JPH0948766A - Triazolone derivative, its use and intermediate thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a triazole derivative useful as an active ingredient for plant disease injury-controlling agents. SOLUTION: This new compound, a triazolone derivative, is expressed by formula I (X is methyl or a halogen; Y and Z are each H, methyl or a halogen), e.g. 1-methyl-3-chloro-4-[2-(2-methylphenoxy)methyl-6-methylphenyl]-1,2,4- triazolone. This compound of formula I is obtained by reaction of a chlorotriazolone compound of formula II with 0.5-10 equivalents of methanol or its alkali metal salt (e.g. sodium, potassium, or lithium salt) in the presence of a base such as sodium hydroxide according as necessary, normally in a solvent such as hexane at -20 to 200 deg.C for 0.5-48h. When this compound of formula I is to be used as an active ingredient for plant disease injury- controlling agents, it is blended with a solid carrier, liquid carrier, surfactant, or other auxiliary for manufacturing preparations into a preparation such as an emulsion, hydrated agent or turbid agent, its content being pref. 0.1-95wt.%.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a triazolone derivative, its use and an intermediate for producing the same.

PRIOR ART AND PROBLEMS TO BE SOLVED BY THE INVENTION Heretofore, it has been described in WO 95/14009 that certain triazolone derivatives can be used as an active ingredient of a bactericide. It is hard to say that the compounds are not always sufficient in terms of bactericidal efficacy.

[0002]

Means for Solving the Problems As a result of intensive studies to find an excellent plant disease controlling agent, the present inventors have found that a triazolone derivative represented by the following general formula (4) shows an excellent controlling effect against plant diseases. They have found the present invention and completed the present invention. That is, the present invention is represented by the general formula

Embedded image [In the formula, X represents a methyl group or a halogen atom (chlorine atom,
Bromine atom, fluorine atom and the like), and Y and Z are the same or different and represent a hydrogen atom, a methyl group or a halogen atom (chlorine atom, bromine atom, fluorine atom and the like). ] The triazolone derivative (it is hereafter described as this invention compound) shown by these, and the plant disease control agent characterized by including it as an active ingredient.

The present invention further provides compounds of general formula 5 which are useful as intermediates for the preparation of compounds of the invention.

Embedded image [In formula, X, Y, and Z represent the same meaning as the above. ] And a chlorotriazolone compound represented by the general formula:

[Chemical 6] [In the formula, Q represents a bromine atom or a chlorine atom, and Z represents the same meaning as described above. ] The triazolone compound shown by these is also provided.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION In the compound of the present invention, the chlorotriazolone compound of the general formula 5 or / and the triazolone compound of the general formula 6, a compound in which X is a methyl group; Z is a hydrogen atom or Four
A compound which is a chlorine atom; a compound where Z is a hydrogen atom;
Compounds in which Y is a hydrogen atom, a methyl group or a chlorine atom;
Examples thereof include compounds in which Y is a hydrogen atom or a 5-methyl group.

Next, a method for producing the compound of the present invention will be described. The compound of the present invention is, for example, a chlorotriazolone compound represented by the above-mentioned general formula 5 and, on the other hand, usually 0.
5-10 equivalents of methanol or its alkali metal salt (sodium salt, potassium salt or lithium salt),
In the presence of a base, if necessary, usually in a solvent, usually at -20 ° C to
It can be produced by reacting at 200 ° C. for 0.5 to 48 hours. The solvent that can be used varies depending on the type of alkali metal salt or base used, but is, for example, hexane, heptane, ligroin, an aliphatic hydrocarbon such as petroleum ether, an aromatic hydrocarbon such as benzene, toluene, xylene, or chloroform. Halogenated hydrocarbons such as carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene, diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran,
Ethers such as ethylene glycol dimethyl ether,
Acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone and other ketones, nitroethane, nitrobenzene and other nitrates, acetonitrile, isobutyronitrile and other nitriles, pyridine,
Tertiary amines such as triethylamine, N, N-diethylaniline, tributylamine, N-methylformoline,
Formamide, N, N-dimethylformamide, N, N
Examples thereof include acid amides such as dimethylacetamide and acetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, methanol, water and the like, or a mixture thereof. Examples of the base that can be used include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Examples thereof include inorganic bases such as sodium hydride and alkali metal methoxides such as sodium methoxide. After completion of the reaction, the reaction solution is subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, further purified by chromatography, recrystallization and the like to isolate the compound of the present invention.

