JPS60204707A - Microbicidal - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to microbicides.
as a fungicide, especially as a bactericidal agent.
es) and the use of the known salts of 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide as bactericides.

The use of salts of 3-keto-2H,31(-1,2-benzisothiazole 1,1-dioxide, e.g. monoethanolamine salt) as sweeteners is already known (
See, eg, U.S. Pat. No. 3,325,475).

3-Alkenyloxy-1,2-benzisothiazole 1,1-dioxides, such as 3-allyloxy-1,
2-benzisothiazole 1,1-dioxide and their use in the field of plant protection, in particular as a fungicide for rice, are also known (Japanese Patent No. 7,014,
301. C.

A, 73:45500m).

However, under certain conditions, the action of these substances has not always been satisfactory in certain fields of use.

Pyridine salts, optionally mono- or di-substituted with methyl, having fungicidal and fungicidal properties are also known (see Japanese Patent No. 40-022620).

Ammonium compounds, such as ammonium, dimethyl-alkylbenzyl-ammorum and hydroxyethylammonium compounds, and salts of 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide are also known.

They have a wide variety of uses, for example as disinfectants and as fungicides or bactericides in the field of plant protection (U.S. Pat. No. 3,280,137. 8022-
624 and Japanese Patent No. 7209 428).

For example, formula (I), which is known as a sweetener, [wherein R1 is hydrogen, alkyl having 1N18 carbon atoms, or optionally mono- or tri-substituted by hydroxyl and/or mono- or tri-substituted by amino] represents an alkyl of 1 to 6 carbon atoms which may be tri-substituted or a carboxyl-substituted alkyl of 1 to 4 carbon atoms, or optionally with the same or different substituents among nitro and chlorine; represents phenyl which may be mono- or tri-substituted, or represents cycloalkyl having 5 to 6 carbon atoms, or 1 may be optionally saturated or unsaturated; may be mono-substituted or tetra-substituted with alkyl or hydroxyl having 1 to 4 carbon atoms, and 1
~3 identical or different heteroatoms and a total of 5 or 6 ring members, R2 is alkyl having 1 to 18 carbon atoms, or l/'t optionally monosubstituted by hydroxyl, ) represents an alkyl group having 1 to 6 carbon atoms which may be mono- or tri-substituted and/or mono- or tri-substituted by ami/, or a carboxyl group having 1 to 4 carbon atoms; or phenyl, optionally mono- or tri-substituted by the same or different substituents from nitro and chlorine; or cycloalkyl having 5 to 6 carbon atoms; or optionally saturated or unsaturated, optionally mono- or tetra-substituted with alkyl or hydroxyl having 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms represents a heterocyclic structure having the same or different petro atoms and a total of 5 or 6 ring members,
And Ha is hydrogen, alkyl having 1 to 6 carbon atoms, H 1 NH2, -C-NH2, benzyl, or having 1 to 6 carbon atoms.
represents a hydroxyalkyl group of 3, except for 7-, di-, and triethanolamine compounds, or R1 and R2, together with the nitrogen atom where they are located, optionally represent another group. a 5- or 6-membered ring which may contain a teloelement and optionally be substituted by a keto group or a fused 5- or 6-membered ring and/or an alkyl having 1 to 4 carbon atoms; 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide, except for the pyridine ring which may be optionally substituted with methyl, is a sterilizing and killing agent. It has now been found to have fungicidal and bactericidal properties.

Furthermore, formula (IA) O! The compound is particularly known as fire blight.
It was also found to have excellent activity against microorganisms that cause .

Surprisingly, 3-keto-2H,3H of general formula (I)
The salts of -1,2-benzisothiazole 1,1-dioxide have higher It has M microbial agent activity.

Therefore, the use according to the invention of salts of 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide is an advantage to the art.

Formula (I) is the 3-keto-2H used according to the invention,
A general definition of the salts of 3H-1,2-benzisothiazole 1,1-dioxide is given.

