N–substituted oxyamide compound or salt thereof

Abstract

Provided is a novel compound exhibiting an excellent controlling effect on harmful plant diseases. A compound represented by formula (I) (wherein each symbol is as defined in the description) or a salt thereof exhibits an excellent controlling effect on harmful plant diseases.

Description

N-substituted oxyamide compound or its salt

[0001] The present invention relates to novel N-substituted oxyamide compounds or salts thereof, and agricultural and horticultural fungicides containing them as active ingredients.

[0002] There is a strong demand for new agricultural and horticultural fungicides because existing agricultural and horticultural fungicides have problems such as insufficient practical control effects against harmful plant diseases depending on the application scene, the emergence of drug-resistant bacteria, and environmental load (impact on surrounding plants and ecosystems).Furthermore, from the viewpoint of preventing environmental pollution, there is a demand for agricultural and horticultural fungicides that exhibit excellent control effects against harmful plant diseases at the lowest possible dosage.

[0003] Patent Document 1 discloses amide compounds and their use in controlling plant diseases. However, Patent Document 1 does not make any specific disclosure of the compound represented by the following formula (I). Compounds that can be used as microbicides, such as N-alkoxycarboxamides, are known (Patent Document 2). However, Patent Document 2 does not make any specific disclosure of the compound represented by the following formula (I). Non-Patent Document 1, starting from Table I, No. 15, discloses 5-hydroxytryptophan decarboxylase inhibitory activity tests and monoamine oxidase inhibitory activity tests of N-Benzoyl-N-benzyl-O-2-propylhydroxylamine. However, there is no disclosure whatsoever regarding the control effect of the compounds described in Non-Patent Document 1 against harmful plant diseases. Furthermore, Non-Patent Document 1 does not make any disclosure of the compound represented by the following formula (I). On the other hand, the compounds 2-amino-N-benzyl-N-methoxy-1,3-thiazole-5-carboxamide (CAS registration number: 2301497-10-7) and 2-amino-N-benzyl-N-methoxy-4-methyl-1,3-thiazole-5-carboxamide (CAS registration number: 2299658-69-6) are known. However, their uses are unknown, and naturally, nothing is known about the effects of these compounds on plant diseases.

[0004] International Publication No. 2010 / 134634 International Publication No. 2011 / 023645

[0005] Journal of Medicinal Chemistry 1969, 12(1), 45-48

[0006] An object of the present invention is to provide novel compounds which exhibit excellent control effects against harmful plant diseases.

[0007] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have found that a compound represented by the following formula (I) or a salt thereof exhibits excellent control effects against harmful plant diseases. That is, the present invention is as follows: [1] A compound represented by the formula (I):

[0008] [In the formula, R １ is (C １ -C ５ )-chain hydrocarbon, or (C ３ -C ４ )-cycloalkyl {wherein the (C １ -C ５ )-chain hydrocarbons and the (C ３ -C ４ )-cycloalkyl is at least one T １ may be substituted with}, T １ is halogen, cyano, or -U １ -R ２ and U １ is O, S, or C(=O)O, R ２ is (C １ -C ３ )-alkyl, and X １ is a halogen, and Y １ , Y ２ , Y ３ , Y ４ and Y ５ are each independently a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, cyano, or a hydrogen atom, provided that R １ But (C １ -C ４)-alkyl or (C ３ -C ４ )-cycloalkyl, then Y １ , Y ２ , Y ３ , Y ４ and Y ５ and n is 0 or 1. The compound represented by the formula (I) or a salt thereof, wherein n is 0 or 1, and n is 1 or 2.

[0009] [2] R １ However, (C １ -C ４ )-alkyl, (C ３ -C ４ )-cycloalkyl, or (C ３ -C ５ )-alkynyl, or a salt thereof, according to the above [1].

[0010] [3] The compound of formula (I) is represented by formula (IA):

[0011] [In the formula, R １Ａ is (C １ -C ４ )-alkyl, or (C ３ -C ４ )-cycloalkyl, and X １ is a halogen, and Y １ is a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, cyano, or a hydrogen atom; Y ２Ａ , Y ３Ａ and Y ４Ａ are each independently a hydrogen atom or a halogen atom; ５Ａ is a hydrogen atom. １ is a hydrogen atom, Y ２Ａ , Y ３Ａ and Y ４Ａ and n is 0 or 1. The compound or salt thereof according to the above item [1] is an N-(cyclo)alkoxyamide compound represented by the formula:

[0012] [4] The compound of formula (I) is represented by formula (IB):

[0013] wherein n is 1, 2, or 3; １ is a halogen, and Y １ , Y ２ , Y ３ , Y ４ and Y ５ are each independently a hydrogen atom, a halogen atom, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, or cyano.] (hereinafter, also referred to as compound (IB)).

[0014] [5] The compound of formula (I) is represented by formula (IA):

[0015] [In the formula, R １Ａ is (C １ -C ４ )-alkyl, or (C ３ -C ４ )-cycloalkyl, and X １ is a halogen, and Y １ is a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, cyano, or a hydrogen atom; Y ２Ａ , Y ３Ａ and Y ４Ａ are each independently a hydrogen atom or a halogen atom; ５Ａ is a hydrogen atom. １ is a hydrogen atom, Y ２Ａ , Y ３Ａ and Y ４Ａ and n is 0 or 1. In the formula (IB), n is 0 or 1, and n is 1 or 2, and n is 2 or 3, and n is 3 or 4, and n is 4 or 5. In the formula (IB), n is 0 or 1, and n is 1 or 2, and n is 2 or 3, and n is 3 or 4. In the formula (IB), n is 0 or 1, and n is 1 or 2, and n is

[0016] wherein n is 1, 2, or 3; １ is a halogen, and Y １ , Y ２ , Y３ , Y ４ and Y ５ are each independently a hydrogen atom, a halogen atom, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, or cyano.] The compound or salt thereof according to the above [1], which is an N-alkynyloxyamide compound represented by the formula:

[0017] [6] Y １ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, or cyano; or a salt thereof according to any one of [1] to [5].

[0018] [7] R １Ａ is methyl, ethyl or cyclopropyl, or a salt thereof according to the above [3] or [5].

[0019] [8] Y ５ is a hydrogen atom, or a salt thereof according to any one of [1], [2], and [4] to [6].

[0020] [9] An agricultural and horticultural fungicide containing the compound or salt thereof according to any one of [1] to [8] above as an active ingredient.

[0021]

[10] A method for controlling harmful plant diseases, comprising applying an effective amount of the compound or salt thereof according to any one of [1] to [8] to a plant, a plant pathogen, or soil.

[0022] The compound (I) of the present invention exhibits excellent control effects against harmful plant diseases and is useful as an agricultural and horticultural fungicide.

[0023] Various substituents and chemical structures described herein will be explained. Compound (I) includes compounds (IA) and (IB), which are also collectively referred to as the compounds of the present invention.

[0024] The halogen or halogen as a substituent may be a fluorine, chlorine, bromine, or iodine atom. The number of halogen as a substituent may be one or more, and when there are two or more, the halogen atoms may be the same or different. In addition, the substitution position of the halogen as a substituent may be any position.

[0025] "C Ｐ -C Ｔ " means that the number of carbon atoms is P to T. For example, "C １ -C ４ " means that the number of carbon atoms is 1 to 4. Furthermore, the expression "optionally substituted" means that the group has a substituent or is unsubstituted.

[0026] (C １ -C ５ )-chain hydrocarbons are (C １ -C ４ )-alkyl, (C ３ -C ５ )-alkynyl, or (C ３ -C ５ )-alkenyl. １ -C ４ )-Alkyl includes, for example, straight or branched alkyl groups having 1 to 4 carbon atoms such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, or tertiary butyl.

[0027] (C ３ -C ５ Examples of the alkynyl include 1-propynyl, propargyl (also simply referred to as 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, 3-butyn-2-yl, buta-1,3-diynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 3-pentyn-2-yl, 1-pentyn-3-yl, 4-pentyn-2-yl, 2-methyl-3-butynyl, penta-1,3-diynyl, penta-1,4-diynyl, and penta-2,4-diynyl, and have at least one triple bond at any position, and are straight-chain or branched-chain alkynyl groups having 3 to 5 carbon atoms.

[0028] (C ３ -C ５ Examples of the )-alkenyl include allyl (also simply referred to as 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, buta-1,3-dienyl, buta-1,3-dien-2-yl, 2-methyl-1-propenyl, 2-buten-2-yl, 3-buten-2-yl, 2-methyl-2-propenyl, 3-buten-3-yl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-penten-2-yl, 3-methyl-2-buten-2-yl, 3-methyl-2-butenyl, penta-1,3-dienyl, penta-2,4-dienyl, and penta-2,4-dien-2-yl. Examples of the )-alkenyl include linear or branched alkenyl groups having 3 to 5 carbon atoms and having at least one double bond at any position. Furthermore, when there are geometric isomers, they are either the E-form or the Z-form alone, or a mixture of the E-form and the Z-form in any ratio, and are not particularly limited as long as they are within the specified range of carbon numbers.

[0029] (C １ -C ６ Examples of the (C)-alkyl include linear or branched alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, isopentyl, neopentyl, secondary pentyl, 1-ethylpropyl, tertiary pentyl, normal hexyl, isohexyl, secondary hexyl, 2-methylpentyl, 3-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, tertiary hexyl, 2,2-dimethylbutyl, neohexyl, 1-ethyl-2-methylpropyl, and 1-ethyl-1-methylpropyl. １ -C ３ )-alkyl represents a straight or branched alkyl group having 1 to 3 carbon atoms. Specific examples thereof include the above (C １ -C ６ Specific examples of )-alkyl include alkyl groups having 1 to 3 carbon atoms.

[0030] (C ３ -C ４ )-cycloalkyl represents a cyclic hydrocarbon group having 3 to 4 carbon atoms, and can form a 3- to 4-membered monocyclic structure. When forming a 3-membered monocyclic structure, it may be substituted with a methyl group at any position within the specified range of carbon atoms. Examples include cycloalkyl groups having 3 to 4 carbon atoms, such as cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, and cyclobutyl.

[0031] Said (C １ -C ５ )-chain hydrocarbons and the (C ３ -C ４ )-cycloalkyl is at least one T １ The above (C １ -C ５ ) - A chain hydrocarbon is T １ When substituted with the above (C １ -C ５ )-chain hydrocarbon is 1 to 9 T １ It can be replaced by the above (C ３ -C ４ )-cycloalkyl is T １ When substituted with the above (C ３ -C ４ )-cycloalkyl is 1 to 7 T １ It can be replaced by the above (C １ -C ５ )-chain hydrocarbon or the (C ３ -C ４ )-cycloalkyl is at least one T １ When replaced with T １ The substitution position of １ -C ５ )-chain hydrocarbon or the (C ３ -C ４ The substitution position on the cycloalkyl may be any position. １ -C ５ )-chain hydrocarbon or the (C ３ -C ４ )-cycloalkyl is two or more T １When replaced by １ may be the same or different. For example, R １ At least one T １ (C １ -C ４ )-alkyl, specifically includes the following substituents: For example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, methoxymethyl, ethoxymethyl, propoxymethyl, 2-methoxyethyl, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, isopropoxycarbonylmethyl, and the like.

[0032] For example, R of compound (I) １ At least one T １ (C ３ -C ４)-cycloalkyl, specifically includes the following substituents: For example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methoxycyclopropyl, 2-methoxycyclopropyl, 1-methylthiocyclopropyl, 2-methylthiocyclopropyl, 1-methoxycarbonylcyclopropyl, 2-methoxycarbonylcyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 2,2-difluorocyclobutyl, 3,3-difluorocyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-methoxycyclobutyl, 2-methoxycyclobutyl, 3-methoxycyclobutyl, 1-methylthiocyclobutyl, 2-methylthiocyclobutyl, 3-methylthiocyclobutyl, 1-methoxycarbonylcyclobutyl, 2-methoxycarbonylcyclobutyl, and 3-methoxycarbonylcyclobutyl.

[0033] (C １ -C ６)-haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, chloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 1-fluoro-2-propyl, 3-fluoropropyl, 2-fluoro-2-propyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,1,3,3,3-hexafluoroisopropyl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 1,1-difluorobutyl, 2,2-difluorobutyl, 3,3-difluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, perfluorobutyl, 2,3,3,3,4,4,4-heptafluoroisobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 1,1-difluoropentyl, 2,2-difluorobutyl fluoropentyl, 3,3-difluoropentyl, 4,4-difluoropentyl, 5,5-difluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, perfluoropentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-fluorohexyl, 1,1-difluorohexyl, 2,2-difluorohexyl, 3,Examples include linear or branched alkyl groups having 1 to 6 carbon atoms partially or completely substituted with 1 to 13 identical or different halogen atoms, such as 3-difluorohexyl, 4,4-difluorohexyl, 5,5-difluorohexyl, 6,6-difluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4,5,5,6,6,6-heptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl, or perfluorohexyl.

[0034] (C １ -C ３ )-haloalkyl represents a straight or branched chain haloalkyl group having 1 to 3 carbon atoms. Specific examples thereof include the above (C １ -C ６ Specific examples of )-haloalkyl include haloalkyl groups having 1 to 3 carbon atoms.

[0035] In the formula (IB), n is 1, 2, or 3, and therefore, the compound (IB) is specifically represented by the following formulas (IB-a) to (IB-c).

[0036]

[0037] Among the compounds represented by formula (I), preferred compounds include N-(cyclo)alkoxyamide compounds of formula (IA), N-alkynyloxyamide compounds of formula (IB), and compounds represented by the following formulae (I-a) to (I-m):

[0038] The salt of compound (I) includes any salt that is agriculturally acceptable, and examples thereof include alkali metal salts (e.g., sodium salt, potassium salt, etc.), alkaline earth metal salts (e.g., magnesium salt, calcium salt, etc.), amine salts (dimethylamine salt, triethylamine salt, etc.), inorganic acid salts (e.g., hydrochloride, perchlorate, sulfate, nitrate, etc.), and organic acid salts (e.g., acetate, methanesulfonate, paratoluenesulfonate, oxalate, etc.).