The chlorotriazolone compound of the general formula 5 is a compound of JH Cooley et al., J. Org. Chem. 54 , 1048-1051.
(1989) or in place of phosgene in the method, trichloromethyl chloroformate [diphosgene] or bis (trichloromethyl) carbonate [triphosgene]
Can be produced by a method using

The compound of the present invention comprises a triazolone compound represented by the general formula 6 and a compound represented by the general formula 7

[Chemical 7] [In the formula, X and Y have the same meanings as described above. ] In the presence of a base, a compound represented by
It can also be produced by reacting at 0 ° C to 200 ° C for usually 0.5 hours to 48 hours. The solvent that can be used varies depending on the raw material used, the type of base, etc., but is, for example, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, chloroform, four Carbon chloride, halogenated hydrocarbons such as dichloroethane, chlorobenzene and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone, Methanol, ethanol, isopropanol, t-butanol,
Alcohols such as octanol, cyclohexanol, methyl cellosolve, diethylene glycol and glycerin, esters such as ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate, nitration products such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile. , Tertiary amines such as pyridine, triethylamine, N, N-diethylaniline, tributylamine and N-methylformoline, acid amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide and acetamide, Examples thereof include sulfur compounds such as dimethyl sulfoxide and sulfolane, water and the like, or a mixture thereof. Examples of the base that can be used include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, and alkali metal methoxides such as sodium methoxide. In the present production method, a phase transfer catalyst such as benzyltriethylammonium chloride may be used if necessary. After completion of the reaction, the reaction solution is subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, further purified by chromatography, recrystallization and the like to isolate the compound of the present invention.

The triazolone compound represented by the general formula 6 can be produced, for example, according to the method described in Production Example 2 of the intermediate described below.

The plant diseases for which the compound of the present invention is effective include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhizoctoni).
a solani), powdery mildew of wheat (Erysiphe graminis
f.sp.hordei, f.sp.tritici), Fusarium head blight (Gibberella)
zeae), rust (Puccinia striiformis, P. graminis,
P. recondita, P. hordei), Snow rot (Typhula sp., Micron
ectriella nivalis), naked smut (Ustilago tritici, U.
nuda), eyeblight (Pseudocercosporella herpotrichoide
s), cloud disease (Rhynchosporium secalis), leaf blight (Sept.
oria tritici), wilt (Leptosphaeria nodorum), citrus black spot (Diaporthe citri), scab (Elsino)
e fawcetti), fruit rot (Penicillium degitatum,
P, italicum), apple monilia (Sclerotinia mal
i), rot (Valsa mali), powdery mildew (Podosphae)
ra leucotricha), leaf spot disease (Alternaria mali), scab (Venturia inaequalis), pear scab (Venturia)
nashicola), Black spot (Alternaria kikuchiana), Red scab (Gymnosporangium haraeanum), Peach scab (Scle
rotinia cinerea), scab (Cladosporium carpophilu)
m), Phomopsis rot (Phomopsis sp.), Black rot of grape (Elsinoe ampelina), Late rot (Glomerella)
cingulate), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), downy mildew (Plasmopara v)
iticola), oyster anthracnose (Gloeosporium kaki), leaf scab
(Cercospora kaki, Mycosphaerella nawae), Anthracnose (Colletotrichum lagenarium), powdery mildew (Sp
haerotheca fuliginea), vine blight (Mycosphacrella me)
lonis), downy mildew (Pseudoperonospora cubensis), tomato leaf spot (Alternaria solani), leaf mold (Clados)
porium fulvum), plague (Phytophthora infestans), brown leaf spot of eggplant (Phomopsis vexans), powdery mildew (Erysip)
he cichoracearum), black spot of cruciferous vegetables (Altern
aria japonica), white spot (Cercosporella brassicae),
Green onion rust (Puccicia allii), Soybean purpura (Ce
rcospora kikuchii), black spot (Elsinoe glycines),
Black spot disease (Diaporthe phaseolorum var. Sajae), anthracnose of kidney bean (Colletotrichum lindemuthianum), black spot of peanut (Cercosporidium personatum), brown spot (Cercospora arachidicola), powdery mildew of pea.
(Erysiphe pisi), Potato summer blight (Alternaria)
solani), plague (Phytophthora infenstas), powdery mildew of strawberry (Sphaerotheca humuli), rice blast of tea
(Exobasidium reticulatum), white scab (Elsinoe leucosp)
ila), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletot)
richum tabacum), sugar beet leaf spot (Cercospora bet)
icola), rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum brown spot (Septoria)
chrysanthemi-indici), white rust (Puccinia horian)
a), Botrytis cinerea of various crops,
Sclerotinia sclerotiorum, etc.

