JP2000063360A - Trifluoromethanesulfonylanilide derivative, its production and herbicide with the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having a wide spectrum of herbicidal activity at low doses, exhibiting significant effect on gramineous weeds among others and having high safety to mammals as well. SOLUTION: This new compound is a trifluoromethanesulfonylanilide derivative of formula I (R is an alkoxyalkyl), e.g. 2-[(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl]-6-methoxymethyltrifluoromethanesulfonylanilide. The compound of formula I is obtained by reaction of a trifluoromethanesulfonyl halide or trifluoromethanesulfonic acid anhydride with a 2-substituted aniline derivative of formula II followed by converting the product to the corresponding salt as desired. It is preferable that, in a herbicide with the compound of formula I as active ingredient, when it is to be used directly as in the form of powder or granules the herbicide is applied at 0.1 g to 5 kg, pref. 1 g to 1 kg, per 10 are in terms of the active ingredient.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel trifluoromethanesulfonylanilide derivative or a salt thereof, a method for producing the same, and a herbicide containing the same as an active ingredient.

[0002]

Heretofore, sulfonylanilide derivatives having a pyrimidinyl-containing group in the 2-position, for example N-trifluoromethanesulfonyl derivatives of 2-pyrimidinylmethyl-substituted or 2-pyrimidinyloxy- or thioxy-substituted anilines, have been found to have herbicidal activity. It is known (Japanese Patent Publication No. 7-501053, WO93 / 09099). It is also known that an N-trifluoromethanesulfonyl derivative of aniline having a pyrimidinylhydroxymethyl group at the 2-position of the phenyl group has a plant growth regulating action (WO96 / 41799). However, a sulfonylanilide derivative having a pyrimidinyl-containing group at the 2-position of the phenyl group and further having an alkoxyalkyl group at the 6-position, and this derivative are not known to have herbicidal action.

By the way, in recent years, in paddy rice cultivation, the control of so-called difficult-to-control weeds, which is a harmful plant occurring in paddy fields and difficult to control effectively with conventional herbicides, has become a problem. These weeds have a heterogeneous outbreak,
Therefore, it must be controlled for a long period of time.
In addition, grass weeds other than rice, which belong to the same family as rice, such as Taenia serrata, are also observed for a long period of time, and their growth is also vigorous, so their control is also an important issue. At present, a herbicide that has high activity against these weeds and can be controlled at the same time has not been developed. Therefore, it has a high herbicidal activity on grass weeds, including difficult-to-control weeds, and can control a wide range of weeds occurring in paddy fields for a long period of time, and it is desired to develop a drug with high safety for mammals. It is rare.

[0004]

Under the above circumstances, the present invention is effective for removing a wide range of weeds including difficult-to-control weeds that occur in paddy fields, and is safe for mammals. The purpose of the present invention is to provide a novel compound useful as

[0005]

Means for Solving the Problems As a result of intensive studies to develop a novel compound having herbicidal activity, the present inventors have found that it has a pyrimidinylhydroxymethyl group at the 2-position of a phenyl group, and 6- An N-trifluoromethanesulfonyl derivative of aniline having an alkoxyalkyl group at the position has a wide range of herbicidal activity at a low dose, and in particular, shows excellent effects on grass weeds, and has high safety for mammals. Based on this finding, they have completed the present invention.

That is, the present invention relates to a general formula having herbicidal activity.

[Chemical 5] The present invention provides a trifluoromethanesulfonylanilide derivative represented by the formula (wherein R is an alkoxyalkyl group) and a salt thereof.

The compound represented by the general formula (I) is
It is a new compound that has not been published in the literature.

[Chemical 6] (Wherein X is a halogen atom and R has the same meaning as described above), and is obtained by reacting the 2-substituted aniline derivative (II) with trifluoromethanesulfonyl halide or trifluoromethanesulfonic anhydride.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The trifluoromethanesulfonylanilide derivative of the present invention has a structure represented by the general formula (I), and R in the general formula (I) is an alkoxyalkyl group, The alkyl group in this alkoxyalkyl group may be linear or branched, and particularly preferably has 1 to 6 carbon atoms. Examples of such an alkoxyalkyl group include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group, a 3-ethoxypropyl group, a 1-methyl-3-methoxybutyl group and the like.

