Bactericidal composition including thiazole carboxylic acid hydrazide compound

Abstract

To provide a bactericidal composition with an excellent control effect on plant diseases.SOLUTION: A bactericidal composition contains a thiazole carboxylic acid hydrazide compound represented by formula (I) [where each symbol is as set forth in the specifications] or a salt thereof as an active ingredient. The bactericidal composition has an excellent control effect on plant diseases.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a novel thiazolecarboxylic acid hydrazide compound or a salt thereof, and a fungicidal composition containing them as an active ingredient. [Background technology]

[0002] Patent Document 1 describes a substituted heteroaryl carbonyl hydrazide compound that further enhances resistance to abiotic stress (e.g., cold, heat, drought, salt, flood), promotes plant growth, and / or contributes to an increase in plant production. As a compound in which the substituted heteroaryl is thiazole, compounds of general formulae (Ia19) to (Ia23) and (Io20) in which the 2-position of the thiazole is H, a pyridyl group, or a chloro group are described, and specific examples thereof include compounds D1-1 to D1-681, D2-1 to D2-681, D3-1 to D3-681, D4-1 to D4-681, D5-1 to D5-681, and D6-1 to D6-681.

[0003] However, Patent Document 1 does not describe the thiazole carboxylic acid hydrazide compound of the following formula (I), i.e., 2-amino-4-halogeno-5-thiazole carboxylic acid hydrazide compound, with specific examples. Naturally, Patent Document 1 does not describe the compound of formula (IA), i.e., 2-amino-4-halogeno-5-thiazole carboxylic acid hydrazide compound in which the terminal nitrogen atom of the hydrazide is mono-substituted with methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl, with specific examples. Furthermore, Patent Document 1 does not describe at all the specific effects of the substituted heteroaryl carbonyl hydrazide compound on plant diseases.

[0004] Patent Document 2 describes a 2-halogeno-5-thiazolecarboxylic acid hydrazide compound as a plant disease control agent, but does not describe a 2-amino-4-halogeno-5-thiazolecarboxylic acid hydrazide compound represented by the following formula (I). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2017 / 012965 [Patent Document 2] Japanese Patent Application Publication No. Hei 9-31069 Summary of the Invention [Problem to be solved by the invention]

[0006] The present inventors have found that the substituted heteroarylcarbonyl hydrazide compounds described in Patent Document 1 have low environmental impact, but cannot exert sufficient control effects against plant diseases even at high doses. In addition, there are concerns about problems with existing agricultural and horticultural fungicides, such as practically insufficient control effects against plant diseases depending on the application scene, emergence of drug-resistant bacteria, and environmental impact (impact on surrounding plants and ecosystems). Therefore, the object of the present invention is to provide a novel fungicide composition that exerts excellent control effects against plant diseases regardless of the application scene. [Means for solving the problem]

[0007] As a result of intensive research aimed at solving the above problems, the present inventors have found that a composition containing a compound of the following formula (I) or a salt thereof having a 2-amino-4-halogeno-5-thiazolecarboxylic acid hydrazide structure as an active ingredient exhibits excellent control effects against harmful plant diseases. They have also found that a compound of the following formula (IA) or a salt thereof has particularly excellent control effects against various plant diseases, and have completed the present invention.

[0008] The present inventors have also discovered that a thiazolecarboxylic acid hydrazide compound or a salt thereof having the following specific chemical structure: -Contains compounds that have preventive and pest-control effects against plant diseases; -Contains compounds that have a therapeutic control effect against plant diseases; -Contains compounds that have both preventive and curative effects against plant diseases; - There is little impact on the appearance of the plants to which it is applied; found. That is, the present invention relates to a compound represented by formula (I):

[0009] [ka] [In the formula, R 1 is a halogen, R 2 is H or (C 1 -C 3 )-alkyl, R 3 (C 1 -C 3 )-alkyl, (C 3 -C 4 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl, or H; R 2 and R 3 Together, R 2 and R 3 may form a 3- to 5-membered ring together with the nitrogen atom bonded to Z is cyano, halogen, (C 1 -C 3 )-alkoxy, (C 3 )-cycloalkyl, or (C 1 -C 3 )-alkylthio; R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-Haloalkyl, nitro, cyano, (C 1 -C 3 )-alkylthio, (C1 -C 3 )-haloalkylthio, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 3 -C 4 )-cycloalkyl, or (C 1 -C 3 )-alkoxy, and n is an integer of 1 to 5] or a salt thereof (hereinafter also referred to as compound (I)), as an active ingredient. The present invention relates to a fungicidal composition (hereinafter also referred to as the present composition), and a method for controlling harmful plant diseases, which comprises a step of applying an effective amount of compound (I) to a plant body, a plant pathogen, or soil. The present invention also relates to a compound group of the formula (IA): which has not been specifically known in the past and has particularly excellent control effects against various plant diseases:

[0010] [ka] [In the formula, R 1A is a fluorine, chlorine, or bromine atom, R 3A is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl; R 4A is halogen, (C 1 -C 2 )-alkyl, (C 1 )-Haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio, and n is an integer of 1 to 5] or a salt thereof (hereinafter also referred to as compound (IA)). Effect of the Invention

[0011] The composition of the present invention exhibits superior control effects against plant diseases as compared with similar conventional compounds, and is useful as a fungicidal composition such as an agricultural and horticultural fungicide. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] In the compounds (I) and (IA), R which is a substituent of phenyl 4 or R 4A The number of substitutions may be one or more. When the number of substitutions is two or more, R 4 or R 4A may be the same or different. In compound (I) and compound (IA), the halogen or the halogen as a substituent may be fluorine, chlorine, bromine, or iodine. The number of halogen as a substituent may be one or more than one, and when there are two or more, each halogen atom may be the same or different. In addition, the substitution position of the halogen as a substituent may be any position.

[0013] In the compound (I) and the compound (IA), "C P -C T " means that the number of carbon atoms is P to T. For example, "C 1 -C 3 " means that the number of carbon atoms is 1 to 3.

[0014] (C 1 -C 3 (C)-Alkyl includes, for example, a straight or branched alkyl group having 1 to 3 carbon atoms, such as methyl, ethyl, propyl, or isopropyl. 1 -C 2 )-Alkyl includes, for example, a straight-chain alkyl group having 1 to 2 carbon atoms such as methyl or ethyl. (C 3 -C 4 Examples of the alkynyl include linear or branched alkynyl groups having 3 to 4 carbon atoms and at least one triple bond at any position, such as 1-propynyl, propargyl (also simply referred to as 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl. (C 2 -C 4Examples of the )-alkenyl include straight-chain or branched-chain alkenyl groups having 2 to 4 carbon atoms and at least one double bond at any position, such as vinyl (also simply referred to as ethenyl), allyl (also simply referred to as 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1,3-butadien-2-yl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, and 2-ethyl-2-vinyl. (C 2 -C 3 Examples of the )-alkenyl include linear or branched alkenyl groups having 2 to 3 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, etc. When geometric isomers exist, they are either E or Z isomers, or a mixture of E and Z isomers in any ratio, and are not particularly limited as long as the number of carbon atoms is within the specified range. (C 3 -C 4 (C)-Cycloalkyl includes, for example, cycloalkyl groups having 3 to 4 carbon atoms, such as cyclopropyl and cyclobutyl. 3 )-Cycloalkyl includes, for example, cycloalkyl groups having 3 carbon atoms, such as cyclopropyl.

[0015] (C 1 -C 3)-Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 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, Examples of the alkyl groups include linear or branched alkyl groups having 1 to 3 carbon atoms partially or completely substituted with 1 to 7 identical or different halogen atoms, such as perfluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 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, and 1,1,1,3,3,3-hexafluoroisopropyl. (C 1 )-Haloalkyl includes, for example, an alkyl group having 1 carbon atom which is partially or completely substituted with 1 to 3 identical or different halogen atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, or chlorofluoromethyl. (C 2 -C 4)-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2-dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3-chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoro-1-propenyl, 3-chloro-3,3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 2-fluoro-1-methylvinyl, 2,2-difluoro-1-methylvinyl, 2-chloro-1-methylvinyl, 2,2-dichloro-1-methylvinyl, Examples of the alkenyl group include 2-bromo-1-methylvinyl, 2,2-dibromo-1-methylvinyl, 4,4,4-trifluoro-1-butenyl, 4,4,4-trifluoro-2-butenyl, 4,4-difluoro-3-butenyl, 3,3-difluoro-1-methyl-2-propenyl, 2-fluoro-1-ethylvinyl, 2,2-difluoro-1-ethylvinyl, 2-chloro-1-ethylvinyl, 2,2-dichloro-1-ethylvinyl, 2-bromo-1-ethylvinyl, 2,2-dibromo-1-ethylvinyl, 2-fluoro-1-methyl-1-propenyl, 2-chloro-1-methyl-1-propenyl, and 2-bromo-1-methyl-1-propenyl, which have at least one double bond at any position and are substituted with one or more identical or different halogen atoms. (C 2 -C 3)-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2-dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3-chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoroallyl. Examples of the alkenyl group include linear or branched alkenyl groups having 2 to 3 carbon atoms and substituted with one or more identical or different halogen atoms, having at least one double bond at any position, such as 2-1-propenyl, 3-chloro-3,3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 2-fluoro-1-methylvinyl, 2,2-difluoro-1-methylvinyl, 2-chloro-1-methylvinyl, 2,2-dichloro-1-methylvinyl, 2-bromo-1-methylvinyl, or 2,2-dibromo-1-methylvinyl. In addition, when there is a geometric isomer, it is either E or Z isomer, or a mixture of E and Z isomers in any ratio, and is not particularly limited as long as it is within the range of the specified carbon number.

