JPS6041066B2 - Benzoxazolone derivatives and agricultural and horticultural fungicides containing them - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to new benzoxazolone derivatives and their use as agricultural and horticultural fungicides. More specifically, the penzoxazolone derivatives represented by the general formula [1]: (wherein R. and R2 represent a lower alkyl group or a chlorine atom, and R3 represents a lower alkenyl group or a lower alkenyloxy group) and their effective The present invention relates to an agricultural and horticultural fungicide which is characterized by containing it as an ingredient. The present inventors synthesized a large number of penzoxazolone 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 fungi and bacteria, and have wide applicability as fungicides for agriculture and horticulture. For example, when used on paddy rice, it can control rice blast, rice sesame leaf blight, rice sheath blight, and rice white leaf blight. 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 charcoal blight, cucumber vine split disease, It can effectively control Chinese cabbage rot. Also, as a seed disinfectant, it is highly effective against rice baka-nae disease and rice sesame leaf blight. 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. It has been known from West German Patent Nos. 1,023,627 and 1,147,007 that 4,5,7-trichlorobenzoxazolone and the like can be used as industrial antibacterial and fungicides. It is also known from Soviet Patent No. 32801 that 4,5,6-trichlorobenzoxazolone has bactericidal properties. In addition, 4,5,6-trichlorobenzoxazolone in which R in the general formula [1] is substituted with a penzoyl group is used as a fungicide for agricultural and horticultural purposes such as rice blast, soybean blight, and cucumber anthracnose. is known from Hakamako No. 40-23519. However, the 5,6,7-trisubstituted penzoxazolone derivative according to the present invention is not disclosed in any of the above-mentioned publications and is a novel compound that has not been described in any literature. Furthermore, the bactericidal activity of the penzoxazolone derivative of the present invention is as described in 4.
5,7-trichlorobenzoxazolone derivative and 4
, 5,6-trichlorbesozoxazolone derivatives. This new knowledge was obtained by substituting three substituents at the 5, 6, and 7-positions of the benzene ring of penzoxazolone, and no one could have achieved it based on conventional technology. It is something. The compound of the present invention can be produced by the following reaction formula [a] or [b]. Reaction formula [a] General formula

In [0], R,, R2 and R3 have the same meanings as above. The compound of formula [D] can be easily produced by known methods from ortho-aminophenols substituted with the corresponding R, R2 and CI. In the general formula [Machi], A and B are the same or different and represent a halogen atom, an alkoxy group, a haloalkoxy group, an alkylthio group, or an ami/group. Examples of these compounds include phosgenes such as phosgene and diphosgene (trichloromethylchloroformate); Examples include formates, halothiol formates, carbonic acid esters, and urea. Reaction formula [a]
is usually

A two-step process in which the compound HA or HB is eliminated by the reaction between the compound of formula [0] and the compound of formula [m] to produce an intermediate, and the compound HB or compound HA is further eliminated to produce a compound of formula [1]. It can be considered a reaction. Therefore, depending on the type of compound of formula [m], a stable intermediate can be isolated, and after isolation, it is cyclized to [1
] Compounds of the formula may also be produced. Also, this stable intermediate

It is also possible to synthesize and cyclize by another route, without relying on the reaction of the compound of the formula [0] and the compound of the formula [m]. Reaction formula [
In a]

When reacting a compound of formula [0] with a compound of formula [dish], it is not necessary to use a solvent, but it is usually preferable to use an organic solvent.
A compound of formula m] 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 [m]
It is advisable to select it appropriately depending on the type of compound of the formula. Depending on the compound of formula [m] 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 the completion of the reaction, if an acid binder is used, the salts of the acid binder precipitated in the reaction solution are separated in a furnace, and the solvent is distilled off from the furnace solution to obtain the compound of the present invention. In some cases, it can 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 Example 1. Reaction formula [b] In the compound of formula [W], R and R2 have the same meanings as above. The compound of the formula [W] is formed by the reaction formula [a
It can be manufactured according to the method shown in ]. Further, in the compound of formula [V], R3 has the same meaning as above, and Y represents a halogen atom. These compounds include alkenyl halides and alkenyl haloformates, all of which can be easily produced by methods known per se. Reaction formula [
In b], when reacting the compound of formula [W] and the compound of formula [V], 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 formula [V] itself may be used as a solvent. Examples of organic solvents that can be used include hydrocarbons, halogen-substituted hydrocarbons, ethers, esters, ketones, acid amides, alcohols, and dimethyl sulfoxide. As acid binders, 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 better to heat the reaction. Although the reaction time is not constant depending on the compound of formula [V] used, the solvent, the reaction temperature, etc., the reaction is completed in a short time when a polar solvent is used. After the reaction is completed, the salts of the acid binder suspended in the reaction solution are separated by a furnace, and the solvent of the reaction 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. Example 2 shows a production example of the compound of the present invention according to reaction formula [b]. Examples of manufacturing the compounds of the present invention are shown below. Example 1 Compound No. Preparation of 3-chloro-6-acryloylamino-2,4-xylenol synthesized from 3-chloro-6-amino-2,4-xylenol and acryloyl chloride.