When the compound of the present invention is used as an active ingredient of a plant disease controlling agent, it may be used as it is without adding any other ingredients, but it is usually a solid carrier, a liquid carrier, a surfactant or other auxiliary agent for formulation. Mix and formulate into emulsion, wettable powder, suspension, granule, powder, liquid and the like. In these formulations, the compound of the present invention as an active ingredient, in a weight ratio, usually 0.1 to
95%, preferably 1 to 90%. Examples of the solid carrier include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, fine powder or granules of synthetic hydrous silicon oxide, and the like.
As the liquid carrier, aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol and cellosolve, acetone, cyclohexanone, ketones such as isophorone, soybean oil, vegetable oils such as cottonseed oil, dimethyl sulfoxide, acetonitrile, water and the like. Examples of surfactants used for emulsification, dispersion, moistening and the like include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts. Anionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester,
Examples thereof include nonionic surfactants such as polyoxyethylene sorbitan fatty acid ester. Examples of the auxiliary agent for formulation include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate) and the like.

These formulations are used as they are or after being diluted with water for foliage spraying, or they are used in various forms such as powdered, granulated and mixed with soil, or applied to soil. In addition, when used in combination with other plant disease controlling agents, it can be expected to enhance the controlling effect. Further, it can be used in combination with an insecticide, acaricide, a nematicide, a herbicide, a plant growth regulator, a fertilizer, and a soil conditioner. In addition,
The compound of the present invention is a paddy field, upland, orchard, tea plantation, meadow,
It can be used as an active ingredient of a plant disease controlling agent for lawns and the like. When the compound of the present invention is used as an active ingredient of a plant disease controlling agent, its application amount is usually 1 are.
0.01 g to 50 g, preferably 0.05 g to 20 g, and when the emulsion, wettable powder, suspension, liquid, etc. are diluted with water and applied, the application concentration is usually 0.0001% to 0.5%. %, Preferably 0.0005% to 0.2%, and granules, powders, etc. are applied as they are without any dilution.

[0012]

