N-substituted oxyamide compound or salt thereof

Abstract

Provided is a novel compound exhibiting an excellent control 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 control effect on harmful plant diseases.

Description

Technical Field

[0001] This invention relates to novel N-substituted oxyamide compounds or their salts, and fungicides for agricultural and horticultural use containing them as active ingredients. Background Technology

[0002] Existing agricultural and horticultural fungicides suffer from problems such as insufficient practical control of harmful plant diseases depending on the application site, the emergence of drug-resistant bacteria, and environmental burdens (impact on surrounding plants and ecosystems). Therefore, there is an urgent need for novel agricultural and horticultural fungicides. Furthermore, from the perspective of preventing environmental pollution, there is a desire for agricultural and horticultural fungicides that demonstrate excellent control of harmful plant diseases with the lowest possible dosage.

[0003] Patent Document 1 discloses amide compounds and their use in controlling plant diseases. However, Patent Document 1 makes no specific description of the compounds represented by the following formula (I).

[0004] Compounds that can be used as antimicrobial agents include, for example, known N-alkoxycarboxamides (Patent Document 2). However, Patent Document 2 does not contain any specific description of the compounds represented by the following formula (I).

[0005] Non-Patent Literature 1 discloses, in Table I, No. 15, tests on the 5-hydroxytryptophan decarboxylase inhibitory activity and monoamine oxidase inhibitory activity of N-benzoyl-N-benzyl-O-2-propynylhydroxylamine. However, Non-Patent Literature 1 makes no mention whatsoever of the control efficacy of the compounds described therein against harmful plant diseases. Furthermore, Non-Patent Literature 1 also makes no mention of compounds represented by the following formula (I).

[0006] On the other hand, compounds 2-amino-N-benzyl-N-methoxy-1,3-thiazolyl-5-carboxamide (CAS Registry No.: 2301497-10-7) and 2-amino-N-benzyl-N-methoxy-4-methyl-1,3-thiazolyl-5-carboxamide (CAS Registry No.: 2299658-69-6) are known. However, their uses are unclear, and of course, their effects on plant diseases are completely unknown.

[0007] Existing technical documents

[0008] Patent documents

[0009] Patent Document 1: International Publication No. 2010 / 134634

[0010] Patent Document 2: International Publication No. 2011 / 023645

[0011] Non-patent literature

[0012] Non-patent literature 1: Journal of Medicinal Chemistry 1969, 12(1), 45-48 Summary of the Invention

[0013] The problem that the invention aims to solve

[0014] The objective of this invention is to provide novel compounds that exhibit excellent control effects against harmful plant diseases.

[0015] Methods for solving problems

[0016] In order to solve the above-mentioned problems, the inventors conducted in-depth research and found that the compound or its salt represented by the following formula (I) has excellent control effect on harmful plant diseases.

[0017] That is, the present invention is as follows.

[0018] [1] The compound or its salt represented by formula (I) (hereinafter also referred to as compound (I)).

[0019]

[0020] [In the formula, R] 1 It is a (C1-C5)-chain hydrocarbon or a (C3-C4)-cycloalkyl group {wherein, the (C1-C5)-chain hydrocarbon and the (C3-C4)-cycloalkyl group can be substituted by at least one T} 1 replace}, T 1 Halogen, cyano or -U 1 -R 2 , U 1 For O, S, or C(=O)O, R 2 It is (C1-C3)-alkyl. X 1 Halogen, Y 1 Y 2 Y 3 Y 4 and Y 5 Each is independently a halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, cyano, or hydrogen atom. Among them, in R... 1 In the case of (C1-C4)-alkyl or (C3-C4)-cycloalkyl, Y 1 Y 2 Y 3 Y 4 and Y 5 Not all of them are hydrogen atoms at the same time. [2] According to the compound or its salt described in [1] above, R 1 It is (C1-C4)-alkyl, (C3-C4)-cycloalkyl, or (C3-C5)-alkynyl.

[0021] [3] According to the compound or its salt described in [1] above, the compound represented by formula (I) is an N-(cyclo)alkoxyamide compound represented by formula (IA) (hereinafter also referred to as compound (IA)).

[0022]

[0023] [In the formula, R] 1A It is (C1-C4)-alkyl or (C3-C4)-cycloalkyl. X 1 Halogen, Y 1 It can be a halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, cyano, or hydrogen atom. Y 2A Y 3A and Y 4A Each can be independently a hydrogen atom or a halogen. Y 5A It is a hydrogen atom. Wherein, in Y... 1 In the case of hydrogen atoms, Y 2A Y 3A and Y 4A Not all of them are hydrogen atoms at the same time. [4] According to the compound or its salt described in [1] above, the compound represented by formula (I) is an N-alkynyl oxyamide compound represented by formula (IB) (hereinafter also referred to as compound (IB)).

[0024]

[0025] [In the formula, n is 1, 2, or 3,] X 1 Halogen, Y 1 Y 2 Y 3 Y 4 and Y 5 Each of these can be independently a hydrogen atom, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano. [5] According to the compound or its salt described in [1] above, the compound represented by formula (I) is an N-(cyclo)alkoxyamide compound represented by formula (IA) or an N-alkynyl oxyamide compound represented by formula (IB).

[0026]

[0027] [In the formula, R] 1A It is (C1-C4)-alkyl or (C3-C4)-cycloalkyl. X 1 Halogen, Y 1 It can be a halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, cyano, or hydrogen atom. Y 2A Y 3A and Y 4A Each can be independently a hydrogen atom or a halogen. Y 5A It is a hydrogen atom. Wherein, in Y... 1 In the case of hydrogen atoms, Y 2A Y 3A and Y 4A Not all of them are hydrogen atoms at the same time.

[0028] [In the formula, n is 1, 2, or 3,] X 1 Halogen, Y 1 Y 2 Y 3 Y 4 and Y 5 Each of these can be independently a hydrogen atom, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano. [6] According to any one of the above [1] to [5] compounds or salts thereof, Y 1 It can be halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

[0029] [7] According to the compound or salt thereof described in [3] or [5] above, R 1A It can be methyl, ethyl, or cyclopropyl.

[0030] [8] The compound or salt thereof according to any one of [1], [2] and [4] to [6] above, Y 5 It is a hydrogen atom.

[0031] [9] An agricultural and horticultural fungicide, which contains the compound or salt thereof as any one of the above [1] to [8] as an active ingredient.

[0032]

[10] A method for preventing and controlling harmful plant diseases, wherein an effective amount of any one of the above [1] to [8] compounds or their salts are applied to the plant, plant pathogens or soil.

[0033] The effects of the invention

[0034] The compound (I) of the present invention exhibits excellent control effects against harmful plant diseases and is useful as a fungicide for agricultural and horticultural use. Detailed Implementation

[0035] The various substituents and chemical structures described in this specification are explained. It should be noted that compound (I) includes compound (IA) and compound (IB), and they are collectively referred to as the compounds of this invention.

[0036] Examples of halogens, or halogens used as substituents, include atoms of fluorine, chlorine, bromine, or iodine. The number of halogens used as substituents can be one or more; when there are two or more, the individual halogen atoms can be the same or different. Furthermore, the substitution position of the halogens used as substituents can be any position.

[0037] “C P -C T "" indicates the number of carbon atoms is P~T. For example, "C1-C4" means the number of carbon atoms is 1~4. In addition, the expression "can be substituted" indicates whether it has substituents or not.

[0038] (C1-C5)-chain hydrocarbons represent (C1-C4)-alkyl, (C3-C5)-alkynyl, or (C3-C5)-alkene.

[0039] Examples of (C1-C4)-alkyl groups include straight-chain or branched alkyl groups with 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0040] Examples of (C3-C5)-alkynyl groups include 1-propynyl, propynyl (also simply called 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, 3-butyn-2-yl, but-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, pent-1,3-diynyl, pent-1,4-diynyl, or pent-2,4-diynyl, which are straight-chain or branched alkynyl groups with 3 to 5 carbon atoms and at least one triple bond at any position.

[0041] Examples of (C3-C5)-alkenyl groups include allyl (also known as 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, but-1,3-dienyl, but-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, pent-1,3-dienyl, pent-2,4-dienyl, or pent-2,4-dien-2-yl, which are straight-chain or branched alkenyl groups with at least one double bond at any position and 3 to 5 carbon atoms. Furthermore, when geometric isomers exist, there are no particular limitations as long as they are either E-body or Z-body, or a mixture of E-body and Z-body in any proportion, and are within the specified range of carbon atoms.

[0042] Examples of (C1-C6)-alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, sec-pentyl, 1-ethylpropyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, 2-methylpentyl, 3-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, tert-hexyl, 2,2-dimethylbutyl, neohexyl, 1-ethyl-2-methylpropyl, or 1-ethyl-1-methylpropyl, which are straight-chain or branched alkyl groups having 1 to 6 carbon atoms.

[0043] (C1-C3)-alkyl refers to a straight-chain or branched alkyl group having 1 to 3 carbon atoms. Specific examples are the alkyl groups with 1 to 3 carbon atoms in the specific examples of (C1-C6)-alkyl mentioned above.

[0044] (C3-C4)-cycloalkyl groups represent cyclic hydrocarbon groups consisting of 3 to 4 carbon atoms, which can form monocyclic structures of 3- to 4-membered rings. Furthermore, in the case of forming a 3-membered monocyclic structure, a methyl group can be substituted at any position within a specified range of carbon atoms. Examples of cycloalkyl groups with 3 to 4 carbon atoms include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, and cyclobutyl.

[0045] The above-mentioned (C1-C5)-chain hydrocarbons and the above-mentioned (C3-C4)-cycloalkyl groups can be substituted by at least one T. 1 Substitution. In the above (C1-C5)-chain hydrocarbons, T... 1 In the case of substitution, the above (C1-C5)-chain hydrocarbons can be replaced by 1 to 9 T... 1 Substitution. The above (C3-C4)-cycloalkyl group is replaced by T. 1In the case of substitution, the above (C3-C4)-cycloalkyl group can be replaced by 1 to 7 T groups. 1 replace.

[0046] The above (C1-C5)-chain hydrocarbons or the above (C3-C4)-cycloalkyl groups are subjected to at least one T 1 In the case of replacement, T 1 The substitution position can be any substitution position on the (C1-C5)-chain hydrocarbon or the (C3-C4)-cycloalkyl group described above.

[0047] In the above (C1-C5)-chain hydrocarbons or the above (C3-C4)-cycloalkyl groups, two or more T atoms are involved. 1 In the case of replacement, each T 1 They can be the same or different.

[0048] For example, in the R of compound (I) 1 For at least 1 T 1 In the case of substituted (C1-C4)-alkyl groups, specifically, the following substituents are included. Examples include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, dichlorodifluoromethyl, 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, ethoxymethyl, propoxymethyl, 2-methylthioethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, or isopropoxycarbonylmethyl, etc.

[0049] For example, in the R of compound (I) 1 For at least 1 T 1In the case of substituted (C3-C4)-cycloalkyl groups, specifically, the following substituents are included. Examples include, for instance, 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, or 3-methoxycarbonylcyclobutyl, etc.

[0050] Examples of (C1-C6)-haloalkyl groups include, for instance, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, dichlorodifluoromethyl, 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, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, and 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, All Fluorobutyl, 2,3,3,3,4,4,4-heptafluoroisobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 1,1-difluoropentyl, 2,2-difluoropentyl, 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- Alkyl groups consisting of 1 to 6 carbon atoms, including fluorohexyl, 1,1-difluorohexyl, 2,2-difluorohexyl, 3,3-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, etc., partially or completely substituted with 1 to 13 identical or different halogen atoms.

[0051] (C1-C3)-haloalkyl refers to a straight-chain or branched haloalkyl with 1 to 3 carbon atoms. Specific examples are the haloalkyls with 1 to 3 carbon atoms in the specific examples of (C1-C6)-haloalkyl mentioned above.

[0052] In the above formula (IB), since n represents 1, 2 or 3, the compound (IB) is specifically represented by the following formulas (IB-a) to (IB-c).

[0053]

[0054] Among the compounds shown in formula (I), preferred compounds include N-(cyclo)alkoxyamide compounds of formula (IA), N-alkynyl oxyamide compounds of formula (IB), and compounds shown in formulas (Ia) to (Im) below.

[0055]

[0056] As a salt of compound (I), it includes all salts that are permitted in agriculture, such as alkali metal salts (e.g., sodium salts, potassium salts, etc.), alkaline earth metal salts (e.g., magnesium salts, calcium salts, etc.), amine salts (dimethylamine salts, triethylamine salts, etc.), inorganic acid salts (e.g., hydrochloride salts, perchlorate salts, sulfate salts, nitrate salts, etc.) or organic acid salts (e.g., acetate salts, methanesulfonate salts, p-toluenesulfonate salts, oxalate salts, etc.).

[0057] Compound (I) exists in various isomers, such as optical isomers and geometric isomers. In this invention, both individual isomers and mixtures of isomers are sometimes included. It should be noted that, within the scope of common knowledge in this art, compound (I) also includes various isomers other than those mentioned above. Furthermore, various isomers can be prepared separately using common technical knowledge and general experimental methods.

[0058] Furthermore, depending on the type of isomer, it may sometimes be a chemical structure different from the described structural formula, but anyone skilled in the art can fully recognize that they are isomers, and therefore this is clear within the scope of the present invention.

