JP2000026471A - 11-formyl-indolo[1,2-b][1,2]benzisothiazole and microbicidal agent for agricultural and horticultural purposes - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound, formylindolobenzisothiazole that can be synthesized with industrial advantage and is useful as a microbicidal agent for agricultural and horticultural purposes. SOLUTION: This is a new compound represented by formula I [X and Y are each H, cyano, nitro, carboxy, a halogen, a 1-6C alkyl, a 2-6C (halo)alkenyl, a (substituted) amino, a (substituted) sulfamoyl or the like; n and m are each 0-4], typically 11-formyl-indolo[1,2-b][1,2]benzisothiazole. The compound of formula I is obtained by oxidizing a compound of formula II in the presence of an oxidizing agent such as selenium dioxide in a solvent, for example, acetic acid or the like in the temperature range of from room temperature to 150 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to novel 11-formyl-indolo [1,2-b] [1,2] benzisothiazole compounds and fungicides for agricultural and horticultural use.

[0002]

2. Description of the Related Art In the cultivation of agricultural and horticultural crops, a large number of control agents are used against crop diseases, but their use is insufficient due to insufficient control effect or the emergence of drug-resistant pathogens. Due to their limitations, their potential to cause phytotoxicity and contamination of plants, and their high toxicity to humans, fish and livestock, there are not many satisfactory control agents that are not always satisfactory. Therefore, there is a strong demand for a drug that can be safely used with few such disadvantages. The disclosure of compounds related to the compounds of the present invention is disclosed in Org
nanomet. Chem. , (1997), 529, 4
45-453, the formula (A)

[0003]

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The indolo [1,2-b] [1,
2] A method for synthesizing benzisothiazole is disclosed. However, with respect to the compound of the present invention, there is no description of a synthesis example or a fungicidal activity for agriculture and horticulture.

DISCLOSURE OF THE INVENTION The present invention provides a novel 11-formyl-indolo [1,2-b] which can be synthesized industrially advantageously, is a safe and effective fungicide for agricultural and horticultural use. [1] An object of the present invention is to provide a benzisothiazole compound.

[0005]

According to the present invention, there is provided a compound represented by the general formula (1):

[0006]

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Wherein X and Y each independently represent a hydrogen atom, a cyano group, a nitro group, a carboxy group, a halogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group,
_1-6 alkoxy group, C _2-6 alkenyl group, C _1-6 haloalkenyl group, C _2-6 alkynyl group, C _1-6 alkoxycarbonyl group, C _3-6 cycloalkyl group, C _1-6 alkylthio group An amino group which may be substituted by a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkyl group or a C _1-6 alkylcarbonyl group,
_1-6 alkyl which may be substituted with a group amido group or a C _1-6 alkyl sulfamoyl group optionally substituted by a group. n represents 0 or an integer of 1-4, and when it is 2 or more, X may be different. m is 0 or 1-
Represents an integer of 4, and when it is 2 or more, Y may be different. 11) -formyl-indolo [1,2-
b] A [1,2] benzisothiazole compound, a method for producing the same, and an agricultural and horticultural fungicide containing the compound.

In the general formula (1), X and Y each independently represent a hydrogen atom, a cyano group, a nitro group, a carboxyl group, a halogen atom such as fluorine, chlorine, bromine or iodine, methyl, ethyl or propyl. , Isopropyl, butyl, isobutyl, s-butyl, t-butyl, etc.
_1-6 alkyl group, chloromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl,
C _1-6 haloalkyl groups such as 2,2,2-trifluoroethyl and pentafluoroethyl, methoxy, ethoxy,
C _1-6 alkoxy groups such as propoxy, isopropoxy, butoxy, t-butoxy, vinyl, 1-propenyl,
C _2-6 alkenyl groups such as 1-methylvinyl, allyl, 1-methylallyl, 2-butenyl, 1-fluorovinyl, 2-fluorovinyl, 2,2-difluorovinyl,
C _2-6 haloalkenyl groups such as 1,2,2-trifluorovinyl,

C _2-6 alkynyl groups such as ethynyl, 1-propynyl and 2-propynyl; and C _1-6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl and t-butoxycarbonyl. , cyclopropyl, cyclobutyl, cyclopentyl, C _{3- 6} cycloalkyl group such as cyclohexyl, methylthio, ethylthio, propylthio, such as isopropyl thio C _1-6
An alkylthio group, methylsulfinyl, ethylsulfinyl, propyl sulfinyl, C _1-6 alkylsulfinyl group such as isopropyl-sulfinyl, methylsulfonyl, ethylsulfonyl, propylsulfonyl, C _1-6 alkylsulfonyl groups such as isopropylsulfonyl,

Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl (when disubstituted, the alkyl groups may be different)
C _1-6 alkyl or acetyl, such as, propionyl, C _1-6 alkylcarbonyl optionally substituted by amino group with a group such as butyryl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s- butyl,
An amide group optionally substituted with a C _1-6 alkyl group such as t-butyl (when disubstituted, the alkyl group may be different), or methyl, ethyl, propyl,
Isopropyl, butyl, isobutyl, s-butyl, t-
It represents a sulfamoyl group which may be substituted with a C _1-6 alkyl group such as butyl (when disubstituted, the alkyl group may be different).

In the compound of the present invention, the number of carbon atoms of the substituent
Is 1-6 (C_1-6) Or 2-6 (C_2-6)
However, each has 1 to 4 (C_1-4) Or 2
4 (C _2-4) Is more preferable. Also in
The same is true.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced by the following method.

[0013]

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(Wherein, X, Y, n and m represent the same meaning as described above)

That is, [1] 6 represented by the general formula (2)
It can be produced by reacting an 11-dihydrobenzthiopyrano [4,3-b] indole compound in the presence of an oxidizing agent such as selenium dioxide in an inert solvent at a temperature ranging from room temperature to 150 ° C.

Examples of the solvent that can be used in this reaction include water, organic acids such as acetic acid, and ethers such as dioxane.

The compound represented by the general formula (2) can be produced, for example, by the method described in Japanese Patent Application No. 10-66872 by the present inventors.

In any of the reactions, after completion of the reaction, the desired product can be obtained by performing ordinary post-treatment. The structure of the compound of the present invention was determined from IR, NMR, MS and the like.

(Bactericide) Since the compound of the present invention has excellent bactericidal activity against a wide variety of filamentous fungi, it can control various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf and pasture. Can be used for For example, rice blast ( Pyricularia oryzae ) Rhizoctonia solani ( Rhizoctonia solani ) idiot disease ( Gibberella fujikuroi) sesame leaf blight ( Cochliobolus miyabeanus ) Barley Brown smut ( Ustilago nuda ) Wheat red mold ( Gibberella zeae ) Puccinia recondita) Memonbyo (Pseudocercosporella herpotrichoides) glume blotch (Leptosphaeria nodorum) powdery mildew (Erysiphe gaminis f. sp. tritici ) pink snow mold disease (Monographella nivalis) potato late blight (Phytophthora infestans) peanut brown spot disease (Mycosphaerella arachidis ) sugar beet brown spot disease (Cercospora beticola) cucumber powdery mildew (Sphaerotheca fuliginea) rot (Sclerotinia sclerotiorum) gray mold (Botrytis cinerea) downy mildew (Pseudoperonospora cubensis) tomato leaf blight (Cladosporium fulvum) late blight (Phytophthora infestans ) eggplant black blight (Corynespora melongenae) onion gray rot (Botrytis allii) strawberry powdery mildew (Sphaerotheca humuli) Apple powdery mildew (Podosphaera leucotricha) scab (Venturia inaequalis) blossom disease (Monilinia mali) persimmon anthracnose (Gloeosporium kaki) Peach Haihoshibyo (Monilinia fructicola) grape powdery mildew (Uncinula necator) and downy mildew (Plasmopara viticola ) Pear Red scab ( Gymnosporangium asiaticum) Black spot ( Alternaria kikuchiana ) Tea ring spot ( Pestalotia theae) Anthracnose ( Colletotrichum theae-sinensis ) Citrus scab ( Elisinoe fawcetti ) Blue mold ( Penicillium italicum ) It can be used for controlling Sclerotinia borealis .

In recent years, various pathogens have developed resistance to benzimidazole agents, dicarboximide agents, and the like, resulting in insufficient efficacy of these agents, and there is a need for an agent that is also effective against resistant pathogens. The compound of the present invention is not only sensitive but also has an excellent bactericidal effect against pathogenic bacteria resistant to benzimidazole agents and dicarboximide agents.

Diseases that are more preferably applied include downy mildew of grape and potato blight.

The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets. Also, by mixing the compound of the present invention into paints, fibers, and the like, it can be used as an antibacterial and fungicide for walls and bathtubs, shoes and clothes. Some of the compounds of the present invention exhibit insecticidal, acaricidal and herbicidal activities.