[0039] Compound (I) exists in various isomers, such as optical isomers and geometric isomers, and the present invention may include both each isomer and a mixture of isomers. Note that compound (I) also includes various isomers other than those described above within the scope of common general knowledge in the technical field. Furthermore, various isomers can be produced separately using common general knowledge in the technical field and general experimental techniques.

[0040] Furthermore, depending on the type of isomer, the chemical structure may differ from the structural formula shown, but a person skilled in the art would be able to fully recognize that they are isomers, and therefore it is clear that they are within the scope of the present invention.

[0041] Next, a method for producing compound (I) will be described. Compound (I) can be produced according to the following reactions A to E and a conventional method for producing a salt, but the method for obtaining the compound is not limited to these methods. For example, compound (I) of the present invention can also be produced by applying various substituent conversion reactions well known in the art (e.g., alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction, Sandmeyer reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.) to the substituent on the phenyl group. Furthermore, protection and deprotection reactions commonly used in the art may be applied, if necessary, in the production of the compound of the present invention. When carrying out the reaction, it may be carried out under an inert gas atmosphere such as nitrogen or argon, and a salt reagent may be used.

[0042] [Reaction A] Reaction A is a deprotection reaction, in which the Boc group is removed from the compound of formula (XX-a) to obtain the compound of formula (I), where the Boc group is a tert-butoxycarbonyl group.

[0043]

[0044] The symbols in the formula are as defined above.

[0045] Reaction A can be carried out under known conditions used for removing a Boc group, for example, the method described in Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (John Wiley and Sons, 2007, Peter G. M. Wuts, Theodora W. Greene). More specifically, for example, reaction can be carried out by reacting the compound of formula (XX-a) with an acid such as trifluoroacetic acid or hydrogen chloride in the presence of a solvent, or by reacting it with trimethylsilyl triflate in the presence of a solvent and a base such as 2,6-lutidine.

[0046] [Reaction B] and [Reaction C] Reaction B is a method of reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (XX-b). Reaction C is a method of reacting a compound of formula (II-a) with a compound of formula (III) to obtain a compound of formula (XX-b).

[0047]

[0048] In the formula, R １ａ is H, (C １ -C ５ )-chain hydrocarbon, or (C ３ -C ４ )-cycloalkyl {wherein the (C １ -C ５ )-chain hydrocarbons and the (C ３ -C ４ )-cycloalkyl is at least one T １ L is a leaving group, and examples thereof include halogen, alkoxy, aryloxy, alkylcarbonyloxy, and arylcarbonyloxy. Other symbols are as defined above.

[0049] Reaction B can be carried out usually in the presence of a dehydration condensation agent and a solvent, optionally with the addition of a base. The compound of formula (III) in reaction B can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II) (the "equivalent" refers to a molar equivalent, and the same applies hereinafter).

[0050] Examples of the dehydration condensation agent in Reaction B include carbodiimide-based condensation agents such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC) or their hydrochlorides; imidazole-based condensation agents such as 1,1'-carbonyldiimidazole (CDI); triazine-based condensation agents such as 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM); phosphonium-based condensation agents such as 1H-benzotriazol-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate (PyBOP); and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium. Examples of suitable dehydration condensation agents include, but are not limited to, uronium-based condensation agents such as 3-oxidohexafluorophosphate (HATU); acid anhydrides such as 2-methyl-6-nitrobenzoic anhydride (MNBA); 2-halopyridinium salts such as 2-chloro-1-methylpyridinium p-toluenesulfonate; propylphosphonic anhydride (cyclic trimer) (T3P); and diphenylphosphoric azide (DPPA). If necessary, a common additive used with dehydration condensation agents, such as 1-hydroxybenzotriazole (HOBt), may be added. The dehydration condensation agent may be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II), and the additive may be used in an amount of 0.2 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II).

[0051] The base in Reaction B can be selected from, for example, carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and the like. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (II).

[0052] The solvent in Reaction B may be any solvent inert to the reaction, and can be appropriately selected from, for example, one or more solvents selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water.

[0053] The reaction temperature for reaction B is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0054] Reaction C can be carried out in the presence of a solvent, optionally with the addition of a base. The compound of formula (III) in Reaction C can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II-a).

[0055] The base in Reaction C can be selected from, for example, carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and the like. The base can be used in an amount of 0.1 to 10 equivalents, preferably 0.5 to 5 equivalents, relative to 1 equivalent of the compound of Formula (II-a).

[0056] The solvent in Reaction C may be any solvent inert to the reaction, and can be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water.

[0057] The reaction temperature for Reaction C is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0058] The compound of formula (III) used in reactions B and C can be produced according to reaction 2-2 or reaction 2-4 described below. The compound of formula (II) used in reaction B can be produced according to reaction 1-1 or reaction 1-2 described below or a known method, or a commercially available product may be used. The compound of formula (II-a) used in reaction C can be produced from the compound of formula (II) according to reaction 1-4 described below or a known method. The compound of formula (II-a) may be a commercially available product.

[0059] [Reaction D] Reaction D is a method of obtaining a compound of formula (XX-a) by reacting a compound of formula (XX-c) with a compound of formula (IV).

[0060]

[0061] In the ceremony, L １ is a leaving group, and examples thereof include halogen, trifluoromethanesulfonyloxy, methanesulfonyloxy, and paratoluenesulfonyloxy, and other symbols are as defined above.

[0062] Reaction D can usually be carried out in the presence of a base and a solvent, and if necessary, by adding a phase transfer catalyst. In Reaction D, the compound of formula (IV) can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per equivalent of the compound of formula (XX-c).

[0063] The base in Reaction D can be selected from, for example, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; organolithium compounds such as n-butyllithium and lithium diisopropylamide; and alkali metal carboxylates such as sodium acetate and potassium acetate. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of Formula (XX-c).

[0064] The solvent in Reaction D may be any solvent inert to the reaction, and may be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol, and tert-butanol; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and water.

[0065] Examples of the phase transfer catalyst in Reaction D include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. The phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents relative to 1 equivalent of the compound of Formula (XX-c).

[0066] The reaction temperature for reaction D is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 48 hours, preferably about 1 to 24 hours.

[0067] The compound of formula (IV) used in reaction D can be produced according to known methods, or a commercially available product may be used.

[0068] [Reaction E] Reaction E is a method of obtaining a compound of formula (XX-b) by reacting a compound of formula (II-b) with a compound of formula (V).

[0069]

[0070] The symbols in the formula are as defined above.

[0071] Reaction E can be carried out in accordance with the above-mentioned Reaction D. In Reaction E, the compound of formula (V) can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (II-b). In Reaction E, the base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (II-b). In Reaction E, the phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents per equivalent of the compound of formula (II-b).

[0072] The compound of formula (II-b) used in reaction E can be produced according to the following reaction 1-3 or a known method, or a commercially available product may be used. The compound of formula (V) used in reaction E can be produced according to a known method, or a commercially available product may be used.

[0073] The compounds used in Reactions A to E can be produced according to the following methods for producing the respective intermediates (Reactions 1-1 to 1-4 and Reactions 2-1 to 2-4) and conventional methods for producing salts, but are not limited to these methods. These compounds may be produced according to known methods, or commercially available products may be used.

[0074] Methods for producing each intermediate [Reaction 1-1], [Reaction 1-2], and [Reaction 1-3] Reaction 1-1 is a method of oxidizing a compound of formula (1) to obtain a compound of formula (II). Reaction 1-2 is a method of hydrolyzing a compound of formula (2) to obtain a compound of formula (II). Reaction 1-3 is a method of reacting a compound of formula (II) or a compound of formula (II-a) with a compound of formula (3) to obtain a compound of formula (II-b).

[0075]

[0076] Z during the ceremony １ Reaction 1-1 can be carried out under general Pinnick oxidation conditions, for example, according to the method described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.

[0077] The compound of formula (1) used in reaction 1-1 can be produced according to known methods, for example, Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182, Journal of Organic Chemistry, 2005, 70, 567-574, WO 2020 / 028141, or Organic Process Research and Development, 2021, 25, 1167-1175, or commercially available products may be used.

[0078] Reaction 1-2 can be carried out under general ester hydrolysis conditions, for example, in accordance with the method described in WO 2009 / 100171.

[0079] The compound of formula (2) used in reaction 1-2 can be produced by a known method, for example, in accordance with the method described in WO 2012 / 006760, or a commercially available product may be used.

[0080] Reaction 1-3 can be carried out in accordance with the above-mentioned Reaction B or Reaction C. In Reaction 1-3, the compound of formula (3) can be used in an amount of 0.5 to 10 equivalents, preferably 0.7 to 5 equivalents, per equivalent of the compound of formula (II) or the compound of formula (II-a).

[0081] The compound of formula (3) used in reaction 1-3 may be produced in accordance with known methods, for example, WO 2006 / 138350, U.S. Patent Application Publication No. 2014 / 0378399, Organic & Biomolecular Chemistry, 2020, 18, 3281-3287, The Journal of Antibiotics, 2000, 53, 1071-1085, or a commercially available product may be used.

[0082] [Reaction 1-4] Reaction 1-4 is a method for obtaining a compound of formula (II-a) from a compound of formula (II) by halogenation, esterification or carbonylation.

[0083]

[0084] The symbols in the formula are as defined above.

[0085] When Reaction 1-4 is halogenation, the reaction conditions are as follows.

[0086] In Reaction 1-4, when L in the compound of Formula (II-a) is halogen, halogenation can typically be carried out by reacting the compound of Formula (II) with a halogenating agent in the presence of a solvent, and N,N-dimethylformamide may be added as needed. Examples of halogenating agents used in Reaction 1-4 include oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, and sulfuryl chloride. The halogenating agent can be used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, per equivalent of the compound of Formula (II). An excess amount may be used if no problems occur in the reaction. When N,N-dimethylformamide is used in Reaction 1-4, the amount of N,N-dimethylformamide used is a catalytic amount, e.g., 0.01 to 0.3 equivalents per equivalent of the compound of Formula (II).

[0087] When Reaction 1-4 is an esterification, the reaction conditions are as follows.

[0088] In Reaction 1-4, when L in the compound of Formula (II-a) is alkoxy or aryloxy, esterification can be carried out by reacting the compound of Formula (II) with alcohols or arylhydroxy compounds in the presence of a solvent and a dehydration condensation agent, with the addition of a base as needed. Examples of alcohols used in Reaction 1-4 include methanol and ethanol. Examples of arylhydroxy compounds used in Reaction 1-4 include phenol. The alcohols or arylhydroxy compounds can be used in an amount of 0.5 to 5 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of Formula (II), and an excess amount can be used if no problems occur in the reaction. Examples of dehydration condensation agents used in Reaction 1-4 include those listed in Reaction B above. When the dehydration condensation agent is used in Reaction 1-4, a common additive (e.g., 1-hydroxybenzotriazole (HOBt)) commonly used together with the dehydration condensation agent can be added as needed. The dehydration condensation agent can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II), and the additive can be used in an amount of 0.2 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II). When a base is used together with the dehydration condensation agent in reaction 1-4, the base can be one listed in reaction B above. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (II).

[0089] Furthermore, in Reaction 1-4, when L in the compound of Formula (II-a) is alkoxy, esterification can be carried out by reacting the compound of Formula (II) with an alkyl halide in the presence of a solvent and a base. Examples of alkyl halides used in Reaction 1-4 include methyl iodide and ethyl iodide. The alkyl halide can be used in an amount of 0.5 to 5 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of Formula (II). Bases that can be used in the reaction with the alkyl halide in Reaction 1-4 include those listed in Reaction D above. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of Formula (II).

[0090] When Reaction 1-4 is carbonylation, the reaction conditions are as follows.

[0091] In Reaction 1-4, when L in the compound of Formula (II-a) is alkylcarbonyloxy or arylcarbonyloxy, carbonylation can be carried out by reacting the compound of Formula (II) with a carbonylating agent, typically in the presence of a solvent and a base. Examples of carbonylating agents used in Reaction 1-4 include acetyl chloride, pivaloyl chloride, benzoyl chloride, acetic anhydride, and benzoic anhydride. The carbonylating agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of Formula (II). An excess amount may be used if no problems occur in the reaction. When Reaction 1-4 is carbonylation, the bases listed in Reaction B above can be used. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of Formula (II).

[0092] The solvent in Reaction 1-4 may be any solvent inert to the reaction, and can be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water.

[0093] The reaction temperature in Reaction 1-4 is usually about -50°C to 200°C, preferably about -20°C to 100°C, and the reaction time is usually about 0.1 to 12 hours.

[0094] [Reaction 2-1] to [Reaction 2-4] Reaction 2-1 is a method of reacting a compound of formula (10) with a compound of formula (3) to obtain a compound of formula (11). Reaction 2-2 is a method of reducing a compound of formula (11) to obtain a compound of formula (III). Reactions 2-1 and 2-2 can be carried out consecutively without isolating the compound of formula (11). Reaction 2-3 is a method of reacting a compound of formula (11-a) with a compound of formula (IV) to obtain a compound of formula (11-b). Reaction 2-4 is a method of reacting a compound of formula (V) with a compound of formula (3) to obtain a compound of formula (III).

[0095]

[0096] The symbols in the formula are as defined above.

[0097] Reaction 2-1 can be carried out by adding an acid, a base, or a dehydrating agent, if necessary. Reaction 2-1 can also be carried out in the presence of a solvent. In such cases, the compound of formula (3) in reaction 2-1 can be used in an amount of 1 to 5 equivalents per equivalent of the compound of formula (10), and an excess amount can be used if no problems occur in the reaction.