[0059] Next, the method for manufacturing compound (I) will be described.

[0060] Compound (I) can be prepared according to reactions A to E as shown below, and conventional salt preparation methods, but the method of obtaining the compound is not limited to these methods. For example, compound (I) of the present invention can also be prepared by applying various substituent conversion reactions known in the art (e.g., alkylation, haloalkylation, Suzuki coupling and other cross-coupling reactions, Sandmeier-type reactions, halogenation, oxidation, reduction, etc.) to the substituents on the phenyl group. Furthermore, protection and deprotection reactions commonly used in the art can be applied in the preparation of the compound of the present invention, as needed. 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 also be used.

[0061] [Reaction A]

[0062] Reaction A is a deprotection reaction, which is a method to obtain the compound of formula (I) by removing the Boc group from the compound of formula (XX-a). Here, the Boc group is a tert-butoxycarbonyl group.

[0063]

[0064] The symbols in the formula are shown above.

[0065] Reaction A can be carried out under known conditions used for the removal of the Boc group, such as those described in Greene's PROTECTIVEGROUPS in ORGANIC SYNTHESIS (John Wiley and Sons, 2007, Peter GMWuts, Theodora W. Greene). More specifically, for example, it can be carried out by reacting a 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 trifluoromethanesulfonate in the presence of a solvent and a base such as 2,6-dimethylpyridine.

[0066] [Reaction B] and [Reaction C]

[0067] 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).

[0068]

[0069] In the formula, R 1a For H, (C1-C5)-chain hydrocarbon, or (C3-C4)-cycloalkyl {here, the (C1-C5)-chain hydrocarbon and the (C3-C4)-cycloalkyl can be at least 1 T 1 Substitution. L is a dissociative group, which can be exemplified by halogens, alkoxy groups, aryloxy groups, alkyl carbonyloxy groups, aryl carbonyloxy groups, etc. Other symbols are shown above.

[0070] Reaction B can typically be carried out in the presence of a dehydrating condensing agent and a solvent, with the addition of a base as needed. The compound of formula (III) in reaction B can be used in an amount of 0.5 to 3 equivalents relative to the compound of formula (II), preferably 0.8 to 1.5 equivalents (equivalents are molar equivalents, and the same applies below).

[0071] Examples of dehydrating condensing agents in reaction B include carbodiimide condensing agents such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC), or their hydrochlorides; imidazole condensing agents such as 1,1'-carbonyldiimidazole (CDI); and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholine. Triazine condensing agents such as chloride (DMT-MM); 1H-benzotriazole-1-yloxy-tripyrrolidinyl hexafluorophosphate (PyBOP) and the like Condensing agent; 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridine Urea condensing agents such as 3-oxide hexafluorophosphate (HATU); acid anhydrides such as 2-methyl-6-nitrobenzoic anhydride (MNBA); 2-chloro-1-methylpyridine 2-Halopyridines such as p-toluenesulfonate Salts; propylphosphonic anhydride (cyclic trimer) (T3P); diphenylphosphine azide (DPPA); etc., but not limited to these. General additives such as 1-hydroxybenzotriazole (HOBt), used in conjunction with dehydrating condensing agents, may be added as needed. The aforementioned dehydrating condensing agent may be used in amounts of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II), and the aforementioned additives may be used in amounts of 0.2 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II).

[0072] The base in reaction B can be one or more of the following substances, selected appropriately and used in combination: for example, carbonates such as sodium carbonate, potassium carbonate, and cesium 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-dimethylpyridine; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base can be used in amounts of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (II), preferably 1 to 5 equivalents.

[0073] The solvent in reaction B can be any solvent that is inactive in the reaction. One or more of the following substances can be appropriately selected: aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; nonprotic 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; water; etc.

[0074] The reaction temperature of reaction B is usually around -20℃ to 150℃, preferably around 0℃ to 100℃, and the reaction time is usually around 0.5 to 48 hours, preferably around 1 to 24 hours.

[0075] Reaction C can be carried out in the presence of a solvent, with the addition of a base as needed. The compound of formula (III) in reaction C can be used in an amount of 0.5 to 3 equivalents relative to 1 equivalent of the compound of formula (II-a), preferably 0.8 to 1.5 equivalents.

[0076] The base in reaction C can be selected from one or more of the following substances and used in combination: for example, carbonates such as sodium carbonate, potassium carbonate, and cesium 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-dimethylpyridine; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base can be used in amounts of 0.1 to 10 equivalents relative to 1 equivalent of the compound of formula (II-a), preferably 0.5 to 5 equivalents.

[0077] The solvent in reaction C can be any solvent that is inactive in the reaction. One or more of the following substances can be appropriately selected: aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; nonprotic 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; water; etc.

[0078] The reaction temperature of reaction C is usually around -20℃ to 150℃, preferably around 0℃ to 100℃, and the reaction time is usually around 0.5 to 48 hours, preferably around 1 to 24 hours.

[0079] The compound of formula (III) used in reactions B and C can be prepared according to reaction 2-2 or reaction 2-4 described later.

[0080] The compound of formula (II) used in reaction B can be prepared according to reaction 1-1, reaction 1-2 or known methods described later, or commercially available products can be used.

[0081] The compound of formula (II-a) used in reaction C can be prepared from the compound of formula (II) according to reactions 1-4 below or by known methods. The compound of formula (II-a) can also be a commercially available product.

[0082] [Reaction D]

[0083] Reaction D is a method of obtaining compound (XX-a) by reacting a compound of formula (XX-c) with a compound of formula (IV).

[0084]

[0085] In the formula, L 1 Examples of radicals that can be used to decompose a radical include halogens, trifluoromethanesulfonyloxy, methanesulfonyloxy, p-toluenesulfonyloxy, and others as shown above.

[0086] Reaction D is typically carried out in the presence of a base and a solvent, with the addition of a phase transfer catalyst as needed. The compound of formula (IV) in reaction D can be used in amounts of 1 to 5 equivalents relative to the compound of formula (XX-c), preferably 1 to 3 equivalents.

[0087] The base in reaction D can be selected from one or more of the following substances and used in combination: alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate, potassium carbonate, and cesium 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-dimethylpyridine; organolithium compounds such as n-butyllithium and diisopropylaminolithium; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base can be used in amounts of 1 to 10 equivalents relative to 1 equivalent of the compound of formula (XX-c), preferably 1 to 5 equivalents.

[0088] The solvent in reaction D can be any solvent that is inactive in the reaction. One or more of the following substances can be appropriately selected: aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, 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; water; etc.

[0089] Examples of phase transfer catalysts in reaction D include, for instance, quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown ether-6; etc. The amount of the aforementioned phase transfer catalyst relative to the compound of formula (XX-c) can be 0.1 to 3 equivalents.

[0090] The reaction temperature of reaction D is usually around -20℃ to 150℃, preferably around 0℃ to 100℃, and the reaction time is usually around 10 minutes to 48 hours, preferably around 1 to 24 hours.

[0091] The compound of formula (IV) used in reaction D can be manufactured according to known methods or can be commercially available.

[0092] [Reaction E]

[0093] Reaction E is a method for obtaining compound (XX-b) by reacting a compound of formula (II-b) with a compound of formula (V).

[0094]

[0095] The symbols in the formula are shown above.

[0096] Reaction E can proceed according to reaction D described above. In reaction E, the compound of formula (V) can be used in an amount of 1 equivalent relative to the compound of formula (II-b), preferably 1 to 2 equivalents. In reaction E, the base can be used in an amount of 1 equivalent relative to the compound of formula (II-b), preferably 1 to 10 equivalents, preferably 1 to 5 equivalents. In reaction E, the phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents relative to the compound of formula (II-b).

[0097] The compound of formula (II-b) used in reaction E can be prepared according to reactions 1-3 below or by known methods, or a commercially available product can be used. The compound of formula (V) used in reaction E can be prepared according to known methods, or a commercially available product can be used.

[0098] The compounds used in reactions A through E can be manufactured according to the methods for manufacturing the intermediates described below (reactions 1-1 through 1-4 and reactions 2-1 through 2-4) and the usual methods for manufacturing salts, but are not limited to these methods. These compounds can be manufactured according to known methods or commercially available products can be used.

[0099] Manufacturing methods of each intermediate

[0100] [Reaction 1-1], [Reaction 1-2], and [Reaction 1-3]

[0101] Reaction 1-1 is a method of oxidizing the compound of formula (1) to obtain the compound of formula (II). Reaction 1-2 is a method of hydrolyzing the compound of formula (2) to obtain the compound of formula (II). Reaction 1-3 is a method of reacting the compound of formula (II) or the compound of formula (II-a) with the compound of formula (3) to obtain the compound of formula (II-b).

[0102]

[0103] In the formula Z 1 It is an alkyl group; other symbols are as shown above.

[0104] Reaction 1-1 can be carried out under the usual Pinnick oxidation conditions, for example, as described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.

[0105] The compound of formula (1) used in reaction 1-1 can be manufactured according to known methods, such as those described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182, Journal of Organic Chemistry, 2005, 70, 567-574, International Publication No. 2020 / 028141, or Organic Process Research and Development, 2021, 25, 1167-1175, or can be a commercially available product.

[0106] Reactions 1-2 can be carried out under the usual conditions for ester hydrolysis, such as the method described in International Publication No. 2009 / 100171.

[0107] The compound of formula (2) used in reactions 1-2 can be manufactured by known methods, such as those described in International Publication No. 2012 / 006760, or commercially available products can be used.

[0108] Reactions 1-3 can be carried out according to reaction B or reaction C as described above. The compound of formula (3) in reactions 1-3 can be used in an amount of 1 equivalent to the compound of formula (II) or the compound of formula (II-a), and can be used in amounts of 0.5 to 10 equivalents, preferably 0.7 to 5 equivalents.

[0109] The compound of formula (3) used in reactions 1-3 can be manufactured by known methods, for example, according to the methods described in International Publication No. 2006 / 138350, U.S. Patent Application Publication No. 2014 / 0378399, Organic & Biomolecular Chemistry, 2020, 18, 3281-3287, and The Journal of Antibiotics, 2000, 53, 1071-1085, or commercially available products can be used.

[0110] [Reactions 1-4]

[0111] Reactions 1-4 are methods for obtaining compounds of formula (II-a) from compounds of formula (II) by halogenation, esterification, or carbonylation.

[0112]

[0113] The symbols in the formula are shown above.

[0114] The following descriptions of reactions 1-4 describe the reaction conditions under halogenation.

[0115] In reactions 1-4, when L of the compound of formula (II-a) is a halogen, the compound of formula (II) can usually be halogenated by reacting it with a halogenating agent in the presence of a solvent, or N,N-dimethylformamide can be added as needed.

[0116] Examples of halogenating agents used in reactions 1-4 include oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, and sulfonyl chloride. The amount of the halogenating agent used relative to one equivalent of the compound of formula (II) can be 1 to 10 equivalents, preferably 1 to 3 equivalents. An excess may also be used if it does not cause problems with the reaction.

[0117] In the case of using N,N-dimethylformamide in reactions 1-4, the amount of N,N-dimethylformamide used is the amount of catalyst, for example, 0.01 to 0.3 equivalents relative to the amount of compound 1 of formula (II).

[0118] The following descriptions of reactions 1-4 describe the reaction conditions under esterification.

[0119] In reactions 1-4, when L of the compound of formula (II-a) is an alkoxy or aryloxy group, the compound of formula (II) can usually be esterified by adding a base as needed in the presence of a solvent and a dehydrating condensing agent, so that the compound can react with an alcohol or an aryl hydroxyl group.

[0120] Examples of alcohols used in reactions 1-4 include methanol and ethanol. Examples of aryl hydroxyl groups used in reactions 1-4 include phenol. The amount of the alcohol or aryl hydroxyl group relative to 1 equivalent of the compound of formula (II) can be 0.5 to 5 equivalents, preferably 0.8 to 1.5 equivalents. An excess amount may also be used if it will not cause problems to the reaction.

[0121] As the dehydrating condensing agent in reactions 1-4, the substances exemplified in reaction B above can be used. When using the above-mentioned dehydrating condensing agent in reactions 1-4, a general additive used with the dehydrating condensing agent (e.g., 1-hydroxybenzotriazole (HOBt), etc.) can be added as needed. The above-mentioned dehydrating condensing agent can be used in an amount of 0.5 to 5 equivalents relative to compound 1 of formula (II), preferably 1 to 2 equivalents; the above-mentioned additive can be used in an amount of 0.2 to 5 equivalents relative to compound 1 of formula (II), preferably 1 to 2 equivalents.

[0122] When using a base with the aforementioned dehydrating condensing agent in reactions 1-4, the base may be the substance exemplified in reaction B. The base may be used in amounts of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (II).

[0123] In addition, in reactions 1-4, when L of the compound of formula (II-a) is an alkoxy group, a solvent and a base can usually be added to react the compound of formula (II) with alkyl halides to carry out esterification.

[0124] Examples of alkyl halides used in reactions 1-4 include iodomethane and iodoethane. The amount of the alkyl halide relative to the compound of formula (II) can be 0.5 to 5 equivalents, preferably 0.8 to 1.5 equivalents.

[0125] As a base that can be used in reactions with alkyl halides of reactions 1-4, the substances exemplified in reaction D above can be used. The base can be used in amounts of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (II), preferably 1 to 5 equivalents.

