JPH07215971A - Sulfoamoyltriazole derivative and microbicide containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To provide a new sulfamoyltriazole derivative having an excellent microbicidal activity, excellent in safety for crops, and useful as a microbicide having good preventing and treating effects at a low dose. CONSTITUTION:A compound of formula I [R<1>, R<2>, R<3> are H, halogen, lower alkyl, nitro; R<4>, R<5> are lower alkyl, or R<4> and R<5> together form a (lower alkyl- substituted) 3-6C alkylene]. For example, 1-(N,N-dimethylsulfamoyl)-3-(3,5- dimethyl-4-chloropyrazol-1-yl)sulfonyl-1,2,4-triazole. The compound of formula I is obtained by reacting a compound of formula II with a compound of formula III (X is halogen) in the presence of a base preferably in a solvent.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel sulfamoyltriazole derivative which has not been described in the literature and a fungicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art In JP-A-63-255269, sulfamoyltriazole derivatives are described as antifungal agents. However, those known compounds are
The 2,4-triazole moiety is different from the compound of the present invention in that it does not have a hydrogen atom and a pyrazolylsulfonyl group at two carbon atoms at the same time.

[0003]

The bactericidal activity of these sulfamoyltriazole derivatives is not always satisfactory. An object of the present invention is to provide a novel sulfamoyltriazole derivative having an excellent bactericidal activity and exhibiting a preventive effect and a therapeutic effect with a very low dose against various diseases without damaging useful crops. It is in.

[0004]

Means for Solving the Problems The present inventors have synthesized various novel sulfamoyltriazole derivatives and investigated their physiological activities, and as a result of diligent studies, as a result, a specific sulfamoyltriazole derivative was identified. The present invention has been completed by discovering that a preventive effect and a therapeutic effect can be exerted against various diseases with an extremely low dose without damaging useful crops. Thus, according to the present invention, the following general formula (I):

[0005]

[Chemical 3]

[Wherein R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group or a nitro group, and R ⁴ and R ⁵ are the same or different and are a lower alkyl group. Shown or R ⁴ and R ⁵
Together represent an alkylene chain having 3 to 6 carbon atoms which may be substituted with a lower alkyl group], and a sterilization containing the sulfamoyltriazole derivative as an active ingredient. An agent is provided.

Specific examples of the atoms and groups defined in the above general formula (I) of the present invention are shown below. Halogen atom: fluorine, chlorine, bromine or iodine. Lower alkyl group; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, neopentyl or n
Examples thereof include a linear or branched lower alkyl group having 1 to 6 carbon atoms such as a hexyl group.

In the compound represented by the general formula (I), R ¹ , R ² and R ³ are hydrogen atoms; halogen atoms such as chlorine or bromine; or lower alkyl groups such as methyl or ethyl; Compounds in which ⁴ and R ⁵ are methyl or ethyl are preferred. Further, a compound in which R ¹ , R ² and R ³ are hydrogen atoms; halogen atoms such as chlorine and bromine; or a methyl group and R ⁴ and R ⁵ are methyl groups is particularly preferable.

Specific examples of the compound of the present invention represented by the general formula (I) are shown in Table 1. The abbreviations used in the tables of the present specification have the following meanings. Me = methyl group Et = ethyl group Pr =
n-propyl group iPr = isopropyl group Bu = n-butyl group iBu
= Isobutyl group sBu = s-butyl group tBu = t-butyl group Hex
= N-hexyl group

[0010]

[Table 1]

[0011]

[Table 2]

Next, the method for producing the compound represented by the above general formula (I) of the present invention will be explained with reference to two examples of Method A and Method B. However, the compound according to the present invention is not limited to the compounds produced by these methods. Method A Method A-1

[0013]

[Chemical 4]

[In the formula, X represents a halogen atom, and R ¹ ,
R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above] The compound (I) of the present invention is represented by the triazole derivative represented by the general formula (II) and the general formula (III). It can be obtained by reacting with a sulfamoyl halide formed in the presence of a base, preferably in a solvent. At that time, the amount of the reagent to be used in the reaction is usually 1 mol of the triazole derivative (II) to sulfamoyl halide (II).
I) is 1 to 1.5 equivalents, and the base is 1 to 5 equivalents. The reaction temperature can be arbitrarily set within the temperature range of under ice cooling or the boiling point of the solvent. The reaction time varies depending on the set conditions, but usually it can be completed in 10 minutes to 24 hours.