[0016] At least one Z is substituted (C 1 -C 3)-Alkyl is, for example, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, dicyanomethyl, 2,2-dicyanoethyl, methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl. , 1-isopropoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 1-methoxy-2-propyl, 1-ethoxy-2-propyl, 1-propoxy-2-propyl, 1-isopropoxy-2-propyl, 2-methoxy-2-propyl, 2-ethoxy-2-propyl, 2-propoxy-2-propyl, 2-isopropoxy-2-propyl, dimethoxymethyl, diethoxy Dimethyl, 2,2-dimethoxyethyl, 2,2-diethoxyethyl, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 1-methylthioethyl, 1-ethylthioethyl, 1-propylthioethyl, 1-isopropylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 1-methylthiopropyl, 1-ethylthiopropyl, 1-propylthiopropyl, 1-isopropylthiopropyl, 2-methylthiopropyl, 2-ethylthiopropyl, 2-Propylthiopropyl, 2-isopropylthiopropyl, 3-methylthiopropyl, 3-ethylthiopropyl, 3-propylthiopropyl, 3-isopropylthiopropyl, 1-methylthio-2-propyl, 1-ethylthio-2-propyl, 1-propylthio-2-propyl, 1-isopropylthio-2-propyl, 2-methylthio-2-propyl, 2-ethylthio-2-propyl, 2-propylthio-2-propyl, 2-isopropylthio-2-propyl, dimethylthiomethyl, diethylthiomethyl, 2,2-dimethylthioethyl, 2,2-Diethylthioethyl, cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylpropyl, 2-cyclopropylpropyl, 3-cyclopropylpropyl, 2-cyclopropyl-2-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 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 Examples of the alkyl group include linear or branched alkyl groups having 1 to 3 carbon atoms substituted with at least one Z at any position, such as 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl, 2,2,3,3,3-pentafluoropropyl, or 1,1,1,3,3,3-hexafluoroisopropyl. The number of Z substitutions may be one or more, and when there are two or more, the types of Z may be the same or different, and it is preferable that the types of Z are the same. In addition, the substitution position of Z may be any position.

[0017] (C 1 -C 3 )-Alkoxy includes, for example, straight or branched alkoxy groups having 1 to 3 carbon atoms, such as methoxy, ethoxy, propoxy, or isopropoxy.

[0018] (C 1 -C 3 (C)-Alkylthio includes, for example, linear or branched alkylthio groups having 1 to 3 carbon atoms, such as methylthio, ethylthio, propylthio, and isopropylthio. 1)-Alkylthio is, for example, a straight-chain alkylthio group having one carbon atom, such as methylthio. (C 1 -C 3 Examples of the haloalkylthio include linear or branched alkylthio groups having 1 to 3 carbon atoms substituted with 1 to 7 identical or different halogen atoms, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloroethylthio, 2,2-dichloroethylthio, 2,2,2-trichloroethylthio, perfluoroethylthio, perfluoropropylthio, perfluoroisopropylthio, 3,3,3-trifluoropropylthio, 2,2,3,3,3-pentafluoropropylthio, 1,1,1,3,3,3-hexafluoroisopropylthio, and 2-fluoro-2-propylthio. (C 1 )-Haloalkylthio includes, for example, a linear alkylthio group having 1 carbon atom substituted with 1 to 3 of the same or different halogen atoms, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, and dichlorofluoromethylthio.

[0019] R 2 and R 3 Together, R 2 and R 3 and the nitrogen atom bonded to the ring may form a 3- to 5-membered ring, which may be saturated or unsaturated. For example, the saturated ring may be aziridine, azetidine, or pyrrolidine, and the unsaturated ring may be pyrrole or dihydropyrrole.

[0020] The salt of compound (I) or compound (IA) includes any salt that is agriculturally acceptable, such as alkali metal salts (e.g., sodium salt, potassium salt, etc.), alkaline earth metal salts (e.g., magnesium salt, calcium salt, etc.), inorganic acid salts (e.g., hydrochloride, perchlorate, sulfate, nitrate, etc.) or organic acid salts (e.g., acetate, methanesulfonate, paratoluenesulfonate, oxalate, etc.).

[0021] Compound (I) has various isomers, such as optical isomers and geometric isomers, and the present invention may include both each isomer and a mixture of isomers. Compound (I) also includes various isomers other than those described above within the scope of common technical knowledge in the relevant technical field. Furthermore, various isomers can be produced separately using common technical knowledge in the relevant technical field and general experimental techniques.

[0022] In addition, depending on the type of isomer, the chemical structure may differ from the structural formula shown, but since a person skilled in the art would be able to fully recognize that these are isomers, it is clear that these are within the scope of the present invention.

[0023] Next, a method for producing compound (I) will be described. Compound (I) includes compound (IA), and therefore the following description also includes a method for producing compound (IA). Compound (I) can be produced according to the following production method 1 (reaction A to reaction K) and a conventional method for producing a salt, but the method for obtaining the compound is not limited to these methods. For example, compound (I) of the present invention can also be produced by applying various substituent conversion reactions well known in this field to the substituent on the phenyl (e.g., alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction, Sandmeyer type reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.). In addition, protection and deprotection reactions commonly used in this field may be applied in the production of the compound of the present invention, if necessary. When carrying out the reaction, it may be carried out under an inert gas atmosphere such as nitrogen or argon, if necessary, and a salt reagent may be used.

[0024] Manufacturing method 1 [Reaction A] Reaction A is a method of obtaining a compound of formula (I) by deprotecting the Boc group from a compound of formula (XX-a). The Boc group is a tert-butoxycarbonyl group.

[0025] [ka]

[0026] The symbols in the formula are as defined above.

[0027] Reaction A can be carried out under known conditions used for deprotection of a Boc group, for example, the method described in Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (John Wikey and Sons, 2007, Peter GMWuts, Theodora W. Greene). More specifically, for example, reaction can be carried out by reacting with an acid such as trifluoroacetic acid or hydrogen chloride in the presence of a solvent, or by reacting with trimethylsilyl triflate in the presence of a solvent and a base such as 2,6-lutidine.

[0028] [Reaction B] and [Reaction C] Reaction B is a method of reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (XX-b). Reaction C is a method of reacting a compound of formula (II-a) with a compound of formula (III) to obtain a compound of formula (XX-b).

[0029] [ka]

[0030] In the formula, A is NH 2 or NH(Boc), R 2a is H, (C 1 -C 3 )-alkyl or Boc, R 2a But (C 1 -C 3 )-alkyl, R 2a and R 3 Together, R 2a and R 3 may form a 3- to 5-membered ring (e.g., aziridine, azetidine, pyrrolidine, dihydropyrrole, or pyrrole) together with the nitrogen atom bonded to L. L is a leaving group, e.g., halogen, alkoxy, aryloxy, alkylcarbonyloxy, arylcarbonyloxy, etc. The other symbols are as described above.

[0031] Reaction B can be carried out usually in the presence of a dehydration condensation agent and a solvent, optionally with the addition of a base. The compound of formula (III) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II) (the equivalent is a molar equivalent, and the same applies below).

[0032] Examples of the dehydration condensation agent include carbodiimide-based condensation agents such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC) or its hydrochloride; imidazole-based condensation agents such as 1,1'-carbonyldiimidazole (CDI); triazine-based condensation agents such as 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM); phosphonium-based condensation agents such as 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP); and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium. Examples of the condensing agent include, but are not limited to, uronium-based condensing agents such as 3-oxide hexafluorophosphate (HATU); acid anhydrides such as 2-methyl-6-nitrobenzoic anhydride (MNBA); 2-halopyridinium salts such as 2-chloro-1-methylpyridinium p-toluenesulfonate; propylphosphonic anhydride (cyclic trimer) (T3P); diphenylphosphoric azide (DPPA); and the like. If necessary, a general additive used together with a dehydrating condensing agent such as 1-hydroxybenzotriazole (HOBt) may be added. The dehydrating condensing agent can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II), and the additive can be used in an amount of 0.2 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 equivalent of the compound of formula (II).

[0033] The base may be one or more of the following, which may be appropriately selected and mixed: carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base may be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (II). The solvent may be any solvent inert to the reaction, and may be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water.

[0034] The reaction temperature for reaction B is about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0035] Reaction C can be carried out in the presence of a solvent, optionally with the addition of a base. The compound of formula (III) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II-a).

[0036] The base may be one or more of the following, which may be appropriately selected and mixed: carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base may be used in an amount of 0.1 to 10 equivalents, preferably 0.5 to 5 equivalents, relative to 1 equivalent of the compound of formula (II-a). The solvent may be any solvent inert to the reaction, and may be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; and water.

[0037] The reaction temperature for reaction C is about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0038] The compound of formula (II) used in reaction B and reaction C can be prepared according to the following reaction 1-1 or 1-2 or a known method, or a commercially available product can be used. The compound of formula (III) can be prepared according to the following reaction 2-2, 2-4 or 2-6. The compound of formula (II-a) used in reaction C can be produced from the compound of formula (II) according to a known method, or a commercially available product may be used.

[0039] [Reaction D] Reaction D is a method of deprotecting the Boc group of compound of formula (XX-c) to obtain a compound of formula (Ia) via a compound of formula (XX-d) or formula (XX-e). In addition, reaction D can also obtain a compound of formula (Ia) directly from a compound of formula (XX-c) without isolating the compound of formula (XX-d), formula (XX-e), or a mixture thereof.

[0040] [ka]

[0041] The symbols in the formula are as defined above. Reaction D can be carried out in a similar manner to Reaction A above.

[0042] [Reaction E] and [Reaction F] Reaction E is a method of reacting a compound of formula (XX-f) with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (XX-g). Reaction F is a method of reducing a compound of formula (XX-g) to obtain a compound of formula (XX-h). Reactions E and F can also be carried out consecutively without isolating the compound of formula (XX-g).

[0043] [ka]

[0044] In the formula, R 3a is H, (C 1 -C 2 )-alkyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or Z-substituted (C 1 -C 2 )-alkyl, and R 3b is H or methyl. R 3a and R 3b may be joined together to form a 3- or 4-membered carbocyclic ring (e.g., cyclopropyl or cyclobutyl), Y 1 is alkyl, and Y 2 is hydrogen or alkyl, and the other symbols are as defined above.

[0045] Reaction E can be carried out by adding an acid, a base or a dehydrating agent as necessary, and a solvent may be used. The compound of formula (IV-a) or formula (IV-b) is usually used in an amount of 1 to 5 equivalents relative to 1 equivalent of the compound of formula (XX-f), and may be used in excess if no problem occurs in the reaction.

[0046] The acid may be either an inorganic acid or an organic acid. Examples of inorganic acids include hydrochloric acid and sulfuric acid, and examples of organic acids include acetic acid, methanesulfonic acid, and paratoluenesulfonic acid. Examples of the base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and the like. Examples of the dehydrating agent include anhydrous magnesium sulfate, anhydrous sodium sulfate, and molecular sieves.

