JPS6058915B2 - Benzoxazolone derivatives - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel benzoxazolone derivatives and their use as agricultural and horticultural fungicides.

More specifically, the general formula [I] (wherein X represents a lower alkyl group, Y represents a halogen atom, m and n each represent an integer of 1 or more, and m+n = 2 to 4, and R is Hydrogen atom, alkyl group, alkylcarbonyl group, haloalkylcarbonyl group, alkoxycarbonyl group, mono- or dialkylaminocarbonyl group,
The present invention relates to benzoxazolone derivatives represented by an alkylsulfonyl group or a phenylsulfonyl group, or a benzoyl or phenylaminocarbonyl group which may be substituted, and agricultural and horticultural fungicides containing these as active ingredients.

Until now, it has been reported that benzoxazolone derivatives can be used as agricultural and horticultural fungicides, for example, in Japanese Patent Publication No. 40-235 Rei, Japanese Patent Publication No. 45-1575 Wani, Japanese Patent Publication No. 124264/1982, and Japanese Patent Publication No. 55-2621. It is known in

However, some of the compounds described in these publications are effective against rice blast fungi and certain types of industrial deteriorating bacteria, but their bactericidal activity is weak and their bactericidal spectrum is narrow. The present inventors synthesized a large number of benzoxazolone derivatives and conducted extensive studies on their practicality in order to develop a disinfectant with low toxicity, excellent safety, and versatility.

As a result, it has been found that the novel benzoxazolone derivative represented by the general formula [1] has extremely excellent properties as a fungicide for agricultural and horticultural use. That is, these compounds have strong antibacterial activity against various filamentous fungi and bacteria, and have wide applicability as agricultural and horticultural fungicides. For example, when used on paddy rice, rice blast, sesame leaf blight, rice leaf blight, etc. can be controlled. In addition, when used in the fruit horticulture field, pear black spot, grape late rot, tomato leaf mold, tomato late blight, kidney bean sclerotium, cucumber powdery mildew, cucumber downy mildew, cucumber anthracnosis, and cucumber vine split disease , Chinese cabbage soft rot, etc. can be effectively controlled. Also, as a seed disinfectant, it is highly effective against rice baka-nae disease, rice sesame leaf blight, etc. In addition, these series of compounds have a strong antibacterial effect, but they are extremely excellent fungicides that can be safely used without causing any phytotoxicity to useful plants, and are not toxic to animals or fish. The compound of the present invention can be produced by the following reaction formula [a], [b] or [c].

Moreover, some compounds can also be produced by the method of reaction formula [d]. In the general formula [■], R, . X,.
Y,. m and n have the same meanings as above.

These compounds are 3For example, when R represents an acetyl group,
It can be obtained in high yield by acetylating the corresponding lower alkyl-substituted ortho-aminophenol to form lower alkyl-substituted 2-acetaminophenol by a conventional method and then halogenating it with a desired equivalent amount of halogen. In addition, by hydrolyzing the obtained compound with dilute hydrochloric acid etc. [■]
A compound is obtained in which R is a hydrogen atom. By alkylating or acylating a compound in which R is a hydrogen atom by a conventional method, various [older type compounds] can be obtained. In the general formula [■], ANBs are the same or different and represent a halogen atom, an alkoxy group, a haloalkoxy group, an alkylthio group, or an amino group. Examples of these compounds include phosgene, phosgenes such as diphosgene (trichloromethylchloroformate), haloformates, halothiolformates, carbonic diesters, urea, and the like. Reaction formula [a] usually involves the reaction between a compound of formula [■] and a compound of formula [■], in which compound HA or compound H is eliminated to produce an intermediate, and compound HB or compound Hiroshi is further eliminated to form [1]. ] can be considered as a two-step reaction to produce a compound of formula.

Therefore, depending on the type of the compound of formula [■], a stable intermediate can be isolated, and after isolation, it is cyclized to form [1].
] Compounds of the formula may also be produced. Alternatively, this stable intermediate may be synthesized and cyclized by a route other than the reaction between the compound of the formula [■] and the compound of the formula [■]. Reaction formula [a
When reacting the compound of formula [■] with the compound of formula [■] in ], it is not necessary to use a solvent, but it is usually preferable to use an organic solvent.
A compound of the formula may be used as a solvent.