The solvent that can be used is not particularly limited as long as it is substantially inert to the above reaction.
Aliphatic hydrocarbons such as hexane, heptane, ligroin or petroleum ether; aromatic hydrocarbons such as benzene, toluene or xylene; chloroform, carbon tetrachloride,
Halogenated hydrocarbons such as dichloroethane, chlorobenzene or dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone or cyclohexanone; nitroethane or nitrobenzene Nitro compounds such as; Nitriles such as acetonitrile or isobutyronitrile; Tertiary amines such as pyridine, triethylamine, N, N-diethylaniline, tributylamine or N-methylmorpholine; Acids such as N, N-dimethylformamide Examples include amides; sulfur compounds such as dimethyl sulfoxide or sulfolane, and mixtures thereof. When a solvent is used, the amount used is usually 1 by weight with respect to the triazole derivative (II).
It is within a range of 20 times.

Examples of the base that can be used include pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butyl-4-methylpyridine, 4-dimethylaminopyridine, triethylamine, ethyldiisopropylamine,
Organic bases such as N, N-diethylaniline or potassium bis (trimethylsilyl) amide; inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate; metal hydrides such as sodium hydride or potassium hydride; sodium Examples thereof include alkali metal alkoxides such as methoxide and sodium ethoxide.

After completion of the reaction, the reaction solution may be purified by recrystallization, chromatography or the like, if necessary, by subjecting to ordinary post-treatment such as extraction with an organic solvent by adding water. The triazole derivative represented by the general formula (II) can be produced according to the following method A-2, but is not limited to the one produced by this method. Method A-2

[0018]

[Chemical 5]

[Wherein Y represents a halogen atom, R ¹ ,
R ² and R ³ have the same meanings as described above.] As shown in the above reaction formula, the triazole derivative represented by the general formula (II) is a compound represented by the general formula (IV) in a suitable solvent in the presence of a base. It can be obtained by reacting the compound represented by and the compound represented by the general formula (V). At that time, the amount of the reagent used in the reaction is usually the compound (IV) 1
The compound (V) is 1 to 1.2 equivalents and the base is 1 equivalent to the equivalents.
Within the range of 5 equivalents. The reaction temperature can be arbitrarily set within the temperature range of under ice cooling or the boiling point of the solvent. The reaction time is
Although it can be variously changed depending on the setting conditions, it can be usually finished in 1 to 24 hours.

The solvent that can be used is not particularly limited as long as it is a solvent which is substantially inert to the above reaction, and examples thereof include ketones such as acetone; tetrahydrofuran, dioxane, diethyl ether and the like. Examples thereof include ethers; esters such as ethyl acetate; halogenated hydrocarbons such as dichloromethane; aromatic hydrocarbons such as benzene or chlorobenzene; acid amides such as N, N-dimethylformamide. These solvents can be used alone or as a mixture, and a mixed system of water and the above solvents can also be used. The amount of the solvent used is not particularly limited, but usually 5% by weight of the compound (IV) is used.
-20 times the amount is suitable.

Examples of the base which can be used are pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butyl-4-methylpyridine, 4-dimethylaminopyridine, triethylamine, ethyldiisopropylamine or N, Examples thereof include organic bases such as N-diethylaniline; and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate.