[0126] The following descriptions of reactions 1-4 describe the reaction conditions under carbonylation.

[0127] In reactions 1-4, when L of the compound of formula (II-a) is an alkyl carbonyloxy or aryl carbonyloxy, the compound of formula (II) can usually be carbonylated by reacting it with a carbonylating agent in the presence of a solvent and a base.

[0128] Examples of carbonylating agents used in reactions 1-4 include acetyl chloride, pivaloyl chloride, benzoyl chloride, acetic anhydride, and benzoic anhydride. The carbonylating agent can be used in amounts of 0.5 to 10 equivalents relative to the compound of formula (II), preferably 1 to 5 equivalents. Excessive amounts may also be used if it does not cause problems with the reaction.

[0129] As the base used in reactions 1-4 where carbonylation is involved, the substances exemplified in reaction B above can be used. The base can be used in amounts of 0.5 to 10 equivalents relative to the compound of formula (II), preferably 1 to 5 equivalents.

[0130] The solvents used in reactions 1-4 can be any type of solvent that is inactive in the reaction. One or more of the following substances can be appropriately selected: aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; nonprotic 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; water; etc.

[0131] The reaction temperature in reactions 1-4 is usually around -50℃ to 200℃, preferably around -20℃ to 100℃, and the reaction time is usually around 0.1 to 12 hours.

[0132] [Reaction 2-1]~[Reaction 2-4]

[0133] Reaction 2-1 is a method of reacting the compound of formula (10) with the compound of formula (3) to obtain the compound of formula (11). Reaction 2-2 is a method of reducing the compound of formula (11) to obtain the compound of formula (III). Reaction 2-1 and reaction 2-2 can also be carried out continuously without separating the compound of formula (11).

[0134] Reaction 2-3 is a method of obtaining compound (11-b) by reacting compound (11-a) with compound (IV).

[0135] Reactions 2-4 are methods for obtaining compounds of formula (III) by reacting a compound of formula (V) with a compound of formula (3).

[0136]

[0137] The symbols in the formula are shown above.

[0138] Reaction 2-1 can be carried out by adding an acid, base, or dehydrating agent as needed. Alternatively, reaction 2-1 can be carried out in the presence of a solvent. In this case, the compound of formula (3) in reaction 2-1 can be used in an amount of 1 to 5 equivalents relative to the compound of formula (10), and an excess can be used if it will not cause problems for the reaction.

[0139] The acid in reaction 2-1 can be any kind of inorganic acid or organic acid. Examples of inorganic acids include hydrochloric acid and sulfuric acid, while examples of organic acids include acetic acid, methanesulfonic acid, and p-toluenesulfonic acid. The equivalent of the acid to the compound of formula (10) is 0.1 to 10 equivalents. If it does not cause problems with the reaction, it can be used in excess.

[0140] Examples of bases in reaction 2-1 include, for example, 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-dimethylpyridine; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The bases mentioned above can be used in amounts of 0.5 to 5 equivalents relative to 1 equivalent of the compound in formula (3).

[0141] Examples of dehydrating agents used in reaction 2-1 include anhydrous magnesium sulfate, anhydrous sodium sulfate, and molecular sieves.

[0142] The solvent in reaction 2-1 can be any type of solvent that is inactive in the reaction. For example, one or more of the following substances can be appropriately selected: 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; etc.

[0143] The reaction temperature of reaction 2-1 is usually around -20℃ to 200℃, preferably around 0℃ to 150℃, and the reaction time is usually around 0.5 to 48 hours, preferably around 1 to 24 hours.

[0144] Alternatively, reaction 2-1 can be carried out under the usual conditions based on the dehydration condensation of aldehydes with hydroxylamines or alkoxyamines, for example, the method described in HETEROCYCLES, 2009, 78, 463-470. Under the usual dehydration condensation conditions, the compound of formula (3) in reaction 2-1 can be used in an amount of 0.7 to 5 equivalents relative to the compound of formula (10), preferably 1 to 2 equivalents.

[0145] The compounds of formula (10) and formula (3) used in reaction 2-1 can be manufactured by known methods or commercially available products can be used.

[0146] Reaction 2-2 can usually be carried out in the presence of a reducing agent and a solvent, with the addition of an acid as needed.

[0147] Examples of reducing agents in reaction 2-2 include sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and 2-methylpyridine-borane coordination compounds. The amount of reducing agent relative to the amount of compound 1 in formula (11) can be 0.5 to 10 equivalents, preferably 1 to 5 equivalents. The added acid can be any type of inorganic or organic acid; examples of inorganic acids include hydrochloric acid, and examples of organic acids include acetic acid and trifluoroacetic acid. The amount of the acid relative to the amount of compound 1 in formula (11) can be 1 to 10 equivalents.

[0148] The solvent in reaction 2-2 can be any solvent that is inactive in the reaction. One or more of the following substances can be selected: aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, 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; water; etc.

[0149] The reaction temperature of reaction 2-2 is usually around -20℃ to 150℃, preferably around 0℃ to 100℃, and the reaction time is usually around 0.5 to 48 hours, preferably around 1 to 24 hours.

[0150] Alternatively, reaction 2-2 can be carried out under the usual conditions for reducing oximes or oxime ethers, for example, the methods described in HETEROCYCLES, 2009, 78, 463-470.

[0151] The compound of formula (11) used in reaction 2-2 can be manufactured according to reaction 2-1 above or a known method, or a commercially available product can be used.

[0152] Reactions 2-3 can proceed according to reaction D. The compound of formula (IV) can be used in an amount of 1 equivalent relative to the compound of formula (11-a), preferably 1-2 equivalents. The base in reaction 2-3 can be used in an amount of 1 equivalent relative to the compound of formula (11-a), preferably 1-5 equivalents. The phase transfer catalyst in reaction 2-3 can be used in an amount of 0.1-3 equivalents relative to the compound of formula (11-a).

[0153] Alternatively, reactions 2-3 can be carried out according to known oxime alkylation conditions, such as those described in International Publication No. 2010 / 049946.

[0154] The compound of formula (11-a) used in reactions 2-3 can be prepared according to reaction 2-1 above or a known method, or a commercially available product can be used. The compound of formula (IV) used in reactions 2-3 can be prepared according to a known method, or a commercially available product can be used.

[0155] Reactions 2-4 can typically be carried out in the presence of a base and a solvent, with the addition of a phase transfer catalyst as needed. The compound of formula (3) in reactions 2-4 can be used in amounts of 1 to 5 equivalents relative to the compound of formula (V), preferably 1 to 3 equivalents.

[0156] The base in reactions 2-4 can be selected from one or more of the following substances and used in combination: 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-dimethylpyridine; organolithium compounds such as n-butyllithium and diisopropylaminolithium; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base can be used in amounts of 1 to 10 equivalents relative to 1 equivalent of the compound of formula (V), preferably 1 to 5 equivalents.

[0157] The solvents used in reactions 2-4 can be any type of solvent that is inactive in the reaction. One or more of the following substances can be appropriately selected: aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, 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; water; etc.

[0158] Examples of phase transfer catalysts used in reactions 2-4 include, for instance, quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown ether-6; etc. The amount of the aforementioned phase transfer catalyst relative to compound 1 of formula (V) can be 0.1 to 3 equivalents.

[0159] The reaction temperature for reactions 2-4 is typically around -20℃ to 150℃, preferably around 0℃ to 100℃, and the reaction time is typically around 10 minutes to 48 hours, preferably around 1 to 24 hours.

[0160] Alternatively, reactions 2-4 can be carried out according to known alkylation conditions for alkoxyamines, such as those described in Organic Letters, 2004, 6, 2361-2364.

[0161] The compounds of formula (V) and formula (3) used in reactions 2-4 can be manufactured by known methods or commercially available products can be used.

[0162] Compound (I) is useful as an active ingredient in an agricultural and horticultural fungicide that can control harmful plant diseases at low doses.

[0163] Compound (I) is effective against plant diseases caused by pathogens belonging to phyla such as Oomycota, Endomyxa, Olpidiomycota, Ascomycota, Basidiomycota, and Blastodactyta. It is particularly effective against plant diseases caused by pathogens belonging to Oomycota, Endomyxa, and Olpidiomycota.

[0164] Examples of plant pathogens belonging to the above categories include the following.

[0165] Examples of plant pathogens belonging to the phylum Oomycota include: Albuginales, Anisolpidiales, Lagenidiales, Leptomitales, Myzocytiopsidales, Olpidiopsidales, Peronosporales, Pythiales, Rhipidiales, Saprolegniales, and Sclerosporales.

[0166] Plant pathogens belonging to the phylum Endomyxa, including various orders such as Haplosporida, Paradiniida, Paramyxida, Gromiida, Phagomyxida, Plasmodiophorida, and Vampyrellida.

[0167] Plant pathogens belonging to the phylum Olpidiomycota and order Olpidiales.

[0168] Plant pathogens belonging to the phylum Ascomycota, including various orders such as Cladosporiales, Diaporthales, Erysiphales, Glomerellales, Helotiales, Hypocreales, Magnaporthales, Mycosphaerellales, Myriangiales, Pleosporales, and Venturiales.

[0169] Plant pathogens belonging to the phylum Basidiomycota, including various orders such as Agaricales, Cantharellales, Pucciniales, and Ustilaginales.

[0170] Plant pathogens belonging to the phylum Blastodactylomycota and the order Physodermatales, etc.

[0171] Specific examples of the aforementioned plant pathogens include the following examples.

[0172] Phytophthora species, including *Phytophthora infestans* (potato or tomato wilt), *Phytophthorapalmivora* (fig wilt), *Phytophthora cactorum* (pear or strawberry wilt), *Phytophthora capsici* (winter melon, pumpkin, sweet pepper or chili pepper wilt), *Phytophthora capsici* (tomato gray wilt), *Phytophthora capsici* (eggplant or watermelon brown rot wilt), *Phytophthora citricola* (citrus brown rot wilt), *Phytophthora vignae f. sp. adzukicola* (red bean stem wilt), *Phytophthoramegasperma var. sojae* (edamame stem wilt), and *Phytophthora porri* (onion or wild garlic white wilt); and *Pseudoperonospora* (cucumber, pumpkin, melon, zucchini downy mildew). *Pseudoperonospora* fungi, such as *Pseudoperonospora humuli*, *Plasmopara* fungi, such as *Plasmopara viticola*, *Plasmopara nivea*, *Hyaloperonospora* fungi, such as *Hyaloperonospora brassicae*, *Bremia* fungi, such as *Bremia lactucae*, *Pythium graminicola*, *Pythium iwayamai*, *Pythium aphanidermatum*, *Pythium zingiberis*, and *Pythium ultimum var.*, are pathogens affecting rice seedlings, wheat, and other plants.Fungi of the genus *Pythium* such as *Pythium* (the causal agent of root rot in radish); fungi of the genus *Aphanomyces* such as *Aphanomyces raphani* and *Aphanomyces cochlioides* (the causal agent of root rot in spinach); fungi of the genus *Albugo* such as *Albugo macrospora*, *Albugo wasabiae*, and *Albugo ipomoeae-aquaticae* (the causal agent of white rust in spinach, turnip, radish, or rapeseed); fungi of the genus *Peronospora* such as *Peronospora manshurica* (the causal agent of downy mildew in soybeans or edamame), *Peronospora parasitica* (the causal agent of downy mildew in broccoli or turnips), *Peronospora destructor* (the causal agent of downy mildew in scallions, shallots, or onions), *Peronospora farinosa f. sp. Spinaciae* (the causal agent of downy mildew in spinach), and *Peronospora belbahrii* (the causal agent of downy mildew in basil). .

[0173] Plasmodiophora fungi, such as Plasmodiophorabrassicae, which causes clubroot in Chinese cabbage, cabbage, cauliflower, rapeseed, broccoli, or turnip; Polymyxa fungi, such as Polymyxa betae, which transmits beet necrotic yellow vein virus; Spongospora fungi, such as Spongospora subterranea, which causes potato scab; and Olpidium fungi, such as Olpidium virulentus, which transmits Mirafiori lettuce bigvein virus.

[0174] Powdery mildew fungi such as *Erysiphe graminis* (wheat powdery mildew); fungi of the genus *Setosphaeria* such as *Setosphaeria turcica* (corn large leaf spot); fungi of the genus *Sphaerotheca* such as *Sphaerotheca fuliginea* (cucumber powdery mildew) and *Sphaerotheca humuli* (strawberry powdery mildew); fungi of the genus *Uncinula* such as *Uncinula necator* (grape powdery mildew); fungi of the genus *Podosphaera* such as *Podosphaera leucotricha* (apple powdery mildew); fungi of the genus *Mycosphaerella pinodes* (pea brown spot causal agent); fungi of the genus *Mycosphaerella pomi* (apple black spot causal agent); fungi of the genus *Mycosphaerella musicola* (banana black streak leaf spot causal agent); fungi of the genus *Mycosphaerella nawae* (persimmon round spot leaf drop causal agent); fungi of the genus *Mycosphaerella* (strawberry snake eye causal agent). Mycosphaerella species such as *Fragariae*; Venturia species such as *Venturia inaequalis* and *Venturia nashicola*; Pyrenophora species such as *Pyrenophora teres* and *Pyrenophora graminea*; and Sclerotinia species such as *Sclerotinia sclerotiorum* (pathogenic to beans, cucumbers, cabbage, bok choy, peppers, sweet peppers, or onions), *Sclerotinia borealis* (pathogenic to wheat), *Sclerotinia minor* (pathogenic to tomatoes), and *Sclerotinia trifoliorum* (pathogenic to alfalfa).