Preferred compounds of formula (I) are: R1 is hydrogen, alkyl having 1 to 1B carbon atoms, in particular methyl, ethyl, n- and isopropyl, n-, secondary, tertiary and iso-butyl, neopentyl, isooctyl, dodecyl, tetradecyl and stearyl, hydroxyalkyl having 1 to 3 carbon atoms, aminoalkyl having 1 to 3 carbon atoms, especially 2-7 minoethyl, carboxyalkyl having 1 to 3 carbon atoms in the alkyl moiety,
Especially carboxymethyl, 2-carboxyethyl and 1
-carboxyethyl or phenyl optionally mono- or di-substituted with the same or different substituents among nitro and chlorine, in particular 3-nitrophenyl, 4-nitrophenyl, 3-chlorophenyl, 4
-chlorophenyl, 3,4-dichlorophenyl and 2
．． 6-dichlorophenyl, or cyclopentyl or cyclohexyl, or 1 to 3
optionally saturated nitrogen and/or oxygen atoms and optionally mono- or tetra-substituted with alkyl having 1 to 3 carbon atoms or mono- or tetra-substituted with hydroxyl. 5- or 6-membered heterocyclic structures, which may be present or unsaturated, in particular pyridine, pyrimidine, 4-methylpyrimidine, 1,2.4-) lyazole, l, 2°3-
triazole, tetrahydropyran and tetrahydroxypyran groups, R2 is alkyl having 1 to 18 carbon atoms, especially methyl, ethyl, n- and isopropyl, n-, secondary,
Tertiary and iso-butyl, neopentyl, inoctyl, dodecyl, tetradecyl and stearyl, hydroxyalkyl having 1 to 3 carbon atoms, 1 to 3 carbon atoms
3 aminoalkyl, especially 2-aminoethyl, carboxyalkyl having 1 to 3 carbon atoms in the alkyl moiety, especially carboxymethyl, 2-carboxyethyl and l-carboxyethyl, or optionally the same from nitro and chlorine or phenyl which may be mono- or di-substituted with different substituents, in particular 3-nitrophenyl, 4-nitrophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl and 2,6-
dichlorophenyl, or cyclopentyl or cyclohexyl, or has 1 to 3 nitrogen and/or nitrogen atoms and is optionally mono- or tetra-substituted by alkyl having 1 to 3 carbon atoms; optionally saturated or unsaturated 5- or 6-membered heterocyclic structures which may be mono- or tetra-substituted by hydroxyl or by hydroxyl, especially pyridine, pyrimidine, 4- methylpyrimidine, 1,2.4-triazole, 1,2.3-triazole, tetrahydropyran and tetrahydroxypyran groups, or R1 and R2 together with the nitrogen atom on which they are located; may optionally contain another hetero element and may be optionally substituted by a keto group or a fused 5- or 6-membered ring and/or an alkyl having 1 to 4 carbon atoms. 5- or 6-membered rings, especially morpholine, imidazole, 2-methyl-imidazole, pyrazole, imidazolidine, 2-iso-propyl-3-methyl-imidazolidine, piperidine, piperazinyl, l-methylpiperazinyl, 2 ,2,6゜6-titramethyl-piperidine, 2,
2,6.6-tetramethyl-4-keto-piperidine, tetrahydroxazole, tetrahydro-2-isopropyl-oxazole and a pyrrole group, R8 is hydrogen, alkyl having 1 to 6 carbon atoms, especially methyl,
1 C-NH2, which represents ethyl, n- and iso-propyl, n-, secondary, tertiary and isobutyl, pentyl and hexyl, amine, benzyl, hydroxyalkyl having 1 to 3 carbon atoms, or NH.

The following may be mentioned as examples of amine components: methylamine, diethylamine, triethylamine, methylethylamine, isopropylamine, neopentylamine, stearylamine, cyclopentylamine, cyclohexylamine, 2-aminopyridine, 3-amino-1,
2,4-) Riazole, morpholine, piperidine, pyrrolidine, piperazine, imidazole, pyrazole, 1.
2.4-triazole, 1,2.3-)lyazole, imidacilline, 2-isopropylimidacillin, 2-isopropyloxazolidine, N-methylpiveridine, N-
Methylpiperazine, N.