In a round bottom flask with a volume of 0.00, add 2.
7.6 hours and 150M of toluene was added. Then, phosgene was introduced on the evening of 9.9 while holding a light ceremony under ice water cooling. Thereafter, the mixture was heated and refluxed for 1 hour. After the reaction solution was cooled, it was transferred to a separatory funnel with a capacity of 500 ml, to which 150 ml of tetrahydrofuran and 150 ml of water were added, and the organic layer was separated. After drying this with molasses, the solvent was removed under reduced pressure to obtain yellow crystals. When this is recrystallized from acetone, N-acryloyl 5,7
-Dimethyl-6-chlorobenzoxazolone was obtained as yellow-white crystals in an amount of 20.4 hours. Melting point is 161-1
It was 63q○. Example 2 Compound No. Preparation of 2 6-amino 2,3,4 in a round bottom flask with a capacity of 300
- 21.3 m of trichlorophenol, 27.6 m of anhydrous potassium carbonate and 150 m of toluene were added, and 9.9 m of phosgene was introduced while cooling with ice water. Thereafter, the mixture was heated and refluxed for 1 hour. Cool the reaction solution and
Transferred to a separatory funnel of 00M capacity, add 150 volumes of tetrahydrofuran and 150 volumes of water, separate the organic layer, dry with reed salt, and distill off the solvent under reduced pressure to obtain 5.
6,7-Trichlorobenzoxazolone was obtained as yellowish-white crystals in an amount of 23.4 hours. This thing is meta/-
When it was recrystallized from a mixed solvent of alcohol and acetone, it became white crystals with a melting point of 253-254°. Next, the crystals were placed in a round bottom flask with a capacity of 300 kg, and 1 part of acetone was added.
50 units and 12.0 units of allyl chloroformate were added. Then, 10.1 minutes 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 mixture, the precipitated salt was chopped in a furnace and the furnace liquid was concentrated to obtain yellow crystals. When this product is recrystallized from acetone, N-allyloxycarponyl-5,6
, 7-trichlorobenzoxazolone was obtained as yellow-white crystals in an amount of 27.4 hours. The melting point was 96-98°C. Table 1 shows the compounds of general formula [1] produced according to the above examples. In addition, compound numbers are also referred to in the following Test Examples and Examples. Table 1 Compound No. Structural formula
Melting point (℃) In order to use the compound of the present invention as an agricultural and horticultural fungicide, the compound of the present invention may be used as it is or diluted with a liquid carrier such as water or an organic solvent, a solid powder, or other suitable carrier. If necessary, add auxiliary agents such as wetting agents, spreading agents, dispersants, emulsifiers, and fixing agents to produce wettable powders, liquids, emulsions, sol, powders (including DL type powders), fine granules, and granules. It can be used in formulations such as As the liquid carrier used in formulation, for example, solvents such as water, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, esters, ketones, acid amides, and