[0175] The following fungi are affected: *Botryotinia*, the causal agent of peanut sclerotium rot; *Cochliobolus*, the causal agent of rice leaf spot (such as *Cochliobolus miyabeanus*); *Didymella*, the causal agent of cucumber anthracnose; *Gibberella*, the causal agent of rice bakanae disease; *Elsinoe*, the causal agent of grape black rot and citrus scab; *Diaporthe*, the causal agent of citrus black spot and grape branch swelling; *Monilinia mali*, the causal agent of apple blossom rot; and *Monilinia*, the causal agent of peach brown rot. Fungi of the genus *Monilinia*, such as *fructicola*; fungi of the genus *Glomerella*, such as *Glomerella cingulata*, which cause late rot of grapes.

[0176] Rice sheath blight pathogen (Rhizoctonia solani) and other Rhizoctonia species; wheat loose smut pathogen (Ustilago nuda) and other Ustilago species; oat crown rust pathogen (Puccinia coronata), wheat leaf rust pathogen (Puccinia recondita), wheat stripe rust pathogen (Puccinia striiformis) and other Puccinia species; soybean rust pathogen (Phakopsora pachyrhizi) and other Phagostomium species; wheat or barley snow rot sclerotium (Typhula incarnata or Typhulaishikariensis) and other Typhula species.

[0177] Septoria species, such as *Septoria nodorum* and *Septoria tritici*, are pathogens causing wheat glume blight; Botrytis species, such as *Botrytis cinerea*, *Botrytis allii*, and *Botrytis squamosa*, *Botrytis byssoidea*, or *Botrytis tulipae*, are pathogens causing leaf blight in onions; Fusarium species, such as *Fusarium graminearum* and *Fusarium oxysporum*, are pathogens causing rice blast. Fungi of the genus *Pyricularia* such as *oryzae*; fungi of the genus *Cercospora* such as *Cercospora beticola* and *Cercosporakakivora*; fungi of the genus *Colletotrichum* such as *Colletotrichum orbiculare* and *Colletotrichum coffeanum*; fungi of the genus *Alternaria* such as *Alternaria alternata* apple pathotype, *Alternaria alternata* Japanese pear pathotype, *Alternaria solani* potato early blight or tomato ring rot, *Alternaria brassicae* cabbage or Chinese cabbage black spot, *Alternaria brassicicola* cabbage black mold, and *Alternaria porri* onion or scallion black spot; fungi of the genus *Phoma* cabbage root rot. Phona fungi such as *Pseudocercosporella* (wheat eye spot fungus); Pseudocercosporella fungus such as *Pseudocercosporella herpotrichoides*; Pseudocercosporora fungus such as *Pseudocercosporora vitis*.The following fungi are included: *Rhynchosporium secalis*, the causal agent of barley cloud spot; *Cladosporium carpophilum*, the causal agent of peach black spot; *Phomopsis*, the causal agent of peach rot; *Gloeosporium kaki*, the causal agent of persimmon anthracnose; *Fulvia*, the causal agent of tomato leaf mold; *Corynespora*, the causal agent of cucumber brown spot; and *Physoderma maydis*, the causal agent of corn spot.

[0178] Compound (I) is effective against the aforementioned plant pathogens, thus providing preventative or therapeutic control of various diseases. In particular, Compound (I) is effective against a variety of diseases that are problems in the agricultural and horticultural fields, including, for example, rice diseases such as damping-off caused by *Pythium*, rice blast caused by *Pyrophyllus*, seedling blight caused by *Fusarium*, sesame leaf spot caused by *Cyclocarya paliurus*, and sheath blight caused by *Rhizoctonia solani*; wheat diseases such as powdery mildew caused by *Pythium*, Fusarium head blight or crown rot caused by *Fusarium*, rust caused by *Sterilaria*, brown snow rot caused by *Pythium*, loose smut caused by *Ustilago maydis*, eye spot caused by *Pseudoceros*, and leaf blight or glume blight caused by *Syndromea*; and Fusarium head blight caused by *Fusarium*, leaf spot caused by *Agrotyphae*, rust caused by *Sterilaria*, and *Sterilaria pubescens*. Diseases of corn caused by fungi, such as large leaf spot caused by *Cyclocarya paliurus*, sesame leaf spot caused by *Cyclocarya paliurus*, root rot caused by *Pythium*, and smut caused by *Ustilago maydis*; diseases of gramineous crops such as smut caused by *Ustilago maydis*, leaf burn caused by *Polyspora spp.*, rust caused by *Pseudomonas spp.*, top rot caused by *Fusarium graminearum*, sooty mold caused by *Cyclocarya spp.*, and leaf blight caused by *Pseudocactus spp.*; diseases of leguminous crops such as powdery mildew caused by *Pseudomonas spp.*, rust caused by *Pseudomonas spp.*, downy mildew caused by *Pythium spp.*, blight or stem blight caused by *Phytophthora spp.*, anthracnose caused by *Pseudomonas spp.*, sclerotinia rot caused by *Sclerotinia sclerotiorum*, gray mold caused by *Botrytis cinerea*, and root rot or damping-off caused by *Fusarium spp.*; diseases of leguminous crops caused by *Fusarium spp.* Diseases of cruciferous crops including wilt caused by spore-forming fungi, downy mildew caused by *Peronospora* or *Peronospora* species, black spot caused by *Alternaria*, root rot caused by *Stemona*, clubroot caused by *Plasmodium*, root constriction caused by *Hymenium*, and Pythium rot caused by *Pythium*; diseases of Asteraceae crops including downy mildew caused by *Plasmodium*, blight caused by *Phytophthora*, gray mold caused by *Botrytis*, sclerotinia rot caused by *Sclerotinia*, and rust caused by *Russula*; and diseases of Asteraceae crops including ring spot caused by *Alternaria*, leaf mold caused by *Bryophyta*, blight or gray blight caused by *Phytophthora*, gray mold caused by *Botrytis*, powdery mildew caused by *Pyrophyta*, wilt caused by *Fusarium*, and *Pseudomonas*. Diseases of tomatoes such as anthracnose caused by *Alternaria*; diseases of potatoes such as early blight caused by *Alternaria*, blight or brown rot caused by *Phytophthora*, sclerotinia rot caused by *Sclerotinia*, and dry rot caused by *Fusarium*; diseases of cucurbit crops such as anthracnose caused by *Anthracnose*, powdery mildew caused by *Monoclonus*, vine blight caused by *Subspora*, downy mildew caused by *Pseudomonas*, blight or brown rot caused by *Phytophthora*, brown spot caused by *Clostridium*, and wilt caused by *Fusarium*; diseases of Amaryllidaceae (Allium genus) crops such as downy mildew caused by *Phytophthora*, gray mold caused by *Botrytis*, sclerotinia rot caused by *Sclerotinia*, and rust caused by *Russula*.Diseases of Apiaceae crops, including downy mildew caused by *Monopoda*, 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 leaf spot caused by *Cercospora*; diseases of Liliaceae crops, including leaf blight caused by *Botrytis*, blight caused by *Phytophthora*, and stem blight caused by *Pseudomonas*; diseases of Polygonaceae crops, including downy mildew caused by *Peronospora*, powdery mildew caused by *Erysiphe*, and damping-off caused by *Rhizoctonia*; diseases of Convolvulaceae crops, including white rust caused by *White Rust*, wilt caused by *Fusarium*, black spot caused by *Trichoderma*, and damping-off caused by *Streptomyces*; and root rot caused by *Hymenopterus* and white rust caused by *White Rust*. Diseases of Chenopodiaceae crops, including downy mildew caused by *Phytophthora*, blight caused by *Phytophthora*, gray mold caused by *Botrytis*, sclerotinia rot caused by *Sclerotinia*, powdery mildew caused by *Pyrophyllus*, and brown spot caused by *Cercospora*; diseases of Vitaceae crops, including black rot caused by *Cercospora*, late rot caused by *Anthracnose*, powdery mildew caused by *P.*, downy mildew caused by *Monochoria*, gray mold caused by *Botrytis*, brown spot caused by *P.*, and branch swelling caused by *C.*; diseases of strawberries, including powdery mildew caused by *Monochoria*, gray mold caused by *Botrytis*, anthracnose caused by *C.*, and dry rot caused by *Fusarium*; and flower rot caused by *Sclerotium* and powdery mildew caused by *Symplocos*. Diseases of apples including leaf spot caused by *Alternaria*, black spot caused by *Aureobasidium*, anthracnose caused by *Microcystis*, brown spot caused by *Dioscorea*, ring spot caused by *Botrytis*, sooty mold caused by *Zygophiala*, sooty mold caused by *Gloeodes*, and black spot caused by *Cyclocarya*; diseases of pears including black spot caused by *Aureobasidium*, black spot caused by *Alternaria*, powdery mildew caused by *Syngonium*, blight caused by *Phytophthora*, and fruit rot caused by *Fusarium*; diseases of peaches including brown rot caused by *Cladosporium*, black spot caused by *Cladosporium*, and *Pseudomonas* rot; and diseases of Rosaceae crops including those caused by *Cyclocarya*, black spot caused by *Cladosporium*, and *Pseudomonas* rot. Diseases of citrus and other Rutaceae crops, including black spot disease caused by *Fusarium*, scab disease caused by *Fusarium*, and damping-off disease caused by *Fusarium*; diseases of persimmon and other Dioscoreaceae crops, including anthracnose caused by *Palmaria*, leaf drop caused by *Cercospora*, powdery mildew caused by *Syngonium*, and sooty mold caused by *Zygophiala*; diseases of Theaceae crops, including anthracnose caused by *Anthracnose*, ring spot disease caused by *Polytrichum*, red scorch caused by *Pseudomonas*, and cake disease caused by *Exobasidiomycetes*; diseases of gingeraceae crops, including root and stem rot caused by *Pythium*; diseases of Cannabisaceae crops, including downy mildew caused by *Pseudomonas*; and diseases of Lamiaceae crops, including downy mildew caused by *Peronospora*.

[0179] In addition, it is also effective against the following seed-borne infectious diseases: wheat diseases such as Fusarium head blight or crown rot caused by Fusarium, anthracnose caused by Anthracnose, smut caused by Ustilago maydis, loose smut caused by Ustilago maydis, leaf streak caused by Cephalosporium, and glume blight caused by Phytosporium; corn diseases such as sesame leaf spot caused by Helicobacter pylori, anthracnose caused by Anthracnose, and seedling blight caused by Fusarium; sugarcane diseases such as red rot caused by Microsclerosis, black rot caused by Microsclerosis, and downy mildew caused by Phytosporium; and diseases of gramineous crops such as purple blotch caused by Cercospora, downy mildew caused by Downy mildew, and Fusarium... Diseases of leguminous crops, including damping-off caused by *Alternaria*, brown spot caused by *Syndromea*, black spot caused by *Syndromea*, anthracnose caused by *Amanita*, and dormancy disease caused by *Septogloeum*; diseases of cabbage, including black spot or sooty mold caused by *Alternaria*, downy mildew caused by *Peronospora*, bacterial black spot caused by *Pseudomonas*, black rot caused by *Xanthomonas*, and root rot caused by *Stemona*; diseases of radish, including black spot caused by *Alternaria*, wilt caused by *Fusarium*, and black rot caused by *Xanthomonas*; and diseases of radish caused by *Alternaria* and *Xanthomonas*. Diseases of cruciferous crops such as black rot and yellowing caused by Verticillium; diseases of tomatoes such as ring spot caused by Alternaria, canker caused by Corynebacterium, and bacterial spot caused by Xanthomonas; diseases of eggplants such as brown spot caused by Alternaria and brown streak caused by Pseudomonas; diseases of solanaceous crops such as scab caused by Streptomyces, silver spot caused by Helicobacter pylori, and powdery scab caused by Pseudomonas; diseases of cucurbitaceous crops such as black spot caused by Alternaria, bacterial spot caused by Pseudomonas, and bacterial brown spot caused by Xanthomonas; diseases of cucumbers such as Alternaria... Diseases of Amaryllidaceae (Allium genus) crops such as black spot caused by fungi, gray rot or mycelial rot caused by Botrytis cinerea, dry rot caused by Fusarium spp., downy mildew caused by Pythium spp., and white blight or stem blight caused by Phytophthora spp.; diseases of carrots such as black leaf blight or black spot caused by Alternaria alternata and spot bacterial disease caused by Xanthomonas spp.; diseases of celery such as leaf blight caused by Phytosporum spp., sclerotinia spp., and leaf blight bacterial disease caused by Pseudomonas spp.; and diseases of Chenopodiaceae (Chenopodiaceae) crops such as downy mildew caused by Pythium spp., wilt caused by Fusarium spp., and anthracnose caused by Anthracnose.

[0180] Furthermore, it is also effective in preventing and controlling soil diseases caused by plant pathogens such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodium, and Leuconostoc.

[0181] Compound (I) can preventively or therapeutically control the various diseases described above. Using the test methods described in the examples below, the specified compounds of the present invention can exert excellent preventive or therapeutic effects at low dosages (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).

