JP5675181B2 - Bis (benzoisothiazole) derivative and method for producing the same, and bactericidal agent containing the same - Google Patents

Description

  The present invention relates to a novel benzoisothiazole derivative and a production method and use thereof. More specifically, the present invention relates to a bis (benzoisothiazole) derivative, a method for producing the derivative, and a fungicide containing the derivative as an active ingredient.

  Various characteristics have been conventionally required for fungicides used in the agricultural field. Examples of the characteristics required for the bactericidal agent include sustainability of effect, broad spectrum, safety during use, ease of use in combination with other drugs and formulation auxiliary materials, and the like. Of course, the price is required to be low.

  Conventionally, bactericidal compounds having a benzoisothiazole structure are known (see Patent Documents 1 to 4).

JP-A-48-22627 JP 58-21672 A Japanese Examined Patent Publication No. 45-14301 Japanese Patent Publication No. 45-38080

  In the fungicides used in the agricultural field, the emergence of resistant bacteria having drug resistance due to long-term use of specific drugs has become a problem. In order to prevent the emergence of resistant bacteria and to eliminate the emerged resistant bacteria, there is still a need for the development of new fungicides having the various characteristics described above.

  As the bactericidal compound having a benzoisothiazole structure, synthesis examples disclosed in Patent Documents 1 to 4 are known. However, a compound having a structure such as the novel bis (benzoisothiazole) derivative according to the present invention has not been reported, and the usefulness of such a compound has not been reported.

  Therefore, the main object of the present invention is to provide a novel benzoisothiazole derivative that can be a bactericidal compound having excellent characteristics such as sustained effect and broad spectrum.

（式（１）中、Ａは、Ｃ２〜Ｃ１２のアルキレン、Ｃ２〜Ｃ１２のハロゲン化アルキレン、Ｃ２〜Ｃ１０のアルケニレン、Ｃ２〜Ｃ１０のハロゲン化アルケニレン、Ｃ２〜Ｃ１０のアルキニレン、（Ｃ２〜Ｃ４アルキレンオキシ）ｐ（Ｃ２〜Ｃ４アルキレン）（ｐは、１〜３から選択される整数を表す）、（Ｃ１〜Ｃ４アルキレン）フェニレン（Ｃ１〜Ｃ４アルキレン）又は（Ｃ１〜Ｃ４アルキレン）ピリジンジイル（Ｃ１〜Ｃ４アルキレン）を表す。） In order to solve the above problems, the present invention provides a bis (benzoisothiazole) derivative represented by the following general formula (1).

(In Formula (1), A is C2-C12 alkylene, C2-C12 halogenated alkylene, C2-C10 alkenylene, C2-C10 halogenated alkenylene, C2-C10 alkynylene, (C2-C4 alkyleneoxy) P) (C2-C4 alkylene) (p represents an integer selected from 1 to 3), (C1-C4 alkylene) phenylene (C1-C4 alkylene) or (C1-C4 alkylene) pyridinediyl (C1-C4) Alkylene))

（式（２）中、Ｘは、ＣＩ、Ｂｒ、Ｉ、ＯＳＯ_２ＣＨ_３、ＯＳＯ_２Ｃ_６Ｈ_５又はＯＳＯ_２Ｃ_６Ｈ_４ＣＨ_３を表す。）

（式（３）中、Ａは、Ｃ２〜Ｃ１２のアルキレン、Ｃ２〜Ｃ１２のハロゲン化アルキレン、Ｃ２〜Ｃ１０のアルケニレン、Ｃ２〜Ｃ１０のハロゲン化アルケニレン、Ｃ２〜Ｃ１０のアルキニレン、（Ｃ２〜Ｃ４アルキレンオキシ）ｐ（Ｃ２〜Ｃ４アルキレン）（ｐは、１〜３から選択される整数を表す）、（Ｃ１〜Ｃ４アルキレン）フェニレン（Ｃ１〜Ｃ４アルキレン）又は（Ｃ１〜Ｃ４アルキレン）ピリジンジイル（Ｃ１〜Ｃ４アルキレン）を表す。） Further, the present invention includes the step of reacting a halogenated benzoisothiazole compound represented by the following general formula (2) with a diol compound represented by the following general formula (3): A process for the preparation of the bis (benzoisothiazole) derivatives shown is provided.

