JPH05140125A - Triazole derivative and herbicide - Google Patents

Abstract

PURPOSE:To provide a new compound having an excellent herbicidal potency and useful as a highly safe herbicide. CONSTITUTION:A compound of formula I (R<1>, R<2> are lower alkyl, lower alkenyl, or R<1> and R<2> form a saturated hetero ring together with N; R<3> is H, lower alkyl, phenyl, etc.; R<4>, R<5> are lower alkyl, lower alkenyl, or R<4> and R<5> are a lower alkylene for together forming a ring; n is 0-2), e.g. 1-(diethylcarbamoyl)-3-N-(2,6-diethyl)phenyl) carbamoylmethyl-thio-1,2,4-triazole. The compound of formula I is obtained by reacting a triazolesulfonyl chloride derivative of formula II with a carbamoyl halide of formula III (Z is halogen) in the presence of a hydrogen halide-removing agent (e.g. calcium carbonate) in a solvent (e.g. toluene-acetone) at 0-100 deg.C. The compound exhibits an excellent herbicidal effect against paddy field weeds, especially Echinochoa, at a low dose without giving damages to crops.

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.

Accordingly, the present invention is directed to the chemical industry and agriculture,
It is especially useful in the agrochemical manufacturing field.

[0003]

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

JP-A-59-39880

[Chemical 3] In the formula, R ₁ and R ₂ represent a lower alkyl group or a lower alkylene group forming a ring with R ₁ and R ₂ , X represents a halogen atom or a lower alkyl group, and R ₃ represents a hydrogen atom or a lower atom. It represents an alkyl group, and n represents 0, 1 or 2.
However, when R ₃ is a hydrogen atom, m is 1, 2 or 3
When R ₃ is a lower alkyl group, m is 0, 1, 2
Or 3 is shown.

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

[Chemical 4] In the formula, R ₁ and R _{2 each} represent an alkyl group, and R ₃ represents one or two nitrogen atoms and one oxygen atom which may be substituted with a halogen atom, a cyano group, an alkyl group or a phenyl group. Alternatively, it represents a 5-membered ring containing a sulfur atom, and n represents an integer of 0, 1 or 2.

[0006]

However, the compounds described in these documents (1) to (4) are not always satisfactory because they have insufficient herbicidal effect or cause phytotoxicity to crops as shown in the test examples below. It is hard to say what should be done. Therefore, there is a demand for the development of a herbicide that has few such defects.

Therefore, the present invention provides a novel compound having excellent herbicidal activity and safety, and a herbicide containing the same as an active ingredient.

[0008]

[Means for Solving the Problems] The inventors of the present invention have synthesized a number of triazole derivatives in order to achieve the above object, and have made earnest studies on their usefulness. as a result,
The novel triazole derivative represented by the following general formula (1) does not cause phytotoxicity to crops, and weeds in paddy fields,
In particular, it was found that the application of a low amount of the drug showed great herbicidal effect on the rice bark, which is a highly damaging weed in paddy fields.

Therefore, the gist of the first aspect of the present invention lies in the general formula (1)

[Chemical 5] [Wherein R ¹ and R ² are the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a phenyl group or an aralkyl group. Represents, or represents a phenyl group substituted with one or more groups selected from a halogen atom, a lower alkyl group and a lower alkoxy group, or R ¹ and R ² together with an adjacent nitrogen atom It may form a saturated heterocycle,
R ³ represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl group substituted with one or more groups selected from a halogen atom, a lower alkyl group and a lower alkoxy group, and R ⁴ and R ⁵ are the same or different and represent a lower alkyl group, a lower alkenyl group, or a lower alkylene group forming a ring of R ⁴ and R ^5, and n is 0,
Represents an integer of 1 or 2].

In the compound represented by the general formula (1),
In the formula, in the definition of R ¹ , R ² , R ³ , R ⁴ , and R ⁵ , in the case of a lower alkyl group, it has 1 to 6 carbon atoms and may be linear or branched, and for example, Methyl group, ethyl group,
Examples thereof include n-propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, hexyl group, and isohexyl group.

Further, in the definition of R ¹ , R ² , R ³ , R ⁴ and R ⁵ , a lower alkenyl group has 2 to 6 carbon atoms and has a vinyl group, a 1-propenyl group, an allyl group, Examples thereof include an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-pentenyl group and a 2-hexenyl group.

Further, the lower alkynyl group has 2 to 6 carbon atoms and includes ethynyl group, propargyl group, 1-propynyl group, butynyl group and the like.

Examples of the saturated heterocycle include pyrrolidino group, piperidino group, piperazino group, morpholino group and the like.