[0182] Compound (I) has excellent rain resistance, residual effect and wettability. Therefore, by applying compound (I) to plants, it can prevent harmful fungi on the above-ground parts of plants for a certain period of time.

[0183] To prevent and control various harmful plant diseases, an effective amount of compound (I) can be applied to the plant, plant pathogens, or soil.

[0184] The above-mentioned effective amount refers to the amount of compound (I) applied when compound (I) exerts its preventive and control effect on various harmful plant diseases.

[0185] The above-mentioned plant body refers to the above-ground parts of a plant, such as the trunk, stem, leaves, flowers, spikes, and fruits; the underground parts of a plant, such as tubers, rhizomes, and roots; and the seeds, seedlings, and transplanted seedlings of a plant.

[0186] The aforementioned soils refer to farmland such as dry fields, paddy fields, and orchards, as well as non-farmland such as lawns and forests, which are used for plant cultivation.

[0187] There are no particular restrictions on the plants to which compound (I) can be applied, as long as they are useful in agriculture and horticulture. Examples include: Gramineae crops (rice, wheat, barley, oats, rye, corn, sugarcane, etc.), Leguminosae crops (soybeans, kidney beans, red beans, peas, peanuts, edamame, alfalfa, etc.), Cruciferae crops (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, rapeseed, European 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, winter melon, zucchini, etc.), Amaryllidaceae Allium crops (scallions, leeks, garlic, onions, shallots, etc.), Apiaceae crops (celery, carrots, parsley, duckweed, etc.), Liliaceae crops (lilies, tulips, etc.). Asparagus, Polygonaceae (buckwheat, etc.), Convolvulaceae (sweet potato, water spinach, etc.), Chenopodiaceae (spinach, beet, etc.), Vitaceae (grapes, etc.), Rosaceae (rose, strawberry, apple, pear, peach, loquat, almond, etc.), Rutaceae (mandarin orange, lemon, orange, citrus, etc.), Ebenaceae (persimmon, etc.), Moraceae (fig, etc.), Theaceae (tea, etc.), Oleaceae (olive, jasmine, etc.), Malvaceae (cotton, cocoa, okra, etc.), Musaceae (banana, etc.), Zingiberaceae (ginger, myoga, etc.), Cannabisaceae (hops, etc.), Lamiaceae (basil, etc.), Rubiaceae (coffee tree, etc.), Bromeliaceae (pineapple, pineapple, etc.), Plumeriaceae (starflower, etc.), Caryophyllaceae (carnation, etc.), Violaceae (pansy, etc.).

[0188] The aforementioned plants include plants cultivated using transgenic technology and gene editing technology, such as plants endowed with environmental stress tolerance, herbicide tolerance, pest tolerance, disease tolerance, etc., or plants whose growth, reproductive traits, product quality, yield, etc., have been altered.

[0189] Regarding compound (I), it is commonly mixed with excipients to form formulations in various forms, such as powders, granules, water-dispersible granules, wettable powders, aqueous suspensions, oil suspensions, water-soluble powders, emulsions, liquids, ointments, aerosols, micro-dispersible agents, and microcapsules. However, as long as it meets the objectives of this invention, it can be formulated into all formulation forms commonly used in this field. Examples of excipients used in formulations include solid carriers and liquid carriers; surfactants and other formulation excipients may also be added as needed.

[0190] Specific examples of the aforementioned solid carriers include diatomaceous earth, quicklime, calcium carbonate, talc, white carbon graphite, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite, starch, and micronized silica.

[0191] Specific examples of the aforementioned liquid carriers 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 alcohols.

[0192] Examples of surfactants mentioned above include fatty acid salts, benzoates, alkyl sulfonyl succinates, dialkyl sulfonyl succinates, polycarboxylate salts, alkyl sulfates, alkyl sulfates, alkyl aryl sulfates, alkyl diethylene glycol ether sulfates, alcohol sulfates, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates, alkyl aryl phosphates, styrene aryl phosphates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl aryl ether phosphates, polyoxyethylene alkyl aryl ether sulfates, and polyoxyethylene alkyl aryl ether sulfates. Anionic surfactants and spreading agents such as alkyl ether phosphates, polyoxyethylene alkyl aryl phosphates, and salts of naphthalene sulfonic acid formaldehyde condensates; and nonionic surfactants and spreading agents such as sorbitol fatty acid esters, fatty acid glycerides, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, alkynyl glycols, alkynyl alcohols, oxidized olefin block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene styrene aryl ethers, polyoxyethylene glycol alkyl ethers, polyethylene glycol, polyoxyethylene fatty acid esters, polyoxyethylene sorbitol fatty acid esters, polyoxyethylene glycerol fatty acid esters, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid esters.

[0193] Other examples of pharmaceutical adjuvants include vegetable oils and mineral 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; organosilicon; and xanthan gum.

[0194] As long as they do not exceed the purpose of this invention, one or more of these additives may be appropriately selected and used. In addition to the additives mentioned above, substances known in the art may also be appropriately selected and used, such as extenders, thickeners, antisettling agents, antifreeze agents, dispersing stabilizers, antidote remedies, and fungicides, etc., which are commonly used additives. The mixing ratio of compound (I) with various additives is generally 0.001:99.999 to 95:5 by weight, and preferably 0.005:99.995 to 90:10. In the actual use of these formulations, they can be used directly or diluted to a specified concentration with a diluent such as water, and various spreading agents (surfactants, vegetable oils, mineral oils, etc.) can be added as needed.

[0195] The application of compound (I) varies depending on meteorological conditions, formulation form, target crop, application time, application location, type and occurrence of harmful plant diseases, and cannot be generalized. However, it can generally be applied using common methods such as dispersal, soil treatment, and seed treatment. When applying an effective amount of compound (I) using common methods, the effective ingredient concentration can be 0.1 to 10,000 ppm, preferably 1 to 2,000 ppm, and more preferably 1 to 1,000 ppm.

[0196] In general application methods, a composition containing compound (I) as an active ingredient (hereinafter also referred to as the "composition") or a dilution thereof may be applied. Generally, in the case of dispersal treatment, the appropriate application amount is approximately 10 to 100,000 g of the composition per hectare. In the case of soil treatment, the appropriate application amount is approximately 0.01 to 1,000 g of the composition per hectare. In the case of seed treatment, the appropriate application amount is approximately 0.001 to 100 g, preferably 0.01 to 1 g, per kg of seeds.

[0197] The above-described dispersal treatment is a method of preventing plant pathogens by dispersing an effective amount of this composition onto the surface of the plant's trunk, buds, stems, leaves, flowers, spikes, or fruits, or onto the plant's surface. Examples include dispersal onto stems and leaves, and dispersal onto the trunk.

[0198] The above-described soil treatment is a method of treating soil with this composition to protect crops from plant pathogens and to allow an effective amount of compound (I) to penetrate and move into the interior of the plant from the roots. Examples include irrigation treatment (irrigating the soil in which the composition is grown), soil mixing treatment (mixing the composition with the soil in which the composition is grown), planting hole treatment, treatment of the roots of plants or between plants (spreading or irrigation), and mixing treatment of soil used in mounds, seedling boxes, seedling trays, paper pots or seedbeds, etc.

[0199] The above-mentioned seed treatment is a method of protecting crops from plant pathogens by directly treating or treating nearby seeds, bulbs, etc., with this composition to prevent and control plant pathogens. Examples include coating treatment, powder coating treatment, and immersion treatment.

[0200] In addition, examples include seedling treatment (drenching or soaking), soaking treatment of bulbs, tubers, bulbs, roots, etc., and hydroponic treatment such as mixing in hydroponic nutrient solution. Treatment can be applied to the whole plant or a part of it (stems, leaves, buds, flowers, spikes, fruits, trunks, seeds, bulbs, tubers, bulbs, roots, etc.).

[0201] This composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural agents, fertilizers, antidotes, etc., and in such cases, it sometimes shows superior effects and efficacy.

[0202] The term "mixed use" or "combined use" refers to using this composition simultaneously, separately, or with time intervals between it and other ingredients.

[0203] Other agricultural and horticultural agents include herbicides, insecticides, acaricides, nematicides, soil pest control agents, fungicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators. In particular, mixed fungicide compositions, which combine this composition with one or more active ingredient compounds of other fungicides, sometimes improve the application range, treatment timing, and control activity in a preferred direction. It should be noted that this composition and the active ingredient compounds of other fungicides can be used by mixing separately formulated substances during dispersal, or they can be formulated together for use. Such mixed fungicides are also included in this invention.

[0204] The mixing ratio of compound (I) and other active ingredient compounds of fungicides varies depending on meteorological conditions, formulation form, target crop, application time, application location, type and occurrence of harmful plant diseases, etc., and cannot be generalized. By weight, it can generally be set to 1:300 to 300:1, preferably 1:100 to 100:1. Furthermore, as an appropriate application amount, the total amount of active ingredient compounds per hectare can be set to 0.1 to 70,000 g, preferably 1 to 30,000 g. This invention also includes a method for controlling harmful plant diseases by applying such a mixed fungicide composition.

[0205] When applying this composition, other agricultural and horticultural agents such as fungicides, insecticides, acaricides, nematicides, soil pest control agents, antiviral agents, attractants, herbicides, and plant growth regulators can also be added.

[0206] The active ingredient compounds (generic names) of the fungicides in the other agricultural and horticultural agents mentioned above can be appropriately selected from, for example, the following group of compounds. Even if not specifically stated otherwise, these compounds are included in the presence of various structural isomers such as salts, alkyl esters, and optical isomers.

[0207] Aniline pyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Triazole and benzothiazole compounds, such as tricyclazole; Aminopyridine compounds such as fluazinam; Triadimefon, bifenthrinol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole Azole compounds such as oxpoconazole fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipfentrifluconazole, and mefentrifluconazole; Quinoxaline compounds such as chinomethionat; Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, and thiram. Organochlorine compounds such as tetrachlorophthalide, chlorothalonil, and quintozene; Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, and fuberiazole; Cymoxanil and other cyanoacetamide compounds; Metalaxyl (Mefenoxam), Metalaxyl-M (Mefenoxam) Acyl amino acid compounds such as oxadixyl, ofuramide, benalaxyl, benalaxyl-M (also known as kiralaxyl, chiralaxyl), furaxyl, and valifenalate; Acetanilide compounds such as cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, and piraziflumid; Sulfonamide compounds such as dichlofluanid; Copper compounds such as copper hydroxide, oxine copper, anhydrous copper sulfate, copper nonylphenol sulfonate, 8-hydroxyquinoline copper, and diethylenediamine copper sulfonate (II) (also known as DBEDC); Organophosphorus compounds such as aluminum fosetyl-Al, tolclofos-Methyl, edifenphos, and iprobenfos; Phthalate compounds such as captan, captafol, and folpet; Dicarboxymidone compounds such as procymidone, iprodione, and vinclozolin; Fluorolanil, mepronil, benodanil, fluorinated fungicides N-benzoylaniline compounds such as azole (flufenoxadiazam); Amide compounds such as carpropamid, diclocymet, silthiofam, and fenoxanil; Pyrazole carboxamide compounds such as benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furamepyr, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, sedaxane, isoflucypram, inpyrfluxam, pyrapropoyne, and fenopyramid; Benzamide compounds such as fluopicolide, fluopyram, zoxamide, and fluopimomide; Furanyl aniline compounds such as fenfuram; Thiophene amide compounds such as isofetamid; Piperazine compounds such as triforine; Pyrifenox, pyridaben Pyridine compounds such as pyrisoxazole and aminopyrifen; Pyrimidine compounds such as fenarimol, ferimzone, nuarimol, and flumetylsulforim; Piperidine compounds such as fenpropidin; Morpholine compounds such as fenpropimorph and tridemorph; Organotin compounds such as fentin hydroxide and fentin acetate; Urea compounds such as pencycuron; 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; Methoxyacrylate compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, fenaminstrobin, flufenoxystrobin, triclopyricarb, and mandestrobin; Like famoxadone and oxathiapiprolin. azole compounds; Thiazole carboxamide 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; 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; Tetraazole compounds such as picarbutrazox and metyltetraprole; Sulfonamide compounds such as amisulbrom and cyazofamid; Allyl phenyl ketone compounds such as metrafenone and pyriofenone; Benzothiazolium compounds such as probenazole and dichlobentiazox; Phenylene pyrazole compounds such as fenpyrazamine; Dithiopentane compounds like isoprethiolane; Picoline amide compounds such as fenpicoxamid and florylpicoxamid; Sulfur, sulfur compounds such as lime sulfur; Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam-sodium, proquinazid, spiroxamine, and dipymetitrone. Microbial bactericides such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, and Trichoderma atroviride SKT-1; and Plant extracts such as tea tree oil.

[0208] The active ingredient compounds (generic names) of the other agricultural and horticultural pesticides, including insecticides, nematicides, acaricides, or soil pest control agents, can be appropriately selected from the following group of compounds. Even if not specifically stated otherwise, these compounds are included in the presence of various structural isomers such as salts, alkyl esters, and optical isomers.