[0047] The solvent may be any solvent that is inert to the reaction, and may be appropriately selected from, for example, one or more of aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as acetonitrile; protic polar solvents such as methanol and ethanol; and water.

[0048] The reaction temperature for reaction E is about -20°C to 150°C, preferably about 0°C to 120°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0049] The compound of formula (IV-a) or formula (IV-b) used in reaction E can be produced according to a known method, or a commercially available product may be used.

[0050] Reaction F can be carried out usually in the presence of a reducing agent and a solvent, optionally with the addition of an acid, or by hydrogenation under a hydrogen atmosphere using palladium on carbon as a catalyst.

[0051] Examples of the reducing agent include sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and 2-picoline borane complex. The reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (XX-g). The acid to be added may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid, and examples of the organic acid include acetic acid and trifluoroacetic acid. The acid can be used in an amount of 1 to 10 equivalents per equivalent of the compound of formula (XX-g).

[0052] The solvent used when a reducing agent is used may be any solvent that is inert to the reaction, and may be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; protic polar solvents such as methanol and ethanol; and water.

[0053] The solvent used in the reaction using palladium carbon as a catalyst under a hydrogen atmosphere may be any solvent inert to the reaction, and may be appropriately selected from, for example, one or more of ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, and isopropanol; water; etc. If necessary, the reaction may be carried out under pressurized conditions.

[0054] The reaction temperature for reaction F is about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

[0055] [Reaction G] Reaction G is a method of deprotecting the Boc group of a compound of formula (XX-ga) to obtain a compound of formula (XX-gb).

[0056] [ka]

[0057] The symbols in the formula are as defined above. Reaction G can be carried out in a similar manner to Reaction A above.

[0058] [Reaction H] and [Reaction I] Reaction H is a method of reacting a compound of formula (II) with a compound of formula (V) to obtain a compound of formula (XX-g). Reaction I is a method of reacting a compound of formula (II-a) with a compound of formula (V) to obtain a compound of formula (XX-g).

[0059] [ka]

[0060] The symbols in the formula are as defined above. Reaction H can be carried out in accordance with the above reaction B. The compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II).

[0061] Reaction I can be carried out in accordance with the above reaction C. The compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.7 to 1.5 equivalents, per equivalent of the compound of formula (II-a).

[0062] The compound of formula (V) used in reactions H and I can be produced according to the following reaction 2-5 or a known method, or a commercially available product may be used.

[0063] [Reaction J] Reaction J is a method of obtaining a compound of formula (XX-j) by reacting a compound of formula (XX-i) with a compound of formula (VI).

[0064] [ka]

[0065] In the formula, L 1 is a leaving group, such as halogen, trifluoromethanesulfonyloxy, methanesulfonyloxy, paratoluenesulfonyloxy, etc., and R 3c (C 1 -C 3 )-alkyl, (C 3 -C 4 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 4 )-cycloalkyl, or (C 1 -C 3 )-alkyl, and the other symbols are as defined above.

[0066] Reaction J can be usually carried out in the presence of a base and a solvent, and optionally with the addition of a phase transfer catalyst. The compound of formula (VI) can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per equivalent of the compound of formula (XX-i).

[0067] The base may be one or more of alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; organolithium compounds such as n-butyllithium and lithium diisopropylamide; alkali metal carboxylates such as sodium acetate and potassium acetate; etc. The base may be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the compound of formula (XX-i). The solvent may be any solvent inert to the reaction, and may be appropriately selected from, for example, one or more of aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol, and tert-butanol; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and water. Examples of the phase transfer catalyst include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. The phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents relative to the compound of formula (XX-i).

[0068] The reaction temperature for reaction J is about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 48 hours, preferably about 1 to 24 hours.

[0069] The compound of formula (VI) used in reaction J can be produced according to a known method, or a commercially available product may be used.

[0070] [Reaction K] Reaction K is a method of obtaining a compound of formula (XX-b) by reacting a compound of formula (II-b) with a compound of formula (VII).

[0071] [ka]

[0072] The symbols in the formula are as defined above.

[0073] Reaction K can be carried out in accordance with the above reaction J. The compound of formula (VII) can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (II-b).

[0074] The compound of formula (II-b) used in reaction K can be produced according to the following reaction 1-3 or a known method, or a commercially available product may be used. The compound of formula (VII) used in reaction K can be produced according to a known method, or a commercially available product may be used.

[0075] The compounds used in Production Method 1 (Reactions A to K) can be produced according to the following Production Method 2 (Reactions 1-1 to 1-3 and Reactions 2-1 to 2-6) and a conventional salt production method, but are not limited to these methods. These compounds may be produced according to known methods, or commercially available products may be used.

[0076] manufacturing method 2 [Reaction 1-1], [Reaction 1-2] and [Reaction 1-3] Reaction 1-1 is a method of oxidizing a compound of formula (1) to obtain a compound of formula (II). Reaction 1-2 is a method of hydrolyzing a compound of formula (2) to obtain a compound of formula (II). Reaction 1-3 is a method of reacting a compound of formula (II) or a compound of formula (II-a) with a compound of formula (3) to obtain a compound of formula (II-b).

[0077] [ka]

[0078] The symbols in the formula are as defined above. Reaction 1-1 can be carried out under general Pinnic oxidation conditions, for example, according to the method described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.

[0079] The compound of formula (1) used in reaction 1-1 can be produced 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. Alternatively, a commercially available product may be used.

[0080] Reaction 1-2 can be carried out under general ester hydrolysis conditions, for example, in accordance with the method described in WO 2009 / 100171.

[0081] The compound of formula (2) used in reaction 1-2 can be produced in accordance with a known method, for example, the method described in WO 2012 / 006760, or a commercially available product may be used.

[0082] Reaction 1-3 can be carried out in accordance with the above reaction B or reaction C. The compound of formula (3) can be used in an amount of 0.5 to 10 equivalents, preferably 0.7 to 5 equivalents, per equivalent of the compound of formula (II) or the compound of formula (II-a).

[0083] The compound of formula (3) used in reaction 1-3 can be produced according to known methods, for example, the methods described in European Journal of Organic Chemistry, 2003, 4757-4764, Synthetic Communications, 2017, 47, 1231-1238, or commercially available products may be used.

[0084] [Reaction 2-1]~[Reaction 2-6] Reaction 2-1 is a method of reacting a compound of formula (10) with a compound of formula (3) to obtain a compound of formula (11). Reaction 2-2 is a method of reducing a compound of formula (11) to obtain a compound of formula (III). Reactions 2-1 and 2-2 can be carried out consecutively without isolating the compound of formula (11). Reaction 2-3 is a method of obtaining a compound of formula (11-b) by reacting a compound of formula (11-a) with a compound of formula (VI). Reaction 2-4 is a method for obtaining a compound of formula (III) by reacting a compound of formula (VII) with a compound of formula (3). Reaction 2-5 is a method of reacting a compound of formula (III-a) with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (V). Reaction 2-6 is a method of reducing a compound of formula (V) to obtain a compound of formula (III-b). Reactions 2-5 and 2-6 can be carried out consecutively without isolating the compound of formula (V).

[0085] [ka]

[0086] The symbols in the formula are as defined above. Reaction 2-1 can be carried out under general conditions for hydrazonization with aldehyde and hydrazine, for example, according to the method described in Tetrahedron Letters, 2013, 54, 896-899. The compound of formula (3) can be used in an amount of 0.7 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (10).

[0087] The compound of formula (10) used in reaction 2-1 can be produced according to a known method, or a commercially available product may be used.

[0088] Reaction 2-2 can be carried out under general conditions for reducing hydrazones to hydrazines, for example, according to the method described in U.S. Patent Application Publication No. 2016 / 002251 and Chemical Reviews, 2019, 119, 11857-11911. Reduction can also be carried out using 2-picoline borane complex, with the addition of an acid such as hydrochloric acid as necessary.

[0089] Reaction 2-3 can be carried out in accordance with known hydrazone alkylation conditions, for example, the methods described in Organic Letters, 2014, 16, 5940-5943, Chemistry-A European Journal, 2019, 25, 976-980, Journal of Organic Chemistry, 2006, 71, 7113-7116, etc.

[0090] Reaction 2-4 can be carried out in accordance with known hydrazine alkylation reactions, for example, methods described in U.S. Patent Application Publication No. 2012 / 0157386, Organic Letters, 2014, 16, 4782-4785, and WO 2018 / 221679.

[0091] Reaction 2-5 can be carried out in accordance with Reaction E, and Reaction 2-6 can be carried out in accordance with Reaction F.

[0092] Compound (I), which is the active ingredient of the present composition, is useful as an active ingredient of an agricultural and horticultural fungicide that can control plant diseases at a low dose. Compound (I) includes compound (IA), and therefore, compound (IA) is also included in the following description. Compound (I) can control plant diseases caused by plant pathogens belonging to Oomycetes, Phytomyxea, Zygomycota, Ascomycetes, Basidiomycetes, Deuteromycetes, etc. Among them, compound (I) is particularly effective in controlling plant diseases caused by plant pathogens belonging to Oomycetes and Phytomyxea.

