JPS61155376A - Benzothiazolone derivatives, their production methods, and agricultural and horticultural fungicides containing them as active ingredients - 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 a novel benzothiazolone derivative, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.

Traditionally, agricultural and horticultural disinfectants, that is, agricultural and horticultural disinfectants, have been organic phosphorus-based and organic chlorine-based.

Various organometallic compounds are used. However, although these fungicides have excellent bactericidal effects, they are highly toxic to humans and livestock, and have a high degree of phytotoxicity and persistence to plants, so there are various limitations in their use.

On the other hand, benzimidazole compounds, acylanilide compounds, and antibiotics have been widely used due to their high activity, but recently, resistant bacteria have appeared5, and their bactericidal effects are insufficient. It's getting K.

Therefore, there is a strong demand in industry for the development of agricultural and horticultural fungicides that are effective in controlling various plant diseases and do not cause the above-mentioned adverse effects.

The present inventors have conducted extensive research in order to develop a fungicide for agriculture and horticulture that meets the above objectives. In the process, the present inventors focused on benzothiazolone derivatives, and as a result of repeated research, discovered that certain substituted benzothiazolone derivatives were novel and useful as agricultural and horticultural fungicides, and completed the present invention. I ended up doing it.

The present invention provides a novel benzothiazolone derivative, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient, particularly an agricultural and horticultural fungicide that is highly effective against tomato late blight, rice blast, barley powdery mildew, etc. The purpose is to

That is, the present invention is based on the general formula [wherein R1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, and R2 represents 100B''].

-008'A"Iha-8O*" t Show (Kokote R
"G! Indicates a cycloalkyl group having 3 to 6 carbon atoms 14
is an alkyl group having 1 to 4 carbon atoms or 7 having 2 to 4 carbon atoms
and an agricultural and horticultural fungicide containing it as an active ingredient.

The novel benzothiazolone derivative represented by the above formula (I) K exhibits a strong antibacterial effect, and can be efficiently produced by the production method of substituting the 3-position of the benzothiazolone as described below.

First, the first manufacturing method is based on the general formula [wherein R1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms]. ] to the nuclear-substituted benzothiazolone represented by the general formula n"aox c, where Bka
represents a cycloalkyl group having 3 to 6 carbon atoms, and X represents a halogen atom. This is a method (manufacturing method 1) for producing a benzothiazolone derivative represented by the general formula [wherein R1 and R3 are the same as above] by reacting an acid halide represented by the following. Here, R1 specifically includes a methyl group, ethyl group, propyl group, isopsevir group, n-butyl group, isobutyl group, tart-butyl group, methoxyl group, ethoxyl group, propoxyl group, isopropoxyl group, n −
Examples include butyroxyl group, imbutyroxyl group, and tart-butyroxyl group. In addition, an appropriate solvent or an inert solvent as a diluent can be used here.Specifically, for example, t
Ha, benzene, chlorobenzene, toluene.

Examples include hydrocarbons such as xylene; ethers such as dimethyl ether, dibutyl ether, tetrahydrofuran, and dioxane; esters such as ethyl acetate; ketones such as acetone and methyl ethyl ketone; and dimethyl sulfoxide.

Additionally, suitable bases, such as pyridine, alkylamines, to scavenge the acids formed during the reaction.

Organic bases such as piperidine or inorganic bases such as aqueous sodium, potassium carbonate, ammonia, etc. can be added. Although the reaction proceeds at room temperature, the reaction is usually faster when heated, and it is better to raise the temperature to near the boiling point of the solvent and reflux it. Although the reaction time varies depending on the solvent used, temperature, etc., the reaction is usually completed after stirring for 1 to 10 hours. After the reaction was completed, ll! precipitated in the reaction solution. The salts of the scavenger are separated from each other and the solvent of the p liquid is distilled off, or after adding an aqueous acid solution such as hydrochloric acid or water, the solvent is distilled off and the precipitate is separated from each other. General formula (I
) can be obtained.