[0098] The acid in Reaction 2-1 may be either an inorganic acid or an organic acid. Inorganic acids include hydrochloric acid and sulfuric acid, while organic acids include acetic acid, methanesulfonic acid, and paratoluenesulfonic acid. The acid is used in an amount of 0.1 to 10 equivalents relative to 1 equivalent of the compound of Formula (10), and may be used in excess if no problems occur in the reaction. Examples of the base in Reaction 2-1 include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; and alkali metal carboxylates such as sodium acetate and potassium acetate. The base can be used in an amount of 0.5 to 5 equivalents relative to 1 equivalent of the compound of Formula (3).

[0099] Examples of the dehydrating agent in Reaction 2-1 include anhydrous magnesium sulfate, anhydrous sodium sulfate, molecular sieves, etc. The solvent in Reaction 2-1 may be any solvent inert to the reaction, and can be selected from, for example, one or more of aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as acetonitrile; protic polar solvents such as methanol and ethanol; water; and the like.

[0100] The reaction temperature for Reaction 2-1 is usually about -20°C to 200°C, preferably about 0°C to 150°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0101] Reaction 2-1 can also be carried out under general conditions for dehydration condensation between an aldehyde and hydroxylamine or alkoxyamine, for example, in accordance with the method described in HETEROCYCLES, 2009, 78, 463-470, etc. When reaction 2-1 is carried out under general dehydration condensation conditions, the compound of formula (3) in reaction 2-1 can be used in an amount of 0.7 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (10).

[0102] The compound of formula (10) and the compound of formula (3) used in reaction 2-1 can be produced according to known methods, or commercially available products may be used.

[0103] Reaction 2-2 can be carried out usually in the presence of a reducing agent and a solvent, and optionally with the addition of an acid.

[0104] Examples of the reducing agent in Reaction 2-2 include sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and 2-picoline borane complex. The reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (11). The acid to be added may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid, and examples of the organic acid include acetic acid and trifluoroacetic acid. The acid can be used in an amount of 1 to 10 equivalents per equivalent of the compound of formula (11).

[0105] The solvent in Reaction 2-2 may be any solvent inert to the reaction, and can be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; protic polar solvents such as methanol and ethanol; and water.

[0106] The reaction temperature for Reaction 2-2 is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0107] Reaction 2-2 can also be carried out under general conditions for reducing oximes or oxime ethers, for example, according to the method described in HETEROCYCLES, 2009, 78, 463-470.

[0108] The compound of formula (11) used in reaction 2-2 can be produced in accordance with the above reaction 2-1 or a known method, or a commercially available product may be used.

[0109] Reaction 2-3 can be carried out in accordance with Reaction D. The compound of formula (IV) can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (11-a). The base in Reaction 2-3 can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (11-a). The phase transfer catalyst in Reaction 2-3 can be used in an amount of 0.1 to 3 equivalents per equivalent of the compound of formula (11-a).

[0110] Reaction 2-3 can also be carried out under known oxime alkylation conditions, for example, in accordance with the method described in WO 2010 / 049946.

[0111] The compound of formula (11-a) used in reaction 2-3 can be produced in accordance with the above reaction 2-1 or a known method, or a commercially available product may be used. The compound of formula (IV) used in reaction 2-3 can be produced in accordance with a known method, or a commercially available product may be used.

[0112] Reaction 2-4 can be carried out usually in the presence of a base and a solvent, optionally with the addition of a phase transfer catalyst. The compound of formula (3) in Reaction 2-4 can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per equivalent of the compound of formula (V).

[0113] The base in Reaction 2-4 can be selected from, for example, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; organolithium compounds such as n-butyllithium and lithium diisopropylamide; and alkali metal carboxylates such as sodium acetate and potassium acetate. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of Formula (V).

[0114] The solvent in Reaction 2-4 may be any solvent inert to the reaction, and can be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol, and tert-butanol; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and water.

[0115] Examples of the phase transfer catalyst in Reaction 2-4 include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. The phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents per equivalent of the compound of formula (V).

[0116] The reaction temperature for Reaction 2-4 is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 48 hours, preferably about 1 to 24 hours.

[0117] Reaction 2-4 can also be carried out according to known alkylation conditions for alkoxyamines, for example, the method described in Organic Letters, 2004, 6, 2361-2364.

[0118] The compound of formula (V) and the compound of formula (3) used in reaction 2-4 can be produced according to known methods, or commercially available products may be used.

[0119] Compound (I) is useful as an active ingredient of agricultural and horticultural fungicides that can control harmful plant diseases at low doses. Compound (I) can control plant diseases caused by plant pathogenic fungi belonging to the phylum Oomycota, Endomyxa, Olpidiomycota, Ascomycota, Basidiomycota, and Blastocladiomycota, for example. Among these, compound (I) is particularly effective in controlling plant diseases caused by plant pathogenic fungi belonging to the phylum Oomycota, Endomyxa, and Olpidiomycota.

[0120] Plant pathogenic fungi belonging to the above phyla include the following: Oomycota: plant pathogenic fungi belonging to the classes Albuginales, Anisolipidiales, Lagenidiales, Leptomitales, Myzocytiopsidales, Olpidiopsidales, Peronosporales, Pythiales, Rhipidiales, Saprolegniales, and Sclerosporales. Endomyxa: plant pathogenic fungi belonging to the classes Haplosporida, Paradiniida, Paramyxida, Gromiida, Phagomyxida, Plasmodiophorida, and Vampyrellida. Olpidiomycota: plant pathogenic fungi belonging to the classes Olpidiales, etc. Ascomycota: Plant pathogenic fungi belonging to the Cladosporiales, Diaporthales, Erysiphales, Glomerellales, Helotiales, Hypocreales, Magnaporthales, Mycosphaerellales, Myriangiales, Pleosporales, and Venturiales. Basidiomycota: Plant pathogenic fungi belonging to the Agaricales, Cantharellales, Pucciniales, and Ustilaginales. Blastocladiomycota: Plant pathogenic fungi belonging to the Physodermatales class.

[0121] Specific examples of the plant pathogenic fungi include the following: potato or tomato phytophthora blight (Phytophthora infestans), fig phytophthora blight (Phytophthora palmivora), pear or strawberry phytophthora blight (Phytophthora cactorum), wax gourd, pumpkin, bell pepper or chili pepper phytophthora blight (Phytophthora capsici), tomato gray rot (Phytophthora capsici), eggplant or watermelon brown rot (Phytophthora capsici), citrus brown rot (Phytophthora citricola), adzuki bean stem rot (Phytophthora vignae f. sp. adzukicola), edamame stem rot (Phytophthora megasperma var. sojae), onion or rakkyo white rot (Phytophthora Phytophthora spp. such as Pseudoperonospora cubensis (cucumber, pumpkin, melon, zucchini downy mildew) and Pseudoperonospora humuli (hop downy mildew); Plasmopara spp. such as Plasmopara viticola (grape downy mildew) and Plasmopara nivea (honeybee downy mildew); Hyaloperonospora spp. such as Hyaloperonospora brassicae (cabbage or Chinese cabbage downy mildew); Bremia spp. such as Bremia lactucae (lettuce downy mildew); Pythium graminicola (rice seedling damping-off fungus) and Pythium snow rot fungus (wheat snow rot fungus). iwayamai), Chinese cabbage Pythium rot fungus (Pythium aphanidermatum), ginger rhizome rot fungus (Pythium zingiberis), ginger rhizome rot fungus (Pythium ultimum var.Pythium fungi such as Aphanomyces raphani (radish root narrowing fungus) and Aphanomyces cochlioides (spinach root rot fungus); Albugo fungi such as Albugo macrospora (spinach, turnip, radish, or rapeseed white rust fungus), Albugo wasabiae (wasabi white rust fungus), and Albugo ipomoeae-aquaticae (water spinach white rust fungus); Peronospora manshurica (soybean or edamame downy mildew fungus), Peronospora parasitica (broccoli or turnip downy mildew fungus), Peronospora destructor (leek, scallion, or onion downy mildew fungus), and Peronospora farinosa f. sp. Spinaciae), and Peronospora species such as basil downy mildew (Peronospora belbahrii).

[0122] Plasmodiophora species such as Plasmodiophora brassicae, which causes clubroot disease of Chinese cabbage, cabbage, cauliflower, turnip, broccoli, or turnip; Polymyxa species such as Polymyxa betae, which transmits Beet necrotic yellow vein virus; Spongospora species such as Spongospora subterranea, which causes potato powdery scab; and Olpidium species such as Olpidium virulentus, which transmits Mirafiori lettuce big vein virus.

[0123] Erysiphe spp., such as wheat powdery mildew (Erysiphe graminis); Setosphaeria spp., such as corn leaf spot (Setosphaeria turcica); Sphaerotheca spp., such as cucumber powdery mildew (Sphaerotheca fuliginea) and strawberry powdery mildew (Sphaerotheca humuli); Uncinula spp., such as grape powdery mildew (Uncinula necator); Podosphaera spp., such as apple powdery mildew (Podosphaera leucotricha); pea ascochyta (Mycosphaerella pinodes), apple black spot (Mycosphaerella pomi), banana black Sigatoka disease (Mycosphaerella musicola), and persimmon leaf spot (Mycosphaerella Mycosphaerella fungi such as Mycosphaerella nawae, Mycosphaerella fragariae (snake eye fungus of strawberry); Venturia fungi such as Venturia inaequalis (apple scab fungus) and Venturia nashicola (pear scab fungus); Pyrenophora fungi such as Pyrenophora teres (barley net blotch fungus) and Pyrenophora graminea (barley leaf spot fungus); Sclerotinia sclerotiorum (green bean, cucumber, cabbage, Chinese cabbage, chili pepper, bell pepper, or onion), Sclerotinia borealis (wheat snow mold fungus), Sclerotinia minor (tomato), Sclerotinia alfalfa (alfalfa) Sclerotinia species such as Sclerotinia trifoliorum.

[0124] Botryotinia species such as Botryotinia arachidis; Cochliobolus species such as Cochliobolus miyabeanus; Didymella species such as Didymella bryoniae; Gibberella species such as Gibberella fujikuroi; Elsinoe species such as Elsinoe ampelina and Elsinoe fawcettii; Diaporthe species such as Diaporthe citri and Diaporthe sp.; Monilinia mali and Monilinia brevifolia; Monilinia species such as Monilinia fructicola; Glomerella species such as Glomerella cingulata, which causes late rot of grapes. Rhizoctonia species such as rice sheath blight (Rhizoctonia solani); Ustilago species such as wheat naked smut (Ustilago nuda); Puccinia species such as oat crown rust (Puccinia coronata), wheat leaf rust (Puccinia recondita), and wheat stripe rust (Puccinia striiformis); Phakopsora species such as soybean rust (Phakopsora pachyrhizi); Typhula species such as wheat or barley snow mold (Typhula incarnata or Typhula ishikariensis).

[0125] Septoria fungi such as Septoria nodorum and Septoria tritici; Botrytis fungi such as Botrytis cinerea, Botrytis allii, Botrytis squamosa, Botrytis byssoidea, and Botrytis tulipae, which cause leaf blight of onions; Fusarium graminearum, Fusarium wilt of cucumbers; Fusarium graminearum, Fusarium cucumber; ... Botrytis genus; Botrytis genus; Botrytis genus; Botrytis genus; Botrytis genus; Botrytis genus; Botrytis Fusarium fungi such as Pyricularia oxysporum; Pyricularia fungi such as Pyricularia oryzae; Cercospora fungi such as Cercospora beticola (causing brown spot of sugar beet) and Cercospora kakivora (causing corner spot of persimmon); Colletotrichum fungi such as Colletotrichum orbiculare (causing anthracnose of cucumber) and Colletotrichum coffeanum (causing anthracnose of coffee tree); Alternaria alternata apple pathotype, Alternaria alternata Japanese pear pathotype, Alternaria solani (causing summer blight or tomato ring spot), Alternaria brassicae (cabbage or Chinese cabbage black spot), Alternaria Alternaria species such as Alternaria brassicicola, Alternaria porri (onion or leek black spot fungus); Phoma species such as Phoma lingam (cabbage root rot fungus);Pseudocercosporella species such as wheat eyespot fungus (Pseudocercosporella herpotrichoides); Pseudocercospora species such as grape spot fungus (Pseudocercospora vitis); Rhynchosporium species such as barley scald fungus (Rhynchosporium secalis); Cladosporium species such as peach scab fungus (Cladosporium carpophilum); Phomopsis species such as peach phomopsis rot fungus (Phomopsis sp.). Gloeosporium species such as Gloeosporium kaki, Fulvia species such as Fulvia fulva, Corynespora species such as Corynespora cassiicola, Physoderma species such as Physoderma maydis,

