JPH0517472A - Novel triazole derivatives and herbicides - Google Patents

Abstract

(57) [Summary] [Object] An object of the present invention is to provide a triazole derivative which has excellent herbicidal efficacy and is highly safe for humans and livestock and useful crops. [Structure] The triazole derivative of the present invention has the general formula (1):
It is represented by. [Chemical formula 1] [In the formula, R ¹ and R ² are the same or different and each represents a lower alkyl group, a lower alkenyl group, or R ¹ and R ²
Represents a lower alkylene group forming a ring with and X and Y are
The same or different, a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a halogen atom,
Represents a cyano group, or represents a lower alkyl group or a phenyl group which may be substituted with a halogen atom, and n represents
Represents an integer of 0, 1, or 2. ] The novel triazole derivative shown by these.

Description

Detailed Description of the Invention

[0001]

[Object of the Invention]

FIELD OF THE INVENTION The present invention relates to a novel triazole derivative and a herbicide containing the derivative as an active ingredient. Therefore, the present invention is useful in the chemical industry as well as agriculture, especially in the agrochemical manufacturing industry.

[0002]

2. Description of the Related Art The compounds similar to the novel triazole derivative of the present invention include the following compounds, all of which are known to have herbicidal activity.

Japanese Unexamined Patent Publication No. 3-90069 General formula

[Chemical 3] In the formula, R represents a lower alkyl group or a halogen atom.

Japanese Unexamined Patent Publication No. 1-121279 General formula

[Chemical 4]

In the formula, R ₁ and R ₂ are the same or different and each represents a lower alkyl group, a lower alkenyl group or a lower alkylene group which forms a ring between R ₁ and R _2, and X and Y are , The same or different, each represents a hydrogen atom, a halogen atom, or a lower alkyl group, and n represents an integer of 0, 1, or 2.

Japanese Unexamined Patent Publication No. 1-106883 General formula

[Chemical 5]

In the formula, R ₁ and R ₂ are the same or different and represent a lower alkyl group, X and Y are the same or different, CH or a nitrogen atom, and Z is the same or different, It represents a halogen atom or a lower alkyl group, m represents 0, 1, or 2, and n represents 0, 1, or 2.

JP-A-59-39880 General formula

[Chemical 6]

In the formula, R ₁ and R ₂ represent a lower alkyl group or a lower alkylene group which forms a ring with R ₁ and R _2, and X represents
It represents a halogen atom or a lower alkyl group, R ₃ represents a hydrogen atom, and n represents 0, 1, or 2. However, when R ₃ is a hydrogen atom, m represents 1, 2 or 3.

JP-A-3-99066 (European Patent Publication No. 422369) General formula

[Chemical 7]

In the formula, R ₁ and R ₂ represent an alkyl group, and R 1
₃ represents a 5-membered ring containing 1 or 2 nitrogen atoms which may be substituted with a halogen atom, a cyano group, an alkyl group or a phenyl group, and one oxygen atom or a sulfur atom, and n
Represents an integer of 0, 1 or 2.

[0012]

However, the compounds described in these documents are not necessarily satisfactory because they have insufficient herbicidal efficacy or cause phytotoxicity to crops as shown in the test examples below. It is hard to say that it is a kimono,
It is desired to develop a herbicide that has few such defects.

The present invention provides a novel herbicide having excellent herbicidal activity and safety as a herbicide for paddy rice and a herbicide for field action.