The compound represented by the general formula (II) can be isolated from the reaction mixture by a conventional method, and if necessary, can be easily purified by recrystallization or chromatography. Compounds (IV) and (V), which are the starting materials of this method, can be prepared by known methods [for example, JP-A-48-77030 for compound (IV) and Large Organic Chemistry for compound (V). Volume 15 258-286
Refer to page] or a method according to it or the like. Further, the compound of the present invention represented by the general formula (I) can also be produced by the following method.

Method B Method B-1

[0024]

[Chemical 6]

[Wherein Y represents a halogen atom, R ¹ ,
R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above.] As shown in the above reaction formula, the compound of the present invention represented by the general formula (I) is represented by the general formula (V). It can be obtained by reacting a compound of formula (VI) with a compound of formula (VI) in the presence of a base in a suitable solvent. The details of the reaction are exactly the same as those in the above-mentioned Method A-2, and the compounds (IV) and (II) in Method A-2 need only be replaced with the above-mentioned compounds (VI) and (I), respectively. The sulfamoyltriazole derivative represented by the general formula (I) produced by this method can be isolated from the reaction mixture by a conventional method,
If necessary, it can be easily purified by recrystallization, chromatography or the like. Further, when Y is a chlorine atom, the compound represented by the general formula (VI) can be produced by, for example, the following B-2 method, but is not limited to the one produced by this method. B-2 method

[0026]

[Chemical 7]

[In the formula, X represents a halogen atom, and R ⁴ and R ⁵ have the same meanings as described above] The compound represented by the general formula (VIII) includes compounds (VII) and (III) It can be obtained by reacting with a sulfamoyl halide represented by in the presence of a base, preferably in a solvent. The details of the reaction are exactly the same as those in Method A-1 described above, and it is sufficient to replace the compounds (II) and (I) in Method A-1 with the above compounds (VII) and (VIII), respectively. After completion of the reaction, the reaction solution can be purified by recrystallization, chromatography or the like, if necessary, by subjecting it to ordinary post-treatment such as extraction with an organic solvent by adding water. Compound (VIII) obtained by the above procedure is oxidatively chlorinated by a method according to a known method [see JP-A-5-43557] to obtain a compound represented by the general formula (VI). You can

The sulfamoyltriazole derivative represented by the above general formula (I) of the present invention is used for the downy mildew of grape ( Pl.
asmopara viticola ), downy mildew of cucurbits ( Pseudoperonosp
ora cubensis ), wilting plague ( Phytophthora meloni)
s), tomato gray late blight (Phytophthora capsici), late blight (Phytophthora infestans), cruciferous vegetables downy mildew (Peronospora brassicae), green onion downy mildew (Peronospor
a destructor ), downy mildew of spinach ( Peronospora sp.
inaciae ), soybean downy mildew ( Peronospora manshurica ),
Downy mildew of broad beans ( Peronospora viciae ), plague of tobacco ( Phytophthora nicotiana var.nicotiana ), plague of potato ( Phytophthora infestans ), downy mildew of hops ( Pseudoperonospora humuli ), plague of pineapple ( P
hytophthora cinnamomi ), the plague of bell peppers ( Phytophtho
ra capsici ), strawberry root rot ( Phytophthora fragari)
e ), or excellent bactericidal activity against a wide range of plant diseases caused by oomycetes such as wilt disease of various crops (due to Pythium spp.), rice blast ( Pyricularia oryzae ) and wheat rust ( Puccinia recondita ). have.

The fungicide of the present invention is characterized by containing the sulfamoyltriazole derivative represented by the general formula (I) as an active ingredient. When the compound (I) of the present invention is used as a bactericidal agent, it is mixed with a carrier or diluent, an additive, an auxiliary agent and the like by a known method, and a formulation form usually used as an agricultural chemical, for example, powder, granule It can be prepared and used as an agent, a wettable powder, an emulsion, an aqueous solvent, a flowable agent and the like. Also, other pesticides, such as fungicides, insecticides, acaricides, herbicides, plant growth regulators,
It can be used as a mixture or in combination with fertilizers and soil conditioners. Especially by mixing with other fungicides,
Not only can the amount of drug used be reduced and labor saving can be achieved, but also a broader sterilization spectrum due to the synergistic action of both drugs and a higher effect due to a synergistic action can be expected.

