N-substituted oxy-2-aminothiazole carboxamide compounds or salts thereof and agricultural and horticultural fungicides

Abstract

Provided is a novel compound that exhibits an excellent control effect against harmful plant diseases. An N-substituted oxy-2-aminothiazolecarboxamide compound represented by the following formula (in the formula, each symbol is as described in the description) or a salt thereof exhibits an excellent control effect against harmful plant diseases.

Description

Technical Field

[0001] This invention relates to novel N-substituted oxy-2-aminothiazole carboxamide compounds or their salts, and fungicides for agricultural and horticultural use containing them as active ingredients. Background Technology

[0002] Patent Document 1 describes N-cycloalkyl-formamide, N-cycloalkyl-thioformamide, and N-cycloalkyl-N-substituted formimide amide derivatives, as well as methods for using these compounds or compositions to control plant pathogenic fungi. However, the N-substituted oxy-2-aminothiazole formamide compound of formula (I) described later is not disclosed at all in this document.

[0003] Existing technical documents

[0004] Patent documents

[0005] Patent Document 1: International Publication No. 2008 / 037789 Summary of the Invention

[0006] The problem that the invention aims to solve

[0007] Existing agricultural and horticultural fungicides suffer from problems such as insufficient practical control of harmful plant diseases depending on the application, the emergence of drug-resistant bacteria, and environmental burdens (impacts on surrounding plants and ecosystems). Therefore, there is a need for new agricultural and horticultural fungicides. The objective of this invention is to provide novel compounds that exhibit excellent control effects against harmful plant diseases.

[0008] Methods for solving problems

[0009] In order to solve the above-mentioned problems, the inventors conducted in-depth research and found that N-substituted oxy-2-aminothiazole carboxamide compounds or their salts of the following formula (I) having a specific pyridin-3-ylmethyl group in their structure have excellent control effects on harmful plant diseases that are a problem in the fields of agriculture and horticulture.

[0010] That is, the present invention is as follows.

[0011] [1] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt (hereinafter also referred to as compound (I)) shown in formula (I).

[0012]

[0013] [In the formula, R] 1 It can be at least 1 T 1 Substituted (C1-C6) chain hydrocarbons, T 1 It is a cyano group or -C(=O)OR2 , R 2 It is a (C1-C3) alkyl group. X 1 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, cyano, or hydrogen atom. Y 1 Y 2 Y 3 and Y 4 Each of these can be independently a halogen, hydrogen atom, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6) haloalkyl, cyano, or nitro group. [2] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is (C1-C6)alkyl or (C2-C6)ynyl.

[0014] [3] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It can be methyl, ethyl, or propargyl.

[0015] [4] According to any one of [1] to [3] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, cyano, or nitro group; however, Y 1 and Y 4 They are not both hydrogen atoms. Y 2 and Y 3 Each is an independent halogen or hydrogen atom.

[0016] [5] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is a (C1-C6) chain hydrocarbon. X 1 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or hydrogen atom. Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6) alkyl, (C1-C6) haloalkyl or nitro group.

[0017] [6] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [5] above, R 1 It is (C1-C6)alkyl or (C2-C6)ynyl.

[0018] [7] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1], [4], and [5] above, R 1 It is methyl or propargyl.

[0019] [8] According to any one of [1] to [3] and [5] to [7] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or nitro group. Y 2 Y 3 and Y 4 Each is an independent halogen or hydrogen atom.

[0020] [9] An agricultural and horticultural fungicide containing, as an active ingredient, any one of the above [1] to [8] N-substituted oxy-2-aminothiazole carboxamide compounds or their salts.

[0021]

[10] A method for controlling harmful plant diseases, wherein an effective amount of any of the above-mentioned [1] to [8] N-substituted oxy-2-aminothiazolium carboxamide compounds or their salts is applied to the plant, plant pathogens or soil.

[0022] The effects of the invention

[0023] 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

[0024] The substituents and chemical structure of compound (I) are described. It should be noted that, in this specification, compounds included in compound (I) are also referred to as compounds of this invention.

[0025] In compound (I), the halogen, or the halogen as a substituent, can be any atom of fluorine, chlorine, bromine, or iodine. The number of halogens as substituents can be one or more; in the case of two or more, each halogen atom can be the same or different. Furthermore, the halogens as substituents can be substituted at any position.

[0026] In compound (I), "C P -C T "C1-C6" refers to carbon atoms ranging from P to T. For example, "C1-C6" means carbon atoms ranging from 1 to 6. In addition, the expression "can be substituted" refers to whether it has substituents or is unsubstituted.

[0027] (C1-C6) chain hydrocarbons refer to (C1-C6) alkyl, (C2-C6) ynyl or (C2-C6) alkenyl.

[0028] (C1-C6) Alkyl groups refer to straight-chain or branched alkyl groups with 1 to 6 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 3-pentyl, n-hexyl, isohexyl, sec-hexyl, 2-methylpentyl, 3-methylpentyl, 3-hexyl, 2-ethylbutyl, 3-methylpentan-2-yl, 4-methylpentan-2-yl, 2,3-dimethylbutyl, tert-hexyl, 2,2-dimethylbutyl, neohexyl, 3-methylpentan-3-yl, 2-methylpentan-3-yl, or 2,3-dimethylbutan-2-yl groups.

[0029] In this specification, (C1-C3) alkyl means a straight-chain or branched alkyl group having 1 to 3 carbon atoms. In specific examples, the alkyl group having 1 to 3 carbon atoms in the above-mentioned (C1-C6) alkyl group is consistent with this.

[0030] (C2-C6) ynyl groups represent straight-chain or branched ynyl groups with 2 to 6 carbon atoms having at least one triple bond at any position. Examples include ethynyl, 1-propynyl, propynyl (also simply 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, 3-butyn-2-yl, 1,3-butadiynyl, 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, 1,3-pentadiynyl, 1,4-pentadiynyl, 2,4-pentadiynyl, 1- Groups such as hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 3,3-dimethyl-1-butynyl, 4-methyl-2-pentynyl, 3-hexyn-2-yl, 4-hexyn-2-yl, 2-methyl-3-pentynyl, 3-methyl-4-pentyn-2-yl, 5-hexyn-2-yl, 2,4-hexadiynyl, 3,5-hexadiynyl, 3,5-hexadiyn-2-yl or 1,3,5-hextriynyl.

[0031] In this specification, (C2-C3) ynyl group refers to a straight-chain ynyl group with 2 to 3 carbon atoms having a triple bond at any position. In the specific example described above, the ynyl group with 2 to 3 carbon atoms is consistent with this.

[0032] (C2-C6) alkenyl groups refer to straight-chain or branched alkenyl groups with 2 to 6 carbon atoms having at least one double bond at any position. Examples include vinyl groups. (Also simply called vinyl), allyl (also simply called 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-buten-2-yl, 3-buten-2-yl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 3-buten-3-yl, 1,3-butadienyl, 1,3-butadien-2-yl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-1-butenyl, 2-methyl-1-butenyl, 2-penten-1-yl, 3-methyl-2-buten-2-yl, 3-methyl-2-butenyl, 2-methyl-2-butenyl, 3-penten-2-yl, 3-methyl-3- Butenyl, 2-methyl-3-butenyl, 1,3-pentadienyl, 2,4-pentadienyl, 2,4-pentadien-2-yl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 2-hexen-2-yl, 2-ethyl-1-butenyl, 4-methyl-3-pentenyl, 3-methyl-3-pentenyl, 2-methyl-3-pentenyl, 2,3-dimethyl-2-butenyl, 4-methyl-3-penten-2-yl, 4-methyl-3-pentenyl, 3-methyl-3-pentenyl, 1,3-hexadienyl, 1,4-hexadienyl, 1,5-hexadienyl, 2,4-hexadienyl, 2,5-hexadienyl or 1,3,5-hextrienyl, etc. Furthermore, in the case of geometric isomers, there are no particular limitations on either the E-body or the Z-body, or a mixture of the E-body and the Z-body in any proportion, as long as it falls within the specified range of carbon atoms.

[0033] The above (C1-C6) chain hydrocarbons can be generated by at least one T 1 Substitution. In the above (C1-C6) chain hydrocarbons, T... 1 In the case of substitution, the above-mentioned (C1-C6) chain hydrocarbons can be replaced by 1 to 13 T... 1 replace.

[0034] In the above (C1-C6) chain hydrocarbons, at least one T 1 In the case of replacement, T 1 The substitution position can be any substitution position on the (C1-C6) chain hydrocarbons mentioned above.

[0035] In the above (C1-C6) chain hydrocarbons, two or more T 1 In the case of replacement, each T 1 They can be the same or different.

[0036] For example, in the R of compound (I) 1 For at least 1 T1 In the case of substituted (C1-C6) alkyl groups, specifically, the following substituents are included. Examples include cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, 4-cyanobutyl, 5-cyanopentyl, 6-cyanohexyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, or isopropoxycarbonylmethyl, etc.

[0037] (C1-C6) Haloalkyl refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms partially or completely substituted by 1 to 13 identical or different halogen atoms. Examples include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 1-fluoro-2-fluoroethyl, 1-fluoro-2-fluoroethyl, 2-fluoropropyl ...2-fluoro -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-Hepenobutyl, Perfluorobutyl, 2,3,3,3,4,4,4-Hepenofluoroisobutyl, 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-Hepenofluoropentyl, 2,2,3,3,4,4,5,5,5-Nonafluoropentyl, Perfluoropentyl, 1-Fluoropentyl Hexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-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-undecanofluorohexyl or perfluorohexyl groups, etc.

[0038] In this specification, (C1-C3) haloalkyl means a straight-chain or branched alkyl group having 1 to 3 carbon atoms that are partially or completely substituted by 1 to 7 identical or different halogen atoms. In the specific examples of (C1-C3) haloalkyl, the haloalkyl group having 1 to 3 carbon atoms in the specific examples of (C1-C6) haloalkyl described above is compliant.

[0039] As a salt of compound (I), it includes all salts as long as they are agriculturally permissible, 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.).

[0040] 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 compound (I) also includes various isomers other than those described above, which are within the scope of common technical knowledge in this field. Furthermore, various isomers can be prepared separately using common technical knowledge and general experimental methods.

[0041] Furthermore, depending on the type of isomer, it may sometimes have a chemical structure different from the recorded structural formula, but anyone skilled in the art can fully recognize that they are isomers and are obviously within the scope of this invention.

[0042] The method for manufacturing compound (I) will now be described.

[0043] 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 (e.g., alkylation, haloalkylation, Suzuki coupling and other cross-coupling reactions, Sandmeier-type reactions, halogenation, oxidation, reduction, etc.) to the substituents on the pyridine ring. 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 can be carried out under an inert gas atmosphere such as nitrogen or argon, and a salt reagent can also be used if necessary.

[0044] [Reaction A]

[0045] Reaction A is a deprotection reaction, a method for obtaining compound (I) by removing the Boc group from the compound of formula (XX-a). Here, the Boc group is a tert-butoxycarbonyl group.

[0046]

[0047] The symbols in the formula are as described above.

[0048] Reaction A can be carried out under known conditions used to remove the Boc group, for example by the method described in Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (John Wiley and Sons, 2007, Peter G.M. Wuts, Theodora W. Greene). More specifically, for example, it can be carried out by reacting with acids such as trifluoroacetic acid or hydrogen chloride in the presence of a solvent, or by reacting with trimethylsilyl trifluoromethanesulfonate in the presence of a solvent and a base such as 2,6-rutidine.