N'-dimethylpiperazine, N-methylpyrrolidine, hexahydro-IH-azepine, ■, 4°5.6-tetrahydro-1,2-dimethylpyrimidine, triethylenediamine, IH-benzimidazole, 1.5-diazabicyclo-[4 ,3゜0]-non-5-ene, 1,8-diazabicyclo-[5,4,0]-undec-7-ene, 2゜2.6.6-tetramethylpiperidin-4-one, amineethanol , l-hydroxy-methyl-amine, 2-amino-2-deoxyglucose, glucosylamine, l-amino-1-deoxysorbitol, trishydroxyethylamine, ethylenediamine, hydrazine or guanidine.

If one of the amine components contains several amine functions, 7- and di- or polysaccharide salts can be isolated.

The substances used as the amine component also include so-called shielded amines which decompose in aqueous or alcoholic media into amines and shielding components. Examples of these are N-)limethylsilylmorpholine, hexamethyldisilazane, piperidine-N-carboxylic acid triazolide and methyl-(4-nitrophenyloxycarbonyl)-amine. Therefore, a general hydrolyzable shielding group,
For example, amidazolylcarbonyl, pyrazolylcarbonyl or triazolylcarbonyl, phenoxycarbonylcarbonyl or trialkylsilyl are suitable for the amine.

3-keto-2H of formula CI) used according to the invention,
Salts of 3H-1,2-benzisothiazole 1,1-dioxide are known. They are, for example, the formula (n) O! 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide, optionally in the presence of a suitable solvent such as water, alcohol or dimethylformamide, at elevated temperature, especially 40°C. ~70°C, when mixed with amines of the formula (m) 1 y-Rt (m) ■ a [wherein R1-R3 have the above meanings] (for example, Japanese Patent No. 13076 ( 1965), Japanese Patent No. 15634 (19
63) and U.S. Pat. No. 3,325,475).

The salts can also be prepared in the absence of solvents by stirring, by melting or, in the case of gaseous amine components, by vaporization.

In certain embodiments using shielded amines,
A solvent such as water or alcohols must be present as a reactant.

The active compounds that can be used according to the invention exhibit strong grain bioagent activity and can be used in practice for the control of undesirable microorganisms. The active compounds can be used as plant protection agents, in particular as fungicides and fungicides and bactericides.
suitable for use.

In plant protection, the bactericidal and fungicidal agents are Plasmodi ophoromycetes (Plasmodi ophoromycetes).
etes), Oomycetes, Chytridiomycetes, Zygomycetes, Asc.
omycetes), Basidiomycetes
tes), and Deuteromyce
It is used to control te s).

In plant protection, the bacterial agents are used to control pseudomonads, rhizobacteria, enteric fungi, corynebacterial fungi and streptophyte fungi.

Examples of fungal and bacterial disease-causing microorganisms included in the general section above are mentioned without any intention to limit the invention: Botrytis species, e.g. Bat ryt is cf
n6rea); Plasmopara species, such as Plasmopara l.
icola), Uromyces species, such as Uromyces appendiculatus
iculatus), Sphaerotheca species, such as Sphaerotheca
fuliginea), Venturia (Venturia)
ia) species, such as Penturia inequalis (Ve
nturiatnaequalis), Podosphaera species, such as Bodosphaera leukotriccia (Pod.

5phaera 1eucotricha), Phytophthora species such as Phytophthora infestans
1eucotricha), Erysiphe species, e.g.
x ” Erysiphe gramini
s), Puccinia species, such as Puccinia redondit
a), Fusarium species, such as Fusarium culmorum A
, Ustilago species, such as Ustilago nuda or avenae, Septoria species, such as Septoria e/Drum (Septoria nod).

rum), Tilletia species, such as Tilletia 7
Tilletia caries, Xanthomonas species, such as Xanthomonas oryzae.

nas oryzae), Pseudomonas species, e.g.
lachrymans), Erwinia (Erwin
ia) species, such as Erwinia amylovora (Erwi
nia anylovora), Pyricularia species such as Pyricularia oryzae
yzae), Pellicularia species, such as Pellicularia a
5asaki i), Pyrenophora species 1 such as Pyrenophora teres.

ra teres) (conidial form: Drechsler
a, Syn:Helminthosporium).

Leptosphaeria species,
For example, Leptosphaeria nodrum (Leptosph)
aerLa nodorum), Cochliobolus species, e.g.
obolus 5ativus), (conidial form: Dr
echslera, Syn: He1m1 nt hos
porium), and Cercospora (Cerc
o sp o r a) species, such as Cercospora
Cercospora canesce
ns).