As the solvent used, hydrocarbons, halogen-substituted hydrocarbons, ethers, esters, acid amides, alcohols, dimethyl sulfoxide, etc. can be used [■]
It is advisable to select it appropriately depending on the type of compound of the formula. Depending on the compound of the formula [■] used, an acid is produced during the reaction, but an acid binder may be used to make the reaction proceed smoothly. As acid binders, organic amines such as triethylamine and pyridine or inorganic bases such as potassium carbonate can be used. Although the reaction proceeds even at room temperature, the reaction can usually be completed in a short time by heating. After completion of the reaction, if an acid binder is used, the salts of the acid binder precipitated in the reaction solution are separated, and the solvent is distilled off from the bottom solution to obtain the compound of the present invention. In some cases, it may also be obtained by adding a solvent such as benzene, chloroform, ether, or tetrahydrofuran and water and then fractionating the desired product. The method for producing the compound of the present invention according to reaction formula [a] is shown in Examples 1 to 4.

In the general formula [■], R. ．． X and m are general formula [1]
has the same meaning as, Z represents a halogen atom and p is 0.1 or 2.

The compound of formula [■] can be produced according to the method shown in reaction formula [a]. As the halogenating agent, a halogen such as chlorine or bromine or sulfuryl chloride may be used alone, or a combination of hydrogen halide and an oxidizing agent such as bleaching powder, potassium chlorate or manganese dioxide can be used. Reaction formula [b
] When halogenation is carried out using a halogen such as chlorine or bromine, or sulfuryl chloride, a solvent is usually used and heating is performed to complete the reaction in a short time. In this case, water, acetic acid, halogenated hydrocarbon, etc. can be used as the solvent. In addition, when halogenating using acids such as hydrochloric acid and hydrogen bromide and an oxidizing agent, for example
(2) The compound of the formula is preferably dissolved in an acid such as hydrochloric acid, and powders such as bleaching powder, potassium chlorate, manganese dioxide, etc., or concentrated aqueous solutions thereof are added thereto. At this time, acetic acid or the like may be used as a solvent if necessary. In the halogenation, the use of iron, iron chloride, phosphorus compounds, aluminum chloride, antimony chloride, etc. as a catalyst and irradiation with ultraviolet rays are effective in smoothly proceeding with the reaction of formula [b]. After the reaction is complete, the compound of formula [1] can be obtained directly by distilling off the solvent in the reaction solution, but in some cases, benzene, chloroform, ether, tetrahydrofuran, etc. may be present in the reaction solution. It can also be obtained by adding a solvent and water and then fractionating the desired product. Reaction formula [b
Examples 5 to 7 are shown in Examples 5 to 7 of the method for producing the compound of the present invention.

In the compound of reaction formula [c] [■], X. ．． Y,. m and n have the same meanings as above.

In the compound of the formula [■], R represents a substituent other than a hydrogen atom as defined above, and D represents an atom, an alkylsulfonic acid group, or an arylsulfonic acid group. These compounds include alkyl halides, acyl halides, dialkyl sulfates, arylsulfonic acid esters, and the like, and all of them can be easily produced by methods known per se. In reaction formula [c], a compound of formula [■] and [■
When reacting with the compound of the formula [■], it is not necessary to use a solvent, but it is usually preferable to use an organic solvent, and in some cases, the compound of the formula [■] itself may be used as a solvent. Good too.

Examples of organic solvents that can be used include hydrocarbons, halogen-substituted hydrocarbons, ethers, esters, ketones, acid amides, alcohols, and dimethyl sulfoxide. As the acid binder, organic amines such as triethylamine and pyridine, or inorganic bases such as potassium carbonate can be used. Although the reaction proceeds at room temperature, it is usually best to heat the reaction. Use reaction time [■
The reaction is not fixed depending on the compound of the formula, the solvent, the reaction temperature, etc.7, but when a polar solvent is used, the reaction is completed in a short time. After the reaction is completed, the salts of the acid binder precipitated in the reaction solution are removed, and the solvent of the solution is distilled off to obtain the compound of the present invention. In some cases, the desired product can also be obtained by adding an organic solvent such as benzene, chloroform, ether or tetrahydrofuran, and water to the reaction solution and fractionating the desired product. Examples 8 to 10 show examples of producing the compounds of the present invention according to reaction formula [c].