[0014]

[Means for Solving the Problems] The inventors of the present invention have synthesized a number of triazole derivatives in order to achieve the above-mentioned object, and have diligently studied their usefulness. as a result,
A novel triazole derivative represented by the following general formula (1), in which a thiazole group is bonded to a thio group, a sulfinyl group or a sulfonyl group, is a weed in a paddy field, particularly a highly damaging weed in a paddy field, without damaging the crops. The present invention has been completed by discovering that it exhibits an excellent herbicidal effect on the northern lobster at an extremely low dose. That is, the gist of the first aspect of the present invention lies in the general formula (1)

[Chemical 8]

[0015]

[Wherein R¹And R²Are the same or different
Or represents a lower alkyl group or a lower alkenyl group, or
Or R¹And R² Represents a lower alkylene group forming a ring with and X
And Y are the same or different and each is a hydrogen atom or a lower alkyl.
Kill group, lower alkenyl group, lower cycloalkyl group, ha
Rogen atom, cyano group, or lower alkyl group
Alternatively, a phenyl group which may be substituted with a halogen atom is
And n represents an integer of 0, 1, or 2. ]]
It is a novel triazole derivative.

In the compound represented by the general formula (1),
In the formula, in the definition of R ¹ , R ² , X and Y, a lower alkyl group has 1 to 6 carbon atoms and is linear or branched, and is, for example, a methyl group, an ethyl group or a propyl group. Group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, isohexyl group and the like. Further, the lower cycloalkyl group of X and Y has a carbon number of 3 to 6, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.

Also, R¹ , R² Lower in the definitions of, X, Y
In the case of an alkenyl group, it may have 2 to 6 carbon atoms,
For example, vinyl group, 1-propenyl group, allyl group, isoprene group
Lopenyl group, 1-butenyl group, 2-butenyl group, 2-pentenyl group
Examples thereof include an montenyl group and a 2-hexenyl group.

Furthermore, R¹ , R² Of the definition of
In the case of a phenyl group, it has 1 to 6 carbon atoms and is linear or branched.
It may have a variety of shapes, for example, a methylene group, an ethylene group,
Trimethylene group, 1-methylethylene group, 2-methylethyl group
Tylene group, tetramethylene group, dimethylmethylene group,
Ntamethylene group, 1-methylpentyl group, hexamethylene
Group.

The gist of the second invention is as follows.
A herbicide containing the compound of the formula (1) as an active ingredient.

Next, typical examples of the compounds of the general formula (1) of the present invention are shown in Tables 1 to 5. However, compound No.
Is also referred to in the following examples and test examples.

[0022]

[Chemical 9]

[0023]

[Table 1]

[0024]

[Table 2]

[0025]

[Table 3]

[0026]

[Table 4]

[0027]

[Table 5]

[0028]

The compound of the general formula (1) of the present invention is a novel compound. The compound of the general formula (1) acts as an active ingredient for controlling various weeds in paddy fields and upland fields.

[0029]

EXAMPLES (Production Method of the Compound of the Present Invention) Next, the production method of the compound of the present invention will be described in detail. General formula (2) as a starting material

[Chemical 10]

(In the formula, X, Y and n have the above-mentioned meanings.) And the triazole derivative represented by the general formula (3).

[Chemical 11]

(Wherein R ¹ and R ² have the same meanings as described above, and Z represents a halogen atom), and then reacted with a carbamoyl halide represented by the general formula (1)

[Chemical 12] (In the formula, X, Y, R ¹ , R ² and n have the above-mentioned meanings.) A compound of formula (1) is obtained.

In the above reaction, when the desired compound of formula (1) is a sulfinyl compound (n = 1) or a sulfonyl compound (n = 2), a compound of formula (2) in which the S moiety is similarly oxidized as a starting material is used. ) Compound may be used, or a compound of the formula (1) in which S is unoxidized (n = 0) may be produced and, if necessary, oxidized.

The step of reacting the oxidized or unoxidized compound of formula (2) with the compound of formula (3) is carried out in an amount of 1 equivalent or more, preferably 1 to 2 equivalents, of the dehydrohalogenating agent with respect to the compound of formula (2). In the presence, 1-2 equivalents, preferably 1-1.2 equivalents of compound of formula (3) are reacted in a suitable solvent. The reaction temperature is 0 to 150 ° C, preferably 20 to 70 ° C.

Examples of the dehydrohalogenating agent include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, and organic bases such as triethylamine, pyridine and N, N-diethylaniline. .