[0093] Specific examples of the plant pathogenic fungi include the following. As oomycetes, potato or tomato Phytophthora infestans ( Phytophthora infesting ), Tomato gray rot fungus ( Phytophthora capsicum ) such as Phytophthora ( Phytophthora ) genus fungus; Cucumber downy mildew fungus ( Downy mildew Cuban ) such as Pseudoperonospora ( Downy mildew ) genus fungus; Grape downy mildew fungus ( Plasmopara vine-grower a) Plasmopara ( Plasmopara ) genus; rice seedling blight fungus ( Pythium grass-like plant ), wheat brown snow rot fungus ( Pythium iwayamai ) such as Pythium ( Pythium ) fungi causing radish root narrowing and spinach root rot; and Albugo macrospora fungi causing spinach white rust. Examples of Plasmodiophores include the genus Plasmodiophora brassicae, such as the Chinese cabbage clubroot fungus and the cabbage clubroot fungus, the genus Polymyxa betae, which transmits the Beet necrotic yellow vein virus, the genus Spongospora, such as the potato powdery scab fungus Spongospora subterranea, and the genus Olpidium virulentus, which transmits the Mirafiori lettuce big vein virus. As an ascomycete fungus, wheat powdery mildew fungus ( Erysipelas grass ) like Erysiphe ( Erysipelas ) genus fungus; cucumber powdery mildew fungus ( Spheroid sooty ), strawberry powdery mildew fungus ( Spheroid low ground ) like Sphaerotheca ( Spheroid ) genus fungus; Grape powdery mildew fungus ( Hook murderer ) such as Uncinula ( Hook ) genus fungus; Apple powdery mildew fungus ( Podosphere white-haired ) such as Podosphaera ( Podosphere ) genus fungus; Pea mycosis fungus ( Mycosphaerella pine trees ), Apple black spot fungus ( Mycosphaerella apples ), Banana black sigatoka fungus ( Mycosphaerella little music box ), Diospyros kaki leaf spot fungus ( Mycosphaerella Nawa ), strawberry snake eye disease fungus ( Mycosphaerella strawberries ) such as Mycosphaerella ( Mycosphaerella ) genus fungus; Apple spot fungus ( Ventura unequal ), Japanese pear spot fungus ( Ventura sweet potato ) like Venturia ( Ventura ) genus; barley net spot fungus ( Pyrenophora smooth ), barley leaf spot fungus ( Pyrenophora grass ) like Pyrenophora ( Pyrenophora ) genus fungi; various sclerotinia fungi such as Phaseolus sclerotinia, Cucumber sclerotinia, Cabbage sclerotinia, Chinese cabbage sclerotinia, Pepper sclerotinia, Green pepper sclerotinia, or Onion sclerotinia ( Sclerotinia sclerotia ), Wheat snow mold fungus ( Sclerotinia northern ), Tomato sclerotinia rot fungus ( Sclerotinia minor ), Alfalfa sclerotinia rot fungus ( Sclerotinia clover ) such as Sclerotinia ( Sclerotinia ) genus fungus; Peanut rot fungus ( Botryolinia peanuts ) such as Botryolina ( Botryolinia) Genus: Cochliobolus oryzae ( Snail Miyabean ) such as Cochliobolus ( Snail ) genus; Cucumber vine wilt fungus ( Didymel bryonia ) like Didimera ( Didymel ) genus; rice seedling disease fungus ( Gibberella fujikuroi ) such as Gibberella ( Gibberella ) genus bacteria; Grapevine black spot fungus ( Elsinore grapevine ), Citrus scab fungus ( Elsinoe fawcettii ) like Elsinoe ( Elsinore ) genus fungus; Citrus black spot fungus ( Diaporthe lemons ), Grapevine swell fungus ( Diaporthe Diaporce ( sp.) Diaporthe ) genus fungus; Monilia apple fungus ( Monilinia evil ), peach brown spot fungus ( Monilinia fruit-growing ) like Monilia ( Monilinia ) genus; Grape late rot fungus ( Glomerulus girdle ) like Glomerella ( Glomerulus ) genus bacteria. As a basidiomycete fungus, rice sheath blight fungus ( Rhizoctonia nightshade ) such as Rhizoctonia ( Rhizoctonia ) genus; Wheat smut fungus ( I burn. naked ) like Ustilago ( I burn. ) genus fungus; Oat crown rust fungus ( Powdery mildew crowned ), wheat leaf rust fungus ( Powdery mildew hidden ), wheat stripe rust fungus ( Powdery mildew striated ) such as Puccinia ( Powdery mildew ) genus fungus; soybean rust fungus ( Phakopsora pachyrhizome ) like Phakopsora ( Phakopsora ) genus fungus; Wheat or barley snow mold fungus ( Typhula incarnate , Typhula ishikariensis ) like Tifra ( Typhula ) genus bacteria. As a fungus imperfecti, wheat rot fungus ( Septoria knots ), wheat leaf spot fungus ( Septoria wheat ) like Septoria ( Septoria ) genus fungi; various gray mold fungi such as grape gray mold, citrus gray mold, cucumber gray mold, tomato gray mold, strawberry gray mold, eggplant gray mold, kidney bean gray mold, adzuki bean gray mold, pea gray mold, pea gray mold, peanut gray mold, pepper gray mold, lettuce gray mold, onion gray mold, statice gray mold, carnation gray mold, rose gray mold, pansy gray mold, or sunflower gray mold ( Botrytis gray ), onion gray rot fungus ( Botrytis garlic ), the pathogen that causes onion leaf blight caused by Botrytis sp. ( Botrytis scaly , Botrytis linen , Botrytis tulips ) such as Botrytis ( Botrytis ) fungi; Fusarium fungi such as Fusarium graminearum, Fusarium oxysporum, and rice blast fungus ( Firefly rice ) such as Pyricularia ( Firefly ) genus; Sugar beet brown spot fungus ( Cercospora betel nut ), Persimmon angular spot fungus ( Cercospora kakivola ) such as Circospora ( Cercospora ) genus fungus; Cucumber anthracnose fungus ( Colletotrichum to circle ) such as Colletotrichum ( Colletotrichum ) genus fungus; Apple leaf spot fungus ( Alternaria alternate apple pathotype), black spot fungus ( Alternaria alternate Japanese pear pathotype), potato summer blight or tomato ring spot fungus ( Alternaria nightshade ), cabbage or Chinese cabbage black spot fungus ( Alternaria cabbages ), Cabbage sooty mold fungus ( Alternaria small cabbage ), onion or leek black spot fungus ( Alternaria leek ) like Alternaria ( Alternaria ) genus fungus; Cabbage root rot fungus ( Phoma lingam ) like format( Food ) genus; Wheat eyespot fungus ( Pseudocercosporella herpotrichoid ) such as Pseudocircosporela ( Pseudocercosporella ) genus fungus; Grape brown spot fungus ( Pseudocercospora vine ) such as Pseudocircospora ( Pseudocercospora ) genus; barley cloud fungus ( Rhynchosporium rye ) such as Rhynchosporium ( Rhynchosporium ) genus fungus; peach spot fungus ( Cladosporium carpophilum ) such as Cladosporium ( Cladosporium ) genus; Peach rot fungus ( Phomopsis sp.) Phomopsis ) genus fungus; Oyster anthracnose fungus ( Gloeosporium khaki ) such as Gloeosporium ( Gloeosporium ) genus fungus; Tomato leaf mold fungus ( Fulvia yellow ) like Fulvia ( Fulvia) genus fungus; cucumber brown spot fungus ( Corynespora cashew nut ) such as Corynespora ( Corynespora ) genus bacteria.

[0094] Since compound (I) can control the various plant pathogenic fungi mentioned above, the composition can preventively or curatively control various diseases. In particular, the composition is effective against various diseases that are problematic in the agricultural and horticultural fields, such as rice blast caused by Pyricularia fungus, bakanae disease caused by Fusarium fungus, southern leaf spot caused by Cochliobolus fungus, and sheath blight caused by Rhizoctonia fungus; and wheat diseases such as powdery mildew caused by Erysiphe fungus, red mold head or crown rot caused by Fusarium fungus, rust caused by Puccinia fungus, brown snow rot caused by Pythium fungus, bare smut caused by Ustilago fungus, eyespot caused by Pseudocircosporella fungus, and leaf blight or stunt blight caused by Septoria fungus. ; Corn diseases such as Fusarium head blight, Phaeophaeria leaf spot, Puccinia rust, Setophaeria sooty blight, Cochliobolus leaf spot, Pythium root rot, and Ustilago smut; Gramineae diseases such as Ustilago leaf smut, Stagonospora leaf burn, Puccinia rust, Gibberella top rot, Caldariomyces sooty blight, and Pseudocircospora leaf blight. Crop diseases: Powdery mildew caused by Oidium, rust caused by Phakopsora, downy mildew caused by Peronospora, late blight caused by Phytophthora, anthracnose caused by Colletotrichum, sclerotinia rot caused by Sclerotinia, gray mold caused by Botrytis, root rot or damping-off caused by Fusarium; diseases of legume crops such as yellows caused by Fusarium, downy mildew caused by Peronospora, black spot caused by Alternaria, root rot caused by Phoma, clubroot caused by Plasmodiophora, and Aphanomycetes. Brassicaceae crop diseases such as root narrowing caused by Sclerotinia;Asteraceae crop diseases such as downy mildew caused by Bremia, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotinia rot caused by Sclerotinia, and rust caused by Aescidium;tomato diseases such as ring spot caused by Alternaria, leaf mold caused by Fulvia, late blight caused by Phytophthora, gray mold caused by Botrytis, powdery mildew caused by Oidium, wilt caused by Fusarium, and sooty mold caused by Pseudocircospora;Diseases of Solanaceae crops such as potato diseases such as summer blight caused by Alternaria, late blight caused by Phytophthora, sclerotinia rot caused by Sclerotinia, and dry rot caused by Fusarium; diseases of Cucurbitaceae crops such as anthracnose caused by Colletotrichum, powdery mildew caused by Sphaerotheca, vine blight caused by Didymella, downy mildew caused by Pseudoperonospora, late blight caused by Phytophthora, brown spot caused by Corynespora, and vine split caused by Fusarium; downy mildew caused by Peronospora, late blight caused by Phytophthora, gray mold caused by Botrytis, and Sclerotinia Diseases of Alliaceae crops such as sclerotinia caused by fungi and rust caused by Puccinia; diseases of Umbelliferae crops such as black leaf blight or black spot caused by Alternaria, gray mold caused by Botrytis, sclerotinia caused by Sclerotinia, powdery mildew caused by Erysiphe, and spot disease caused by Circospora; diseases of Liliaceae crops such as leaf blight caused by Botrytis, late blight caused by Phytophthora, and stem blight caused by Phomopsis; diseases of Polygonaceae crops such as downy mildew caused by Peronospora, powdery mildew caused by Erysiphe, and damping-off caused by Rhizoctonia; vine split caused by Fusarium, ceratopsis Diseases of Convolvulaceae crops such as black spot caused by Bacillus subtilis and damping-off caused by Streptomyces; diseases of Chenopodiaceae crops such as downy mildew caused by Peronospora, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotinia rot caused by Sclerotinia, powdery mildew caused by Oidium, and brown spot caused by Circospora; black rot caused by Elsinoe, late rot caused by Colletotrichum, powdery mildew caused by Erysiphe, downy mildew caused by Plasmopara, gray mold caused by Botrytis, brown spot caused by Pseudocircospora, and branch swelling caused by Diaporthe diseases of Vitaceae crops such as powdery mildew caused by Sphaerotheca, gray mold caused by Botrytis, anthracnose caused by Glomerella, and dry rot caused by Fusarium; diseases of strawberry such as Monilia disease caused by Monilia, powdery mildew caused by Podosphaera, leaf spot disease caused by Alternaria, black spot disease caused by Venturia, anthracnose caused by Glomerella, brown spot disease caused by Diplocarpon, ring spot disease caused by Botryosphaeria, sooty spot disease caused by Zygophiala, sooty spot disease caused by Gloeodes, and black spot disease caused by Mycosphaerella; diseases of apple such as Monilia disease caused by Monilia, powdery mildew caused by Podosphaera, leaf spot disease caused by Alternaria, black spot disease caused by Venturia, anthracnose caused by Glomerella, brown spot disease caused by Diplocarpon, ring spot disease caused by Botryosphaeria, sooty spot disease caused by Zygophiala, sooty spot disease caused by Gloeodes, and black spot disease caused by Mycosphaerella;Diseases of pears such as black spot caused by Venturia, black spot caused by Alternaria, powdery mildew caused by Phyllactinia, late blight caused by Phytophthora, and fruit rot caused by Fusarium; diseases of Rosaceae crops such as brown spot caused by Monilinia, black spot caused by Cladosporium, and Phomopsis rot caused by Phomopsis; black spot caused by Diaporthe, common scab caused by Elsinoe, and fusariaceous rot caused by Fusarium; It is effective in controlling plant diseases such as citrus diseases such as damping-off and other diseases of Rutaceae crops; diseases of Ebenaceae crops such as anthracnose caused by Gloeosporium, leaf spot caused by Circospora, powdery mildew caused by Phyllactinia, and sooty spot caused by Zygophiala; and diseases of Theaceae crops such as anthracnose caused by Colletotrichum, ring spot caused by Pestaloothiopsis, red burn caused by Pseudomonas, and blast caused by Camellia.

