JPH05140126A - Triazole derivative and herbicide - Google Patents

Abstract

PURPOSE:To provide a new triazole derivative having an excel lent herbicidal potency, exhibiting excellent selectivity between crops and weeds, highly safe for human, animals and crops, and useful as a herbicide for paddy rice and upland fields. CONSTITUTION:A compound of formula I [R<1> is phenyl or 2-thiazolyl which may be substituted with a lower alkyl; R<2> is 2-thiazolyl, 2-benzothiazolyl, 2- pyridinyl or 2-triadinyl which can have a substituent (e.g. lower alkyl, halogen, lower alkoxy, mono-di lower alkylamino, aralkylamino)], e.g. 1-(4-methoxy-6- methylpyrimidin-2-yl)-3-(2,4,6-trimethylbenzene sulfonyl)-1,2,4triazole. The compound can be produced by reacting a compound of formula II with a compound of formula R<2> (X is halogen, methanesulfonyl). The compound acts widely on various weeds and can substantially perfectly kill the weeds 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. Therefore, the present invention is useful in the chemical industry as well as agriculture, especially in the field of agrochemical manufacturing.

[0002]

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.

European Published Patent No. 246749

[Chemical 3] In the formula, R ¹ represents a heterocyclic group, R ² represents hydrogen or the like, R ³ represents a substituted or unsubstituted heterocyclic group, a benzheterocyclic group, an aryl group or an aralkyl group. Represents
R ⁴ represents hydrogen or the like.

European Published Patent No. 338465 Publication General formula

[Chemical 4] In the formula, A represents -S- or -CH = CH-, and R ¹
Represents halogen, methyl, trifluoromethyl, methoxy, difluoromethoxy, nitro or methoxycarbonyl, R ² represents hydrogen, halogen, methyl, methoxy, allyloxy or propargyloxy, R 2
³ represents hydrogen or methyl, R ⁴ represents hydrogen, methyl or methoxymethyl, and R ⁵ represents C ₁ -C ₄ alkyl.

German Patent Application No. 3813886 General formula

[Chemical 5] In the formula, Ar represents a substituted or unsubstituted phenyl group, a pyridyl group, a pyrazolyl group, a thienyl group, R ¹ represents hydrogen, an aralkyl group, or the like, and R ² and R ³ are substituted or unsubstituted C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group,
C ₂ -C ₆ alkynyl group, a halogen, an alkoxy group, and alkylamino group.

European Published Patent No. 417875

[Chemical 6] In the formula, R ¹ represents methyl or the like, and R ² represents methyl or methoxy. However, when R ² represents methoxy, R ¹
Is not methyl.

[0007]

However, the compounds described in these documents (1) to (4) have insufficient herbicidal efficacy or cause phytotoxicity to crops, as shown in the test examples described below. It is hard to say that it should be satisfied. Therefore, there is a demand for the development of a herbicide with less such defects.

Therefore, the present invention is to provide a novel compound having excellent herbicidal activity and safety, and a herbicide for paddy rice and field action which contains the compound as an active ingredient.

[0009]

[Means for Solving the Problems] In order to achieve the above-mentioned object, the present inventors synthesized a number of triazole derivatives and conducted extensive studies on their usefulness. as a result,
It has been found that the novel triazole derivative represented by the following general formula (1) has an excellent herbicidal effect on weeds of paddy fields, especially on the paddy field weaver, which is a highly damaging weeds of paddy fields, without damaging the crops. ..

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

[Chemical 7] [In the formula, R ¹ represents a phenyl group, a 2-thiazolyl group, or a phenyl group substituted with a lower alkyl group, 2
Represents a thiazolyl group, R ² represents a ² -thiazolyl group, 2
-Represents a benzothiazolyl group, a 2-pyrimidinyl group, a 2-triazinyl group, or is substituted with a group selected from a lower alkyl group, a halogen atom, a lower alkoxy group, a lower alkylamino group, a di-lower alkylamino group and an aralkylamino group. Represented by the formula: 2-thiazolyl group, 2-benzothiazolyl group, 2-pyrimidinyl group, 2-triazinyl group].

