JPH05286969A - Thienyl-azolyl-oxyacetamide derivative, its production and herbicide containing the same - Google Patents

Abstract

PURPOSE:To obtain the subject novel compound which has strong herbicidal activity against grown barnyard grass and is useful as a herbicide having selectivity between rice plant and barnyard grasses with high safety. CONSTITUTION:A compound of formula I [X is O, S; R is H, alkyl, halogen; R<1> is alkyl, cycloalkyl, (substituted)phenylalkyl, (substituted)phenyl; R<2> is alkyl, cycloalkyl, (substituted)phenyl or R<1> and R<2> form a cyclic amino group together with the N atom], for example, N-methyl-N-phenyl-2-[5-(2-thienyl)-1,3,4- thiadiazol-2-yloxy]-acetamide. The compound of formula I is obtained by reaction of an azole derivative of formula II (Y is halogen, methylsulfonyl) and a hydroxyacetamide derivative of formula III.

Description

Detailed Description of the Invention

[0001]

The present invention relates to the general formula (I)

[0002]

[Chemical 6] [In the formula, indicates that the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. , R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a substituent Optionally having a phenylalkyl group or a phenyl group (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or 1-naphthyl represents a group, or R ¹ and R ² represents a cyclic amino group which forms together with the nitrogen atom to which they are attached In represented by thienyl - azolyl - oxyacetamide derivatives (hereinafter, referred to as present compound), to a herbicide which is characterized by containing the preparation and said compounds as an active ingredient.

[0003]

2. Description of the Related Art It has already been disclosed that certain azolyl-oxyacetamide compounds have herbicidal activity. In particular, if the compounds related to the compound of the present invention are mentioned,
For example: (1) JP-A-55-147267

[0004]

[Chemical 7] (R represents a 5-membered hetero-aromatic monocyclic group) (2) JP-A-57-95974

[0005]

[Chemical 8] (3) JP-A-58-206578

[0006]

[Chemical 9] (4) JP-A-2-45403

[0007]

[Chemical 10] However, the herbicidal activity and safety of these known compounds against paddy rice are not always satisfactory.

[0008]

In recent years, it has been desired to develop a herbicide having a strong herbicidal activity and selectivity for useful crops. In the paddy field, a strong herbicidal effect is exerted especially on the advanced Nobie. There is a demand for the development of a herbicide that has activity and at the same time is highly safe for paddy rice.

The object of the present invention is to provide a novel herbicide that solves these problems.

[0010]

Means and Actions for Solving the Problems The inventors of the present invention have conducted earnest researches on the azolyloxyacetamide derivative in order to solve the above problems, and as a result, the compound of the present invention is a particularly harmful weed in paddy fields. The present invention has been completed by discovering the excellent characteristics that it exhibits a strong herbicidal activity against Nobies at the time of germination and advanced growth, and at the same time has a high safety against paddy rice.

That is, the present invention provides (1) the general formula (I)

[0012]

[Chemical 11] [In the formula, indicates that the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. , R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a substituent Optionally having a phenylalkyl group or a phenyl group (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or 1-naphthyl represents a group, or R ¹ and R ² represents a cyclic amino group which forms together with the nitrogen atom to which they are attached In represented by thienyl - azolyl - oxyacetamide derivatives, (2) the general formula (II)

[0013]

[Chemical 12] (In the formula, the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X is an oxygen atom or a sulfur atom, Y is a halogen atom or a methylsulfonyl group, and R is a hydrogen atom. , An alkyl group, an alkoxy group or a halogen atom) and a general formula (III)

[0014]

[Chemical 13] [In the formula, R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group. A phenylalkyl group or a phenyl group which may have a substituent (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or A 1-naphthyl group, or R ¹ and R ² represent a cyclic amino group formed together with the nitrogen atom to which they are bonded], and a hydroxyacetamide derivative represented by the general formula (I)

[0015]

[Chemical 14] (Wherein, X, R, R ¹ , R ² and the bonding position of the thiophene ring have the same meanings as described above).
A method for producing an azolyl-oxyacetamide derivative,

(3) General formula (I)

[0017]

[Chemical 15] [In the formula, indicates that the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. , R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a substituent Optionally having a phenylalkyl group or a phenyl group (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or 1-naphthyl represents a group, or R ¹ and R ² represents a cyclic amino group which forms together with the nitrogen atom to which they are attached In represented by thienyl - azolyl - providing a herbicide characterized by containing the oxyacetamide derivatives as an active ingredient.

