JPS6350350B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention provides acyl-pyridylthiourea derivatives,
The present invention relates to a method for producing the compound and an agricultural and horticultural fungicide containing the compound as an active ingredient. More specifically, the acyl-pyridylthiourea derivatives of the present invention have the general formula: [wherein R is an alkyl group having 1 to 8 carbon atoms, a halogenoalkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aralkyl group,
(In some cases, the aralkenyl group has 1 carbon atom
an aryl group which may be mono- or di-substituted by ~4 alkyl groups, halogen atoms, or alkoxy groups having 1 to 4 carbon atoms, or may be substituted by methylenedioxy groups; (In some cases, the aryl group is an alkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, an alkoxy group having 1 to 4 carbon atoms, a phenoxy group, an acyloxy group having 1 to 4 carbon atoms, or an acyloxy group having 1 to 4 carbon atoms. alkoxy having 1 to 8 carbon atoms, which may be mono-, di-, or tri-substituted by 1 to 4 halogenoacyloxy groups, or substituted by methylenedioxy groups; group, a halogenoalkoxy group having 1 to 8 carbon atoms, an alkenyl group substituted by a 5- to 7-membered heterocyclic group containing an oxygen atom, a sulfur atom, and/or a nitrogen atom as a heteroatom, or a hetero a 5- to 7-membered heterocyclic group containing an oxygen atom, a sulfur atom, and/or a nitrogen atom; X represents a halogen atom; ] It is expressed as . The compound of the above general formula () is, for example, the following:
It can be produced by methods (A) and (B), and the present invention also relates to these production methods. That is, (A) General formula: [In the formula, R is the same as above. ] Isothiocyanate represented by the general formula: [In the formula, X is the same as above. ] A method for producing an acyl-pyridylthiourea derivative represented by the general formula (), which comprises reacting with 2-amino-5-halogenopyridine represented by the formula (). (B) Potassium thiocyanate and general formula: [In the formula, R is the same as above. Hal indicates a halogen atom. ] is reacted with an acyl halide represented by the following, and then the general formula: [In the formula, X is the same as above. ] A method for producing an acyl-pyridylthiourea derivative represented by the general formula (), which comprises reacting a 2-amino-5-halogenopyridine represented by the formula (). Furthermore, the present invention relates to an agricultural and horticultural fungicide containing an acyl-pyridylthiourea derivative represented by the general formula () as an active ingredient. The present inventors have conducted extensive research in order to create new compounds with bactericidal activity. It was discovered that it has excellent bactericidal activity. The fungicidally active compounds of the present invention are particularly characterized by their chemical structure. That is, as shown in the general formula (), when the nitrogen atom of thiourea is substituted with a 5-halogeno-2-pyridyl group and the other nitrogen atom is substituted with an acyl group, extremely excellent bactericidal activity is achieved. has. The compounds of the present invention mainly have this basic skeleton, and compounds having this basic skeleton uniformly have excellent bactericidal activity. On the other hand, in the Japanese Patent Application Publication No. 18255 of 1975, which was already publicly known before this application, the general formula: (In the formula, A is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group; B is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group; however, A and B cannot both represent a hydrogen atom at the same time; and Y is an oxygen atom or a sulfur atom, R is a hydrogen atom, an alkyl group or an alkoxymethyl group, _R1 is a hydrogen atom, an alkyl group that may be substituted with cyano, a 1-cycloalkenyl group, a benzyl group, a hydroxyl group, an acetyl group. group or alkoxycarbonyl group, where R and R ₁ are shown in the above formula

[Formula] Together with the group, a ring of parabanic acid, hydantoin or tetrahydroxadiazinone can be formed, and R ₂ is a pyridyl group, a phenyl group, or a halogen, cyano, nitro, alkyl, which can be substituted with a halogen. Cycloalkyl, halogen-substituted cycloalkyl, alkylthio, alkoxy, alkylthioalkyl, trifluoromethyl, alkylsulfonyl, dialkylaminosulfonyl, phenyl, benzyl, phenylthio, halogen-substituted phenoxy, acetyl, phenylcarbonyl, or ring with tetramethylene or dioxymethylene It has been described that a compound represented by the following formula (indicating a phenyl group substituted to form a phenyl group) has insecticidal activity. However, the acyl-pyridylthiourea derivative of the present invention represented by the general formula () has the following characteristics compared to the compound represented by the general formula ():