In the compound represented by the general formula (1),
In the definition of R ¹ and R ^{2 in} the formula, the lower alkyl group has 1 to 6 carbon atoms and may be linear or branched, and examples thereof include methyl group, ethyl group and n-propyl group. Group, isopropyl group, n-butyl group, isobutyl group, se
A c-butyl group, a t-butyl group, a neopentyl group, an isohexyl group and the like can be mentioned.

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

Representative examples of the compound of the general formula (1) of the present invention are shown in Tables 1 to 4.

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

[0015]

[Table 1]

[0016]

[Table 2]

[0017]

[Table 3]

[0018]

[Table 4]

[0019]

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.

[Examples] (Method for producing the compound of the present invention) Next, the method for producing 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 8] (Wherein R ¹ represents the above meaning) and a triazole derivative represented by the general formula (3) R ² X (3) (wherein R ² represents the same meaning as described above, X represents a halogen atom, A heterocyclic compound represented by the formula (1)

[Chemical 9] The compound of the present invention represented by the formula (wherein R ¹ and R ² have the same meanings as described above) is obtained.

The step of reacting the compound of formula (2) with the compound of formula (3) is carried out in the presence of 1 equivalent or more, preferably 1 to 2 equivalents of a base, relative to the compound of formula (2), in a suitable solvent. Two
An equivalent amount, preferably 1 to 1.2 equivalents of the compound of formula (3) is reacted. In this case, the reaction temperature is 0 to 150 ° C.

As the base used, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Examples thereof include inorganic bases such as sodium hydride, and alkoxides such as potassium t-butoxide and sodium methoxide.

Examples of the solvent include hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, tetrahydrofuran and dioxane, acetonitrile,
Dimethylformamide, pyridine, dimethylsulfoxide, water or a suitable mixed solvent thereof can be used.

After completion of the reaction, the solvent is distilled off under reduced pressure, or water is directly added to the reaction solution for extraction with an organic solvent, or the organic solvent extraction solution is concentrated, and post-treatments are carried out, if necessary. It can also be purified by procedures such as chromatography, recrystallization and the like. An example of production by this method is shown in Example 1.

The starting material, the triazole derivative represented by the general formula (2), can be easily synthesized by a known method or a known method.

Further, in the general formula (1), when R ² is a 2-triazinyl group, it can also be produced by the method represented by the following formula.

[0028]

[Chemical 10] That is, a triazine derivative represented by the general formula (4) (wherein R ¹ has the same meaning as described above, and R ³ and R ⁴ represent hydrogen, a lower alkyl group or an aralkyl group), and a triazine derivative represented by the formula (5)
By reacting an amine represented by the formula (wherein R ⁵ and R ⁶ represent hydrogen, a lower alkyl group or an aralkyl group), the compound represented by the general formula (1 ′) (in the formula, R ¹ , R ³ , R ⁴ and R ⁵ , R ⁶ has the same meaning as described above).

The step of reacting the compound of formula (4) with the compound of formula (5) is carried out in the presence of 1 equivalent or more, preferably 1 to 2 equivalents of a base with respect to the compound of formula (4) in a suitable solvent. Two
An equivalent amount, preferably 1 to 1.2 equivalents of the compound of formula (5) is reacted. In this case, the reaction temperature is 0 to 150 ° C.

As the base used, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Examples thereof include inorganic bases such as sodium hydrogen carbonate and sodium hydride, and organic bases such as triethylamine, pyridine and N, N-diethylaniline.

As the solvent, benzene, toluene,
Hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran and dioxane, ketones such as acetone and methyl ethyl ketone, and acetonitrile, dimethylformamide, dimethylsulfoxide, pyridine , A solvent such as water, and an appropriate mixed solvent thereof can be used.

After completion of the reaction, post-treatment such as adding water to the reaction solution and extracting with an organic solvent or concentrating the organic solvent extraction solution is carried out, and if necessary, purification is carried out by operations such as chromatography and recrystallization. You can also do it. An example of production by this method is shown in Example 2.

The starting material for this reaction is represented by the formula (4)
The compound is a novel compound and has the general formula (2)

[Chemical 11] (Wherein R ¹ has the same meaning as described above) and the general formula (7)

[Chemical 12] (In the formula, R ³ and R ⁴ have the same meanings as described above, and X represents a halogen atom), and the compound can be produced by reacting the triazine derivative in the presence of a suitable base.

