A598;3-furyl,Cl,Cl,H,H,H]、[A599;3-furyl,Cl,H,Cl,H,H]、[A600;3-furyl,Br,Br,H,H,H]、[A601;3-furyl,Br,H,Br,H,H]、[A602;3-furyl,I,I,H,H,H]、[A603;3-furyl,I,H,I,H,H]、[A604;3-furyl,F,Me,F,H,H]、[A605;3-furyl,F,F,F,H,H]、[A606;3-furyl,F,Cl,F,H,H]、[A607;3-furyl,F,Br,F,H,H]、[A608;3-furyl,F,I,F,H,H]、[A609;3-furyl,Me,Me,H,H,H]、[A610;2-thienyl,Me,Me,H,H,H]、[A611;2-thienyl,Me,H,Me,H,H]、[A612;2-thienyl,Me,Me,Me,H,H]、[A613;2-thienyl,F,F,H,H,H]、[A614;2-thienyl,F,H,F,H,H]、[A615;2-thienyl,Cl,Cl,H,H,H]、[A616;2-thienyl,Cl,H,Cl,H,H]、[A617;2-thienyl,Br,Br,H,H,H]、[A618;2-thienyl,Br,H,Br,H,H]、[A619;2-thienyl,I,I,H,H,H]、[A620;2-thienyl,I,H,I,H,H]、[A621;2-thienyl,F,Me,F,H,H]、[A622;2-thienyl,F,F,F,H,H]、[A623;2-thienyl,F,Cl,F,H,H]、[A624;2-thienyl,F,Br,F,H,H]、[A625;2-thienyl,F,I,F,H,H]、[A626;2-thienyl,Me,Me,H,H,H]、[A627;3-thienyl,Me,Me,H,H,H]、[A628;3-thienyl,Me,H,Me,H,H]、[A629;3-thienyl,Me,Me,Me,H,H]、[A630;3-thienyl,F,F,H,H,H]、[A631;3-thienyl,F,H,F,H,H]、[A632;3-thienyl,Cl,Cl,H,H,H]、[A633;3-thienyl,Cl,H,Cl,H,H]、 [A634;3-thienyl,Br,Br,H,H,H]、[A635;3-thienyl,Br,H,Br,H,H]、[A636;3-thienyl,I,I,H,H,H]、[A637;3-thienyl,I,H,I,H,H]、[A638;3-thienyl,F,Me,F,H,H]、[A639;3-thienyl,F,F,F,H,H]、[A640;3-thienyl,F,Cl,F,H,H]、[A641;3-thienyl,F,Br,F,H,H]、[A642;3-thienyl,F,I,F,H,H]、[A643;3-thienyl,Me,Me,H,H,H]、[A644;NMe2,Me,Me,H,H,H]、[A645;NMe2,Me,H,Me,H,H]、[A646;NMe2,Me,Me,Me,H,H]、[A647;NMe2,F,F,H,H,H]、[A648;NMe2,F,H,F,H,H]、[A649;NMe2,Cl,Cl,H,H,H]、[A650;NMe2,Cl,H,Cl,H,H]、[A651;NMe2,Br,Br,H,H,H]、[A652;NMe2,Br,H,Br,H,H]、[A653;NMe2,I,I,H,H,H]、[A654;NMe2,I,H,I,H,H]、[A655;NMe2,F,Me,F,H,H]、[A656;NMe2,F,F,F,H,H]、[A657;NMe2,F,Cl,F,H,H]、[A658;NMe2,F,Br,F,H,H]、[A659;NMe2,F,I,F,H,H]、[A660;NMe2,Me,Me,H,H,H].;
[0087] Compounds represented by formula (A-1), in which n is 1, R2A, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX2). Compounds represented by formula (A-1), in which n is 2, R2A, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX3). Compounds represented by formula (A-1), in which n is 0, R2A is a methyl group, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX4). Compounds represented by formula (A-1), wherein n is 1, R2A is a methyl group, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX5). Compounds represented by formula (A-1), wherein n is 2, R2A is a methyl group, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX6). Compounds represented by formula (A-1), wherein n is 0, R2B is a methyl group, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX7). Compounds represented by formula (A-1), wherein n is 1, R2B is a methyl group, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX8).Compounds represented by formula (A-1), wherein n is 2, R2B is a methyl group, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX9). Compounds represented by formula (A-1), wherein n is 0, R2C is a methyl group, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX10). Compounds represented by formula (A-1), in which n is 1, R2C is a methyl group, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX11). Compounds represented by formula (A-1), in which n is 2, R2C is a methyl group, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX12). Compounds represented by formula (A-1), in which n is 0, R2D is a methyl group, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as compound group SX13). Compounds represented by formula (A-1), in which n is 1, R2D is a methyl group, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as compound group SX14). Compounds represented by formula (A-1), in which n is 2, R2D is a methyl group, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in combination A (hereinafter referred to as compound group SX15).Compounds represented by formula (A-1), wherein n is 0, R2A is a chlorine atom, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in Combination A (hereinafter referred to as compound group SX16). Compounds represented by formula (A-1), wherein n is 1, R2A is a chlorine atom, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in Combination A (hereinafter referred to as compound group SX17). Compounds represented by formula (A-1), wherein n is 2, R2A is a chlorine atom, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in Combination A (hereinafter referred to as compound group SX18). Compounds represented by formula (A-1), wherein n is 0, R2B is a chlorine atom, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in Combination A (hereinafter referred to as compound group SX19). Compounds represented by formula (A-1), wherein n is 1, R2B is a chlorine atom, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX20). Compounds represented by formula (A-1), wherein n is 2, R2B is a chlorine atom, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX21). Compounds represented by formula (A-1), in which n is 0, R2C is a chlorine atom, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in combination A (hereinafter, referred to as compound group SX22).Compounds represented by formula (A-1), wherein n is 1, R2C is a chlorine atom, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as compound group SX23). Compounds represented by formula (A-1), wherein n is 2, R2C is a chlorine atom, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any of the combinations described in Combination A (hereinafter referred to as compound group SX24). Compounds represented by formula (A-1), in which n is 0, R2D is a chlorine atom, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in Combination A (hereinafter referred to as Compound Group SX25). Compounds represented by formula (A-1), in which n is 1, R2D is a chlorine atom, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in Combination A (hereinafter referred to as Compound Group SX26). Compounds represented by formula (A-1), in which n is 2, R2D is a chlorine atom, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, R3A, R3B, R3C, R4, and R5 is any combination described in combination A (hereinafter, referred to as compound group SX27).
[0088] Formula (B-1) In the compounds represented by the formula (1), n is 0, R, R, R, and R are each a hydrogen atom, and the combination of R, D, D, and D is any of the combinations described in combination B (hereinafter referred to as compound group SX28).
[0089] Combination B consists of substituent numbers B1 to B192. Substituent numbers B1 to B192 represent combinations of R1, D1, D2, and D3 in the compound represented by formula (B-1), and are hereinafter referred to as [substituent numbers: R1, D1, D2, D3]. For example, substituent number B5 represents a combination in which R1 is an ethyl group, D1 is C(CH3)2, and D2 and D3 are CH2.
[0090] Combination B [Substituent numbers; R1, D1, D2, D3]: [B1; Et, CH2, CH2, CH2], [B2; Et, O, CH2, O], [B3; Et, O, CF2, O], [B4; Et, CH2, O, CH2], [B5; Et, C(CH3)2, CH2, CH2], [B6; Et, CH2, CH2, C(CH3)2], [B7; Et, C(CH3)2, CH2, CH(CH3)], [B8; Et, CH(CH3), CH2, C(CH3)2], [B9; CH=CH2, CH2, CH2, CH2], [B10; CH=CH2, O, CH2, O], [B11; CH=CH2, O, CF2, O], [B12; CH=CH2, CH2, O, CH2], [B13; CH=CH2, C(CH3)2, CH2, CH2], [B14; CH=CH2, CH2, CH2, C(CH3)2], [B15; CH=CH2, C(CH3)2, CH2, CH(CH3)], [B16; CH=CH2, CH(CH3), CH2, C(CH3)2], [B17; Pr, CH2, CH2, CH2], [B18; Pr, O, CH2, O], [B19; Pr, O, CF2, O], [B20; Pr, CH2, O, CH2], [B21; Pr, C(CH3)2, CH2, CH2], [B22; Pr, CH2, CH2, C(CH3)2], [B23; Pr, C(CH3)2, CH2, CH(CH3)], [B24; Pr, CH(CH3), CH2, C(CH3)2], [B25; CH=CHCH3, CH2, CH2, CH2], [B26; CH=CHCH3, O, CH2, O], [B27; CH=CHCH3, O, CF2, O], [B28; CH=CHCH3, CH2, O, CH2], [B29; CH=CHCH3, C(CH3)2, CH2, CH2], [B30; CH=CHCH3, CH2, CH2, C(CH3)2], [B31; CH=CHCH3, C(CH3)2, CH2, CH(CH3)], [B32; CH=CHCH3, CH(CH3), CH2, C(CH3)2], [B33; CH2CH=CH2, CH2, CH2, CH2], [B34; CH2CH=CH2, O, CH2, O], [B35; CH2CH=CH2, O, CF2, O], [B36; CH2CH=CH2, CH2, O, CH2], [B37; CH2CH=CH2, C(CH3)2, CH2, CH2], [B38; CH2CH=CH2, CH2, CH2, C(CH3)2], [B39;CH2CH=CH2,C(CH3)2,CH2,CH(CH3)]、[B40;CH2CH=CH2,CH(CH3),CH2,C(CH3)2]、[B41;i-Pr,CH2,CH2,CH2]、[B42;i-Pr,O,CH2,O]、[B43;i-Pr,O,CF 