[0049] [Reaction B] and [Reaction C]

[0050] Reaction B is a method for 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 for reacting a compound of formula (II-a) with a compound of formula (III) to obtain a compound of formula (XX-b).

[0051]

[0052] In the formula, R 1a For H or can be at least 1 T 1 Substituted (C1-C6) chain hydrocarbons, where L is a leaving group, can be exemplified by, for example, halogens, alkoxy groups, aryloxy groups, alkyl carbonyloxy groups, aryl carbonyloxy groups, etc. Other symbols are as described above.

[0053] 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), with an expected amount of 0.8 to 1.5 equivalents (equivalents are molar equivalents, as hereinafter the same).

[0054] 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-benzotriazol-1-yloxytripyrrolidinyl Like hexafluorophosphate (PyBOP). It is a condensing agent; 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridine Ureas such as 3-oxide hexafluorophosphate (HATU) Condensing agents; 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 them. Common additives used in conjunction with dehydrating condensing agents such as 1-hydroxybenzotriazole (HOBt) may be added as needed. The amount of the aforementioned dehydrating condensing agent relative to one equivalent of the compound of formula (II) may be 0.5 to 5 equivalents, preferably 1 to 2 equivalents; the amount of the additive relative to one equivalent of the compound of formula (II) may be 0.2 to 5 equivalents, preferably 1 to 2 equivalents.

[0055] The base in reaction B can be selected from, 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-rutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and used in combination. The base can be used in amounts of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound in formula (II).

[0056] The solvent in reaction B can be any substance as long as it is inactive in the reaction. It can be aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; or aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane. Ethers such as alkanes, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water; etc., may be selected appropriately from one or more of these solvents.

[0057] The reaction temperature of reaction B is usually around -20℃ to 150℃, with an expected range of 0℃ to 100℃. The reaction time is usually around 0.5 to 48 hours, with an expected range of 1 to 24 hours.

[0058] 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 0.5 to 3 equivalents relative to the compound of formula (II-a), with an expected amount of 0.8 to 1.5 equivalents.

[0059] The base in reaction C can be selected from, 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-rutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; or a mixture of one or more of the above bases. The base can be used in amounts of 0.1 to 10 equivalents relative to 1 equivalent of the compound of formula (II-a), with a desired amount of 0.5 to 5 equivalents.

[0060] The solvent in reaction C can be any substance as long as it is inactive in the reaction. It can be aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; or aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane. Ethers such as alkanes, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water; etc., may be selected appropriately from one or more of these solvents.

[0061] The reaction temperature of reaction C is usually around -20℃ to 150℃, with an expected range of 0℃ to 100℃. The reaction time is usually around 0.5 to 48 hours, with an expected range of 1 to 24 hours.

[0062] The compound of formula (III) used in reactions B and C can be prepared according to reaction 2-2 or reaction 2-4 below.

[0063] The compound of formula (II) used in reaction B can be manufactured according to reaction 1-1, reaction 1-2 or known methods, or commercially available products can be used.

[0064] The compound of formula (II-a) used in reaction C can be produced by the compound of formula (II) according to reactions 1-4 below or by a known method, or a commercially available product can be used.

[0065] [Reaction D]

[0066] Reaction D is a method for obtaining compound (XX-a) by reacting a compound of formula (XX-c) with a compound of formula (IV).

[0067]

[0068] In the formula, L 1 Examples of leaving groups include halogens, trifluoromethanesulfonyloxy, methanesulfonyloxy, p-toluenesulfonyloxy, and others as described above.

[0069] Reaction D can typically be carried out in the presence of a base and a solvent, with the addition of a phase transfer catalyst as needed. In reaction D, the compound of formula (IV) can be used in amounts of 1 to 5 equivalents relative to the compound of formula (XX-c), with 1 to 3 equivalents being desirable.

[0070] The base in reaction D can be selected from, for example, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; 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-rutidine; organolithium compounds such as n-butyllithium and diisopropylaminolithium; alkali metal carboxylates such as sodium acetate and potassium acetate; and a suitable combination of one or more of the above bases. The base can be used in amounts of 1 to 10 equivalents relative to 1 equivalent of the compound of formula (XX-c), with 1 to 5 equivalents being desirable.

[0071] The solvent in reaction D can be any substance as long as it is inactive in the reaction. It can be aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; or aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane. Ethers such as alkanes, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol, and tert-butanol; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and water; etc., may be selected appropriately from one or more of these solvents.

[0072] Examples of phase transfer catalysts in reaction D include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. The amount of the aforementioned phase transfer catalyst relative to 1 equivalent of the compound of formula (XX-c) can be 0.1 to 3 equivalents.

[0073] The reaction temperature of reaction D is usually around -20℃ to 150℃, with an expected range of 0℃ to 100℃. The reaction time is usually around 10 minutes to 48 hours, with an expected range of 1 to 24 hours.

[0074] The compound of formula (IV) used in reaction D can be manufactured by known methods or commercially available products can be used.

[0075] [Reaction E]

[0076] Reaction E is a method for obtaining a compound of formula (XX-a) by reacting a compound of formula (II-b) with a compound of formula (V).

[0077]

[0078] The symbols in the formula are as described above.

[0079] Reaction E can proceed according to reaction D described above. In reaction E, the compound of formula (V) can be used in amounts of 1 equivalent to the compound of formula (II-b), with 1 to 5 equivalents preferred. In reaction E, the base can be used in amounts of 1 to 10 equivalents to the compound of formula (II-b), with 1 to 5 equivalents preferred. In reaction E, the phase transfer catalyst can be used in amounts of 0.1 to 3 equivalents to the compound of formula (II-b).

[0080] The compound of formula (II-b) used in reaction E can be manufactured according to reactions 1-3 below or a known method, or a commercially available product can be used. The compound of formula (V) used in reaction E can be manufactured according to reactions 2-7, 2-8, 2-9 below or a known method, or a commercially available product can be used.

[0081] 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 1-5 and reactions 2-1 through 2-9) 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.

[0082] Manufacturing methods of each intermediate

[0083] [Reaction 1-1] to [Reaction 1-5]

[0084] Reaction 1-1 is a method for oxidizing the compound of formula (1) to obtain the compound of formula (II). Reaction 1-2 is a method for hydrolyzing the compound of formula (2) to obtain the compound of formula (II).

[0085] Reactions 1-3 are methods for reacting a compound of formula (II) or a compound of formula (II-a) with a compound of formula (3) to obtain a compound of formula (II-b).

[0086] Reactions 1-4 are methods for obtaining compounds of formula (II-a) by halogenation, esterification or carbonylation of compounds of formula (II).

[0087] Reactions 1-5 are methods for protecting the amino group of the compound of formula (VI) with a Boc group to obtain the compound of formula (VII).

[0088]

[0089] In the formulas for each reaction, Z 1 It is an alkyl group, Z 2 It is H or alkyloxy, and other symbols are as described above.

[0090] Reaction 1-1 can be carried out under normal Pinnick oxidation conditions, for example, according to the method described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.

[0091] 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.

[0092] Reactions 1-2 can be carried out under general ester hydrolysis conditions, for example, according to the method described in International Publication No. 2009 / 100171.

[0093] The compound of formula (2) used in reactions 1-2 can be manufactured by known methods, such as International Publication No. 2012 / 006760, Japanese Patent No. 5851663 or the methods described in reactions 1-5, or commercially available products can be used.

[0094] 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 amounts of 0.5 to 10 equivalents relative to the compound of formula (II) or the compound of formula (II-a), with an expected amount of 0.7 to 5 equivalents.

[0095] 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 Patent Publication No. 2006 / 138350 and U.S. Patent Application Publication No. 2014 / 0378399, or commercially available products can be used.

[0096] The compound of formula (II-a) used in reactions 1-3 can be manufactured by known methods or by the methods described in reactions 1-4, or commercially available products can be used.

[0097] Reactions 1-4 are carried out when L in the compound of formula (II-a) is a halogen. Typically, the compound of formula (II) can be reacted with a halogenating agent in the presence of a solvent. N,N-dimethylformamide can be added as needed.

[0098] 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 thionyl chloride. The amount of the halogenating agent used relative to one equivalent of the compound in formula (II) can be 1 to 10 equivalents, with 1 to 3 equivalents being desirable. An excess amount can be used as long as the reaction proceeds without problems.

[0099] In reactions 1-4, when N,N-dimethylformamide is used, the amount of N,N-dimethylformamide used is the amount of catalyst, for example, 0.01 to 0.3 equivalents relative to compound 1 of formula (II).

[0100] 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 typically be esterified by adding a base as needed in the presence of a solvent and a dehydrating condensing agent, thereby reacting the compound with an alcohol or an aryl hydroxyl group.

[0101] 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 alcohols or aryl hydroxyl groups used relative to 1 equivalent of the compound of formula (II) can be 0.5 to 5 equivalents, preferably 0.8 to 1.5 equivalents, and an excess can be used if the reaction proceeds without problems.

[0102] As a dehydrating condensing agent in reactions 1-4, the substances mentioned in reaction B above can be used. When using the aforementioned dehydrating condensing agent in reactions 1-4, a common additive used with the dehydrating condensing agent (e.g., 1-hydroxybenzotriazole (HOBt), etc.) can be added as needed. The amount of the aforementioned dehydrating condensing agent relative to 1 equivalent of compound (II) can be 0.5 to 5 equivalents, preferably 1 to 2 equivalents; the amount of the aforementioned additive relative to 1 equivalent of compound (II) can be 0.2 to 5 equivalents, preferably 1 to 2 equivalents. When using a base with the aforementioned dehydrating condensing agent in reactions 1-4, the base can be a substance mentioned in reaction B above. The amount of the aforementioned base relative to 1 equivalent of compound (II) can be 0.5 to 10 equivalents, preferably 1 to 5 equivalents.

[0103] Furthermore, in reactions 1-4, when the 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 a haloalkane to carry out esterification.

[0104] Examples of haloalkanes used in reactions 1-4 include iodomethane and iodoethane. The haloalkanes mentioned above can be used in amounts of 0.5 to 5 equivalents relative to the compound of formula (II), with an expected amount of 0.8 to 1.5 equivalents.

[0105] As a base that can be used in reactions with haloalkanes in reactions 1-4, the substances mentioned in reaction D above can be used. The base can 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).

[0106] 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 typically be reacted with a carbonylating agent in the presence of a solvent and a base to undergo carbonylation.

[0107] Examples of carbonylating agents used in reactions 1-4 include acetyl chloride, neopentanoyl chloride, benzoyl chloride, acetic anhydride, and benzoic anhydride. The amount of the aforementioned carbonylating agent relative to the amount of compound 1 in formula (II) can be 0.5 to 10 equivalents, preferably 1 to 5 equivalents; an excess can be used if the reaction proceeds without problems. As the base used in reactions 1-4 where carbonylation is involved, the substances mentioned in reaction B above can be used. The amount of the aforementioned base relative to the amount of compound 1 in formula (II) can be 0.5 to 10 equivalents, preferably 1 to 5 equivalents.