Examples of the solvent include hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, tetrachlorocarbonic acid and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran and dioxane.
In addition to ketones such as acetone, methyl ethyl ketone, and cyclohexanone, ethyl acetate, acetonitrile,
Examples of the solvent include dimethylformamide, pyridine, dimethylsulfoxide, a water solvent, and a suitable mixed solvent thereof.

After completion of the reaction, the reaction solution may be purified by a usual post-treatment such as extraction with an organic solvent and concentration by adding water, and if necessary, operations such as chromatography and recrystallization.

The oxidation step can be carried out, for example, by oxidizing with an oxidizing agent in a suitable solvent.

Examples of the oxidizing agent used here include aromatic peracids such as metachloroperbenzoic acid, aliphatic peracids such as peracetic acid and pertrifluoroacetic acid, hydrogen peroxide, potassium permanganate, and chromic acid. Inorganic oxidizers are listed. Examples of the solvent used at that time include methylene chloride, chloroform, acetone, acetic acid, diethyl ether, water and the like, or a mixed solvent thereof.

The reaction temperature is 0 to 100 ° C., and the reaction time is 10 minutes to 24 hours.

After completion of the reaction, water is added to carry out usual post-treatments such as extraction with an organic solvent and concentration to obtain the desired product. If necessary, operations such as chromatography and recrystallization are performed. Examples of production by this method are shown in Examples 1 to 4.

The triazole derivative represented by the general formula (2), which is a starting material, is a novel compound, of which n is 0.
Is the general formula (4)

[Chemical 13]

(In the formula, X and Y have the same meanings as described above, and W represents a halogen atom.) And a 2-halothiazole derivative represented by the general formula (5).

[0043]

[Chemical 14] (In the formula, M represents an alkali metal.) It can manufacture by reacting with the compound shown.

The formula (4) of the 2-halothiazole derivative is
The compounds are known or can be synthesized by known methods.

Reference Production Example 1 shows a production example of the compound of formula (2) as a starting material.

Example 1. 1- (diethylcarbamoyl) -3- (4-methyl 5
-Cyano-thiazol-2-yl) -thio-1,2,4
-Preparation of triazole (Compound No. 103) 11.2 g of 3- (4-methyl-5-cyano-thiazol-2-yl) -thio-1,2,4-triazole was dissolved in 80 ml of acetone, and 7.6 g of potassium carbonate.
And 7.5 g of diethylcarbamoyl chloride were added,
The mixture was stirred at 56 ° C for 1 hour. Next, the produced inorganic salt was filtered off, the filtrate was concentrated under reduced pressure, and 100 ml of toluene was added to the residue.
Was added and washed with water.

After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 15.3 g of pale yellow crystals. Recrystallization from a mixed solvent of hexane and acetone gave the title compound as crystals with a melting point of 68-69 ° C (yield 12.9.
g, yield 80%).

Example 2 1- (Dinormal propylcarbamoyl) -3- (4
Preparation of 5-dimethyl-thiazol-2-yl) -sulfinyl-1,2,4-triazole (Compound No. 80) 1- (Dinormalpropylcarbamoyl) -3- (4
5-dimethyl-thiazol-2-yl) -thio-1,
Chloroform 100 was added to 6.8 g of 2,4-triazole.
Dissolve in ml, metachloroperbenzoic acid (content 70%)
5.4 g was added, and the mixture was stirred at 20 ° C. for 1 hour. After this 20
% Aqueous solution of potassium carbonate, and then three times with saturated saline.

After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure to give the title compound as pale yellow crystals.
0 g (yield 98%, melting point 63-64 ° C.) was obtained.