(In formula (2), X represents CI, Br, I, OSO ₂ CH ₃ , OSO ₂ C ₆ H ₅ or OSO ₂ C ₆ H ₄ CH _3. )

(In Formula (3), A is C2-C12 alkylene, C2-C12 halogenated alkylene, C2-C10 alkenylene, C2-C10 halogenated alkenylene, C2-C10 alkynylene, (C2-C4 alkyleneoxy) P) (C2-C4 alkylene) (p represents an integer selected from 1 to 3), (C1-C4 alkylene) phenylene (C1-C4 alkylene) or (C1-C4 alkylene) pyridinediyl (C1-C4) Alkylene))

  Furthermore, the present invention provides a fungicide containing a bis (benzoisothiazole) derivative represented by the general formula (1) as an active ingredient.

  According to the present invention, a novel benzoisothiazole derivative that can be a bactericidal compound having excellent characteristics such as sustained effect and broad spectrum is provided.

  Hereinafter, preferred embodiments for carrying out the present invention will be described. In addition, embodiment described below shows an example of typical embodiment of this invention, and, thereby, the range of this invention is not interpreted narrowly.

1. Bis (benzoisothiazole) derivative The novel benzoisothiazole derivative according to the present invention is represented by the following general formula (1). Hereinafter, the bis (benzoisothiazole) derivative will be described in detail.

In the general formula (1), A represents C2 to C12 alkylene, C2 to C12 halogenated alkylene, C2 to C10 alkenylene, C2 to C10 halogenated alkenylene, or C2 to C10 alkynylene. C2-C10 alkynylene includes C4-C10 alkynylene having 1 to 3 triple bonds between carbon atoms.
In this case, when the number of carbon atoms is two or more, the bond positions on the two bonds A coming out of A are carbons that are separated from each other even if they are adjacent to each other. It may be.

A represents (C2-C4 alkyleneoxy) p (C2-C4 alkylene). p represents an integer selected from 1 to 3. p is preferably 1 or 2. The (C2-C4 alkyleneoxy) p (C2-C4 _{alkylene), (CH 2 CH 2 O} ) p, from _{(CH 2 CH 2 CH 2 O} ) p and _{(CH 2 CH 2 CH 2 CH} 2 O) p C2-C4 alkylene bonded through a structure selected from the group consisting of oxygen.
In this case, the bond position on the same alkylene between one of the two bonds coming out of A and one of the two bonds of oxygen is 3 or more carbon atoms. The carbons may be adjacent to each other, or may be carbons that are further away from the adjacent positions. In addition, when the number of carbon atoms is 3 or more, the bond position on the same alkylene of one of the two oxygen bonds and one of the other oxygen bonds is adjacent to each other. Or carbon at a position distant from the adjacent position.

Furthermore, A represents (C1-C4 alkylene) phenylene (C1-C4 alkylene) or (C1-C4 alkylene) pyridinediyl (C1-C4 alkylene). This A includes (CH ₂ ) _m —Ar— (CH ₂ ) _n (m and n are each an integer selected from 1 to 3. Ar represents phenylene or pyridinediyl). .
In this case, the bond position on the same alkylene between one of the two bonds from A and one of the two bonds of phenylene or pyridinediyl has two carbon atoms. In the above case, they may be the same carbon or different carbons. Further, the positions of the two bonds of phenylene and pyridinediyl may be ortho, meta or para positions.

  The bis (benzoisothiazole) derivative according to the present invention exhibits an excellent bactericidal action against a wide range of plant diseases. For this reason, this compound is useful as an active ingredient of agricultural and horticultural fungicides.

2. Method for Producing Bis (benzoisothiazole) Derivative A method for producing a bis (benzisothiazole) derivative according to the present invention will be described below.