In the compound of formula [■] and the compound of formula [■], R
'' represents an alkyl group or a phenyl group which may be substituted.

Therefore, the production method of reaction formula [d] can be used when R in general formula [1] is an alkylaminocarbonyl group or a phenylaminocarbonyl group that may be substituted. Although it is not necessary to use a solvent when reacting the compound of formula [■] with the compound of formula [■] in reaction formula [d], it is usually preferable to use an organic solvent, and in some cases A compound of formula [■] may be used as a solvent.

As the organic solvent, for example, hydrocarbons, halogen-substituted hydrocarbons, ethers, esters, ketones, etc., which do not react with the compound of the formula [■] can be used. Furthermore, when a small amount of organic amines such as triethylamine and pyridine are added as a catalyst, the reaction proceeds extremely smoothly. The reaction proceeds satisfactorily at room temperature, but may be heated in some cases. Although the reaction time depends on the compound of the formula [■] used, it is usually completed in a relatively short time. After the reaction is completed, the compound of the present invention can be obtained by removing the crystals precipitated in the reaction solution. Depending on the case, the used solvent may be distilled off. Example 11 shows an example of producing the compound of the present invention according to reaction formula [d].
It was shown to.

Example 1 Compound No. Preparation of Step 6: Put 15.8y1 of 2-amino-4-chloro-6-methylphenol, 27.6f of anhydrous potassium carbonate, and 150ml of toluene into a 300mt capacity round-bottomed flask, and introduce 9.9g of phosgene while stirring under ice-water cooling. did.

Thereafter, the mixture was heated and refluxed for 1 hour. After cooling the reaction solution, it is transferred to a 500 mt separating vessel, 150 ml of tetrahydrofuran and 150 ml of water are added, and the organic layer is separated. After drying this with Glauber's salt, the solvent was distilled off under reduced pressure to obtain brown crystals. When this product is recrystallized from a mixed solvent of hexane and acetone, 5-chloro-7-methylbenzoxazolone is obtained as yellowish brown crystals.
It was obtained in an amount of 5.6y. This thing has a melting point of 232-23
It showed 4°C. Example 2 Compound No. Preparation of 48 In a 300 ml round bottom flask, add 2-amino-3,5-
Dimethyl-4,6-dichlorophenol 21.2y1 Anhydrous potassium carbonate 27.6q and Ethyl acetate 150ml
A solution of 9.9 V of diphosgene (trichloromethyl chloroformate) dissolved in 50 ml of ethyl acetate was added dropwise with stirring under ice-water cooling, and the resulting mixture was heated under reflux for 1 hour.

The reaction solution was cooled, the precipitated salt was separated in a suction oven, and the oven solution was concentrated under reduced pressure to obtain yellow crystals. When this product was recrystallized from a mixed solvent of methanol and acetone, 4,6-dimethyl-5,7-dichlorobenzoxazolone was obtained as pale yellow crystals in an amount of 20.9y. This product showed a melting point of 271-277C. Example 3 Compound No. Preparation of 2-ethoxycarbonylamino-4-methyl-5- synthesized from 2-amino-4-methyl-5-chlorophenol and ethyl chloroformate in a 100 ml round bottom flask.
Chlorphenol 23.0y1 Dimethylformamide 5
Add 0 mt and 0.5 q of anhydrous potassium carbonate and 1
The mixture was heated and stirred at 40°C for 4 hours.