[0126] Since compound (I) can control the various plant pathogenic fungi mentioned above, it can preventively or curatively control various diseases. In particular, compound (I) is effective in preventing various diseases that are problematic in the agricultural and horticultural fields, for example, rice diseases such as seedling damping-off caused by Pythium, rice blast caused by Pyricularia, rice seedling disease caused by Fusarium, southern leaf blight caused by Cochliobolus, and sheath blight caused by Rhizoctonia; wheat diseases such as powdery mildew caused by Erysiphe, fusarium head blight or crown rot caused by Fusarium, rust caused by Puccinia, brown snow rot caused by Pythium, naked smut caused by Ustilago, eyespot caused by Pseudocircospora, and leaf blight or stunt blight caused by Septoria. diseases of corn such as Fusarium head blight caused by Fusarium, spot disease caused by Physoderma, rust caused by Puccinia, sooty blight caused by Cetosphaeria, southern leaf blight caused by Cochliobolus, root rot caused by Pythium, and ear smut caused by Ustilago; diseases of grasses such as sugarcane smut caused by Ustilago, leaf burn caused by Stagonospora, rust caused by Puccinia, top rot caused by Gibberella, sooty mildew caused by Caldariomyces, and leaf blight caused by Pseudocircospora; diseases of sugarcane such as Oidium Diseases of legume crops such as powdery mildew caused by fungi, rust caused by Phakopsora, downy mildew caused by Peronospora, late blight or stem rot caused by Phytophthora, anthracnose caused by Colletotrichum, sclerotinia rot caused by Sclerotinia, gray mold caused by Botrytis, root rot or damping-off caused by Fusarium; yellows caused by Fusarium, downy mildew caused by Peronospora or Hyaloperonospora, black spot caused by Alternaria, root rot caused by Phoma, clubroot caused by Plasmodiophora, and root constriction caused by Aphanomyces. diseases of Brassicaceae crops such as Pythium rot caused by Pythium; diseases of Asteraceae crops such as downy mildew caused by Bremia, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotinia rot caused by Sclerotinia, and rust caused by Aesidium; diseases of tomato such as ring spot caused by Alternaria, leaf mold caused by Fluvia, late blight or gray mold caused by Phytophthora, gray mold caused by Botrytis, powdery mildew caused by Oidium, wilt caused by Fusarium, and sooty mold caused by Pseudocircospora;Diseases of Solanaceae crops such as potato diseases such as summer blight caused by Alternaria, late blight or brown rot caused by Phytophthora, sclerotinia rot caused by Sclerotinia, and dry rot caused by Fusarium; diseases of Cucurbitaceae crops such as anthracnose caused by Colletotrichum, powdery mildew caused by Sphaerotheca, vine blight caused by Didymella, downy mildew caused by Pseudoperonospora, late blight or brown rot caused by Phytophthora, brown spot caused by Corynespora, and vine wilt caused by Fusarium; downy mildew caused by Peronospora, Fusarium wilt, and Fusarium wilt. Diseases of Amaryllidaceae and Allium crops, such as late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotinia rot caused by Sclerotinia, and rust caused by Puccinia; diseases of Umbelliferae crops, such as downy mildew caused by Plasmopara, black leaf blight or black spot caused by Alternaria, gray mold caused by Botrytis, sclerotinia rot caused by Sclerotinia, powdery mildew caused by Erysiphe, and spot disease caused by Circospora; diseases of Liliaceae crops, such as leaf blight caused by Botrytis, late blight caused by Phytophthora, and stem blight caused by Phomopsis. Crop diseases: diseases of Polygonaceae crops such as downy mildew caused by Peronospora, powdery mildew caused by Erysiphe, and damping-off caused by Rhizoctonia; diseases of Convolvulaceae crops such as white rust caused by Albugo, fusarium wilt caused by Fusarium, black spot caused by Ceratocystis, and damping-off caused by Streptomyces; root rot caused by Aphanomyces, white rust caused by Albugo, downy mildew caused by Peronospora, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotinia rot caused by Sclerotinia, and oyster disease caused by Eude diseases of Chenopodiaceae crops such as powdery mildew caused by Sphaerotheca spp. and brown spot caused by Circospora; diseases of Vitaceae crops such as black rot caused by Elsinoe spp., late rot caused by Colletotrichum spp., powdery mildew caused by Erysiphe spp., downy mildew caused by Plasmopara spp., gray mold caused by Botrytis spp., brown spot caused by Pseudocircospora spp., and swelling branch disease caused by Diaporthe spp.; diseases of strawberry such as powdery mildew caused by Sphaerotheca spp., gray mold caused by Botrytis spp., anthracnose caused by Glomerella spp., and dry rot caused by Fusarium spp.;Apple diseases such as Monilia disease caused by Monilia fungus, powdery mildew caused by Podosphaera fungus, leaf spot caused by Alternaria fungus, black spot caused by Venturia fungus, anthracnose caused by Glomerella fungus, brown spot caused by Diplocarpon fungus, ring spot caused by Botryosphaeria fungus, sooty spot caused by Zygophiala fungus, sooty spot caused by Gloeodes fungus, and black spot caused by Mycosphaerella fungus; pear diseases such as black spot caused by Venturia fungus, black spot caused by Alternaria fungus, powdery mildew caused by Phyllactinia fungus, late blight caused by Phytophthora fungus, and fruit rot caused by Fusarium fungus; Rosaceae crop diseases such as peach diseases such as brown spot caused by Monilia fungus, black spot caused by Cladosporium fungus, and fomopsis rot caused by fomopsis fungus; It is effective for controlling plant diseases such as citrus diseases such as black spot caused by Diaporthe, common scab caused by Elsinoe, and Fusarium wilt caused by Fusarium; diseases of Ebenaceae crops such as anthracnose caused by Gloeosporium, leaf spot caused by Circospora, powdery mildew caused by Phyllactinia, and sooty spot caused by Zygophiala; diseases of Theaceae crops such as anthracnose caused by Colletotrichum, ring spot caused by Pestalothiopsis, red burn caused by Pseudomonas, and blast caused by Exobasidium; diseases of Zingiberaceae crops such as rhizome rot caused by Pythium; diseases of Cannabaceae crops such as downy mildew caused by Pseudoperonospora; and diseases of Lamiaceae crops such as downy mildew caused by Peronospora.

[0127] Also, diseases of wheat such as Fusarium head blight or crown rot caused by Fusarium, anthracnose caused by Colletotrichum, smut caused by Chiletia, naked smut caused by Ustilago, streak disease caused by Cephalosporium, and leaf spot caused by Septoria; diseases of corn such as southern leaf blight caused by Bipolaris, anthracnose caused by Colletotrichum, and damping-off caused by Fusarium; diseases of grasses such as sugarcane diseases such as red rot caused by Glomerella, black rot caused by Ceratocystis, and downy mildew caused by Sclerospora; purple spot caused by Circospora, and Peronospora. Diseases of legume crops such as soybean diseases such as downy mildew caused by Pora, damping-off caused by Fusarium, ascochyta caused by Septoria, black spot caused by Diaporthe, anthracnose caused by Colletotrichum, and sleeping disease caused by Septogloeum; cabbage diseases such as black spot or black sooty mold caused by Alternaria, downy mildew caused by Peronospora, black spot bacterial disease caused by Pseudomonas, black rot caused by Xanthomonas, and root rot caused by Phoma; radish diseases such as black spot caused by Alternaria, yellows caused by Fusarium, and black rot caused by Xanthomonas; diseases of radish such as black spot caused by Alternaria, black spot caused by Alternaria, and black rot caused by Xanthomonas; diseases of cabbage such as black spot or black sooty mold caused by Alternaria, downy mildew caused by Peronospora, black spot bacterial disease caused by Pseudomonas, black rot caused by Xanthomonas, and root rot caused by Phoma; Diseases of cruciferous crops such as Chinese cabbage diseases such as black spot, black rot caused by Xanthomonas, and yellows caused by Verticillium; tomato diseases such as ring spot caused by Alternaria, canker caused by Clavibacter, and bacterial spot caused by Xanthomonas; eggplant diseases such as brown spot caused by Alternaria and ascochyta caused by Phomopsis; potato diseases such as scab caused by Streptomyces, silver scab caused by Helminthosporium, and powdery scab caused by Spongospora; diseases of solanaceous crops such as black spot caused by Alternaria and bacterial spot caused by Pseudomonas diseases of Cucurbitaceae crops such as cucumber diseases such as brown spot bacterial disease caused by Xanthomonas; diseases of Amaryllidaceae and Allium crops such as black spot caused by Alternaria, gray rot or mycelial rot caused by Botrytis, dry rot caused by Fusarium, downy mildew caused by Peronospora, and white blight or stem rot caused by Phytophthora; diseases of carrots such as black leaf blight or black spot caused by Alternaria and bacterial spot caused by Xanthomonas; diseases of Umbelliferae crops such as celery diseases such as leaf blight caused by Septoria, sclerotinia rot caused by Sclerotinia, and bacterial leaf blight caused by Pseudomonas;It is also effective against seed-borne diseases of Chenopodiaceae crops, such as downy mildew caused by Peronospora, wilt caused by Fusarium, and anthracnose caused by Colletotrichum, which are diseases of spinach.

[0128] Furthermore, it is also effective in controlling soil diseases caused by plant pathogens such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodiophora, and Thielaviopsis.

[0129] Compound (I) can preventively or curatively control the above-mentioned various diseases. Using the test method described in the following examples, certain compounds of the present invention can exhibit excellent preventive or curative control effects at low doses (e.g., 100 ppm, 25 ppm, 12.5 ppm, 6.3 ppm, 3.1 ppm, 1.6 ppm, 0.8 ppm, 0.4 ppm, 0.2 ppm, or 0.1 ppm).

[0130] Compound (I) has excellent rain resistance, residual activity and systemic activity, and therefore, by applying compound (I) to a plant body, harmful fungi on the above-ground parts of the plant can be controlled for a certain period of time.

[0131] In order to control various harmful plant diseases, an effective amount of compound (I) can be applied to plants, plant pathogens, or soil. The effective amount refers to the amount of compound (I) applied that exhibits a control effect against various harmful plant diseases. The plant refers to above-ground parts of plants such as trunks, stems, leaves, flowers, spikes, and fruits, underground parts of plants such as tubers, rhizomes, and roots, and seeds, seedlings, transplants, etc. The soil refers to areas where plants are cultivated, such as agricultural land such as fields, rice paddies, and orchards, and non-agricultural land such as lawns and forests.

[0132] The plant to which compound (I) is applied is not particularly limited as long as it is agriculturally and horticulturally useful, and examples thereof include gramineous crops (rice, wheat, barley, oats, rye, corn, sugarcane, etc.), legume crops (soybean, kidney bean, adzuki bean, pea, peanut, edamame, alfalfa, etc.), Brassicaceae crops (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, rapeseed, rapeseed, Wasabi, etc.), Asteraceae crops (lettuce, burdock, garland chrysanthemum, sunflower, etc.), Solanaceae crops (potato, eggplant, tomato, bell pepper, tobacco, chili pepper, etc.), Cucurbitaceae crops (cucumber, pumpkin, melon, watermelon, wax gourd, zucchini, etc.), Amaryllidaceae Allium crops (leeks, chives, radishes, garlic, onions, scallions, etc.), Umbelliferae crops (celery, carrots, parsley, mitsuba, etc.), Liliaceae crops (lilies, tulips, etc.) crops (such as buckwheat), Convolvulaceae crops (sweet potato, water beet, etc.), Chenopodiaceae crops (spinach, sugar beet, etc.), Vitaceae crops (grapes, etc.), Rosaceae crops (roses, strawberries, apples, pears, peaches, loquats, almonds, etc.), Rutaceae crops (tangerines, lemons, oranges, citrus fruits, etc.), Ebenaceae crops (persimmons, etc.), Mulberry crops (figs, etc.), Theaceae crops (tea, etc.), Oleaceae crops ( Examples of crops that can be cultivated include: Malvaceae crops (cotton, cacao, okra, etc.), Musaceae crops (banana, etc.), Zingiberaceae crops (ginger, ginger, etc.), Cannabaceae crops (hops, etc.), Lamiaceae crops (basil, etc.), Rubiaceae crops (coffee trees, etc.), Bromeliaceae crops (pineapple, bromeliad, etc.), Plumbaceae crops (statice, etc.), Caryophyllaceae crops (carnation, etc.), and Violaceae crops (pansies, etc.).

[0133] The plants include plants bred using genetic engineering or gene editing techniques, such as plants that have been conferred environmental stress resistance, herbicide resistance, pest resistance, disease resistance, etc., or plants that have been modified in terms of growth, fertility traits, product quality, yield, etc.

[0134] Compound (I) is usually mixed with an adjuvant to be formulated and used in various forms such as dust, granules, water dispersible granules, wettable powder, aqueous suspension, oily suspension, water-soluble, emulsion, liquid, paste, aerosol, micro-dust, microcapsule, etc., but as long as it is suitable for the purpose of the present invention, it can be in any formulation form commonly used in the field. The adjuvant used in the formulation can include solid carriers and liquid carriers, and if necessary, surfactants and other formulation adjuvants can also be added.

[0135] Specific examples of the solid carrier include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite, starch, and finely powdered silica.

[0136] Specific examples of the liquid carrier include water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol.

[0137] Examples of the surfactant include fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, alcohol sulfates, alkyl sulfonates, alkylaryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates, alkylaryl phosphates, styrylaryl phosphates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylaryl ether phosphates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl ether phosphates, Examples of the surfactants and spreading agents include anionic surfactants and spreading agents such as ethylene alkylaryl phosphate ester salts and salts of naphthalenesulfonic acid formalin condensates; and nonionic surfactants and spreading agents such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, acetylene glycol, acetylene alcohols, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylaryl ethers, polyoxyethylene glycol alkyl ethers, polyethylene glycol, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid esters.

[0138] Specific examples of other formulation adjuvants include vegetable oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffin, as well as mineral oils; silicones; and xanthan gum.

[0139] As long as the objectives of the present invention are not deviated from, one or more of these adjuvants may be appropriately selected and used. In addition to the adjuvants described above, adjuvants known in the art may also be appropriately selected and used. For example, commonly used adjuvants such as bulking agents, thickeners, antisettling agents, antifreezing agents, dispersion stabilizers, phytotoxicity reducers, and antifungal agents may also be used. The weight ratio of Compound (I) to the various adjuvants is generally 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10. When actually using these formulations, they can be used as is or diluted with a diluent such as water to a predetermined concentration, with various spreading agents (such as surfactants, vegetable oils, and mineral oils) added as necessary.