[0095] Also, diseases of wheat such as red mold or crown rot caused by Fusarium, anthracnose caused by Colletotrichum, cattle smut caused by Chiletia, bare smut caused by Ustilago, stripe disease caused by Cephalosporium, and spot blight caused by Septoria; diseases of corn such as southern leaf spot caused by Bipolaris, anthracnose caused by Colletotrichum, and seedling damping-off caused by Fusarium; and red rot caused by Glomerella. Diseases of Gramineae crops such as sugarcane diseases such as black rot caused by Ceratocystis and downy mildew caused by Sclerospora; diseases of Legumes crops such as soybean diseases such as purple spot caused by Circospora, downy mildew caused by Peronospora, damping-off caused by Fusarium, brown spot caused by Septoria, black spot caused by Diaporthe, anthracnose caused by Colletotrichum, and sleeping disease caused by Septogloeum; black spot caused by Alternaria brassicae, Alternaria Cabbage diseases such as black sooty mold caused by Brassicola, downy mildew caused by Peronospora, black spot bacterial disease caused by Pseudomonas, black rot caused by Xanthomonas, and root rot caused by Phoma; radish diseases such as black spot caused by Alternaria, yellows caused by Fusarium, and black rot caused by Xanthomonas; cruciferous crop diseases such as Chinese cabbage diseases such as black spot caused by Alternaria, black rot caused by Xanthomonas, and yellowing disease caused by Verticillium; tomato diseases such as ring spot caused by Alternaria, canker caused by Clavibacter, and bacterial spot disease caused by Xanthomonas; eggplant diseases such as brown spot caused by Alternaria and brown spot caused by Phomopsis; common scab caused by Streptomyces, Helminthos Solanaceae crop diseases such as potato diseases caused by silver scab caused by Porium and powdery scab caused by Spongospora; Cucurbitaceae crop diseases such as black spot caused by Alternaria, bacterial spot caused by Pseudomonas, and brown spot caused by Xanthomonas; Liliaceae crop diseases such as black spot caused by Alternaria, gray rot or mycelial rot caused by Botrytis, dry rot caused by Fusarium, and downy mildew caused by Peronospora; carrot diseases such as black leaf blight or black spot caused by Alternaria, and bacterial spot caused by Xanthomonas; Umbelliferae crop diseases such as celery diseases such as leaf blight caused by Septoria, sclerotinia rot caused by Sclerotinia, and bacterial leaf blight caused by Pseudomonas;It is also effective against seed-borne diseases of Chenopodiaceae crops, such as downy mildew caused by Peronospora, wilt caused by Fusarium, and anthracnose caused by Colletotrichum, which are diseases of spinach. Furthermore, it is also effective in controlling soil diseases caused by plant pathogens such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodiophora, and Thielaviopsis.

[0096] Application of compound (I) to plants causes little change in the appearance of the treated plants (such as yellowing or withering of leaves), and therefore the composition containing compound (I) as an active ingredient has the characteristic of being environmentally friendly. Furthermore, since compound (I) has excellent rain resistance, residual activity, and penetration, by applying the composition containing compound (I) as an active ingredient to a plant body, harmful fungi on the above-ground parts of the plant can be controlled for a certain period of time.

[0097] The composition can be applied to plants, plant pathogens or soil to control various plant diseases. The plant body means above-ground parts of a plant such as trunks, stems, leaves, flowers and fruits, and underground parts of a plant such as seeds, tubers, rhizomes, roots, seedlings and transplants. The soil means agricultural land such as fields, paddy fields, orchards, and non-agricultural land such as lawns and forests where plants are cultivated.

[0098] The plant to which the composition is applied is not particularly limited as long as it is useful in agriculture and horticulture. For example, Gramineae crops (rice, wheat, barley, oats, rye, corn, sugarcane, etc.), Legumes crops (soybeans, kidney beans, adzuki beans, peas, peanuts, etc.), Cruciferae crops (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, rapeseed, rapeseed, etc.), Asteraceae crops (lettuce, burdock, garland chrysanthemum, etc.), Solanaceae crops (potatoes, eggplants, tomatoes, bell peppers, tobacco, chili peppers, etc.), Cucurbitaceae crops (cucumbers, pumpkins, melons, watermelons, etc.), Liliaceae crops (leeks, Chinese chives, shallots, garlic, onions, etc.), Umbelliferae crops (celery, carrots, parsley, etc.), Liliaceae crops (lilies, tulips, asparagus, etc.), Polygonaceae (buckwheat, etc.), Leeks These include crops from the family Globaceae (sweet potato, etc.), family Chenopodiaceae (spinach, sugar beet, etc.), family Vitaceae (grapes, etc.), family Rosaceae (roses, strawberries, apples, pears, peaches, loquats, almonds, etc.), family Rutaceae (tangerines, lemons, oranges, citrus, etc.), family Ebenaceae (persimmons, etc.), family Theaceae (tea, etc.), family Oleaceae (olive, jasmine, etc.), family Malvaceae (cotton, cacao, okra, etc.), family Musaceae (bananas, etc.), family Zingiberaceae (ginger, etc.), family Rubiaceae (coffee trees, etc.), family Pinellidaceae (pineapple, ananas, etc.), family Plumeriaceae (static), family Caryophyllaceae (carnation), family Violaceae (pansy), and family Asteraceae (sunflower).

[0099] The plants include plants bred using genetic engineering or gene editing techniques, such as plants that have been endowed with environmental stress resistance, herbicide resistance, pest resistance, disease resistance, or the like, or plants that have been modified in terms of growth, fertility, product quality, yield, or the like.

[0100] The present composition is usually prepared by mixing compound (I) with a solid or liquid carrier, and adding surfactants and other formulation adjuvants as necessary to prepare it in various forms such as dusts, granules, granular water-dispersible agents, wettable powders, aqueous suspensions, oily suspensions, water-soluble agents, emulsions, liquids, pastes, aerosols, micro-duspers, and microcapsules. However, as long as the composition is suitable for the object of the present invention, it may be prepared in any formulation form commonly used in the art. The solid carrier, the liquid carrier, the surfactant, and the formulation auxiliary are solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, baking soda, Glauber's salt, zeolite, and starch; liquid carriers such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkyl ester ... anionic surfactants and spreaders such as aryl sulfates, alkyl diglycol ether sulfates, alcohol sulfates, alkyl sulfonates, alkylaryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates, alkylaryl phosphates, styrylaryl phosphates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylaryl phosphates, and salts of naphthalenesulfonic acid formalin condensates;Examples of such surfactants and spreading agents include nonionic surfactants and spreading agents such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, acetylene glycol, acetylene alcohol, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylaryl ethers, polyoxyethylene glycol alkyl ethers, polyethylene glycols, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid esters; and vegetable oils and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffin. As for each component of these adjuvants, one or more types may be appropriately selected and used as long as it does not deviate from the object of the present invention. In addition to the above-mentioned adjuvants, those known in the art may be appropriately selected and used, and various commonly used adjuvants such as bulking agents, thickening agents, antisettling agents, antifreezing agents, dispersion stabilizers, phytotoxicity reducing agents, and antifungal agents may also be used. The mixing ratio of compound (I) to various adjuvants is 0.001:99.999-95:5, preferably 0.005:99.995-90:10. When these preparations are actually used, they may be used as they are, or diluted to a predetermined concentration with a diluent such as water, and various spreading agents (surfactants, vegetable oils, mineral oils, etc.) may be added as necessary.

[0101] The application of the present composition cannot be generally specified due to differences in weather conditions, formulation form, target crop, application time, application location, type and occurrence of plant diseases, etc., but the present composition or its dilution can be applied by a commonly used application method, i.e., spray treatment, soil treatment, seed treatment, etc. In general, in the case of spray treatment, the appropriate application amount can be about 10 to 100,000 g of the present composition per hectare. In the case of soil treatment, the appropriate application amount can be about 0.01 to 1,000 g of the present composition per hectare. In the case of seed treatment, the appropriate application amount can be about 0.001 to 100 g of the present composition per 1 kg of seeds, preferably about 0.01 to 1 g.