Further, in the definition of R ⁴ and R ⁵ , a lower alkylene group has a carbon number of 2 to 6 and may be linear or branched. For example, trimethylene group, 1-
Examples thereof include a methylethylene group, a tetramethylene group, a dimethylmethylene group, a pentamethylene group and a 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 compound of the general formula (1) of the present invention are shown in Tables 1-8.

The compound No. is also referred to in the following examples and test examples.

[0018]

[Table 1]

[0019]

[Table 2]

[0020]

[Table 3]

[0021]

[Table 4]

[0022]

[Table 5]

[0023]

[Table 6]

[0024]

[Table 7]

[0025]

[Table 8]

[0026]

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.

[Example] (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.

First, as a reaction method, a starting material is represented by the general formula (2):

[Chemical 6] (Wherein R ¹ , R ² , R ³ and n have the same meanings as described above) and the general formula (3)

[Chemical 7] (In the formula, R ⁴ and R ⁵ have the same meanings as described above, and Z represents a halogen atom.) By reacting a carbamoyl halide represented by the general formula (1)

[Chemical 8] The formula (1) represented by (wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and n represent the above meanings) is obtained.

In the above reaction, when the target 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 this may be oxidized if necessary.

The step of reacting the oxidized or unoxidized compound of the formula (2) with the compound of the 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 the 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. ..

As the solvent, hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran and dioxane,
Acetone, methyl ethyl ketone, ketone-based compounds such as cyclohexanone, ethyl acetate, acetonitrile,
Examples thereof include dimethylformamide, pyridine, dimethylsulfoxide, water and a suitable mixed solvent thereof.

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

The oxidizing step can be carried out, for example, by oxidizing with an oxidizing agent in a suitable solvent. Examples of the oxidizer used here include aromatic peracids such as metachloroperbenzoic acid, aliphatic peracids such as peracetic acid and pertrifluoroacetic acid, hydrogen peroxide, potassium permanganate, and inorganic oxides such as chromic acid. Agent. 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 9] (Wherein R ¹ , R ² and R ³ have the same meanings as described above, and W represents a halogen atom), and an α-haloacetic acid amide derivative represented by the general formula (5)

[Chemical 10] It can be produced by reacting with a compound represented by the formula (wherein M represents an alkali metal).

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

Example 1 1- (Diethylcarbamoyl) -3- (N-methoxymethyl-N- (2,6-diethyl) phenyl) carbamoylmethyl-thio-1,2,4-triazole (Compound No.
Preparation of 79) 3- (N-methoxymethyl-N- (2,6-diethyl)
Phenyl) carbamoylmethyl-thio-1,2,4-triazole (16.7 g) was dissolved in 80 ml of acetone, and potassium carbonate (7.6 g) and diethylcarbamoyl chloride (7.5 g) were dissolved.
g was added, and 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 200 ml of chloroform was added to the residue and washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 20.5 g of pale yellow crystals. Recrystallization from a toluene-acetone mixed solvent gave the title compound as crystals (yield 16.8 g, yield 78%) having a melting point of 80 to 82 ° C.

Example 2 1- (Dinormalpropylcarbamoyl) -3- (N-
(4-chloro) benzyl-N-methyl) carbamoylmethyl-sulfinyl-1,2,4-triazole (compound
No. 55) Production 1- (Dinormal propylcarbamoyl) -3- (N-
(4-Chloro) benzyl-N-methyl) carbamoylmethyl-thio-1,2,4-triazole (21.1 g) was dissolved in 200 ml of chloroform, and 12.4 g of metachloroperbenzoic acid (content 70%) was added. Stir for 1 hour. After that, it was washed with a 20% potassium carbonate aqueous solution three times and then with a saturated saline solution twice. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 22.0 g of the title compound as a brown oily substance. Purification by silica gel chromatography using a toluene-acetone mixed solvent gave a pale yellow oil n ²³ _D = 1.5637 (yield 20.9 g, 92%).

Example 3 1- (Diethylcarbamoyl) -3- (N-benzyl)
Carbamoyl (1-ethyl) -sulfonyl-1,2,4-
Preparation of triazole (Compound No. 28) 1- (diethylcarbamoyl) -3- (N-benzyl)
18.1 g of carbamoyl (1-ethyl) -thio-1,2,4-triazole was dissolved in 200 ml of chloroform, and 27.2 g of metachloroperbenzoic acid (content 70%) was added. The mixture was stirred at 20 ° C for 1 hour and then at 61 ° C for 2 hours.
After cooling, the mixture was washed with a 20% aqueous potassium carbonate solution three times and then with a saturated saline solution twice. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to yield 1 pale yellow crystal.
7.7 g was obtained. Recrystallization from a toluene-acetone mixed solvent gave the title compound as crystals with a melting point of 50 to 51.5 ° C. (yield 16.7 g, yield 85%).