Next, the salt of the compound represented by the general formula (I) is a salt of the sulfonylamide group moiety of this compound and a base. Examples of such salt include sodium salt, potassium salt and the like. You can A typical example of the trifluoromethanesulfonylanilide derivative represented by the general formula (I) is 2-[(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl] -6-methoxymethyl-N-trifluoromethanesulfonylanilide. (Melting point 91 to 92 ° C.) 2-[(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl] -6-methoxyethyl-N-trifluoromethanesulfonylanilide, 2-[(4,6-dimethoxypyrimidine- 2-yl) hydroxymethyl] -6-ethoxymethyl-N-trifluoromethanesulfonylanilide and the like can be mentioned.

The compound represented by the general formula (I) and a salt thereof can be prepared, for example, according to the reaction formula shown in the chemical formula 6 above.
It can be produced by reacting a 2-substituted aniline derivative represented by the general formula (II) with trifluoromethanesulfonyl halide or trifluoromethanesulfonic anhydride, and if desired, converting the product into a salt according to a conventional method.

This reaction is usually carried out in an inert solvent, for example, aliphatic or alicyclic hydrocarbons such as pentane, hexane and cyclohexane, aromatic hydrocarbons such as toluene and xylene, halogenated carbonization such as dichloromethane and chloroform. Hydrogen, alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4
-Ethers such as dioxane, ketones such as acetone and methyl ethyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, and further N, N-dimethylformamide, dimethyl sulfoxide, sulfolane, etc. It is carried out in the presence of a base in an aprotic polar solvent and a mixed solvent thereof. The base used at this time is one conventionally used in this type of reaction, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkaline earth metal hydroxide such as calcium hydroxide, or the like. It is an organic base such as trimethylamine, triethylamine, N, N-dimethylaniline or pyridine, and among them, triethylamine is preferable. The reaction temperature is -70 to 250
C., preferably in the range of −70 to 40 ° C. The reaction time is about 5 minutes to 7 days, though it depends on the kind of the raw material compound and the reaction temperature.

The general formula (II) used as the raw material
For example, the compound represented by
Chemical Research (J. Chem. Research)
), 1977, p. 186 or "Heterocycles", 38.
Vol. 1, No. 1, p. 125, and the corresponding 2- (4,6-dimethoxypyrimidin-2-yl) -2- (2) according to the reaction sequence shown below. -Nitrophenyl) acetonitrile (I
It can be easily produced from II).

[0013]

[Chemical 7] (R in the formula has the same meaning as above)

That is, the compound of the general formula (II) can be prepared, for example, by reacting a 2-nitrophenylacetonitrile derivative with 2-halogeno or alkylsulfonyl-4,6-dimethoxypyrimidine in the presence of a base, or a 2-halogenonitrobenzene derivative. 2- (4,6-dimethoxypyrimidin-2-yl) -2- (2-nitrophenyl) obtained by reacting with 2- (4,6-dimethoxypyrimidin-2-yl) acetonitrile in the presence of a base Acetonitrile (III) is oxidatively decyanolated to form a compound of general formula (IV), then the nitro group of this compound is reduced to an amino group to form a compound of general formula (V), It can be produced by reducing the carbonyl group of a compound to a hydroxymethyl group.