It is completely novel in terms of the specificity of its chemical structure and the outstanding bactericidal activity elicited by it. The compound represented by the above general formula () of the present invention has excellent bactericidal and growth-inhibiting power against plant pathogenic bacteria, and can be applied to exterminate and eradicate plant diseases caused by a wide variety of fungi. It shows remarkable effects on plant diseases caused by bacteria, such as rice leaf blight. The active compounds of the invention can be used against pathogens that parasitize the above-ground parts of plants, pathogens that invade plants from the soil and cause tracheomycosis, seed-borne pathogens, and soil-borne pathogens. In addition, these compounds have low toxicity to warm-blooded animals and good affinity for higher plants, which means that they do not harm cultivated plants at normal concentrations, so they are used as agricultural and horticultural agents to treat pathogenic bacteria. It can be used quite advantageously against plant diseases caused by. That is, as fungicides, archaeal bacteria (Archimycetes), algae (Phycomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes), and Deuteromycota (Fungi fungi) are used as fungicides. It can be effectively used against various plant diseases caused by Fungi Imperfecti and other bacteria. In particular, we focus on bacterial leaf blight [Xanthomonas oryzae], which is an important disease of rice, and bacterial spot disease [Xanthomonas vesicatoria] on various crops.
vesicatoria)]. Due to the above-mentioned excellent fungicidal properties, the active compounds of the present invention are effective against diseases caused by plant pathogens, which conventionally had to be controlled with fungicides containing arsenic and mercury, which are heavy metals harmful to humans and animals. can be used with good results. The acyl-pyridylthiourea derivative represented by the general formula () of the present invention is synthesized by the following general method. That is, [In the formula, R, X and Hal are the same as above. ] In the above reaction formula, R is specifically an aralkenyl group such as a styryl group or a cinnamyl group, or optionally a monomer group formed by an alkyl group having 1 to 4 carbon atoms as described above, a halogen atom, or a phenyl group. -, di-, or tri-substituted phenoxymethyl group, 1-
Aryloxyalkyl groups such as phenoxyethyl group, 1-(p-phenylphenoxy)ethyl group,
an alkoxy group having 1 to 8 carbon atoms as described above,
Vinyl groups, propenyl groups, etc. substituted with heterocyclic groups such as halogenoalkoxy groups, pyrrolidyl, furyl, imidazolyl, oxazolyl, thiazolyl, thienyl, pyridyl, pyrimidyl, piperidino, piperidyl, pyrazyl, piperazyl, morpholinyl, morpholino, etc. an alkenyl group or a heterocyclic group as described above; X represents a halogen atom as described above; In addition, in the method for producing the compound of the general formula () shown in the above reaction formula example, the acyl halide represented by the general formula () as a raw material is specifically cinnamoyl chloride, p-isopropylcinnamoyl chloride, 2,4-dichlorcinnamoyl chloride, 3,4-dichlorcinnamoyl chloride, 2,6-dichlorcinnamoyl chloride, m-methoxycinnamoyl chloride, 3,4-dimethoxycinnamoyl chloride, 3,4-dichlorcinnamoyl chloride Methylenedioxycinnamoyl chloride, phenoxyacetyl chloride, 2-p
-tert-Butylphenoxypropionyl chloride, 2-p-biphenyloxypropionyl chloride, 2-p-bromophenoxypropionyl chloride, 2-(2',4',5'-trichlorophenoxy)propionyl chloride , 2−(2′,6′−
dichlorophenoxy)propionyl chloride,
Ethyl chloroformate, butyl chloroformate, isobutyl chloroformate, amyl chloroformate, 2,2,2-trichloroethyl chloroformate, 3-(2-furyl)-acryloyl chloride, 3-(2-thienyl) -acryloyl chloride, 2-furoyl chloride, 2-thiophene-carbonyl chloride, nicotinoyl chloride and the like. Moreover, bromide can also be mentioned instead of these chlorides. The isothiocyanate represented by the general formula (), which is both a raw material and a production intermediate, specifically includes cinnamoyl, p-isopropylcinnamoyl, 2,4-dichlorocinnamoyl,
3,4-dichlorcinnamoyl-, 2,6-dichlorcinnamoyl-, m-methoxycinnamoyl-, 3,4-dimethoxycinnamoyl-, 3,4