The compound of formula (7) which is a triazine derivative is publicly known. Reference Production Example 1 shows a production example of the compound of formula (4) as a starting material.

Example 1 1- (4-Methoxy-6-methylpyrimidin-2-yl)
-3- (2,4,6-trimethylbenzenesulfonyl)-
Production of 1,2,4-triazole (Compound No. 1) 3- (2,4,6-Trimethylbenzenesulfonyl)-
To a mixture of 5.0 g of 1,2,4-triazole, 60 ml of dimethyl sulfoxide and 3.6 g of anhydrous potassium carbonate,
2-Methanesulfonyl-4-methoxy-6-methylpyrimidine (5 g) was added, and the mixture was stirred at 100 ° C for 1 hr. After this, add 150 ml of water and extract with 100 ml of chloroform,
After washing with water, it was dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 7 g of colorless crude crystals.
This was recrystallized from ethanol to give the title compound as crystals with a melting point of 198 to 199 ° C (yield 5.6 g, yield 75%).
Was obtained as.

Example 2 3- (4-t-butylthiazol-2-yl) -sulfonyl-1- [4,6-bis (isopropylamino) -1,
Preparation of 3,5-triazin-2-yl] -1,2,4-triazole (Compound No. 16) 4,6-bis [(4-t-butylthiazol-2-yl) -sulfonyl-1,2 , 4-Triazol-1-yl] -2-isopropylaminotriazine 13.6 g
2.8 g of anhydrous potassium carbonate was added to a mixture of 1.2 g of isopropylamine and 80 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. After stirring, toluene 12
0 ml and 50 ml of water were added to separate the layers, and the organic layer was added to 0.5N.
It was washed with hydrochloric acid, then with water, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 9.0 g of colorless crude crystals. When this was recrystallized from a mixed solvent of toluene and n-hexane, the title compound had a melting point of 80-8.
It was obtained as crystals at 6 ° C. (yield 7.4 g, yield 80%).

Reference Production Example 1 2- (α, α-Dimethylbenzylamino) -4,6-bis (2,4,6-trimethylbenzenesulfonyl-1,2,4
Preparation of -triazol-1-yl) triazine 2- (α, α-dimethylbenzylamino) -4,6-dichlorotriazine 2.8 g, 3- (2,4,6-trimethylbenzenesulfonyl) -1,2, 4-triazole 4.8
3.6 g of anhydrous potassium carbonate was added to a mixture of g and 50 ml of dimethylformamide, and the mixture was stirred at 60 ° C. for 1 hour. The reaction solution was cooled, 100 ml of water was added, extracted with 100 ml of chloroform, washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 6.8 g of light brown crude crystals. This was recrystallized from toluene and n-hexane to give the title compound as colorless crystals (yield 4.8 g, yield 70%) having a melting point of 126 to 131 ° C.

[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 agents, 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 (betaine type ), 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 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%,
In the case of a wettable powder, an emulsion, and a liquid preparation, it can be contained in the range of 1% to 75%.

For example, in the case of granules, the preparation thus prepared 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 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 increased 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 3 to 6 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 4 above, and all parts in the examples are parts by weight.

Example 3 (Granule) 1 part of the compound of compound No. 5, lauryl sulfate 1
Water, 1 part calcium lignin sulfonate, 30 parts bentonite and 67 parts white clay were mixed with 15 parts water and kneaded with a kneader, then granulated with a granulator and dried with a fluid dryer to obtain 1% of the active ingredient. Obtain the containing granules.

Example 4 (Wettable powder) 15 parts of compound No. 2 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 pulverizer to obtain a wettable powder containing 15% of the active ingredient.

Example 5 (emulsion) Compound No. 14 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 6 (powder) 0.5 part of the compound of compound No. 16, 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 dust 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 the second leaf stage of the sea bream Example 5
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 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 Table 5.