2,O]、[B44;i-Pr,CH2,O,CH2]、[B45;i-Pr,C(CH3)2,CH2,CH2]、[B46;i-P r,CH2,CH2,C(CH3)2]、[B47;i-Pr,C(CH3)2,CH2,CH(CH3)]、[B48;i-Pr,CH (CH3),CH2,C(CH3)2]、[B49;Bu,CH2,CH2,CH2]、[B50;Bu,O,CH2,O]、[B51;Bu,O,CF2,O]、[B52;Bu,CH2,O,CH2]、[B53;Bu,C(CH3)2,CH2,CH2]、[B54; Bu,CH2,CH2,C(CH3)2]、[B55;Bu,C(CH3)2,CH2,CH(CH3)]、[B56;Bu,CH(CH3),CH2,C(CH3)2]、[B57;i-Bu,CH2,CH2,CH2]、[B58;i-Bu,O,CH2,O]、[B5 9;i-Bu,O,CF2,O]、[B60;i-Bu,CH2,O,CH2]、[B61;i-Bu,C(CH3)2,CH2,CH2]、[B62;i-Bu,CH2,CH2,C(CH3)2]、[B63;i-Bu,C(CH3)2,CH2,CH(CH3)]、[B64;i-Bu,CH(CH3),CH2,C(CH3)2]、[B65;s-Bu,CH2,CH2,CH2]、[B66;s-Bu,O,CH2,O]、[B67;s-Bu,O,CF2,O]、[B68;s-Bu,CH2,O,CH2]、[B69;s-Bu,C (CH3)2,CH2,CH2]、[B70;s-Bu,CH2,CH2,C(CH3)2]、[B71;s-Bu,C(CH3)2,CH2,CH(CH3)]、[B72;s-Bu,CH(CH3),CH2,C(CH3)2]、[B73;c-Pr,CH2,CH2, CH2]、[B74;c-Pr,O,CH2,O]、[B75;c-Pr,O,CF2,O]、[B76;c-Pr,CH2,O,CH 2]、[B77;c-Pr,C(CH3)2,CH2,CH2]、[B78;c-Pr,CH2,CH2,C(CH3)2]、[B79;c-Pr,C(CH3)2,CH2,CH(CH3)]、[B80;c-Pr,CH(CH3),CH2,C(CH3)2]、[B81;CH2(c-Pr),CH2,CH2,CH2]、[B82;CH2(c-Pr),O,CH2,O]、[B83;CH2(c-Pr),O,CF2,O]、[B84;CH2(c-Pr),CH2,O,CH2]、[B85;CH2(c-Pr),C(CH3)2,CH2,CH2]、[B86;CH2(c-Pr),CH2,CH2,C(CH3)2]、[B87;CH2(c-Pr),C(CH3)2,CH2,CH(CH3)]、[B88;CH2(c-Pr),CH(CH3),CH2,C(CH3)2]、[B89;Bn,CH2,CH2,CH2]、[B90;Bn,O,CH2,O]、[B91;Bn,O,CF2,O]、[B92;Bn,CH2,O,CH2]、[B93;Bn,C(CH3)2,CH2,CH2]、[B94;Bn,CH2,CH2,C(CH3)2]、[B95;Bn,C(CH3)2,CH2,CH(CH3)]、[B96;Bn,CH(CH3),CH2,C(CH3)2]、[B97;Ph,CH2,CH2,CH2]、[B98;Ph,O,CH2,O]、[B99;Ph,O,CF2,O]、[B100;Ph,CH2,O,CH2]、[B101;Ph,C(CH3)2,CH2,CH2]、[B102;Ph,CH2,CH2,C(CH3)2]、[B103;Ph,C(CH3)2,CH2,CH(CH3)]、[B104;Ph,CH(CH3),CH2,C(CH3)2]、[B105;2-Py,CH2,CH2,CH2]、[B106;2-Py,O,CH2,O]、[B107;2-Py,O,CF2,O]、[B108;2-Py,CH2,O,CH2]、[B109;2-Py,C(CH3)2,CH2,CH2]、[B110;2-Py,CH2,CH2,C(CH3)2]、[B111;2-Py,C(CH3)2,CH2,CH(CH3)]、[B112;2-Py,CH(CH3),CH2,C(CH3)2]、[B113;3-Py,CH2,CH2,CH2]、[B114;3-Py,O,CH2,O]、[B115;3-Py,O,CF2,O]、[B116;3-Py,CH2,O,CH2]、[B117;3-Py,C(CH3)2,CH2,CH2]、[B118;3-Py,CH2,CH2,C(CH3)2]、[B119;3-Py,C(CH3)2,CH2,CH(CH3)]、[B120;3-Py,CH(CH3),CH2,C(CH3)2]、[B121;4-Py,CH2,CH2,CH2]、[B122;4-Py,O,CH2,O]、[B123;4-Py,O,CF2,O]、[B124;4-Py,CH2,O,CH2]、[B125;4-Py,C(CH3)2,CH2,CH2]、[B126;4-Py,CH2,CH2,C(CH3)2]、[B127;4-Py,C(CH3)2,CH2,CH(CH3)]、[B128;4-Py,CH(CH3),CH2,C(CH3)2]、[B129;2-Pyrimidyl,CH2,CH2,CH2]、[B130;2-Pyrimidyl,O,CH2,O]、[B131;2-Pyrimidyl,O,CF2,O]、[B132;2-Pyrimidyl,CH2,O,CH2]、[B133;2-Pyrimidyl,C(CH3)2,CH2,CH2]、[B134;2-Pyrimidyl,CH2,CH2,C(CH3)2]、[B135;2-Pyrimidyl,C(CH3)2,CH2,CH(CH3)]、[B136;2-Pyrimidyl,CH(CH3),CH2,C(CH3)2]、[B137;4-Pyrimidyl,CH2,CH2,CH2]、[B138;4-Pyrimidyl,O,CH2,O]、[B139;4-Pyrimidyl,O,CF2,O]、[B140;4-Pyrimidyl,CH2,O,CH2]、[B141;4-Pyrimidyl,C(CH3)2,CH2,CH2]、[B142;4-Pyrimidyl,CH2,CH2,C(CH3)2]、[B143;4-Pyrimidyl,C(CH3)2,CH2,CH(CH3)]、[B144;4-Pyrimidyl,CH(CH3),CH2,C(CH3)2]、[B145;2-Pyradinyl,CH2,CH2,CH2]、[B146;2-Pyradinyl,O,CH2,O]、[B147;2-Pyradinyl,O,CF2,O]、[B148;2-Pyradinyl,CH2,O,CH2]、[B149;2-Pyradinyl,C(CH3)2,CH2,CH2]、[B150;2-Pyradinyl,CH2,CH2,C(CH3)2]、[B151;2-Pyradinyl,C(CH3)2,CH2,CH(CH3)]、[B152;2-Pyradinyl,CH(CH3),CH2,C(CH3)2]、[B153;2-furyl,CH2,CH2,CH2]、[B154;2-furyl,O,CH2,O]、[B155;2-furyl,O,CF2,O]、[B156;2-furyl,CH2,O,CH2]、[B157;2-furyl,C(CH3)2,CH2,CH2]、[B158;2-furyl,CH2,CH2,C(CH3)2]、[B159;2-furyl,C(CH3)2,CH2,CH(CH3)]、[B160;2-furyl,CH(CH3),CH2,C(CH3)2]、[B161;3-furyl,CH2,CH2,CH2]、[B162;3-furyl,O,CH2,O]、[B163;3-furyl,O,CF2,O]、[B164;3-furyl,CH2,O,CH2]、[B165;3-furyl,C(CH3)2,CH2,CH2]、[B166;3-furyl,CH2,CH2,C(CH3)2]、[B167;3-furyl,C(CH3)2,CH2,CH(CH3)]、[B168;3-furyl,CH(CH3),CH2,C(CH3)2]、[B169;2-thienyl,CH2,CH2,CH2]、[B170;2-thienyl,O,CH2,O]、[B171;2-thienyl,O,CF2,O]、[B172;2-thienyl,CH2,O,CH2]、[B173;2-thienyl,C(CH3)2,CH2,CH2]、[B174;2-thienyl,CH2,CH2,C(CH3)2]、[B175;2-thienyl,C(CH3)2,CH2,CH(CH3)]、[B176;2-thienyl,CH(CH3),CH2,C(CH3)2]、[B177;3-thienyl,CH2,CH2,CH2]、[B178;3-thienyl,O,CH2,O]、[B179;3-thienyl,O,CF2,O]、[B180;3-thienyl,CH2,O,CH2]、[B181;3-thienyl,C(CH3)2,CH2,CH2]、[B182;3-thienyl,CH2,CH2,C(CH3)2]、[B183;3-thienyl,C(CH3)2,CH2,CH(CH3)]、[B184;3-thienyl,CH(CH3),CH2,C(CH3)2]、[B185;NMe2,CH2,CH2,CH2]、[B186;NMe2,O,CH2,O]、[B187;NMe2,O,CF2,O]、[B188;NMe2,CH2,O,CH2]、[B189;NMe2,C(CH3)2,CH2,CH2]、[B190;NMe2,CH2,CH2,C(CH3)2]、[B191;NMe2,C(CH3)2,CH2,CH(CH3)]、[B192;NMe2,CH(CH3),CH2,C(CH3)2].;