[0108] The solvents used in reactions 1-4 can be any substance as long as they are inactive in the reaction. This includes aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; and aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane. Ethers such as alkanes, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water; etc., may be selected appropriately from one or more of these solvents.

[0109] The reaction temperature in reactions 1-4 is usually around -50℃ to 200℃, with an expected range of around -20℃ to 100℃, and the reaction time is usually around 0.1 to 12 hours.

[0110] The compound of formula (II) used in reactions 1-3 and 1-4 can be manufactured according to reaction 1-1, reaction 1-2 or known methods, or commercially available products can be used.

[0111] Reactions 1-5 can be carried out under general reaction conditions with the amino group protected by the Boc group, for example, according to the method described in Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (John Wikey and Sons, 2007, Peter GMWuts, Theodora W. Greene).

[0112] The compound of formula (VI) used in reactions 1-5 can be manufactured by known methods, such as those described in International Publication No. 2018 / 041563 and U.S. Patent Application Publication No. 2008 / 312255, or commercially available products can be used.

[0113] [Reaction 2-1] to [Reaction 2-9]

[0114] Reaction 2-1 is a method for reacting a compound of formula (10) with a compound of formula (3-a) to obtain a compound of formula (11). Reaction 2-2 is a method for reducing a compound of formula (11) to obtain a compound of formula (III). Reaction 2-1 and Reaction 2-2 may also be carried out continuously without separating the compound of formula (11).

[0115] Reactions 2-3 are methods for obtaining the compound of formula (11-b) by reacting the compound of formula (11-a) with the compound of formula (IV).

[0116] Reactions 2-4 are methods for obtaining compounds of formula (III) by reacting a compound of formula (V) with a compound of formula (3-a).

[0117] Reaction 2-5 is a method for obtaining compound (10) from compound (12) using a hydride reducing agent. Reaction 2-6 is a method for reducing compound (10) to obtain compound (13). Reaction 2-7 is a method for obtaining compound (V) from compound (13) using a halogenating agent or a sulfonating agent.

[0118] Reaction 2-8 is a method for obtaining compound (Vb) from compound (Va) using a halogenating agent. Reaction 2-9 is a method for obtaining compound (Vb) from compound (14) using a halogenating agent.

[0119]

[0120] In the formulas for each reaction, L 2 Examples of leaving groups include, for example, trifluoromethanesulfonyloxy, methanesulfonyloxy, p-toluenesulfonyloxy, etc. 3 For halogens, other symbols are as described above.

[0121] 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. The compound of formula (3-a) in reaction 2-1 can be used in amounts of 1 equivalent to the compound of formula (10), ranging from 1 to 5 equivalents, and an excess can be used if the reaction proceeds without problems. The compound of formula (3-a) in reaction 2-1 can be a salt of the compound of formula (3-a) (e.g., hydrochloride, sulfate, or trifluoroacetate).

[0122] The acid in reaction 2-1 can be any of inorganic or organic acids. 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 amount of the acid relative to 1 equivalent of compound in formula (10) can be 0.1 to 10 equivalents. If there are no problems with the reaction, an excess amount can be used.

[0123] 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-rutidine; 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 of formula (3-a).

[0124] Examples of dehydrating agents used in reaction 2-1 include anhydrous magnesium sulfate, anhydrous sodium sulfate, and molecular sieves.

[0125] The solvent in reaction 2-1 can be any substance as long as it is inactive in the reaction. It can be aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; and so on. The solvents may be selected from one or more of the following: ethers such as alkanes, 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; and water.

[0126] The reaction temperature of reaction 2-1 is usually around -20℃ to 200℃, with an expected range of 0℃ to 150℃. The reaction time is usually around 0.5 to 48 hours, with an expected range of 1 to 24 hours.

[0127] The compound of formula (10) used in reaction 2-1 can be manufactured according to reaction 2-5 or a known method, or a commercially available product can be used.

[0128] Reaction 2-2 can usually be carried out in the presence of a reducing agent and a solvent. In addition, an acid can be added as needed.

[0129] Examples of reducing agents in reaction 2-2 include sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and 2-picolino / borane coordination compounds. The reducing agent used can be 0.5 to 10 equivalents, or preferably 1 to 5 equivalents, relative to the amount of compound 1 in formula (11). The added acid can be any of an inorganic acid or an organic acid; examples of inorganic acids include hydrochloric acid, and examples of organic acids include acetic acid and trifluoroacetic acid. The acid used can be 1 to 10 equivalents relative to the amount of compound 1 in formula (11).

[0130] The solvent in reaction 2-2 can be any substance as long as it is inactive in the reaction. It can be aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; or aliphatic hydrocarbons such as carbon tetrachloride, chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane. The appropriate solvents may be selected from one or more of the following: ethers such as alkanes, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; protic polar solvents such as methanol and ethanol; and water.

[0131] The reaction temperature of reaction 2-2 is usually around -20℃ to 150℃, with an expected temperature of around 0℃ to 100℃. The reaction time is usually around 0.5 to 48 hours, with an expected time of around 1 to 24 hours.

[0132] Reactions 2-3 can proceed according to reaction D. The compound of formula (IV) can be used in amounts of 1 to 5 equivalents relative to the compound of formula (11-a), with 1 to 2 equivalents preferred. The base in reaction 2-3 can be used in amounts of 1 to 10 equivalents relative to the compound of formula (11-a), with 1 to 5 equivalents preferred. The phase transfer catalyst in reaction 2-3 can be used in amounts of 0.1 to 3 equivalents relative to the compound of formula (11-a).

[0133] The reaction temperature for reactions 2-3 is usually around -20℃ to 150℃, with an expected range of 0℃ to 100℃. The reaction time is usually around 10 minutes to 48 hours, with an expected range of 1 to 24 hours.

[0134] Reaction 2-4 can proceed according to reaction E. The compound of formula (3-a) in reaction 2-4 can be used in amounts of 1 to 5 equivalents relative to the compound of formula (V), with 1 to 3 equivalents preferred. The compound of formula (3-a) in reaction 2-4 can be a salt of the compound of formula (3-a) (e.g., hydrochloride, sulfate, or trifluoroacetate). The base in reaction 2-4 can be used in amounts of 1 to 10 equivalents relative to the compound of formula (V), with 1 to 5 equivalents preferred. The phase transfer catalyst in reaction 2-4 can be used in amounts of 0.1 to 3 equivalents relative to the compound of formula (V).

[0135] The reaction temperature for reactions 2-4 is typically around -20℃ to 150℃, with an expected range of 0℃ to 100℃. The reaction time is typically around 10 minutes to 48 hours, with an expected range of 1 to 24 hours.

[0136] The compound of formula (V) used in reaction 2-4 can be manufactured by known methods, the methods described in reaction 2-7, reaction 2-8 or reaction 2-9, or commercially available products can be used.

[0137] Reactions 2-5 can be carried out under general conditions for converting cyano groups to formyl groups, for example, according to the method described in Journal of Medicinal Chemistry, 2008, 51, 4021-4029.

[0138] The compound of formula (12) used in reactions 2-5 can be manufactured by known methods or commercially available products can be used.

[0139] Reactions 2-6 can be carried out under general conditions for the reduction of formyl groups, for example, according to the method described in Bioorganic & Medicinal Chemistry Letters, 2012, 22, 901-906.

[0140] Reactions 2-7 can be carried out, for example, under general conditions for halogenating hydroxyl groups or under general conditions for sulfonating hydroxyl groups. Examples of conditions for reactions 2-7 include the methods described in Journal of Medicinal Chemistry, 2003, 46, 453-456, and International Publication No. 2020 / 106307.

[0141] Reactions 2-8 can be carried out under general conditions of halogenation of leaving groups such as methanesulfonyl, for example, according to the method described in Journal of Medicinal Chemistry, 2010, 53, 8421-8439.

[0142] The compound of formula (Va) used in reactions 2-8 can be manufactured according to reactions 2-7 or known methods, or commercially available products can be used.

[0143] Reactions 2-9 can be carried out under general halogenation conditions for pyridylmethylation, for example, according to the method described in Journal of Medicinal Chemistry, 2011, 54, 6106-6116.

[0144] The compound of formula (14) used in reactions 2-9 can be manufactured by known methods or can be commercially available.

[0145] In each of the above reactions, the target compound can be obtained by performing conventional post-treatments (solvent removal by distillation, neutralization, distillation, washing, extraction, filtration, drying, etc.) after the reaction. Furthermore, one or more of these conventional post-treatment methods can be appropriately selected to separate the target compound. Then, the target compound can be purified by conventional methods such as column chromatography and recrystallization, as needed. The intermediates produced by the above reactions can also be used in the crude product state for the next reaction step without separation or purification.

[0146] Compound (I) is useful as an active ingredient in an agricultural and horticultural fungicide that can control harmful plant diseases with low dosage.

[0147] Compound (I) can control plant diseases originating from plant pathogens belonging to the phyla Oomycota, Endomyxa, Olpidiomycota, Ascomycota, Basidiomycota, and Blastodactyta. It is particularly effective against plant diseases originating from plant pathogens belonging to the phyla Oomycota, Endomyxa, and Olpidiomycota.

[0148] The following substances can be cited as examples of plant pathogens belonging to the aforementioned category.

[0149] Plant pathogens belonging to the phylum Oomycota, including various orders such as Albuginales, Anisolpidiales, Lagenidiales, Leptomitales, Myzocytiopsidales, Olpidiopsidales, Peronosporales, Pythiales, Rhipidiales, Saprolegniales, and Sclerosporales.

[0150] Plant pathogens belonging to various classifications such as Endomyxa, Haplosporida, Paradiniida, Paramyxida, Gromiida, Phagomyxida, Plasmodiophorida, and Vampyrellida.

[0151] It belongs to the classification of plant pathogens in the phylum Olpidiomycota and order Olpidiales.

[0152] Plant pathogens belonging to the phylum Ascomycota, including various orders such as Cladosporiales, Diaporthales, Erysiphales, Glomerellales, Helotiales, Hypocreales, Magnaporthales, Mycosphaerellales, Myriangiales, Pleosporales, and Venturiales.

[0153] Plant pathogens belonging to various classifications within the phylum Basidiomycota, including Agaricales, Cantharellales, Pucciniales, and Ustilaginales.

[0154] Examples include substances belonging to the phylum Blastodactycota and the order Physodermatales.

[0155] Specific examples of the aforementioned plant pathogens include the following substances.

[0156] Phytophthora infestans (potato or tomato wilt), Phytophthorapalmivora (fig wilt), Phytophthora cactorum (pear or strawberry wilt), Phytophthora capsici (winter melon, pumpkin, bell pepper or chili pepper wilt), Phytophthora capsici (tomato gray wilt), Phytophthora capsici (eggplant or watermelon brown rot), Phytophthora citricola (citrus brown rot), Phytophthora vignae f. sp. adzukicola (red bean stem wilt), Phytophthora megaspermavar. sojae (edamame stem wilt), Phytophthora porri (onion or shallot white wilt), and Phytophthora porri (cucumber, pumpkin, melon, zucchini downy mildew). *Pseudoperonospora* species, such as *Pseudoperonospora humuli*, *Plasmopara* species, such as *Plasmopara viticola* and *Plasmopara nivea*, *Hyaloperonospora* species, such as *Hyaloperonospora brassicae*, *Bremia* species, such as *Bremia lactucae*, *Pythium graminicola*, *Pythium iwayamai*, *Pythium aphanidermatum*, *Pythium zingiberis*, and *Pythium ultimum var.*Fungi of the genus *Pythium*, such as *Aphanomyces raphani* and *Aphanomyces cochlioides*; fungi of the genus *Albugo*, such as *Albugo macrospora*, *Albugo wasabiae*, and *Albugo ipomoeae-aquaticae*; fungi of the genus *Peronospora manshurica*, *Peronospora parasitica*, *Peronospora destructor*, and *Peronospora farinosa* f. sp., such as *Peronospora manshurica*, *Peronospora parasitica*, *Peronospora destructor*, and *Peronospora farinosa* f. sp., such as *Peronospora farinosa*. Downy mildew fungi (Peronospora genus) such as Spinaciae and Peronospora belbahrii, the causal agent of basil downy mildew.