EXAMPLES The present invention will be described in more detail with reference to production examples, formulation examples, test examples, etc., but the present invention is not limited to these examples. First, production examples of the compound of the present invention are shown.
The compound numbers of the present invention are shown in Table 1 below. Production Example 1 (Production of Compound (2) of the Present Invention) 1-Methyl-3-chloro-4- [2- (2-methylphenoxy) methyl-6-methylphenyl] -1,2,4-
Triazolone [prepared in Preparation Example 1 of Intermediate described below] 0.60 g
(1.75 mmol) and 28% sodium methoxide in methanol (1.7 g, 8.8 mmol) were dissolved in methanol (5 ml), and the mixture was heated under reflux for 4 hours. Pour the reaction solution into ice water,
It was extracted with ethyl acetate. The extract was washed with water and concentrated, and the residue was subjected to silica gel chromatography (eluent; ethyl acetate: n-hexane = 1: 1) to give 1-methyl-3-.
Methoxy-4- [2- (2-methylphenoxy) methyl-6-methylphenyl] -1,2,4-triazolone 0.
25 g (yield 42%) was obtained. Production Example 2 (Production of Compound (1) of the Present Invention) 1-Methyl-3-methoxy-4- [2- (bromomethyl) -6-methylphenyl] -1,2,4-triazolone [Production Example of Intermediate described below] 2 manufactured] 0.80 g (2.56
mmol) and 2,5-xylenol 0.38 g (3.07 mm)
ol) in 5 ml of N, N-dimethylformamide,
0.42 g (3.07 mmol) of potassium carbonate was added to this, and 6
The mixture was stirred at 0 to 70 ° C for 6 hours. Ice water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated, and the residue was chromatographed on silica gel (eluent; ethyl acetate:
n-hexane = 1: 1), 1-methyl-3-methoxy-4- [2- (2,5-dimethylphenoxy) methyl-6-methylphenyl] -1,2,4-triazolone
0.79 g (87% yield) was obtained.

Next, some specific examples of the compound of the present invention are shown in Table 1 together with the compound number and the physical property values. (It is shown in the definition of the substituent of the compound represented by the general formula (4).) In Table 1, Me represents a methyl group, and in the following description, mp represents a melting point.

[Table 1]

Next, a production example of the chlorotriazolone compound represented by the above general formula 5 which is an intermediate compound in the production of the compound of the present invention will be shown. Production Example 1 of Intermediate 1,1-Dimethyl-4- [2- (2-methylphenoxy) methyl-6-methylphenyl] semicarbazide 2.0
A solution of 0 g (6.39 mmol) of methylene chloride was added to 1.90 g (9.59 mmol) of trichloromethyl chloroformate [diphosgene].
Was added dropwise to the methylene chloride solution under ice-cooling. After completion, the mixture was stirred for 1 hour under ice-cooling and then heated under reflux for 5 hours, and the resulting reaction solution was poured into aqueous sodium hydrogen carbonate to separate the layers. The organic layer was washed with water and then concentrated, and the residue was subjected to silica gel column chromatography (eluent; ethyl acetate: n-hexane =).
1: 1), and 1-methyl-3-chloro-4- [2-
(2-Methylphenoxy) methyl-6-methylphenyl] -1,2,4-triazolone 1.65 g (yield 75
%) Was obtained. mp 128.6 ° C. An example of a chlorotriazolone compound represented by the general formula 5 prepared in the same manner is shown below. 1-Methyl-3-chloro-4- [2- (2-chlorophenoxy) methyl-6-methylphenyl] -1,2,4-
Triazolone mp 88.8 ° C 1-methyl-3-chloro-4- [2- (2-methyl-4
-Chlorophenoxy) methyl-6-methylphenyl]-
1,2,4-triazolone mp 188.9 ℃