[0091] Compounds represented by formula (B-1), in which n is 1, R2A, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any one of the combinations described in Combination B (hereinafter referred to as Compound Group SX29). Compounds represented by formula (B-1), in which n is 2, R2A, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any one of the combinations described in Combination B (hereinafter referred to as Compound Group SX30). Compounds represented by formula (B-1), in which n is 0, R2A is a methyl group, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any one of the combinations described in Combination B (hereinafter referred to as Compound Group SX31). Compounds represented by formula (B-1), wherein n is 1, R2A is a methyl group, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX32). Compounds represented by formula (B-1), wherein n is 2, R2A is a methyl group, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX33). Compounds represented by formula (B-1), wherein n is 0, R2B is a methyl group, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX34). Compounds represented by formula (B-1), wherein n is 1, R2B is a methyl group, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX35). Compounds represented by formula (B-1), wherein n is 2, R2B is a methyl group, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX36).Compounds represented by formula (B-1), wherein n is 0, R2C is a methyl group, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX37). Compounds represented by formula (B-1), wherein n is 1, R2C is a methyl group, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX38). Compounds represented by formula (B-1), wherein n is 2, R2C is a methyl group, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX39). Compounds represented by formula (B-1), wherein n is 0, R2D is a methyl group, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX40). Compounds represented by formula (B-1), wherein n is 1, R2D is a methyl group, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX41). Compounds represented by formula (B-1), wherein n is 2, R2D is a methyl group, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX42). Compounds represented by formula (B-1), wherein n is 0, R2A is a chlorine atom, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as compound group SX43). Compounds represented by formula (B-1), wherein n is 1, R2A is a chlorine atom, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as compound group SX44).Compounds represented by formula (B-1), wherein n is 2, R2A is a chlorine atom, R2B, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX45). Compounds represented by formula (B-1), wherein n is 0, R2B is a chlorine atom, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX46). Compounds represented by formula (B-1), wherein n is 1, R2B is a chlorine atom, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX47). Compounds represented by formula (B-1), wherein n is 2, R2B is a chlorine atom, R2A, R2C, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any one of the combinations described in Combination B (hereinafter referred to as Compound Group SX48). Compounds represented by formula (B-1), wherein n is 0, R2C is a chlorine atom, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any one of the combinations described in Combination B (hereinafter referred to as Compound Group SX49). Compounds represented by formula (B-1), wherein n is 1, R2C is a chlorine