[0209] Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenyl phenylphosphonothioate)), diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton Isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanochlor Organophosphate compounds such as phos, trichlorfon, methidathion, phenthoate, oxydeprofos (ESP), azinphos-methyl, fenthion, heptenophos, parathion, phosphocarb, demeton-S-methyl, monocotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, and phorate; Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC (3,5-xylyl methylcarbamate), and fenothiocarb are all carbamate compounds. Cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan are all derivatives of nereistoxin. Organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, and methoxychlor; Organometallic compounds such as fenbutatin oxide and cyhexatin; Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin, deltamethrin, cyhalothrin, gamma-cyhalothrin In), lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, ethofenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acridine lactate, allethrin, tau-fluvalinate, tralomethrin, proflu... Pyrethroid compounds such as thrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin, silafluofen, and chloroprallethrin; 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; Compounds such as pyridaben; Pyrazole compounds such as fenpyroximate, fipronil, ethiprole, acetoprole, pirafluprole, pyriprole, cyenopyrafen, and flufiprole. Pyrazole carboxamide compounds such as pyflubumide, tebufenpyrad, tolfenpyrad, and dimpropyridaz; Pyridylpyrazole compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraliliprole, tyclopyrazoflor, fluchlordiniliprole, and tiorantraniliprole. Neonicotinic 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; Quaternary keto acid compounds such as spirodiclofen, spiromesifen, and spirobudifen; Tetram acid compounds such as spirotetramat and spiropidion; Methoxyacrylate compounds such as fluacrypyrim, pyriminostrobin, and flupyroxystrobin; Pyrimidine amine compounds such as flufenerim and pyrimidifen; Organosulfur compounds such as malathion; Triazine compounds such as cyromazine; Hydrazone compounds such as hydramethylnon; Diamide compounds such as flubendiamide, broflanilide, cyhalodiamide, pioxaliprole, and piperflanilide; Thiourea compounds such as diafenthiuron and chloromethiuron; Amitraz, chlordimeform, and chloromebuform are formamidin compounds; Pyridine azomethyl compounds such as pymetrozine and pyrifluquinazone; Afoxolaner, Fluralaner, Fluor Fluxametamide, sarolaner Isoflualanam, a type of... Azoline compounds; Other compounds mentioned include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, and amidoflumet. ), sulfluramid, hydramethylnon, metaldehyde, sulfoxaflor, fluensulfone, verbutin, dicloromezotiazine, triflumezopyrim, fluhexafon, tioxazafen, afidopyropen, fometoquin, flupyradifurone, fluazaindolizine, acynonapyr, pyrimifen benzpyrimoxan, flupyrimin Compounds such as oxazosulfyl, sulfiflumin, bisulflufen, cybenzoxasulfyl, galquin, vedescana, tiapyrachlor, and bentioflumin.

[0210] In addition, this composition can be used in combination with the following compounds.

[0211] Microbial pesticides such as crystalline protein toxins, insect pathogen viruses, insect pathogen filamentous agents, and nematode pathogen filamentous agents produced by Bacillus thuringiensis, including Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, and Bacillus thuringiensis tenebrionis. Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, and spintoram; Natural substances such as azadirachtin, rotenone, and ryanodine; Repellents like DEET; Physical repellents such as paraffin oil and mineral oil; RNAi pesticides like ledprona and vadescana.

[0212] Preferred embodiments of the present invention are shown below. However, the present invention is not limited to these.

[0213] [1] The compound or its salt represented by formula (I).

[0214] [2] According to the compound or its salt described in [1] above, the compound of formula (I) is an N-(cyclo)alkoxyamide compound of formula (IA) or an N-alkynyloxyamide compound of formula (IB).

[0215] [3] According to the compound or its salt described in [1] above, the compound of formula (I) is an N-(cyclo)alkoxyamide compound of formula (IA).

[0216] [4] According to the compound or its salt described in [1] above, the compound of formula (I) is an N-alkynyl oxyamide compound of formula (IB).

[0217] [5] According to the compound or its salt described in [1] above, X 1 It consists of fluorine, chlorine, or bromine atoms.

[0218] [6] According to the compound or its salt described in [1] above, X 1 It consists of fluorine or chlorine atoms.

[0219] [7] According to the compound or its salt described in [1] above, X 1 It consists of fluorine or bromine atoms.

[0220] [8] According to the compound or its salt described in [1] above, X 1 It consists of chlorine or bromine atoms.

[0221] [9] According to the compound or its salt described in [1] above, X 1 It is a fluorine atom.

[0222]

[10] According to the compound or salt thereof described in [1] above, X 1 It is a chlorine atom.

[0223]

[11] According to the compound or its salt described in [1] above, X 1 It is a bromine atom.

[0224]

[12] According to any one of [1], [5] to

[11] above, R 1 For can be T 1 Substituted (C1-C4)-alkyl, (C3-C4)-cycloalkyl, (C3-C5)-alkenyl, or (C3-C5)-ynyl.

[0225]

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

[11] above, R 1 It is (C1-C4)-alkyl, (C3-C4)-cycloalkyl, or (C3-C5)-alkynyl.

[0226]

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

[11] above, R 1 It can be methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, propargyl, allyl, methylthiomethyl, cyanomethyl, 2-methoxyethyl, 2,2-difluoroethyl, or methoxycarbonylmethyl.

[0227]

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

[11] above, R1 It can be methyl, ethyl, cyclopropyl, or propyne.

[0228]

[16] According to any one of [1], [5] to

[11] above, R 1 It can be methyl, ethyl, or cyclopropyl.

[0229]

[17] According to any one of [1], [5] to

[11] above, R 1 It can be methyl, ethyl, or propyne.

[0230]

[18] According to any one of [1], [5] to

[11] above, R 1 It can be methyl or ethyl.

[0231]

[19] According to any one of [1], [5] to

[11] above, R 1 It is methyl or cyclopropyl.

[0232]

[20] According to any one of [1], [5] to

[11] above, or a salt thereof, R 1 It is methyl or propargyl.

[0233]

[21] According to any one of [1], [5] to

[11] above, R 1 It is a methyl group.

[0234]

[22] According to any one of [1], [5] to

[11] above, or a salt thereof, R 1 It is an ethyl group.

[0235]

[23] According to any one of [1], [5] to

[11] above, R 1 It is cyclopropyl.

[0236]

[24] According to any one of [1], [5] to

[11] above, or a salt thereof, R 1 It is propargyl.

[0237]

[25] According to any one of [1], [5] to

[24] above, Y, a salt thereof 1 It can be a hydrogen atom, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

[0238]

[26] According to any one of [1], [5] to

[24] above, Y 1It can be halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, nitro, or cyano.

[0239]

[27] According to any one of [1], [5] to

[24] above, Y 1 It can be a hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl, trifluoromethyl, difluoromethyl, nitro, or cyano.

[0240]

[28] According to any one of [1], [5] to

[24] above, Y 1 It can be a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a difluoromethyl group, a nitro group, or a cyano group.

[0241]

[29] According to any one of [1], [5] to

[24] above, Y 1 It can be a fluorine atom, a chlorine atom, a bromine atom, or a methyl atom.

[0242]

[30] According to any one of [1], [5] to

[24] above, Y 1 It is a fluorine atom.

[0243]

[31] According to any one of [1], [5] to

[24] above, Y 1 It is a chlorine atom.

[0244]

[32] According to any one of [1], [5] to

[24] above, Y 1 It is a bromine atom.

[0245]

[33] According to any one of [1], [5] to

[24] above, Y 1 It is a methyl group.

[0246]

[34] According to any one of [1], [5] to

[33] above, Y 2 It can be a halogen, (C1-C6)-alkyl, or hydrogen atom.

[0247]

[35] According to any one of [1], [5] to

[33] above, Y 2 It can be a fluorine atom, a chlorine atom, a (C1-C3)-alkyl group, or a hydrogen atom.

[0248]

[36] According to any one of [1], [5] to

[33] above, Y 2 It can be a fluorine atom, a chlorine atom, a methyl atom, or a hydrogen atom.

[0249]

[37] According to any one of [1], [5] to

[33] above, Y 2 It consists of fluorine or hydrogen atoms.

[0250]

[38] According to any one of [1], [5] to

[37] above, Y 3 It can be a halogen, (C1-C6)-alkyl, or hydrogen atom.

[0251]

[39] According to any one of [1], [5] to

[37] above, Y 3 It can be a fluorine atom, a chlorine atom, a (C1-C3)-alkyl group, or a hydrogen atom.

[0252]

[40] According to any one of [1], [5] to

[37] above, Y 3 It can be a fluorine atom, a chlorine atom, a methyl atom, or a hydrogen atom.

[0253]

[41] According to any one of [1], [5] to

[37] above, Y 3 It consists of fluorine or hydrogen atoms.

[0254]

[42] According to any one of [1], [5] to

[41] above, Y 4 It can be a halogen or a hydrogen atom.

[0255]

[43] According to any one of [1], [5] to

[41] above, Y 4 It can be a fluorine atom, a chlorine atom, or a hydrogen atom.

[0256]

[44] According to any one of [1], [5] to

[41] above, Y 4 It consists of fluorine or hydrogen atoms.

[0257]

[45] According to any one of [1], [5] to

[44] above, Y 5 It can be a halogen or a hydrogen atom.

[0258]

[46] According to any one of [1], [5] to

[44] above, Y 5 It can be a fluorine atom, a chlorine atom, or a hydrogen atom.

[0259]

[47] According to any one of [1], [5] to

[44] above, Y 5 It consists of fluorine or hydrogen atoms.

[0260]

[48] ​​According to any one of [1], [5] to

[44] above, Y 5 It is a hydrogen atom.

[0261]

[49] The N-(cyclo)alkoxyamide compound or its salt shown in formula (IA).

[0262]

[50] According to the N-(cyclo)alkoxyamide compound or its salt described in

[49] above, Y 1 It can be halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

[0263]

[51] According to the N-(cyclo)alkoxyamide compound or its salt described in

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

[0264]

[52] According to the N-(cyclo)alkoxyamide compound or its salt described in

[49] above, Y 1 It can be a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a difluoromethyl group, a nitro group, or a cyano group.

[0265]

[53] According to any one of

[49] to

[52] above, the N-(cyclo)alkoxyamide compound or its salt, Y 2A It can be a hydrogen atom, a fluorine atom, or a chlorine atom.

[0266]

[54] According to any one of

[49] to

[52] above, the N-(cyclo)alkoxyamide compound or its salt, Y 2A It consists of hydrogen or fluorine atoms.

[0267]

[55] According to any one of

[49] to

[54] above, the N-(cyclo)alkoxyamide compound or its salt, Y 3A It can be a hydrogen atom, a fluorine atom, or a chlorine atom.

[0268]

[56] According to any one of

[49] to

[54] above, the N-(cyclo)alkoxyamide compound or its salt, Y 3A It consists of hydrogen or fluorine atoms.

[0269]

[57] According to any one of

[49] to

[56] above, the N-(cyclo)alkoxyamide compound or its salt, Y 4A It consists of hydrogen or fluorine atoms.

[0270]

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

[49] to

[57] above, R 1AIt can be methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, or cyclobutyl.

[0271]

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

[49] to

[57] above, R 1A It can be methyl, ethyl, or cyclopropyl.

[0272]

[60] The N-alkynyl oxyamide compound or its salt as shown in formula (IB).

[0273]

[61] According to the N-alkynyl oxyamide compound or its salt described in

[60] above, Y 5 It is a hydrogen atom.

[0274]

[62] According to the N-alkynyl oxyamide compound or its salt described in

[60] or

[61] above, Y 1 It can be halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

[0275]

[63] According to the N-alkynyl oxyamide compound or its salt described in

[60] or

[61] above, Y 1 It can be a fluorine atom, chlorine atom, bromine atom, methyl, difluoromethyl, nitro, or cyano group.

[0276]

[64] The N-alkynyl oxyamide compound or its salt according to any one of

[60] to

[63] above, Y 2 It can be a hydrogen atom or a halogen.

[0277]

[65] An N-alkynyl oxyamide compound or a salt thereof according to any one of

[60] to

[63] , Y 2 It consists of hydrogen or fluorine atoms.

[0278]

[66] According to any one of

[60] to

[65] above, the N-alkynyl oxyamide compound or its salt, Y 3 It can be a hydrogen atom or a halogen.

[0279]

[67] The N-alkynyl oxyamide compound or its salt according to any one of

[60] to

[65] above, Y 3 It consists of hydrogen or fluorine atoms.

[0280]

[68] The N-alkynyl oxyamide compound or its salt according to any one of

[60] to

[67] above, Y 4 It can be a hydrogen atom or a halogen.

[0281]

[69] According to any one of

[60] to

[67] above, the N-alkynyl oxyamide compound or its salt, Y 4 It consists of hydrogen or fluorine atoms.

[0282]

[70] The N-alkynyl oxyamide compound or its salt according to any one of

[60] to

[69] above, X 1 It can be a fluorine atom, a chlorine atom, or a bromine atom.

[0283]

[71] An agricultural and horticultural fungicide containing, as an active ingredient, any one of [1] to

[70] above.

[0284]

[72] A method for preventing and controlling harmful plant diseases, wherein an effective amount of any one of the compounds described in [1] to

[70] above, or a salt thereof, is applied to the plant, plant pathogen, or soil.

