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WO-2026094958-A1 - PLANT DISEASE CONTROL METHOD

WO2026094958A1WO 2026094958 A1WO2026094958 A1WO 2026094958A1WO-2026094958-A1

Abstract

The present invention provides an excellent plant disease control method. According to the present invention, compounds represented by formula (I) or N-oxides thereof or salts of the compounds or N-oxides can be used for plant disease control. (In the formula, R 1 is a C1–6 chain-type hydrocarbon group or the like, R 2 is a C1–6 chain-type hydrocarbon group or the like, n and R 3 are either a combination of n being 0, 1, or 2 and R 3 being a C2–6 chain-type hydrocarbon group or the like or a combination of n being 2 and R 3 being NR 8 R 9 , R 4 , R 5 , R 6 , and R 7 are the same or different and are a C1–6 chain-type hydrocarbon group or the like, R 8 is a C1–6 chain-type hydrocarbon group or the like, R 9 is a C1–6 chain-type hydrocarbon group or the like, and Z 1 is a phenyl group or the like.)

Inventors

  • ARAI, Keisuke
  • MAEHATA, NAO
  • ICHIHASHI, Kazuki

Assignees

  • 住友化学株式会社

Dates

Publication Date
20260507
Application Date
20251029
Priority Date
20241030

Claims (7)

  1. Equation (I) [During the ceremony, R1 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 may be substituted with one or more substituents selected from group A), a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, an amino group, a hydroxyl group, a halogen atom, or a hydrogen atom. R2 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 may be substituted with one or more substituents selected from group A), a halogen atom, or a hydrogen atom. The combinations of n and R3 are: n is 0, 1, or 2, A combination in which R 3 is a C2-C6 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group, or a 3-6 membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group C}; or, n is 2, R 3 represents the combination NR 8 R 9 , R4 , R5 , R6 , and R7 represent a C1-C6 chain hydrocarbon group, a cyclopropyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, which may be the same or different and substituted with one or more substituents selected from group A. R 8 represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, which may be substituted with one or more substituents selected from group A. R9 represents a C1-C6 chain hydrocarbon group or a C3-C8 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group A. Z 1 represents a phenyl group, a 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {the phenyl group and the 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) may be substituted with one or more substituents selected from group D}, a C3-C8 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a 3-8 member non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group E, or OR 10 . R 10 represents a C3-C8 alicyclic hydrocarbon group or a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}. Group A: A group consisting of C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {the C1-C6 alkoxy groups, the C1-C6 alkylamino groups, and the C2-C8 dialkylamino groups may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups {the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group F}, halogen atoms, cyano groups, nitro groups, and hydroxyl groups. Group B: A group consisting of oxo groups, thioxo groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, {the C1-C6 chain hydrocarbon groups, the C1-C6 alkoxy groups, the C1-C6 alkylamino groups, and the C2-C8 dialkylamino groups may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and sulfanyl groups. Group C: A group consisting of C1-C6 alkoxy groups, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups, fluorine atoms, cyano groups, nitro groups, and hydroxyl groups, which may be substituted with one or more halogen atoms. Group D: A group consisting of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {the C1-C6 chain hydrocarbon groups, the C1-C6 alkoxy groups, the C1-C6 alkylamino groups, and the C2-C8 dialkylamino groups may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups {the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group F}, halogen atoms, cyano groups, and nitro groups. Group E: A group consisting of oxo groups, thioxo groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, {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}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and sulfanyl groups. Group F: A group consisting of oxo groups, halogen atoms, C1-C4 alkyl groups, C1-C4 alkoxy groups, C1-C4 haloalkyl groups, C1-C4 haloalkoxy groups, and cyano groups. A method for controlling plant diseases, comprising treating plants or soil in which plants are cultivated with a compound represented by, or its N oxide, or a salt thereof.
  2. Formula (II) [During the ceremony, na represents 0, 1, or 2. R 1a represents a C1-C6 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group, a 3-6 membered non-aromatic heterocyclic group (the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group E a ), a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, an amino group, a hydroxyl group, a halogen atom, or a hydrogen atom. R 2a represents a C1-C6 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group, a 3-6 membered non-aromatic heterocyclic group (the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group E a ), a halogen atom, or a hydrogen atom. R 3a represents a C2-C6 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group, or a 3-6 member non-aromatic heterocyclic group which may be substituted with 1, 2, 3, 4, or 5 substituents selected from group C a {the C3-C6 alicyclic hydrocarbon group and the 3-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group E a }, R 4a represents a C1-C4 chain hydrocarbon group, a cyclopropyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a cyano group, a halogen atom, or a hydroxyl group, which may be substituted with one or more substituents selected from group A a. R 5a represents a C1-C4 chain hydrocarbon group, a cyclopropyl group, a C1-C3 alkoxy group , a C1-C3 haloalkoxy group, a cyano group, a halogen atom, a hydroxyl group, or a hydrogen atom, which may be substituted with one or more substituents selected from group A a. Z 1a represents a phenyl group, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {the phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) may be substituted with one or more substituents selected from group D a }, a C5-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B a , a C3-C4 cycloalkyl group which may be substituted with one or more substituents selected from group B a , or OR 10a . R 10a represents a C3-C8 alicyclic hydrocarbon group or a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group E a }. Group A a : A group consisting of a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino 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}, a C3-C6 alicyclic hydrocarbon group, a 3-6 membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group E a }, a halogen atom, a cyano group, a nitro group, and a hydroxyl group. Group B a : A group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, 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}, a C3-C6 alicyclic hydrocarbon group, a 3-6 membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group E a }, a halogen atom, a cyano group, a nitro group, and a hydroxyl group. Group C a : A group consisting of C1-C6 alkoxy groups, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups, fluorine atoms, cyano groups, nitro groups, and hydroxyl groups, which may be substituted with one or more halogen atoms. Group D a : A group consisting of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {the C1-C6 chain hydrocarbon groups, the C1-C6 alkoxy groups, the C1-C6 alkylamino groups, and the C2-C8 dialkylamino groups may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups {the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group E a }, halogen atoms, cyano groups, and nitro groups. Group E a : A group consisting of an oxo group, a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkyl group, a C1-C4 haloalkoxy group, and a cyano group. Compounds represented by, or their N oxides or salts thereof.
  3. A composition containing the compound described in claim 2, its N oxide, or a salt thereof, and an inert carrier.
  4. 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 or its N oxide or salt thereof as described in claim 2: Group (a): A group consisting of insecticidal components, acaricidal components, and nematicidal components; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): Repellent components.
  5. A method for controlling plant diseases, comprising treating a plant or soil in which a plant is cultivated with an effective amount of the compound described in claim 2, its N oxide, or a salt thereof, or an effective amount of the composition described in claim 4.
  6. Use of the compound described in claim 2, its N oxide, or a salt thereof, or the composition described in claim 4, for controlling plant diseases.
  7. Seeds or vegetative reproductive organs containing an effective amount of the compound described in claim 2, its N oxide, or a salt thereof, or an effective amount of the composition described in claim 4.