[0102] The spray treatment is a treatment method for controlling plant pathogens by spraying an effective amount of the composition onto the surface of the trunk, buds, stems, leaves, flowers, spikes, or fruits of a plant, or onto plant pathogens. Examples of the spray treatment include spraying onto stems and leaves, and spraying onto tree trunks. The soil treatment is a method of treating soil with the present composition in order to allow an effective amount of compound (I) to penetrate and move from the roots of a plant to the inside of the plant in order to protect crops from damage caused by plant pathogens. Examples of the treatment include irrigation treatment (irrigating the present composition into the soil for plant cultivation), soil incorporation treatment (mixing the present composition with the soil for plant cultivation), planting hole treatment, treatment at the base of a plant or between plants (spraying or irrigation), and incorporation treatment into soil used in culture soil, seedling boxes, seedling trays, paper pots, seedling beds, etc. The seed treatment is a treatment method for controlling plant pathogens by treating the seeds, bulbs, etc. of crops with the present composition directly or in the vicinity thereof in order to protect crops from damage caused by plant pathogens. Examples of the treatment include coating treatment, dressing treatment, and immersion treatment. Other examples include seedling treatment (irrigation or immersion), immersion treatment of bulbs, tubers, bulbs, roots, etc., and hydroponic treatment such as mixing with a hydroponic nutrient solution. Treatment may be performed on the whole plant or a part of it (stems, leaves, buds, flowers, ears, fruits, trunks, seeds, bulbs, tubers, bulbs, roots, etc.).

[0103] The present composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural chemicals, fertilizers, safeners, etc., and in this case, even more excellent effects and activity may be exhibited. The above-mentioned mixture or combination use means that the present composition and other components are used simultaneously, separately or with an interval of time. Other agricultural and horticultural drugs include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. In particular, the present composition and a mixed fungicide composition in which one or more active ingredient compounds of other fungicides are mixed or used in combination may improve the scope of application, timing of drug treatment, control activity, etc. in a favorable direction. The present composition and the active ingredient compounds of other fungicides may be formulated separately and mixed at the time of spraying, or both may be formulated together and used. Such mixed fungicides are also included in the present invention.

[0104] The mixing ratio of compound (I) and other fungicide active ingredient compounds cannot be specified in general due to differences in weather conditions, formulation form, target crop, application time, application site, type and occurrence of plant disease, etc., but can generally be 1:300-300:1, preferably 1:100-100:1. The appropriate application amount is 0.1-70,000g, preferably 1-30,000g, of the total active ingredient compound per hectare. The present invention also includes a method for controlling plant diseases by applying such a mixed fungicide composition.

[0105] When applying the fungicidal composition containing compound (I), other agricultural and horticultural chemicals such as fungicides, insecticides, acaricides, nematicides, soil pesticides, antiviral agents, attractants, herbicides, plant growth regulators, etc. may also be used in combination.

[0106] Among the above-mentioned other agricultural and horticultural agents, the active ingredient compound (common name) of the fungicide can be appropriately selected, for example, from the following compound group. Even if not specifically stated, when these compounds have various structural isomers such as salts, alkyl esters, and optical isomers, these are of course also included.

[0107] Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate azole compounds such as fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipfentrifluconazole, and mefentrifluconazole; quinoxaline compounds such as quinomethionate; Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, and thiram; Organochlorines such as fthalide, chlorothalonil, and quintozene; Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, and fuberiazole; Cyanoacetamide compounds such as cymoxanil; Acylamino acid compounds such as metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, ofurace, benalaxyl, benalaxyl-M (also known as chiralaxyl, furalaxyl), and valifenalate; Anilides such as cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, and pyraziflumid; Sulfamides such as dichlofluanid; Copper compounds such as cupric hydroxide, oxine copper, anhydrous copper sulfate, copper nonylphenolsulfonate, copper 8-hydroxyquinoline, and copper dodecylbenzenesulfonate (bis(ethylenediamine)copper(II) complex salt (also known as DBEDC); Organophosphates such as fosetyl-Al, tolclofos-methyl, edifenphos, and iprobenfos; Phthalimides such as captan, captafol, and folpet; Dicarboximide compounds such as procymidone, iprodione, and vinclozolin; Benzanilide compounds such as flutolanil, mepronil, and benodanil; Amide compounds such as carpropamid, diclocymet, silthiopham, and fenoxanil; pyrazolecarboxamide compounds such as benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, sedaxane, isoflucipram, inpyrfluxam, pyrapropoyne; benzamide compounds such as fluopicolide, fluopyram, zoxamide, and fluopimomide; Furanilide compounds such as fenfuram; Thiophene amide compounds such as isofetamide; Piperazine compounds such as triforine; Pyridine compounds such as pyrifenox, pyrisoxazole, and aminopyrifen; Pyrimidine compounds such as fenarimol, ferimzone, and nuarimol; Piperidine compounds such as fenpropidin; Morpholine compounds such as fenpropimorph, 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; strobilurin compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, enestroburin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, phenaminestrobin, flufenoxystrobin, triclopyricarb, and mandestrobin; Oxazole compounds such as famoxadone and oxathiapiprolin; Thiazolecarboxamide compounds such as ethaboxam; Imidazolinone compounds such as fenamidone; Benzenesulfonamide compounds such as flusulfamide; Oxime ether compounds such as cyflufenamid; Anthraquinone compounds such as dithianon; Crotonic acid compounds such as meptyldinocap; Antibiotics such as validamycin, kasugamycin, streptomycin, polyoxins; Guanidine compounds such as iminoctadine and dodine; quinoline compounds such as tebufloquin, quinoxyfen, quinofumelin, and ipflufenoquin; Thiazolidine compounds such as flutianil; Carbamate compounds such as propamocarb hydrochloride, pyribencarb, and tolprocarb; Tetrazole compounds such as picarbutrazox and methyltetraprole; Sulfonamide compounds such as amisulbrom and cyazofamid; Aryl phenyl ketone compounds such as metrafenone and pyriophenone; Benzothiazole compounds such as probenazole and dichlobentiazox; Phenylpyrazole compounds, such as fenpyrazamine; Dithiolane compounds such as isoprothiolane; Picolinamide compounds such as fenpicoxamid and florylpicoxamid; Sulfur, sulfur-based compounds such as lime sulphur; Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam-sodium, proquinazid, spiroxamine, dipymetitrone, etc.; Microbial germicides such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, Trichoderma atroviride SKT-1; and Plant extracts such as tea tree oil.

[0108] Among the above other agricultural and horticultural agents, the active ingredient compounds (common names) of the insecticides, nematicides, acaricides, or soil pesticides can be appropriately selected, for example, from the following compound groups. Even if not specifically stated, when these compounds have various structural isomers such as salts, alkyl esters, and optical isomers, these are of course also included.

[0109] Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN((RS)-(O-ethyl O-4-nitrophenyl phenylphosphonothioate), diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl os-methyl), propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, oxydeprofos (also known as ESP), azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos,Organophosphate compounds such as imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, and phorate; Carbamate compounds such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC (3,5-xylyl methylcarbamate), and fenothiocarb; Nereistoxin derivatives such as cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan; Organochlorines such as dicofol, tetradifon, endosulfan, dienochlor, and dieldrin; Organometallic compounds such as fenbutatin oxide and cyhexatin; Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin, deltamethrin, cyhalothrin, gamma-cypermethrin mma-cyhalothrin, lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, etofenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvalinate (fluvalinate), cycloprothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin, allethrin, tau-fluvalinate tau-fluvalinate, tralomethrin, profluthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin,Pyrethroid compounds such as silafluofen and chloroprallethrin; Benzoyl urea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron, noviflumuron, and fluazuron; Juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb, and diofenolan; Pyridazinone compounds such as pyridaben; pyrazole compounds such as fenpyroximate, fipronil, ethiprole, acetoprole, pyrafluprole, pyriprole, cyenopyrafen, and flufiprole; Pyrazolecarboxamide compounds such as pyflubumide, tebufenpyrad, and tolfenpyrad; Pyridylpyrazole compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, and tyclopyrazoflor; Neonicotinoid compounds such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran, and nithiazine; Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, and halofenozide; Pyridine compounds such as pyridalyl and flonicamid; tetronic acid compounds such as spirodiclofen and spiromesifen; Tetramic acid compounds such as spirotetramat and spiropidione; Strobilurins such as fluacrypyrim and pyriminostrobin; Pyrimidinamine compounds such as flufenerim and pyrimidifen; Organosulfur compounds such as malathion; Urea compounds such as flufenoxuron; Triazine compounds such as cyromazine; Hydrazone compounds such as hydramethylnon; Diamide compounds such as flubendiamide, broflanilide, and cyhalodiamide; Thiourea compounds such as diafenthiuron and chloromethiuron; Formamidine compounds such as amitraz, chlordimeform, and chloromebuform; Pyridine azomethine compounds such as pymetrozine and pyrifluquinazone; Isoxazolines such as afoxolaner, fluralaner, fluxametamide, and sarolaner; Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, sulfluramid, and hydramethyl. Compounds such as hydramethylnon, metaldehyde, sulfoxaflor, fluensulfone, verbin, dichloromezotiaz, triflumezopyrim, fluhexafon, tioxazafen, afidopyropen, flometoquin, flupyradifurone, fluazaindolizine, acinonapyr, benzpyrimoxan, flupyrimin, oxazosulfyl, and the like. The composition of the present invention may be applied in combination with the following compounds. Microbial pesticides such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or crystal protein toxins produced by Bacillus thuringiensis, insect pathogenic virus agents, insect pathogenic fungal agents, nematode pathogenic fungal agents, etc.; Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram; Natural products such as azadirachtin, rotenone, and ryanodine; repellents such as deet; Physical control agents such as paraffin oil, mineral oil.

[0110] Preferred embodiments of the present invention are as follows, but the present invention is not limited to these. [1] A bactericidal composition comprising a compound represented by formula (I) or a salt thereof. [2] A method for controlling harmful plant diseases, which comprises a step of applying an effective amount of a compound represented by formula (I) or a salt thereof to a plant body, a plant pathogen, or soil. [3] A compound represented by formula (IA) or a salt thereof. [4] R 3A is methyl, ethyl, or propargyl, or a salt thereof according to [3] above. [5] An agricultural and horticultural fungicide comprising the compound or salt thereof according to [3] to [4] above. [6] A method for controlling harmful plant diseases, comprising a step of applying the compound or salt thereof according to [3] to [4] above to a plant body, a plant pathogen, or soil. EXAMPLES

[0111] Examples of the present invention will now be described, but the present invention is not limited to these.