Example 3. Preparation of 1- (diethylcarbamoyl) -3- (4-methyl-thiazol-2-yl) -sulfonyl-1,2,4-triazole (Compound No. 5) 1- (diethylcarbamoyl) -3- (4-methyl 3.0 g of -thiazol-2-yl) -thio-1,2,4-triazole was dissolved in 100 ml of chloroform, and metachloroperbenzoic acid (content 70%) was added. The mixture was stirred at 20 ° C for 1 hour and then at 61 ° C for 2 hours. 20 after cooling
The solution was washed 3 times with a potassium carbonate aqueous solution at 0 ° C and then twice with a saturated saline solution.

After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 3.2 g of pale yellow crystals. This crystal is recrystallized from toluene and has a melting point of 124 to 125 ° C.
To obtain the title compound (yield 2.8 g, yield 85%).

Example 4. 1- (diethylcarbamoyl) -3- (4-phenyl-
Preparation of thiazol-2-yl) -sulfonyl-1,2,4-triazole (Compound No. 65) 3- (4-phenyl-thiazol-2-yl) -sulfonyl-1,2,4-triazole 2.9 g It was dissolved in 80 ml of acetone, 1.5 g of potassium carbonate and 1.5 g of diethylcarbamoyl chloride were added, and the mixture was stirred at 56 ° C. for 1 hour and 30 minutes. After cooling, the inorganic salt was filtered off, the filtrate was concentrated under reduced pressure, and 100 ml of toluene was added to the residue and washed with water.

After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain 3.8 g of pale yellow crystals. This is n
-Washing with hexane gives the title compound, mp 114.5.
It was obtained as crystals (yield 3.5 g, yield 90%) at -115.5 ° C.

Reference Production Example 1. 3- (4-methylthiazol-2-yl) -thio-1,
Preparation of 2,4-triazole 13.1 g of 2-mercapto-1,2,4-triazole
Dissolved in 90 ml of dimethylformamide,
With cooling to 11.5 g of sodium hydride (6 in mineral oil
0%) was gradually added. Then, the mixture was stirred for 30 minutes under cooling. After stirring, 13.4 g of 2-chloro-4-methylthiazole was added, and the mixture was stirred at room temperature for 30 minutes, and then 140-.
The mixture was stirred at 153 ° C for 2 hours. After cooling, 200 ml of water was added, extracted with 100 ml of ethyl acetate three times, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 18.5 g of pale yellow crystals, which were washed with n-hexane to give the title compound as crystals having a melting point of 115-116 ° C (yield 17.2).
g, yield 89%).

Example (Method for formulating herbicide) When the compound of the present invention is used as an active ingredient of a herbicide,
Usually, it is mixed with solid carrier, liquid carrier, surfactant, and other auxiliaries for preparations, and emulsions, wettable powders, liquids, flowable (sol) agents, powders, driftless agents, granules, and fine particles are prepared by a conventional formulation. It can be prepared in an appropriate form such as an agent or a tablet.

The carrier used here may be either solid or liquid as long as it is commonly used for agricultural and horticultural chemicals, and is not limited to a particular one. , For example, as these carriers, mineral powder (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate,
Apatite, white carbon, slaked lime, silica sand, ammonium sulfate, urea, etc., vegetable powder (soybean flour, wheat flour, wood flour, tobacco powder, starch, crystalline cellulose, etc.), polymer compound (petroleum resin, polyvinyl chloride, Ketone resin, dammal gum, etc.), alumina, silicates, sugar polymers, highly dispersible silicic acid, waxes and the like. Further, as the liquid carrier, water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, iso-propyl alcohol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene,
Benzene, xylene, ethylbenzene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, monochlorobenzene, trichlorofluoromethane, dichlorofluoromethane, etc.), ethers (ethyl ether, Ethylene oxide, dioxane, tetrahydrofuran, etc.),
Ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyryl ketone, isophorone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), nitriles (Acetonitrile, propionitrile, acrylonitrile, etc.), Sulfoxides (dimethyl sulfoxide, etc.), Alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), Aliphatic or alicyclic hydrocarbons (n-hexane) , Cyclohexane, etc.), industrial gasoline (petroleum ether, solvent naphtha, etc.), petroleum fraction (paraffins, kerosene, gas oil, etc.) and the like.