-methylenedioxycinnamoyl-, ethoxycarbonyl-, butoxycarbonyl-, isobutoxycarbonyl-, amyloxycarbonyl-, 2,
2,2-trichloroethoxycarbonyl-,3-
(2-furyl)-acryloyl-, 3-(2-thienyl)-acryloyl-, 2-furoyl-, 2-
Examples include isothiocyanates such as thiophenecarbonyl and nicotinoyl. Furthermore, specific examples of the raw material 2-amino-5-halogenopyridine represented by the general formula () include 2-amino-5-chloropyridine, 2-amino-5-bromo-pyridine, etc. can. Next, the above manufacturing method will be specifically explained using representative examples. In the above reaction formula, the isothiocyanate obtained as a production intermediate can be isolated, but the reaction is continued without isolation and reacted with 2-amino-5-halogenopyridine to form the desired acyl-pyridyl - Thiourea derivatives can be obtained with high purity and high yield. The method of the invention is preferably carried out using a solvent or diluent. All inert solvents and diluents can be used for this purpose. Such solvents or diluents include water; aliphatic cycloaliphatic and aromatic hydrocarbons (which may optionally be chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene. , methylene chloride,
Chloroform, carbon tetrachloride, ethylene chloride and tri-chloroethylene, chlorobenzene;
Other ethers such as diethyl ether,
Methyl ethyl ether, di-iso-propyl ether, dibutyl ether, propylene oxide dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl-iso
-propyl ketone, methyl-iso-butyl ketone; nitriles such as acetonitrile, propionitrile, acrylonitrile; alcohols such as methanol, ethanol, iso-propanol, butanol, ethylene glycol; esters such as ethyl acetate, amyl acetate; acids Amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethylsulfoxide, sulfolane; and bases such as pyridine. Furthermore, as described above, the reaction of the present invention can be carried out in the presence of an acid binder. Such acid binders include commonly used alkali metal hydroxides, carbonates, bicarbonates, alcoholates, etc., and tertiary amines such as triethylamine, diethylaniline, pyridine, etc. . The method of the invention can be carried out within a wide temperature range. It is generally carried out between -20°C and the boiling point of the mixture, preferably between 0 and 100°C. Further, although the reaction is preferably carried out under normal pressure, it is also possible to operate under increased pressure or reduced pressure. When the compound of the present invention is used as a fungicide for agriculture and horticulture, it can be used as it is by diluting it directly with water, or it can be prepared in various formulations using a method commonly used in the agricultural chemical manufacturing field using an agricultural chemical auxiliary. It can be used as In actual use, these various formulations can be used directly or diluted with water to a desired concentration. Examples of pesticide adjuvants mentioned here include diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, dispersants, wetting agents), stabilizers, fixing agents, and propellants for aerosols. , synergists. Solvents include water: organic solvent; hydrocarbons [e.g., n-hexane, petroleum ether, naphtha, petroleum fractions (paraffin wax, kerosene, light oil, medium oil, heavy oil), benzene, toluene, xylenes], halogenated Hydrocarbons [e.g. chlormethylene, carbon tetrachloride, trichlorethylene, ethylene chloride, ethylene dibromide, chlorobenzene chloroform], alcohols [e.g. methyl alcohol, ethyl alcohol, propyl alcohol, ethylene glycol], ethers , [e.g. ethyl ether, ethylene oxide, dioxane],
Alcohol ethers, [e.g., ethylene glycol monomethyl ether, etc.], ketones, [e.g., acetone, isophorone, etc.], esters, [e.g., ethyl acetate, amyl acetate, etc.], amides, [e.g., dimethylformamide, dimethylacetamide, etc.] ], sulfoxides, [for example, dimethyl sulfoxide, etc.]. Inorganic granules as fillers or carriers; sulfur, slaked lime, magnesium lime, gypsum, calcium carbonate, silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite,
Clay minerals (e.g. pyrophyllite, talc, montmorillonite, beidellite, permiculite, kaolinite, mica): vegetable powder; grain flour;
Starch, modified starch, sugar, glucose, dried crushed plant stems: synthetic resin powder; phenolic resin, urea resin, vinyl chloride resin. Examples of surfactants include anionic surfactants; alkyl sulfates, [e.g., sodium lauryl sulfate, etc.], arylsulfonic acids, [e.g., alkylarylsulfonates, sodium alkylnaphthalenesulfonates], and succinates. , polyethylene glycol alkylaryl ether sulfate salts: cationic surfactants; alkylamines, [e.g.
laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, etc.], polyoxyethylene alkylamines: nonionic surfactants; polyoxyethylene glycol ethers, [e.g., polyoxyethylene alkylaryl ether, and condensates thereof ], polyoxyethylene glycol esters, [eg, polyoxyethylene fatty acid ester], polyhydric alcohol esters, [eg, polyoxyethylene sorbitan monolaurate], amphoteric surfactants, and the like. In addition, stabilizers, fixing agents [e.g., agricultural soap, caseinate lime, sodium alginate, polyvinyl alcohol (PVA), vinyl acetate adhesives, acrylic adhesives], propellants for aerosols [e.g.
Trichlorofluoromethane, dichlorofluoromethane, 1,2,2-trichloro-1,1,2-trifluoroethane, chlorobenzene, LNG, lower ether]: Combustion regulator (for smoking agents) [e.g.
Nitrite, zinc powder, dicyandiamide]: oxygen yielding agent [e.g. chlorate,
Dichromate]: Phytotoxicity reducer [e.g. sulfuric acid, zinc, ferrous chloride, copper nitrate]: Efficacy extender: Dispersion stabilizer [e.g. casein, tragacanth, carboxymethyl cellulose (CMC), polyvinyl alcohol (PVA)] ]: Examples include synergists. The compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Forms of preparations include emulsions, oils, wettable powders, aqueous solutions, suspensions, powders, granules, powders, smoking agents, tablets, aerosols, pastes, capsules, etc. can. The agricultural and horticultural fungicide of the present invention contains the above-mentioned active ingredient.
It can be contained in an amount of 0.1 to 95% by weight, preferably 0.5 to 90% by weight. In actual use, the various formulations and spray preparations described above (ready-to-use)
The active compound content in the preparation is generally
0.0001-20% by weight, preferably 0.005-10% by weight
A range of is appropriate. The content of these active ingredients can be changed as appropriate depending on the form of the preparation, the method of application, purpose, timing, location, and occurrence of plant diseases. The compound of the present invention may also be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant growth regulators, attractants [e.g. Organic phosphoric acid ester compounds, carbamate compounds, dithio (or thiol)
Carbamate compounds, organic chlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, urea compounds, triazine compounds] or/and fertilizers can also be present. Various formulations or ready-to-use preparations containing the active ingredients of the invention are available.
Preparation) refers to the application methods commonly used in the field of agrochemical manufacturing, such as spraying, misting, atomizing, dusting, powdering, water surface application, and pouring. ]: Fumigation: by soil application, [e.g., mixing, sprinkling, vaporing, irrigation]: surface application, [e.g., spreading, banding, dressing, covering]: by dipping), etc. can be done. It can also be used by what is called an ultra-low-volume spraying method. In this way it is possible to have 100% active ingredient content. The application rate per unit area is approximately 0.03 to 10 Kg of active compound per hectare, preferably 0.3 to 10 Kg of active compound per hectare.