[0112] [Synthesis example] Synthesis Example 1: Synthesis of 2-amino-4-chloro-N-(2-chloro-5-fluorobenzyl)-N'-methylthiazole-5-carbohydrazide (Compound No. 33) (1) 2-chloro-5-fluorobenzaldehyde (1.50 g) dissolved in a small amount of methanol was added to a solution of 1-Boc-1-methylhydrazine (1.66 g) and triethylamine (1.58 mL) in methanol (50 mL), and the mixture was stirred overnight at room temperature. Then, 2-picoline borane (1.52 g, 85%) was added under ice cooling, followed by slow addition of 3N aqueous hydrochloric acid (15.77 mL), and the mixture was stirred at room temperature for 2.5 hours to obtain a reaction solution. The reaction solution was quenched using a saturated aqueous sodium bicarbonate solution. The quenched reaction solution was made basic using a 3N aqueous sodium hydroxide solution, and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to give oily tert-butyl 2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (1.28 g). 1 H NMR (CDCl 3 / 300MHz):δ(ppm)= 7.32 (dd, 1H), 7.14 (dd, 1H), 6.94 (td, 1H), 4.78 (brs, 1H), 4.04 (d, 2H), 2.98 (s, 3H), 1.45 (s, 9H).

[0113] (2) Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182. To a solution of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid (0.30 g) synthesized based on tetrahydrofuran (10 mL), oxalyl chloride (0.27 g) and a catalytic amount of N,N-dimethylformamide were added under ice cooling, and the mixture was stirred at 40 ° C for 3 hours to obtain a reaction solution. After cooling, the reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid chloride. Next, sodium hydride (0.04 g, 60%) was added to a solution of tert-butyl 2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.26 g) in tetrahydrofuran (3 mL) under ice cooling, and the mixture was stirred at the same temperature for 15 minutes to obtain a reaction solution. The reaction solution was added with a solution of the prepared carboxylic acid chloride in tetrahydrofuran (10 mL), and stirred at room temperature for 4 hours to obtain a reaction solution. After the reaction was completed, a saturated aqueous solution of sodium bicarbonate was added to the reaction solution under ice cooling to quench the reaction. The quenched reaction solution was made basic using a 3N aqueous solution of sodium hydroxide, and the aqueous layer was extracted with ethyl acetate and heptane. The organic layer was then washed with a 3N aqueous solution of sodium hydroxide and saturated saline, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain a gum-like tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.36 g). 1 H NMR (CDCl 3 / 300MHz):δ(ppm)= 8.65 (brs, 1H), 7.37-7.31 (m, 2H), 7.02-6.95 (m, 1H), 5.10 (brs, 1H), 4.78 (d, 1H), 3.00 (brs, 3H), 1.53 (s, 9H), 1.34 (brs, 9H).

[0114] (3) To a solution of tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.36 g) and 2,6-dimethylpyridine (0.91 mL) in dichloromethane (2.6 mL), trimethylsilyl trifluoromethanesulfonate (1.17 mL) was added under ice cooling. After stirring at the same temperature for 15 minutes, the mixture was stirred at room temperature overnight to obtain a reaction solution. Then, under ice cooling, a saturated aqueous solution of ammonium chloride was slowly added to the reaction solution to quench the reaction. The quenched reaction solution was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethanol / ethyl acetate / heptane) to obtain the target product (0.20 g) as a solid. 1 H NMR (acetone-d 6 / 300MHz):δ(ppm)= 7.51-7.45 (m, 1H), 7.15-7.08 (m, 2H), 6.91 (brs, 2H), 4.93 (s, 2H), 4.80 (q, 1H), 2.64 (d, 3H).

[0115] Synthesis Example 2: Synthesis of 2-amino-4-chloro-N-(4-fluoro-2-methylbenzyl)-N'-methylthiazole-5-carbohydrazide (Compound No. 105) (1) A solution of 4-fluoro-2-methylbenzaldehyde (1.0g) and 1-Boc-1-methylhydrazine (1.06g) in ethanol (35mL) was stirred at 75°C. After cooling to room temperature, 2-picoline borane (1.82g, 85%) and 3N aqueous hydrochloric acid (12mL) were added, and the mixture was stirred at room temperature overnight to obtain a reaction mixture. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the resulting reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain oily tert-butyl 2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (1.68g). 1 H NMR (CDCl 3 / 300MHz):δ(ppm) = 7.23-7.18 (m, 1H), 6.90-6.80 (m, 2H), 4.53 (brs, 1H), 3.92 (s, 2H), 2.92 (s, 3H), 2.42 (s, 3H), 1.49 (s, 9H).

[0116] (2) To a solution of 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid (230 mg) in tetrahydrofuran (10 mL), oxalyl chloride (0.1 mL) and N,N-dimethylformamide (4 mg) were added at 0° C. and stirred under a nitrogen atmosphere. The reaction temperature was raised to room temperature after 10 minutes, and then to 45° C. after 30 minutes. After stirring for a total of 1.5 hours, the mixture was cooled to room temperature to obtain a reaction mixture. The reaction mixture was concentrated under reduced pressure to obtain a carboxylic acid chloride. To a solution of tert-butyl 2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (150 mg) in tetrahydrofuran (5 mL), sodium hydride (23 mg, 60%) was added at 0° C. After stirring for 15 minutes, a solution of the carboxylic acid chloride in tetrahydrofuran (5 mL) was added, and the mixture was stirred at 75° C. for 3 hours under a nitrogen atmosphere to obtain a reaction mixture. The reaction mixture was allowed to cool to room temperature, and then water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated saline. It was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain oily tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (248 mg). 1 H NMR (DMSO-d 6 / 300MHz):δ(ppm) = 12.06 (s, 1H), 7.31-7.26 (m, 1H), 7.11-6.98 (m, 2H), 5.04-5.00 (m, 1H), 4.69-4.51 (1H, m), 2.92 (brs, 2H), 2.73 (brs, 1H), 2.33 (s, 3H), 1.34-1.09 (m, 18H).

[0117] (3) tert-Butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (248 mg) and 2,6-dimethylpyridine (0.55 mL) in dichloromethane (5 mL) were added with trimethylsilyl trifluoromethanesulfonate (0.68 mL) at room temperature, and the mixture was stirred overnight under heating and reflux to obtain a reaction mixture. After the reaction was completed, the reaction mixture was allowed to cool to room temperature, and then a saturated aqueous ammonium chloride solution was added. Ethyl acetate was further added and extracted. The organic layer was washed successively with a saturated aqueous sodium bicarbonate solution, water, and saturated saline, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (108 mg) as a solid. 1 H NMR (DMSO-d 6 / 300MHz):δ(ppm) = 7.61 (brs, 2H), 7.15 (dd, 1H), 7.07-6.97 (m, 2H), 5.05 (q, 1H), 4.69 (s, 2H), 2.40 (d, 3H), 2.28 (s, 3H).

[0118] Next, representative examples of compound (I) are specifically listed in Table 1. These compounds can be synthesized based on the above-mentioned production methods and synthesis examples, as well as methods known in the art. In the table, No. indicates the compound No. For the compounds described as NMR in the physical properties column of Table 1, the 1H-NMR spectrum data is shown in Table 2. 2 , R 3 , R 4 The abbreviations used in the columns represent the following substituents: Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, c-Pr is a cyclopropyl group, c-Bu is a cyclobutyl group, CN is a cyano group, and NO 2 indicates a nitro group, di indicates two, tri indicates three, and tetra indicates four. AlsoIn the case of a salt of compound (I), the type of salt is indicated in the column of physical properties in Table 1. For example, in the column of physical properties in Table 1, a compound described as HCl salt indicates a hydrochloride, and a compound described as TsOH salt indicates a paratoluenesulfonate. For example, compound No. 254 is the hydrochloride of compound No. 1, compound No. 255 is the hydrochloride of compound No. 76, and compound No. 256 is the hydrochloride of compound No. 78. Compound No. 257 is the paratoluenesulfonate of compound No. 1, compound No. 258 is the paratoluenesulfonate of compound No. 76, and Compound No. 257 is a paratoluenesulfonate salt of compound No. 78.

[0119] In Table 2 1 In H-NMR data, s indicates singlet, brs indicates broad singlet, d indicates doublet, t indicates triplet, q indicates quartet, sext indicates sextet, and m indicates multiplet.

[0120] R in Table 1 4 The positions of the substituents shown in the columns are as follows:

[0121] [ka] For example, R 4 The compound with "2-Me" in the n column and 1 in the n column has one R at the substituent position given in the chemical structure above. 4 This indicates that the compound is substituted with a methyl group, i.e., only the 2-position of the benzene ring is substituted with methyl, i.e., the compound is "n=1".

[0122] [Table 1]

[0123] [Table 2]

[0124] [Table 3]

[0125] [Table 4]

[0126] [Table 5]

[0127] [Table 6]

[0128] [Table 7]

[0129] [Table 8]

[0130] [Table 9]

[0131] 1 H-NMR data 1 H-nuclear magnetic resonance spectroscopy; δ is the chemical shift value (ppm)] are shown in Table 2.

[0132] [Table 10]

[0133] [Table 11]

[0134] [Table 12]

[0135]

Table 13

[0136]

Table 14

[0137]

Table 15

[0138]

Table 16

[0139]

Table 17

[0140]

Table 18

[0141]

Table 19

[0142]

Table 20

[0143]

Table 21

[0144]

Table 22

[0145] [Test example] Preparation of drug solution containing compound (I): Compound (I) was mixed with acetone or dimethyl sulfoxide to dissolve compound (I). After dissolving compound (I), water was added to dilute compound (I), which is an active ingredient, to a predetermined concentration (400 ppm, 200 ppm, or 100 ppm). This solution was used in the following Test Examples 1 to 3.