Description

Methods for controlling plant diseases This application claims priority and benefits of Japanese Patent Application No. 2024-190368, filed on 30 October 2024, the entire contents of which are incorporated herein by reference. This invention relates to a method for controlling plant diseases. Patent Document 1 describes sulfonyl compounds. The substituents in this invention will now be described. Halogen atoms refer to fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms. If a substituent is substituted with two or more halogen atoms or substituents, those halogen atoms or substituents may be the same or different. In this specification, the phrase "may be substituted with one or more substituents selected from group X" (where X means any one of A, B, C, D, DN , E, F, Aa , Ba , Ca , Da , DNa , Ea , and ENa ) means that if there are two or more substituents selected from group X, those substituents may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is X through Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 through 6. A chain-like 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 groups. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl groups. Examples of alkynyl groups include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group, and 5-hexynyl group. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Examples of haloalkoxy groups include trifluoromethyl, difluoromethyl, monofluoromethyl, trichloromethyl, two CH₂CHF groups, three CH₂CF groups , three CH₂CH₂CF groups , three CH₂CH₂CH₂CF groups , three CH₂CH₂CH₂CH₂CF groups , and three CH₂CH₂CH₂CH₂CH₂CF groups . Examples of C1-C6 alkylamino groups include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, sec-butylamino group, tert-butylamino group, pentylamino group, and hexylamino group. Examples of C2-C8 dialkylamino groups include dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, ethylmethylamino group, methylpropylamino group, isopropylmethylamino group, butylmethylamino group, ethylpropylamino group, ethylisopropylamino group, butylethylamino group, isopropylpropylamino group, butylpropylamino group, and butylisopropylamino group. Examples of alicyclic hydrocarbon groups include cycloalkyl groups and cycloalkenyl groups. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of cycloalkenyl groups include cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl groups. Examples of non-aromatic heterocyclic groups include azilidinyl group, oxyranyl group, thyranyl group, azetidinyl group, oxetanyl group, thietanyl group, pyrrolidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, pyrazolinyl group, pyrazolidinyl group, imidazolinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, isoxazolidinyl group, isothiazolidinyl group, isothiazolidinyl group, dioxolanyl group, dioxanyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, azepanyl group, oxepanyl group, thiepanyl group, and azokanyl group. Examples of aromatic heterocyclic groups include five-membered aromatic heterocyclic groups such as pyrrolyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, and thiadiazolyl groups; and six-membered aromatic heterocyclic groups such as pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetradinyl groups. The N oxide of a compound represented by formula (I) or formula (II) refers to a structure in which at least one nitrogen atom in the compound represented by formula (I) or formula (II) is substituted with an oxo group. The compound in question, or the compound of the present invention, may have one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and mixtures of stereoisomers in any ratio. The compound represented by formula (I) or formula (II), or its N oxide, may form acid addition salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, and benzoate when mixed with acids such as hydrochloric a