When the thus-obtained compound of the present invention is actually applied, it can be used in a pure form without adding other components, or can be used in the form of a general pesticide for use as a pesticide. That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like. When solid additives are used as additives and carriers, vegetable powders such as soybean grains and flour; mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, and clay; benzoic acid Organic and inorganic compounds such as soda, urea, and sodium sulfate are used. For liquid dosage forms, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane,
Cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. are used as solvents.

To obtain a uniform and stable form in these preparations, a surfactant may be added if necessary. Examples of the surfactant include, but are not particularly limited to, alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, and sorbitan to which polyoxyethylene is added. Nonionic surfactants such as higher fatty acid esters, tristyryl phenyl ether added with polyoxyethylene, sulfates of alkyl phenyl ethers added with polyoxyethylene, alkyl benzene sulfonates, sulfates of higher alcohols, alkyls Examples include naphthalene sulfonate, polycarboxylate, lignin sulfonate, formaldehyde condensate of alkylnaphthalene sulfonate, and copolymer of isobutylene-maleic anhydride.

The formulated fungicide composition of the present invention is applied to a plant, seed, water surface or soil as it is, or diluted with water or the like. In addition, the application rate, weather conditions, formulation form, application time, application method, application place, disease to be controlled,
Although it varies depending on the target crop and the like, the amount of the active ingredient compound is usually 1 to 1000 g, preferably 10 to 100 g / ha.
１００100 g. When the emulsion, wettable powder, suspension, liquid preparation, etc. are diluted with water or the like and applied, the application concentration is from 1 to 100.
The amount is 0 ppm, preferably 10 to 250 ppm, and the amount of granules, dusts and the like is usually 0.001 to 50 g, preferably 0.01 to 10 g per kg.

Although the compound of the present invention exerts a sufficient effect when used alone, it can also be used as a mixture with one or more of various fungicides, insecticides, acaricides or synergists.
Fungicides, insecticides, which can be used by mixing with the compound of the present invention;
Examples of the acaricide, nematicide, and plant growth regulator include the following.

Disinfectant: Copper agent: Basic copper chloride, basic copper sulfate and the like. Sulfur agents: thiuram, maneb, mancozeb, polycarbamate, propineb, ziram, zineb and the like. Polyhaloalkylthio agents: captan, dichlorofluanid, folpett, etc. Organic chlorine agents: chlorothalonil, fthalide, etc.

Organic phosphorus agents: IBP, EDDP, tolclofosmethyl, pyrazophos, fosetyl and the like. Benzimidazole agents: thiophanate methyl, benomyl, carbendazim, thiabendazole and the like. Dicarboximide agents: iprodione, vinclozolin, procymidone, fluoroimide and the like. Carboxamide agents: oxycarboxin, mepronil, flutranyl, teclophthalam, triclamide, pencyclone and the like. Acylalanine agents: metalaxyl, oxadixyl, furalaxyl and the like.

SBI agent: triadimefon, triadimenol, bitertanol, microbutanyl, hexaconazole, propiconazole, trifumizol, prochloraz, pefurazoate, fenarimol, pyrifenox, triforine, flusilazole, etaconazole, diclobutrazole, fluotrimazole , Furtriafen, penconazole, dicononazole, cyproconazole, imazalil, tridemorph, fenpropimorph, butiobate, epoxyconazole, metconazole and the like.

Acrylic acid-based agents: kresoxime methyl, azoxystrobin, metominostrobin and the like. Anilinopyrimidine: andpurine, mepanipyrim,
Pyrimethanil, cyprodinil and the like. Antibiotics: polyoxin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate and the like. Others: propamocarb hydrochloride, kintozen, hydroxyisoxazole, metasulfocarb, anilazine,
Isoprothiolane, probenazole, quinomethionate, dithianone, dinocab, diclomedine, mepanipyrim, ferimzone, fluazinam, pyroquilon, tricyclazole, oxolinic acid, dithianone, iminoctadine acetate, simoxanil, pyrrolnitrin, metasulfocarbine, dietofencarbine, sinafenafulinbine , Dozine, dimethomorph, phenazine oxide, carpropamide, fursulfamide, fludioxonil, famoxadone and the like.

Insecticides and miticides: Organophosphorus and carbamate insecticides: phenthion, fenitrothion, diazinon, chlorpyrifos, ES
P, bamidothion, fentoate, dimethoate, formotion, marathon, trichlorfon, thiometon,
Hosmet, Dichlorvos, Acephate, EPBP,
Methyl parathion, oxydimetone methyl, ethion,
Salithion, cyanophos, isoxathion, pyridafenthion, phosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenophos, pyraclophos, monocrotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, Carbofuran, carbosulfan, benfracarb, fratiothiocarb, propoxur, BPMC,
MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb, phenoxycarb and the like.