atom, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any one of the combinations described in Combination B (hereinafter referred to as Compound Group SX50). Compounds represented by formula (B-1), wherein n is 2, R2C is a chlorine atom, R2A, R2B, and R2D are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX51). Compounds represented by formula (B-1), wherein n is 0, R2D is a chlorine atom, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as Compound Group SX52).Compounds represented by formula (B-1), wherein n is 1, R2D is a chlorine atom, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as compound group SX53). Compounds represented by formula (B-1), wherein n is 2, R2D is a chlorine atom, R2A, R2B, and R2C are each a hydrogen atom, and the combination of R1, D1, D2, and D3 is any of the combinations described in Combination B (hereinafter referred to as compound group SX54).
[0092] Formulation examples are shown below. Note that "parts" refers to parts by weight. Compound S represents a compound described in compound group SX1 to SX54.
[0093] Formulation Example 1 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the present compounds S, and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain a formulation.
[0094] Formulation Example 2 50 parts of any one of the present compounds S, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica are ground and mixed to obtain a formulation.
[0095] Formulation Example 3: A formulation is obtained by mixing 5 parts of any one of the present compounds S, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide added: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.
[0096] Formulation Example 4: 2 parts of any one of the present compounds S, 1 part of silica, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, and an appropriate amount of water is added and kneaded. The mixture is granulated in a granulator and then dried to obtain a formulation.
[0097] Formulation Example 5 10 parts of any one of the present compounds S is mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ, and 54 parts of solvent naphtha are added thereto and mixed to obtain a formulation.
[0098] Next, test examples are shown. The untreated group in Test Examples 3, 5, and 6 refers to a test group conducted under the same conditions as those described in each test example, except that DMSO was dispensed instead of the DMSO diluted solution containing the present compound. The untreated group in Test Examples 7 and 15 refers to a test conducted under the same conditions as those described in each test example, except that DMSO was dispensed instead of the DMSO diluted solution containing the present compound. Furthermore, the untreated group in Test Examples 8, 9, 10, and 11 refers to a test in which a water dilution of a formulation containing the present compound was not sprayed.
[0099] Test Example 1: Control test against wheat leaf blight fungus (Septoria tritici) The present compound was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), followed by 150 μL of YBG medium inoculated with spores of the wheat leaf blight fungus. The plate was incubated at 18°C for 3 days to allow the wheat leaf blight fungus to grow, after which the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of the wheat leaf blight fungus. As a result, each of the present compounds demonstrated plant disease control effects.
[0100] Test Example 2: Control test against Ustilago maydis (corn smut fungus). The present compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of Ustilago maydis was dispensed. The plate was incubated at 18°C for 4 days to allow the corn smut fungus to grow. The absorbance at 550 nm of each well of the titer plate was then measured, and this value was used as the growth rate of Ustilago maydis. As a result, each of the present compounds demonstrated plant disease control effects.