The oxidative decyanolation of the compound of the general formula (III) into the compound of the general formula (IV) is carried out by first oxidizing with an oxidizing agent and then treating with a base. This reaction is usually carried out in an inert solvent, for example, pentane, hexane, cyclohexane and other aliphatic or alicyclic hydrocarbons, toluene, xylene and other aromatic hydrocarbons, dichloromethane, chloroform and other halogenated hydrocarbons, diethyl ether. Ether, tetrahydrofuran,
Ethers such as 1,4-dioxane, ketones such as acetone and methyl ethyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide,
It is carried out in an aprotic polar solvent such as dimethyl sulfoxide and sulfolane, water and a mixed solvent in which these are combined. The oxidizing agent used in the first step is, for example, m-
There are organic peracids such as chloroperbenzoic acid. As the base used in the second step, those conventionally used in this type of reaction, for example, sodium hydroxide, alkali metal hydroxides such as potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, Furthermore, organic bases such as trimethylamine, triethylamine, N, N-dimethylaniline and pyridine are used. Reaction temperature is -70 to 250
C, preferably selected from the range of -20 to 40 ° C. While the reaction time depends on the oxidizing agent used, the type of base and the reaction temperature, it is usually 5 minutes to 7 days.

Next, the reaction of reducing the nitro group of the carbonyl derivative represented by the general formula (IV) thus obtained to an amino group to give the aniline derivative of the general formula (V) is in the presence of a catalyst. Underneath, it can be done with a reducing agent. This reaction is usually carried out in an inert solvent such as alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane, esters such as methyl acetate and ethyl acetate, acetonitrile and propylene. It is carried out in a nitrile such as pionitrile, an aprotic polar solvent such as N, N-dimethylformamide, dimethylsulfoxide and sulfolane, water and a mixed solvent thereof. As the reducing agent, metals such as iron, zinc and tin are used, and as the catalyst, organic acids such as acetic acid are used. The reaction is carried out at a temperature in the range of 20 ° C. to the boiling point of the solvent.
The reaction time depends on the type of reducing agent and catalyst, the reaction temperature, etc., but is usually 5 minutes to 7 days.

Finally, the reduction reaction for converting the carbonyl group of the aniline derivative represented by the general formula (V) thus obtained into a hydroxymethyl group to produce the compound of the general formula (II) is carried out, for example, with hydrogen. It is carried out using an alkali metal hydrogen complex compound such as sodium borohydride as a reducing agent. This reaction is usually carried out in an inert solvent such as aliphatic or alicyclic hydrocarbons such as pentane, hexane and cyclohexane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane and chloroform, and methanol. , Alcohols such as ethanol, diethyl ether, tetrahydrofuran, 1,4-
Ethers such as dioxane, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, and aprotic polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide and sulfolane, water and the like. The mixed solvent of can be used. This reaction is preferably carried out at a temperature in the range of -70 ° C to the boiling point of the solvent, preferably in the range of -20 to 40 ° C, and the reaction time depends on the type of reducing agent and the reaction temperature. , Usually 5 minutes to 7 days.

The herbicide of the present invention containing the compound represented by the general formula (I) as an active ingredient may be the compound itself, but powders, wettable powders, emulsions and fine granules. , Granules and the like, which can be formulated into a conventional dosage form for general herbicides. Excipients and additives used in this case can be arbitrarily selected from those conventionally used in the preparation of ordinary herbicides, depending on the purpose of use. That is, as a carrier used in formulation, for example, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate, a solid carrier such as urea,
Isopropyl alcohol, xylene, cyclohexane,
Examples include liquid carriers such as methylnaphthalene.

As the surfactant or dispersant, for example, metal salts of alkylbenzene sulfonic acid, metal salts of dinaphthylmethane disulfonic acid, alkyl sulfate ester salts, alkylaryl sulfonate formalin condensates, lignin sulfonate and polyoxy are used. Examples thereof include ethylene glycol ether, polyoxyethylene alkylaryl ether, and polyoxyethylene sorbitan monoalkylate. Examples of the auxiliary agent include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like.

When using the herbicide, it is diluted to an appropriate concentration and then sprayed or applied directly. The herbicide of the present invention is used in the form of foliage application, soil application or water surface application. The mixing ratio of the active ingredient in the herbicide of the present invention is appropriately selected according to the purpose of use, but in the case of a powder or granules, it is 0.01 to 10% by weight, preferably 0.05.
It is preferable to select in the range of up to 5% by weight. When it is used as an emulsion or a wettable powder, it is preferable to select it in the range of 1 to 50% by weight, preferably 5 to 30% by weight.