Pyrethroid insecticides: permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucitrinate, ethitol Fenprox, cycloprothrin, trolametrin, silafluofen, profenprox, acrinasuri, etc.

Benzoylurea and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, puprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiu Ron, acetamipsodo, imidacloprid, nitenpyram, fipronil, nicotine sulfate, rotenone, cartap, thiocyclam, bensultap, methaldehyde, machine oil, microbial pesticides such as BT and insect pathogenic virus.

Nematicides: fenamiphos, phosthiazate and the like. Acaricides: chlorbenzylate, phenisobromolate, dicofol, amitraz, BPPS, benzomate,
Hexitiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezin, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, phenothiocarb, dienochlor and the like. Plant growth regulator: gibberellins (eg gibberellin A3
, Gibberellin A4, Gibberellin A7), IAA, NA
A.

[0035]

EXAMPLES Next, the compounds of the present invention will be described in more detail by way of examples.

Example 1 Preparation of 11-formyl-indolo [1,2-b] [1,2] benzisothiazole (Compound No. 1)

[0037]

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0.56 g (5.0 mmol) of selenium dioxide
Is suspended in 5 ml of THF, 1 ml of water is added, and 50-60
[1] 6,11-dihydrobenzthiopyrano [4,3-b] indole 1.2 g (5.0 mmo)
After l) was gradually added, the mixture was stirred at 50 to 60 ° C for 2 hours. After allowing the reaction solution to cool, the solvent was distilled off under reduced pressure, the residue was suspended in chloroform, washed with saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the obtained crystals were washed with diethyl ether to obtain 0.55 g of the desired product. Yield 44%, mp. 173-174 ° C

Example 2 4-methoxy-11-formyl-indolo [1,2-
b] [1,2] benzisothiazole (Compound No. 3
9) Manufacturing

[0040]

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0.76 g (6.7 mmol) of selenium dioxide
Was suspended in 5 ml of THF, and 1 ml of water was added.
C. and 1.5 g of 10-methoxy- [1] 6,11-dihydrobenzthiopyrano [4,3-b] indole
(5.6 mmol) was added slowly, and then at 60-70 ° C. for 5 hours.
Stirred for hours. After allowing the reaction solution to cool, the solvent was distilled off under reduced pressure. The obtained residue was suspended in chloroform, washed with saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (chloroform: ethyl acetate = 7: 3) to obtain 1.1 g of the desired product. Yield 59%, mp. 180 ° C dec.

Example 3 9-Chloro-11-formyl-indolo [1,2-b]
Production of [1,2] benzisothiazole (Compound No. 50)

[0043]

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0.39 g (3.4 mmol) of selenium dioxide
Is suspended in 5 ml of THF, 1 ml of water is added, and 50-60
C. and 0.78 g of 2-chloro- [1] 6,11-dihydrobenzthiopyrano [4,3-b] indole
(2.9 mmol) was added slowly, and then at 50-60 ° C for 2 hours.
Stirred for hours. After allowing the reaction solution to cool, the solvent was distilled off under reduced pressure, the residue was suspended in chloroform, washed with saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the obtained crystals were washed with diethyl ether, and
g was obtained. Yield 72%, mp. 232-234 ° C

Example 4 9-methyl-11-formyl-indolo [1,2-b]
Production of [1,2] benzisothiazole (Compound No. 52)

[0046]

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1.78 g of selenium dioxide (15.8 mmol
l) was suspended in 10 ml of THF, and 3 ml of water was added thereto.
Heat to ~ 70 ° C and add 2-methyl- [1] 6,11-dihydrobenzthiopyrano [4,3-b] indole 4.0.
g (15.9 mmol) is gradually added, and then 60-70 ° C.
For 4 hours. After allowing the reaction solution to cool, the solvent was distilled off under reduced pressure. The obtained residue was suspended in chloroform, washed with saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (chloroform: ethyl acetate = 7: 3) to give the target compound (1.0).
g was obtained. Yield 24%, mp. 179-181 ° C

Example 5 1,4-Dimethyl-11-formyl-indolo [1,2
-B] [1,2] benzisothiazole (Compound No. 9
3) Manufacturing

[0049]

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0.36 g (3.17 mmol) of selenium dioxide
l) was suspended in 5 ml of THF, and 1 ml of water was added thereto.
Heat to 70 ° C. and add 7,10-dimethyl- [1] 6,11
After slowly adding 0.7 g (2.64 mmol) of dihydrobenzthiopyrano [4,3-b] indole,
Stirred at 70 ° C. for 5 hours. After allowing the reaction solution to cool, the solvent was distilled off under reduced pressure, the residue was suspended in chloroform, washed with saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (chloroform: ethyl acetate = 7: 3), and 0.17 g of the desired product was obtained.
I got Yield 19%, mp. 202-204 ° C

Table 1 shows typical examples of the compounds of the present invention including the above Examples.