[0140] The application of compound (I) cannot be unconditionally defined due to differences in weather conditions, formulation, target crop, application time, application location, type and occurrence of harmful plant diseases, etc., but an effective amount of compound (I) can usually be applied by a commonly used application method, i.e., spray treatment, soil treatment, seed treatment, etc. When an effective amount of compound (I) is applied by a commonly used application method, compound (I) can be applied at an active ingredient concentration of 0.1 to 10,000 ppm, preferably 1 to 2,000 ppm, and more preferably 1 to 1,000 ppm. In a commonly used application method, a composition containing compound (I) as an active ingredient (hereinafter also referred to as the present composition) or a diluted version thereof can also be applied. In general, in the case of spray treatment, the appropriate application amount can be about 10 to 100,000 g of the present composition per hectare. In the case of soil treatment, the appropriate application amount is about 0.01 to 1,000 g of the present composition per hectare, and in the case of seed treatment, the appropriate application amount is about 0.001 to 100 g, preferably about 0.01 to 1 g, of the present composition per kg of seeds.

[0141] The spray treatment is a treatment method for controlling plant pathogens by spraying an effective amount of the composition on the surface of the trunk, buds, stems, leaves, flowers, spikes, or fruits of a plant, or on plant pathogens. Examples include foliage spraying and trunk spraying. The soil treatment is a method for treating the soil with the composition to systemically transfer an effective amount of Compound (I) from the roots of the plant to the interior of the plant to protect crops from damage caused by plant pathogens. Examples include drench treatment (drench of the composition into the soil for plant cultivation), soil incorporation treatment (incorporation of the composition into the soil for plant cultivation), planting hole treatment, treatment at the base of the plant or between the plants (spraying or drench), and incorporation treatment into the soil used in culture soil, seedling boxes, seedling trays, paper pots, or seedbeds. The seed treatment is a treatment method for controlling plant pathogens by applying the composition directly to or near the seeds, bulbs, etc. of the crop to protect crops from damage caused by plant pathogens. Examples include painting treatment, dressing treatment, and dipping treatment. Other examples include seedling treatment (drenching or immersion), immersion treatment of bulbs, tubers, bulbs, roots, etc., and hydroponic treatment such as mixing with a hydroponic nutrient solution. Treatment may be performed on the entire plant or on a part of it (stems, leaves, buds, flowers, panicles, fruits, trunks, seeds, bulbs, tubers, bulbs, roots, etc.).

[0142] The present composition can be mixed or used in combination with other ingredients selected from agricultural and horticultural chemicals, fertilizers, and phytotoxicity safeners, and in this case, even more excellent effects and activity may be observed. "Mixed or used in combination" refers to the simultaneous use of the present composition and other ingredients, separate use, or use at intervals. Examples of other agricultural and horticultural chemicals include herbicides, insecticides, miticides, nematicides, soil pesticides, fungicides, antivirals, attractants, antibiotics, plant hormones, and plant growth regulators. In particular, a mixed fungicidal composition containing the present composition and one or more active ingredient compounds of other fungicides may favorably improve the scope of application, timing of application, and control activity. The present composition and the active ingredient compounds of other fungicides may be formulated separately and mixed together at the time of application, or both may be formulated together and used. Such mixed fungicides are also included in the present invention.

[0143] The mixing ratio of compound (I) and the active ingredient compounds of other fungicides cannot be generally determined due to differences in weather conditions, formulation, target crop, application time, application location, type and occurrence of harmful plant diseases, etc., but can generally be 1:300 to 300:1, preferably 1:100 to 100:1, by weight. The appropriate application amount is 0.1 to 70,000 g, preferably 1 to 30,000 g, of the total active ingredient compounds per hectare. The present invention also includes a method for controlling harmful plant diseases by applying such a mixed fungicidal composition.

[0144] When applying the present composition, other agricultural and horticultural chemicals such as fungicides, insecticides, acaricides, nematicides, soil pesticides, antiviral agents, attractants, herbicides, plant growth regulators, etc. may also be used in combination.

[0145] Among the above-mentioned other agricultural and horticultural agents, the active ingredient compounds (common names) of the fungicides can be appropriately selected, for example, from the following compound group. Even if not specifically stated, when these compounds have salts, alkyl esters, optical isomers, and other structural isomers, these are of course included.

[0146] Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Triazolobenzothiazole compounds such as tricyclazole; Pyridinamine compounds such as fluazinam;Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, fluconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate azole compounds such as fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipfentrifluconazole, and mefentrifluconazole;

[0147] Quinoxaline compounds such as chinomethionate; Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, and thiram; Organochlorine compounds such as phthalide, chlorothalonil, and quintozene; Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, and fuberiazole; Cyanoacetamide compounds such as cymoxanil; Acylamino acid compounds such as metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, ofurace, benalaxyl, benalaxyl-M (also known as chiralaxyl or chiralaxyl), furalaxyl, and valifenalate; anilide compounds such as cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, and pyraziflumid;

[0148] Sulfamide compounds such as dichlofluanid; Copper compounds such as cupric hydroxide, organocopper (oxine copper), anhydrous copper sulfate, copper nonylphenolsulfonate, 8-hydroxyquinoline copper, and dodecylbenzenesulfonate bisethylenediamine copper complex(II) (also known as DBEDC); Organophosphate compounds such as fosetyl aluminum, tolclofos-methyl, edifenphos, and iprobenfos; Phthalimides such as captan, captafol, and folpet; Dicarboximides such as procymidone, iprodione, and vinclozolin; benzanilide compounds such as flutolanil, mepronil, benodanil, and flufenoxadiazam; amide compounds such as carpropamid, diclocymet, silthiofam, and fenoxanil; pyrazolecarboxamide compounds such as benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, sedaxane, isoflucipram, inpyrfluxam, pyrapropoyne, and fenopyramid;

[0149] Benzamide compounds such as fluopicolide, fluopyram, zoxamide, and fluopimomide; Furanilide compounds such as fenfuram; Thiophenamide compounds such as isofetamide; Piperazine compounds such as triforine; Pyridine compounds such as pyrifenox, pyrisoxazole, and aminopyrifen; Pyrimidine compounds such as fenarimol, ferimzone, nuarimol, and flumethylsulforim; Piperidine compounds such as fenpropidin; Morpholine compounds such as fenpropimorph and tridemorph; Organotin compounds such as triphenyltin hydroxide and triphenyltin acetate; urea compounds such as pensicuron; carboxylic acid amide compounds such as dimethomorph, flumorph, pyrimorph, iprovalicarb, benthiavalicarb-isopropyl, and mandipropamid; phenylcarbamate compounds such as diethofencarb; cyanopyrrole compounds such as fludioxonil and fenpiclonil;

[0150] Strobilurin compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, phenaminestrobin, flufenoxystrobin, triclopyricarb, and mandestrobin; oxazole compounds such as famoxadone and oxathiapiprolin; Thiazolecarboxamide compounds such as ethaboxam; imidazolinone compounds such as fenamidone; benzenesulfonamide compounds such as flusulfamide; oxime ether compounds such as cyflufenamid; anthraquinone compounds such as dithianon; crotonic acid compounds such as meptyldinocap; antibiotics such as validamycin, kasugamycin, streptomycin, and polyoxins;

[0151] Guanidine compounds such as iminoctadine, dodine, and guazatine; Aliphatic nitrogen compounds such as butylamine and seboctylamine; Quinoline compounds such as tebufloquin, quinoxyfen, quinofumelin, ipflufenoquin, and feneptamidoquin; Thiazolidine compounds such as flutianil; Carbamate compounds such as propamocarb hydrochloride, pyribencarb, and tolprocarb; Tetrazole compounds such as picarbutrazox and methyltetraprole; Sulfonamide compounds such as amisulbrom and cyazofamid; Allyl phenyl ketone compounds such as metrafenone and pyriophenone; Benzothiazole compounds such as probenazole and dichlobentiazox; Phenylpyrazole compounds such as fenpyrazamine; Dithiolane compounds such as isoprothiolane; Picolinamide compounds such as fenpicoxamid and florylpicoxamid;

[0152] Sulfur-based compounds such as sulfur and lime sulfur; other compounds such as pyroquilon, diclomezine, chloropicrin, dazomet, metam sodium, proquinazid, spiroxamine, and dipymetitrone; microbial disinfectants such as Bacillus amylolipoides strain QST713, Bacillus amylolipoides strain FZB24, Bacillus amylolipoides strain MBI600, Bacillus amylolipoides strain D747, Pseudomonas fluorescens, Bacillus subtilis, and Trichoderma atroviride SKT-1; and plant extracts such as tea tree oil.

[0153] Among the above-mentioned other agricultural and horticultural agents, the active ingredient compounds (common names) of the insecticides, nematicides, miticides, or soil pesticides can be appropriately selected, for example, from the following compound groups. Even if not specifically stated, when these compounds have salts, alkyl esters, optical isomers, and other structural isomers, these are of course also included.

[0154] Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenylphenylphosphonothioate), diazinon (diazinon), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), acephate (acephate), prothiofos (prothiofos), fosthiazate (fosthiazate), cadusafos (cadusafos), disulfoton (disulfoton), isoxathion (isoxathion), isofenphos (isofenphos), ethion (ethion), etrimfos (etrimfos), quinalphos (quinalphos), dimethylvinphos (dimethylvinphos), dimethoate (dimethoate), sulprofos (sulprofos), thiometon (thiometon), vamidothion (vamidothion), pyraclofos (pyraclofos), pyridaphenthion (pyridaphenthion), pirimiphos-methyl (pirimiphos-methyl), propaphos (propaphos), phosalone (phosalone), formothion (for organophosphate ester compounds such as mothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, oxydeprofos (also known as ESP), azinphos-methyl, fenthion, heptenophos, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, and phorate;

[0155] Carbamate compounds such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, 3,5-xylyl methylcarbamate (XMC), and fenothiocarb; cartap, thiocyclam, thiocyclam oxalate, and thiocyclam hydrochloride; Nereistoxin derivatives such as thiosultap, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan; organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, and methoxychlor; organometallic compounds such as fenbutatin oxide and cyhexatin;

[0156] Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin, deltamethrin, cyhalothrin, gamma-cyhalothrin mma-cyhalothrin, lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, etofenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvalinate fluvalinate, cycloprothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin, allethrin, tau-fluvalinate Tau-fluvalinate, tralomethrin, profluthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin,Pyrethroid compounds such as silafluofen and chloroprallethrin;

[0157] Benzoylurea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron, noviflumuron, fluazuron, and flufenoxuron; juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb, and diofenolan; pyridazinone compounds such as pyridaben; Pyrazole compounds such as fenpyroximate, fipronil, ethiprole, acetoprole, pyrafluprole, pyriprole, cyenopyrafen, and flufiprole; Pyrazolecarboxamide compounds such as piflubumide, tebufenpyrad, tolfenpyrad, and dimpropyridaz; pyridylpyrazole compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, tyclopyrazoflor, fluchlordiniliprole, and thioantraniliprole;

[0158] Neonicotinoid compounds such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran, and nithiazine; hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, and halofenozide; pyridine compounds such as pyridalyl and flonicamid; tetronic acid compounds such as spirodiclofen, spiromesifen, and spirobudifen; Tetramic acid compounds such as spirotetramat and spiropidione; Strobilurin compounds such as fluacrypyrim, pyriminostrobin and flupyroxystrobin; Pyrimidinamine compounds such as flufenerim and pyrimidifen; Organic sulfur compounds such as malathion; Triazine compounds such as cyromazine; Hydrazone compounds such as hydramethylnon; Diamide compounds such as flubendiamide, broflanilide, cyhalodiamide, pioxaniliprole and piperflanilide;

[0159] Thiourea compounds such as diafenthiuron and chloromethiuron; Formamidine compounds such as amitraz, chlordimeform and chloromebuform; Pyridine azomethine compounds such as pymetrozine and pyrifluquinazone; Isoxazoline compounds such as afoxolaner, fluralaner, fluxametamide, sarolaner and isoflualanam;Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene, benclothiazol, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, sulfuramid, hydramethylnon, metaldehyde, sulfoxaflor, and fluensulfone. Compounds such as sulfone, verbutin, dichloromezotiaz, triflumezopyrim, fluhexafon, tioxazafen, afidopyropen, flometoquin, flupyradifurone, fluazaindolizine, acinonapyr, benzpyrimoxan, flupyrimin, oxazosulfyl, sulfiflumin, bisulfufen, cybenzoxasulfyl, galquin, vedescana, tiapyrachlor, bentiofluorin, and the like;

[0160] The present composition may also be applied in combination with the following compounds: microbial pesticides such as crystal protein toxins produced by Bacillus thuringiensis, such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, and Bacillus thuringiensis tenebrionis, insect pathogenic virus agents, insect pathogenic fungi agents, and nematode pathogenic fungi agents; antibiotics and semi-synthetic antibiotics, such as abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, and spinetoram; Natural products such as azadirachtin, rotenone, and ryanodine; repellents such as deet; physical control agents such as paraffin oil and mineral oil; and RNAi pesticides such as ledprona and vadescana.

[0161] Desirable aspects of the present invention are as follows. However, the present invention is not limited to these. [1] A compound represented by formula (I) or a salt thereof. [2] A compound according to the above [1] or a salt thereof, wherein the compound of formula (I) is an N-(cyclo)alkoxyamide compound of formula (IA) or an N-alkynyloxyamide compound of formula (IB). [3] A compound according to the above [1] or a salt thereof, wherein the compound of formula (I) is an N-(cyclo)alkoxyamide compound of formula (IA). [4] A compound according to the above [1] or a salt thereof, wherein the compound of formula (I) is an N-alkynyloxyamide compound of formula (IB).

[0162] [5] X １[6] The compound or salt thereof according to the above [1], wherein X is a fluorine atom, a chlorine atom, or a bromine atom. １ [7] The compound or salt thereof according to the above [1], wherein X is a fluorine atom or a chlorine atom. １ [8] The compound or salt thereof according to the above [1], wherein X is a fluorine atom or a bromine atom. １ [9] The compound or salt thereof according to the above [1], wherein X is a chlorine atom or a bromine atom. １

[10] The compound or salt thereof according to the above [1], wherein X is a fluorine atom. １

[11] The compound or salt thereof according to the above [1], wherein X is a chlorine atom. １ is a bromine atom, or a salt thereof, according to [1] above.