The reaction solution was cooled, 100 ml of water was added, and the precipitated crystals were collected under suction and dried with ventilation at 80° C. for 2 hours to obtain yellow crystals. When this product was recrystallized from methanol, 5-methyl-6-chlorobenzoxazolone was obtained as pale yellow crystals in an amount of 15.6V. This product showed a melting point of 182-184°C. Example 4 Compound No. 33
15.1 y of 2-amino-4-isopropylphenol and 100 mL of acetic acid were placed in a 300 ml round bottom flask, and after adding 10.2 y of acetic anhydride under ice-water cooling,
The reaction was completed by heating at 60° C. for 1 hour to obtain 2-acetamin-4-isopropylphenol.

Next, 15.6 y of chlorine gas was introduced at 80 to 90°C.
After cooling the reaction solution, acetic acid was distilled off under reduced pressure to obtain 25.7y of 2-acetamin-4-isopropyl-5,6-dichlorophenol as a brown oil.
This oil was placed in a 300 mL round bottom flask, 150 ml of tetrahydrofuran was added, and after adding 9.6 fl of sodium hydride (50%) to the resulting solution, 9.9 V of phosgene was introduced under ice-water cooling.

After stirring at room temperature for 1 hour, the reaction solution was transferred to a 500 mL separating container, 150 ml of benzene and 150 ml of water were added, and the organic layer was separated. After drying with Glauber's salt, the solvent was distilled off under reduced pressure to obtain brown crystals. When this product was recrystallized from a mixed solvent of hexane and acetone, N-acetyl-5-isopropyl-6,7-dichlorobenzoxazolone was obtained as yellowish brown crystals in an amount of 24.5y. This product showed a melting point of 133-135°C. Example 5 Compound N6. 18.4y of 5-chloro-7-methylbenzoxazolone and 150ml of acetic acid were added to a 300ml round bottom flask.
1, heated to 80-90'C and chlorine gas 7.8
Introduced y.

After the reaction was completed, acetic acid was distilled off under reduced pressure to obtain 5,6-dichloro-7-methylbenzoxazolone as yellowish brown crystals in an amount of 20.7y. Recrystallization of this product from a mixed solvent of methanol and acetone gave pink crystals with a melting point of 251-252'C. Example 6 Compound No. Preparation of 35 In a 300 ml round bottom flask, add 18.4 y of 5-chloro-7-methylbenzoxazolone and 150 ml of acetic acid.
A solution of 17.6y of bromine dissolved in 30ml of acetic acid was dropped into the solution.

Next, the reaction solution was heated to 95° C. and stirred for 4 hours, then cooled, and acetic acid was distilled off under reduced pressure to obtain reddish brown crystals. When this product was recrystallized from a mixed solvent of methanol and acetone, 5-chloro-6-bromo-7-methylbenzoxazolone was obtained as brown crystals in an amount of 22.3y. This product showed a melting point of 262-264°C. Example 7
Compound No. Preparation of 45 In a 300 mL round bottom flask, add 26.0 y of N-acetyl-4-methyl-5●7-dichlorobenzoxazolone.
Then, 150 ml of chloroform was added thereto, 16.5 y of sulfuryl chloride was added at room temperature, and the mixture was heated under reflux for 2 hours.

After the reaction was completed, the solvent was distilled off under reduced pressure to obtain yellowish white crystals. When this product is recrystallized from a mixed solvent of hexane and acetone, N-acetyl-4-methyl-5.6.
7-Trichlorobenzoxazo7ane as white crystals 2
A quantity of 3.6y was obtained. This stuff has a melting point of 125-12
It showed TC. Example 8 Compound No. Preparation of l3 In a 100ml round bottom flask, add 5●6-dichlororu7
-Methylbenzoxazolone 4.4y1 Anhydrous potassium carbonate 2.8y1 Dimethyl sulfate 2.5y and acetone 50
ml was added and heated under reflux for 2 hours.

After the reaction, the solvent was distilled off under reduced pressure and the residue was
When the precipitated crystals were filtered out, a yellowish brown crystal was obtained. When this product was recrystallized from a mixed solvent of hexane and acetone, N-methyl-5,6-dichloro-7-methylbenzoxazolone was obtained as pink crystals in an amount of 3.9 Da. This stuff has a melting point of 122-12
It showed 3°C. Example 9 Compound No. Preparation of l6 In a 100ml round bottom flask, add 5,6-dichlororu7
- 4.4 y of methylbenzoxazolone, 2.8 y of benzoyl chloride and 50 ml of acetone were added, and 2.0 y of triethylamine was added dropwise under ice water cooling.