6Kg is used. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges. The present invention comprises a compound of the general formula () as an active ingredient, and further contains a diluent (solvent and/or filler and/or carrier) and/or surfactant, and if necessary, a stabilizer, a fixing agent, etc. An agricultural and horticultural fungicidal composition containing a synergist is provided. Furthermore, the present invention provides a method for applying the compound of the general formula () alone to plant pathogenic bacteria and/or their locations,
or a diluent (solvent and/or filler and/or carrier) and/or surfactant, and if necessary, a method for controlling plant diseases, which is applied in combination with, for example, a stabilizer, a fixing agent, a synergist. Ru. EXAMPLES Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 (Wettable powder) Compound No. 1 of the present invention, 15 parts, mixture of powdered diatomaceous earth and powdered clay (1:5), 80 parts, sodium alkylbenzenesulfonate, 2 parts, sodium alkylnaphthalenesulfonate formalin condensation thing,
Three parts were ground and mixed to form a wettable powder. This is diluted with water and sprayed onto plant pathogens and/or their growth areas. Example 2 (Emulsion) Compound No. 2 of the present invention, 15 parts, methyl ethyl ketone
70 parts of polyoxyethylene alkyl phenyl ether, 8 parts of calcium alkylbenzenesulfonate, and 7 parts of calcium alkylbenzenesulfonate were mixed and stirred to prepare an emulsion. This is diluted with water and sprayed onto plant pathogens and/or their growth areas. Example 3 (Powder) 2 parts of Compound No. 3 of the present invention and 98 parts of powdered clay were pulverized and mixed to prepare a powder. This is sprinkled on plant pathogens and/or their growth areas. Example 4 (Powder) 1.5 parts of Compound No. 4 of the present invention, 0.5 parts of isopropyl hydrogen phosphite (PAP), and 98 parts of powdered clay were ground and mixed to make a powder, and the powder was sprinkled on plant pathogenic bacteria and/or their growth areas. do. Example 5 (Granules) To a mixture of 10 parts of the present compound No. 5, 30 parts of bentonite (montmorillonite), 58 parts of talc, and 2 parts of lignin sulfonate, 25 parts of water was added. By using an extrusion type granulator, 10
Form into granules of ~40 mesh and dry at 40-50°C to make granules. This is sprinkled on plant pathogens and/or their growth areas. Example 6 (Granules) Clay mineral particles with a particle size distribution of 0.2 to 2 mm, 95
5 parts of Compound No. 6 of the present invention dissolved in an organic solvent are sprayed onto the mixture in a rotary mixer, and 5 parts of the compound No. 6 and 5 parts dissolved in an organic solvent are sprayed thereon and dried at 40 to 50°C to form granules. This is sprinkled on plant pathogens and/or their growth areas. Example 7 (Oil agent) 0.5 parts of compound No. 7 of the present invention and 99.5 parts of kerosene are mixed and stirred to prepare an oil agent. This is combined with plant pathogens and/or
Or spray the areas where they grow. When compared with active compounds of similar structure and compounds of similar active form already known from the literature, the novel compounds according to the invention demonstrate a substantially improved efficacy and a very high toxicity for warm-blooded animals. This compound is characterized by a low oxidation rate, and therefore has very high utility value. The unexpected superiority and remarkable efficacy of the active compounds of the invention can be seen from the results of the following tests in which they were used against bacterial leaf blight of rice and bacterial spot of cucumber. Test example 1 Leaf spray test test method for rice leaf blight In a glass greenhouse, a liquid medium was preliminarily applied to the center of the leaf blade of paddy rice (variety: Kinnanfeng) at the highest tillering stage, which was submerged in ^{a 0.01} m 2 white porcelain pot. A bacterial suspension of rice bacterial leaf blight that had been cultured for 2 days was inoculated with a needle, and 3 hours after the inoculation, a diluted solution of the test compound at a predetermined concentration prepared in the same manner as in Example 1 was added to 50 ml/3 pots. It was distributed at a rate of After air-drying the sprayed chemical solution, test plants were dried for 28~
The animals were transferred to a controlled greenhouse at 32°C and humidity of 60-90%, and after 10 days of normal management, the disease state was investigated. The disease severity of 20 inoculated leaves per pot was graded from 0 to 5 according to the following criteria, and the degree of damage was calculated according to the following formula to determine the control value. The results are shown in Table 1. Disease severity n ₀ ...No disease n ₁ ...Number of leaves with a lesion area ratio of 10% or less n ₂ ...Number of leaves with a lesion area ratio of 11 to 20% n ₃ ...Spot area ratio 21 to 20% Number of leaves at 30% n ₄ ... Number of leaves with a lesion area ratio of 31 to 50% n ₅ ... Number of leaves with a lesion area ratio of 50% or more Damage degree = 5n ₅ +4n ₄ +3n ₃ +2n ₂ +n ₁ / 5N×100 (N: total number of leaves surveyed (20 leaves/pot) Control value = degree of damage in untreated area – degree of damage in treated area / degree of damage in untreated area ×100

[Table] Test Example 2 Water surface application test against rice leaf blight 0.05% of the test compound prepared in the same manner as in Test Example 1 at the highest tillering stage of paddy rice (variety: Kinnanfu) grown under water in the same manner as in Test Example 1. The diluted solution was irrigated into water at a rate of 10 ml/pot so as not to directly contact the above-ground parts of the rice body. Four days after irrigation, a bacterial suspension of bacterial leaf blight prepared in the same manner as in Test Example 1 was inoculated with a needle, and after inoculation, the disease onset was waited for under the same conditions as in Test Example 1, and the disease state was investigated. The results are shown in Table 2.

