JPS6325590B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel benzisothiazole compound, a method for producing the compound, and an agricultural fungicide containing the compound as an active ingredient. More specifically, the novel benzisothiazole compound of the present invention has the general formula: [ ^In _the formula ^, a furyl group, which may be
imidazolyl group, pyrazolyl group, or pyridyl group) or group -R ² (where R ² is a halogen atom or an alkyl group having 1 to 4 carbon atoms, mono, di,
Tri- or tetra-substituted imidazolyl group, thiazolinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, pyridine-N-oxide-yl group, 4(3H)
-pyrimidon-yl group, pyrimidyl group, thiazinyl group, or 1,2-benziisothiazole-
1,1-dioxide-3-yl group) is shown. ] It is expressed as . The compound of the above general formula () can be prepared by the method A below.
Furthermore, a compound in which X is a sulfur atom in the above general formula () can also be produced by method B below. That is, A general formula: (In the formula, Hal represents a halogen atom.) 3-halogeno-1,2-benzisothiazole-1,1-dioxide represented by the general formula: A-X-A () (wherein, M is hydrogen atom or alkali metal atom, X and A are the same as above. B General formula: (wherein M is the same as above) 3-mercapto-1,2-benziisothiazole-1,1-dioxide or an alkali metal salt thereof, and the general formula: Hal-A () (in the formula , Hal or A is the same as above.) General formula: (In the formula, A is the same as above.) A method for producing a benzisothiazole compound represented by the following. Furthermore, the present invention also relates to an agricultural fungicide containing a benzisothiazole compound represented by the above general formula () as an active ingredient. The present inventors have been conducting research for some time in order to search for compounds with high bactericidal activity. As a result, the present inventors discovered that among benzisothiazole compounds, in particular, a compound having a novel chemical structure represented by the above general formula () exhibits excellent biological activity as an agricultural fungicide. . On the other hand, prior to this application, Japanese Patent Application Publication No. 29297 of 1972 already contained the general formula: [However, R is −CH ₂ C≡Cl or