dimethyl sulfoxide can be used. Further, as the solid carrier, mineral powders such as clay, talc, kaolin, bentonite, silicate powder, calcium carbonate, and silicic acid, wood flour, and other organic powders can be used. As adjuvants, nonionic, anionic, enteric ionic and amphoteric surfactants, ligninsulfonic acid or its salts, gums, aliphatic salts, glues such as methyl cellulose can be used. Furthermore, when using the compound of the present invention as a fungicide for agriculture and horticulture, it is possible to expand its applicability by mixing it with insecticides, fungicides, herbicides, plant growth regulators, etc., and in some cases, a synergistic effect may be obtained. You can also hope for it. Such other agricultural and horticultural fungicides include, for example, 3,3'-
Ethylenebis(tetrahydro-4,6-dimethyl-2H
-1,3,5-thiadiazine-2-thione: ethylene bisdithiocar/dimate zinc salt or manganese salt; bis(dimethyldithiocarbamoyl) disulfide: propylene bisdithiocarbamate zinc salt: bis(dimethyldithiocarbamoyl)ethylenediamine; dimethyldithio Carbamate nickel salt; Methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate:
1,2-bis(3-methoxycarponyl-2-thioureido)benzene; 1-isopropylcarbamoyl-3-(3,5-dichlorophenyl)hydantoin; N-hydroxymethyl-N-methyldithiocarbamate potassium salt; 5-methyl- 10-butoxycarbonylamino-
Carbamate fungicides such as 10,11-dehydrodibenzo(b,f) azevin, bis(1-hydroxy-2(I)
H) Pyridine thionate) Zinc salt: Pyridine fungicides such as 2-pyridinethiol-1-oxide sodium salt, 0,0-diisopropyl-S-benzylphosphorothioate; ○-ethyl-S,S-diphenyldithiophosph Phthalimide fungicides such as N-(2,6-diethylphenyl) phthalimide; N-(2,6-diethylphenyl)4-methylphthalimide;
N-trichloromethylthio-4-cyclohexene-1,
2-dicarboximide; N-tetrachloroethylthio-
4-sik. Dicarboximide fungicides such as hexene-1,2-dicarboximide, 5,6-dihydro-2-methyl-1,4-oxatiso-3-carboxanilide 4,
4-dioxide; 5,6-dihydro-2-methyl-1,
Oxatine fungicides such as 4-oxane-3-carboxanilide, 2,3-dichloro-1,4 naphthoquinone, 2
-Oxy-3-chloro-1,4-naphthoquinone Naphthoquinone fungicides such as copper sulfate, bentachlornitrobenzene; 1,4-dichloro-2,5-dimethoxybenzene; 5-methyl s-triazole (3,4-b)penzthiazole; 2 -(thiothia/methylthio)penzothiazole; 3-hydroxy-5-methyl inxazole; N-2,3-dichlorophenyltetrachlorophthalamic acid: 5-ethoxy-3-trichloromethyl-1,
2,4-thiadiazole; 2,4-dichloro-61 (o
-Chloranilino)-1,3,5-triaziso; 2.3
-dicyano-1,4-dithioanthraquinone; 8-oxyquinoline steel: polyoxine; validamycin; cycloheximide; methanalsonic acid iron salt; diisopropyl-1,3-dithiolane-2-ylidenemalonate; 3-
Allyloxy-1,2-penziisothiazole-1,1
-dioxide; Kasugamycin; Blasticidin S;
4,5,6,7-tetrachlorphthalide; 3-(3,5
N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-
Dicarboximide; S-n-butyl-5'-para-t
-Butylbenzyl-N-3-pyridyldithiocarbonimidate; 4-chlorophenoxy-3,3-dimethyl 1
-(IH,1,3,4triazole-1-yl)-2
-butanone; methyl 1○, L-N-(2,6-dimethylphenyl)-1N-(2-methoxyacetyl)alaninate; N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl [Imidazole-1-carpoxamide; N-(3,5-dichlorophenyl)succinimide; Tetrachloroisophthalonitrile; 2-dimethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine; 2,6-dichloro-4-nitroaniline ;