Example 4 1- (Diethylcarbamoyl) -3- (N-benzyl-
N-isopropyl) carbamoylmethyl-sulfonyl-
Preparation of 1,2,4-triazole (Compound No. 37) 3- (N-benzyl-N-isopropyl) carbamoylmethyl-sulfonyl-1,2,4-triazole 16.1
g was dissolved in 160 ml of acetone and potassium carbonate 6.9
g, 6.8 g of diethylcarbamoyl chloride,
The mixture was stirred at 56 ° C for 90 minutes. After cooling, the inorganic salt was filtered off, the filtrate was concentrated under reduced pressure, and 200 ml of toluene was added to the residue and washed with water. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain 20.6 g of the title compound as a brown oily substance. Purification by silica gel chromatography using a toluene-acetic acid ethyl ester mixed solvent gave a pale yellow oil n ²³ _D = 1.4671 (yield 1
8.9 g, yield 90%) was obtained.

Reference Production Example 1 Production of 3- (N-benzyl) carbamoyl (1-ethyl) -thio-1,2,4-triazole 2-mercapto-1,2,4-triazole 13.1 g of 90 ml of dimethyl. It was dissolved in formamide, and 11.5 g of sodium hydride (60% in mineral oil) was gradually added under cooling to 10 ° C. After this, the mixture was stirred for 30 minutes under cooling. After stirring, 19.8 g of N- (benzyl) -1-chloropropionic acid amide was added, and the mixture was added at room temperature for 30 minutes.
It stirred at 40-153 degreeC for 2 hours. After cooling, 200 ml of water
Was added and extracted three times with 100 ml of ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 25.2 g of pale yellow crystals. When this is washed with n-hexane, the title compound has a melting point of 122-123.
Crystals at 5 ° C. (yield 23.4 g, yield 89%) were obtained.

[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 (sols), 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 carrier. 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 compounds (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, etc.) 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.), nitrites (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 distillation Minerals (paraffins, kerosene, light oil, etc.) are included.

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 types (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, etc.), anionic types (alkylbenzene sulfonates, alkyl sulfosuccinates, alkyl sulphates, polysulfates). 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 (betainic acid ), Sulfuric acid ester salt, etc.]
Of course, the present invention 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 manufactured, 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%,
In the case of a wettable powder, an emulsion, and a liquid preparation, it 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 g to 300 g per 10 ares 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 an 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 other various additives in any proportion, and other herbicides and the like can be mixed in any proportion to prepare a formulation. You can also

The compound Nos. Are shown in Tables 1 to 8 above, and all parts in the examples are parts by weight.

Example 5 (Granule) Compound No. 27, compound 1 part, lauryl sulfate
1 part, calcium lignin sulfonate 1 part, bentonite 30 parts and white clay 67 parts and water 15 parts were added and kneaded with a kneader, then granulated with a granulator and dried with a fluid dryer to give 1% of active ingredient. To obtain granules containing.

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

Example 7 (Emulsion) Compound No. 85, 20 parts, Solpol 700H
(Emulsifier manufactured by Toho Chemical Industry Co., Ltd.) 20 parts and 60 parts of xylene are mixed to obtain an emulsion containing 20% of the active ingredient.

Example 8 (powder) 0.5 part of compound No. 73, fine powder of silicic acid anhydride
5 parts, calcium stearate 0.5 parts, clay 50
Parts and 48.5 parts of talc are uniformly mixed and ground to obtain a powder containing 0.5% of the active ingredient.

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 Paddy soil (planting loam soil) was filled in a plastic pot with a size of 1/5000 are, and water was added to perform scavenging, and 50 Tainubier seeds were added to the surface layer of 0 to 2 cm. Sow and 2
Leaf-stage paddy rice was planted at a depth of 2 cm, 2 plants per plant, 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 the sea urchin.
Dilute the emulsion prepared in accordance with 1) with water and add 10 per pot.
ml (equivalent to 10 g per are in terms of the amount of active ingredient used) was added dropwise.

This test was carried out in duplicate for each drug concentration group, and 21 days after the 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 9 to 11.

[0061]Evaluation value of herbicidal effect Weeding 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 value of drug damage Degree of phytotoxicity  5 Death 4 Drug damage 3 Drug damage Medium 2 Drug damage 1 Drug damage 0 Minor drug damage 0

[0062]

[Table 9]

[0063]

[Table 10]

[0064]

[Table 11]

Note) As the comparative drug A and the comparative drug B, the following compounds were used. Comparative drug A:

[Chemical 11] (Compounds described in JP-A-59-39880) Comparative drug B:

[Chemical 12] [Compounds described in JP-A-3-99066]

Test Example 2. Herbicidal effect test on paddy field weeds and phytotoxicity test on transplanted paddy rice Paddy soil (planting loam) is filled in a plastic pot with a size of 1 / 5,000 are, and rice paddy, broad-leaved weeds (Azena, Scutellaria japonica, Mizochabe) and firefly seeds are filled. 30 seeds were sown at a depth of 1 to 2 cm. 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, the emulsion prepared according to Example 7 was diluted with water to a predetermined amount, and 10 ml was dropped per pot.