The carriers or diluents used in the preparation include solid or liquid carriers generally used. Examples of the solid carrier include clays represented by kaolinite group, montmorillonite group, illite group, polygoskite group and the like; specifically, pyrophyllite, attapulgite, sepiolite, kaolinite, bentonite, vermiculite, mica or talc; gypsum; , Other inorganic substances such as calcium carbonate, dolomite, diatomaceous earth, magnesium lime, apatite, zeolite, silicic anhydride or synthetic calcium silicate;
Soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, starch or crystalline cellulose and other plant organic substances; coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, cobal gum or Examples thereof include synthetic or natural polymer compounds such as dummal gum; waxes such as carnauba wax and beeswax, urea and the like.

Suitable liquid carriers are, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil or white oil; aromatic hydrocarbons such as xylene, ethylbenzene, cumene or methylnaphthalene; trichloroethylene, monochloro. Chlorinated hydrocarbons such as benzene or orthochlorotoluene; ethers such as dioxane or tetrahydrofuran; acetone;
Ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone or isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate or diethyl succinate; methanol, n-hexanol, ethylene glycol, diethylene glycol Alcohols such as cyclohexanol or benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether or diethylene glycol butyl ether; polar solvents such as dimethylformamide or dimethylsulfoxide; or water.

In addition, emulsification, dispersion, wetting, spreading, spreading, binding, control of disintegration, stabilization of active ingredient of the compound of the present invention,
Surfactants and other auxiliary agents can be used for the purpose of improving fluidity, preventing rust, and preventing freezing. Examples of the surfactant to be used may be nonionic, anionic, cationic and zwitterionic, but usually nonionic and / or anionic are used. It Suitable nonionic surfactants include, for example, compounds obtained by polymerizing addition of ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol or oleyl alcohol; polymerization addition of ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol. Compounds: Compounds obtained by polymerizing addition of ethylene oxide to higher fatty acids such as palmitic acid, stearic acid, oleic acid; Higher fatty acid esters of polyhydric alcohols such as sorbitan and compounds obtained by polymerizing addition of ethylene oxide, block polymerization of ethylene oxide and propylene oxide Examples thereof include added compounds.

Suitable anionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate or oleyl alcohol sulfate amine salt;
Sodium sulfosuccinate dioctyl ester or 2
-Alkyl sulfonates such as sodium ethylhexene sulfonate; sodium isopropylnaphthalene sulfonate, sodium methylenebisnaphthalene sulfonate,
Examples thereof include aryl sulfonates such as sodium lignin sulfonate and sodium dodecylbenzene sulfonate. Furthermore, the bactericide of the present invention improves the properties of the preparation and, for the purpose of enhancing the effect, polymer compounds such as casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose and polyvinyl alcohol. Other auxiliary agents can be used in combination. The above carriers and various auxiliary agents are appropriately used alone or in combination depending on the purpose, taking into consideration the formulation system of the preparation, the application scene and the like.

The content of the active ingredient of the compound of the present invention in the various dosage forms thus obtained varies depending on the dosage form, but is usually 0.1 to 99% by weight, preferably 1 to 99% by weight. 80% by weight is most suitable. In the case of a wettable powder, for example, the active ingredient compound is usually contained in an amount of 5 to 90%, and the balance is a solid carrier and a dispersion wetting agent, and a protective colloid agent, a defoaming agent and the like are added if necessary. In the case of granules, for example, the active ingredient compound is usually contained in an amount of 1 to 35% by weight, and the balance is a solid carrier and a surfactant. The active ingredient compound is either uniformly mixed with the solid carrier or is evenly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm. For emulsions,
For example, the active ingredient compound is usually contained in an amount of 5 to 80% by weight, which contains about 5 to 20% by weight of an emulsifier, and the rest is a liquid carrier, and if necessary, a spreading agent, a rust preventive agent, etc. Added. In the case of a flowable agent, for example, the active ingredient compound is usually contained in an amount of 5 to 50% by weight.
-10 to 10% by weight of a dispersion wetting agent, the rest is water, and a protective colloid agent, an antiseptic agent, an antifoaming agent and the like are added if necessary.