  A bis (benzoisothiazole) derivative represented by the following general formula (1) is a base of a halogenated benzoisothiazole compound represented by the following general formula (2) and a diol compound represented by the following general formula (3). (See Reaction formula (1)).

Reaction formula (1)

In the formula, X represents CI, Br, I, OSO ₂ CH ₃ , OSO ₂ C ₆ H ₅ or OSO ₂ C ₆ H ₄ CH ₃ . The definition content of A is as described above.

  In this production process, 2 times mole of the halogenated benzoisothiazole compound represented by the general formula (2) reacts with 1.0 to 1.5 times mole of the diol compound represented by the general formula (3). Thus, a 1-fold molar amount of the bis (benzothiazole) compound represented by the general formula (1) is produced.

  The addition amount of the diol compound represented by the general formula (3) is preferably 1.0 to 1.3 times moles relative to 2 times moles of the halogenated benzoisothiazole compound represented by the general formula (2). is there.

The base is not particularly limited, but is preferably an alkali metal hydride such as sodium hydride (NaH), a carbonate such as potassium carbonate (K ₂ CO ₃ ) or sodium carbonate (Na ₂ CO ₃ ), potassium hydroxide ( KOH), alkali metal hydroxides such as sodium hydroxide (NaOH), and tertiary amines such as triethylamine [(C ₂ H ₅ ) ₃ N] can be used.

  In this production process, it is desirable to use a solvent. For example, amides such as dimethylformamide (DMF) and dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide (DMSO); diethyl ether, tetrahydrofuran (THF) and the like Ethers such as benzene, xylene and toluene; alcohols such as ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; dichloromethane, chloroform, Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; solvents such as water can be used alone or in combination of two or more.

  In addition, a phase transfer catalyst such as a quaternary ammonium salt such as tetrabutylammonium salt, crown ether and the like may be added to the reaction mixture. In this case, the solvent to be used is not particularly limited, but benzene, chloroform, dichloromethane, hexane, toluene and the like can be used.

  It is preferable that the reaction temperature of this manufacturing process is 0-200 degreeC. When the reaction temperature is less than 0 ° C., the reaction rate is slow, and when the reaction temperature is higher than 200 ° C., the reaction rate becomes too fast and the side reaction tends to proceed, which is not preferable. The reaction time can be appropriately determined in consideration of temperature conditions, pressure conditions, etc., but is preferably performed in the range of 30 minutes to 24 hours.

3. Disinfectant The bis (benzoisothiazole) derivative according to the present invention exhibits a control effect against a wide range of plant diseases, and is suitably used as an active ingredient of an agricultural and horticultural disinfectant. Examples of applicable diseases include the following.

  Soybean rust (Phakopsora pachyrhizi, Phakopsora meibomiae), rice blast (Pyricularia grisea), rice sesame leaf blight (Cochliobolus miyabeanus), rice leaf blight (Xanthomonas oryzae), rice leaf blight (Rhizoctonia solani) Nuclear disease (Helminthosporium sigmoideun), rice seedling disease (Gibberella fujikuroi), rice seedling blight (Pythium aphanidermatum), apple powdery mildew (Podosphaera leucotricha), apple black star disease (Venturia inaequalis), apple morinia disease (Monilinia malinia) Apple spot leaf rot (Alternaria alternata), apple rot (Valsa mali), pear black spot (Alternaria kikuchiana), pear powdery mildew (Phyllactinia pyri), pear scab (Gymnosporangium asiaticum), pear black scab (Venturia nashicola) , Grape powdery mildew (Uncinula necator), grape downy mildew (Plasmopara viticola), grape late rot (Glomerella cingulata), barley powdery mildew (Erysiphe graminis f. Sp hordei), barley black rust Disease (Puccinia graminis), barley yellow rust (Puccinia striiformis), barley leaf (Pyrenophora graminea), barley cloud (Rhynchosporium secalis), wheat powdery mildew (Erysiphe graminis f. Sp tritici), wheat red rust recondita), wheat yellow rust (Puccinia striiformis), wheat eyespot (Pseudocercosporella herpotrichoides), wheat red mold (Fusarium graminearum, Microdochium nivale), wheat blight (Phaeosphaeria nodorum), wheat leaf blight (Septoria tritici) , Cucumber powdery mildew (Sphaerotheca fuliginea), Cucumber anthracnose (Colletotrichum lagenarium), Cucumber downy mildew (Pseudoperonospora cubensis), Cucumber gray plague (Phytophthora capsici), Tomato powdery mildew (Erysiphe cichoracearum) Diseases (Alternaria solani), eggplant powdery mildew (Erysiphe cichoracearum), strawberry powdery mildew (Sphaerotheca humuli), tobacco powdery mildew (Erysiphe cichoracearum), sugar beet Brown spot disease (Cercospora beticola), corn smut (Ustillaga maydis), ash streak (Monilinia fructicola) of fruit fruit tree, gray mold disease (Botrytis cinerea) which makes various crops, sclerotia disease (Sclerotinia sclerotiorum), etc.