[0157] Plasmodiophora fungi, such as those causing clubroot of cabbage, kale, cauliflower, broccoli, or clover; Polymyxa fungi, such as those causing beet necrotic yellow vein virus; Spongospora fungi, such as those causing potato scab; and Olpidium fungi, such as those causing lettuce bigvein virus.

[0158] Powdery mildew fungi of the genus *Erysiphe*, such as *Erysiphe graminis*, the causal agent of wheat powdery mildew; fungi of the genus *Setosphaeria*, such as *Setosphaeria turcica*, the causal agent of corn large leaf spot; fungi of the genus *Sphaerotheca*, such as *Sphaerotheca fuliginea*, the causal agent of strawberry powdery mildew; fungi of the genus *Uncinula*, such as *Uncinula necator*, the causal agent of grape powdery mildew; fungi of the genus *Podosphaera*, such as *Podosphaera leucotricha*, the causal agent of apple powdery mildew; fungi of pea brown spot (*Mycosphaerella pinodes*), apple black spot (*Mycosphaerella pomi*), banana black leaf spot (*Mycosphaerella musicola*), persimmon leaf spot (*Mycosphaerella nawae*), and strawberry snake eye disease (*Mycosphaerella*). Fungi of the genus *Mycosphaerella*, such as *Fragariae*; fungi of the genus *Venturia*, such as *Venturia inaequalis* and *Venturia nashicola*; fungi of the genus *Pyrenophora*, such as *Pyrenophora teres* and *Pyrenophora graminea*; fungi of the genus *Sclerotinia*, such as *Sclerotinia clerotiorum*, *Sclerotinia borealis*, *Sclerotinia minor*, and *Sclerotinia trifoliorum*, such as *Sclerotinia*, ...

[0159] Fungi belonging to the genus *Botryotinia*, such as *Botryotinia arachidis*, the causal agent of peanut sclerotium rot; fungi belonging to the genus *Cochliobolus*, such as *Cochliobolus miyabeanus*, the causal agent of rice and sesame leaf blight; fungi belonging to the genus *Didymella*, such as *Didymella bryoniae*, the causal agent of cucumber anthracnose; fungi belonging to the genus *Gibberella*, such as *Gibberella fujikuroi*, the causal agent of rice seedling blight; fungi belonging to the genus *Elsinoe*, such as *Elsinoe ampelina*, the causal agent of grape black rot and citrus scab; fungi belonging to the genus *Diaporthe*, such as *Diaporthe citri*, the causal agent of grape branch swelling; fungi belonging to the genus *Monilinia mali*, the causal agent of apple brown rot; and fungi belonging to the genus *Monilinia*, the causal agent of peach gray spot. Fungi of the genus *Monilinia*, such as *fructicola*; fungi of the genus *Glomerella*, such as *Glomerella cingulata*, the causal agent of grape late rot.

[0160] Fungi of the genus *Rhizoctonia*, such as *Rhizoctonia solani*, the causal agent of rice sheath blight; fungi of the genus *Ustilago*, such as *Ustilago nuda*, the causal agent of wheat loose smut; fungi of the genus *Puccinia*, such as *Puccinia coronata*, *Puccinia recondita*, and *Puccinia striiformis*, the causal agent of wheat crown rust; fungi of the genus *Phakopsora*, such as *Phakopsora pachyrhizi*, the causal agent of soybean rust; and fungi of the genus *Typhula*, such as *Typhula incarnata* or *Typhulaishikariensis*, the causal agent of wheat or barley snow rot.

[0161] Fungi of the genus *Septoria*, such as *Septoria nodorum* and *Septoria tritici*, which cause wheat glume blight; fungi of the genus *Botrytis*, such as *Botrytis cinerea*, *Botrytis allii*, and *Botrytis squamosa*, *Botrytis byssoidea*, or *Botrytis tulipae*, which cause leaf blight in onions; fungi of the genus *Fusarium*, such as *Fusarium graminearum*, *Fusarium oxysporum*, which cause cucumber vine blight; and fungi of the genus *Pyricularia*, which cause rice blast. Fungi of the genus *Pyricularia* such as *Cercospora* (beet brown spot fungus) and *Cercospora kakivora* (persimmon angular leaf spot fungus); fungi of the genus *Colletotrichum* such as *Colletotrichum orbiculare* (cucumber anthracnose) and *Colletotrichum coffeanum* (small coffee anthracnose fungus); fungi of the genus *Alternaria* (apple pathotype), *Alternaria alternata* (Japanese pear pathotype), *Alternaria solani* (potato summer blight or tomato ring spot), *Alternaria brassicae* (cabbage black spot fungus), *Alternaria brassicicola* (cabbage sooty mold fungus), and *Alternaria* (onion or scallion black spot fungus). Fungi of the genus *Alternaria*, such as *Phomalingam*; fungi of the genus *Phoma*, such as *Pseudocercosporella herpotrichoides*; fungi of the genus *Pseudocercosporella*, such as *Pseudocercosporella herpotrichoides*; and fungi of the genus *Pseudocercosporora*, such as *Pseudocercosporella vitis*.Fungi of the genus *Rhynchosporium*, such as *Rhynchosporium secalis*; fungi of the genus *Cladosporium*, such as *Cladosporium carpophilum*; fungi of the genus *Phomopsis*, such as *Phomopsis sp.*, the causal agent of peach stem rot; fungi of the genus *Gloeosporium*, such as *Gloeosporium kaki*, the causal agent of persimmon anthracnose; fungi of the genus *Fulvia*, such as *Fulvia fulva*, the causal agent of tomato leaf mold; fungi of the genus *Corynespora*, such as *Corynespora cassiicola*, the causal agent of cucumber brown spot; and fungi of the genus *Physoderma*, such as *Physoderma maydis*, the causal agent of corn spot.

[0162] Compound (I) can prevent or treat various plant pathogens by controlling the aforementioned pathogens. In particular, Compound (I) is effective against various diseases that are problems in agriculture and horticulture, such as seedling blight caused by *Pythium*, blast disease caused by *Pythium*, seedling blight caused by *Fusarium*, sesame leaf blight caused by *Cyclocarya*, and sheath blight caused by *Rhizoctonia*; powdery mildew caused by *Pythium*, Fusarium head blight or basal rot caused by *Fusarium*, rust caused by *Pythium*, brown snow rot caused by *Pythium*, loose smut caused by *Ustilago*, eye blight caused by *Pseudomonas*, and leaf blight or glume blight caused by *Syndrome*; and diseases caused by *Fusarium*. This includes diseases of corn such as Fusarium head blight, leaf spot caused by *Aureobasidium*, rust caused by *Pseudomonas*, large leaf spot caused by *Cyclocarya*, sesame leaf blight caused by *Cyclocarya*, root rot caused by *Pythium*, and smut caused by *Ustilago*; diseases of gramineous crops such as smut caused by *Ustilago*, leaf burn caused by *Polycystis*, rust caused by *Pseudomonas*, top rot caused by *Fusarium*, sooty mold caused by *Cercospora*, and leaf blight caused by *Pseudomonas*; and diseases of gramineous crops such as powdery mildew caused by *Pyrophyllus*, rust caused by *Laminaria*, and downy mildew caused by *Pyrophyllus*. Downy mildew, blight or stem blight caused by *Phytophthora*, anthracnose caused by *Anthracnose*, sclerotinia rot caused by *Sclerotinia*, gray mold caused by *Acanthus*, root rot or damping-off caused by *Fusarium*; Fusarium wilt, downy mildew caused by *Peronomyces* or *Peronomyces lepidophyllum*, black spot caused by *Alternaria*, root rot caused by *Stemona*, clubroot caused by *Plasmodiophora*, root shrinkage caused by *Hylocereus*, and Pythium rot caused by *Pythium*; Downy mildew caused by *Plasmodiophora*, blight caused by *Phytophthora*. Diseases of Asteraceae crops, including gray mold caused by *Alternaria*, sclerotinia rot caused by *Sclerotinia*, and rust caused by *Russula*; diseases of tomatoes, including ring spot caused by *Alternaria*, leaf mold caused by *Ophiocorium*, blight or gray blight caused by *Phytophthora*, gray mold caused by *Alternaria*, powdery mildew caused by *Pyrrosia*, wilt caused by *Fusarium*, and anthracnose caused by *Pseudocorium*; and diseases of Solanaceae crops, including summer blight caused by *Alternaria*, blight or brown rot caused by *Phytophthora*, sclerotinia rot caused by *Sclerotinia*, and dry rot caused by *Fusarium*.Diseases of cucurbitaceous crops caused by *Anthracnose* fungi, powdery mildew caused by *Monophyllum* fungi, vine blight caused by *Dictyophora* fungi, downy mildew caused by *Pseudomonas* fungi, blight or brown rot caused by *Phytophthora* fungi, brown spot caused by *Cladosporium* fungi, and vine rot caused by *Fusarium* fungi; diseases of Amaryllidaceae (Allium) crops caused by *Allium* fungi, including downy mildew caused by *Peronosporium* fungi, blight caused by *Phytophthora* fungi, gray mold caused by *Colletotrichum* fungi, sclerotinia rot caused by *Sclerotinia* fungi, and rust caused by *Russula* fungi; diseases of Amaryllidaceae (Allium) crops caused by *Peronosporium* fungi, black leaf blight or black spot caused by *Alternaria* fungi, gray mold caused by *Colletotrichum* fungi, sclerotinia rot caused by *Sclerotinia* fungi, and diseases caused by *Powdery mildew* fungi. Diseases of Apiaceae crops such as powdery mildew and leaf spot caused by *Cercospora*; diseases of Liliaceae crops such as leaf blight caused by *Colletotrichum*, blight caused by *Phytophthora*, and stem blight caused by *Pseudomonas*; diseases of Polygonaceae crops such as downy mildew caused by *Peronobacter*, powdery mildew caused by *Erythromyces*, and damping-off caused by *Rhizoctonia*; diseases of Convolvulaceae crops such as white rust caused by *White Rust*, vine blight caused by *Fusarium*, black spot caused by *Cladosporium*, and damping-off caused by *Streptomyces*; root rot caused by *Hylocereus*, white rust caused by *White Rust*, downy mildew caused by *Peronobacter*, blight caused by *Phytophthora*, and gray mold caused by *Colletotrichum*. Diseases of Chenopodiaceae crops, including 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 *Erythromyces*, downy mildew caused by *Peronospora*, gray mold caused by *Cercospora*, brown spot caused by *Pseudocercospora*, and branch swelling caused by *Cercospora*; diseases of strawberries, including powdery mildew caused by *Monophyllum*, gray mold caused by *Cercospora*, anthracnose caused by *Cercospora*, and dry rot caused by *Fusarium*; and brown rot caused by *Sclerotinia*, powdery mildew caused by *Monophyllum*, and other diseases caused by *Cercospora*. Diseases of apples caused by fungi of the genus *Aureobasidium*, anthracnose caused by *Microcystis*, brown spot caused by *Diplostomum*, ring spot caused by *Botrytis*, sooty mold caused by *Vibrio*, sooty mold caused by *Syndrome*, and black spot caused by *Cyclocarya*; diseases of pears caused by fungi of the genus *Aureobasidium*, black spot caused by *Alternaria*, powdery mildew caused by *Syndrome*, blight caused by *Phytophthora*, and fruit rot caused by *Fusarium*; and diseases of peaches caused by fungi of the genus *Cladosporium*, black spot caused by *Cladosporium*, and *Phytophthora* rot.This treatment is effective in controlling diseases of citrus and other Rutaceae crops, including black spot caused by *Melastoma*, scab caused by *Cercospora*, and Fusarium damping-off 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 *Phyllostachys*; diseases of Theaceae crops, including anthracnose caused by *Anthracnose*, ring spot caused by *Polytrichum*, red burn caused by *Pseudomonas*, and cake disease caused by *Exophytum*; diseases of gingeraceae crops, including root and stem rot caused by *Pythium*; and diseases of Lamiaceae crops, including downy mildew caused by *Peronospora*.