In the preparation of emulsions, wettable powders, flowable agents, etc., various surfactants (or emulsifiers) are used for the purpose of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading and the like. . Such surfactants include nonionic type (polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester, etc.), anionic type (alkylbenzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polysulfate). Oxyethylene alkyl sulfate, aryl sulfonate, etc.), cationic type [alkyl amines (lauryl amine, stearyl trimethyl ammonium chloride, alkyl dimethyl benzyl ammonium chloride, etc.), polyoxyethylene alkyl amines], amphoteric type [carboxylic acid (betaine type ), Sulfate ester salts, etc.]
Of course, it is not limited to these examples.

In addition to these, polyvinyl alcohol (PVA), carboxymethyl cellulose (CMC),
Various auxiliary agents such as gum arabic, polyvinyl acetate, sodium alginate, gelatin and tragacanth gum can be used.

In the present invention, when the above-mentioned various preparations are produced, the compound of the present invention is added in an amount of 0.001% to 95%.
(% By weight; the same applies hereinafter), preferably 0.01% to 90%
It can be formulated so as to contain in the range of. For example, in the case of powder, DL powder, and fine powder (F),
0.01% to 5%, in the case of granules 0.01% to 10%
%, Wettable powders, emulsions, and liquid preparations can be contained in the range of 1% to 75%.

In the case of granules, for example, the thus-prepared preparation may be sprayed as it is on the soil surface, in the soil or in water in an amount of about 0.3 to 300 g per 10 are as an active ingredient amount. In the case of a wettable powder, an emulsion, a sol and the like, it may be diluted with water or a suitable solvent and diluted in the range of about 0.3 to 300 g per 10 are as the active ingredient.

When the compound of the present invention is used as a herbicide, its applicability can be expanded by mixing it with a known herbicide, insecticide or plant regulator, and in some cases, a synergistic effect is expected. You can also do it.

Regarding the method for formulating the compound of the present invention represented by the general formula (1) as a herbicide, the following Examples 5 to 8 are given.
Explain. However, the present invention is not limited only to these examples, it can be mixed with various other additives in any proportion, and other herbicides and the like can be mixed in any proportion to prepare a formulation. You can also

Compound No. Are shown in Tables 1 to 5 above, and all parts in the examples are parts by weight.

Example 5 (Granule) Compound No. Compound 1 of 5, lauryl sulphate 1 part, calcium lignin sulfonate 1 part, bentonite 30 parts and white clay 67 parts were added with 15 parts of water and kneaded with a kneader, then granulated with a granulator, and then fluidized dryer. And dried to obtain granules containing 1% of active ingredient.

Example 6 (Wettable powder) Compound No. 7 parts 15 parts, white carbon
15 parts, calcium lignin sulfonate 3 parts, polyoxyethylene nonylphenyl ether 2 parts, diatomaceous earth
5 parts of clay and 60 parts of clay are uniformly mixed with a pulverizing mixer to obtain a wettable powder containing 15% of an active ingredient.

Example 7 (Emulsion) Compound No. 37 compounds 20 parts, Solpol 700
20 parts of H (Emulsifier manufactured by Toho Chemical Industry Co., Ltd.) and 60 parts of xylene are mixed to obtain an emulsion containing 20% of the active ingredient.

Example 8 (powder) Compound No. Compound No. 43 (0.5 parts), silicic acid fine powder (0.5 parts), calcium stearate (0.5 parts), clay (50 parts) and talc (48.5 parts) were uniformly mixed and pulverized to obtain a dust containing 0.5% of the active ingredient. obtain.

Next, Test Examples 1 to 3 are shown to illustrate the herbicidal effect of the compound of the present invention. Test Example 1. Herbicidal effect test and phytotoxicity test for transplanted paddy rice A plastic pot with a size of 1/5000 are is filled with paddy soil (planting loam soil), water is added for scavenging, and 50 Tainubier seeds are sown to the surface layer of 0-2 cm. Then
Two-leaf stage paddy rice was planted at a depth of 2 cm, 2 plants per strain, 3 plants per pot, and the water depth was kept at 3 cm.