Because of the good tolerance by plants of the active compounds at the concentrations required to control plant diseases, it is possible to treat the above-ground parts of plants, the growths and seeds of plants, as well as the soil.

The active compounds which can be used according to the invention are present in the customary formulations, for example solutions, emulsions, suspensions, powders, foams, liniments, granules, aerosols, polymeric substances and in coating compositions for seeds. Very fine capsules inside, as well as U
It can be changed to LV cold mist or warm mist.

These formulations are prepared in a known manner, for example by combining the substances with liquid solvents and/or optionally using surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. It can be manufactured by mixing with solid carriers. When using water as extender, organic solvents can be used as co-solvents, for example.

The following are mainly suitable as liquid solvents:
aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane, or paraffins, for example mineral oil distillates, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, Also suitable as solvents for water, liquefied gases which are gases at normal temperature and pressure are, for example, halogenated hydrocarbons and aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Solid carriers include, for example, ground natural minerals such as kaolin,
Clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates are suitable solid carriers for the zero granules. e.g. crushed and fractionated natural rocks, e.g. calcite, marble,
Pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic powders, and granules of organic substances, such as sawdust, coconut husks, corncobs and tobacco stalks, are suitable. Emulsifiers and/or blowing agents include nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates. Suitable dispersants include arylsulfonates, arylsulfonates, and albumin hydrolysis products.
For example, lignin-sulphate waste liquors and methylcellulose are suitable.

Adhesives 1 For example carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules and latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the formulations.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as iron, manganese,
Salts of boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 95% by weight.
90% by weight of active compound.

The active compounds according to the invention, in their commercially available type formulations and in the use forms prepared from these formulations, are free from other active compounds, such as fungicides, insecticides ( insecticide), acaricide (
acaricide) as a mixture with selective herbicides,
It can also be present as a mixture with fertilizers and growth regulators.

The active compounds which can be used according to the invention can be used as such, in the form of their preparations or in the use forms prepared from them, for example in ready-mixed solutions, concentrates, emulsions,
It can be used in the form of foams, suspensions, wettable powders, liniments, soluble powders, powders and granules. They are common methods such as liquid dispersion, liquid atomization, atomization, granulation dispersion, powder dispersion,
Used by foaming, coating, etc. It is also possible to apply the active compounds by ultra-low volume methods or to inject the active compound preparations or the active compounds themselves into the soil. Plant seeds can also be treated.

In the treatment of plant parts, the active compound concentration in the use form can be varied within a substantial range.

They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.00% by weight.

In seed treatment, o, ooi per kg of seeds
An amount of active compound of ˜50 g, preferably 0.01 to 10 g, is generally required.

For soil treatment, 0.00001 to 0.1% by weight of
An active compound concentration of preferably o,ooot to 0.02% by weight is required at the site of action.

Erwinia amylovora, the microorganism that causes fire m-bright.
Noteworthy is the good activity against ra), in which unsubstituted ammonium compounds are mentioned in particular;
They are caused by diseases of rice, such as blast diseases, or pathogenic microorganisms of rice (Pyricularia oryzae).
) or rice pathogenic microorganisms (Xanthomonaso
It can also be used with good results for the control of bacteriosis caused by Cochlifobolus 5ativus and Pyrenophora teres.
Also noteworthy is its good activity in controlling cereal diseases caused by A. res).

The following compounds were used as comparison substances: Ol and 3xCu(OH)2, CuCl2 or Cu2(
OH) a Cl (B) Real JAJ! LA ρyrfcuraria test (rice)/protective solvent: 1
2.5 parts by weight of a7tone emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether To prepare a suitable formulation of active compound, 1 part by weight of active compound is mixed with the above amount of solvent, and The concentrate was diluted with water and the above amount of emulsifier to the desired concentration.

To test the protective activity, young rice plants were sprayed with the active compound preparation until dripping. After the spray coating has dried, the plants are coated with Pyricularia o.
inoculated with an aqueous spore suspension of S. ryzae. plant next 1
Placed in a greenhouse at 00% atmospheric humidity and 25°C.

Disease transmission was assessed 4 days after inoculation.

In this case, 1-) 411111 Nl I lower seal Ichiyukan Piko^le humanoid showed clearly superior activity compared to the prior art.