[Table] Test Example 3 Seed disinfection test against cucumber bacterial spot disease Cucumber seeds (variety: Yotsuba) were soaked in a suspension of pathogenic bacteria obtained by artificial culture for 1 hour to infect them with pathogenic bacteria, and then air-dried indoors. After that, it was tested for efficacy. Cucumber seeds infected with pathogenic bacteria were immersed in a diluted solution of a test compound at a predetermined concentration prepared in the same manner as in Test Example 1, and after being left at room temperature for 1 hour, the seeds were taken out and the excess chemical solution was adsorbed and removed on paper. From, diameter
Seeds were sown in field soil prepared in 12 cm flower pots, and germinated under normal management in a glass greenhouse. We investigated the occurrence of lesions on the primary leaves of cucumber that developed 10 days after sowing.
The control value of the test compound was determined from the disease attack rate. The results are shown in Table 3. Control value = Infection rate in untreated area - Incidence rate in treated area / Infection rate in untreated area × 100

[Table] Next, a synthesis example will be shown and the method for producing the compound of the present invention will be specifically described. Synthesis example 1 12.6 g of potassium thiocyanate, 250 g of acetone
ml, and a solution of 16.2 g of nicotinoyl chloride dissolved in 80 ml of acetone is added dropwise to this solution in the same manner as in Synthesis Example 1 to obtain an acetone solution of nicotinoyl isothiocyanate. Next, 2-
12.8g of amino-5-chloropyridine in acetone
In the same manner as in Synthesis Example 1, the acetone solution of nicotinoyl isothiocyanate obtained earlier was added dropwise to this solution, and the same process as in Synthesis Example 1 was performed to obtain the target N-5-chloro 27.1 g of -2-pyridyl-N'-nicotinoylthiourea are obtained. mp212-214°C Compounds synthesized by substantially the same method as above are shown in Table 4.

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Claims (1)

[Claims] 1. General formula: [In the formula, R is an aralkenyl group (in some cases, the aralkenyl group is an alkyl group having 1 to 4 carbon atoms,
an aryloxyalkyl group (optionally) which may be mono- or di-substituted by a halogen atom or an alkoxy group having 1 to 4 carbon atoms, or substituted by a methylenedioxy group; , the aryloxyalkyl group may be mono-, di-, or tri-substituted by an alkyl group having 1 to 4 carbon atoms, a halogen atom, or a phenyl group) alkoxy having 1 to 8 carbon atoms group, a halogenoalkoxy group having 1 to 8 carbon atoms, an alkenyl group substituted by a 5- to 7-membered heterocyclic group containing an oxygen atom, a sulfur atom, and/or a nitrogen atom as a heteroatom, or a hetero An acyl-pyridylthiourea derivative represented by a 5- to 7-membered heterocyclic group containing an oxygen atom, a sulfur atom, and/or a nitrogen atom, X represents a halogen atom. 2 formula: N-5- according to claim 1 indicated by
Chlor-2-pyridyl-N'-cinnamoylthiourea. 3 formula: N-5- according to claim 1 indicated by
Chlor-2-pyridyl-N'-nicotinoylthiourea. 4 General formula: [In the formula, R is an aralkenyl group (in some cases, the aralkenyl group is an alkyl group having 1 to 4 carbon atoms,
an aryloxyalkyl group (optionally) which may be mono- or di-substituted by a halogen atom or an alkoxy group having 1 to 4 carbon atoms, or substituted by a methylenedioxy group; , the aryloxyalkyl group may be mono-, di-, or tri-substituted by an alkyl group having 1 to 4 carbon atoms, a halogen atom, or a phenyl group) alkoxy having 1 to 8 carbon atoms group, a halogenoalkoxy group having 1 to 8 carbon atoms, an alkenyl group substituted by a 5- to 7-membered heterocyclic group containing an oxygen atom, a sulfur atom, and/or a nitrogen atom as a heteroatom, or a hetero A 5- to 7-membered heterocyclic group containing an oxygen atom, a sulfur atom, and/or a nitrogen atom as an atom, X represents a halogen atom. Fungicide.