The sulfamoyltriazole derivative of the present invention can be used as a fungicide in the form of the compound of the general formula (I) as it is or in any of the above-mentioned preparation forms. The use concentration of the compound of the present invention varies depending on the target crop, method of use, formulation form, application amount and the like and cannot be specified unconditionally, but as the amount of the compound represented by the general formula (I) (amount of active ingredient), For foliage treatment 0.1-1
000 ppm, preferably 1 to 500 ppm, and 10 to 100,000 g / h in the case of soil treatment
a, preferably 200 to 20,000 g / ha.
Next, the present invention will be described more specifically with reference to examples.

[0036]

EXAMPLES Production Example 1: i) 3- (3-t-butyl-5-methylpyrazole-1)
-Yl ) Preparation of sulfonyl-1,2,4-triazole 0.83 g of 3-t-butyl-5-methylpyrazole was dissolved in 10 ml of tetrahydrofuran, and 0.61 g of triethylamine was added with stirring. Further under ice cooling, 3
-Chlorosulfonyl-1,2,4-triazole 1.00
g was gradually added, and the mixture was stirred at room temperature for about 2 hours. The solvent was evaporated, 2N hydrochloric acid was added under cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off to give a crude product of the title compound: 0.9
2 g (yield 57%) was obtained. ii) 1- (N, N-dimethylsulfamoyl) -3- (3
-T-butyl-5-methylpyrazol-1-yl) sul
Of phenyl-1,2,4-triazole (Compound No. 15)
Production 3- (3-t-butyl-5-methylpyrazol-1-yl) sulfonyl-1, produced in the same manner as in i) above.
A crude product of 2,4-triazole (0.90 g) was dissolved in acetonitrile (7 ml), and anhydrous potassium carbonate (0.56 g) was used.
Then, 0.57 g of N, N-dimethylsulfamoyl chloride was gradually added at room temperature with stirring. After heating under reflux for 1 hour, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, evaporated to remove the solvent, and purified by silica gel chromatography to give the title compound (0.87 g, yield 69).
%) Was obtained.

Production Example 2: i) 3- (3,5-dimethyl-4-chloropyrazole-
Preparation of 1-yl) sulfonyl-1,2,4-triazole 1.96 g of 3,5-dimethyl-4-chloropyrazole was dissolved in 30 ml of tetrahydrofuran, and 1.67 g of triethylamine was added with stirring. Further under ice cooling, 3
-Chlorosulfonyl-1,2,4-triazole 2.51
g was gradually added, and the mixture was stirred at room temperature for about 2 hours. The solvent was evaporated, 2N hydrochloric acid was added with cooling, and the mixture was filtered to obtain 1.53 g (yield 39%) of crude crystals of the title compound. ii) 1- (N, N-dimethylsulfamoyl) -3-
(3,5-dimethyl-4-chloropyrazol-1-yl)
Sulfonyl-1,2,4-triazole (Compound No. 1
Preparation of 6) 3- (3,5-dimethyl-4-chloropyrazol-1-yl) sulfonyl-prepared by the same method as in i) above.
1.02 g of a crude product of 1,2,4-triazole was dissolved in 10 ml of acetonitrile, and anhydrous potassium carbonate 0.6
6 g was added, and N, N-dimethylsulfamoyl chloride 0.69 g was gradually added at room temperature with stirring. After heating under reflux for 1 hour, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, then the solvent was evaporated to give crude crystals. This was recrystallized from n-hexane / ethyl acetate to obtain 0.80 g of the title compound (yield 54%).