  Examples of applied plants include wild plants, plant cultivars, plants obtained by conventional biological breeding such as crossbreeding or protoplast fusion, plant cultivars, genetically modified plants and plant cultivars obtained by genetic manipulation. Can be mentioned. Examples of genetically modified plants and plant cultivars include herbicide-tolerant crops, pest-tolerant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes for diseases, improved crops, improved yields Examples include crops, crops with improved shelf life, and crops with improved yield. Specific examples of genetically modified plant cultivars include those containing registered trademarks such as ROUNDUP READY, LIBERTY LINK, CLEARFIELD, YIELDGARD, HERCULEX, and BOLLGARD.

  The method of using the bactericide according to the present invention is not particularly limited. For example, it may be used as it is, or may be used after being diluted to a desired concentration with a diluent such as water. In addition, a plurality of types of bis (benzoisothiazole) derivatives according to the present invention may be mixed, or may be mixed with other drugs and the like within a range that does not inhibit the effect of the bactericidal agent. The drug that can be used in combination is not particularly limited, and for example, other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, and the like can be used.

Examples of insecticides that can be used are organophosphorus insecticides (fenitrothion, malathion, acephate, diazinon, etc.), carbamate insecticides (benfuracarb, mesomil, carbosulfurne, etc.), pyrethroid insecticides (alleslin, permethrin, fenvalerate) , Etofenprox, silafluophene, etc.), nereistoxin insecticides (cartap, thiocyclam, etc.), neonicotinoid insecticides (imidacloprid, acetamiprid, thiamethoxam, dinotefuran, etc.), IGR agents (diflubenzuron, cyromazine, etc.), fipronil, Examples include emamectin benzoate, pyridalyl, propylene glycol monofatty acid ester, and BT agent.
Combinable fungicides include copper fungicides (inorganic copper, organic copper, nonylphenyl ether sulfonate copper, etc.), inorganic sulfur agents, organic sulfur fungicides (mannebu, manzeb, ambam, propineb, thiuram, etc.), organic phosphorus Fungicides (fosetyl, tolcrofosmethyl, etc.), melanin biosynthesis inhibitors (fusalide, tricyclazole, pyrokilone, carpropamide, diclocimet, phenixanil), benzimidazole fungicides (thiophanate methyl, benomyl, dietofencarb, etc.), dicarboximide (iprodione) , Procymidone), acid amide fungicides (mepronil, flutolanil, boscalid, furametopil, tifluzamide, metalaxyl, etc.), sterol biosynthesis inhibitors (triflumizole, tebuconazole, ipconazole) Metconazole, epoxiconazole, etc.), strobilurin fungicides (azoxystrobin, cresoxime methyl, trifloxystrobin, etc.), anilinopyrimidine fungicides (mepanipyrim, cyprodinil, etc.), antibacterial agents (oxolinic acid, teclophthalam, etc.) Antibiotic bactericides (such as kasugamycin, polyoxin, streptomycin, etc.), probenazole, ferrimzone, TPN, fludioxonil, iminotadine acetate, cyazofamide, cyflufenamide and the like.
Examples of miticides that can be used in combination include bifenazate, milbemectin, etoxazole and the like.
As herbicides that can be used in combination, phenoxy acid herbicides (2,4-D, chromeprop, fluazifop, etc.), carbamate herbicides (bench au carve, molinate, pyributicarb, etc.), acid amide herbicides (pretilachlor, diflufeni) Cans, mefenasets, caffentrol, ashram, etc.), urea herbicides (eg, Daimron, isouron), sulfonylurea herbicides (eg, imazosulfuron, thifensulfuron methyl, nicosulfuron, halosulfuron methyl), triazine herbicides (atrazine, simethrin) , Simazine, triadifram, etc.), diazine herbicides (bentazone, bromacil, etc.), diazole herbicides (pyrazolate, oxadiazone, etc.), bipyridyllium herbicides (paraquat, etc.), dinitro Niline herbicides (trifluralin, pendimethalin, oryzalin, etc.), aromatic carboxylic acid herbicides (fentrazamide, imazapyr, etc.), pyrimidyloxybenzoic acid herbicides (bispyribac sodium salt, etc.), fatty acid herbicides (tetrapion) ), Amino acid herbicides (glyphosate, glufosinate, etc.), nitrile herbicides (chlorthamide, etc.), cyclohexanedione herbicides (cetoxydim, cretodim, etc.), phenylphthalimide herbicides (chlorphthalim, etc.), butamifos, pentoxazone, benzo Bicyclon etc. are mentioned.
Examples of plant growth regulators that can be used include Uniconazole P, Daminogit, paraffin, wax, and benzylaminopurine.