[0163]

[12] R １ But, T １ (C １ -C ４ )-alkyl, (C ３ -C ４ )-cycloalkyl, (C ３ -C ５ )-alkenyl, or (C ３ -C ５

[13] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R １ However, (C １ -C ４ )-alkyl, (C ３ -C ４ )-cycloalkyl, or (C ３ -C ５

[14] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is )-alkynyl. １

[15] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl, ethyl, normal propyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, propargyl, allyl, methylthiomethyl, cyanomethyl, 2-methoxyethyl, 2,2-difluoroethyl, or methoxycarbonylmethyl. １

[16] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl, ethyl, cyclopropyl, or propargyl. １

[17] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl, ethyl, or cyclopropyl. １

[18] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl, ethyl, or propargyl. １

[19] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl or ethyl. １

[20] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl or cyclopropyl. １

[21] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl or propargyl. １

[22] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is methyl. １

[23] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is ethyl. １

[24] The compound or salt thereof according to any one of [1], [5] to

[11] , wherein R is cyclopropyl. １ The compound or salt thereof according to any one of [1], [5] to

[11] , wherein is propargyl.

[0164]

[25] Y １ is a hydrogen atom, a halogen, (C １ -C ６ )-alkyl, (C １ -C ６

[26] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is 1-haloalkyl, nitro, or cyano. １ is halogen, (C １ -C ３ )-alkyl, (C １ -C ３

[27] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is 1-haloalkyl, nitro, or cyano. １

[28] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, methyl, trifluoromethyl, difluoromethyl, nitro, or cyano. １

[29] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is a fluorine atom, a chlorine atom, a bromine atom, methyl, trifluoromethyl, difluoromethyl, nitro, or cyano. １

[30] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is a fluorine atom, a chlorine atom, a bromine atom, or methyl. １

[31] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is a fluorine atom. １

[32] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is a chlorine atom. １

[33] The compound or salt thereof according to any one of [1], [5] to

[24] , wherein Y is a bromine atom. １ The compound or salt thereof according to any one of [1], [5] to

[24] , wherein is methyl.

[0165]

[34] Y ２ is halogen, (C １ -C ６

[35] The compound or salt thereof according to any one of [1], [5] to

[33] , wherein Y is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 2 ２ is a fluorine atom, a chlorine atom, (C １ -C ３

[36] The compound or salt thereof according to any one of [1], [5] to

[33] , wherein Y is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 2 ２

[37] The compound or salt thereof according to any one of [1], [5] to

[33] , wherein Y is a fluorine atom, a chlorine atom, a methyl, or a hydrogen atom. ２

[38] The compound or salt thereof according to any one of [1], [5] to

[33] , wherein Y is a fluorine atom or a hydrogen atom. ３ is halogen, (C １ -C ６

[39] The compound or salt thereof according to any one of [1], [5] to

[37] , wherein Y is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 2 ３ is a fluorine atom, a chlorine atom, (C １ -C ３

[40] The compound or salt thereof according to any one of [1], [5] to

[37] , wherein Y is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 39, 38, 39, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 6 ３

[41] The compound or salt thereof according to any one of [1], [5] to

[37] , wherein Y is a fluorine atom, a chlorine atom, a methyl, or a hydrogen atom. ３ is a fluorine atom or a hydrogen atom, or a salt thereof according to any one of [1], [5] to

[37] .

[0166]

[42] Y ４

[43] The compound or salt thereof according to any one of [1], [5] to

[41] , wherein Y is a halogen or a hydrogen atom. ４

[44] The compound or salt thereof according to any one of [1], [5] to

[41] , wherein Y is a fluorine atom, a chlorine atom, or a hydrogen atom. ４

[45] The compound or salt thereof according to any one of [1], [5] to

[41] , wherein Y is a fluorine atom or a hydrogen atom. ５

[46] The compound or salt thereof according to any one of [1], [5] to

[44] , wherein Y is a halogen or a hydrogen atom. ５

[47] The compound or salt thereof according to any one of [1], [5] to

[44] , wherein Y is a fluorine atom, a chlorine atom, or a hydrogen atom. ５

[48] ​​The compound or salt thereof according to any one of [1], [5] to

[44] , wherein Y is a fluorine atom or a hydrogen atom. ５ The compound or salt thereof according to any one of [1], [5] to

[44] , wherein

[0167]

[49] An N-(cyclo)alkoxyamide compound represented by formula (IA) or a salt thereof.

[50] Y １ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６

[51] The N-(cyclo)alkoxyamide compound or salt thereof according to

[49] above, wherein Y is 1-haloalkyl, nitro, or cyano. １

[52] The N-(cyclo)alkoxyamide compound or a salt thereof according to

[49] above, wherein Y is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, methyl, trifluoromethyl, difluoromethyl, nitro, or cyano. １

[53] The N-(cyclo)alkoxyamide compound or a salt thereof according to

[49] above, wherein Y is a fluorine atom, a chlorine atom, a bromine atom, methyl, trifluoromethyl, difluoromethyl, nitro, or cyano. ２Ａ

[52] The N-(cyclo)alkoxyamide compound or a salt thereof according to any one of

[49] to

[52] above, wherein is a hydrogen atom, a fluorine atom, or a chlorine atom.

[0168]

[54] Y ２Ａ

[55] The N-(cyclo)alkoxyamide compound or salt thereof according to any one of

[49] to

[52] above, wherein Y is a hydrogen atom or a fluorine atom. ３Ａ

[56] The N-(cyclo)alkoxyamide compound or salt thereof according to any one of

[49] to

[54] above, wherein Y is a hydrogen atom, a fluorine atom, or a chlorine atom. ３Ａ

[57] The N-(cyclo)alkoxyamide compound or salt thereof according to any one of

[49] to

[54] above, wherein Y is a hydrogen atom or a fluorine atom. ４Ａ

[58] The N-(cyclo)alkoxyamide compound or salt thereof according to any one of

[49] to

[56] above, wherein R is a hydrogen atom or a fluorine atom. １Ａ

[59] The N-(cyclo)alkoxyamide compound or salt thereof according to any one of

[49] to

[57] above, wherein R is methyl, ethyl, normal propyl, isopropyl, tertiary butyl, cyclopropyl, or cyclobutyl.１Ａ

[58] The N-(cyclo)alkoxyamide compound or a salt thereof according to any one of

[49] to

[57] above, wherein is methyl, ethyl, or cyclopropyl.

[0169]

[60] An N-alkynyloxyamide compound represented by formula (IB) or a salt thereof. ５

[62] The N-alkynyloxyamide compound or salt thereof according to

[60] above, wherein Y is a hydrogen atom. １ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６

[63] The N-alkynyloxyamide compound or salt thereof according to

[60] or

[61] , wherein Y is 1-haloalkyl, nitro, or cyano. １

[64] The N-alkynyloxyamide compound or salt thereof according to

[60] or

[61] above, wherein Y is a fluorine atom, a chlorine atom, a bromine atom, methyl, difluoromethyl, nitro, or cyano. ２

[64] The N-alkynyloxyamide compound or a salt thereof according to any one of

[60] to

[63] above, wherein is a hydrogen atom or a halogen.

[0170]

[65] Y ２

[66] The N-alkynyloxyamide compound or a salt thereof according to any one of

[60] to

[63] , wherein Y is a hydrogen atom or a fluorine atom. ３

[67] The N-alkynyloxyamide compound or salt thereof according to any one of

[60] to

[65] above, wherein Y is a hydrogen atom or a halogen atom. ３

[68] The N-alkynyloxyamide compound or salt thereof according to any one of

[60] to

[65] above, wherein Y is a hydrogen atom or a fluorine atom. ４

[69] The N-alkynyloxyamide compound or salt thereof according to any one of

[60] to

[67] above, wherein Y is a hydrogen atom or a halogen atom. ４

[70] The N-alkynyloxyamide compound or salt thereof according to any one of

[60] to

[67] above, wherein X is a hydrogen atom or a fluorine atom. １

[69] The N-alkynyloxyamide compound or salt thereof according to any one of

[60] to

[69] above, wherein is a fluorine atom, a chlorine atom, or a bromine atom.

[0171]

[71] An agricultural and horticultural fungicide containing, as an active ingredient, the compound or salt thereof according to any one of [1] to

[70] above.

[72] A method for controlling harmful plant diseases, which comprises applying an effective amount of the compound or salt thereof according to any one of [1] to

[70] above to plants, plant pathogens, or soil.

[0172] Examples of the present invention will be described below, but the present invention is not limited to these. The melting point, which is a physical property value of the compound of the present invention, was measured using a Buchi M-565. １ H-NMR spectrum data was measured in a measurement solvent using a JEOL JNM-ECX (500 MHz) or a Bruker AVANCE III HD (300 MHz) (H-nuclear magnetic resonance spectroscopy). The measurement solvent may contain tetramethylsilane (TMS) as an internal standard. In this specification, room temperature refers to approximately 10 to 30°C.

[0173] [Synthesis Examples] Synthesis Example 1: Synthesis of 2-amino-4-bromo-N-(2-chlorobenzyl)-N-methoxythiazole-5-carboxamide (Compound No. A-94) (1) 2-Chlorobenzyl bromide (543 mg) and O-methylhydroxylamine hydrochloride (662 mg) were mixed in N,N-dimethylformamide (10 mL), and diisopropylethylamine (2.31 mL) was added to the resulting mixture at room temperature, followed by stirring at 50°C for 5 hours. After allowing to cool to room temperature, the reaction solution was quenched by adding water. Ethyl acetate and heptane were successively added to the quenched reaction solution, and the aqueous layer was extracted with an ethyl acetate-heptane mixed solution. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to give N-(2-chlorobenzyl)-O-methylhydroxylamine (266 mg) as an oil. 1 The H-NMR spectrum data is as follows: 1H NMR (CDCl3 / 300MHz):δ(ppm)= 7.42-7.36 (m, 2H), 7.27-7.22 (m, 2H), 5.91 (brs, 1H), 4.18 (s, 2H), 3.54 (s, 3H).

[0174] (2) To a solution of tert-butyl (4-bromo-5-formylthiazol-2-yl)carbamate (9.7 g) synthesized based on Example 18, Step F described on page 56 of WO 2012 / 008999 in tert-butanol (310 mL), an aqueous solution (20 mL) of sodium dihydrogen phosphate (11.3 g) was added at room temperature, and the mixture was stirred to obtain a mixture. 2-Methyl-2-butene (43 mL) was added to the resulting mixture. After 15 minutes, an aqueous solution (50 mL) of sodium chlorite (21.4 g, 80%) was added, and the mixture was stirred for 3.5 hours. The reaction solution was acidified with hydrochloric acid, and then extracted with ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting solid was dissolved in saturated aqueous sodium bicarbonate, and the aqueous layer was washed with ethyl acetate. Hydrochloric acid was added to the aqueous layer washed with ethyl acetate to adjust the acidity. Ethyl acetate was added to the aqueous layer adjusted to acidity, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-bromothiazole-5-carboxylic acid (9.2 g) as a white solid. 1 The H-NMR spectrum data is as follows: 1 H NMR (DMSO-d6 / 300MHz): δ(ppm)= 13.36 (brs, 1H), 12.18 (s, 1H), 1.49 (s, 9H).

[0175] (3) To a solution of 2-[(tert-butoxycarbonyl)amino]-4-bromothiazole-5-carboxylic acid (339 mg) in tetrahydrofuran (10 mL), oxalyl chloride (166 mg) and a catalytic amount of N,N-dimethylformamide were added under ice cooling, and the mixture was stirred under a nitrogen atmosphere. After 10 minutes, the temperature was raised to room temperature and the mixture was stirred for an additional 40 minutes. The reaction solution was concentrated under reduced pressure to give 2-[(tert-butoxycarbonyl)amino]-4-bromothiazole-5-carboxylic acid chloride. Tetrahydrofuran (5 mL) was added to dissolve the obtained acid chloride, and then a solution of N-(2-chlorobenzyl)-O-methylhydroxylamine (150 mg) in tetrahydrofuran (5 mL) and diisopropylethylamine (0.31 mL) were added sequentially at room temperature, and the mixture was stirred at 50°C for 1 hour and 45 minutes. After cooling to room temperature, the reaction solution was quenched with saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to give amorphous tert-butyl {4-bromo-5-[(2-chlorobenzyl)(methoxy)carbamoyl]thiazol-2-yl}carbamate (376 mg). 1 The H-NMR spectrum data is as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 12.12 (brs, 1H), 7.51-7.49 (m, 1H), 7.37-7.35 (m, 3H), 5.02 (s, 2H), 3.67 (s, 3H), 1.48 (s, 9H).