[0052]

[Table 101]

[0053]

[Table 102]

[0054]

[Table 103]

[0055]

[Table 104]

[0056]

[Table 105]

(Bactericide) Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratio are not limited to these examples, but can be varied in a wide range. is there. Parts in the preparation examples represent parts by weight.

Example 6 Water-dispersible powder 40 parts of the compound of the present invention 53 parts of diatomaceous earth 4 parts of higher alcohol sulfate 4 parts of alkylnaphthalene sulfonate If the above are uniformly mixed and finely pulverized, the active ingredient 40 will be obtained.
% Wettable powder.

Example 7 Emulsion 30 parts of the compound of the present invention 33 parts of xylene 30 parts of dimethylformamide 7 parts of polyoxyethylene alkylaryl ether 7 parts By mixing and dissolving the above, an emulsion having an active ingredient of 30% is obtained.

Example 8 Suspending agent Compound of the present invention 10 parts Sodium ligninsulfonate 4 parts Sodium dodecylbenzenesulfonate 1 part Xanthan gum 0.2 parts Water 84.8 parts Mix above and until particle size is 1 micron or less If wet milled, a 10% active ingredient suspension is obtained.

[0061]

Next, Test Examples show that the compound of the present invention is useful as an active ingredient of various plant disease controlling agents. The control effect was determined by visually observing the growth of lesions and flora that appeared on leaves, stems and the like at the time of the survey, and calculating the control effect.

Test Example 1 Grape Downy Mildew Control Test Grape seedlings (variety "Koshu", 2
In the leaf stage), the emulsion of the compound of the present invention was treated with 200 ppm of the active ingredient.
Sprayed at the concentration of the concentration. After spraying, air dry at room temperature, and grape downy mildew ( Plasmopara viticol)
The zoosporang suspension of a ) was sprayed and inoculated, and kept in a high humidity constant temperature room (20 ° C.) where light and dark were repeated every 12 hours for 10 days. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds showed a controlling effect of 75% or more. Compound number 1,4,16,18,34,36,38,
39, 45, 50, 52

Test Example 2 Test for controlling tomato late blight Tomato seedlings (variety “Regina”, cultivated in unglazed pots)
In the 4-5 leaf stage), the emulsion of the compound of the present invention was added to the active ingredient 200
Sprayed at a concentration of ppm. After spraying, air-dry at room temperature, and tomato blight ( Phytophthora inf)
estans ) was maintained in a high-humidity thermostatic chamber (20 ° C.) for 4 days, in which light and dark were repeated every 12 hours. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compound
% Or more. Compound No. 1,52

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Claims (3)

[Claims] 1. A compound of the general formula (1) (Wherein X and Y are each independently a hydrogen atom, a cyano group, a nitro group, a carboxy group, a halogen atom, C _1-6
Alkyl group, C _1-6 haloalkyl group, C _1-6 alkoxy group, C _2-6 alkenyl group, C _2-6 haloalkenyl group, C
_2-6 alkynyl group, C _1-6 alkoxycarbonyl group, C
_3-6 cycloalkyl group, C _1-6 alkylthio group, C _1-6
Alkylsulfinyl groups, C _1-6 alkylsulfonyl group, C _1-6 alkyl or C _1-6 alkylcarbonyl amino group which may be substituted with a group, C _1-6 optionally amides optionally substituted by an alkyl group And a sulfamoyl group which may be substituted with a C _1-6 alkyl group.
n represents an integer of 0 or 1-4, and when 2 or more, X
May be different. m represents 0 or an integer of 1-4, and when it is 2 or more, Y may be different. 11) -formyl-indolo [1,2-b] [1,2]
Benzisothiazole compounds. 2. A compound of the general formula (2) Wherein X, Y, n and m have the same meanings as described above, wherein the compound represented by the general formula (1) is oxidized. (Wherein, X, Y, n and m represent the same meaning as described above). 3. A compound of the general formula (1) (Wherein, X, Y, n and m have the same meanings as described above.) 11-formyl-indolo [1,2-
b] A fungicide for agricultural and horticultural use, characterized by containing one or more [1,2] benzisothiazole compounds as an active ingredient.