[0101] Test Example 3: Control test against barley scald fungus (Rhynchosporium secalis) Compound 77 was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with barley scald fungus spores was dispensed. This plate was cultured at 18°C for 7 days to allow the barley scald fungus to grow. The absorbance at 550 nm of each well of the titer plate was then measured, and this value was used as the growth rate of the barley scald fungus. As a result, the growth rate in the plots treated with the compound was 50% or less of the growth rate in the untreated plot.
[0102] Test Example 4: Control test against cucumber gray mold fungus (Botrytis cinerea) The present compound was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), followed by 150 μL of complete medium previously inoculated with spores of Botrytis cinerea. The plate was incubated at 18°C for 4 days to allow the Botrytis cinerea fungus to grow, after which the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of Botrytis cinerea. As a result, each of the present compounds demonstrated plant disease control effects.
[0103] Test Example 5: Control test against peach scab fungus (Cladosporium carpophilum) Compound 77 was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with peach scab fungus spores was dispensed. This plate was cultured at 18°C for 5 days to allow the peach scab fungus to grow. The absorbance at 550 nm of each well of the titer plate was then measured, and this value was used as the growth rate of the peach scab fungus. As a result, the growth rate in the area treated with the compound was 50% or less of the growth rate in the untreated area.
[0104] Test Example 6: Control test against Cochliobolus miyabeanus Compound 77 was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of YB liquid medium inoculated with spores of Cochliobolus miyabeanus was dispensed. The plate was incubated at 23°C for 3 days to allow the Cochliobolus miyabeanus to grow. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of the Cochliobolus miyabeanus. As a result, the growth rate in the plots treated with the compound was 50% or less of that in the untreated plot.
[0105] Test Example 7: Control test against soybean rust (Phakopsora pachyrhizi) Leaf discs were prepared by cutting the true leaves of soybeans (cultivar: Kurosengoku) to a diameter of 1 cm. After dispensing 1 mL of agar medium (agar concentration 1.2%) into each well of a 24-well microplate, one leaf disc was placed on the agar medium in each well. 20 μL of a DMSO solution containing 10,000 ppm of the test compound was added to a mixture of 0.5 μL of Sorpol® 1200KX, 4.5 μL of DMSO, and 5 μL of xylene, and mixed. The resulting mixture was diluted with ion-exchanged water to prepare a mixture containing the test compound at the desired concentration. 10 μL of the resulting mixture was sprayed per leaf disc. One day later, a water suspension (1.0 x 10 / mL) of spores of soybean rust fungus (Phakopsora pachyrhizi) carrying the F129L amino acid substitution in the mitochondrial cytochrome b protein was sprayed onto the leaf disks. After inoculation, the disks were placed in a climate chamber (lights on for 6 hours, lights off for 18 hours, temperature 23°C, humidity 60%). After one day, the leaf disks were air-dried until all water droplets had disappeared from their surfaces, and then placed again in the climate chamber for 12 days. The area of soybean rust lesions was then examined. As a result, the lesion area of the leaf disks treated with any one of the present compounds 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 17, 18, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 33, 34, 36, 37, 38, 39, 40, 45, 46, 62, 66, 67, 68, 69, 70, 71, 73, 74, 76, or 78 at a predetermined concentration of 50 ppm was 30% or less of the lesion area of the untreated leaf disks.
[0106] Test Example 8: Control test against barley net blotch (Pyrenophora teres) Plastic pots were filled with soil, barley (variety: Nishinohoshi) was sown therein, and the pots were cultivated in a greenhouse for 7 days. Compounds 1, 3, 21, 41, and 44, formulated according to the method described in Formulation Example 1, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the barley so that sufficient adhesion was achieved on the leaves. After spraying, the barley was air-dried, and one day later, an aqueous suspension of spores of Pyrenophora teres pv. hordei was sprayed and inoculated. After inoculation, the barley was placed under humid conditions in a greenhouse at 23°C during the day and 20°C at night for 3 days, and then cultivated in the greenhouse for 7 days, after which the lesion area was examined. As a result, the lesion area in the barley treated with each of the compounds was 30% or less of the lesion area in the untreated barley.
[0107] Test Example 9: Control test against wheat rust (Puccinia recondita) Plastic pots were filled with soil, and wheat (cultivar: Shirogane) was sown therein and cultivated in a greenhouse for 9 days. Compounds 12, 17, or 39 formulated according to the method described in Formulation Example 1 were mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the foliage of the wheat so that it adhered well to the leaf surface. After spraying, the wheat was air-dried and cultivated at 20°C under illumination for 5 to 7 days, after which it was inoculated with wheat rust spores by sprinkling. After inoculation, the wheat was placed at 23°C under dark and humid conditions for 1 day, and then cultivated at 20°C under illumination for 8 days, and the lesion area was examined. As a result, the lesion area of the wheat treated with each of the compounds was 30% or less of that of the untreated wheat.