[0176] (4) Trifluoroacetic acid (1.2 mL) was added to a solution of tert-butyl {4-bromo-5-[(2-chlorobenzyl)(methoxy)carbamoyl]thiazol-2-yl}carbamate (376 mg) in dichloromethane (6 mL), and the mixture was stirred overnight under reflux. After cooling to room temperature, saturated aqueous sodium bicarbonate solution was slowly added to the reaction solution to adjust the reaction solution to basicity. The aqueous layer of the reaction solution adjusted to basicity was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (208 mg) as a solid. 1 The H-NMR spectrum data and melting point are as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 7.96 (brs, 2H), 7.49-7.46 (m, 1H), 7.36-7.29 (m, 3H), 4.96 (s, 2H), 3.65 (s, 3H). Melting point: 184.8℃

[0177] Synthesis Example 2: Synthesis of 2-amino-4-bromo-N-(4-fluoro-2-methylbenzyl)-N-methoxythiazole-5-carboxamide (Compound No. A-105) (1) To a solution of O-methylhydroxylamine hydrochloride (302 mg) in methanol (4 mL), triethylamine (0.5 mL) was added at 0°C, and the mixture was stirred to obtain a mixture. To the obtained mixture, a solution of 4-fluoro-2-methylbenzaldehyde (500 mg) in methanol (6 mL) and acetic acid (1 mL) were added sequentially, and after 30 minutes, the mixture was warmed to room temperature. After 3.5 hours, 2-picoline borane (774 mg) was added at 0°C, and after an additional 15 minutes, 3N aqueous hydrochloric acid (6 mL) was added, and the mixture was stirred for 2.5 hours to obtain a reaction solution. A saturated aqueous sodium bicarbonate solution was added to the reaction solution to adjust it to basicity, and then methanol was distilled off. Ethyl acetate was added to the residue, and the mixture was extracted. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain oily N-(4-fluoro-2-methylbenzyl)-O-methylhydroxylamine (392 mg). 1 The H-NMR spectrum data is as follows: 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.26-7.21 (m, 1H), 6.90-6.82 (m, 2H), 5.59 (brs, 1H), 4.03 (s, 2H), 2.35 (s, 3H), 2.39 (s, 3H).

[0178] (2) To a solution of 2-[(tert-butoxycarbonyl)amino]-4-bromothiazole-5-carboxylic acid (339 mg) in tetrahydrofuran (10 mL), oxalyl chloride (0.11 mL) and a catalytic amount of N,N-dimethylformamide were added under ice cooling, and the mixture was stirred under a nitrogen atmosphere. After 10 minutes, the temperature was raised to room temperature and the mixture was stirred for an additional 40 minutes. The reaction solution was concentrated under reduced pressure to give 2-[(tert-butoxycarbonyl)amino]-4-bromothiazole-5-carboxylic acid chloride. Tetrahydrofuran (5 mL) was added to dissolve the obtained acid chloride, and then a solution of N-(4-fluoro-2-methylbenzyl)-O-methylhydroxylamine (148 mg) in tetrahydrofuran (5 mL) and diisopropylethylamine (0.31 mL) were added at room temperature, and the mixture was stirred at 50°C for 1 hour and 45 minutes. After cooling to room temperature, the reaction solution was quenched with saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to give amorphous tert-butyl {4-bromo-5-[(4-fluoro-2-methylbenzyl)(methoxy)carbamoyl]thiazol-2-yl}carbamate (370 mg). 1 The H-NMR spectrum data is as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 12.10 (brs, 1H), 7.24 (dd, 1H), 7.10-6.99 (m, 2H), 4.90 (s, 2H), 3.62 (s, 3H), 2.31 (s, 3H), 1.48 (s, 9H).

[0179] (3) Trifluoroacetic acid (1.2 mL) was added to a solution of tert-butyl {4-bromo-5-[(4-fluoro-2-methylbenzyl)(methoxy)carbamoyl]thiazol-2-yl}carbamate (370 mg) in dichloromethane (6 mL), and the mixture was stirred overnight under reflux. After cooling to room temperature, saturated aqueous sodium bicarbonate solution was slowly added to the reaction solution to adjust the reaction solution to basicity. The aqueous layer of the reaction solution adjusted to basicity was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (262 mg) as a solid. 1 The H-NMR spectrum data and melting point are as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 7.93 (brs, 2H), 7.21 (dd, 1H), 7.08-6.97 (m, 2H), 4.84 (s, 2H), 3.59 (s, 3H), 2.29 (s, 3H). Melting point: 164.0℃

[0180] Synthesis Example 3: Synthesis of 2-amino-4-chloro-N-(2-fluorobenzyl)-N-(2-propynyloxy)thiazole-5-carboxamide (Compound No. B-55) (1) 2-Fluorobenzyl bromide (500 mg) and O-2-propynylhydroxylamine hydrochloride (754 mg) synthesized based on Synthetic Example 1-2 described on page 16 of U.S. Patent Application Publication No. 2014 / 0378399 were mixed with N,N-dimethylformamide (10 mL), and diisopropylethylamine (2.31 mL) was added to the resulting mixture at room temperature, followed by stirring at 50°C for 5 hours. After allowing to cool to room temperature, the reaction solution was quenched by adding water. Ethyl acetate and heptane were added sequentially to the quenched reaction solution, and the aqueous layer of the reaction solution was extracted with an ethyl acetate-heptane mixed solution. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain oily N-(2-fluorobenzyl)-O-(2-propynyl)hydroxylamine (69 mg). 1 The H-NMR spectrum data is as follows: 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.38 (dt, 1H), 7.31-7.24 (m, 1H), 7.11 (dt, 1H), 7.08-7.02 (m, 1H), 6.02 (t, 1H), 4.29 (d, 2H), 4.18 (d, 2H), 2.41 (t, 1H).

[0181] (2) To a tetrahydrofuran (5 mL) solution of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid (128 mg), synthesized based on Experimental 5.1.10 described on page 6177 of Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182, oxalyl chloride (0.05 mL) and a catalytic amount of N,N-dimethylformamide were added under ice cooling, and the mixture was stirred under a nitrogen atmosphere. After 10 minutes, the temperature was raised to room temperature and further stirred for 1 hour. The reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid chloride. Tetrahydrofuran (2 mL) was added to the obtained acid chloride to dissolve it, and then a solution of N-(2-fluorobenzyl)-O-2-propynylhydroxylamine (69 mg) in tetrahydrofuran (3 mL) and diisopropylethylamine (0.13 mL) were added sequentially at room temperature, and the mixture was stirred at 50°C for 2 hours. After cooling to room temperature, the reaction solution was quenched with saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain amorphous tert-butyl {4-chloro-5-[(2-fluorobenzyl)(2-propynyloxy)carbamoyl]thiazol-2-yl}carbamate (87 mg). This product 1 The H-NMR spectrum data is as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 12.09 (brs, 1H), 7.41-7.33 (m, 2H), 7.25-7.18 (m, 2H), 5.03 (s, 2H), 4.71 (d, 2H), 3.66 (t, 1H), 1.48 (s, 9H).

[0182] (3) Trifluoroacetic acid (0.3 mL) was added to a solution of tert-butyl {4-chloro-5-[(2-fluorobenzyl)(2-propynyloxy)carbamoyl]thiazol-2-yl}carbamate (87 mg) in dichloromethane (1.5 mL), and the mixture was stirred overnight under reflux. After cooling to room temperature, saturated aqueous sodium bicarbonate solution was slowly added to the reaction solution to adjust the reaction solution to basicity. The aqueous layer of the reaction solution adjusted to basicity was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (55 mg) as a solid. 1 The H-NMR spectrum data and melting point are as follows: 1 H NMR (DMSO-d6 / 300MHz): δ(ppm)= 7.98 (brs, 2H), 7.40-7.29 (m, 2H), 7.23-7.16 (m, 2H), 4.97 (s, 2H), 4.64 (d, 2H), 3.68 (t, 1H). Melting point: 154.1℃

[0183] Synthesis Example 4: Synthesis of 2-amino-4-chloro-N-(2,4-difluorobenzyl)-N-(2-propynyloxy)thiazole-5-carboxamide (Compound No. B-57) (1) To a solution of O-2-propynylhydroxylamine hydrochloride (389 mg) in methanol (4 mL), triethylamine (0.5 mL) was added at 0°C, and the mixture was stirred to obtain a mixture. To the obtained mixture, a solution of 2,4-difluorobenzaldehyde (514 mg) in methanol (6 mL) and acetic acid (1 mL) were added sequentially, and after 30 minutes, the mixture was warmed to room temperature. After 3.5 hours, the mixture was cooled to 0°C, and 2-picoline borane (967 mg) was added. After an additional 15 minutes, 3N aqueous hydrochloric acid solution (7.2 mL) was added, and the mixture was stirred for 3 hours to obtain a reaction solution. A saturated aqueous sodium bicarbonate solution was added to the reaction solution to make it basic, and then methanol was distilled off. Ethyl acetate was added to the residue, and extraction was performed. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain oily N-(2,4-difluorobenzyl)-O-2-propynylhydroxylamine (471 mg). 1 The H-NMR spectrum data is as follows: 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.40-7.32 (m, 1H), 6.89-6.77 (m, 2H), 5.96 (t, 1H), 4.27 (d, 2H), 4.13 (d, 2H), 2.41 (t, 1H).

[0184] (2) To a solution of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid (291 mg) in tetrahydrofuran (10 mL), oxalyl chloride (0.11 mL) and a catalytic amount of N,N-dimethylformamide were added under ice cooling, and the mixture was stirred under a nitrogen atmosphere. After 10 minutes, the temperature was raised to room temperature and the mixture was stirred for an additional 1 hour. The reaction solution was concentrated under reduced pressure to give 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid chloride. Tetrahydrofuran (5 mL) was added to dissolve the obtained acid chloride, and then a solution of N-(2,4-difluorobenzyl)-O-2-propynylhydroxylamine (172 mg) in tetrahydrofuran (5 mL) and diisopropylethylamine (0.30 mL) were added sequentially at room temperature, and the mixture was stirred at 50°C for 2 hours. After cooling to room temperature, the reaction solution was quenched with saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to give amorphous tert-butyl {4-chloro-5-[(2,4-difluorobenzyl)(2-propynyloxy)carbamoyl]thiazol-2-yl}carbamate (204 mg). 1 The H-NMR spectrum data is as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 12.09 (brs, 1H), 7.46-7.38 (m, 1H), 7.31-7.24 (m, 1H), 7.14-7.08 (m, 1H), 5.00 (s, 2H), 4.71 (d, 2H), 3.66 (t, 1H), 1.48 (s, 9H).

[0185] (3) Trifluoroacetic acid (0.69 mL) was added to a solution of tert-butyl {4-chloro-5-[(2,4-difluorobenzyl)(2-propynyloxy)carbamoyl]thiazol-2-yl}carbamate (204 mg) in dichloromethane (3.5 mL), and the mixture was stirred overnight under reflux. After cooling to room temperature, saturated aqueous sodium bicarbonate solution was slowly added to the reaction solution to adjust the reaction solution to basicity. The aqueous layer of the reaction solution adjusted to basicity was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (132 mg) as a solid. 1 The H-NMR spectrum data and melting point are as follows: 1 H NMR (DMSO-d6 / 300MHz):δ(ppm)= 7.98 (brs, 2H), 7.42-7.34 (m, 1H), 7.30-7.22 (m, 1H), 7.13-7.06 (m, 1H), 4.93 (s, 2H), 4.64 (d, 2H), 3.68 (t, 1H). Melting point: 171.5℃

[0186] Next, representative examples of Compound (I) are specifically listed in Tables 1-1 and 1-2. These compounds can be synthesized based on the above-mentioned production methods and synthesis examples, as well as methods known in the art. In the tables, No. indicates the compound number. R in Tables 1-1 and 1-2 １ , Y １ , Y ２ , Y ３ , Y ４ , and Y ５ The abbreviations used in the columns represent the following substituents: Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, c-Pr is a cyclopropyl group, t-Bu is a tertiary butyl group, c-Bu is a cyclobutyl group, CN is a cyano group, and NO is a methyl group. ２ is a nitro group. In Table 1-1, = indicates a double bond.

[0187] Furthermore, in the case of salts of compound (I), the type of salt is indicated in the remarks column in Tables 1-1 and 1-2. For example, in the remarks column in Table 1-1, compounds described as HCl salt are hydrochlorides, compounds described as TsOH salt are paratoluenesulfonates, and compounds described as Na salt are sodium salts. For example, compound No. A-125 is the hydrochloride salt of compound No. A-20. Compound No. A-126 is the paratoluenesulfonate salt of compound No. A-20. Compound No. A-127 is the sodium salt of compound No. A-20.

[0188] In the remarks column of Table 1-2, compounds described as HCl salt are hydrochlorides, compounds described as TsOH salt are paratoluenesulfonates, and compounds described as Na salt are sodium salts. For example, Compound No. B-52 is the hydrochloride salt of Compound No. B-2. Compound No. B-53 is the paratoluenesulfonate salt of Compound No. B-2. Compound No. B-54 is the sodium salt of Compound No. B-2.

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] The physical properties of compound (I) synthesized according to the above-mentioned production method and examples are shown in Tables 2 and 3. Table 2 shows the melting point of compound (I). Table 3 shows the melting point of compound (I). 1 H-NMR spectrum data [ 1 1H-nuclear magnetic resonance spectroscopy; δ is the chemical shift value (ppm). The numbers in Tables 2 and 3 have the same meanings as in Tables 1-1 and 1-2. In the melting points in Table 2, *1 indicates the temperature at which the compound decomposed when the melting point was measured. In Table 3, 1 In the H-NMR spectrum data, s is a singlet, brs is a broadened singlet, d is a doublet, t is a triplet, q is a quartet, and m is a multiplet.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215] [Test Examples] Preparation of each medicinal solution containing the compound of the present invention: The compound of the present invention was mixed with acetone or dimethyl sulfoxide to dissolve the compound of the present invention. Water was added to the solution of the compound of the present invention to dilute it so that the compound of the present invention, which is the active ingredient, reached a predetermined concentration (400 ppm), thereby obtaining a medicinal solution. This medicinal solution was used in the following Test Examples 1 to 3.