It is stated that the compound represented by the following formula has biological activity as a fungicide for fruit trees. However, the benzisothiazole compound represented by the above general formula () of the present invention has 1,
It is completely novel in terms of the specificity of the group substituted at the 3-position of the 2-benziisothiazole ring and the outstanding biological activity brought about thereby. 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. , shows remarkable effects on rice blast. 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, that is, they do not cause any phytotoxicity to cultivated plants at normal concentrations, so they can be used as agricultural and horticultural agents. It can be used quite advantageously against plant diseases caused by pathogenic bacteria. 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, it has surprising activity against the blast fungus (Pyricularia oryzae), which is an important pathogen of rice. The benzisothiazole compound represented by the general formula () of the present invention is synthesized by the following general method. That is, (In the formula, X, A, Hal and M are the same as above) In the above reaction formula, Halogen atoms, or methyl, ethyl, n-(or iso-)propyl, n-(or
mono-,
It represents a furfuryl group, an imidazolylmethyl group, a pyrazolylmethyl group, or a picolyl group, which may be di-, tri-, or tetra-substituted, or a mono- or , di-, tri-, or tetra-substituted imidazolyl group, thiazolinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, pyridine-N-oxide-yl group, 4
It represents a (3H)-pyrimidon-yl group, a pyrimidyl group, a thiazinyl group, or a 1,2-benziisothiazol-1,1-dioxide-3-yl group. Hal represents a halogen atom as described above. In addition, the general formula () shown in the above reaction formula
In the method for producing a compound, the raw material 3-halogeno-1,2-benziisothiazole-1,1-dioxide of general formula () is specifically 3-chloro-1,2-benzisothiazole-
Mention may be made of 1,1-dioxide. Further, the compounds of the general formula () which are raw materials at the same time are specifically 2-hydroxymethylfuran, (2-furyl)methanethiol, (1-pyrazolyl)methanethiol, 2,4,5-triprom-1 -Hydroxymethylimidazole, (3,5-dimethylpyrazol-1-yl)methanethiol, 3-hydroxymethylpyridine, 4-hydroxymethylpyridine, 2-mercapto-1-methylimidazole, 2-mercaptothiazoline, 2-mercaptobenzo Imidazole, 2-mercaptobenzoxazole, 6-chloro-2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-mercaptopyridine-N-oxide, 2-mercapto-4(3H)-pyrimidone, 2-mercaptopyrimidine, 2 -Mercapto-4,6,6-trimethyl-1,
Mention may be made of 3-thiazine, 3-mercapto-1,2-benziisothiazole-1,1-dioxide, and also their alkali metal salts. Next, the above manufacturing method will be specifically explained using representative examples. 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; esters such as ethyl acetate, amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethyl sulfoxide, sulfolane; and bases such as
Examples include 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. Further, the compound of the present invention in which X is a sulfur atom in the general formula () can also be synthesized by the following method. That is, (In the formula, A, Hal and M are the same as above) In the production method shown in the above reaction formula, 3-mercapto-1,2- of general formula () which is a raw material
Specifically, benzisothiazole-1,1-dioxide or its alkali metal salt is 3-mercapto-1,2-benzisothiazole-1,1
-dioxide, and also its alkali metal salts such as sodium and potassium. Further, the halogeno compounds of the general formula () that are raw materials are specifically 2-chloromethylfuran, 1-chloromethylpyrazole, 1-chloromethyl-3,5-dimethylpyrazole, 2-chloro-1-methylimidazole, 2 -Chlorthiazoline, 2-chlorobenzimidazole, 2-chlorobenzoxazole, 2,6-dichlorobenzoxazole, 2-chlorobenzothiazole, 2-chlorpyridine-N-oxide, 2-chlor-4(3H)-pyrimidone , 2-chloropyrimidine, 2-chloro-4,6,6-trimethyl-1,3
-thiazine, 3-chloro-1,2-benziisothiazole-
Mention may be made of 1,1-dioxide. Next, the above manufacturing method will be specifically explained using representative examples. In order to carry out the above method, the same solvent or diluent as mentioned above can be used, and the reaction can be carried out in the presence of the same acid binder as mentioned above. As before, this reaction 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 can be operated under increased pressure or reduced pressure. When the compound of the present invention is used as an agricultural fungicide, it can be used directly as it is after being diluted with water, or
Alternatively, it can be used in various formulations using methods commonly used in the agricultural chemical manufacturing field using agricultural aids. 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, propellants for aerosols, Mention may be made of 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 (eg, ethyl acetate, amyl acetate, etc.), amides (eg, dimethylformamide, dimethylacetamide, etc.), and sulfoxides (eg, dimethyl sulfoxide, etc.). Inorganic powder as a filler or carrier; 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, vermiculite,
Kaolinite, mica): vegetable granules; grain flour, starch, modified starch, sugar, glucose, crushed plant stems: synthetic resin granules; phenolic resins, urea resins, vinyl chloride resins. 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]: (Smoking action) Combustion regulator [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 fungicide of the present invention contains the active ingredient at 0.1
It can contain up 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: Can be carried out by soil application (e.g., mixing, sprinkling, vaporing, irrigation), etc. Also, the so-called ultra-high concentration small amount spraying method (ultra
-low-volume).
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 fungicidal composition comprising 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. It is well granulated and extrusion type granulator is used to make 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 having 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. 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 present invention can be seen from the following test results against rice blast fungi. Test Example 1 Preparation of test compound for foliar spray efficacy test against rice blast disease Active compound: 50 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1:5)
45 parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkyl phenyl ether The above-mentioned amounts of the active compound, carrier and emulsifier are ground and mixed to form a wettable powder, which is prepared by diluting the predetermined amount with water. Test method Paddy rice (variety: Asahi) was grown in clay pots with a diameter of 12 cm, and at the 3rd to 4th leaf stage, 50 ml of a diluted solution of the test compound prepared as described above at a predetermined concentration was sprayed per 3 pots. The next day, a suspension of artificially cultured rice blast fungus spores was spray-inoculated (twice) and kept in a humid room at 25°C and 100% relative humidity to allow infection. Seven days after inoculation, the degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. At the same time, drug damage was also investigated. Morbidity Spot area percentage (%) 0 0 0.5 2 or less 1 3-5 2 6-10 3 11-20 4 21-40 5 41 or more Control value (%) = (Mobility in untreated area - treated area Morbidity level / Morbidity level in untreated area) x 100 This test is the result of 3 pots in 1 area. The results are shown in Table 1.