[0163] In addition, it is effective against diseases of wheat caused by *Fusarium* species, including Fusarium head blight or basal rot; anthracnose caused by *Amanita* species; smut caused by *Ustilago* species; loose smut caused by *Ustilago* species; leaf streak caused by *Cephalospora* species; and glume blight caused by *Syngonium* species. It is also effective against diseases of gramineous crops such as leaf blight of sesame caused by *Helicobacter* species; anthracnose caused by *Amanita* species; and damping-off of seedlings caused by *Fusarium* species. Furthermore, it is effective against diseases of gramineous crops such as red rot caused by *Helicobacter* species; black rot caused by *Helicobacter* species; and downy mildew caused by *Peronospora* species. Finally, it is effective against diseases of grasses such as purpura caused by *Cercospora* species; downy mildew caused by *Peronospora* species; and diseases caused by *Fusarium* species. Diseases of leguminous crops, including damping-off, brown spot caused by *Syndrome*, black spot caused by *Syndrome*, anthracnose caused by *Anthracnose*, and dormancy disease caused by *Myxocytosporium*; diseases of cabbage, including black spot or sooty mold caused by *Alternaria*, downy mildew caused by *Peronobacter*, bacterial black spot caused by *Pseudomonas*, black rot caused by *Xanthomonas*, and root rot caused by *Pseudomonas*; diseases of radish, including black spot caused by *Alternaria*, yellowing caused by *Fusarium*, and black rot caused by *Xanthomonas*; and diseases of radish, including black spot caused by *Alternaria*, black rot caused by *Xanthomonas*, and yellowing caused by *Verticillium*. Diseases of cruciferous crops such as cabbage; 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 rot caused by *Helicobacter*, and powdery scab caused by *Pseudomonas*; diseases of cucumbers such as black spot caused by *Alternaria*, bacterial spot caused by *Pseudomonas*, and bacterial brown spot caused by *Xanthomonas*; diseases of cucurbitaceous crops such as black spot caused by *Alternaria* and bacterial spot caused by *Apocynum*. This treatment is effective against diseases of the Amaryllidaceae family (Allium genus) such as gray rot or mycelial rot caused by fungi, dry rot caused by Fusarium spp., downy mildew caused by Peronosporium 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 spp., and bacterial spot caused by Xanthomonas spp.; diseases of celery such as leaf blight caused by Phytosporum spp., sclerotium rot caused by Sclerotinia spp., and bacterial leaf blight caused by Pseudomonas spp.; diseases of spinach such as downy mildew caused by Peronosporium spp., wilt caused by Fusarium spp., and anthracnose caused by Anthracnose spp.; and seed-borne infectious diseases.

[0164] Furthermore, it is also effective in preventing and controlling soil diseases caused by plant pathogens such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodium, and Leuconostoc.

[0165] Compound (I) can prevent or cure the aforementioned diseases. Using the test methods described in the examples below, certain compounds (I) of the present invention can exhibit excellent preventive or curative effects at low concentrations (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).

[0166] Furthermore, compound (I) has excellent rain resistance, residual effect, and penetration, so by applying compound (I) to plants, harmful fungi on the above-ground parts of plants can be controlled for a certain period of time.

[0167] To prevent and control various harmful plant diseases, an effective amount of compound (I) can be applied to the plant, plant pathogens, or soil.

[0168] The aforementioned effective amount refers to the amount of compound (I) applied that exerts a preventive and control effect on various harmful plant diseases.

[0169] The term "plant body" as used above 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; as well as seeds, seedlings, and transplanted seedlings.

[0170] The aforementioned soil refers to cultivated land such as dry fields, paddy fields, orchards, and non-agricultural land such as lawns and forests, which are suitable for plant cultivation.

[0171] 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: grass crops (rice, wheat, barley, oats, rye, corn, sugarcane, etc.), legume crops (soybeans, kidney beans, red beans, peas, peanuts, edamame, alfalfa, etc.), cruciferous crops (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, rapeseed, tuberous purslane, 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 crops (scallions, leeks, shallots, garlic, onions, shallots, etc.), umbelliferous crops (celery, carrots, parsley, duckweed, etc.), lilyaceae crops (lilies, etc.). Tulips, asparagus, etc.), Polygonaceae crops (buckwheat, etc.), Convolvulaceae crops (sweet potato, water spinach, etc.), Chenopodiaceae crops (spinach, beet, etc.), Vitaceae crops (grapes, etc.), Rosaceae crops (rose, strawberry, apple, pear, peach, loquat, almond, etc.), Rutaceae crops (mandarin orange, lemon, sweet orange, citrus, etc.), Ebenaceae crops (persimmon, etc.), Moraceae crops (fig, etc.), Theaceae crops (tea, etc.), Oleaceae crops (olive, jasmine, etc.), Malvaceae crops (cotton, cocoa, coffee, okra, etc.), Musaceae crops (banana, etc.), Zingiberaceae crops (ginger, ginger, etc.), Lamiaceae crops (basil, etc.), Rubiaceae crops (small-grain coffee, etc.), Bromeliaceae crops (pineapple, pineapple, etc.), Plumeriaceae crops (starflower, etc.), Caryophyllaceae crops (carnation, etc.), Violaceae crops (pansy, etc.).

[0172] Among the aforementioned plants are those cultivated using gene recombination technology and gene editing technology, such as plants endowed with environmental stress tolerance, herbicide tolerance, pest tolerance, disease tolerance, etc., or plants whose growth, fertility traits, product quality, yield, etc., have been altered.

[0173] Compound (I) is typically formulated into various forms, such as powders, granules, water-dispersible granules, wettable powders, aqueous suspensions, oil suspensions, water-soluble powders, emulsions, liquids, ointments, aerosols, ultra-low volume formulations, and microcapsules, by mixing compound (I) with excipients. However, all formulation forms commonly used in this field can be formulated as long as they are suitable for the purposes of this invention. Examples of excipients used in formulations include solid carriers and liquid carriers, but surfactants and other formulation excipients may also be added as needed.

[0174] 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.

[0175] Specific examples of the aforementioned liquid carriers include water, toluene, xylene, solvent naphtha, and dimethyl methacrylate (DMMA). Alkane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol.

[0176] Specific examples of the aforementioned surfactants 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 phosphate salts, and salts of naphthalene sulfonic acid formaldehyde condensates; and nonionic surfactants and spreading agents such as sorbitol fatty acid esters, glycerol fatty acid esters, fatty acid polyglycerol esters, 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.

[0177] Specific examples of other pharmaceutical excipients include 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, liquid paraffin, and other vegetable and mineral oils; organosilicon; xanthan gum, etc.

[0178] As long as they do not exceed the purpose of this invention, one or more of these adjuvants may be appropriately selected and used. Furthermore, in addition to the aforementioned adjuvants, substances known in the art may be appropriately selected and used, such as extenders, thickeners, sedimentation inhibitors, antifreeze agents, dispersion stabilizers, phytotoxicity reducers, and fungicides—various commonly used adjuvants. The mixing ratio of compound (I) with various adjuvants, by weight, is generally 0.001:99.999 to 95:5, and ideally 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.) may be added as needed.

[0179] The application of compound (I) cannot be generalized depending on factors such as meteorological conditions, formulation form, target crop, application time, application location, type and occurrence of harmful plant diseases, etc. However, generally, an effective amount of compound (I) can be applied through common application methods, such as dispersal, soil treatment, and seed treatment. When applying an effective amount of compound (I) through common application methods, the concentration of the active ingredient can be 0.1 to 10,000 ppm, preferably 1 to 2,000 ppm, and more preferably 1 to 1,000 ppm.

[0180] In general application methods, a composition (hereinafter also referred to as "this composition") containing compound (I) as an active ingredient or a dilution thereof can be applied. Generally, in the case of dispersal treatment, the appropriate application amount is about 10 to 100,000 g of this composition per hectare. In the case of soil treatment, the appropriate application amount is about 0.01 to 1,000 g of this composition per hectare. In the case of seed treatment, the appropriate application amount is about 0.001 to 100 g of this composition per 1 kg of seeds, preferably about 0.01 to 1 g.

[0181] The aforementioned dispersal treatment refers to a method of preventing and controlling plant pathogens by dispersing an effective amount of the composition onto the surface of the plant's trunk, buds, stems, leaves, flowers, spikes, or fruits, or onto plant pathogens. Examples include dispersal through stems and leaves, and dispersal through the trunk.

[0182] The aforementioned soil treatment refers to a method of treating the soil with this composition to protect crops from damage caused by plant pathogens, and to allow an effective amount of compound (I) to permeate and move into the interior of the plant from the roots, etc. Examples include irrigation treatment (irrigating the soil in which the plant is cultivated), soil mixing treatment (mixing the soil in which the plant is cultivated with the composition), planting hole treatment, treatment of the plant roots or between plants (spreading or irrigation), and mixing treatment of soil used in mounds, seedling boxes, seedling trays, paper pots, or seedbeds.

[0183] The aforementioned seed treatment refers to a method of preventing and controlling plant pathogens by directly or near the seeds or bulbs of crops with this composition to protect them from damage. Examples include coating treatment, powder coating treatment, and immersion treatment.

[0184] In addition, examples include seedling treatment (drenching or soaking), soaking treatment of bulbs, tubers, bulbs, roots, etc., and hydroponic treatment such as further mixing with hydroponic culture solution. Treatment can be applied to the whole plant or to parts of it (stems, leaves, buds, flowers, spikes, fruits, trunks, seeds, bulbs, tubers, bulbs, roots, etc.).

[0185] This composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural agents, fertilizers, pesticide damage reducers, etc., and in such cases, it sometimes shows superior effects and efficacy.