Table A' - Pyrie resistance α-de-iα test (rice)/Protection (known) O,02510 0,02510 "V" CM, 0.025 10 [Real] November Pyricularia test (rice)/systemic solvent,
12.5 parts by weight of A7Tone emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent and concentrated. The material was diluted with water and the above amount of emulsifier to the desired concentration.

To test the systemic nature, 40 ml of the active compound preparation was applied to a standard soil in which young rice plants were grown. Seven days after treatment, plants were treated with Pyriculari.
inoculated with an aqueous spore suspension of A. oryzae. The plants were then placed in a greenhouse at 100% atmospheric humidity and 25° C. until they were evaluated.

Disease transmission was assessed 4 days after inoculation.

In this test, the compounds according to the examples below, for example, showed clearly superior activity compared to the prior art.

Table B pyrtasblαriα test (rice)/systemic (known) CM, 100 3G 100 1G Zoo 22 o ll [CM, 100 20 Zoo 20 Branch S Xantbomonag oryzae test/Jl bacterosis/rice/systemic solvent: 121. 25 parts by weight of A7Tone emulsifier: 3.75 parts by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, -1 part by weight of the active compound is mixed with the above amount of solvent and concentrated The material was diluted with water and the above amount of emulsifier to the desired concentration.

To test the systemic nature, 100 ml of the active compound preparation was applied with a solution onto a standard soil in which young plants were growing. Seven days after treatment, plants were given Xanth.

An aqueous spore suspension of Monas oryzae was inoculated by needle. Then plant the plants for 24 to 24 hours until you evaluate them.
Placed in a greenhouse for 14 days at 26°C and 70-80% relative atmospheric humidity.

In this test, the compounds according to the examples below, for example, showed clearly superior activity compared to the prior art.

Xanthomonas oryttae Test/Bacteriosis/Rice/Systemic Support 11 Solvent = 49 parts by weight of acetone emulsifier: 1 part by weight of furkylaryl polyglycol ether active compound To prepare a suitable formulation, 1 Parts by weight of active compound were mixed with the above amount of solvent and the concentrate was diluted with water and the above amount of emulsifier to give the desired concentration.

To test the systemic nature, the preparations of the active compound were applied by liquid application to a standard soil in which young plants were growing. Three days after treatment, the plants were inoculated by spraying with an aqueous spore suspension of Erwinia amylovora. After 48 hours of cultivation at 100% relative atmospheric humidity, the plants were placed in a climate-controlled room at 24° C. and 70-80% relative atmospheric humidity for 8 days until they were evaluated.

In this test, the compounds according to the examples below, for example, showed clearly superior activity compared to the prior art.

Table D Erwinia amylovora test/bacteriosis/apple/systemic (B) (known) (,4) (publicly known) Erwinia amylovora test/bacteriosis/apple/protective solvent: 49 parts by weight emulsifier = 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amounts of solvent and emulsifier, and the concentrate is islanded with water. to obtain the desired concentration.

To test the protective activity, young plants were sprayed with the active compound preparation until dripping wet.

After the spray coating has dried, plant Erwinia
An aqueous spore suspension of amylomaora was inoculated by spraying. After 48 hours of cultivation at 100% relative atmospheric humidity, the plants were placed in a climate-controlled room at 24° C. and 70-80% relative atmospheric humidity for 8 days until they were evaluated.

In this test, the compounds according to the examples below, for example, showed clearly superior activity compared to the prior art.

TABLE E Iniαα Xilovorα Test/Bacteriosis,/Lymph・/Hyloborα Test/Bacteriosis,/Lymph・/Hyloborα (,0 (Public)) Manufactured by Arashi Examples The following examples are intended to further illustrate the invention.

183 g (1 mol) of 3-keto-2H,3H-1,2-
Benzisothiazole 1,1-dioxide was heated to 60 DEG C. with 59 g of isopropylamine (gaseous) or with an aqueous solution containing 59 g of isopropylamine in 200 ml of n-butanol. After 10 minutes,
The solvent was removed by distillation, yielding 242 g of salt as an oil (100% of theory).