The compound of the present invention is a novel compound which was first synthesized by the present inventors and which has not been described in the literature. The general formula (I)
In the following, R, R ¹ and R ² will be described with reference to specific examples. Examples of the alkyl group of R include methyl and ethyl groups, examples of the alkoxy group include methoxy and ethoxy groups, and examples of the halogen atom include chlorine and bromine atoms. Examples of the alkyl group of R ¹ and R ² include a methyl group, ethyl group, propyl group, isopropyl group and butyl group, an alkenyl group includes an allyl group and a butenyl group, and an alkynyl group includes a propynyl group and a butynyl group. Examples of the cycloalkyl group include cyclopropyl, cyclopentyl and cyclohexyl groups, and the phenylalkyl group which may have a substituent includes benzyl,
2-chlorobenzyl, 4-fluorobenzyl, 2-methylbenzyl, 4-methoxybenzyl, 1- and 2-phenylethyl groups and the like can be mentioned.

The phenyl group of R ² (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) includes phenyl, 2-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-propylphenyl, 2-methoxyphenyl, 3
-Methoxyphenyl, 2-ethoxyphenyl, 3-isopropoxyphenyl, 2-allyloxyphenyl, 2-
Propargyloxyphenyl, 2-methylthiophenyl, 4-methylthiophenyl, 2-chlorophenyl, 4
-Chlorophenyl, 4-fluorophenyl, 2,3-dimethylphenyl, 2,5-dimethylphenyl, 3,4-
Dimethylphenyl, 2,6-dimethylphenyl, 2,3
-Dichlorophenyl, 2-methoxy-4-chlorophenyl, 2-methyl-5-chlorophenyl, 2,4,6-trimethylphenyl, 3-nitrophenyl group and the like. Further, R ¹ and R ² are, as a cyclic amino group formed together with the nitrogen atom to which they are bonded, pyrrolidyl, 2-methylpyrrolidyl, 2-methylpiperidyl, 2
-Ethyl piperidyl, morpholinyl, 3,5-dimethylmorpholinyl, perhydroazepinyl, 2,3-dihydroindolyl, 1,2,3,4-tetrahydroquinolyl group and the like.

The compound of the present invention can be produced by the method represented by the following reaction formula.

[0021]

[Chemical 16] (In the formula, the bonding positions of X, Y, R, R ¹ , R ² and the thiophene ring have the same meanings as described above.) Y in (II) represents a halogen atom or a methylsulfonyl group, and the halogen atom is chlorine. Atoms and bromine atoms are preferred, and the amount of (II) used is not particularly limited with respect to the oxyacetamide of (III), but it is usually performed in about equimolar amounts. The solvent is preferably an inert solvent, for example, ethers such as tetrahydrofuran, dioxane, glycol dimethyl ether, ketones such as acetone and methyl ethyl ketone, alcohols such as sec- and t-butanol, such as toluene and chlorobenzene. Aromatic hydrocarbons such as, for example, acetonitrile, nitriles such as propionitrile, such as dimethylformamide, dimethylacetamide, amides such as N-methylpyrrolidone, etc. can be used alone or in combination. ..