[0108] Test Example 10: Control test against wheat leaf blight (Septoria tritici) Plastic pots were filled with soil, wheat (cultivar: Apogee) was sown therein, and the soil was cultivated in a greenhouse for 10 days. Compounds 1, 2, 3, 4, 12, 22, 23, 26, 28, 43, 44, 53, 54, 55, 61, 62, and 65, formulated according to the method described in Formulation Example 1, were mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the foliage of the wheat so that it adhered well to the leaf surface. After spraying, the wheat was air-dried, and after 4 days, it was inoculated by spraying with an aqueous suspension containing spores of the wheat leaf blight fungus. After inoculation, the wheat was placed under 18°C and high humidity for 3 days, and then cultivated under light for 14 to 18 days, after which the lesion area was examined. As a result, the lesion area in the wheat treated with each of the above compounds was 30% or less of the lesion area in the untreated wheat.
[0109] Test Example 11: Control test against soybean rust (Phakopsora pachyrhizi) Soybeans (cultivar: Kurosengoku) were seeded in plastic pots filled with soil and grown in a greenhouse for 10 to 14 days. Compounds 3, 4, 11, 12, 13, 20, 21, 22, 23, 24, 25, 26, 36, 45, 46, 54, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, or 80, formulated according to the method described in Formulation Example 1, were mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the foliage of the soybeans so that sufficient adhesion was achieved to the leaf surface. After spraying, the soybeans were air-dried, and 2 to 5 days later, they were inoculated by spraying with an aqueous suspension of soybean rust spores. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1 to 2 days, and then cultivated in the greenhouse for 12 days, after which the lesion area was examined. As a result, the lesion area in the soybeans treated with each of the present compounds was 30% or less of that in the untreated soybeans.
[0110] Test Example 12: Control test against soybean rust (Phakopsora pachyrhizi) Soil was filled into plastic pots, soybeans (cultivar: Kurosengoku) were sown, and the plants were grown in a greenhouse for 10 days. An aqueous suspension containing soybean rust spores was then sprayed and inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1 day. After cultivation in the greenhouse for 2 days, the present compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and foliage of the soybeans so that it adhered well to the leaf surface. After spraying, the soybeans were air-dried and cultivated in the greenhouse for 8 days, after which the lesion area was examined. The results showed that each of the present compounds demonstrated plant disease control effects.
[0111] Test Example 13: Control test against soybean spot disease (Cercospora sojina) Soil was filled into plastic pots, soybeans (variety: Tachinagaha) were sown, and the plants were grown in a greenhouse for 13 days. The present compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and leaves of the soybeans so that sufficient adhesion was achieved to the leaf surface. After spraying, the soybeans were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension of spores of Cercospora sojina. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 3 days, and then cultivated in the greenhouse for 16 days, after which the lesion area was examined. As a result, each of the present compounds demonstrated plant disease control effects.
[0112] Test Example 14: Control test against tomato ring rot (Alternaria solani) Soil was filled into plastic pots, tomatoes (variety: Patio) were sown therein, and the plants were grown in a greenhouse for 20 days. The present compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and leaves of the tomatoes so that sufficient adhesion was achieved to the leaf surface. After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension of tomato ring rot spores. After inoculation, the tomatoes were kept at 18°C under humid conditions for 6 days, and the lesion area was then examined. As a result, each of the present compounds demonstrated plant disease control effects.
[0113] Test Example 15: Control test against soybean rust (Phakopsora pachyrhizi) The test compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 149 μL of a water suspension of soybean rust spores (1.0 × 10 / mL), which had previously been suspended in soybean rust spores, was dispensed. The plate was incubated at 23° C. for several hours, and the germinated soybean rust spores were counted. As a result, at a treatment concentration of 1 ppm, the number of germinated spores in wells containing any one of Compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 65, 66, 67, 68, 69, 70, 71, 73, 74, 75, 76, 77, 78, 79, or 80 as the test compound was 50% or less of the number of germinated spores in untreated wells.
[0114] The compound Y has a controlling effect against plant diseases and can be used for controlling plant diseases.