183 g (1 mol) of 3-keto-2H,3H-1,2-
Benzisothiazole 1,1-dioxide and 86g
(1 mol) of piperidine was mixed at 50° C. in a heatable paddle mixer until the IR spectrum of the sample showed that the 502 band had shifted below 1400 cm-” (1350-1380). (268 g, 100% of theory).

183 g (1 mol) of 3-keto-2H,3H-1,2-
Benzisothiazole 1,1-dioxide and 219
g (3 mol) of n-butylamine was heated with stirring. After 10 minutes, the excess butylamine (146 g) was distilled off, leaving the salt as a colorless solid with a melting point of 88° C. (256 g, ioo% of theory).

Compounds of formulas in which the amine component was the amine below could also be prepared in the same manner as in the above examples.

19 HIN-HE, 148 20 NH, 226 22CH, NH! 157 23 C! H, NE! 148 24 n-C, H, NH, 137 25t-C, II, -NH, oil 26 n -C, H, NH, 88 271H, N-C11, -CM, -NH, oil 28 H
, N-CM, -CMt-ME, 23229 (C,H
,), N oil 30 CH3-(CM,), INH, oil 310H,-(
CB Ri, NH, Oil 46 E, N-CM, COONa 24047 CM,
-CM-COONα 1 201 ME, D, L 48 H, N-CM, CM, C00Nα 186 Continuation of page 1 Priority claim 019848 August n Kano 0 West Toy @ Inventor
Power Lulu Heinz Ri 1 Tsukuy (DE) @P3430805.9 ζFederal Republic of Italy Day 4018 Langenfeld-Hörschlasse 24

Claims (1)