Next, production examples of the triazolone compound represented by the above general formula 6 will be shown. Preparation Example 2 of intermediate 1,1-dimethyl-4- (2,6-dimethylphenyl)
A solution of 2.07 g (10.0 mmol) of semicarbazide in dioxane was added to 3.00 g (10.0 mmol) of bis (trichloromethyl) carbonate [triphosgene] in 100 ml of dioxane.
Was added dropwise to the solution dissolved in. After completion, the mixture was stirred for 30 minutes at the same temperature and then heated and stirred at a bath temperature of 65 ° C. for 6 hours. Aqueous sodium hydrogen carbonate was added to the resulting reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and concentrated to give 1-methyl-3-chloro-4- (2,6-dimethylphenyl) -1,2,4-triazolone (2.07 g, yield 87%). . mp 84.5 ° C. 1-methyl-3-chloro-4- (2,6-dimethylphenyl) -1,2,4-triazolone 10.0 g (42 mmol)
The N, N-dimethylformamide solution of was added dropwise to a solution of 2.70 g (50 mmol) of sodium methoxide in N, N-dimethylformamide (100 ml) with stirring at 5 ° C or lower. After the completion, the mixture was stirred at the same temperature for 1 hour and then at room temperature for another 3 hours. The resulting reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, concentrated, added with n-hexane, crystallized, and filtered to give 1-methyl-3-methoxy-4- (2,6-dimethylphenyl).
6.16 g (yield 63%) of -1,2,4-triazolone was obtained. mp. 151.9 ° C. 1-methyl-3-methoxy-4- (2,6-dimethylphenyl) -1,2,4-triazolone 16.2 g (69.2 mmo)
l) and N-bromosuccinimide 14.0 g (78.9 mmo
l) was added to carbon tetrachloride (700 ml), to which a catalytic amount of azobisisobutyronitrile was added, and the mixture was reacted under heating under reflux for 5 hours. The reaction solution was filtered, the filtrate was concentrated, the residue was subjected to silica gel column chromatography (eluent; ethyl acetate: toluene = 1: 1), and the obtained crude crystals were recrystallized from ethanol. 13.0 g of 1-methyl-3-methoxy-4- [2- (bromomethyl) -6-methylphenyl] -1,2,4-triazolone (60% yield)
I got mp 114.3 ° C In the same manner as above, 1-methyl-3-chloro-4-
(2,6-dimethyl-4-chlorophenyl) -1,2,
4-triazolone (mp. 136.5 ° C) and 1-methyl-3-methoxy-4- (2,6-dimethyl-4-chlorophenyl) -1,2,4-triazolone (mp.
133.2 ° C) and then 1-methyl-3-methoxy-4
-[2- (Bromomethyl) -4-chloro-6-methylphenyl] -1,2,4-triazolone (mp. 12)
4.5 ° C.) can be manufactured.

Next, formulation examples are shown. The compounds of the present invention are represented by the compound numbers in Table 1, and parts are parts by weight. Formulation Example 1 50 parts of each of the present compounds (1) to (8), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain each wettable powder. . Formulation Example 2 10 parts of each of the compounds (1) to (8) of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene are mixed well to obtain each emulsion. Formulation Example 3 2 parts of each of the compounds (1) to (8) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are well pulverized and mixed, and water is added. After thoroughly kneading, granulate and dry to obtain each granule. Formulation Example 4 25 parts of each of the compounds (1) to (8) of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed and wet until the particle size of the active ingredient becomes 5 microns or less. Grind to obtain each suspension. Formulation Example 5 10 parts of the compounds (1) to (8) of the present invention, 1 part of polyoxyethylene styryl phenyl ether and 89 parts of water are mixed to obtain respective liquid preparations.

Next, it is shown in Test Examples that the compound of the present invention is useful as an active ingredient of a plant disease controlling agent. The compounds of the present invention are shown by the compound numbers in Table 1. The compounds used for comparison and control are shown by the compound symbols in Table 2.

[Table 2] The control efficacy depends on the disease state of the test plant at the time of investigation, that is, the leaves,
Visual observation of the flora of the stem and the degree of lesions, "5" if no flora and lesions are observed, "4" if about 10% is observed, "3" if about 30% is observed, If about 50% is recognized, it is "2", if about 70% is recognized, it is "1", and if there is no difference more than the onset state when the compound is not tested, it is evaluated as "0" and evaluated in 6 levels. , 5, 4, 3, 2, 1, 0, respectively.