Production Example 3: i) 1- (N, N-dimethylsulfamoyl) -3-cu
Rorosuruhoniru 1,2, 4-triazole prepared 1-(N, N-dimethylsulfamoyl) -3- benzylthio-1,2,4-2N hydrochloric acid 10 triazole 18g
Suspend in 0 ml, and add 4 g of chlorine gas 16g at 0-5 ° C.
It took a while to blow. The formed crystals were filtered, washed with water, washed with hexane and dried to give 12.5 g of the title compound.
(Yield 76%) was obtained. ¹ H-NMR [δ (ppm) solvent CDCl ₃ TMS = 0 pp
m] 3.13 (s, 6H), 8.73 (s, 1H) ii) 1- (N, N-dimethylsulfamoyl) -3-
(3,5-Dimethylpyrazol-1-yl) sulfonyl-
Production of 1,2,4-triazole (Compound No. 12) 0.58 g of 3,5-dimethylpyrazole was dissolved in 15 ml of tetrahydrofuran, and 0.67 g of triethylamine was added with stirring. Further, under ice-cooling, 1.65 g of 1- (N, N-dimethylsulfamoyl) -3-chlorosulfonyl-1,2,4-triazole prepared by the same method as in i) above was gradually added, and the mixture was cooled to room temperature. And stirred for about 4 hours.
The solvent was evaporated, 2N hydrochloric acid was added under cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, then the solvent was evaporated to give crude crystals.
This was recrystallized from n-hexane / ethyl acetate to give the title compound (0.90 g, yield 45%). The melting point and ¹ H-of the materials prepared using the above examples and similar methods.
The NMR δ values are shown in Table 2 below.

[0039]

[Table 3]

Next, several modes of formulation examples using the compound of the present invention will be shown. The "parts" in the following preparations are based on weight. Formulation Example 1 (emulsion) Compound number: 16 10 parts Xylene 45 parts Dodecylbenzene sulfonate calcium 7 parts Polyoxyethylene styryl phenyl ether 13 parts Dimethylformamide 25 parts The above components were uniformly mixed and dissolved to obtain 100 parts of an emulsion. Formulation example 2 (wettable powder) Compound number: 16 20 parts Diatomaceous earth 70 parts Lignin calcium sulfonate 5 parts Naphthalene sulfonic acid formalin condensate 5 parts The above components were mixed and ground to obtain 100 parts of a wettable powder.

Formulation Example 3 (Granule) Compound No .: 16 5 parts Bentonite 50 parts Talc 42 parts Sodium lignin sulfonate 2 parts Polyoxyethylene alkylaryl ether 1 part After thoroughly mixing the above, add an appropriate amount of water. The mixture was kneaded and 100 parts of granules were obtained using an extrusion granulator. Formulation Example 4 (flowable agent) Compound number: 16 30 parts Sulfosuccinic acid di-2-ethylhexyl ester sodium salt 2 parts Polyoxyethylene nonyl phenyl ether 3 parts Defoamer 1 part Propylene glycol 5 parts Water 59 parts The above is wet ball mill The mixture was uniformly pulverized and mixed to obtain 100 parts of a flowable agent. According to the above-mentioned formulation examples, bactericides using the compound of the present invention can be formulated. Next, with reference to Test Examples, the effect of the present invention fungicide against various plant diseases will be specifically described.

Test Example 1 Cucumber downy mildew preventive effect test Cucumber seeds (variety:
5 seeds of Sagamihanjiro were seeded and grown in a greenhouse for 7 days.
A wettable powder prepared according to Formulation Example 2 was diluted with water to a cucumber seedling in which cotyledons had spread so that the concentration of the active ingredient was 200 ppm, and 10 ml was sprayed per pot. 1 day after spraying,
A spore suspension of cucumber downy mildew ( Pseudoperonospora cubensis ) was spray-inoculated, kept in a humid chamber at 20 ° C for 1 day, and then sickened in a greenhouse. Seven days after the inoculation, the disease degree was investigated according to the following criteria, and the disease degree and the control value were obtained.