This test was carried out in duplicate for each chemical 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 index as in Test Example 1. The results are shown in Tables 12-14.

[0068]

[Table 12]

[0069]

[Table 13]

[0070]

[Table 14] Note) Comparative drugs A to B are the same as those in Tables 9 to 11.

Test Example 3. Herbicidal effect against upland weeds and phytotoxicity test against crops 1) Herbicidal effect test against weeds Weaving field soil (alluvial loam soil) is packed in a bisque pot with a size of 1/5000 are, and the soil of 1 cm surface layer and methicella, Enocologsa, Shiroza, 50 seeds of each kind of weed seeds, Inubiyu and Saturni, 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 liters of the treatment agent per 10 ares (corresponding to 100 g per 10 ares in terms of application amount of active ingredient) was sprayed on the soil surface.

This test was carried out in duplicate for each drug concentration group, and 30 days after the drug treatment, the herbicidal effect was investigated based on the same evaluation index as in Test Example 1. The results are shown in Tables 15-17.
It is as follows.

2) Chemical damage test for crops Field soil (alluvial loam soil) was filled in a pot of 1 / 10,000 are of unglazed pot, and seeds of each crop (5 soybeans, 5 corns, 10 beets, 10 rapeseed seeds). And wheat 1
0 grains were sown in separate pots, and the surface layer was lightly pressed. One day after sowing, the emulsion prepared according to Formulation Example 7 was diluted with water, and 100 liters of treatment agent per 10 ares (corresponding to 100 g per 10 ares of active ingredient) was sprayed on the soil surface.

This test was carried out in duplicate for each drug solution concentration group, and 30 days after the drug treatment, the degree of drug damage to each crop was investigated based on the same evaluation index as in Test Example 1. The results are shown in Tables 15 to 17.

[0075]

[Table 15]

[0076]

[Table 16]

[0077]

[Table 17] Note) Comparative drugs A to B are the same as those in Tables 9 to 11.

[0078]

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 the flooding treatment of paddy fields, various weeds that are problematic, for example, grass weeds such as Taenia japonicus, Azena, Scutellaria, broad-leaved weeds such as Mizohakobe, Tamagayatsuri, Firefly, matsubai, Cyperaceae weeds such as Mizugaya, eelweed, swordweed, swordweed. It can act on a wide variety of plants and so on and almost completely weed it, and it does not cause any phytotoxicity to paddy rice.

The compound of the present invention is also problematic in the treatment of foliage and soil in the upland field.
Broad-leaved weeds such as starfish, chickweed, white lobster, blue-spotted gall, tuna, velvetleaf, malaba morning glory, etc.
It can act on a wide range of grass weeds such as Enocorogusa, Mexican herb, Astragalus membranaceus, oats, and Cyperaceae weeds such as pearl nuts, and can almost completely weed, and further, corn, wheat, rice, soybean, rapeseed, beet, etc. No chemical damage to major crops.

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

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hirokazu Yoshizawa 1 Clover Heights 303, 2190 Toda, Atsugi City, Kanagawa Prefecture

Claims (2)

[Claims] 1. A general formula: [Wherein R ¹ and R ² are the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a phenyl group or an aralkyl group. Represents, or represents a phenyl group substituted with one or more groups selected from a halogen atom, a lower alkyl group and a lower alkoxy group, or R ¹ and R ² together with an adjacent nitrogen atom It may form a saturated heterocycle,
R ³ represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl group substituted with one or more groups selected from a halogen atom, a lower alkyl group and a lower alkoxy group, and R ⁴ and R ⁵ are the same or different and represent a lower alkyl group, a lower alkenyl group, or a lower alkylene group forming a ring of R ⁴ and R ^5, and n is 0,
Represents an integer of 1 or 2]. 2. A general formula: [Wherein R ¹ and R ² are the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a phenyl group or an aralkyl group. Represents, or represents a phenyl group substituted with one or more groups selected from a halogen atom, a lower alkyl group and a lower alkoxy group, or R ¹ and R ² together with an adjacent nitrogen atom It may form a saturated heterocycle,
R ³ represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl group substituted with one or more groups selected from a halogen atom, a lower alkyl group and a lower alkoxy group, and R ⁴ and R ⁵ are the same or different and represent a lower alkyl group, a lower alkenyl group, or a lower alkylene group forming a ring of R ⁴ and R ^5, and n is 0,
Representing an integer of 1 or 2], the herbicide containing a triazole derivative as an active ingredient.