3-Methyl-4-chlorobenzthiazol-2-one:
1,2,5,6-Tetrahydro Mountain H-pyrrolo [3,
2,1-i,j] quinolin-2-one; 3'-isopropoxy 2-methylbenzanilide; 1-[2-(2,
1,2-benzisothiazolin-3-one: Basic copper chloride; Basic sulfuric acid steel: N'-dichlorofluoromethylthio N,N-dimethyl-N-phenylsulfamide, ethyl-N-(3-dimethylaminopropyl)thiocarbamate hydrochloride: Piomycin: S,S-6-methylquinoxaline-2, 3-diyldithiocarbonate; complex obzinc and maneb (
Complex of zincandma fertilizerb); bis(
Disinfectants such as ethylene bis(dithiocarbamic acid) dizinc;
It is not limited to these. The agricultural and horticultural fungicide of the present invention can also be used in combination with the following plant growth regulators, herbicides, or insecticides. Isourea-based plant growth regulation such as N'-methoxycarponyl-N'-4-methylphenylcarbamoylethylisourea, 1-(4-chlorophenylcarbamoyl)-13-ethoxycarponyl-2-methylisourea agent, sodium naphthalene acetate; 1,2-dihydropyridazine-3,6-dione; plant growth regulators such as gibberellin, 2-methylthio-4,6-bisethylamino-1,3,5-
Triazine: 2-chloro-4,6-bisethylamino-1,3,5-triazine: 2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine; 2-chloro-4-ethylamino-6-isopropylamino- s-triazine; 2-methylthio-4,6-bis(isopropylamino)-s-triazine; triazine herbicides such as 2-methylthio-4-ethylamino-6-isopropylamino-s-triazine, 2,4-dichlorophenoxyacetic acid and Methyl, ethyl or butyl ester thereof: 2-chloro-4-methylphenoxyacetic acid; phenoxy herbicides such as 4-chloro-2-methylphenoxyacetic acid, ethyl 2-methyl-4-chlorophenoxybutyrate, 2,4,6-trichlorophenyl- 4'-
Diphenyl ether herbicides such as nitrophenyl ether; 2,4-dichlorophenyl-4'-nitrophenyl ether; 3,5-dimethylphenyl-4-nitrophenyl ether, 3-(3 ,4-dichlorophenyl)-1
-methoxy-1-methylurea; 3-(3,4-dichlorophenyl)-1,1-dimethylurea; urea-based herbicides such as 3-(4-chlorophenyl)-1,1-dimethylurea; 3-methoxycarbonylaminophenyl-N-(
3-methylphenyl)carbamate; isopropyl-N
-(3-chlorophenyl)carbamate; methyl-N-
Carbamate herbicides such as (3,4-dichlorophenyl)carbamate, 5-from-3-sec-butyl-6
- Methyluracil; uracil herbicides such as 1-cyclohexyl-3,5-propylene uracil, S-(4-chlorobenzyl) N,N-diethylthiol carbamate;
S-ethyl-N-cyclohexyl-N-ethylthiol carbamate; S-ethyl-hexahydro IH-azepine-1-carbothioate; S-ethyl-N,N-dinormalf. Thiol carbamate herbicides such as lopyl thiocar/dimate, pyridinium salt herbicides such as 1,1'-dimethyl-4,4'-bispyridinium dichloride, N-(
Phosphorus herbicides such as phosphonomethyl)glycine, Q, Q,
Q-trifluoro2,6-dinitro N,N-dipropyl-p-toluidine; 4-(methylsulfonyl)2,
6-dinitro-N,N-dipropylaniline; N3. N
Aniline herbicides such as 3-diethyl-2,4-dinitro-6-trifluoromethyl-1,3-phenyldiamine, 2-chloro-2',6-diethyl-N-(butoxymethyl)acetanilide;2-chloro-2',6'-diethyl-N-(methoxymethyl)acetanilide; 3,4
-Acid anilide herbicides such as dichloropropionani 1', 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole; 1,3-dimethyl-4-(2, Pyrazole herbicides such as 4-dichlorobenzoyl)-5-(p-toluenesulfonyloxy)pyrazole, 5-tert-butyl-3-(2,4-dichloro-5-impropoxyphenyl) 1,3,4 -Oxadiazolin-2-one; 2-[N-isopropyl, N-