【table】

[Table] Test Example 2 Test method for testing the effectiveness of water surface application against rice blast Using a pipette, the chemical solution was irrigated onto the water surface at the indicated amount without directly touching the above-ground parts of the rice plants. Five days later, a suspension of rice blast fungus spores was spray inoculated by a conventional method and kept in an inoculation chamber at a temperature of 23 to 25°C and a relative humidity of 100% for 24 hours. Thereafter, the plants were transferred to a glass greenhouse at a temperature of 20 to 28°C, and 7 days after inoculation, the same investigation as in Test Example 1 was conducted to determine the control value (%). At the same time, drug damage was also investigated. The results are shown in Table 2.

【table】

[Table] and B are the same as Table 1.
Next, a synthesis example will be shown and a method for producing the compound of the present invention will be specifically described. Synthesis example 1 Dissolve 1.09 g of 3-hydroxymethylpyridine in 20 ml of toluene, add 1.01 g of triethylamine, and stir. Next, add 3-chloro-1,
2-Benzisothiazole-1,1-dioxide
Add 2.02g and stir at room temperature overnight. After the reaction is complete, water is added to dissolve triethylamine hydrochloride, and precipitated crystals that are insoluble in water and toluene are sucked off. When this crystal is washed with methyl alcohol, the target product 3-(3'-picolyloxy)-1,2
-Benzisothiazole-1,1-dioxide
2.2g is obtained. mp146～148℃ Synthesis example 2 After dissolving 0.23 g of sodium metal in 20 ml of ethanol and then dissolving 1.19 g of 2-mercaptothiazoline, the ethanol is distilled off under reduced pressure. At this time, toluene is added to completely remove ethanol and when the mixture is azeotroped with ethanol, 2-mercaptothiazoline sodium salt is obtained. This was suspended in 10 ml of acetonitrile, and 3-chloro-1,
2-Benzisothiazole-1,1-dioxide
Add 2.02g and stir at room temperature overnight. After the reaction, acetonitrile was distilled off under reduced pressure, and water and
Add 10% Na ₂ CO ₃ aqueous solution, stir well, and suck off the precipitated crystals. Furthermore, this crystal,
After washing with water until the washing solution becomes neutral and drying in a desiccator, the target product 3-(2'-thiazolinylthio)-1,2-benziisothiazole-1,1
-2.58 g of dioxide are obtained. mp202～207℃ Synthesis example 3 2.01 g of 3-mercapto-1,2-benziisothiazole-1,1-dioxide, 1.17 g of 1-chloromethylpyrazole, and 1.38 g of potassium carbonate were suspended in 30 ml of methyl ethyl ketone, and the mixture was heated at 40 to 50°C.
Stir on a water bath for 3 hours. After stirring, the precipitated crystals are removed, the liquid is concentrated under reduced pressure, and the resulting crystals are washed with ethanol to obtain the desired product, 3-
2.23 g of (1'-pyrazolylmethylthio)-1,2-benziisothiazole-1,1-dioxide are obtained. mp160-163°C Table 3 shows the compounds of the present invention synthesized by substantially the same method as above.

【table】

[Table] The present invention, which has been explained in detail in the detailed description of the invention, is specifically summarized as follows. 1 General formula: [In the formula, X is an oxygen atom or a _sulfur atom; ^A is a group ^; a furyl group, an imidazolyl group, a pyrazolyl group, or a pyridyl group which may be substituted) or a group, -R ² , (where R ² is a halogen atom or an alkyl group having 1 to 4 carbon atoms, , di-, tri-, or tetra-substituted imidazolyl group, thiazolinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, pyridine-N-oxide-yl group, 4(3H)-pyrimidon-yl group, pyrimidyl group group, thiazinyl group, or 1,2-benziisothiazol-1,1-dioxide-3-yl group). ] A benzisothiazole compound represented by 2 General formula: (In the formula, Hal represents a halogen atom.) 3-halogeno-1,2-benziisothiazole-1,1-dioxide represented by the general formula: M-X-A () (wherein, M is hydrogen atom or alkali metal atom, X and A are the same as above. 3 General formula: (In the formula, M is the same as above) 3-mercapto-1,2-benziisothiazole-1,1-dioxide or an alkali metal salt thereof, and the general formula: Hal-A () (in the formula , Hal or A is the same as above.) General formula: (In the formula, A is the same as above.) A method for producing a benzisothiazole compound represented by the following. 4. An agricultural fungicide characterized by containing a benzisothiazole compound represented by the general formula () as an active ingredient. 5. A method for controlling plant diseases, which comprises applying a benzisothiazole compound represented by the general formula () to plant pathogenic bacteria and/or their growth sites. 6. Use of the benzisothiazole compound represented by the above general formula () for controlling plant pathogenic bacteria. 7. An agricultural fungicidal composition characterized in that the benzisothiazole compound represented by the general formula () is mixed with a diluent (solvent and/or filler and/or carrier) and/or surfactant. manufacturing method.