[0285] Example 1

[0286] The following describes embodiments of the present invention, but the present invention is not limited to these embodiments. The melting point, which is a physical property value of the compound of the present invention, was determined by Buchi M-565. 1 1H-NMR spectral data were obtained in the assay solvent using a JEOL JNM-ECX (500 MHz) or Bruker AVANCE III HD (300 MHz) spectroscopy (1H-NMR spectroscopy). It should be noted that the assay solvent sometimes also contains tetramethylsilane (TMS) as an internal standard.

[0287] In addition, in this instruction manual, room temperature refers to approximately 10~30℃.

[0288] [Synthesis example]

[0289] Synthetic Example 1: Synthesis of 2-amino-4-bromo-N-(2-chlorobenzyl)-N-methoxythiazole-5-carboxamide (Compound No. A-94)

[0290] (1) 2-Chlorobenzyl bromide (543 mg) and O-methylhydroxylamine hydrochloride (662 mg) were mixed in N,N-dimethylformamide (10 mL). Diisopropylethylamine (2.31 mL) was added to the resulting mixture at room temperature, and the mixture was stirred at 50 °C for 5 hours. After cooling 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 was extracted using an ethyl acetate-heptane mixture. The extracted organic layer was washed sequentially with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain an oily N-(2-chlorobenzyl)-O-methylhydroxylamine (266 mg). 1 The H-NMR spectral data are shown below.

[0291] 1 H 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).

[0292] (2) At room temperature, a solution of sodium dihydrogen phosphate (11.3 g) in tert-butanol (310 mL) of tert-butanol (based on Example 18, Step F, 9.7 g) of tert-butyl(4-bromo-5-formylthiazolyl-2-yl)carbamate (9.7 g) synthesized in Step F was added to Example 18 (page 56) and stirred to obtain a mixture. 2-Methyl-2-butene (43 mL) was added to the resulting mixture. After 15 minutes, a solution of sodium chlorite (21.4 g, 80%) in aqueous solution (50 mL) was added, and the mixture was stirred for 3.5 hours. Hydrochloric acid was added to the reaction solution to make it acidic, and then ethyl acetate was added for extraction. The extracted organic layer was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was dissolved in a saturated sodium bicarbonate aqueous solution, and the aqueous layer was washed with ethyl acetate. Hydrochloric acid was added to adjust the pH of the aqueous layer, which had been washed with ethyl acetate, to acidic pH. Ethyl acetate was then added to the acidified aqueous layer, and the aqueous layer was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 9.2 g of 2-[(tert-butoxycarbonyl)amino]-4-bromothiazol-5-carboxylic acid, a white solid. The... 1 The H-NMR spectral data are shown below.

[0293] 1 H NMR (DMSO-d6 / 300MHz): δ (ppm) = 13.36 (brs, 1H), 12.18 (s, 1H), 1.49 (s, 9H).

[0294] (3) Under ice-cooling, oxaloyl chloride (166 mg) and a catalyst amount of N,N-dimethylformamide were added to a tetrahydrofuran (10 mL) solution of 2-[(tert-butoxycarbonyl)amino]-4-bromothiazol-5-carboxylic acid (339 mg), 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 40 minutes. The reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-bromothiazol-5-carboxylic chloride. Tetrahydrofuran (5 mL) was added to the obtained acyl chloride to dissolve it. Then, a tetrahydrofuran (5 mL) solution of N-(2-chlorobenzyl)-O-methylhydroxylamine (150 mg) 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 a saturated sodium bicarbonate aqueous solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted using ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to give amorphous tert-butyl{4-bromo-5-[(2-chlorobenzyl)(methoxy)carbamoyl]thiazolyl-2-yl}carbamate (376 mg). 1 The H-NMR spectral data are shown below.

[0295] 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).

[0296] (4) Trifluoroacetic acid (1.2 mL) was added to a dichloromethane (6 mL) solution of tert-butyl{4-bromo-5-[(2-chlorobenzyl)(methoxy)carbamoyl]thiazolyl-2-yl}carbamate (376 mg), and the mixture was stirred under reflux overnight. After cooling to room temperature, a saturated sodium bicarbonate aqueous solution was slowly added to the reaction solution to adjust the pH to alkalinity. The aqueous layer of the alkaline reaction solution was extracted with ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain the target solid (208 mg). 1 The H-NMR spectral data and melting point are shown below.

[0297] 1H 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).

[0298] Melting point: 184.8℃

[0299] Synthetic Example 2: Synthesis of 2-amino-4-bromo-N-(4-fluoro-2-methylbenzyl)-N-methoxythiazole-5-carboxamide (Compound No. A-105)

[0300] (1) Triethylamine (0.5 mL) was added to a methanol (4 mL) solution of O-methylhydroxylamine hydrochloride (302 mg) at 0 °C and stirred to obtain a mixture. A methanol (6 mL) solution of 4-fluoro-2-methylbenzaldehyde (500 mg) and acetic acid (1 mL) were added sequentially to the mixture, and the temperature was raised to room temperature after 30 minutes. After 3.5 hours, 2-methylpyridineborane (774 mg) was added at 0 °C, followed by a 3N hydrochloric acid aqueous solution (6 mL) after 15 minutes, and the mixture was stirred for 2.5 hours to obtain a reaction solution. The reaction solution was adjusted to alkalinity by adding a saturated sodium bicarbonate aqueous solution, and methanol was removed by distillation. Ethyl acetate was added to the residue for extraction. The organic layer obtained by extraction was washed sequentially with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain an oily N-(4-fluoro-2-methylbenzyl)-O-methylhydroxyamine (392 mg). This substance... 1 The H-NMR spectral data are shown below.

[0301] 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).

[0302] (2) Under ice-cooling conditions, oxaloyl chloride (0.11 mL) and a catalyst amount of N,N-dimethylformamide were added to a tetrahydrofuran (10 mL) solution of 2-[(tert-butoxycarbonyl)amino]-4-bromothiazol-5-carboxylic acid (339 mg), 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 40 minutes. The reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-bromothiazol-5-carboxylic chloride. Tetrahydrofuran (5 mL) was added to the obtained acyl chloride to dissolve it. Then, a tetrahydrofuran (5 mL) solution of N-(4-fluoro-2-methylbenzyl)-O-methylhydroxylamine (148 mg) 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 a saturated sodium bicarbonate aqueous solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted using ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to give amorphous tert-butyl{4-bromo-5-[(4-fluoro-2-methylbenzyl)(methoxy)carbamoyl]thiazolyl-2-yl}carbamate (370 mg). 1 The H-NMR spectral data are shown below.

[0303] 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).

[0304] (3) Trifluoroacetic acid (1.2 mL) was added to a dichloromethane (6 mL) solution of tert-butyl{4-bromo-5-[(4-fluoro-2-methylbenzyl)(methoxy)carbamoyl]thiazolyl-2-yl}carbamate (370 mg), and the mixture was stirred under reflux overnight. After cooling to room temperature, a saturated sodium bicarbonate aqueous solution was slowly added to the reaction solution to adjust the pH to alkalinity. The aqueous layer of the alkaline reaction solution was extracted with ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain the target solid (262 mg). 1 The H-NMR spectral data and melting point are shown below.

[0305] 1H 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).

[0306] Melting point: 164.0℃

[0307] Synthetic Example 3: Synthesis of 2-amino-4-chloro-N-(2-fluorobenzyl)-N-(2-propynyloxy)thiazole-5-carboxamide (Compound No. B-55)

[0308] (1) 2-Fluorobenzyl bromide (500 mg) and O-2-propynylhydroxyamine hydrochloride (754 mg) synthesized based on Synthetic Example 1-2 as described on page 16 of U.S. Patent Application Publication No. 2014 / 0378399 were mixed with N,N-dimethylformamide (10 mL). Diisopropylethylamine (2.31 mL) was added to the resulting mixture at room temperature, and the mixture was stirred at 50 °C for 5 hours. After cooling 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 using an ethyl acetate-heptane mixture. The extracted organic layer was washed sequentially with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain an oily N-(2-fluorobenzyl)-O-(2-propynyl)hydroxyamine (69 mg). This substance... 1 The H-NMR spectral data are shown below.

[0309] 1 H NMR (CDCl3 / 300MHz): δ (ppm) = 7.38 (dt, 1H), 7.31-7.24 (m, 1H), 7.11 (dt, 1 H), 7.08-7.02(m, 1H), 6.02(t, 1H), 4.29(d, 2H), 4.18(d, 2H), 2.41(t, 1H).

[0310] (2) Under ice cooling, oxaloyl chloride (0.05 mL) and a catalyst amount of N,N-dimethylformamide were added to a tetrahydrofuran (5 mL) solution of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic acid (128 mg) synthesized in Experiment 5.1.10 as described on page 6177 of Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182. The mixture was stirred under a nitrogen atmosphere. After 10 minutes, the temperature was raised to room temperature and stirred for 1 hour. The reaction solution was concentrated under reduced pressure to give 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic chloride. The obtained acyl chloride was dissolved in tetrahydrofuran (2 mL). Then, a solution of N-(2-fluorobenzyl)-O-2-propynylhydroxyamine (69 mg) in tetrahydrofuran (3 mL) and diisopropylethylamine (0.13 mL) was 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 a saturated sodium bicarbonate aqueous solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted with ethyl acetate. The extracted organic layer was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain amorphous tert-butyl{4-chloro-5-[(2-fluorobenzyl)(2-propynyloxy)carbamoyl]thiazolyl-2-yl}carbamate (87 mg). 1 The H-NMR spectral data are shown below.

[0311] 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).

[0312] (3) Trifluoroacetic acid (0.3 mL) was added to a dichloromethane (1.5 mL) solution of tert-butyl{4-chloro-5-[(2-fluorobenzyl)(2-propynyloxy)carbamoyl]thiazolyl-2-yl}carbamate (87 mg), and the mixture was stirred overnight under reflux. After cooling to room temperature, a saturated sodium bicarbonate aqueous solution was slowly added to the reaction solution to adjust the pH to alkalinity. The aqueous layer of the alkaline reaction solution was extracted with ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain the target solid (55 mg). 1 The H-NMR spectral data and melting point are shown below.

[0313] 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).

[0314] Melting point: 154.1℃

[0315] Synthetic Example 4: Synthesis of 2-amino-4-chloro-N-(2,4-difluorobenzyl)-N-(2-propynyloxy)thiazole-5-carboxamide (Compound No. B-57)

[0316] (1) Triethylamine (0.5 mL) was added to a methanol (4 mL) solution of O-2-propynylhydroxyamine hydrochloride (389 mg) at 0 °C and stirred to obtain a mixture. A methanol (6 mL) solution of 2,4-difluorobenzaldehyde (514 mg) and acetic acid (1 mL) were added sequentially to the mixture, and the temperature was raised to room temperature after 30 minutes. After 3.5 hours, the mixture was cooled to 0 °C and 2-methylpyridineborane (967 mg) was added, followed by a 3N hydrochloric acid aqueous solution (7.2 mL) after 15 minutes. The mixture was stirred for 3 hours to obtain a reaction solution. A saturated sodium bicarbonate aqueous solution was added to the above reaction solution to make it alkaline, and methanol was removed by distillation. Ethyl acetate was added to the residue for extraction. The organic layer obtained by extraction was washed sequentially with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain an oily N-(2,4-difluorobenzyl)-O-2-propynylhydroxyamine (471 mg). This substance... 1 The H-NMR spectral data are shown below.

[0317] 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).

[0318] (2) Under ice-cooling, oxaloyl chloride (0.11 mL) and a catalyst amount of N,N-dimethylformamide were added to a tetrahydrofuran (10 mL) solution of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic acid (291 mg), 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 1 hour. The reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic chloride. Tetrahydrofuran (5 mL) was added to the obtained acyl chloride to dissolve it. Then, a tetrahydrofuran (5 mL) solution of N-(2,4-difluorobenzyl)-O-2-propynylhydroxyamine (172 mg) 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 a saturated sodium bicarbonate aqueous solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted using ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to give amorphous tert-butyl{4-chloro-5-[(2,4-difluorobenzyl)(2-propynyloxy)carbamoyl]thiazolyl-2-yl}carbamate (204 mg). 1 The H-NMR spectral data are shown below.

[0319] 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).

[0320] (3) A solution of tert-butyl{4-chloro-5-[(2,4-difluorobenzyl)(2-propynyloxy)carbamoyl]thiazolyl-2-yl}carbamate (204 mg) in dichloromethane (3.5 mL) was added to trifluoroacetic acid (0.69 mL), and the mixture was stirred under reflux overnight. After cooling to room temperature, a saturated sodium bicarbonate aqueous solution was slowly added to the reaction solution to adjust the pH to alkalinity. The aqueous layer of the alkaline reaction solution was extracted with ethyl acetate. The extracted organic layer was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (elution: ethyl acetate / heptane) to obtain the target solid (132 mg). 1 The H-NMR spectral data and melting point are shown below.

[0321] 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).

[0322] Melting point: 171.5℃

[0323] Next, representative examples of compound (I) are specifically illustrated in Tables 1-1 and 1-2. These compounds can be synthesized according to the manufacturing method and synthetic examples described above, as well as methods known in the art.

[0324] In the table, No. represents the compound No. . 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 column represent the following substituents: Me for methyl, Et for ethyl, n-Pr for n-propyl, i-Pr for isopropyl, c-Pr for cyclopropyl, t-Bu for tert-butyl, c-Bu for cyclobutyl, CN for cyano, and NO2 for nitro. In Table 1-1, = represents a double bond.