  The bactericidal agent according to the present invention is usually mixed with a carrier and formulated for use. In addition, if necessary, further additives for various preparations such as surfactants, wetting agents, sticking agents, thickeners, stabilizers, etc. are added to form dosage forms such as wettable powders, powders, and flowables. It can be used as a preparation.

  The content of the carrier is usually in the range of 0.1 to 80% by weight. Examples of the carrier include solid carriers such as fine powder or granular materials such as kaolin, attapulgite, bentonite, acid clay, borophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic silicon hydroxide. It is done. As carriers, aromatic hydrocarbons such as xylene and methylnaphthalene; alcohols such as isopropanol, ethylene glycol and cellosolve; ketones such as acetone, cyclohexanone and isophorone; vegetable oils such as soybean oil and cottonseed oil; dimethyl sulfoxide, acetonitrile, water and the like And a liquid carrier.

  Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate esters, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate esters, naphthalene sulfonic acids Anionic surfactants such as formaldehyde condensates and polycarboxylic acid type polymers; nonionics such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters Surfactant etc. are mentioned. In addition, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP (isopropyl acid phosphate), xanthan gum and the like can be mentioned as preparation adjuvants.

  Some of the preparations are used as they are, and others are used after being diluted to a predetermined concentration with a diluent such as water. The concentration of the bis (benzoisothiazole) derivative according to the present invention when diluted is preferably in the range of 0.001 to 1.0%. Moreover, the usage-amount of the bis (benzoisothiazole) derivative based on this invention becomes like this. Preferably it is 20-5000g, More preferably, it is 50-1000g per 1 ha of agricultural and horticultural land, such as a field, a field, an orchard, and a greenhouse. These use concentrations and use amounts can be appropriately increased or decreased depending on the dosage form, use time, use method, use place, target crop, etc. without being limited to the above range.

  Hereinafter, production examples, formulation examples, and test examples of bis (benzoisothiazole) derivatives and fungicides according to the present invention will be shown to specifically describe the present invention. The present invention is not limited to the production examples shown below unless the gist thereof is exceeded. Commercially available products can be used as appropriate for the compounds used in the following production examples. The physical properties of the target compounds obtained in each Example were measured under the conditions shown in “Table 1” below.