Examples of the basic substance include sodium hydroxide, potassium hydroxide, potassium carbonate, potassium-t-
Examples thereof include butoxide, sodium-t-butoxide, sodium hydride, triethylamine, diazabicycloundecene and the like, and the amount thereof is preferably an equimolar amount or a small excess with respect to oxyacetamide of (III). The reaction temperature can be arbitrarily set from low temperature to heating, and is usually -30 to 1
It is in the range of 00 ° C, preferably -20 to 80 ° C. The reaction time varies depending on the set conditions, but it can be usually completed in 2 to 10 hours.

The reaction product can be separated from the reaction mixture by a conventional method and, if desired, can be purified by recrystallization, column chromatography or the like.

[0024]

[Examples] The production methods of the compound of the present invention are described in detail below with reference to synthetic examples, but the present invention is not limited thereto.

Synthesis Example 1 N-methyl-N-phenyl-2- {5- (2-thienyl) -1,3,4-thiadiazol-2-yloxy}
-Preparation of acetamide 0.58 g of N-methyl-N-phenyl-2-hydroxyacetamide was dissolved in 10 ml of dimethylformamide and 0.39 g of potassium-t-butoxide was added under ice cooling, and then 2
0.71 g of -chloro-5- (2-thienyl) -1,3,4-thiadiazole was gradually added and reacted. After stirring at room temperature for about 5 hours, the mixture was poured into 150 ml of water, extracted with benzene, washed with water and dehydrated with anhydrous magnesium sulfate, and benzene was recovered under reduced pressure to obtain 0.92 g of a crude product as a residue. This was purified by silica gel chromatography to obtain 0.60 g of the desired product as white crystals. Melting point 105.5-107 ° C

Synthesis Example 2 N-ethyl-N-phenyl-2- {5- (2-thienyl) -1,3,4-thiadiazol-2-yloxy}
-Preparation of acetamide 0.59 g of N-ethyl-N-phenyl-2-hydroxyacetamide was dissolved in 10 ml of tetrahydrofuran, 0.20 g of sodium hydride (60%) was added under ice-cooling, and the mixture was stirred for 30 minutes. Chloro-5- (2-thienyl)-
0.61 g of 1,3,4-thiadiazole was gradually added, and then stirring was continued at 30 to 5 ° C for 3 hours. Next, the reaction product was poured into 200 ml of water, and the deposited precipitate was separated by filtration, washed with water and dried to obtain 0.74 g of a crude product. This was purified with benzene: hexane = 1: 1 to obtain 0.60 g of the desired product as white crystals. Melting point 122-124 ° C

Synthetic Examples 3 to 46 Reactions were carried out in the same manner as in Synthetic Examples 1 and 2 to produce the following compounds. The results are shown in Tables 1-7.

[0028]

[Chemical 17]

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

[0032]

[Table 4]

[0033]

[Table 5]

[0034]

[Table 6]

[0035]

[Table 7]

Synthesis Example 47 N-methyl-N-phenyl-2- {5- (2-thienyl) -1,3,4-thiadiazol-2-yloxy}
-Preparation of acetamide 0.90 g of N-methyl-N-phenyl-2-hydroxyacetamide and 1.25 g of 2-methylsulfonyl-5- (2-thienyl) -1,3,4-thiadiazole were dissolved in 15 ml of acetone, After cooling to about -10 ° C with ice and salt,
A solution prepared by dissolving 0.26 g of caustic soda in 1.0 ml of water was reacted dropwise. After continuing stirring at -5 to 0 ° C for 2 hours,
The crystals precipitated in 100 ml of water were filtered off, washed with water and dried to obtain 1.40 g of a crude product. This was purified with benzene-hexane to obtain 1.10 g of the desired product as white crystals. Melting point 106-107 ° C. The infrared absorption spectrum was completely the same as that of the compound obtained in Synthesis Example 1, and it was confirmed that the compounds were the same compound even if they were mixed and melted without a drop in melting point.