Category Degree of onset Health: No onset of disease Small: Lesion area is less than 1/3 Medium: Lesion area is less than 1/3 to 2/3 Large: Lesion area is 2/3 or more

[0044]

[Equation 1]

N ⁰ : number of leaves of “healthy” disease severity n ¹ : number of leaves of “small” disease severity n ² : number of leaves of “middle” disease severity n ³ : number of leaves of “large” disease severity

[0046]

[Equation 2]

The results of evaluation of the obtained control value according to the following evaluation criteria are shown in Table 3 below. Evaluation criteria A: Control value is 95% or more B: Control value is 80 to less than 95% C: Control value is 50 to less than 80% D: Control value is less than 50%

[0048]

[Table 4]

Test Example 2 Rice Blast Prevention Effect Test Eight rice paddy seeds (cultivar: Koshihikari) were sown in a vinyl chloride pot having a diameter of 7 cm and grown in a greenhouse for 2-3 weeks. A wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 200 ppm, and 10 ml per pot was sprayed on the rice seedlings having the third leaves. 1 day after spraying,
A spore suspension of blast fungus ( Pyricularia oryzae ) was spray-inoculated, kept in a humid chamber at 25 ° C for 1 day, and then sickened in a greenhouse. The number of lesions was measured 7 days after the inoculation, and the control value was calculated according to the following formula. This was evaluated using the same evaluation criteria as in Test Example 1 above. The results are shown in Table 4 below.

[0050]

[Equation 3]

[0051]

[Table 5]

Test Example 3 Wheat Leaf Rust Preventive Effect Test Five wheat seeds (variety: Norin 61) were sown in a vinyl chloride pot having a diameter of 7 cm and grown in a greenhouse for 8 days.
A wettable powder prepared according to Formulation Example 2 was diluted with water so that the wheat seedlings having the first leaf developed were diluted with water so that the concentration of the active ingredient was 200 ppm, and 10 ml was sprayed per pot. 1 day after spraying,
A spore suspension of wheat leaf rust ( Puccinia recondita ) was spray-inoculated and placed in a humid chamber at 20 ° C. 18 days after inoculation
It was moved to an artificial weather room at -25 ° C. Seven days after the inoculation, the average number of lesions per leaf of the first leaf was examined, and the control value was calculated according to the following calculation formula. This was evaluated using the same evaluation criteria as in Test Example 1 above. The results are shown in Table 5.

[0053]

[Equation 4]

[0054]

[Table 6]

[0055]

The novel sulfamoyltriazole derivative according to the present invention is characterized in that the 1,2,4-triazole moiety has a hydrogen atom and a pyrazolylsulfonyl group at two carbon atoms at the same time. It is considered that it exhibits excellent bactericidal activity.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Seiichiro Yamada 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Mitsubishi Petrochemical Co., Ltd. Tsukuba Research Institute

Claims (2)

[Claims] 1. A compound represented by the general formula (I): [Wherein R ¹ , R ² and R ³ are the same or different,
A hydrogen atom, a halogen atom, a lower alkyl group or a nitro group, R ⁴ and R ⁵ are the same or different and represent a lower alkyl group, or R ⁴ and R ⁵ together are substituted with a lower alkyl group. 3 to 3 carbon atoms
6 shows an alkylene chain of 6]. 2. General formula (I): [Wherein R ¹ , R ² and R ³ are the same or different,
A hydrogen atom, a halogen atom, a lower alkyl group or a nitro group, R ⁴ and R ⁵ are the same or different and represent a lower alkyl group, or R ⁴ and R ⁵ together are substituted with a lower alkyl group. 3 to 3 carbon atoms
6 shows an alkylene chain of 6] is contained as an active ingredient a sulfamoyltriazole derivative.