  Regarding the target compounds obtained in the examples of the bis (benzoisothiazole) derivatives represented by the above general formula (1), the chemical structure and melting point thereof are shown in “Table 2”, the IR spectrum, the NMR spectrum, and the measured values of the melting points. The results are shown in “Table 3”. Some of these examples will be described in detail below for production examples, formulation examples, and test examples.

<Production Example 1>
3,3 ′-(oxyethyleneoxy) bis (1,2-benzisothiazole-1,1-dioxide) (Compound No. 1 in “Table 1”)
3-Chlorobenzoisothiazole-1,1-dioxide (403 mg, 2.0 mmol) was added in portions into ethylene glycol (1 ml) with stirring at room temperature. After stirring for 3 hours, the reaction was poured into ice water (30 ml). The precipitated solid was collected by filtration, washed with water and dried. The obtained solid was recrystallized using ethyl acetate as a solvent to obtain “Compound 1”.
Yield: 125 mg (32%)
Melting point: 168-170 ° C

<Production Example 2>
3,3 ′-(oxyethyleneoxyethyleneoxy) bis (1,2-benzisothiazole-1,1-dioxide) (Compound No. 7 in “Table 1”)
3-Chlorobenzoisothiazole-1,1-dioxide (403 mg, 2.0 mmol) was added in portions into a mixture of diethylene glycol (106 mg, 1.65 mol) and pyridine (5 ml) with stirring at room temperature. . After stirring overnight, the reaction was poured into ice water (20 ml). The precipitated solid was collected by filtration, washed with water and dried. The obtained solid was recrystallized using ethyl acetate as a solvent to obtain “Compound 7”.
Yield: 174 mg (40%)
Melting point: 195-196 ° C

<Production Example 3>
3,3 ′-[1,4-phenylenebis (methyleneoxy)] bis (1,2-benzisothiazole-1,1-dioxide) (Compound No. 9 in “Table 1”)
3-Chlorobenzoisothiazole-1,1-dioxide (403 mg, 2.0 mmol) was added in small portions to a mixture of p-xylene glycol (138 mg, 1 mmol), triethylamine (242 mg, 2.4 mmol) and tetrahydrofuran (5 ml). Was added at room temperature with stirring. After stirring overnight, the reaction was poured into ice water (30 ml). The precipitated solid was collected by filtration, washed with water and dried. The obtained solid was recrystallized using ethyl acetate as a solvent to obtain “Compound 9”.
Yield: 61 mg (13%)
Melting point: 245-250 ° C

<Formulation example 1>
1. Powder The powder was prepared by pulverizing and mixing 3 parts by weight of the bis (benzoisothiazole) derivative of Compound No. 1 in Table 1 (Compound 1 obtained in Production Example 1), 40 parts by weight of clay, and 57 parts by weight of talc. Prepared. In addition, the formulation example illustrated here can change the mixing ratio of an active ingredient, a carrier (diluent), and an adjuvant in a wide range.

<Formulation example 2>
2. 50 wt parts of bis (benzoisothiazole) derivative of compound No. 4 in "Table 1", 5 parts by weight of lignin sulfonate, 3 parts by weight of alkyl sulfonate, and 42 parts by weight of diatomaceous earth are mixed. A wettable powder was prepared.

<Formulation example 3>
3. Granules 5 parts by weight of the bis (benzoisothiazole) derivative of Compound No. 5 in “Table 1”, 43 parts by weight of bentonite, 45 parts by weight of clay, and 7 parts by weight of lignin sulfonate are added and water is added. After kneading, they were processed and dried into granules with an extrusion granulator to obtain granules.

<Formulation example 4>
4). Emulsion 20 parts by weight of the bis (benzoisothiazole) derivative of Compound No. 9 in Table 1 (Compound 9 obtained in Production Example 3), 10 parts by weight of polyoxyethylene alkyl allyl ether, polyoxyethylene sorbitan monolaur 3 parts by weight of a rate and 67 parts by weight of xylene were uniformly mixed and dissolved to prepare an emulsion.