The application rate of the herbicide of the present invention varies depending on the kind of compound used, target weeds, development tendency, environmental conditions, dosage form used, etc., but when it is used as it is as a powder or granule, 0.1 per 10 ares as an active ingredient
It is good to select in the range of g to 5 kg, preferably 1 g to 1 kg. When it is used as a liquid such as an emulsion or a wettable powder, it is 0.1 to 50,000 ppm, preferably 10 to 50,000 ppm.
It is good to select in the range of 10,000 ppm. Further, the herbicide of the present invention may be used in combination with an insecticide, a fungicide, another herbicide, a plant growth regulator, a fertilizer and the like, if necessary.

[0022]

EXAMPLES Next, the present invention will be described in more detail by way of examples, formulation examples and test examples, but the present invention is not limited to these examples.

Reference Example 1; 2- (4,6-dimethoxypyrimidin-2-yl) -2- (3-methoxymethyl-2-
Preparation of Nitrophenyl) acetonitrile 11.2 g (0.28 mol) of 60% sodium hydride is suspended in 100 ml of N, N-dimethylformamide, cooled to 10 ° C or lower in an ice-water bath, and stirred with 2- (4 6
-Dimethoxypyrimidin-2-yl) acetonitrile 2
A solution prepared by dissolving 5 g (0.14 mol) in 100 ml of N, N-dimethylformamide was added dropwise. After the dropping is completed,
The mixture was stirred at room temperature until no hydrogen was generated. 28 g (0.14 g) of 2-chloro-6-methoxymethylnitrobenzene was again cooled to 10 ° C or below in an ice water bath while stirring.
(Mol) was dissolved in 100 ml of N, N-dimethylformamide and added dropwise. After stirring at room temperature for 12 hours, the reaction solution was poured into ice water and acidified with 10 wt% hydrochloric acid,
It was extracted with ethyl acetate. The organic layer was washed with saturated brine and water, dried, concentrated under reduced pressure, and the precipitated crude crystals were washed with a mixed solvent of ethanol and isopropyl ether to give 2- (4,6-dimethoxypyrimidin-2-yl).
31 g (yield 64%) of 2- (3-methoxymethyl-2-nitrophenyl) acetonitrile was obtained as a reddish brown powder (melting point 112-113 ° C).

Reference Example 2; 2- (4,6-dimethoxypyrimidin-2-yl) -2- (3-methoxymethyl-2-
Preparation of Nitrophenyl) acetonitrile 11.2 g (0.28 mol) of 60% sodium hydride is suspended in 100 ml of N, N-dimethylformamide, cooled to 10 ° C or lower in an ice-water bath, and stirred with 3-methoxymethyl- 2-nitrophenylacetonitrile 29g
(0.14 mol) of N, N-dimethylformamide 10
The solution dissolved in 0 ml was added dropwise. After the completion of dropping, the mixture was stirred at room temperature until the generation of hydrogen disappeared. The mixture was cooled again to 10 ° C or lower in an ice-water bath, and with stirring, 30 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine (0.14
Mol) was added, and the mixture was stirred at room temperature for 12 hours, poured into ice water, acidified with 10 wt% hydrochloric acid, and the precipitated crude crystals were separated by filtration and washed with water and an ethanol-isopropyl ether mixed solvent. By washing, 42 g (yield 87%) of 2- (4,6-dimethoxypyrimidin-2-yl) -2- (3-methoxymethyl-2-nitrophenyl) acetonitrile was obtained as a reddish brown powder (melting point 112-113). ° C).