Synthesis Example 48 N-methyl-N-phenyl-2- {5- (3-thienyl) -1,3,4-thiadiazol-2-yloxy}
-Preparation of acetamide 0.85 g of N-methyl-N-phenyl-2-hydroxyacetamide and 1.25 g of 2-methanesulfonyl-5- (3-thienyl) -1,3,4-thiadiazole were added to 15 ml of acetone and 5 ml of dimethoxyethane. The product was dissolved in the above solution, and reacted and treated in the same manner as in Synthesis Example 47 to obtain 1.07 g of the desired product. Melting point 97-98 ° C

Synthesis Examples 49 to 51 The following compounds were produced by reacting in the same manner as in Synthesis Example 47. The results are shown in Table 8.

[0039]

[Chemical 18]

[0040]

[Table 8]

Numerical values of physical properties in Tables 1 to 8 represent melting points (° C.), IR was measured by the sandwich method and expressed in cm ⁻¹ , and H
-NMR was measured in CDCl _3, expressed in ppm. The compound of the present invention is safe with substantially no phytotoxicity to transplanted paddy rice as shown in the test examples below, and further, for example, No. 1
No. 3, No. 14, No. 39, etc. show high selectivity for direct-seeded paddy rice, and have strong herbicidal activity even at the germination stage and the advanced stage of growth of Novier, which is a weed-damaging weed. It is also a great feature that it has excellent characteristics that can be applied to direct seeding rice cultivation. Further, since the compound of the present invention has good selectivity for useful crops such as cotton, soybean and wheat, it can be applied to upland cultivation.

When the compound of the present invention is used as a herbicide, it may be used as it is, but generally, it is formulated into an emulsion, a wettable powder, a granule, a fine granule, a powder, a concentrated suspension, and the like. It is advantageous to use Liquid or solid carriers can be used in making these formulations. Examples of the liquid carrier include aromatic hydrocarbons such as toluene, xylene, chlorobenzene, dichlorobenzene and methylnaphthalene, alcohols such as ethylene glycol, butyl alcohol and cellosolve, ketones such as cyclohexanone and isophorone, dimethylformamide, N. -Methylpyrrolidone, vegetable oils, water and the like. Examples of the solid carrier include kaolin, talc, bentonite, diatomaceous earth, clay, and the like, and synthetic minerals such as alumina and silicate can also be used. In formulating, it is advantageous to use various auxiliary agents such as emulsifiers, dispersants, spreading agents, wetting agents, penetrating agents, etc. in order to impart characteristics such as emulsification, dispersion, suspension and penetration. ..

Examples of the emulsifier include nonionic ones such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether and polyoxyethylene-fatty acid ester, and anionic emulsifiers such as alkylaryl sulfonate and alkyl sulfate ester. Is mentioned. In addition, it can be used as a mixture with other herbicides for the purpose of reducing the spraying labor or for expanding the range of grass species that can be effectively controlled, which is a particularly effective means in practical situations.

The amount of the herbicide of the present invention to be used varies depending on the age of the leaves of the weeds at the time of treatment.
500g / 10 are, preferably 5-200g / 10
It is Earl. Next is shown a formulation example and a herbicidal activity test example of a herbicide containing the compound of the present invention as an active ingredient,
The present invention is of course not limited to these.
Parts indicate parts by weight.

Formulation Example 1 Isophorone (10 parts) and xylene (65 parts) were added to 20 parts of the compound, and polyoxyethylene alkyl ether (1.5 parts), alkylbenzene sulfonate (2 parts) and polyoxyethylene sorbitan alkylate (1.5 parts) were used as emulsifiers. Then, they were mixed and dissolved to obtain a 20% emulsion.

Formulation Example 2 30 parts of the compound of the present invention, 2 parts of sodium dialkylnaphthalene sulfonate, 3 parts of calcium lignin sulfonate and 65 parts of clay were well pulverized and mixed to obtain a 30% wettable powder. Formulation Example 3 25 parts of the compound of the present invention, 5 parts of polyoxyethylene sorbitan monooleate, 0.3 part of xanthan gum and water 69.
7 parts were mixed and wet-milled until the particle size of the compound of the present invention was 2 microns or less to obtain a 25% suspension agent.