Next, as a second production method, the general 2R'NOO
(In the formula, R4 represents an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms) is reacted with an incyanate represented by [In the formula, R1 and R4 are the same as above]. A method for producing a benzothiazolone derivative (manufacturing method 2) is mentioned.The nuclear-substituted benzothiazolone as a raw material is the same as that in manufacturing method 1.In addition, as the isocyanate represented by the general formula R'NOO, specific K 0HaN
C0,0@HsNOO.

n-(11HyN(!01 i-0@H?NOO,
n-04H@NOO, 1-04EsNOO.

5ec-04H@Neo, t-04111@NOO
, c) H, = 1 - OgCfH, -0H-OH, NCJO
, CfH80H=OHNOO, OH,=OH-OH,O
H, NcO hook, OH, -0H-OH-aH, NO
Examples include O,0Hs-CH*OH=OHNCO.

Production method 2 of the present invention has the solvent 2 reaction time etc. in production method 1.
It is similar to However, in production method 2, no base is generated in the reaction system, so there is no need to add a base (M scavenger).

Furthermore, as a third manufacturing method, the above-mentioned general formula (II)
For the nuclear-substituted benzothiazolone represented by the general formula R'
80tX In the formula, R4 represents an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms, and X represents a halogen atom. There is a method (manufacturing method 3) in which a benzothiazolone derivative represented by the general formula [wherein R1 and R4 are the same as above] is produced by reacting a sulfonyl halide represented by the following formula. The raw material, nuclear-substituted benzothiazolone, is produced using manufacturing method 1.
It is similar to Also, the general formula R'80. Specifically, the sulfonyl halide represented by X is an, so, c
! l O@HsSO@01 , n-0@HISO@0
1°1-0. H, 80, CIT n-04H@80.
(!, 1-04H, So, (j19sec-04H
*BO@(jl, tr-C4H@So@01,
0H6801Er sO,H,So,Br t n
-0,H,80,Br, i-0,H,80,Il
r+n-04B@801Br t 1-0. H@8
0@Br, 5ea-0, H@80. Br+t-0
4H180@Br, OH, lH801 (74, O
Bird=CjH-OH1B0,01.

OH, -0H=OH8O, C1, OH, =OH-OH,
CfH180, C1tCH*-OH”0H-CHsSO
*Oj*0HaOHsOII=O]ll[80
tC7.

(fH,=OH80,Br, OH,-0H-OH@
80. Brv CH, -CH=CjH80,BrrOR
,=OR-OH,OH,80,Br+0R1-
OR=OH-0'H, 80, Br.

Examples include OH, OH, 0H-Cn2O, Br, etc.

In production method 3, the solvent, base 2 reaction conditions, etc. may be carried out in the same manner as in production method 1.

The general formula (
The compounds represented by I'), (I'), (I"'), that is, the benzothiazolone derivatives represented by general formula (I), are all new compounds.

The benzothiazolone derivative of the present invention represented by the general formula (I) exhibits excellent bactericidal activity.

The agricultural and horticultural fungicide of the present invention contains the above-mentioned benzothiazolone derivative as an active ingredient, and although the active ingredient may be used as it is, it is usually used as a liquid such as water or an organic solvent, or as a solid powder or other suitable agent. Dilute a suitable medium at °C and add auxiliary agents such as wetting agents, dispersants, emulsifiers, and fixing agents as necessary to form wettable powders, liquids, emulsions, sol, and powders (including DL type powders). , formulated into fine particles, etc.