[0055]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%

[0056]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

[0057]

[Table 5]

The following agents were used as the comparative agents A to D. Comparative drug A:

[Chemical 13] (Compounds described in European Patent Publication No. 246749)

Comparative drug B:

[Chemical 14] (Compound described in European Patent Publication No. 338465)

Comparative drug C:

[Chemical 15] (Compound described in German Patent Application No. 3813886)

Comparative drug D:

[Chemical 16] (Compound described in European Patent Publication No. 417875)

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 of paddy rice, 10 ml of a spray solution obtained by diluting the emulsion prepared according to Example 5 with water to a predetermined amount was obtained.
Dropped.

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 indexes as in Test Example 1. The results are shown in Table 6.

[0064]

[Table 6] Note) Comparative drugs A to D are the same as in Table 5.

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 seeding, the emulsion prepared according to Example 5 was diluted with water, and 100 liters per 10 ares (corresponding to 100 g per 10 ares in terms of application amount of active ingredient) was sprayed onto 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 Table 7.

2) Chemical damage test for crops Field soil (alluvial loam soil) was packed in a pot of 1 / 10,000 are unglazed, 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 Example 5 was diluted with water, and 100 liters per 10 ares (corresponding to 100 g per 10 ares in active ingredient amount) was sprayed onto the soil surface.

This test was carried out in duplicate for each chemical concentration group, and 30 days after the chemical treatment, the degree of chemical damage to each crop was investigated based on the same evaluation index as in Test Example 1. The results are shown in Table 7.

[0069]

[Table 7] Note) Comparative drugs A to D are the same as in Table 5.

[0070]

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, yellow grass, broad-leaved weeds such as Mizochabe,
It can act on a wide variety of cyperaceous weeds, such as Pleurotus cornucopia, firefly, pine nuts, cyperus edulis, etc., konagi, urine and so on, and can almost completely weed it, and it does not cause any phytotoxicity to paddy rice.

Further, the compound of the present invention is a broad-leaved weed such as Acacia nilothus, Acacia catechu, Acacia catechu, Rhododendron, Prunus chinensis, Malva morning glory, etc. which are problematic in foliar treatment and soil treatment of upland fields. , Crabgrass, Blue-spotted caterpillar,
It can act on a wide range of grass weeds such as oats and cyperaceae weeds such as pearl nuts, and can almost completely weed it, and in addition, corn, wheat, rice,
No chemical damage to major crops such as soybean, rapeseed and beet.

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

Continuation of the front page (51) Int.Cl. ⁵ Identification number Reference number within the agency FI Technical indication location C07D 417/12 249 9051-4C 417/14 249 9051-4C (72) Inventor Masayuki Kusu 2385 Toda, Atsugi, Kanagawa Prefecture Address Hokuko Kagaku Dormitory (72) Inventor Hirokazu Yoshizawa 1 Clover Heights 303, 2190 Toda, Atsugi City, Kanagawa Prefecture

Claims (2)

[Claims] 1. A general formula: [In the formula, R ¹ represents a phenyl group, a 2-thiazolyl group, or a phenyl group substituted with a lower alkyl group, 2
Represents a thiazolyl group, R ² represents a ² -thiazolyl group, 2
-Represents a benzothiazolyl group, a 2-pyrimidinyl group, a 2-triazinyl group, or is substituted with a group selected from a lower alkyl group, a halogen atom, a lower alkoxy group, a lower alkylamino group, a di-lower alkylamino group and an aralkylamino group. Represents a 2-thiazolyl group, a 2-benzothiazolyl group, a 2-pyrimidinyl group, or a 2-triazinyl group.]. 2. A general formula: [In the formula, R ¹ represents a phenyl group, a 2-thiazolyl group, or a phenyl group substituted with a lower alkyl group, 2
Represents a thiazolyl group, R ² represents a ² -thiazolyl group, 2
-Represents a benzothiazolyl group, a 2-pyrimidinyl group, a 2-triazinyl group, or is substituted with a group selected from a lower alkyl group, a halogen atom, a lower alkoxy group, a lower alkylamino group, a di-lower alkylamino group and an aralkylamino group. Representing a 2-thiazolyl group, a 2-benzothiazolyl group, a 2-pyrimidinyl group, or a 2-triazinyl group], the active ingredient is a herbicide.