[Claims] 1. Formula (I) [wherein R1 represents hydrogen, alkyl having 1-18 carbon atoms,
Represents alkyl having 1 to 6 carbon atoms which may be mono- or tri-substituted with hydroxyl and/or mono- or tri-substituted with amino, or substituted with carboxyl having 1 to 4 carbon atoms. represents alkyl, phenyl which may be mono- or trisubstituted with the same or different substituents from nitro and chlorine, cycloalkyl having 5 to 6 carbon atoms, or saturated or unsaturated,
It may be mono- or tetra-substituted with alkyl or hydroxyl having 1 to 4 carbon atoms, and 1
~3 identical or different heteroatoms and a total of 5 or 6 ring members, R2 represents alkyl having 1-18 carbon atoms or is mono- or tri-substituted with hydroxyl; represents an alkyl group having 1 to 6 carbon atoms which may be mono- or tri-substituted by amino and/or
It represents carboxyl-substituted alkyl having 1 to 4 carbon atoms, phenyl which may be mono- or tri-substituted with the same or different substituents from nitro and chlorine, or phenyl having 5 to 4 carbon atoms. 6 cycloalkyl, or may be saturated or unsaturated, mono- or tetrasubstituted by alkyl having 1 to 4 carbon atoms or hydroxyl, and containing 1 to 3 identical or different heteroatoms and Represents a heterocyclic structure having a total of 5 or 6 ring members, and R3 is hydrogen, alkyl having 1 to 6 carbon atoms, NH2, -C-NH2, benzyl, or carbon number %1
~3 hydroxyfurkyl, with the exception of the seven-, di-, and triethanolamine compounds, or R1 and R2, taken together with the nitrogen atom at which they are located, represent another heteroatom. may contain a keto group or a fused 5- or 6-membered ring and/or a 5- or 6-membered ring optionally substituted by an alkyl having 1 to 4 carbon atoms. , except for the pyridine ring which may be substituted with methyl or di-substituted. A microbicide characterized by: 2, R1 represents hydrogen, alkyl having 1 to 18 carbon atoms, hydroxyalkyl having 1 to 3 carbon atoms, aminoalkyl having 1 to 3 carbon atoms, or carboxyalkyl having 1 to 3 carbon atoms in the alkyl moiety or represents phenyl, which may be mono- or di-substituted by the same or different substituents among nitro and chlorine, or represents cyclopentyl or cyclohexyl, or represents 1 to 3 nitrogens and/or A saturated or unsaturated 5- or 6-membered compound having an oxygen atom and which may be mono- or tetra-substituted with alkyl having 1 to 3 carbon atoms or mono- or tetra-substituted with hydroxyl. represents a heterocyclic structure, and R2 is alkyl having 1 to 18 carbon atoms, hydroxyalkyl having 1 to 3 carbon atoms, aminoalkyl having 1 to 3 carbon atoms, or having 1 to 3 carbon atoms in the alkyl moiety. or phenyl, which may be mono- or di-substituted by the same or different substituents from nitro and chlorine, or cyclopentyl or cyclohexyl, or l. A saturated or unsaturated compound having ~3 nitrogen and/or oxygen atoms and which may be mono- or tetra-substituted by alkyl having 1 to 3 carbon atoms or mono- or tetra-substituted by hydroxyl. represents a 5- or 6-membered heterocyclic structure, or even if R1 and R2, together with the nitrogen atom on which they are located, contain another heteroelement. and often form keto groups or fused 5- or 6-membered rings and/or 5- or 6-membered rings optionally substituted by alkyl of 1 to 4 carbon atoms, with the proviso that by methyl excluding the pyridine ring which may be substituted, and R3 is hydrogen, alkyl having 1 to 6 carbon atoms, amino, benzyl, hydroxyalkyl having 1 to 3 carbon atoms, or
represents NH, but excludes mono-11C-NH2 di- and triethanolamine compounds, and is characterized by containing at least one salt of formula (I) according to claim 1 Microbicide. 3, R1 is hydrogen, methyl, ethyl, n- and isopropyl, n-, secondary, tertiary- and iso-butyl, neopentyl, inoctyl, dodecyl,
Tetradecyl and stearyl, 2-aminoethyl, carboxymethyl, 2-carboxyethyl and l-carpoxyethyl, phenyl, 3-nitrophenyl, 4-nitrophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl and 2,6 -dichlorophenyl, cyclopentyl, cyclohexyl or pyridine, pyrimidine, 4-methylpyrimidine, 1,2.4
-triazole, 1,2゜3-triazole, tetrahydropyran and tetrahydroxypyran groups, R2 is methyl, ethyl, n- and iso-propyl, n
-, secondary, tertiary and isobutyl, neopentyl, isooctyl, dodecyl, tetradecyl and stearyl, 2-aminoethyl, carboxymethyl, 2-carboxyethyl and l-carboxyethyl, phenyl, 3-nitrophenyl, 4-nitrophenyl, 3 -chlorophenyl, 4-chlorophenyl, 3.4
-dichlorophenyl and 2,6-dichlorophenyl,
cyclopentyl, cyclohexyl or pyridine, pyrimidine, 4-methylpyrimidine, 1.2.4-triazole, 1,2.3-)lyazole, tetrahydropyran and tetrahydroxypyran groups, or R5 and R2 are Together with the nitrogen atom located, morpholine, imidazole, 2-
Methyl-imidazole, pyrazole, imidazolidine,
2-iso-propyl-3=methyl-imidazolidine, piperidine, piperazinyl, l-methylpiperazinyl, 2
, 2,6.6-ketramethyl-piperidine, 2,2,6
．． 6-tetramethyl-4-keto-piperidine, tetrahydroxazole, tetrahydro-2-isopropyl-
oxazole and virol groups, and R3 is hydrogen, methyl, ethyl, n- and iso-propyl, n-, secondary, tertiary and isobutyl, pentyl and hexyl, -〇-NH2 A microbicide, characterized in that it contains at least one group of formula (I). 4. Use of the salts of 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide of formula (I) according to claim 1 for controlling microorganisms. 5. 3-keto- of formula CI) according to claim 1
1. A method for controlling microorganisms, which comprises applying salts of 2H,3H-1,2-benzisothiazole 1,1-dioxide to microorganisms and/or their habitat. 6. Salts of 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide of formulas (I) and (IA) according to claims 1 and 7 as fillers and/or Or a method for producing microbicides, which comprises mixing them with a surfactant. 7. (IA) O! A microbicide against microorganisms causing fire blight, characterized in that it contains 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide. 8. Use of the salt of diisothiazole 1,1-dioxide according to claim 7 for controlling microorganisms that cause fire blight. 9. 3-keto-2H,3H-1,2-benzisothiazole 1.1- of formula (IA) according to claim 7
A method for controlling microorganisms that cause fire blight, which comprises applying a dioxide salt to the microorganisms that cause fire blight and/or their environment.