When used in the form of a wettable powder, diatomaceous earth, white carbon, etc. are added to the above active ingredients, and a wetting agent such as an alkylbenzene sulfonate, an alkyl sulfur ester, or a polyethylene glycol ether is added [mix and stir]. The solution may be diluted with water to a predetermined concentration before use. In addition, K in the form of an emulsion can be prepared by adding hydrocarbons such as xylene, benzene, toluene, etc. to the above active ingredients, and further adding polyoxyethylene-alkylaryl ethers such as polyoxyethylene nonylphenyl ether or polyoxyethylene-aliphatic alcohols. An emulsifier such as ether may be added and mixed, and when used, it may be diluted with water to a predetermined concentration. There is no particular restriction on the mixing ratio, but for example, 30 parts by weight of dimethylformamide, 35 parts by weight of xylene and 15 parts by weight of polyoxyethylene aryl ether may be mixed with 20 parts by weight of the above active ingredient.

K, which is in the form of a powder, contains the above-mentioned active ingredients and clay.

Add clay minerals such as talc and kaolin, mix and crush,
It is sufficient to use a predetermined particle size of 1 and spray it as it is. There is no limit to the percentage of the mixing ratio, but when clay is used as the clay mineral, it is preferable to use 98 parts by weight of clay to 2 parts by weight of the above-mentioned active ingredient. To make it into granules, use diatomaceous earth, calcium carbonate, and bentonite as the above-mentioned active ingredients.

Add clay, etc., and then add lignin sulfonate.

A caking aid such as polyvinyl alcohol or JL powder is added, and in some cases a surfactant is added to improve dispersibility, and granulation is performed. When using it, just spray it as it is. The mixing ratio is not particularly limited, but for example, to 10 parts by weight of the above active ingredient, 1 part by weight of calcium lignosulfonate, 0.1 part by weight of sodium sulfate, 30 parts by weight of pentonite, and 58.9 parts by weight of clay. Just mix.