Test Example 1 Rice blast control test (preventive effect) A plastic pot was filled with sandy loam soil, and rice (Nihonbare) was sown and grown in a greenhouse for 20 days. Then, Formulation Example 1
The reagent solution made into a wettable powder was diluted with water to a predetermined concentration and sprayed on the leaves so that it adhered sufficiently to the rice leaf surface. After spraying, the plants were air-dried, and a spore suspension of blast fungus was sprayed and inoculated. After inoculation, the mixture was allowed to stand at 28 ° C. under high humidity for 6 days, and then the control efficacy was investigated. Table 3 shows the results. Test Example 2 Rice Stripe Blight Control Test (Preventive Effect) A plastic pot was filled with sandy loam, and rice (Nihonbare) was sown and grown in a greenhouse for 20 days. A reagent solution made into a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the foliage was sprayed so as to sufficiently adhere to the leaf surface of the rice. After spraying, the plants were air-dried and inoculated with bran culture fungus hyphae of wilt fungus at the root. After inoculation, at 28 ℃ and high humidity, 4
After standing for a day, the control efficacy was investigated. Table 3 shows the results. Test Example 3 Wheat Eyebrush Control Test (Preventive Effect) A plastic pot was filled with sandy loam and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. A test agent prepared as an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface of the wheat seedling. After spraying, the spore suspension of wheat ophthalmophilus fungus was inoculated into a wheat strain source and kept at 15 ° C. under high humidity for 14 days, and then the control efficacy was investigated. Table 3 shows the results. Test Example 4 Wheat Powdery Mildew Control Test (Therapeutic Effect) A plastic pot was filled with sandy loam and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. A wheat powdery mildew fungus was sprinkled on the wheat seedlings developed by the second leaf to inoculate. After inoculation, grow in a greenhouse at 23 ° C for 3 days,
The reagent solution made into a suspension according to Formulation Example 4 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface of the wheat. After spraying, the seedlings were further grown for 7 days under illumination and the control efficacy was investigated. Table 3 shows the results. Test Example 5 Cucumber Powdery Mildew Control Test (Preventive Effect) A plastic pot was filled with sandy loam soil, seeded with cucumber (Sagamihanjiro), and grown in a greenhouse for 12 days. A reagent solution made into a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the foliage was sprayed so as to sufficiently adhere to the leaf surface of the cucumber seedling. After spraying, a spore suspension of cucumber powdery mildew was inoculated. After inoculation, the plant was grown at 25 ° C. under illumination for 7 days, and the control efficacy was investigated. Table 3 shows the results.

[0019]

[Table 3]

[0020]

The compound of the present invention exhibits an excellent controlling effect against plant diseases.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Rei Matsunaga 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd.

Claims (11)

[Claims] 1. A compound represented by the general formula: [Wherein, X represents a methyl group or a halogen atom, and Y represents
And Z are the same or different and each represents a hydrogen atom, a methyl group or a halogen atom. ] The triazolone derivative shown by these. 2. The triazolone derivative according to claim 1, wherein X is a methyl group. 3. The triazolone derivative according to claim 1, wherein Z is a hydrogen atom or a 4-chlorine atom. 4. The triazolone derivative according to claim 1, wherein Z is a hydrogen atom. 5. The triazolone derivative according to claim 1, 2, 3 or 4, wherein Y is a hydrogen atom, a methyl group or a chlorine atom. 6. The triazolone derivative according to claim 1, 2, 3 or 4, wherein Y is a hydrogen atom or a 5-methyl group. 7. A formula A compound represented by the formula: 8. A formula A compound represented by the formula: 9. A plant disease controlling agent comprising the triazolone derivative according to claim 1 as an active ingredient. 10. A general formula: [Wherein, X represents a methyl group or a halogen atom, and Y represents
And Z are the same or different and each represents a hydrogen atom, a methyl group or a halogen atom. ] The chlorotriazolone compound shown by these. 11. A general formula: embedded image [In the formula, Q represents a bromine atom or a chlorine atom, and Z represents a hydrogen atom, a methyl group or a halogen atom. ] The triazolone compound shown by these.