Reference Example 3; (4,6-Dimethoxypyrimidin-2-yl) Preparation of 3-methoxymethyl-2-nitrophenyl ketone 2- (4,6-dimethoxypyrimidin-2 obtained in Reference Example 1 or 2 -Yl) -2- (3-methoxymethyl-2-nitrophenyl) acetonitrile 3.5 g (10 mmol) and 50% by weight m-chloroperbenzoic acid 6.0 g (17
Was dissolved in 30 ml of chloroform and stirred at room temperature for 12 hours. Then, 15 ml of a 10 wt% sodium hydroxide aqueous solution was added, the mixture was stirred at room temperature for 1 hour, 50 ml of chloroform was added, and the organic layer was washed with 5 wt% dilute hydrochloric acid and saturated saline, and then dried. The solvent was distilled off under reduced pressure, and the crystal residue was washed with ethanol-diisopropyl ether to give 2.8 g of (4,6-dimethoxypyrimidin-2-yl) 3-methoxymethyl-2-nitrophenyl ketone (yield 84% ) As a white powder (melting point 1
11-113 ° C).

Reference Example 4; Preparation of 2- (4,6-dimethoxypyrimidine-2-carbonyl) -6-methoxymethylaniline (4,6-dimethoxypyrimidine-2-obtained in Reference Example 3)
A mixture of 3.3 g (10 mmol) of 3-methoxymethyl-2-nitrophenyl ketone, 3 g (54 mmol) of iron powder, 20 ml of water, 150 ml of ethyl acetate and 1 ml of acetic acid at 50 ° C. for 5 hours. It was made to react. The insoluble matter in the reaction solution was filtered off with a filter aid, and the organic layer was washed with saturated brine and dried. The solvent was distilled off under reduced pressure, and the crystal residue was washed with diisopropyl ether to give 2-
(4,6-dimethoxypyrimidine-2-carbonyl)-
2.4 g of 6-methoxymethylaniline (80% yield)
Was obtained as yellow crystals (melting point 100-101 ° C.).

Reference Example 5: Preparation of 2-[(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl] -6-methoxymethylaniline 2- (4,6-dimethoxypyrimidine-obtained in Reference Example 4
2-Carbonyl) -6-methoxymethylaniline 3.1
g (10 mmol) was dissolved in 50 ml of an equal mixed solvent of tetrahydrofuran and water, and 0.6 g (16 mmol) of sodium borohydride was added with stirring at room temperature.
Stirring was continued for another 2 hours at room temperature. 50 ml of ice water was added, extracted with ethyl acetate, and the organic layer was washed with saturated saline,
Dried. The solvent was distilled off under reduced pressure, and the crystalline residue was washed with diisopropyl ether to give 2-[(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl]-
2.8 g of 6-methoxymethylaniline (92% yield)
Was obtained as a white powder (melting point 40-42 ° C.).

Example 2-[(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl] -6-methoxymethylaniline 4.0 g (13.1 mmol) obtained in Reference Example 5 and triethylamine 1.5 g (14.8 mmol) was dissolved in 30 ml of dichloromethane, and 4.0 g (14.2 mmol) of trifluoromethanesulfonic anhydride was added dropwise with stirring at -50 ° C. After continuing stirring at -50 to 0 ° C for 3 hours, the reaction solution was poured into ice water and extracted with dichloromethane. The organic layer was washed with 5% by weight diluted hydrochloric acid and saturated saline,
After drying, the solvent was distilled off under reduced pressure, and the residue was separated and purified by silica gel column chromatography [elution solvent, ethyl acetate: hexane = 1: 3 (volume ratio)] to give 2-
3.8 g (66% yield) of [(4,6-dimethoxypyrimidin-2-yl) hydroxymethyl] -6-methoxymethyltrifluoromethanesulfonylanilide were obtained as colorless granular crystals (melting point 91-92 ° C).

Formulation example 1 0.5 parts by weight of polyoxyethylene octyl phenyl ether, 0.5 parts by weight of β-naphthalenesulfonic acid formalin condensate sodium salt, 10 parts by weight of the compound obtained in the wettable powder example, and diatomaceous earth. 20 parts by weight and 69 parts by weight of clay were mixed and pulverized to prepare a wettable powder.