[0186] The aforementioned use of this composition in combination or in combination refers to using this composition with other ingredients simultaneously, separately, or at intervals.

[0187] 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, this composition, and mixed fungicide compositions combining one or more active ingredients of other fungicides, can sometimes improve the application range, treatment timing, and control activity in a more desirable direction. It should be noted that this composition, and the active ingredients of other fungicides, can be used by mixing the separately formulated substances during dispersal, or they can be formulated together for use. Such mixed fungicides are also included in this invention.

[0188] The mixing ratio of compound (I) with other fungicide active ingredient compounds cannot be generally specified depending on meteorological conditions, formulation form, target crop, application time, application location, type of harmful plant disease, and occurrence status. However, by weight, it is generally 1:300 to 300:1, with a desired ratio of 1:100 to 100:1. Furthermore, as an appropriate application amount, the total amount of active ingredient compounds per hectare can be 0.1 to 70,000 g, with a desired amount of 1 to 30,000 g. This invention also includes a method for controlling harmful plant diseases through the application of such a mixed fungicide composition.

[0189] In the application of 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 may also be used for further treatment.

[0190] The active ingredient compounds (generic names) of the so-called fungicides in 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 where various structural isomers such as salts, alkyl esters, and optical isomers are present.

[0191] 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; Benzoimide 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; Compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, fenaminstrobin, flufenoxystrobin, triclopyricarb, and mandestrobin are amphiboxin compounds. 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 fungicides 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.

[0192] The active ingredient compounds (generic names) of the aforementioned other agricultural and horticultural agents, including insecticides, nematicides, acaricides, or soil pest control agents, may be appropriately selected from, for example, the following group of compounds. Even if not specifically stated otherwise, these compounds are included where various structural isomers such as salts, alkyl esters, and optical isomers are present.

[0193] Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenylphenylphosphonothioate), (RS)-(O-ethyl O-4-nitrophenylphenylphosphonothioate)), 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, cyano 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 Carbamate compounds such as bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC (3,5-xylyl methylcarbamate), and fenothiocarb; Derivatives of nereistoxins, such as cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan; Organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, and methoxychlor; Organometallic compounds such as fenbutatin oxide and cyhexatin; 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 n), 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, flonicamid, and flumetnicam; Quaternary keto acid compounds such as spirodiclofen, spiromesifen, and spirobudifen; Tetraamine compounds such as spirotetramat and spiropidion; Compounds such as fluacrypyrim, bifemetstrobin, 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; In addition, other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, and amidoflume. t), sulfluramid, hydramethylnon, metaldehyde, sulfoxaflor, fluensulfone, verbutin, dicloromezotiazine, triflumezopyrim, fluhexafon, tioxazafen, afidopyropen, fometoquin, flupyradifurone, fluazaindolizine, acynonapyr, pyrimifen benzpyrimoxan, flupyrimin oxazosulfyl, sulfiflumin, bisulflufen Compounds such as cybenzoxasulfyl, galquin, tiapyrachlor, and bentioflumin.

[0194] In addition, this composition can be used in combination with the following compounds.

[0195] Microbial pesticides such as crystalline protein toxins, insect pathogen virus agents, 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 thuringiensistenebrionis. Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin benzoate, ivermectin, milkemectin, milkemectin 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 such as ledprona and vadescana.

[0196] The desired solutions of the present invention are described below. However, the present invention is not limited to these.

[0197] [1] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt as shown in formula (I).

[0198] [2] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It can be at least 1 T 1 Substituted (C1-C6)alkyl, (C2-C6)ynyl or (C2-C6)alkenyl.

[0199] [3] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R1 It can be at least 1 T 1 Substituted (C1-C6)alkyl or (C2-C6)ynyl.

[0200] [4] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is (C1-C6)alkyl, (C2-C6)ynyl or (C2-C6)alkenyl.

[0201] [5] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is (C1-C6)alkyl or (C2-C6)ynyl.

[0202] [6] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is (C1-C3)alkyl or (C2-C3)ynyl.

[0203] [7] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It can be methyl, ethyl, propargyl, cyanomethyl, methoxycarbonylmethyl, or allyl.

[0204] [8] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It can be methyl, ethyl, propargyl or allyl.

[0205] [9] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It can be methyl, ethyl, or propargyl.

[0206]

[10] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is methyl or propargyl.

[0207]

[11] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It can be methyl or ethyl.

[0208]

[12] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is a methyl group.

[0209]

[13] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is an ethyl group.

[0210]

[14] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 It is propargyl.

[0211]

[15] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 It can be halogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, cyano or nitro.

[0212]

[16] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 It can be halogen, (C1-C3)alkyl, (C2-C3)alkenyl, (C1-C3)haloalkyl, cyano or nitro.

[0213]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 It can be a fluorine atom, chlorine atom, hydrogen atom, methyl, trifluoromethyl, vinyl, cyano or nitro group.

[0214]

[18] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 and Y 4 They are not both hydrogen atoms.

[0215]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 2 and Y 3 Each is independently a halogen, (C1-C6) alkyl, or hydrogen atom.

[0216]

[20] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[14] above, Y 2 and Y 3 Each is independently a halogen, (C1-C3) alkyl, or hydrogen atom.

[0217]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 2 and Y 3 Each atom can be independently composed of a fluorine atom, a chlorine atom, a methyl atom, or a hydrogen atom.

[0218]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y4 It can be a halogen or a hydrogen atom.

[0219]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 4 It consists of chlorine or hydrogen atoms.

[0220]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C3)alkyl, (C2-C3)alkenyl, (C1-C3)haloalkyl, cyano or nitro.

[0221]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6) alkyl, (C1-C6) haloalkyl or nitro group.

[0222]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, a hydrogen atom, a (C1-C3) alkyl group, a (C1-C3) haloalkyl group, or a nitro group.

[0223]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, hydrogen atom, methyl, trifluoromethyl, vinyl, cyano, or nitro group.

[0224]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y 2 Y 3 and Y 4 Each can be independently a fluorine atom, a chlorine atom, a hydrogen atom, a methyl group, a trifluoromethyl group, a vinyl group, a cyano group, or a nitro group.

[0225]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 and Y 4 Each can be independently a hydrogen atom, halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, cyano, or nitro group; however, Y 1 and Y 4 Y is not simultaneously a hydrogen atom. 2 and Y 3 Each is independently a halogen, (C1-C6) alkyl, or hydrogen atom.

[0226]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, cyano, or nitro group; however, Y 1 and Y 4 Y is not simultaneously a hydrogen atom. 2 and Y 3 Each is an independent halogen or hydrogen atom.

[0227]

[31] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 and Y 4 Each can be independently a hydrogen atom, halogen, (C1-C3)alkyl, (C1-C3)haloalkyl, (C2-C3)alkenyl, cyano, or nitro group; however, Y 1 and Y 4 Y is not simultaneously a hydrogen atom. 2 and Y 3 Each is an independent fluorine atom, chlorine atom, methyl atom, or hydrogen atom.

[0228]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 and Y 4 Each can be independently a hydrogen atom, fluorine atom, chlorine atom, methyl, vinyl, trifluoromethyl, cyano, or nitro group; however, Y 1 and Y 4 Y is not simultaneously a hydrogen atom. 2 and Y 3 Each is an independent fluorine atom, chlorine atom, or hydrogen atom.

[0229]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, cyano, or nitro group, Y 2 Y 3 and Y 4 Each is an independent halogen, (C1-C6) alkyl, or hydrogen atom.

[0230]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 4 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, cyano, or nitro group, Y 1 Y 2 and Y 3 Each is independently a halogen, (C1-C6) alkyl, or hydrogen atom.

[0231]

[35] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 Y is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or nitro group. 2 Y 3 and Y 4 Each is an independent halogen or hydrogen atom.

[0232]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 4 Y is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or nitro group. 1 Y 2 and Y 3 Each is an independent halogen or hydrogen atom.

[0233]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y is a halogen, (C1-C3)alkyl, (C1-C3)haloalkyl, or nitro group. 2 Y 3 and Y 4 Each atom can be independently a fluorine atom, a chlorine atom, or a hydrogen atom.

[0234]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 4 It is a halogen, (C1-C3)alkyl, (C1-C3)haloalkyl or nitro group, Y 1 Y 2 and Y 3Each atom can be independently a fluorine atom, a chlorine atom, or a hydrogen atom.

[0235]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y is a fluorine atom, chlorine atom, methyl, trifluoromethyl, cyano, or nitro group. 2 Y 3 and Y 4 Each is an independent fluorine atom, chlorine atom, or hydrogen atom.

[0236]

[40] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[14] above, Y 4 Y is a fluorine atom, chlorine atom, methyl, trifluoromethyl, cyano, or nitro group. 1 Y 2 and Y 3 Each atom can be independently a fluorine atom, a chlorine atom, or a hydrogen atom.

[0237]

[41] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 Y is a fluorine atom, chlorine atom, methyl, trifluoromethyl, or nitro group. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0238]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y is a fluorine atom, a chlorine atom, or a methyl atom. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0239]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y is a fluorine atom, a chlorine atom, or a trifluoromethyl atom. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0240]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 1 Y is a fluorine atom, a chlorine atom, or a nitro group. 2 and Y 3Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0241]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 Y is a fluorine atom, a chlorine atom, or a cyano group. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0242]

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

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 Y is a fluorine or chlorine atom. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0243]

[47] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 Y is methyl 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0244]

[48] ​​The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[14] above, Y 1 It is trifluoromethyl, Y 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0245]

[49] According to any one of [1] to

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 For nitro, Y 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0246]

[50] According to any one of [1] to

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 It is cyano, Y 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 4 It is a hydrogen atom.

[0247]

[51] According to any one of [1] to

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 4 Y is a fluorine or chlorine atom. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 1 It is a hydrogen atom.

[0248]

[52] According to any one of [1] to

[14] above, the N-substituted oxy-2-aminothiazole carboxamide compound or its salt, Y 4 Y is a chlorine atom. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y 1 It is a hydrogen atom.

[0249]

[53] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It can be a halogen, (C1-C3)alkyl, (C1-C3)haloalkyl, cyano, or hydrogen atom.

[0250]

[54] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It can be a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or hydrogen atom.

[0251]

[55] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It can be a halogen, (C1-C3)alkyl, (C1-C3)haloalkyl or hydrogen atom.

[0252]

[56] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is a halogen.

[0253]

[57] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[52] above, X 1 It is a (C1-C3) alkyl group.

[0254]

[58] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is a (C1-C3) haloalkyl.

[0255]

[59] The N-substituted oxy-2-aminothiazole carboxamide compound or its salt according to any one of [1] to

[52] above, X 1 It can be a fluorine atom, a chlorine atom, a methyl group, a difluoromethyl group, a trifluoromethyl group, a cyano group, or a hydrogen atom.

[0256]

[60] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It can be a fluorine atom, a chlorine atom, a difluoromethyl atom, a trifluoromethyl atom, or a hydrogen atom.

[0257]

[61] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It can be a fluorine atom, a chlorine atom, a methyl atom, or a hydrogen atom.

[0258]

[62] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It can be a fluorine atom, a chlorine atom, or a methyl group.

[0259]

[63] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It consists of fluorine or chlorine atoms.

[0260]

[64] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is difluoromethyl or trifluoromethyl.

[0261]

[65] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is a fluorine atom.