(4-chlorphenyl)rubamoyl]-4-chlor-
5-Methyl-4-isoxazolin-3-one; 3-isopropylbenzo-2-thia-1,3-diazinone-
(4)-2,2-dioxide; Herbicides such as 3-(2-methylphenoxy)pyridazine, 0,0-jethyl○-(
2-isopropyl-4-methyl-6-pyrimidinyl) phosphorothioate;○,0-diethyl S-2-[(ethylthio)ethyl]phosphorodithioate;○,0-dimethyl○1-(3-methyl-4-nitrophenyl) thiophosphate;○, 0-dimethyl S-(N-methylcarbamoylmethyl) phosphorodithioate; ○,0-dimethyl S-(N-methyl-N-formylcarbamoylmethyl)
Phosphorodithioate;○,0-dimethyl S-2-(ethylthio)ethylphosphorodithioate;0,0-diethyl S-2[(ethylthio)ethyl]phosphorodithioate;0,○-dimethyl-1-hydroxy-2 ,2,2
-Trichloroethylphosphonate;○,0-diethyl○-(5-phenyl-3-isoxazolyl)phosphorothioate;○,0-dimethyl0-(2,5-dichloro-
4-Fromophenyl)phosphonothioate;○,0-dimethyl-0-(3-methyl-4-methylmercaptophenyl)thiophosphate;○-ethyl-○-p-cyanophenyl phenylphosphonothioate;○,0-dimethyl S-( 1,2-dicarboethoxyethyl)phosphorodithioate; 2-chloro(2,4,5-trichlorophenyl)vinyldimethyl phosphate; 2-chloro(2,4-dichlorophenyl)vinyldimethyl phosphate ; ○,0-dimethyl ○-p-cyanophenol phosphorothioate; 2,2-dichlorovinyl dimethyl phosphate; ○,0-diethyl ○-2,
4-dichlorophenyl phosphorothioate; ethyl
Merkaf. Tophenylacetate ○,0-dimethyl
Phosphorodithioate; S-[(6-chloro-2-oxo-3-benzoxazolinyl)methyl]○,0-diethylphosphorodithioate; 2-chloro-1-(2,4
-dichlorophenyl)vinyl diethyl phosphate;
○,○-diethyl○-(3-oxo-2-phenyl-
2-pyridazin-6-yl) phosphorothioate;○
,0-dimethyl S-(1-methyl-2-ethylsulfinyl)-ethylphosphorothioate;○,0-dimethyl S-phthalimidomethylphosphorodithioate;○,
0-Diethyl S-(N-ethoxycarbonyl-N-methylcarbamoylmethyl)phosphorodithioate; ○,
0-Dimethyl-S-[2-methoxy-1,3,4-thiadiazole-5-(4H)-onyl(4)-methyl]
Dithiophosphate; 2-methoxy-4H-1,3,2
-penzodioxaphosphorine 2-sulfide;○,0-
Diethyl-1(3,5,6-trichloro-2-pyridyl)phosphorothioate;○-ethyl-2,4-dichlorophenylthionobenzene phosphonate;S-[
4,6-diamino-s-triazin-2-ylmethyl]○,0-dimethyl phosphorodithioate;○-ethyl○-p-nitrophenylphosphonothioate;○,
S-dimethyl-N-acetyl phosphoroamidothioate; 2-diethylamino-6-methylpyrimidine-4-yl-diethylphosphorothionate; 2-diethylamino-6-methylpyrimidin-4-yl dimethylphosphorothioate; ○, 〇 -diethyl ○-p-(methylsulfinyl) phenyl phosphorothioate; ○-ethyl-S-propyl ○-2,4-dichlorophenyl phosphorodithioate; cis-3-(dimethoxyphosphinoxy)-N- Phosphorous insecticides such as methyl-cis-crotonamide, 1-naphthyl N-methylcarbamate; S-methyl-N-[methylcarbamoyl)oxy]thioacetimidate: m-tolyl methylcarbamate; 3,4-
Xylyl methyl carbamate; 3,5-xylyl methyl carbamate; 2-sec-butylphenyl-N-methyl carbamate; 2,3-dihydro 2,2-dimethyl-7-penzofuranyl methyl carbamate; 2-
Isopropoxyphenyl-N-methyl carbamate; 1
, 3-bis(bamoylthio)-2-(N,N-dimethylamino)propane hydrochloride: 2-jethylamino-6-methylpyrimidin-4-yl Carbamate insecticides such as dimethylcarbamate, N,N- Dimethyl-N'
-(2-Methyl-4-chlorophenyl)formamidine hydrochloride, nicotine sulfate, milbemycin, 6-methyl-2,3-quinoxaline dithiocyclic S,S-
Dithiocarbonate, 2,4-dinitro 6-sec-butylphenyl dimethyl acrylate; 1,1-bis(p-chlorophenyl) 2,2,2-tric. ethanol: 2-(p- to rt-butylphenoxy) isof.