Formulation Example 2 10 parts by weight of the compound obtained in the wettable powder example, 0.5 part by weight of polyoxyethylene octyl phenyl ether, 0.5 part by weight of β-naphthalenesulfonic acid formalin condensate sodium salt, diatomaceous earth. A wettable powder was prepared by mixing and pulverizing 20 parts by weight, 5 parts by weight of white carbon and 64 parts by weight of clay.

Formulation Example 3 10 parts by weight of the compound obtained in the wettable powder example, 0.5 part by weight of polyoxyethylene octyl phenyl ether, 0.5 part by weight of β-naphthalenesulfonic acid formalin condensate sodium salt, diatomaceous earth. 20 parts by weight, 5 parts by weight of white carbon and 64 parts by weight of calcium carbonate were mixed and pulverized to prepare a wettable powder.

Formulation Example 4 30 parts by weight of the compound obtained in the emulsion example, 60 parts by weight of an equal mixture of xylene and isophorone, and 10 parts by weight of an equal mixture of polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer and alkylaryl sulfonate. An emulsion was prepared by mixing parts by weight.

Formulation Example 5 10 parts by weight of the compound obtained in the granule example, 80 parts by weight of an extender prepared by mixing talc and bentonite in a weight ratio of 1: 3, 5 parts by weight of white carbon, and polyoxyethylene sorbitan alkylate Then, 10 parts by weight of water was added to 5 parts by weight of an equal mixture of polyoxyethylene alkylaryl polymer and alkylaryl sulfonate, and the mixture was well kneaded into a paste, which was extruded through a sieve hole having a diameter of 0.7 mm and dried, and then 0 Granules were prepared by cutting to a length of 0.5 to 1 mm.

Test Example 1 Herbicidal effect test by flooding paddy field Paddy soil was filled in a plastic pot of 100 cm ² and scraped, and then Tainubie (Ec) and Konagi (M)
Various seedlings of o) and firefly (Sc) were sown at a depth of 0.5 cm and submerged at a water depth of 3 cm. The next day, a predetermined amount of active ingredient (g / 10 ares) of the wettable powder prepared according to Formulation Example 1 was diluted with water, and the solution was dropped on the water surface. Then, the plants were grown in a greenhouse, and 28 days after the treatment, the herbicidal effect was evaluated according to the following criteria. The results are shown in Table 1.

For comparison, the formula

[Chemical 8] 2-[(4,6-dimethoxypyrimidine-2
-Yl) hydroxymethyl] -N-trifluoromethanesulfonylanilide (compound number 10-111 of WO96 / 41799) was used to carry out the same test,
The results are also shown in Table 1.

[0036] Criteria for herbicidal effect (growth suppression) and phytotoxicity 5: 90% or more herbicidal effect, phytotoxicity 4: 70% or more and less than 90% herbicidal effect, phytotoxicity 3: 50% or more and less than 70% herbicidal effect, phytotoxicity 2: 30% or more and less than 50% herbicidal effect, phytotoxicity 1: 10% to less than 30% herbicidal effect, phytotoxicity 0: 10% less than herbicidal effect, phytotoxicity

[0037]

[Table 1]

Test Example 2 Herbicidal Effect Test by Paddy Field Water Treatment A plastic pot of 200 cm ² was filled with paddy soil, and after scraping, various kinds of Tainubie (Ec) and firefly (Sc) were placed at a depth of 0.5 cm. Sowing, embedding rhizomes of Urikawa (Sa) and Cyperus cylindrica (Cy), and further paddy rice (Or) at the 2-leaf stage at a transplantation depth of 2 cm
The main transplant was performed and the water was submerged to a depth of 3 cm. On the next day, a predetermined amount of the active ingredient (g / 10 are) of the wettable powder prepared according to Formulation Example 1 was diluted with water and added dropwise to the water surface. Then, it was grown in a greenhouse, and 28 days after the treatment, the herbicidal effect and the degree of phytotoxicity were evaluated according to the same criteria as in Test Example 1. The results are shown in Table 2.