The agricultural and horticultural fungicide of the present invention has the general formula (I) as described above.
Although the benzothiazolone derivative represented by is used as an active ingredient, it is also effective to use other active ingredients in combination. Active ingredients that can be used in combination here include kasugamycin, polyoxin, validamycin, phenazine-5-oxide, N-1,1,2,2-tetrachloroethylthiotetrahydrophthalimide, tetrachloroisophthalonitrile, methyl-1-(methylcarbamoyl) -2-benzimidazole carbamate, 2
．． 4-dichloro-6-(0-chloroanilino)-g-)
riazine, 1,2,5,6-titrahydropyrrolo(
3,2゜1-Lj) quinolin-4-one, 3-(3
,5-dichlorophenyl)-5-met-5-vinyl-
Bactericides such as 2゜4-oxazolidinedione and 3.3'
-ethylenebis(tetrahydro)-4,6-dimethyl-2H-1,3,5-thiadiazine-2-thione;
Carbamate fungicides such as ethylene bisdithiocarbamate zinc salt or manganese salt, bis(1-hydroxy-
2(IH) pyridine thionate) zinc salt; pyridine fungicide such as 2-pyridinethiol-1-oxide sodium salt, 0. Phosphorous fungicides such as O-diisopropyl-8-benzylphosphorothioate, O-ethyl-8,8-diphenyldithiophosphate, N-(2,6-dinitylphenyl)phthalimide, N-(2,6-dinitylphenyl)4-methyl 7-talimide fungicides such as 7-talimide, methyl-N-(2-methoxyacetyl)-N
Acylanilide fungicides such as -(2,6-xylyl)-alaninate, 1-(4-chlorophenoxy)-3,3
-dimethyl-1-(IH-1,2,4-)lyazole-
Azole fungicides such as 1-yl)-2-butanone, N-
) IJ dichloroltylthio-4-cyclohexene-1,2
-Dicarboximide; N-tetrachloroethyl f:
Dicarboximide fungicides such as ni-4-cyclohexene-1゜2-dicarboximide, 5.6-cyclohexene-1゜2-dicarboximide, etc.
Methyl-1,4-oxatine-3-carboxanilide 4,4-dioxide; 5,6-sihydro-2-methyl-
Oxatine fungicides such as 1,4-oxatine-3-carboxylate, naphthoquinone fungicides such as 2,3-dichloro-1,4-naphthoquinone; 2-oxy-3-chloro-1,4-naphthoquinone steel sulfate , pentachlornitrobenzene; 1,4-cyclo-2,5-dimethoxybenzene, steel sulfate, dihydroxide, α-cyano-3-phenoxybenzyl-2,2-dimethyl-3-(
2,2-dichlorovinyl) cyclopropane carboxylate, further K is an insecticide such as various phosphorus insecticides and carbamate insecticides, such as 0.0-diethyl 0-(2-isopropyl-4-methyl-6-pyrimidinyl) ) phosphorothioate; 0,0-dimethyl 0-(3-methyl-4-
nitrophenyl)thiophosphate 10.0-dimethyl 5-(N-methyl-N-formylcarbamoylmethyl)
Phosphorodithioate; o,o-diethyl! 3-2(
(Ethylthio)ethyl]phosphorodithioate; 0.
0-diethyl-〇-(5-phenyl-3-inxazolyl)phosphorothiony)io, O-”methyl-〇-(3
-Methyl-4-methylmercaptophenyl) thiophosphate; 0-ethyl-〇-p-cyanophenylphenylphosphonothiony); 2
,2-dichlorovinyldimethylphosphate;5-((
6-chloro-2-oxo-3-benzoxazolinyl)
methyl] 0,0-diethylphosphorodithiony);
2-Rio-1-(2,4-dichlorophenyl)vinyl diethyl phosphate; 0. O-diethyl-〇-(
0,0-dimethyl-8-
[”2-Methoxy-1,3,4-thiadiazole-5-
(4H)-onyl-(4)-methylfudithiophosphate; 2-methoxy-4H-1,3,2-benzodioxaphosphorine 2-sulfide; 0,0-diethyl-〇-(
Phosphorus-based insecticides such as 0.0-dimethylphosphorodithioate, 1-subbutyl N-methylcarbamate; S-methyl-N-((methylcarbamoyl)oxycothioacetimidate; m-tolylmethylcarbamate = 3.4-xylylmethylcarbamate; 3
,5-xylylmethylcarbamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethylcarbamate; 2-isopropoxyphenyl-N-methylcarbamate); 1,3-bis(carbamoylthio)- 2
-(N,N-dimethylamino)propane hydrochloride; carbamate insecticides such as 2-diethylamino-6-methylpyrimidin-4-yldimethylcarbamate, nicotine sulfate, 6-methyl-2,3-quinoxaline dithiocyclic s,s-dithiocarbonate, 2,4-dinitro-
6-5ec-butylphe3(2,6-difluorobenzoyl)-urea; S-tricyclohexyltine 0,0-
Some insecticides such as diisopropyl phosphorodithioate (
・Can be used by mixing with fertilizer etc.

It was. 1-(α,α-dimethylbenzyl)-3-(halatryl)urea, 3-improvir-2,1,3=benzothiadiazinone-(4)-2,2-dioxide, IP
C! , 2-chloro-Z/S/-diethyl-N-(methoxymethyl)acetanilide and other herbicides; 2-methylthio-4,6-bisethylamino-1,3,5-triazine; 2-chloro-4, 6-pisethylamino-1,3.
5-) Triazine herbicides such as riazine, Fe/*” type herbicides such as 2,4-dichlorophenoxyacetic acid and its methyl, ethyl or butyl esters 1?IL 2
．． 4.6-) Dichlorophenyl-4'-nitrophenyl ether; diphenyl ether herbicides such as 2.4-dichlorophenyl-4'-nitrophenyl ether, other urea herbicides, carbamate herbicides, Uracil herbicides, thiol carbamate herbicides, phosphorus herbicides, aniline herbicides, acid anilide herbicides, pyrazole herbicides, and KN-methoxycarbonyl-N/-4-methylphenylcarbamoylethyl increa; 1-(4
-chlorophenylcarbamoyl)-3-ethoxycarbonyl-2-methylisourea, isourea-based plant growth regulators, sodium naphthalene acetate; 1,2-dihydropyridazine-3,6-dione, etc. Can be used together.