Lopyl-2'-chloroethylsulfite;azoxybenzene; di(p-chlorophenyl)-cyclopropyl carbinol: di[tri(2,2-dimethyl-2-phenylethyl)tin]oxide; 1-(4-chlorophenyl)-3(2 , 6-difluorobenzoyl)-urea;S-tricyclohexyltine ○,0-Diisopropylphosphorodithioate or other insecticides or fertilizers can be used in combination. Examples of the agricultural and horticultural fungicide of the present invention will be shown next, but the present invention is not limited to these examples. Note that parts in the examples indicate parts by weight. Example 3 Emulsion compound no. 2 parts of the compound of Example 1, 3 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 4 Sol preparation Compound No. 1 pulverized to less than 10 mm. 4 parts of compound 2,
2 parts of lauryl sulfate, 2 parts of sodium alkylnaphthalesulfonate, 1 part of hydroxypropyl cellulose and 55 parts of water were uniformly mixed to obtain a sol containing 40% of the active ingredient. Example 5 Wettable powder compound M. A wettable powder containing 20% of the active ingredient was obtained by uniformly pulverizing and mixing 2 parts of compound 1, 5 parts of boroxyshetylene alkylaryl ether, 3 parts of calcium lignosulfonate, and 7 parts of diatoms. . Example 6 Powder Compound Snake. 3 parts of compound No. 2, 0.5 part of lotus anhydride fine powder,
0.5 part of calcium stearate, 50 parts of clay, and 46 parts of turk were uniformly mixed and ground to obtain a ground product containing 3% of the active ingredient. Example 7 Granule Compound No. 5 parts of the compound No. 2, 1 part of calcium lignin sulfonate, 3 parts of bentonite and 64 parts of clay were uniformly mixed and pulverized, water was added and granulated, and after drying, the grains were separated to obtain granules containing 5% of the active ingredient. Obtained. Test Example 1 Rice Sesame Leaf Blight Control Effect Test Water prepared according to Example 5 was applied to fourth-leaf stage seedlings of paddy rice (variety Asahi) grown in clay pots with a diameter of 9 skins in a greenhouse. A predetermined concentration of the Japanese preparation was sprayed, and one day later, a conidial suspension of the rice sesame leaf blight fungus was inoculated by spraying. Five days after inoculation, the number of rice and sesame straw blight spots per fourth leaf was investigated, and the control 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. Control value = (・Number of leaf blight and blight disease in the vertical spray area) x 100 Investigation index of chemical damage 5: Severe, 4: Severe, 3: Much, 2: Little , 1: Slight, 0: None Table 2 Paddy rice and rice blight control effect) G Note) (West German Patent No. 1,023,627) (West German Patent No. 1,147,007) -2351 Small) (Special Publication No. 40-2351y) Triazine: (Commercial product) Test Example 2 Rice blast control effect test Paddy rice (variety Asahi) cultivated in a clay pot with a diameter of 9 skins in a greenhouse. ) was sprayed with a predetermined concentration solution of a hydrating powder prepared according to Example 5. Then overnight in greenhouse 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. In addition, chemical damage to rice was investigated in the same manner as in Test Example 1. The test was conducted using 1 concentration and 2 lotions. The results are shown in Table 3. Control value = (-Number of sardines and sea breams) No. 3 cultivated in soil in clay pots
Tomato seedlings (variety: World No. 1) at the true leaf stage were sprayed with a predetermined concentration of a hydrating powder solution prepared according to Example 5, 10 times per pot. One day later, the spores of tomato late blight fungus (Phytophysora infestans), which had been formed on the potato tubers in advance, were suspended in sterile water to a concentration of 20 to 30 spores per 15 pm field of view under a microscope. The spore suspension was drip-inoculated onto tomato plants. After inoculation, the plants were stored in a damp room at 20:00 to encourage the onset of disease, and after 3 days they were taken out to investigate the onset of disease in the sprayed plots, and the rate of diseased chestnuts (%) and control value (%) were determined from the following formula. In addition, phytotoxicity to tomatoes was investigated according to the standards of Test Example 1 and the same machine. Disease incidence rate = Kirijin Kaoruai ×・〇. Control value = (1 - non-sprayed area area diseased hollyhock rate) XIO. The test was conducted using 1 concentration and 2 lotuses, and the average control value was calculated. The results are shown in Table 4. Table 4 (Tomato late blight control effect) Q8: Test example 4 Cucumber downy mildew control effect test First true leaf stage cucumber seedlings grown in a greenhouse using clay pots with a diameter of 9 arcs (variety: Sagami Hanjiro) 1 drop of a predetermined concentration of a hydrating powder solution prepared according to Example 5 was applied to the underside of the leaves.