After the dropwise addition was completed, the mixture was heated under reflux for 1 hour to complete the reaction. After cooling the reaction solution, the precipitated salt was separated and the solution was concentrated to obtain yellowish white crystals. When this product is recrystallized from acetone, N-benzoyl-5●6-dichloro-7-
Methylbenzoxazolone was obtained as white crystals in an amount of 5.5y. This product showed a melting point of 165-166°C. Example 10 Compound No. Preparation of l8 In a 100 mt capacity round bottom flask, add 5,6-dichlororu7
- 4.4V of methylbenzoxazolone, 1.9f of chloromethylformate and 50ml of acetone were added, and 2.0V of triethylamine was added dropwise under ice water cooling.

After the dropwise addition was completed, the mixture was heated under reflux for 1 hour to complete the reaction. After cooling the reaction solution, the precipitated salt was separated and the solution was concentrated to obtain yellowish brown crystals. When this product was recrystallized from a mixed solution of hexane and acetone, 4.6 f of N-methoxycarbonyl-5,6-dichloro-7-methylbenzoxazolone was obtained as pink crystals. This product showed a melting point of 135-138°C. Example 11 Compound No. Preparation of 22 In a 100ml round bottom flask, add 5,6-dichlororu7
-Methylbenzoxazolone 4.4y13-5-dichlorophenylisocyanate 3.8y and acetone 50y
ml, 3 drops of triethylamine were added, and the mixture was stirred at room temperature for 1 hour.

Crystals precipitated in the reaction solution? When you take it, the pink crystal is 7.4
obtained in the amount of y. This product was N-3.5-dichlorophenylcarbamoyl-5●6-dichloro-7-methylbenzoxazo7ine, and had a melting point of 221 to 227C. Table 1 shows representative examples of compounds of general formula [1] produced by the same method as in the above examples.

In addition, compound numbers are also referred to in the following Test Examples and Examples. In order to use the compound of the present invention as an agricultural and horticultural fungicide, the compound of the present invention can be used as is or diluted with a liquid carrier such as water or an organic solvent, a solid powder, or other suitable carrier, and moistened as necessary. Wettable powders, liquids, emulsions, sol, powders (including DL type powders), fine granules,
It can be formulated into granules and used.

Examples of liquid carriers used in formulation include water,
Aromatic hydrocarbons, aliphatic hydrocarbons, alcohols,
Solvents such as esters, ketones, acid amides, and dimethyl sulfoxide can be used. Further, as the solid carrier, mineral powders such as clay, talc, kaolin, bentonite, diatomaceous earth, calcium carbonate, and silicic acid, wood flour, and other organic powders can be used. As adjuvants, nonionic, anionic, cationic, and amphoteric surfactants, ligninsulfonic acid or its salts, gums, aliphatic salts, and glues such as methyl cellulose can be used. Furthermore, when the compound of the present invention is used as a fungicide for agriculture and horticulture, it can be mixed with insecticides, fungicides, herbicides, plant growth regulators, etc. to expand its applicability. Next, examples of the present invention will be shown, but the present invention is not limited to these examples. Note that parts in the examples indicate parts by weight.
Example 12 Emulsion compound NO. Parts of compound (a) of 17, (9) parts of dimethylformamide, 35 parts of xylene and 15 parts of polyoxyethylene alkylaryl ether were uniformly dissolved and mixed to obtain an emulsion containing 20% of the active ingredient.

Example 13 Compound No. 1 pulverized into a sol of 10μ or less 40 parts of compound 13, 2 parts of lauryl sulfate, 2 parts of sodium alkylnaphthalene sulfonate, 1 part of hydroxypropyl cellulose and 55 parts of water were uniformly mixed to obtain a sol containing 40% of the active ingredient.