The benzothiazolone derivative of the present invention represented by the general formula (I) as described above exhibits a strong antibacterial effect.

It is particularly effective against tomato late blight, rice blast, and barley powdery mildew, and also has strong antibacterial activity against plant-pathogenic algae, fungi, basidiomycetes, deuteromycetes, and bacteria. show.

Therefore, the present invention can be applied to various types of agriculture and gardening! FK
It can be widely used.

Next, examples of the present invention will be shown, but the present invention is not limited to these examples.

Synthesis Example 1 5-5 mmol of 6-medoxybenzothiazolone and 6.6 mmol of triethylamine were added to 1511 mmol of acetone.
6. To this solution, 101 L of acetone containing 6.0 mmol of 1 cyclopropylcarbonyl chloride was added dropwise. Thereafter, the mixture was heated under reflux for 2 hours, and then cooled to room temperature. Next, 5% aqueous hydrochloric acid solution 2014 was added, the solvent was distilled off under reduced pressure, and the precipitated crystals were separated and recrystallized from acetone-water to obtain a benzothiazolone derivative. The structural formula, yield, melting point, and elemental analysis values of this product are shown in Table 1. Synthesis Example 2.3 Synthesis Example 1 except that the raw material components were changed as shown in Table 1.
A benzothiazolone derivative was obtained by carrying out the same operation as above. The structural formula, yield, melting point and elemental analysis values of this product are shown in Table 1.

Synthesis Example 4 5.5 mmol of 6-nitylpenzothiazolone was dissolved in 5 dl of dimethyl sulfoxide. To this solution was added dropwise 3.2 mmol of methyl incyanate. 1.
Stirring was carried out for 5 hours, and the resulting reaction mixture was diluted with 2 sOd of water.
The precipitated crystals were separated from each other and recrystallized from acetone-water to obtain a benzothiazolone derivative. The structural formula, yield, melting point and elemental analysis values of this product are shown in Table 1.

Synthesis Example 5 5.5 mmol of 6-nitoxypenzothiazolone and 6.6 mmol of triethylamine were added to 15 dK of acetone.
Dissolved. 10 at of acetone containing 8.2 mmol of methanesulfonyl chloride was added dropwise to this solution under water cooling. Next, the reaction mixture was poured into ice water, and the precipitated crystals were separated and recrystallized from acetone-water to obtain a benzothiazolone derivative. Structural formula of this thing.

The yield, melting point and elemental analysis values are shown in Table 1.

Synthesis Examples 6 and 7 Synthesis Example 5 except that the raw material components were changed as shown in Table 1.
A benzothiazolone derivative was obtained by carrying out the same operation as above. The structural formula, yield, melting point and elemental analysis values of this product are shown in Table 1.

7-', ' Examples 1 to 3 and Comparative Examples 1 and 2 (controlling effect against tomato late blight) Tomato seedlings at the 4th true leaf stage (cultivar: Bonderosa) K Amount of 50 i of benzothiazolone derivative obtained in the above synthesis example L A test compound in the form of a wettable powder ( A chemical solution containing 50% active ingredient diluted with water to a predetermined concentration was sprayed over a distance of 10 m per pot. One day later, 15 spores of tomato late blight fungus (Phytophytora infestans), which had been formed on potato tubers in advance, were examined under a microscope.
The spores were suspended in water to a concentration of 20 to 30 spores per 0x field of view, and the spore suspension was dripped onto tomato leaves. After inoculation, store in a greenhouse at a humidity of 95% or higher and a temperature of 18°C to encourage disease onset.After 4 days, the plots were taken out and the disease onset was investigated, and the rate of diseased leaves (%) and control value (
%) was calculated. In addition, chemical damage to tomatoes was investigated using the following indicators. The results are shown in Table 2.

Investigation indicators for drug damage 5: Severe, 4: Severe, 3: Much, 2: Little.