[0325] Furthermore, in the case of salts of compound (I), the remarks column in Tables 1-1 and 1-2 indicates the type of salt. For example, in the remarks column of Table 1-1, compounds listed as HCl salts are hydrochloride salts, compounds listed as TsOH salts are p-toluenesulfonates, and compounds listed as Na salts are sodium salts. For example, compound No. A-125 is the hydrochloride salt of compound No. A-20. Compound No. A-126 is the p-toluenesulfonate salt of compound No. A-20. Compound No. A-127 is the sodium salt of compound No. A-20.

[0326] In the remarks column of Tables 1-2, compounds listed as HCl salts are hydrochloride salts, compounds listed as TsOH salts are p-toluenesulfonates, and compounds listed as Na salts are sodium salts. For example, compound No. B-52 is the hydrochloride salt of compound No. B-2. Compound No. B-53 is the p-toluenesulfonate salt of compound No. B-2. Compound No. B-54 is the sodium salt of compound No. B-2.

[0327]

[0328] The physical properties of compound (I) synthesized according to the above manufacturing method and examples are shown in Tables 2 and 3. Table 2 shows the melting point of compound (I). Table 3 shows the physical properties of compound (I). 1 H-NMR spectral data [using] 1 Determined by H-NMR spectroscopy; δ is the chemical shift value (ppm). It should be noted that the No. in Tables 2 and 3 has the same meaning as in Tables 1-1 and 1-2.

[0329] In Table 2, the melting points are... 1 indicates the temperature at which the compound decomposes when its melting point is determined.

[0330] Table 3 1 In H-NMR spectral data, s represents a singlet, brs represents a broad singlet, d represents a doublet, t represents a triplet, q represents a quartet, and m represents a multiplet.

[0331]

[0332] [Experimental Example]

[0333] Preparation of various pharmaceutical solutions containing the compounds of the present invention: The compound of the present invention was dissolved by mixing it with acetone or dimethyl sulfoxide. Water was added to the solution of the compound of the present invention to dilute it to a predetermined concentration (400 ppm) to obtain a pharmaceutical solution. This pharmaceutical solution was used in the following Test Examples 1 to 3.

[0334] Experiment Example 1: Fungicidal effect test (preventive effect test) against Phytophthora infestans of tomato

[0335] Tomatoes were cultivated in 6cm diameter plastic pots. When the plants reached the 4.5-5.5 leaf stage, 10ml of the pesticide solution was sprayed onto the plants using a spray gun. After the solution dried (on the day of treatment), a spore suspension of *Phytophthora infestans* was sprayed onto the plants and placed in an inoculation chamber at 20°C and 95% humidity for 16 hours. Then, the plants were placed in a constant temperature room at 20°C. The lesion area was assessed 3 days after inoculation, and the control rate was calculated using the following formula. The results showed that each pesticide solution containing the following tested compounds (active ingredient concentration of 400 ppm) exhibited a control rate of over 90% against tomato blight.

[0336] [Formula for calculating control rate]

[0337] Prevention rate (%)=100-(X / Y)×100

[0338] X: Plaque area percentage of the tested compound (%), Y: Plaque area percentage of the untreated area (%)

[0339] 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-55, 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-105, 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-57B-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,

[0340] Experimental Example 2: Treatment of cucumber downy mildew ( Pseudoperonospora cubensis The bactericidal effect test (preventive effect test) of )

[0341] Cucumbers were cultivated in 6cm diameter plastic pots. When the plants reached the 1.2-1.5 leaf stage, 10ml of the pesticide solution was sprayed onto the surface using a spray gun. After the solution dried (on the day of treatment), a spore suspension of *Pseudoperonospora cubensis* was sprayed onto the pots and placed in an inoculation chamber at 20°C and 95% humidity for 24 hours. Then, the pots were placed in a constant temperature room at 20°C. Seven days after inoculation, the lesion area was assessed, and the control rate was calculated using the same formula as in Experiment 1 above. The results showed that each pesticide solution containing the following tested compounds (active ingredient concentration of 400ppm) exhibited a control rate of over 90% against cucumber downy mildew.

[0342] 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

[0343] Test Example 3: Against tomato late blight ( Phytophthora infestans Bactericidal efficacy test (therapeutic efficacy test)

[0344] Tomatoes were cultivated in 6cm diameter plastic pots. When the plants reached the 4.5-5.5 leaf stage, a spore suspension of *Phytophthora infestans* was sprayed into the pots, which were then placed in an inoculation chamber at 20°C and 95% humidity for 4 hours. Then, 10ml of the solution was sprayed through a spray gun. After the solution dried (on the day of treatment), the pots were placed in a constant temperature room at 20°C. The lesion area was assessed 3 days after inoculation, and the control rate was calculated using the same formula as in Experiment 1 above. The results showed that each solution containing the tested compounds (active ingredient concentration of 400ppm) exhibited a control rate of over 90% against tomato blight.

[0345] Test compounds: 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-1 98. 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- 64. 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

[0346] [Comparative Test]

[0347] A comparative experiment was conducted using compound No. A-10 of the present invention and the compound described in manufacturing example 2 of Patent Document 1 (hereinafter referred to as comparative compound 1) as active ingredients.

[0348] Preparation of drug solutions containing each compound: Using the test compounds listed in Table 4 below, each drug solution was prepared by the same preparation method as described above to achieve a specified concentration of active ingredient (400 ppm, 200 ppm, 100 ppm, or 50 ppm). The drug solutions adjusted to the specified concentrations were used in the following comparative test example 1.

[0349] Comparative Experiment Example 1: Treatment of cucumber downy mildew ( Pseudoperonospora cubensis The bactericidal effect test (preventive effect test) of )

[0350] Using the solutions adjusted to the concentrations specified above, a fungicidal effect test on cucumber downy mildew was conducted according to the method described in Test Example 2.

[0351] The results of the concentrations of each active ingredient in each solution containing each test compound are shown in Table 4. A represents 100% control rate, B represents 90-99% control rate, C represents 70-89% control rate, D represents 30-69% control rate, and E represents 0-29% control rate.

[0352]

[0353] According to Table 4, compound No. A-10, which is an N-substituted oxyamide compound of the present invention, showed excellent control of cucumber downy mildew compared with the amide compound of Patent Document 1 (comparative compound 1).

[0354] Therefore, through the examples, it was found that the N-substituted oxoamide compounds of the present invention exhibit excellent control effects against harmful plant diseases. Furthermore, it was found that, compared with the amide compounds of Patent Document 1, the N-substituted oxoamide compounds of the present invention exhibit superior control effects against harmful plant diseases.

[0355] The following describes formulation examples containing compound (I), but the proportions, dosage forms, etc. are not limited to the examples described.

[0356] Formulation Example 1

[0357] (1) Compound (I) 20 parts by weight

[0358] (2) 72 parts by weight of clay

[0359] (3) 8 parts by weight of sodium lignosulfonate

[0360] The above substances are mixed evenly to form a wettable powder.

[0361] Formulation Example 2

[0362] (1) Compound (I) 5 parts by weight

[0363] (2) 95 parts by weight of talc

[0364] The above substances are mixed evenly to form a powder.

[0365] Formulation Example 3

[0366] (1) Compound (I) 20 parts by weight

[0367] (2) 20 parts by weight of N,N-dimethylacetamide

[0368] (3) 10 parts by weight of polyoxyethylene alkyl phenyl ether

[0369] (4) 50 parts by weight of xylene

[0370] The above substances are mixed and dissolved evenly to form an emulsion.

[0371] Formulation Example 4

[0372] (1) 68 parts by weight of clay

[0373] (2) Sodium lignosulfonate 2 parts by weight

[0374] (3) 5 parts by weight of polyoxyethylene alkyl aryl sulfate

[0375] (4) 25 parts by weight of micronized silica

[0376] The mixture of the above components is mixed with compound (I) in a weight ratio of 4:1 to prepare a wettable powder.

[0377] Formulation Example 5

[0378] (1) Compound (I) 50 parts by weight

[0379] (2) 2 parts by weight of polyoxyethylene alkylphenyl ether triethanolamine phosphate salt

[0380] (3) 0.2 parts by weight of organosilicon

[0381] (4) 47.8 parts by weight of water

[0382] (5) 5 parts by weight of sodium polycarboxylate

[0383] (6) 42.8 parts by weight of anhydrous sodium sulfate

[0384] The above (1)~(4) are mixed and pulverized to obtain the stock solution. (5) and (6) are further added to the stock solution and mixed and granulated to produce water-dispersible granules.

[0385] Formulation Example 6

[0386] (1) Compound (I) 5 parts by weight

[0387] (2) 1 part by weight of polyoxyethylene octylphenyl ether

[0388] (3) 0.1 parts by weight of phosphate ester of polyoxyethylene

[0389] (4) 93.9 parts by weight of granular calcium carbonate

[0390] Mix (1) to (3) uniformly beforehand, dilute with an appropriate amount of acetone, spray onto (4), remove the acetone, and make granules.

[0391] Formulation Example 7

[0392] (1) Compound (I) 2.5 parts by weight

[0393] (2) 2.5 parts by weight of N-methyl-2-pyrrolidone

[0394] (3) 95.0 parts by weight of soybean oil

[0395] The above substances are uniformly mixed and dissolved to prepare an ultra-low volume formulation.

[0396] Formulation Example 8

[0397] (1) Compound (I) 20 parts by weight

[0398] (2) 2 parts by weight of polyoxyethylene alkylphenyl ether triethanolamine phosphate salt

[0399] (3) 0.2 parts by weight of organosilicon

[0400] (4) 0.1 parts by weight of xanthan gum

[0401] (5) 5 parts by weight of ethylene glycol

[0402] (6) 72.7 parts by weight of water

[0403] The above substances are uniformly mixed and pulverized to produce an aqueous suspension.

[0404] It should be noted that the entire contents of the description, claims and abstract of Japanese Patent Application Nos. 2023-148047 and 2023-148050, filed on September 13, 2023, are incorporated herein as part of the disclosure of this invention.

Claims

1. The compound represented by formula (I) or a salt thereof, In the formula, R 1 It is a (C1-C5)-chain hydrocarbon or a (C3-C4)-cycloalkyl group, wherein, The (C1-C5)-chain hydrocarbon and the (C3-C4)-cycloalkyl group can be substituted by at least one T. 1 replace, T 1 Halogen, cyano, or -U 1 -R 2 , U 1 It can be O, S, or C(=O)O. R 2 It is (C1-C3)-alkyl. X 1 Halogen, Y 1 Y 2 Y 3 Y 4 and Y 5 Each is independently a halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, cyano, or hydrogen atom, wherein, in R 1 In the case of (C1-C4)-alkyl or (C3-C4)-cycloalkyl, Y 1 Y 2 Y 3 Y 4 and Y 5 Not all of them are hydrogen atoms at the same time.

2. The compound or a salt thereof according to claim 1, R 1 It is (C1-C4)-alkyl, (C3-C4)-cycloalkyl, or (C3-C5)-alkynyl.

3. The compound according to claim 1 or a salt thereof, wherein the compound represented by formula (I) is an N-(cyclo)alkoxyamide compound represented by formula (IA). In the formula, R 1A It is (C1-C4)-alkyl or (C3-C4)-cycloalkyl. X 1 Halogen, Y 1 It can be a halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, cyano, or hydrogen atom. Y 2A Y 3A and Y 4A Each can be independently a hydrogen atom or a halogen. Y 5A For hydrogen atoms, where, In Y 1 In the case of hydrogen atoms, Y 2A Y 3A and Y 4A Not all of them are hydrogen atoms at the same time.

4. The compound according to claim 1 or a salt thereof, wherein the compound represented by formula (I) is an N-alkynyloxyamide compound represented by formula (IB). In the formula, n is 1, 2, or 3. X 1 Halogen, Y 1 Y 2 Y 3 Y 4 and Y 5 Each can be independently a hydrogen atom, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

5. The compound according to claim 1 or a salt thereof, wherein the compound represented by formula (I) is an N-(cyclo)alkoxyamide compound represented by formula (IA) or an N-alkynyloxyamide compound represented by formula (IB). In the formula, R 1A It is (C1-C4)-alkyl or (C3-C4)-cycloalkyl. X 1 Halogen, Y 1 It can be a halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, cyano, or hydrogen atom. Y 2A Y 3A and Y 4A Each can be independently a hydrogen atom or a halogen. Y 5A For hydrogen atoms, where, In Y 1 In the case of hydrogen atoms, Y 2A Y 3A and Y 4A Not all of them are hydrogen atoms at the same time. In the formula, n is 1, 2, or 3. X 1 Halogen, Y 1 Y 2 Y 3 Y 4 and Y 5 Each can be independently a hydrogen atom, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

6. The compound or salt thereof according to any one of claims 1 to 5, Y 1 It can be halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, nitro, or cyano.

7. The compound or a salt thereof according to claim 3 or 5, R 1A It can be methyl, ethyl, or cyclopropyl.

8. The compound or a salt thereof according to any one of claims 1, 2, 4 and 5, Y 5 It is a hydrogen atom.

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

10. A method for preventing and controlling harmful plant diseases, wherein, Apply an effective amount of the compound or its salt according to any one of claims 1 to 5 to a plant, plant pathogen, or soil.

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