[0262]

[66] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is a chlorine atom.

[0263]

[67] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is a methyl group.

[0264]

[68] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of [1] to

[52] above, X 1 It is a hydrogen atom.

[0265]

[69] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in [1] above, R 1 For (C1-C6) chain hydrocarbons, X 1 Y is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or hydrogen atom. 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6) alkyl, (C1-C6) haloalkyl or nitro group.

[0266]

[70] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in

[69] above, R 1 It is (C1-C6)alkyl or (C2-C6)ynyl.

[0267]

[71] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in

[69] above, R 1 It is (C1-C3)alkyl or (C2-C3)ynyl.

[0268]

[72] According to the N-substituted oxy-2-aminothiazole carboxamide compound or its salt described in

[69] above, R 1 It is methyl or propargyl.

[0269]

[73] According to any one of the N-substituted oxy-2-aminothiazole carboxamide compounds or salts thereof described above

[69] to

[72] , Y 1 Y is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or nitro group. 2 Y 3 and Y 4 Each is an independent halogen or hydrogen atom.

[0270]

[74] According to any one of

[69] to

[72] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 Y is a halogen, (C1-C3)alkyl, (C1-C3)haloalkyl, or nitro group. 2 Y 3 and Y 4 Each atom can be independently a fluorine atom, a chlorine atom, or a hydrogen atom.

[0271]

[75] According to any one of

[69] to

[72] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, Y 1 Y is a fluorine atom, chlorine atom, methyl, trifluoromethyl, or nitro group. 2 and Y 3 Each can be independently a fluorine atom or a hydrogen atom, Y4 It is a hydrogen atom.

[0272]

[76] The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of

[69] to

[75] above, X 1 It can be a halogen, (C1-C3)alkyl, (C1-C3)haloalkyl or hydrogen atom.

[0273]

[77] According to any one of

[69] to

[75] above, the N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof, X 1 It can be a fluorine atom, a chlorine atom, a difluoromethyl atom, a trifluoromethyl atom, or a hydrogen atom.

[0274]

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

[77] N-substituted oxy-2-aminothiazole carboxamide compounds or their salts.

[0275]

[79] A method for controlling plant diseases, wherein an effective amount of any of the N-substituted oxy-2-aminothiazole carboxamide compounds or salts thereof described in any one of [1] to

[77] is applied to a plant, a plant pathogen or soil.

[0276] Example 1

[0277] The following describes embodiments of the present invention, but the present invention is not limited thereto. The melting point of the compounds of the present invention, which are physical properties, was determined using a melting point measuring apparatus (Buchi M-565). 1 The H-NMR spectral data were measured in the determination solvent using an FT-NMR apparatus (JEOL JNM-ECX (500MHz) or Bruker AVANCE III HD (300MHz)). 1 (H-NMR spectroscopy). It should be noted that the assay solvent may also contain tetramethylsilane (TMS) as an internal standard.

[0278] In addition, in this instruction manual, room temperature refers to approximately 10–30°C.

[0279] [Synthesis example]

[0280] Synthetic Example 1: Synthesis of 2-amino-4-chloro-N-{2-chloro-5,6-difluoropyridin-3-yl)methyl}-N-methoxythiazol-5-carboxamide (Compound No. 17)

[0281] (1) (2-chloro-5,6-difluoropyridin-3-yl)methanol: In the dichloromethane (60 mL) solution of 2-chloro-3-cyano-5,6-difluoropyridine (2.0 g) described in Example 2, Step 1 of International Publication 2016 / 097862, a hexane solution of hydride diisobutylaluminum (1.03 M, 36.9 mL) was added dropwise under a nitrogen atmosphere at -78 °C, and the resulting mixture was stirred at this temperature for 1.5 hours. Methanol (1.8 mL) and 10% hydrochloric acid aqueous solution (18 mL) were added sequentially, and the mixture was stirred at this temperature for 30 minutes, followed by stirring at room temperature for 10 minutes. The organic layer was separated, and the aqueous layer was neutralized with a saturated sodium bicarbonate aqueous solution and filtered using diatomaceous earth. The filtrate was extracted with ethyl acetate. The organic layer obtained by extraction was washed sequentially with a saturated sodium potassium tartrate aqueous solution, water, and saturated brine. After drying with anhydrous sodium sulfate and filtration, it was concentrated under reduced pressure to obtain a crude product of oily 2-chloro-5,6-difluoronicotinaldehyde (2.03 g).

[0282] The crude product (2.03 g) was dissolved in methanol (100 mL). Sodium borohydride (0.52 g) was added to the resulting solution at 0 °C. The mixture was stirred overnight at room temperature to obtain a reaction solution. The reaction solution was quenched by adding hydrochloric acid aqueous solution. The quenched reaction solution was neutralized with saturated sodium bicarbonate aqueous solution. Methanol was removed by distillation, and ethyl acetate was added to the residue. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction 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 an oily (2-chloro-5,6-difluoropyridin-3-yl)methanol (1.49 g). 1 The H-NMR spectral data are as follows.

[0283] 1 H NMR (CDCl3 / 300MHz): δ (ppm) = 7.85 (t, 1H), 4.76 (d, 2H), 2.07 (t, 1H).

[0284] (2) N-[(2-chloro-5,6-difluoropyridin-3-yl)methyl]-O-methylhydroxylamine: (i) A mixture of (2-chloro-5,6-difluoropyridin-3-yl)methanol (294 mg) and triethylamine (0.46 mL) was added to tetrahydrofuran (15 mL). Methanesulfonyl chloride (0.14 mL) was added to the resulting mixture at 0 °C, and the mixture was stirred at room temperature for 4.5 hours to obtain a reaction solution. The reaction solution was quenched by adding a saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted using ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product of (2-chloro-5,6-difluoropyridin-3-yl)methanesulfonic acid (409 mg) in oil.

[0285] (ii) The crude product (409 mg) obtained in (2)(i) above was dissolved in acetone (15 mL), and lithium bromide (207 mg) was added to the resulting solution at room temperature. The mixture was stirred under reflux for 2.5 hours. After cooling to room temperature, the reaction solution was quenched by adding water. Ethyl acetate was added to the quenched reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain an oily 3-(bromomethyl)-2-chloro-5,6-difluoropyridine (233 mg) as the crude product.

[0286] (iii) A mixture was obtained by mixing the crude product (233 mg) obtained in (2)(ii) above, diisopropylethylamine (0.5 mL), and N,N-dimethylformamide (5 mL). O-methylhydroxylamine hydrochloride (96.31 mg) was added to the resulting mixture at room temperature, and the mixture was stirred at 50 °C for 7.5 hours to obtain a reaction solution. The resulting reaction solution was cooled to room temperature and then quenched by adding water. Ethyl acetate and heptane were added sequentially to the quenched reaction solution, and the aqueous layer was extracted using a mixed solvent of ethyl acetate and heptane. 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-chloro-5,6-difluoropyridin-3-yl)methyl]-O-methylhydroxylamine (102 mg). 1 The H-NMR spectral data are as follows.

[0287] 1H NMR (CDCl3 / 300MHz): δ(ppm)= 7.76 (t, 1H), 5.89 (brs, 1H), 4.11 (d,2H), 3.53 (s, 3H).

[0288] (3) 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic acid: A solution was obtained by mixing 15.86 g of tert-butyl (4-chloro-5-carboxythiazolyl-2-yl)carbamate and 32 mL of 2-methyl-2-butene, synthesized based on Example 27, Step 1 as described on page 108 of International Publication No. 2008 / 063888, with a mixed solvent of tetrahydrofuran (130 mL) and tert-butanol (130 mL). A solution of 14.49 g of sodium dihydrogen phosphate (22 mL) was added to the resulting solution at 0 °C, and the mixture was stirred to obtain a mixture. After 15 minutes, 13.6 g of sodium chlorite (80%) (44 mL) was added to the mixture, and the mixture was stirred overnight at room temperature. The reaction solution was adjusted to acidity by adding hydrochloric acid, and further extraction was performed by adding 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 obtained solid was dissolved in a saturated sodium bicarbonate aqueous solution, and the aqueous layer was washed with ethyl acetate. Hydrochloric acid was added to the ethyl acetate-washed aqueous layer to adjust the pH to acidity. 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 obtain a solid. The obtained solid was washed with a 50% ethyl acetate / heptane solution to obtain a white solid of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic acid (15.57 g). The substance... 1 The H-NMR spectral data are as follows.

[0289] 1 H NMR (DMSO-d6 / 300MHz): δ(ppm)= 12.19 (s, 1H), 1.49 (s, 9H).

[0290] (4) tert-butyl[4-chloro-5-[{(2-chloro-5,6-difluoropyridin-3-yl)methyl}(methoxy)carbamoyl]thiazolyl-2-yl]carbamate: In a solution of 146.97 mg of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxylic acid in tetrahydrofuran (5 mL), 0.05 mL of oxalyl chloride and a catalyst amount of N,N-dimethylformamide were added under ice-cooling and stirred under a nitrogen atmosphere. After 15 minutes, the mixture was heated to room temperature and stirred for another 30 minutes. The reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazol-5-carboxyl chloride (hereinafter also referred to as acyl chloride). The obtained acyl chloride was dissolved in tetrahydrofuran (3 mL), and then a solution of 100 mg of N-[(2-chloro-5,6-difluoropyridin-3-yl)methyl]-O-methylhydroxylamine in tetrahydrofuran (2 mL) and diisopropylethylamine (0.13 mL) were added sequentially at room temperature. The mixture was stirred at 50 °C for 2.5 hours under a nitrogen atmosphere to obtain the reaction solution. The resulting reaction solution was cooled to room temperature and then 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 organic layer obtained by extraction 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 amorphous tert-butyl[4-chloro-5-[{(2-chloro-5,6-difluoropyridin-3-yl)methyl}(methoxy)carbamoyl]thiazolyl-2-yl]carbamate (189 mg). 1 The H-NMR spectral data are as follows.

[0291] 1 H NMR (DMSO-d6 / 300MHz): δ(ppm)= 12.13 (brs, 1H), 8.12 (t, 1H), 5.01(s, 2H), 3.72 (s, 3H), 1.49 (s, 9H).

[0292] (5) 2-Amino-4-chloro-N-{2-chloro-5,6-difluoropyridin-3-yl)methyl}-N-methoxythiazol-5-carboxamide (Compound No. 17): A reaction solution was obtained by adding 0.62 mL of trifluoroacetic acid to a solution of tert-butyl[4-chloro-5-[{(2-chloro-5,6-difluoropyridin-3-yl)methyl}(methoxy)carbamoyl]thiazolyl-2-yl]carbamate (189 mg) in dichloromethane (3 mL) and stirring overnight at 40 °C. After cooling the resulting reaction solution to room temperature, a saturated aqueous solution of sodium bicarbonate was slowly added to adjust the solution to alkalinity. The aqueous layer of the alkaline reaction solution was extracted with ethyl acetate. The organic layer obtained by extraction 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 compound (compound No. 17, 117 mg) in solid form. 1 The H-NMR spectral data are as follows.

[0293] 1 H NMR (DMSO-d6 / 300MHz): δ(ppm)= 8.08-8.02 (m, 3H), 4.94 (s, 2H), 3.69(s, 3H).