Example 14 Wettable powder compound NO. Compound 2 of 29 5 parts of severely aged polyoxyethylene alkylaryl ether, 3 parts of calcium lignin sulfonate, and n parts of diatomaceous earth were uniformly ground and mixed to obtain a wettable powder containing 20% of the active ingredient.

Example 15 Powder Compound No. 3 parts of compound No. 34, 0.5 silicic anhydride fine powder
0.5 parts of calcium stearate, 50 parts of clay, and 46 parts of talc were uniformly mixed and ground to obtain a powder containing 3% of the active ingredient.

Example 16 Powder Compound No. 5 parts of the compound of No. 2, 1 part of calcium lignin sulfonate, 9 parts of bentonite, and clay? The mixture was uniformly mixed and pulverized, granulated by adding water, dried, and then sieved to obtain granules containing 5% of the active ingredient.

Test Example 1 Rice Sesame Leaf Blight Control Effect Test A hydrating agent prepared according to Example 14 on fourth-leaf stage seedlings of paddy rice (variety Asahi) cultivated in clay pots with a diameter of 9 cm in a greenhouse. A chemical solution with a predetermined concentration was sprayed, and one day later, a conidial suspension of the rice leaf blight fungus was spray-inoculated.

Five days after inoculation, the number of rice blight lesions per fourth leaf was investigated, and the removal value (%) was calculated using the following formula. In addition, chemical damage to rice was investigated using the following indicators. The test was conducted twice at one concentration, and the average control value was determined. The results are shown in Table 2. In addition, comparative drugs A to K in the table each contain the following compounds. Comparative drug A: 3
-Benzoylbenzoxazolone (Special Publication 1977)
-23519) B: 3-(4-methylbenzoyl)-6-chlorobenzoxazolone (same as above) C: 3-(4-chlorobenzoyl)-5●6-dichlorobenzoxazolone
(same as above) D: 3-(4-chlorobenzoyl)-4,5,6-trichlorobenzoyl
Sazolone (same as above)〃E: 3-(3,4-dichlorophenyl) Carbamoyl 5●6-dichlorobe
Zuoxazolone (Special Publication No. 451 157)
59)〃F: 3-(4-chloro-2-methylphenyl)carbamoyl-5-chlorobenzoxazolone (same as above)〃G: 3,4-dimethylbenzoxazolone (JP-A Shoseki-12
Compound described in No. 4264) No H:3-
Methyl-4-chlorobenzoxazolone (same as above) 〃I: 3-methyl-4-chlorobenzoxolone
Sazo Seven (described in JP-A-55-2621)
Compound) Control value Investigation index of drug damage 5: Severe, 4: Severe, 3: Much, 2: Little 1: Slight, 0: None Test example 2 Rice blast control effect test Clay pot with a diameter of 9C71 in a greenhouse A chemical solution of a predetermined concentration of a wettable powder prepared according to Example 14 was sprayed on third leaf stage seedlings of paddy rice (variety Asahi) cultivated in soil.

Then overnight under humidity and temperature conditions (humidity 95-100%, temperature 24-100%)
One day after the spraying, a spore suspension of the rice blast fungus was inoculated by spraying. Five days after inoculation, the number of rice blast lesions per leaf on the third leaf was investigated, and the control value (%) was calculated using the following formula.
) was sought. In addition, chemical damage to rice was investigated in the same manner as in Test Example 1. The test was conducted in duplicate at one concentration. The results are shown in Table 3. The comparative drug L in the table is a commercially available bactericide (general name: 1BP emulsion) containing o-0-diisopropyl S-benzyl phosphorothiolate.

Test Example 3 Tomato late blight control effect test Example 14 on third true leaf stage tomato seedlings (variety No. 1 in the world) cultivated in clay pots with a diameter of 9 CTn in a greenhouse.
1 pot of a prescribed concentration of hydrating powder solution prepared according to
Sprayed 0ml.