Claims (1)

[Claims] 1. General formula: [ ^In _the formula ^, a furyl group, an imidazolyl group, a pyrazolyl group, or a pyridyl group which may be tetra-substituted) or a group -R ² (here, R ² is a halogen atom or an alkyl group having 1 to 4 carbon atoms, so that mono-, di- ,
Tri- or tetra-substituted imidazolyl group, thiazolinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, pyridine-N-oxide-yl group, 4(3H)
-pyrimidon-yl group, pyrimidyl group, thiazinyl group, or 1,2-benziisothiazole-
1,1-dioxide-3-yl group) is shown. ] A benzisothiazole compound represented by 2 formula: 3- of claim 1, which is indicated by
(4'-picolyloxy)1,2-benziisothiazole-1,1-dioxide. 3 formula: 3- of claim 1, which is indicated by
(2'-Thiazolinylthio)-1,2-benziisothiazole-1,1 dioxide. 4 formula: 3-(pyridine-N-oxide-2'-ylthio)-1,2 according to claim 1, which is represented by
-Benzisothiazole-1,1-dioxide. 5 Formula: 3- of claim 1, which is indicated by
(4′(3′H)pyrimidon-2′-ylthio)-1,2-
Benziisothiazole-1,1-dioxide. 6 Formula: 3- of claim 1, which is indicated by
(2'-Benzoxazolylthio)-1,2-benzisothiazole-1,1-dioxide. 7 General formula: (In the formula, Hal represents a halogen atom) 3-halogeno-1,2-benziisothiazole-1,1-dioxide represented by the general formula: M-X-A [wherein M is a hydrogen atom or an alkali ^metal atom; X is an oxygen atom or a sulfur atom; A is a layer _-CH2 - ^R1 ; a furyl group, an imidazolyl group, a pyrazolyl group, or a pyridyl group which may be tetra-substituted) or a group -R ² (here, R ² is a halogen atom, or an alkyl group having 1 to 4 carbon atoms, mono, di, an imidazolyl group, a thiazolinyl group, a benzimidazolyl group, which may be tri- or tetra-substituted;
Benzoxazolyl group, benzothiazolyl group, pyridine-N-oxidoyl group, 4(3H)-pyrimidon-yl group, pyrimidyl group, thiazinyl group,
or 1,2-benziisothiazole-1,1-
Dioxide-3-yl group) is shown. ] A general formula characterized by reacting with a compound represented by: (In the formula, X and A are the same as above.) A method for producing a benzisothiazole compound represented by the following. 8 General formula: (In the formula, M represents a hydrogen atom or an alkali metal atom.) 3-mercapto-1,2-benzisothiazole-1,1-dioxide or its alkali metal salt represented by the general formula: Hal-A [ In the formula, Hal is a halogen atom, A is a group -CH ₂ -R ¹ (where R ¹ may be mono-, di-, tri-, or tetra-substituted by a halogen atom or an alkyl group having 1 to 4 carbon atoms) frill group,
imidazolyl group, pyrazolyl group, or pyridyl group) or group -R ² (here, R ² is a halogen atom or an alkyl group having 1 to 4 carbon atoms, mono, di,
Tri- or tetra-substituted imidazolyl group, thiazolinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, pyridine-N-oxide-yl group, 4(3H)
-pyrimidon-yl group, pyrimidyl group, thiazinyl group, or 1,2-benziisothiazole-
1,1-dioxide-3-yl group) is shown. ] A general formula characterized by reacting with a halogeno compound represented by: (In the formula, A is the same as above.) A method for producing a benzisothiazole compound represented by the following. 9 General formula: [ ^In _the formula ^, an optionally substituted furyl group,
imidazolyl group, pyrazolyl group or pyridyl group) or group -R ² (where R ² is a halogen atom or an alkyl group having 1 to 4 carbon atoms, mono, di,
Tri- or tetra-substituted imidazolyl group, thiazolinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, pyridine-N-oxide-yl group, 4(3H)
-pyrimidon-yl group, pyrimidyl group, thiazinyl group, or 1,2-benziisothiazole-
1,1-dioxide-3-yl group) is shown. ] An agricultural fungicide containing a benzisothiazole compound represented by the following as an active ingredient.