I sprayed 10 seeds per pot. One day later, the spores of cucumber downy mildew fungus (Pseudoveronospora cuvensis), which had been spore-formed on the cucumber leaves in the disease room, were added to the spores using Tween 20 ( The leaves were 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 inoculate the undersides of leaves on which the chemical had been sprayed. After inoculation, the plants were kept in a greenhouse at 20 oo for 2 hours, and then stored in a disease-infecting room in a humid room at 24 q0 to encourage disease onset. After 6 days of storage, it was removed and the lesion area ratio was investigated, and the control value (
%) was calculated. In addition, chemical damage to the Kyu River was investigated using the same criteria as in Test Example 1. The test was conducted using 1 concentration and 2 lotuses, and the average control value was calculated. The results are shown in Table 5. Control value = (1 - number of lesions and area accumulation ratio of non-sprayed area) XI. 〇Table 5 (Cucumber downy mildew control cross fruiting) Test example 5 Cucumber anthrax disease control effect test No. 1 cultivated in soil in a clay pot with a diameter of 9 arcs in a greenhouse
A solution of a predetermined concentration of a hydrating powder prepared according to Example 5 was applied to young cucumber seedlings (variety: Sagami Hanshiro) at the true leaf stage at a concentration of 10% per pot.
It was sprayed in an amount of '. One day later, 1 hour was prepared at 24 qo on the ground in an oatmeal agar tower.
The spores of the cucumber charcoal stain bacterium (Colletotrichum lagenarium) obtained by culturing for 0 days were suspended in sterilized water containing 50 ppm of Kween 20 so that the spore concentration per field of view of 150 people's microscopes was about 10 spores. It was spray inoculated onto the leaves sprayed with the chemical. After that, they were kept in a humid room at 25:00 for 24 hours, and then stored in a greenhouse at 24:00 to encourage the onset of disease. 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. Control value = (1 - number of lesions in non-sprayed area) x. 〇Also, chemical damage to Kyu River 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 results are shown in Table 6.
Table 6 Cucumber Powdery Mildew Control Table) Oil TPN: Test Example 6 Cucumber Powdery Mildew Control Efficacy Test Cucumbers grown in soil in clay pots with a diameter of 9 cm in a greenhouse (variety: Sagami Hanshiro) A predetermined concentration of the test chemical prepared according to Example 5 was sprayed on the first chestnut-stage seedlings of 1.), and the next day, the powdery mildew spore suspension was spray-inoculated. Ten days after inoculation, 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 results are shown in Table 7. Control value = (・- ratio of disease and stagnation on the non-sprayed area) X・o. Table 7 (Cucumber Powdery Mildew Disease) Dimethylimole dimethyrimol: Test Example 7 Antibacterial activity test against various plant pathogenic bacteria The test was carried out by the agar dilution smear method (streak method). In other words, for filamentous fungi, potato decoction toji (pH 5.8
), and for bacteria, bouillon agar (pH 7.
The spore suspension obtained by adding sterile water to each test microorganism cultured in advance on a test tube slant medium in step 0) was streaked onto the drug-containing medium using a platinum loop. After culturing for 4 hours at 24°C for filamentous fungi and 2800°C for bacteria, the presence or absence of growth of each fungus was examined, and the minimum drug concentration in the medium required to completely inhibit the growth of fungi (minimum growth inhibition) was determined. Concentration Buddha evening/desk') was calculated. The results are shown in Table 8. Table 8 Examples of antibacterial activity tests against various plant pathogenic bacteria 8 Rice sheath blight control effect test A chemical solution of a prescribed concentration was sprayed on 6-leaf stage seedlings cultivated in soil using clay pots with a diameter of 9 to 40 cm per 3 pots. and left it in a glass room. In order to inoculate the diseased bacteria, one day after spraying the chemical solution, the bacterial flora that had been cultured in advance (4 hours at 270) on a potato agar medium for adding rice bran was grown in a diameter of 5 mm.
An agar disk punched out with a side cork polar was attached to the second leaf sheath and kept in a greenhouse overnight. To investigate the onset of disease, the length of the lesion per stem was investigated 4 days after inoculation, and the control value was determined by comparing it with the unsprayed area. The test results are shown in Table 9.
Control value (%) Lesion length in non-sprayed area - Disease length of sprayed area X 8 x 10O Table 9 Lesion length in non-sprayed area

Claims (1)

[Claims] 1 General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 and R_2 represent a lower alkyl group or a chlorine atom, and R_3 represents a lower alkenyl group or a lower alkenyloxy group.) A benzoxazolone derivative represented by 2 General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 and R_2 represent a lower alkyl group or a chlorine atom, and R_3 represents a lower alkenyl group or a lower alkenyloxy group.) Benzoxazolone derivative represented by An agricultural and horticultural fungicide characterized by containing as an active ingredient.