Formulation Example 4 3 parts of the compound of the present invention, 68 parts of clay, and 25 parts of bentonite
Parts, sodium alkylbenzene sulfonate 0.5 parts and calcium lignin sulfonate 3.5 parts were added and mixed well. Water was added to this and kneaded well, granulated and dried to obtain 3% granules.

Test Example 1 Transplanted paddy rice Noby 2.0 leaf stage treatment test 1 / 5,000 a Wagner pot was filled with paddy soil and water
After scratching, seeds of Novier, firefly, yellow grass, eel, etc. were sown. Furthermore, two 2.5-leaf stage paddy rice plants were transplanted at a rate of 2 per 2 plants and grown at a submerged depth of 3 cm. When the Nobie was in the 2.0 leaf stage, the inundation depth was set to 4 cm, and a predetermined amount of the compound of the present invention adjusted according to the formulation example was diluted with water and treated dropwise on the water surface. Treated amount of active ingredient is 100g per 10 ares
And Then, 30 days after the drug treatment, an investigation was conducted according to the criteria shown in Table 9, and the results shown in Table 10 were obtained.

[0049] 1 of Table 10 ───────────────────────────── Synthetic example Herbicidal effect Herbicide damage No. ──────── ────────────────── Novier Firefly Squishy Konagi Paddy rice ───────────────────────────── ─ 3 5 5 5 5 5 1 4 5 5 5 5 5 1 5 5 5 5 5 5 5 1 6 5 5 5 5 5 1 7 5 5 5 5 5 1 8 5 5 5 5 5 1 9 5 5 5 5 5 1 10 5 5 5 5 5 5 5 5 5 5 1 12 5 5 5 5 5 1 13 5 5 5 5 5 1 14 5 5 5 5 5 1 16 5 5 5 5 5 1 17 5 5 5 5 5 1 20 5 5 5 5 5 1 27 4 5 5 5 5 2 28 5 5 5 5 1 ───────────────────────────── Table 2-2 ─────────────── ───────────────── Synthetic example Herbicidal effect Chemical damage No. ───────────────────────── NOVIE Firefly Squishy Konagi Paddy rice ───────────────────── ─────────── 31 5 5 5 5 5 1 32 5 5 5 5 5 1 33 5 5 5 5 5 1 34 5 5 5 5 5 1 35 5 5 5 5 5 1 36 5 5 5 5 5 1 37 5 5 5 5 1 38 5 5 5 5 5 1 39 5 5 5 5 5 1 40 5 5 5 5 5 1 42 5 5 5 5 5 1 43 5 5 5 5 5 1 44 5 5 5 5 5 1 49 5 5 5 5 5 1 50 5 5 5 5 5 5 1 51 5 5 5 5 1 Comparative agent A 5 5 5 5 1 Comparative agent B 5 5 5 5 5 Comparative agent C 5 5 5 5 1 1 ──────────────────── ──────────── Comparative agent A:

[0050]

[Chemical 19] Comparative agent B:

[0051]

[Chemical 20] Comparative agent C:

[0052]

[Chemical 21]

Test Example 2 Soil Treatment Test at Germination Stage Paddy soil was filled in a plastic pot having a surface area of 100 cm ² , 20 seeds of Novier seeds and 10 seeds of rice seeds were sown, and 0.5
The soil was covered to a thickness of cm. When the Nobie and paddy rice germinated on the surface of soil, the compound of the present invention was diluted with water to a depth of 4 cm, and the solution was added dropwise to the surface of the water. The treatment amount was 100 g per 10 ares of the active ingredient. Then, 21 days after the drug treatment, an investigation was conducted according to the criteria shown in Table 9, and the results shown in Table 11 were obtained.