[0294] Next, representative examples of compound (I) will be specifically given in Table 1. These compounds can be synthesized based on the manufacturing methods and synthetic examples described above, as well as methods known in the art.

[0295] In Table 1, No. indicates the compound No. of the compound of the present invention. In Table 1, Me: methyl, Et: ethyl, Pr: n-propyl, Hex: n-hexyl, NO2: nitro, -: single bond, =: double bond, ≡: triple bond.

[0296] Furthermore, in the case of a salt of compound (I), the type of salt is indicated in the remarks column of Table 1. For example, in the remarks column of Table 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. 68 is the hydrochloride salt of compound No. 17. Compound No. 69 is the p-toluenesulfonate of compound No. 17. Compound No. 70 is the sodium salt of compound No. 17.

[0297] [Table 1]

[0298] [Table 2]

[0299] [Table 3]

[0300] [Table 4]

[0301] [Table 5]

[0302] [Table 6]

[0303] [Table 7]

[0304] 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 The determination was performed using H-NMR spectroscopy; δ represents the chemical shift value (ppm). It should be noted that the No. in Tables 2 and 3 has the same meaning as in Table 1.

[0305] In the melting points in Table 2, 1 indicates the temperature at which the compound decomposed when its melting point was determined.

[0306] In 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.

[0307] [Table 8]

[0308] [Table 9]

[0309] Next, specific test examples will be used to illustrate the excellent control effect and usefulness of the compounds of the present invention against harmful plant diseases. Furthermore, as a comparative example, various tests were conducted using Example 68 (hereinafter also referred to as Comparative Compound A) as shown below and described in Patent Document 1.

[0310]

[0311] Compare compound A

[0312] [Experimental Example]

[0313] Preparation of the solution containing the test compound: The test compound was dissolved by mixing it with acetone or dimethyl sulfoxide. Water was then added to the solution of the test compound to dilute it to a specified concentration (400 ppm) to obtain a pharmaceutical solution. This pharmaceutical solution was used in the following Test Examples 1 to 3.

[0314] Experimental Example 1: Treatment of Tomato Phytophthora blight ( Phytophthora infestans The bactericidal effect test (preventive effect test) of )

[0315] 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 using a spray gun. After the solution dried (on the same day as treatment), the tomato blight pathogen (…) was… Phytophthora infestans The spore suspension was sprayed for inoculation in an inoculation chamber at 20°C and 95% humidity for 16 hours. Then, the chamber was placed in a constant temperature room at 20°C, and the lesion area was visually assessed 3 days after inoculation. The control rate was calculated using the following formula. The results showed that each solution (active ingredient concentration of 400 ppm) using the following compounds of the present invention as test compounds exhibited a control rate of over 80% against tomato blight.

[0316] [Formula for calculating control rate]

[0317] Prevention rate (%)=100-(X / Y)×100

[0318] X: Lesion area percentage of the tested compound (%), Y: Lesion area percentage of the untreated area (%)

[0319] Test compounds: Compounds No. 1, 2, 3, 7, 8, 10, 11, 13, 17, 19, 32, 34, 41, 43, 47, 51, 53, 54, 55, 57, 58, 61, 71, 75, 84, 85, 86, 87, 90, 93, 94

[0320] On the other hand, the control rate of the solution using the comparative compound A (active ingredient concentration of 400 ppm) was less than 30%.

[0321] Experimental Example 2: Treatment of cucumber downy mildew ( Pseudoperonospora cubensis The bactericidal effect test (preventive effect test) of )

[0322] 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 using a spray gun. After the solution dried (on the same day or the day after treatment), cucumber downy mildew pathogens were introduced into the fungus. Pseudoperonospora cubensis Spray inoculation was performed using a spore suspension of [a specific compound], and the solution was placed in an inoculation chamber at 20°C and 95% humidity for 24 hours. Then, the chamber was placed in a constant temperature room at 20°C, and 7 days after inoculation, the lesion area percentage was investigated using the same criteria as in Experiment 1 above. The control rate was calculated using the same formula as in Experiment 1 above. The results showed that each solution (active ingredient concentration of 400 ppm) using the following compounds of the present invention as test compounds exhibited a control rate of over 80% against cucumber downy mildew.

[0323] Test compounds: Compounds No. 1, 7, 8, 10, 11, 13, 19, 34, 41, 51, 53, 54, 55, 57, 58, 61, 75, 84, 85, 86, 87, 90, 93, 94

[0324] On the other hand, the control rate of the solution using the comparative compound A (active ingredient concentration of 400 ppm) was less than 30%.

[0325] Experimental Example 3: Treatment of Tomato Phytophthora blight ( Phytophthora infestans Bactericidal efficacy test (therapeutic efficacy test)

[0326] Tomatoes are cultivated in 6cm diameter plastic pots. When they reach the 4.5-5.5 leaf stage, they are infected with tomato blight pathogens (…). Phytophthora infestans The spore suspension was sprayed for inoculation in an inoculation chamber at 20°C and 95% humidity for 4 hours. Then, 10 ml of the solution was dispersed using a spray gun. After the solution dried (on the day of treatment), it was placed in a constant temperature chamber at 20°C. Three days after inoculation, the lesion area was investigated using the same criteria as in Experiment 1 above, and the control rate was calculated using the same formula as in Experiment 1 above. The results showed that each solution (active ingredient concentration of 400 ppm) using the following compounds of the present invention as test compounds exhibited a control rate of over 80% against tomato blight.

[0327] Test compounds: Compounds No. 3, 7, 8, 10, 11, 13, 17, 19, 32, 34, 41, 51, 54, 55, 57, 58, 61, 84, 87

[0328] On the other hand, the control rate of the solution using the comparative compound A (active ingredient concentration of 400 ppm) was less than 30%.

[0329] The above-described experimental examples demonstrate that the compounds of this invention exhibit excellent control effects against harmful plant diseases. Therefore, the compounds of this invention are useful as fungicides for agricultural and horticultural applications.

[0330] Next, examples of formulations containing compound (I) will be described, but the mixing ratio, dosage form, etc. are not limited to the examples described.

[0331] Formulation Example 1

[0332] (1) Compound (I) 20 parts by weight

[0333] (2) 72 parts by weight of clay

[0334] (3) 8 parts by weight of sodium lignosulfonate

[0335] The above substances are mixed evenly to form a wettable powder.

[0336] Formulation Example 2

[0337] (1) Compound (I) 5 parts by weight

[0338] (2) 95 parts by weight of talc

[0339] The above substances are mixed evenly to form a powder.

[0340] Formulation Example 3

[0341] (1) Compound (I) 20 parts by weight

[0342] (2) 20 parts by weight of N,N-dimethylacetamide

[0343] (3) 10 parts by weight of polyoxyethylene alkyl phenyl ether

[0344] (4) 50 parts by weight of xylene

[0345] The above substances are mixed evenly and dissolved to make an emulsion.

[0346] Formulation Example 4

[0347] (1) 68 parts by weight of clay

[0348] (2) Sodium lignosulfonate 2 parts by weight

[0349] (3) 5 parts by weight of polyoxyethylene alkyl aryl sulfate

[0350] (4) 25 parts by weight of micronized silica

[0351] The mixture of the above components is mixed with compound (I) in a weight ratio of 4:1 to prepare a wettable powder.

[0352] Formulation Example 5

[0353] (1) Compound (I) 50 parts by weight

[0354] (2) 2 parts by weight of polyoxyethylene alkylphenyl ether triethanolamine phosphate salt

[0355] (3) 0.2 parts by weight of organosilicon

[0356] (4) 47.8 parts by weight of water

[0357] The above substances are mixed evenly, and the following compounds are further added to the pulverized stock solution. The mixture is then mixed evenly, granulated, and dried to produce water-dispersible granules.

[0358] (5) Sodium polycarboxylate 5 parts by weight

[0359] (6) 42.8 parts by weight of anhydrous sodium sulfate

[0360] Formulation Example 6

[0361] (1) Compound (I) 5 parts by weight

[0362] (2) 1 part by weight of polyoxyethylene octylphenyl ether

[0363] (3) 0.1 parts by weight of phosphate ester of polyoxyethylene

[0364] (4) Granular calcium carbonate 93.9 parts by weight

[0365] Mix (1) to (3) uniformly beforehand, dilute with an appropriate amount of acetone, spray onto (4), remove the acetone, and make granules.

[0366] Formulation Example 7

[0367] (1) Compound (I) 2.5 parts by weight

[0368] (2) 2.5 parts by weight of N-methyl-2-pyrrolidone

[0369] (3) 95.0 parts by weight of soybean oil

[0370] The above substances are mixed and dissolved to produce an ultra-low volume formulation.

[0371] Formulation Example 8

[0372] (1) Compound (I) 20 parts by weight

[0373] (2) 2 parts by weight of polyoxyethylene alkylphenyl ether triethanolamine phosphate salt

[0374] (3) 0.2 parts by weight of organosilicon

[0375] (4) 0.1 parts by weight of xanthan gum

[0376] (5) 5 parts by weight of ethylene glycol

[0377] (6) 72.7 parts by weight of water

[0378] The above substances are mixed evenly and then pulverized to produce an aqueous suspension.

[0379] It should be noted that the entire contents of the specification, claims and abstract of Japanese Patent Application No. 2023-212115, filed on December 15, 2023, are incorporated herein by reference and are adopted as a disclosure of the specification of this invention.

Claims

1. The N-substituted oxy-2-aminothiazole carboxamide compound of formula (I) or a salt thereof, In the formula, R 1 It can be at least 1 T 1 Substituted (C1-C6) chain hydrocarbons, T 1 It is a cyano group or -C(=O)OR 2 , R 2 It is a (C1-C3) alkyl group. X 1 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, cyano, or hydrogen atom. Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, cyano or nitro.

2. The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to claim 1, R 1 It is (C1-C6)alkyl or (C2-C6)ynyl.

3. The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to claim 1, R 1 It can be methyl, ethyl, or propyne.

4. The N-substituted oxy-2-aminothiazolyl carboxamide compound or a salt thereof according to any one of claims 1 to 3, Y 1 and Y 4 Each can be independently a halogen, hydrogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, cyano, or nitro group; however, Y 1 and Y 4 They are not both hydrogen atoms. Y 2 and Y 3 Each is an independent halogen or hydrogen atom.

5. The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to claim 1, R 1 It is a (C1-C6) chain hydrocarbon. X 1 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or hydrogen atom. Y 1 Y 2 Y 3 and Y 4 Each can be independently a halogen, a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) haloalkyl group, or a nitro group.

6. The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to claim 5, R 1 It is (C1-C6)alkyl or (C2-C6)ynyl.

7. The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to claim 5, R 1 It is methyl or propargyl.

8. The N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof according to any one of claims 1 to 3 and 5, Y 1 It is a halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, or nitro group. Y 2 Y 3 and Y 4 Each is an independent halogen or hydrogen atom.

9. An agricultural and horticultural fungicide, comprising, as an active ingredient, any one of claims 1 to 3 and 5 to 7, an N-substituted oxy-2-aminothiazole carboxamide compound or a salt thereof.

10. A method for preventing and controlling harmful plant diseases, wherein, Apply an effective amount of the N-substituted oxy-2-aminothiazole carboxamide compound or its salt as described in any one of claims 1 to 3 and 5 to 7 to plants, plant pathogens or soil.

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