1: Slight, 0: None Table 2 1: Synthesis number of the benzothiazolone derivative used 2: Average control value conducted in duplicate at 1 concentration $3: N
-) Commercially available fungicide containing lychloromethylthiotetrahydrophthalimide (generic name: cabtan) Example 4~
7 and Comparative Examples 3 and 4 (Controlling effect against rice blast) Examples 1 to 4 were applied to the fourth leaf stage seedlings of paddy rice (variety: Norin No. 29) grown in soil in a greenhouse in a clay body with a diameter of 9 c++t.
A predetermined concentration chemical solution of a hydrating powder prepared in the same manner as in 3 was sprayed at 10 ILt per pot. One day later, a spore suspension of the rice blast fungus (Bilicularia oryzae) was spray-inoculated, and the temperature was maintained at a constant temperature of 25-26°C and 95-100% humidity.
The plants were placed in a humidity chamber, and after 5 days, the severity of the disease was determined based on the lesion area ratio, and the control effect was examined. The control value (%) was calculated using the following formula. In addition, phytotoxicity to rice was investigated in the same manner as in Examples 1 to 3. The results are shown in Table 3.

/゛- 3rd table rate 1. *2: Same book as Table 2 3. Fungicide containing 20-ethyl-S,S-diphenylphosphorodithioate (common name: EDDP) Examples 8 to 12 and Comparative Examples 5 and 6 (barley udon) Disease control effect) A predetermined concentration chemical solution of a hydrating powder prepared in the same manner as in Examples 1 to 3 was applied to the first true leaf stage seedlings of barley (cultivar: Kashimagi) cultivated in soil in a plastic pot with a diameter of 7 cm. After spraying 5 IILt per pot and leaving it for 24 hours, powdery mildew (Erysiphaegraminos) spores were sprinkled on the pot. After inoculation, the seeds were kept at 18°C, and after 7 days, the disease severity was determined by the percentage of lesion area, and the control effect was examined. The control value (%) was calculated using the same criteria as in Examples 4 to 7, and the chemical damage to barley was based on the same criteria as in Examples 1 to 3. The results are shown in Table 4.

Table 4 Ne1: Same as Table 1

Claims (5)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, and R^2 represents -COR^
3, -CONHR^4 or -SO_2R^4 (here, R^3 represents a cycloalkyl group having 3 to 6 carbon atoms, and R^4 represents an alkyl group having 1 to 4 carbon atoms or an alkyl group having 2 to 4 carbon atoms. (indicates an alkenyl group). ] A benzothiazolone derivative represented by (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms. ] to the nuclear-substituted benzothiazolone represented by the general formula R^3COX [where R^
3 represents a cycloalkyl group having 3 to 6 carbon atoms, and X represents a halogen atom. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting acid halides represented by ▼ [In the formula, R^1 and R^3 are the same as above. ] A method for producing a benzothiazolone derivative represented by (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms. ] to the nuclear-substituted benzothiazolone represented by the general formula R^4NCO [where R^
4 represents an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms. ] A method for producing a benzothiazolone derivative represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^4 are the same as above]. (4) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms. ] to the nuclear-substituted benzothiazolone represented by the general formula R^4SO_2X [wherein,
R^4 is an alkyl group having 1 to 4 carbon atoms or an alkyl group having 2 to 4 carbon atoms
4 represents an alkenyl group, and X represents a halogen atom. ]
A method for producing a benzothiazolone derivative represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^2 and R^4 are the same as above], which is characterized by reacting a sulfonyl halide represented by the above formula. (5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, and R^2 represents -COR^
5, -CONHR^4 or -SO_2R^4 (here, R^3 represents a cycloalkyl group having 3 to 6 carbon atoms, and R^4 represents an alkyl group having 1 to 4 carbon atoms or an alkyl group having 2 to 4 carbon atoms. (indicates an alkenyl group). ] An agricultural and horticultural fungicide containing a benzothiazolone derivative represented by the following as an active ingredient.