<Test Example 1>
1. Rice blast control effect test The compounds of Table 1 prepared according to Formulation Example 2 after transplanting rice (variety: Koshihikari) at the 3 leaf stage into a 1 / 5000a Wagner pot filled with paddy soil. Was applied to the water surface to a predetermined concentration (120 g / 10a). 10 to 20 days after the drug treatment, a spore suspension of rice blast fungus formed on rice disease was spray-inoculated, and kept at 24-32 ° C. and high humidity in a vinyl tunnel in a glass greenhouse. 5 to 15 days after inoculation, the number of lesions per pot was measured, and the control value (%) was calculated by the following formula.
Control value = (1− number of lesions in treated area / number of lesions in untreated area) × 100

  As a result, the compounds of Compound Nos. 1, 2, 3, 4, 5, 6, 7, 8, and 9 were found to have an excellent effect of a control value of 50% or more at an active ingredient concentration of 120 g / 10a.

  The bis (benzoisothiazole) derivative according to the present invention and the fungicide containing this as an active ingredient exhibit an excellent control effect against agricultural and horticultural harmful organisms. Therefore, the present invention can be widely used in agricultural and horticultural production sites and can greatly contribute to these industries.

Claims (5)

A bis (benzoisothiazole) derivative represented by the following general formula (1).

(In Formula (1), A is C2-C12 alkylene, C2-C12 halogenated alkylene, C2-C10 alkenylene, C2-C10 halogenated alkenylene, C2-C10 alkynylene, (C2-C4 alkyleneoxy) P) (C2-C4 alkylene) (p represents an integer selected from 1 to 3), (C1-C4 alkylene) phenylene (C1-C4 alkylene) or (C1-C4 alkylene) pyridinediyl (C1-C4) Alkylene)) The A in the formula (1) is —CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ —,
_{-CH 2 CH 2 CH 2 CH 2} -, - (CH 2) 5 -, - (CH 2) 6 -,
_{-CH 2 CH = CHCH 2 -,} - CH 2 CH 2 OCH 2 CH 2 -,
_{- (CH 2 CH 2 O)} 2 CH 2 CH 2 -, or

Is,
The bis (benzoisothiazole) derivative according to claim 1. A bis (benzoiso) represented by the following general formula (1), comprising a step of reacting a halogenated benzoisothiazole compound represented by the following general formula (2) with a diol compound represented by the following general formula (3): A method for producing thiazole) derivatives.

(In formula (2), X represents CI, Br, I, OSO ₂ CH ₃ , OSO ₂ C ₆ H ₅ or OSO ₂ C ₆ H ₄ CH _3. )

(In Formula (1) and Formula (3), A is C2-C12 alkylene, C2-C12 halogenated alkylene, C2-C10 alkenylene, C2-C10 halogenated alkenylene, C2-C10 alkynylene, C2-C4 alkyleneoxy) p (C2-C4 alkylene) (p represents an integer selected from 1 to 3), (C1-C4 alkylene) phenylene (C1-C4 alkylene) or (C1-C4 alkylene) pyridine Diyl (C1-C4 alkylene) is represented.) A bactericide containing a bis (benzoisothiazole) derivative represented by the following general formula (1) as an active ingredient.
(In Formula (1), A is C2-C12 alkylene, C2-C12 halogenated alkylene, C2-C10 alkenylene, C2-C10 halogenated alkenylene, C2-C10 alkynylene, (C2-C4 alkyleneoxy) P) (C2-C4 alkylene) (p represents an integer selected from 1 to 3), (C1-C4 alkylene) phenylene (C1-C4 alkylene) or (C1-C4 alkylene) pyridinediyl (C1-C4) Alkylene))

The A in the formula (1) is —CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ —,
_{-CH 2 CH 2 CH 2 CH 2} -, - (CH 2) 5 -, - (CH 2) 6 -,
_{-CH 2 CH = CHCH 2 -,} - CH 2 CH 2 OCH 2 CH 2 -,
_{- (CH 2 CH 2 O)} 2 CH 2 CH 2 -, or

Is,
The disinfectant according to claim 4.