[0216] Test Example 1: Fungicidal Effect Test (Preventive Effect Test) Against Tomato Late Blight (Phytophthora infestans) Tomatoes were grown in 6 cm diameter vinyl pots, and when they reached the 4.5 to 5.5 leaf stage, 10 ml of the solution was sprayed with a spray gun. After the solution dried (on the day of treatment), a spore suspension of tomato late blight (Phytophthora infestans) was sprayed and inoculated, and the plants were placed in an inoculation box at a temperature of 20°C and a humidity of 95% or more for 16 hours. The plants were then placed in a thermostatic chamber at 20°C, and 3 days after inoculation, the lesion area rate was investigated, and the control rate was calculated according to the following formula. As a result, each of the solutions containing the following test compounds (active ingredient concentration: 400 ppm) showed a control rate of 90% or more against tomato late blight. [Calculation formula for control rate] Control rate (%) = 100 - (X / Y) x 100 X: lesion area rate (%) of the test compound, Y: lesion area rate (%) of the untreated plot Test compounds: Compound No. A-3, A-5, A-6, A-7, A-8, A-10, A-11, A-12, A-14, A-15, A-16, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-45, A-46, A-47, A-48, A-50, A-51, A-52, A-54, A-5 5, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A- 72, A-73, A-74, A-75, A-76, A-77, A-78, A-79, A-82, A-83, A-84, A-85, A-86, A-87, A-88, A-89, A-91, A-92, A-93, A-94, A-95, A-96, A-97, A-98, A-99, A-100, A-101, A-102, A-103, A-104, A-10 5, A-106, A-108, A-109, A-110, A-111, A-112, A-113, A-114, A-115, A-116, A-117, A-118, A-119 , A-120, A-121, A-122, A-123, A-124, A-128, A-129, A-131, A-132, A-133, A-135, A-138, A-152,A-184、A-191、A-198、A-199、A-200、A-201、A-202、A-203、A-204、A-205、A-206、A-207、A-208、A-209、A-210、A-211、A-212、A-213、A-214、A-215、A-216、A-217、A-218、A-219、A-220、A-221、A-222、A-224、A-225、A-226、A-227、A-230、A-232、A-234、A-235、A-236、A-237、A-238、B-1、B-2、B-3、B-4、B-5、B-6、B-7、B-8、B-9、B-10、B-11、B-12、B-13、B-14、B-15、B-16、B-17、B-18、B-19、B-20、B-21、B-22、B-24、B-25、B-40、B-43、B-47、B-50、B-55、B-57、B-64、B-89、B-105、B-108、B-111、B-112、B-113、B-114、B-115、B-116、B-117、B-118、B-119、B-120、B-121、B-122、B-123、B-124、B-125、B-126、B-127、B-128、

[0217] Test Example 2: Fungicidal Effect Test (Preventive Effect Test) Against Cucumber Downy Mildew (Pseudoperonospora cubensis) Cucumbers were grown in 6 cm diameter vinyl pots, and when they reached the 1.2 to 1.5 leaf stage, 10 ml of the solution was sprayed with a spray gun. After the solution dried (on the day of treatment), a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis) was sprayed and inoculated, and the plants were placed in an inoculation box at a temperature of 20°C and a humidity of 95% or higher for 24 hours. The plants were then placed in a thermostatic chamber at 20°C, and 7 days after inoculation, the lesion area ratio was investigated, and the control rate was calculated using the same formula as in Test Example 1 above. As a result, each solution containing the following test compounds (active ingredient concentration 400 ppm) showed a control rate of 90% or higher against cucumber downy mildew.Test compounds: Compound No. A-3, A-5, A-6, A-10, A-12, A-15, A-16, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-35, A-38, A-39, A-40, A-42, A-43, A-45, A-47, A-48, A-50, A-51, A-52, A-54, A-55, A-57, A-58, A-59, A-62, A-64, A-65, A-67, A-68, A-69, A-71, A-72, A-73, A-75, A-76, A-77, A-78, A-79, A-82, A-83, A-85, A-91, A-92, A-94, A-95, A-96, A-97, A-98, A-99, A-100, A-102, A-103, A-106, A-109, A-111, A-112, A-113, A-114, A-115, A-116, A-117, A-118, A-119, A-120, A-121, A-122, A-123, A-124, A-128, A-129, A-131, A-132, A-133, A-135, A-138, A-145, A-152, A-184, A-191, A-198, A-199, A-200, A-201, A-202, A-203, A-204, A-205, A-206, A-207, A-208, A-209, A-210, A-211, A-212, A-213, A-214, A-215, A-216, A-217, A-218, A-219, A-220, A-221, A-222, A-223, A-224, A-225, A-226, A-232, A-234, A-237, A-238, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-9, B-10, B-11, B-13, B-14, B-15, B-16, B-17, B-18, B-19, B-20, B-21, B-22, B-24, B-25, B-40, B-43, B-47, B-50, B-55, B-57, B-64, B-105, B-108, B-111, B-112, B-113, B-114, B-115, B-116, B-117, B-118, B-119, B-120, B-121, B-122, B-123, B-124, B-125, B-126, B-127, B-128.

[0218] Test Example 3: Fungicidal Effect Test (Cure Effect Test) Against Tomato Late Blight (Phytophthora infestans) Tomatoes were grown in 6 cm diameter vinyl pots, and when they reached the 4.5 to 5.5 leaf stage, they were inoculated by spraying with a spore suspension of tomato late blight (Phytophthora infestans), and then placed in an inoculation box at a temperature of 20°C and humidity of 95% or more for 4 hours. Then, 10 ml of the solution was sprayed with a spray gun, and after the solution dried (on the day of treatment), the plants were placed in a thermostatic chamber at 20°C. Three days after inoculation, the lesion area ratio was investigated, and the control rate was calculated using the same formula as in Test Example 1 above. As a result, each solution containing the following test compounds (active ingredient concentration 400 ppm) showed a control rate of 90% or more against tomato late blight. Test compound: Compound No. A-2, A-5, A-6, A-10, A-11, A-12, A-13, A-14, A-16, A-18, A-19, A-20, A-21, A-22, A-23, A-29, A -31, A-32, A-33, A-34, A-35, A-36, A-38, A-40, A-41, A-43, A-45, A-48, A-50, A-52, A-55, A-57 , A-58, A-60, A-64, A-65, A-67, A-69, A-71, A-77, A-78, A-79, A-85, A-86, A-87, A-88, A-89, A- 91, A-92, A-93, A-95, A-97, A-99, A-101, A-109, A-111, A-113, A-115, A-116, A-117, A-118, A- 119, A-120, A-121, A-122, A-123, A-124, A-128, A-129, A-132, A-133, A-184, A-191, A-198, A- 199, A-200, A-202, A-203, A-204, A-205, A-206, A-207, A-208, A-209, A-210, A-211, A-213, A- 214, A-215, A-216, A-217, A-220, A-226, A-230, A-232, A-238, B-7, B-9, B-16, B-22, B-50, B-6 4, B-111, B-112, B-114, B-115, B-116, B-118, B-119, B-121, B-122, B-123, B-125, B-126, B-128

[0219] [Comparative Test] A comparative test was carried out using Compound No. A-10 of the present invention and the compound described in Production Example 2 of Patent Document 1 (hereinafter referred to as Comparative Compound 1) as active ingredients.

[0220] Preparation of chemical solutions containing each compound: Using each test compound listed in Table 4 below, each chemical solution was prepared using the same preparation method as above so that the active ingredient had a predetermined concentration (400 ppm, 200 ppm, 100 ppm, or 50 ppm). Each chemical solution adjusted to the predetermined concentration was used in the following Comparative Test Example 1.

[0221] Comparative Test Example 1: Test of fungicidal effect against cucumber downy mildew (Pseudoperonospora cubensis) (test of preventive effect) Using each of the chemical solutions adjusted to the above-mentioned predetermined concentrations, a test of fungicidal effect against cucumber downy mildew was carried out according to the method described in Test Example 2. The results for each active ingredient concentration of the chemical solution containing each test compound are shown in Table 4. A means 100% control rate, B means 90-99% control rate, C means 70-89% control rate, D means 30-69% control rate, and E means 0-29% control rate, respectively.

[0222]

[0223] As can be seen from Table 4, Compound No. A-10, an N-substituted oxyamide compound of the present invention, exhibited a superior control rate against cucumber downy mildew compared to the amide compound (Comparative Compound 1) of Patent Document 1. Therefore, from the examples, it was found that the N-substituted oxyamide compound of the present invention exhibits a superior control effect against harmful plant diseases. Furthermore, it was found that the N-substituted oxyamide compound of the present invention exhibits a superior control effect against harmful plant diseases compared to the amide compound of Patent Document 1.

[0224] Next, formulation examples containing Compound (I) are described, but the blending ratios, dosage forms, etc. are not limited to the described examples. Formulation Example 1 (1) Compound (I) 20 parts by weight (2) Clay 72 parts by weight (3) Sodium lignin sulfonate 8 parts by weight The above ingredients are mixed uniformly to prepare a wettable powder. Formulation Example 2 (1) Compound (I) 5 parts by weight (2) Talc 95 parts by weight The above ingredients are mixed uniformly to prepare a dust. Formulation Example 3 (1) Compound (I) 20 parts by weight (2) N,N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight The above ingredients are mixed uniformly and dissolved to prepare an emulsifiable concentrate.

[0225] Formulation Example 4 (1) Clay 68 parts by weight (2) Lignin sulfonic acid sodium 2 parts by weight (3) Polyoxyethylene alkyl aryl sulfate 5 parts by weight (4) Finely divided silica 25 parts by weight A mixture of the above components and compound (I) are mixed in a weight ratio of 4:1 to prepare a wettable powder. Formulation Example 5 (1) Compound (I) 50 parts by weight (2) Polyoxyethylene alkyl phenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight The above components are uniformly mixed and pulverized to prepare a stock solution, to which are further added (5) Sodium polycarboxylate 5 parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight, which are then uniformly mixed, granulated, and dried to prepare a water dispersible granule. Formulation Example 6 (1) Compound (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene phosphate ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4), and the acetone is removed to obtain granules.

[0226] Formulation Example 7 (1) Compound (I) 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight The above ingredients are uniformly mixed and dissolved to prepare an ultra low volume formulation. Formulation Example 8 (1) Compound (I) 20 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 parts by weight (6) Water 72.7 parts by weight The above ingredients are uniformly mixed and pulverized to prepare an aqueous suspension.

[0227] The entire contents of the specifications, claims and abstracts of Japanese Patent Application Nos. 2023-148047 and 2023-148050 filed on September 13, 2023 are hereby incorporated by reference as the disclosure of the specification of the present invention.

Claims

1. Formula (I): [In the formula, R １ (C １ -C ５ )-chain hydrocarbon, or (C ３ -C ４ )-cycloalkyl, １ -C ５ )-chain hydrocarbons and the (C ３ -C ４ )-cycloalkyl is at least one T １ Optionally substituted with T １ is halogen, cyano, or -U １ -R ２ And U １ is O, S, or C(=O)O; R ２ (C １ -C ３ )-alkyl, X １ is a halogen; Y １ , Y ２ , Y ３ , Y ４ and Y ５ Each independently represents a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, cyano, or a hydrogen atom, provided that R １ But (C １ -C ４ )-alkyl or (C ３ -C ４ )-cycloalkyl, then Y １ , Y ２ , Y ３ , Y ４ and Y ５ and n is an integer of 0 to 10; and n is an integer of 0 to 10.

2. R １ However, (C １ -C ４ )-alkyl, (C ３ -C ４ )-cycloalkyl, or (C ３ -C ５ 2. The compound or salt thereof according to claim 1, wherein R is 1 or 2.

3. The compound of formula (I) has the formula (IA); [In the formula, R １Ａ (C １ -C ４ )-alkyl, or (C ３ -C ４ )-cycloalkyl, X １ is a halogen; Y １ is a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, cyano, or a hydrogen atom; Y ２Ａ , Y ３Ａ and Y ４Ａ are each independently a hydrogen atom or a halogen atom; ５Ａ is a hydrogen atom. １ is a hydrogen atom, Y ２Ａ , Y ３Ａ and Y ４Ａ and n is an integer from 1 to 3, and n is an integer from 1 to 3. The compound according to claim 1, wherein n is an integer from 1 to 3, and n is an integer from 1 to 3.

4. The compound of formula (I) is represented by the formula (IB) [In the formula, n is 1, 2, or 3; X １ is a halogen; Y １ , Y ２ , Y ３ , Y ４ and Y ５ Each independently represents a hydrogen atom, a halogen atom, (C １ -C ６ )-alkyl, (C １ -C ６ 2. The compound according to claim 1, which is an N-alkynyloxyamide compound represented by the formula:

5. The compound of formula (I) has the formula (IA): [In the formula, R １Ａ (C １ -C ４ )-alkyl, or (C ３ -C ４ )-cycloalkyl, X １ is a halogen; Y １ is a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, nitro, cyano, or a hydrogen atom; Y ２Ａ , Y ３Ａ and Y ４Ａ are each independently a hydrogen atom or a halogen atom; ５Ａ is a hydrogen atom. １ is a hydrogen atom, Y ２Ａ , Y ３Ａ and Y ４Ａ and n is an integer of 1 to 5, and n is an integer of 1 to 5. In the formula (IB): [In the formula, n is 1, 2, or 3; X １ is a halogen; Y １ , Y ２ , Y ３ , Y ４ and Y ５ Each independently represents a hydrogen atom, a halogen atom, (C １ -C ６ )-alkyl, (C １ -C ６ 2. The compound according to claim 1, which is an N-alkynyloxyamide compound represented by the formula:

6. Y １ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ 6. The compound or salt thereof according to any one of claims 1 to 5, wherein R is -haloalkyl, nitro, or cyano.

7. R １Ａ The compound or salt thereof according to claim 3 or claim 5, wherein is methyl, ethyl or cyclopropyl.

8. Y ５ The compound or salt thereof according to any one of claims 1 to 5, wherein is a hydrogen atom.

9. An agricultural and horticultural fungicide comprising the compound or salt thereof according to any one of claims 1 to 5 as an active ingredient.

10. A method for controlling harmful plant diseases, which comprises applying an effective amount of the compound or salt thereof according to any one of claims 1 to 5 to a plant body, a plant pathogen or soil.