[0039]

[Table 2]

Test Example 3 Herbicidal Effect Test by Paddy Field Flooding Treatment A 200 cm ² plastic pot was filled with paddy soil, and after scraping the seeds, seeds of Tainubie (Ec) were sown.
The seeds were sown at a depth of 5 cm, and at the time when the leaf nosed plants became the 1st leaf stage, the 2nd leaf stage and the 3rd leaf stage, the prescribed active ingredient amount (g / 10 ares) of the wettable powder prepared according to Formulation Example 1 was applied. It was diluted with water and treated dropwise on the water surface. Then, it was grown in a greenhouse and 28 days after the treatment, the herbicidal effect was evaluated according to the same criteria as in Test Example 1. The results are shown in Table 3.

[0041]

[Table 3]

Test Example 4 Teratogenicity test "Guideline for preparing toxicity test results"
According to the method described in (Ministry of Agriculture, Forestry and Fisheries), the compound obtained in Example and the same comparative compound as used in Test Example 1 were weighed, and then suspended in a 0.5% carboxymethylcellulose aqueous solution, and each SD-based pregnancy 6 pregnancies for 10 rats
Gavage was continuously administered from day 15 to day 15. The control group was administered with 0.5% carboxymethyl cellulose aqueous solution only. The dose of each compound was determined as the maximum tolerable dose by conducting a 10-day continuous administration preliminary test using 3 SD non-pregnant rats. On the 20th day of pregnancy, the mother was subjected to a Caesarean section, and an in utero test (number of surviving fetuses, number of resorption embryos, number of dead fetuses, sex ratio, fetal weight) and external fetus examination were performed.
Further, the fetus was fixed with 70% ethanol, the soft tissue was thawed with potassium hydroxide, and the skeleton was stained with alizarin red S, and the skeleton was examined. The results are shown in Table 4. In these inspections, the case where no abnormality was recognized at all was judged to be acceptable, and when any abnormality was recognized, it was judged to be unacceptable.

[0043]

[Table 4]

[0044]

INDUSTRIAL APPLICABILITY The compound of the present invention has a low dose of herbicidal activity and a wide range of application herbicidal activity, and has an excellent control effect against weeds of the family Gramineae in particular, and has no teratogenicity. It is a novel substance useful as a herbicide with high safety for animals.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Masao Nakatani             Shiooka Prefecture Iwata-gun Fukuda Town Shio Shinta No. 408 1             KA Institute Inc. (72) Inventor Masatoshi Tamaru             Shiooka Prefecture Iwata-gun Fukuda Town Shio Shinta No. 408 1             KA Institute Inc. (72) Inventor Takeshi Dangami             1809 Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor, Masamasa Ono             Shizuoka City, Shizuoka Prefecture 2-13, 10 site (72) Inventor Katsutada Yanagisawa             88, 3061 Hansai, Kikugawa-cho, Ogasa-gun, Shizuoka F-term (reference) 4H011 AB02

Claims (4)

[Claims] 1. A general formula: A trifluoromethanesulfonylanilide derivative represented by the formula (wherein R is an alkoxyalkyl group) or a salt thereof. 2. The trifluoromethanesulfonylanilide derivative or the salt thereof according to claim 1, wherein R is a methoxymethyl group. 3. A general formula: Characterized in that a 2-substituted aniline derivative represented by the formula (wherein R is an alkoxyalkyl group) is reacted with trifluoromethanesulfonyl halide or trifluoromethanesulfonic anhydride, and then the product is converted to its salt as desired. And the general formula: A method for producing a trifluoromethanesulfonylanilide derivative represented by the formula (wherein R has the same meaning as described above) or a salt thereof. 4. A compound represented by the formula: A herbicide containing a trifluoromethanesulfonylanilide derivative represented by the formula (wherein R is an alkoxyalkyl group) or a salt thereof as an active ingredient.