Claims
1. Formula (I) 【Chemistry 1】 [During the ceremony, R 1 represents a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, a 3-7 membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group B, a methyl group having one or more substituents selected from Group C, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group optionally have one or more substituents selected from Group E}, or NR 29 R 30 represents n represents 0, 1, or 2; R 2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from group B, OR 6 , S.R. 7 , S(O)R 8 , S(O) 2 R 9 , N.R. 10 R 11 , C(O)R 12 , a nitro group, a cyano group, or a halogen atom; p represents 0, 1, or 2; When p is 2, two R 2 may be the same or different, R 3 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B), a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may have one or more substituents selected from Group D), OR 13 , S.R. 14 , S(O)R 15 , S(O) 2 R 16 , N.R. 17 R 18 , C(O)R 19 , C(R 20 ) = NOR 21 , a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom; q represents 1, 2, or 3; When q is 2 or 3, two or three R 3 may be the same or different, R 4 and R 5 are the same or different and are each a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from group B, OR 22 , S.R. 23 , S(O)R 24 , S(O) 2 R 25 , N.R. 26 R 27 , C(O)R 28 , a nitro group, a cyano group, a halogen atom, or a hydrogen atom; R 6 , R 7 , R 10 , R 22 , R 23 , R 26 , and R 29 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 8 , R 9 , R 24 , R 25 , and R 30 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 11 , and R 27 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group (the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group optionally substituted with one or more halogen atoms), or a hydrogen atom; R 12 , R 19 , and R 28 are the same or different and represent a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, or a C2-C8 dialkylamino group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group are optionally substituted with one or more halogen atoms), R 13 , R 14 , R 15 , R 16 , and R 21 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group optionally have one or more substituents selected from Group A), a phenyl group, or a 5-6 membered aromatic heterocyclic group (the phenyl group and the 5-6 membered aromatic heterocyclic group optionally have one or more substituents selected from Group D), R 17 represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group optionally have one or more substituents selected from Group A), a phenyl group, a 5-6 membered aromatic heterocyclic group (the phenyl group and the 5-6 membered aromatic heterocyclic group optionally have one or more substituents selected from Group D), a (C1-C6 alkyl)carbonyl group, or a (C1-C6 alkoxy)carbonyl group (the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group are optionally substituted with one or more halogen atoms), R 18 and R 20 are the same or different and represent a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, or a hydrogen atom; Adjacent R 3 and R 4 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally have one or more substituents selected from Group E), Two adjacent R 3 and R 3 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle optionally have one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle optionally have one or more substituents selected from Group E). Group A: the group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group D}, a halogen atom, a cyano group, a nitro group, and a hydroxy group. Group B: a group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms), a hydroxy group, a halogen atom, and a cyano group. Group C: the group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group B}, a phenyl group, and a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group D}. Group D: a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a (C1-C6 alkyl)carbonylamino group, a (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkyl the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group, and the (C1-C6 alkoxy)carbonylamino group are optionally substituted with one or more halogen atoms}, the group consisting of a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, an amino group, a nitro group, a cyano group, a hydroxy group, and a halogen atom. Group E: a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a hydroxy group, a halogen atom, and a cyano group.
1. A method for controlling plant diseases, which comprises treating a plant or the soil in which the plant is grown with a compound represented by the following formula (I):
2. In claim 1, the compound represented by formula (I) or its N-oxide, or a salt thereof is R 1 is a C2-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group optionally having one or more substituents selected from Group B, or a methyl group having one or more substituents selected from Group C, or an N-oxide thereof, or a salt thereof.
3. In claim 1, the compound represented by formula (I) or its N-oxide, or a salt thereof is R 1 is a C2-C6 chain hydrocarbon group, and R 2 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, and R 3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A, OR 13 , S.R. 14 , S(O)R 15 , S(O) 2 R 16 , N.R. 17 R 18 , C(O)R 19 , C(R 20 ) = NOR 21 , a cyano group, a nitro group, an amino group, a hydroxy group, or a halogen atom, and two adjacent R 3 and R 3 may form, together with the carbon atom to which they are bonded, a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle may have one or more substituents selected from Group B}, and R 4 and R 5 The method according to claim 1, wherein are the same or different and are a halogen atom or a hydrogen atom, or an N-oxide thereof, or a salt thereof.
4. Use of a compound represented by formula (I) according to any one of claims 1 to 3, or an N-oxide thereof, or a salt thereof, for controlling plant diseases.
5. A method for controlling soybean rust fungi, which comprises treating soybeans or soil in which soybeans are grown with the compound represented by formula (I) according to any one of claims 1 to 3, or an N-oxide thereof, or a salt thereof.
6. Formula (II) 【Chemistry 2】 [During the ceremony, R 1a represents a C2-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group optionally substituted with one or more halogen atoms, a phenyl group, or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are optionally substituted with one or more halogen atoms}, R 3a represents a C1-C3 alkyl group, a C1-C3 alkoxy group, a cyclopropyl group (the cyclopropyl group may be substituted with one or more halogen atoms), or a halogen atom; qa represents 1, 2, or 3; When qa is 2 or 3, two or three R 3a may be the same or different, R 4a and R 5a represents a hydrogen atom. or an N-oxide thereof, or a salt thereof.
7. 7. A pesticide composition comprising the compound according to claim 6, its N-oxide, or a salt thereof, and an inert carrier.
8. A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound according to claim 6 or an N-oxide thereof, or a salt thereof: Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): repellent ingredients.
9. A method for controlling plant diseases, which comprises applying an effective amount of the compound or N-oxide thereof or a salt thereof according to claim 6 or an effective amount of the composition according to claim 8 to a plant or the soil in which the plant is grown.
10. Use of the compound according to claim 6, or an N-oxide thereof, or a salt thereof, or the composition according to claim 8, for controlling plant diseases.
11. A seed or vegetative reproductive organ bearing an effective amount of the compound of claim 6 or its N-oxide or salt thereof, or an effective amount of the composition of claim 8.