Table 11 ────────────────────────────────── Synthetic example Herbicidal effect Chemical damage Synthetic example Herbicidal effect Chemical damage No. ─────────── No. ──────────── Novie paddy rice Novie paddy rice ───────────────────── ──────────── 5 5 1 37 5 5 1 12 5 1 38 5 5 1 13 5 1 39 5 1 14 5 1 40 5 1 16 5 1 43 5 1 32 5 2 50 5 5 2 33 5 2 Comparative Agent A 5 5 5 34 5 1 Comparative Agent B 5 5 36 5 2 Comparative Agent C 5 5 ───────────────────────────── ─────

Test Example 3 Novie 2.0 leaf stage treatment test In the same manner as in Test Example 2, Novier seeds and paddy rice seeds were sown in a plastic pot having a surface area of 100 cm ² , and allowed to grow to the 2.0 leaf stage. It was When the Nobie and paddy rice reached the 2.0 leaf stage, the water depth was 4 cm, and the compound of the present invention was diluted with water and added dropwise to the water surface. The treatment amount was 100 g per 10 ares of the active ingredient. Then, 21 days after the drug treatment, an investigation was conducted according to the criteria shown in Table 9, and the results shown in Table 12 were obtained.

Table 12 ────────────────────────────────── Synthetic example Herbicidal effect Chemical damage Synthetic example Herbicidal effect Chemical damage No. ─────────── No. ──────────── Novie paddy rice Novie paddy rice ───────────────────── ──────────── 3 5 1 32 4 4 1 4 5 1 33 5 5 1 5 5 1 34 4 2 6 5 2 35 5 1 7 5 5 2 36 5 1 1 9 5 1 37 5 5 1 10 5 2 39 5 1 11 5 5 1 40 5 5 1 12 5 1 42 5 1 13 5 1 43 5 5 1 14 5 1 44 5 1 16 5 5 1 49 4 1 17 5 5 1 50 5 1 20 5 1 51 5 5 1 28 5 1 Compare Agent A 5 1 31 5 1 Comparative agent B 5 5 Comparative agent C 5 1 ──────────────────────────────────

[0057]

EFFECTS OF THE INVENTION According to the present invention, it has extremely high selectivity between the rice and the genus Mussel and has a strong herbicidal activity, and has a suitable period of use from the rice germination stage to the millet 2.0 to 2.5 leaf stage. It is possible to obtain an excellent herbicide having a wide range.

Claims (3)

[Claims] 1. A compound represented by the general formula (I): [In the formula, indicates that the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. , R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a substituent Optionally having a phenylalkyl group or a phenyl group (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or 1-naphthyl represents a group, or R ¹ and R ² represents a cyclic amino group which forms together with the nitrogen atom to which they are attached In represented by thienyl - azolyl - oxyacetamide derivatives. 2. A compound represented by the general formula (II): (In the formula, the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X is an oxygen atom or a sulfur atom, Y is a halogen atom or a methylsulfonyl group, and R is a hydrogen atom. , An alkyl group, an alkoxy group or a halogen atom) and a general formula (III) [In the formula, R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group. A phenylalkyl group or a phenyl group which may have a substituent (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or A 1-naphthyl group, or R ¹ and R ² represent a cyclic amino group formed together with the nitrogen atom to which they are bonded], and a hydroxyacetamide derivative represented by the general formula (I) [Chemical 4] (Wherein, X, R, R ¹ , R ² and the bonding position of the thiophene ring have the same meanings as described above).
A method for producing an azolyl-oxyacetamide derivative. 3. A compound represented by the general formula (I): [In the formula, indicates that the 2- or 3-position of the thiophene ring is bonded to the azolyl ring, X represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. , R ¹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenylalkyl group which may have a substituent, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a substituent Optionally having a phenylalkyl group or a phenyl group (which may be substituted by an alkyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkylthio group, a halogen atom or a nitro group) or 1-naphthyl represents a group, or R ¹ and R ² represents a cyclic amino group which forms together with the nitrogen atom to which they are attached In represented by thienyl - azolyl - herbicides characterized by containing the oxyacetamide derivatives as an active ingredient.