The drug treatment was carried out in Example 2 in the 2 leaf stage of Tainubie.
Dilute the emulsion prepared in accordance with the procedure of 1.
ml (1.3g per are in terms of the amount of active ingredient used)
(Equivalent) was added dropwise.

This test was carried out in duplicate for each drug solution concentration group, and 21 days after drug treatment, the herbicidal effect and the phytotoxicity of paddy rice were investigated based on the following evaluation indexes. The results are shown in Tables 6 to 10.

Evaluation value of herbicidal effect Herbicidal rate (%) 5 100% 4 80 to less than 100% 3 60 to less than 80% 2 40 to less than 60% 1 20 to less than 40% 0 less than 20% Evaluation of phytotoxicity 5 Death 4 Drug damage 3 Drug damage Medium 2 Drug damage 1 Drug damage Minor 0 Drug damage No

[0072]

[Table 6]

[0073]

[Table 7]

[0074]

[Table 8]

[0075]

[Table 9]

[0076]

[Table 10] Note) Comparative drugs A to E are shown below.

[0077]

[Chemical 15] (Compounds described in JP-A-3-90069)

[0078]

[Chemical 16] (Compounds described in JP-A-1-121279)

[0079]

[Chemical 17] (Compounds described in JP-A-1-106883)

[0080]

[Chemical 18] (Compounds described in JP-A-59-39880)

[0081]

[Chemical 19] [JP-A-3-99066 (European Patent Publication No. 422369)

Test Example 2. Herbicidal effect test for paddy field weeds and chemical damage test for transplanted paddy rice Paddy soil (planting soil) in a plastic pot of 1/5000 are
, And seeds of Taenia cinerea, broad-leaved weeds (Azena, Scutellaria, Mizochabe) and firefly were sown at a depth of 1-2 cm, 30 seeds each. One day after sowing, the water was flooded to keep the water depth at 2 cm. Three days after sowing, paddy rice at the 2.5 leaf stage was transplanted and grown in a greenhouse. One day after transplanting the paddy rice, 10 ml of a spray solution obtained by diluting the emulsion prepared according to Example 7 with water to a predetermined amount was dropped per pot.

This test was carried out in duplicate for each drug solution concentration group, and 21 days after the treatment, the herbicidal effect and the phytotoxicity of paddy rice were investigated based on the same evaluation indexes as in Test Example 1. The results are shown in Tables 11 to 15.

[0084]

[Table 11]

[0085]

[Table 12]

[0086]

[Table 13]

[0087]

[Table 14]

[0088]

[Table 15] Note) Comparative drugs A to E are the same as those in Tables 6 to 10.

Test Example 3 Herbicidal effect on upland weeds and phytotoxicity test on crops 1) Herbicidal effect test on weeds Field soil (alluvial loam soil) was packed in a biscuit pot with a size of 1/5000 are, and soil with a surface layer of 1 cm and messhiba. , 50 seeds of various kinds of weed seeds, such as Echinocola, Shiroza, Inubiyu, and Inushita were uniformly mixed, and the surface layer was lightly pressed. Two days after sowing, the emulsion prepared according to Example 7 was diluted with water, and 100 l of the treatment agent per 10 ares (corresponding to 100 g per 10 are in terms of application amount of active ingredient) was sprayed on the soil surface.

This test is carried out in a double system for each concentration of the chemical solution.
30 days after the chemical treatment, the herbicidal effect was investigated based on the same evaluation index as in Test Example 1.