One day later, the spores of tomato late blight fungus (Phytophnoisola infestans) that had been formed on potato tubers in advance were suspended in sterilized water at a concentration of 20 to 3 spores per field of view at 150 f8 under a microscope. The spore suspension was drip inoculated onto tomato leaves. After inoculation, store it in a humid room at 20℃ to encourage disease onset, take it out after 3 days, investigate the onset of disease in the sprayed area, and calculate the rate of diseased leaves (%) and control value (%) using the following formula.
) was sought. Furthermore, phytotoxicity to tomatoes was investigated using the same criteria as in Test Example 1. The test was conducted twice at one concentration, and the average control value was calculated. The results are shown in Table 4. Note that the comparative drug M in the table is a commercially available fungicide (generic name: maneb) containing ethylene bis(dithiocarbamic acid) manganese. Test Example 4 Test of disease control effect on cucumber cucumber according to Example 14 on the underside of leaves of young cucumber (cultivar: Sagami Hanjiro) at the first true leaf stage, cultivated in soil in a greenhouse using clay pots with a diameter of 9 cm. A 10 ml solution of a predetermined concentration of hydrating powder prepared in the above manner was sprayed per pot.

One day later, the spores of the cucumber and the disease fungus (Pseudoperonospora kyuvensis) that had sporulated on the cucumber leaves in the disease room were removed using Tween 20 ( The mixture was washed off using a brush in ion-exchanged water containing 50 ppm of polyoxyethylene sorbitan monolaurate (polyoxyethylene sorbitan monolaurate), and used as an inoculum to spray inoculate the medicinal leaves and the underside of the leaves. After inoculation, they were kept in a humid room at 20°C for 2 hours, and then stored in a disease-infecting room in a humid room at 24°C to encourage disease onset. After 6 days of storage, it was taken out, the lesion area ratio was investigated, and the control value (%) was calculated using the following formula. Furthermore, chemical damage to cucumbers was investigated using the same criteria as in Test Example 1. The test was conducted in duplicate at one concentration.
The average control value was calculated. The results are shown in Table 5. In the table, comparative drug N is a commercially available fungicide (generic name: maneb) containing manganese ethylene bis(dithiocarbamic acid).

Test Example 5 Test for the control effect of cucumber anthracnosis
A predetermined concentration chemical solution of a hydrating powder prepared based on 4 was sprayed in an amount of 10 ml per pot.

One day later, it was incubated at 24°C on an oatmeal agar medium.
The spores of Colletotrichum lagenarium obtained by culturing for 0 days were incubated with Tween 20 so that the spore concentration per field of view under a 15CPi microscope was approximately 10C@.
The suspension was suspended in sterilized water containing 50 ppm of sterilized water, and the suspension was sprayed and inoculated onto leaves of medicinal powder. Thereafter, they were kept in a humid chamber at 25°C for 24 hours, and then stored in a humid chamber at 24°C to induce disease onset. After 6 days of storage, the leaves were taken out and the number of lesions per leaf was investigated, and the control value (%) was calculated using the following formula. In addition, chemical damage caused by creeping on cucumbers was investigated using the same criteria as in Test Example 1.

The test was conducted at one concentration twice, and the average control value was calculated. The result is as shown in the 6th garment. In addition, comparative agent 0 in the table is a commercially available disinfectant (generic name 1PN) containing tetrachloroisophthalonitrile.

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X represents a lower alkyl group, Y represents a halogen atom, m and n each represent an integer of 1 or more, and m+n =2 to 4, and R is a hydrogen atom, an alkyl group, an alkylcarbonyl group, a haloalkylcarbonyl group, an alkyloxycarbonyl group, a mono- or dialkylaminocarbonyl group, an alkylsulfonyl group or a phenylsulfonyl group, or is substituted. benzoyl or phenylaminocarbonyl group). 2. As active ingredients, there are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. 4, and R is a hydrogen atom, an alkyl group, an alkylcarbonyl group, a haloalkylcarbonyl group, an alkyloxycarbonyl group, a mono- or dialkylaminocarbonyl group, an alkylsulfonyl group or a phenylsulfonyl group, or may be substituted. An agricultural and horticultural fungicide characterized by containing a benzoxazolone derivative represented by a certain benzoyl or phenylaminocarbonyl group.