[0146] Test Example 1: Fungicidal effect test against tomato late blight (preventive effect test) Tomatoes were grown in vinyl pots with a diameter of 6 cm, and when they reached the 4.5 to 5.5 leaf stage, 10 ml of the drug solution was sprayed with a spray gun. After the drug solution dried (on the day of treatment), a spore suspension of Phytophthora infestans was sprayed and inoculated, and the plants were placed in an inoculation box at a temperature of 20°C and a humidity of 95% or more for 16 hours. Thereafter, the plants were placed in a thermostatic chamber at 20°C, and 3 days after inoculation, the lesion area rate was investigated, and the control rate was calculated according to the following calculation formula. As a result, each composition containing the following compounds (active ingredient concentration 400 ppm or 200 ppm) showed a control rate of 90% or more against tomato late blight. Compounds with underlined compound numbers showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. [Calculation formula for control rate] Control rate (%) = 100 - (X / Y) x 100 X: Lesion area rate of test compound (%), Y: Lesion area rate of untreated area (%) Compound: No. 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 62, 64, 65, 66, 67, 68, 70, 71, 72, 73, 74, 76, 77, 78, 79, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 105 , 106, 107, 111, 112, 113, 114, 115, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 130, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160 , 163, 164, 165, 166, 167, 170, 171, 172, 173, 174, 177, 178 , 179 , 180, 181, 182, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 195, 196, 198, 199, 241, 249, 250 In addition, each composition containing the following compounds (active ingredient concentration: 100 ppm) showed a control rate of 90% or more against tomato late blight. Compound: No. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 44, 48, 50, 51, 54, 55, 56, 57, 58, 60, 61, 62, 64, 65, 66, 67, 68, 70, 71, 72, 73, 75, 76, 77, 78, 79, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 105, 106, 107, 111, 112, 113, 114, 115, 116, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 130, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 149, 150, 151, 152, 153, 154, 155 , 156, 157, 158, 159, 160, 163, 164, 165, 166, 167, 170, 171, 172, 173, 174, 177, 178, 180, 181, 182, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 195, 196, 199, 241, 249

[0147] Test Example 2: Fungicidal effect test against cucumber downy mildew (preventive effect test) Cucumbers were grown in vinyl pots with a diameter of 6 cm, and when they reached the 1.2 to 1.5 leaf stage, 10 ml of the drug solution was sprayed with a spray gun. After the drug solution dried (on the day of treatment), a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis) was sprayed and inoculated, and the plants were placed in an inoculation box at a temperature of 20°C and a humidity of 95% or more for 24 hours. Thereafter, the plants were placed in a thermostatic chamber at 20°C, and 7 days after inoculation, the lesion area rate was investigated, and the control rate was calculated using the same calculation formula as in Test Example 1 above. As a result, each composition containing the following compounds (active ingredient concentration 400 ppm) showed a control rate of 90% or more against cucumber downy mildew. Compound No.1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 13, 14, 15, 17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 30, 31, 32, 33, 34, 39, 40, 41, 42, 46, 47, 48, 50, 51, 54, 55, 56, 58, 60, 62, 65, 66, 67, 68, 70, 71, 72, 73, 76, 77, 78, 79, 83, 84, 85, 86, 87, 89, 90, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 106, 111, 112, 113 , 114, 115, 119, 120, 121, 122, 123, 125, 126, 127, 128, 130, 132, 134, 135, 137, 138, 139, 140, 141, 142, 143, 144, 150, 151, 152, 154, 155, 157, 158, 159, 164, 165, 166, 167, 170, 172, 173, 174, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 196, 199, 241, 242

[0148] Test Example 3: Fungicidal effect test against tomato late blight (therapeutic effect test) Tomatoes were grown in vinyl pots with a diameter of 6 cm, and when they reached the 4.5-5.5 leaf stage, they were inoculated by spraying a spore suspension of Phytophthora infestans, and placed in an inoculation box with a temperature of 20°C and a humidity of 95% or more for 4 hours. Then, 10 ml of the liquid was sprayed with a spray gun, and after the liquid dried (on the day of treatment), the pot was placed in a thermostatic chamber at 20°C, and the lesion area rate was investigated 3 days after inoculation, and the control rate was calculated using the same calculation formula as in Test Example 1 above. As a result, each composition containing the following compounds (active ingredient concentration 400 ppm or 200 ppm) showed a control rate of 90% or more against tomato late blight. Compounds with underlined compound numbers showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. Compound: No. 1, 3, 4, 9, 10, 13, 14, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 30, 31, 32, 33, 34, 35 , 39, 40, 41, 42, 46, 47, 50, 51, 54, 55, 56, 57, 60, 62, 64, 66, 67, 68, 72, 76, 77, 78, 79, 83, 84, 85, 86, 87, 89, 90, 95, 96, 97, 98, 101, 102, 103, 105, 107, 113, 114, 115, 120, 121, 122, 123, 124, 125, 126, 132, 133, 134, 135, 136, 139, 140, 141, 142, 143, 145, 149, 150, 151, 152, 153, 154, 158, 160 , 164, 165, 166, 167, 170, 171, 173, 174, 177 , 179 , 180, 181, 182, 183, 184, 185, 189, 192, 193, 194, 241

[0149] Next, the effects of this composition and a composition containing the compound described in WO 2017 / 012965 against plant pathogens are shown in the following comparative test.

[0150] Comparative Test A comparative test was conducted using compounds No. 78 and No. 193 as the active ingredients of this composition, and compound D6-15 shown below as an active ingredient in a composition containing a compound described in WO 2017 / 012965. Preparation of drug solutions containing each compound: Each drug solution was prepared using each test compound in the same manner as above. This drug solution was used in Comparative Test Example 1 below. Comparative test example 1: Fungicidal effect test against tomato late blight (preventive effect test) Tomatoes (grown in vinyl pots with a diameter of 6 cm, at the 4.5-5.5 leaf stage) were sprayed with 10 mL of the solution using a spray gun. After the solution dried (on the day of treatment or the next day), a spore suspension of Phytophthora infestans was sprayed and inoculated, and the plants were placed in an inoculation box at a temperature of 20°C and a humidity of 95% or more for 16 hours. The plants were then placed in a thermostatic chamber at 20°C, and three days after inoculation, the lesion area rate was investigated, and the control rate was calculated using the same formula as in Test Example 1 above. The results are shown in Table 3. A means 100% control rate, B means 90-99% control rate, C means 70-89% control rate, D means 30-59% control rate, and E means 0-29% control rate.

[0151] [Table 23]

[0152] Next, formulation examples of the present composition will be described, but the blending ratios, dosage forms, etc. are not limited to the described examples. Formulation Example 1 (1) Compound of formula (I) 20 parts by weight (2) Clay 72 parts by weight (3) Sodium lignin sulfonate 8 parts by weight The above ingredients are mixed uniformly to prepare a wettable powder. Formulation Example 2 (1) Compound of formula (I) 5 parts by weight (2) Talc 95 parts by weight The above ingredients are mixed uniformly to make a powder. Formulation Example 3 (1) Compound of formula (I) 20 parts by weight (2) N,N'-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkyl phenyl ether 10 parts by weight (4) Xylene 50 parts by weight The above ingredients are mixed and dissolved uniformly to make an emulsion.

[0153] Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignosulfonate, 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Finely divided silica: 25 parts by weight The mixture of the above components is mixed with the compound of formula (I) in a weight ratio of 4:1 to give a wettable powder. Formulation Example 5 (1) Compound of formula (I) 50 parts by weight (2) Oxylated polyalkylphenyl phosphate -Triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight The above ingredients are mixed uniformly and crushed into a stock solution. (5) Sodium polycarboxylate 5 parts by weight (6) 42.8 parts by weight of anhydrous sodium sulfate The mixture is added, mixed uniformly, granulated, and dried to give a water dispersible granule. Formulation Example 6 (1) Compound of formula (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) 0.1 parts by weight of polyoxyethylene phosphate ester (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) are mixed uniformly in advance, diluted with an appropriate amount of acetone, sprayed onto (4), and the acetone is removed to obtain granules.

[0154] Formulation Example 7 (1) Compound of formula (I) 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight The above ingredients are mixed and dissolved uniformly to make an ultra low volume formulation. Formulation Example 8 (1) Compound of formula (I) 20 parts by weight (2) Oxylated polyalkylphenol phosphate -Triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 parts by weight (6) Water 72.7 parts by weight The above ingredients are mixed uniformly and pulverized to prepare an aqueous suspension.

Claims

1. Formula (I): 【Chemistry 1】 [In the formula, R １ is a halogen, R ２ is H or (C １ -C ３ )-alkyl; R ３ (C １ -C ３ )-alkyl, (C ３ -C ４ )-alkynyl, (C ２ -C ４ )-alkenyl, (C ３ -C ４ )-cycloalkyl, (C ２ -C ４ )-haloalkenyl, (C １ -C ３ )-alkyl, or H; R ２ and R ３ Together, R ２ and R ３ may form a 3- to 5-membered ring together with the nitrogen atom bonded to Z is cyano, halogen, (C １ -C ３ )-alkoxy, (C ３ )-cycloalkyl, or (C １ -C ３ )-alkylthio; R ４ is halogen, (C １ -C ３ )-alkyl, (C １ -C ３ )-haloalkyl, nitro, cyano, (C １ -C ３ )-alkylthio, (C １ -C ３ )-haloalkylthio, (C ２ -C ３ )-alkenyl, (C ２ -C ３ )-haloalkenyl, (C ３ -C ４ )-cycloalkyl, or (C １ -C ３ )-alkoxy, and n is an integer of 1 to 5], or a salt thereof.

2. Formula (I): 【Chemistry 2】 [In the formula, R １ is a halogen, R ２ is H or (C １ -C ３ )-alkyl; R ３ (C １ -C ３ )-alkyl, (C ３ -C ４ )-alkynyl, (C ２ -C ４ )-alkenyl, (C ３ -C ４ )-cycloalkyl, (C ２ -C ４ )-haloalkenyl, (C １ -C ３ )-alkyl, or H; R ２ and R ３ Together, R ２ and R ３ may form a 3- to 5-membered ring together with the nitrogen atom bonded to Z is cyano, halogen, (C １ -C ３ )-alkoxy, (C ３ )-cycloalkyl, or (C １ -C ３ )-alkylthio; R ４ is halogen, (C １ -C ３ )-alkyl, (C １ -C ３ )-haloalkyl, nitro, cyano, (C １ -C ３ )-alkylthio, (C １ -C ３ )-haloalkylthio, (C ２ -C ３ )-alkenyl, (C ２ -C ３ )-haloalkenyl, (C ３ -C ４ )-cycloalkyl, or (C １ -C ３ )-alkoxy, and n is an integer of 1 to 5], or a salt thereof to a plant body, a plant pathogen or soil.

3. Formula (IA): 【Chemistry 3】 [In the formula, R １Ａ is a fluorine, chlorine, or bromine atom, R ３Ａ is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl; R ４Ａ is halogen, (C １ -C ２ )-alkyl, (C １ )-haloalkyl, nitro, cyano, (C １ )-alkylthio, or (C １ )-haloalkylthio; and n is an integer of 1 to 5], or a salt thereof.

4. R ３Ａ The compound or salt thereof according to claim 3, wherein is methyl, ethyl, or propargyl.

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