2) Chemical damage test for crops Field soil (alluvial loam soil) was packed in a pot of 1 / 10,000 ares, and the seeds of each crop (5 soybeans, 5 corns, 10 beets, 10 rapeseed seeds) Wheat 10
The grains were sown in separate pots, and the surface layer was lightly pressed. One day after sowing, the emulsion prepared according to Formulation Example 3 was diluted with water, and 100 l of the treatment agent per 10 ares (corresponding to 100 g per 10 are of active ingredient) was sprayed on the soil surface.

This test is carried out in a double system for each concentration of the chemical solution.
30 days after the chemical treatment, the degree of phytotoxicity to each crop was investigated based on the same evaluation index as in Test Example 1. The results are shown in Tables 16 to 20.

[0093]

[Table 16]

[0094]

[Table 17]

[0095]

[Table 18]

[0096]

[Table 19]

[0097]

[Table 20] Note) Comparative drugs A to E are the same as those in Tables 6 to 10.

[0098]

INDUSTRIAL APPLICABILITY The compound of the present invention has an excellent herbicidal effect as compared with known similar compounds, and exhibits excellent selectivity between crops and weeds. That is, in flooding treatment of paddy fields, various weeds that are problematic, for example, grass weeds such as Taenia japonicus, azena, sedge grass, broad-leaved weeds such as Mizohakobe, tamagaya periwinkle, firefly, matsubai, cyperaceae weeds such as cyperaceae, eelweed, swordweed, urchin. It can act on a wide variety of plants and so on to almost completely weed it, and it does not cause any phytotoxicity to rice.

In addition, the compound of the present invention is a broad-leaved weed of buckwheat vines, purslanes, sanaetade, chickweed, white azaleas, acagate, nazuna, ichibi, marabaasaagao, etc., which are problematic in foliar treatment and soil treatment of upland fields, barnyardgrass, barnyardgrass, green locusts, Crabgrass, Poa annua, grass weeds such as oats, can be almost completely weeded against a wide variety of cyperaceae weeds such as pearl nuts, and corn, wheat, rice, soybean,
No chemical damage to major crops such as cotton and sugar beet.

In addition, there is no human toxicity or fish toxicity. Therefore, it can be used safely.

─────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] March 26, 1992

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0009

[Correction method] Change

[Correction content]

In the formula, R ₁ and R ₂ represent a lower alkyl group or a lower alkylene group which forms a ring with R ₁ and R _2, and X represents
It represents a halogen atom or a lower alkyl group, R ₃ represents a hydrogen atom or a lower alkyl group , and n represents 0, 1, or 2. However, when R ₃ is a hydrogen atom, m is
2 or 3 shows, when R ₃ is a lower alkyl group
Indicates 0, 1, 2 or 3.

[Procedure Amendment 2]

[Document name to be amended] Statement

[Name of item to be corrected] 0072

[Correction method] Change

[Correction content]

[0072]

[Table 6]

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Kazuo Hirayama             2385 Toda, Atsugi City, Kanagawa Prefecture (72) Inventor Hirokazu Yoshizawa             One claw at 2190 Toda, Atsugi City, Kanagawa Prefecture             Bar Heights 303

Claims (2)

[Claims] 1. A general formula: [In the formula, R ¹ and R ² are the same or different and each represents a lower alkyl group, a lower alkenyl group, or R ¹ and R ²
Represents a lower alkylene group forming a ring with and X and Y are
The same or different, a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a halogen atom,
Represents a cyano group, or represents a lower alkyl group or a phenyl group which may be substituted with a halogen atom, and n represents
Represents an integer of 0, 1, or 2. ] The novel triazole derivative shown by these. 2. A general formula: [In the formula, R ¹ and R ² are the same or different and each represents a lower alkyl group, a lower alkenyl group, or R ¹ and R ²
Represents a lower alkylene group forming a ring with and X and Y are
The same or different, a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a halogen atom,
Represents a cyano group, or represents a lower alkyl group or a phenyl group which may be substituted with a halogen atom, and n represents
Represents an integer of 0, 1, or 2. ] The herbicide characterized by containing the novel triazole derivative shown by these as an active ingredient.