JPS6242882B2 - - Google Patents

Description

[Detailed description of the invention]

(1) Industrial Application Field of the Invention The present invention relates to a herbicide containing a novel arylsulfonyl fatty acid amide derivative as an active ingredient. Therefore, it can be effectively used in the fields of organic chemical industry and agriculture and horticulture. Prior Art The following compounds are known as compounds similar to the arylsulfonyl fatty acid amide derivative of the present invention. "Chem.Abstr." Volume 72, Page 79026f and Special Publication No. 1971-7104 X represents Cl, Br, _CH3 , _CF3 , _NO2 , parachlorophenoxy group, and n=1-3.
These compounds are used as raw materials for isothiazoline derivatives that exhibit fungicidal properties, but their herbicidal activity is not described. “Chem.Abstr.” Volume 88, Page 120723b Germicidal activity has been reported, but there is no mention of herbicidal activity. “Chem.Abstr.” Volume 92, Page 67697a It is described as an intermediate for producing raw materials for color photography, but its herbicidal activity is not described. “Chem.Abstr.” Volume 86, Page 139577m It is described as a raw material for obtaining an addition reaction product by reacting with nitrostyrene, but there is no mention of its herbicidal action. “Chem.Abstr.” Volume 82, Page 16438c In the formula, X represents 4-Cl, 4-OCH ₃ , 4-NO ₂ or 4-CH ₃ . It is only described as a raw material for reacting with various diazonium salts, and its herbicidal action is not described. “Chem.Abstr.” Volume 41, pages 3902l-3913c It has been described that it exhibits plant growth regulating effects. “Chem.Abstr.” Volume 68, Page 34536y In the formula, X is H, CH ₃ , Cl, Br, NO ₂ (o-, m
-, p-) or OCH ₃ . NMR data for X and the hydrogen atom on the ring are described, but there is no mention of herbicidal activity. “Chem.Abstr.” Volume 71, Page 101493j There is a description that it exhibits herbicidal and plant growth regulating effects. Problems to be Solved by the Invention Conventional arylsulfonyl fatty acid amide derivatives (such as the compounds described in C and A above) have almost no activity as herbicides. The present invention provides a herbicide containing an arylsulfonyl fatty acid amide derivative as an active ingredient, which is a novel and highly practical herbicide in place of these conventional derivatives. (2) Means for solving the structural problems of the invention The present inventors synthesized a large number of novel arylsulfonyl fatty acid amide derivatives and conducted extensive research. As a result, it was discovered that a series of compounds represented by the general formula () are useful as herbicides. general formula In the formula, R represents a hydrogen atom, a lower alkyl group or a chlorine atom, m represents an integer of 1 or 2,
R ¹ represents a lower alkyl group or lower alkenyl group, R ² represents a lower alkyl group, a lower alkenyl group, the formula

[Formula] (wherein, X represents a lower alkyl group, a halogen atom, a lower alkoxy group, or a trifluoromethyl group, and n is 0, 1, 2
or an integer of 3) group, formula

[Reaction formula]

[Reaction method] To produce the compound of the present invention, first the general formula ()
The amine derivative represented by is dissolved in a suitable reaction solvent such as benzene, toluene, xylene, chlorobenzene, dioxane, tetrahydrofuran, methylene chloride, acetone, methyl alcohol, etc., and the arylsulfonyl fatty acid represented by the general formula () is dissolved in the solution. Alternatively, an equivalent amount of the reactive derivative is added either as such or dissolved in the above-mentioned organic solvent. The reaction is then carried out at room temperature or while cooling or heating as necessary. Reaction time is 1~
5 hours is good. Reactive derivatives of arylsulfonyl fatty acids include acid anhydrides, acid chlorides, acid bromides, and carboxylic acid esters, which can be easily obtained from arylsulfonyl fatty acids by applying known methods. In addition, when reacting the amine derivative of general formula () with the arylsulfonyl fatty acid of general formula () or its reactive derivative, suitable reaction aids such as thionyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, dicyclohexylcarbodiimide, triethylamine,
Pyridine, N-methylmorpholine, N,N-diethylaniline, sodium hydroxide, sodium methylate, sodium carbonate, potassium carbonate, and the like can be used. These reaction aids are preferably selected and used depending on the type of arylsulfonyl fatty acid or reactive derivative thereof. After the reaction, the reaction product is filtered or washed with water to remove the reaction aid, and the organic solvent used is distilled off to obtain the arylsulfonyl fatty acid amide derivative represented by the general formula () with high purity. Moreover, it can be obtained in high yield. These compounds can be further purified by recrystallization with acetone, methyl alcohol, benzene, toluene, chloroform, etc. Reference examples are shown below, but the present invention is not limited to the methods disclosed in these reference examples. Reference example 1 Production of (Compound No. 4) 2-phenylsulfonyl-propionic acid 2.14g
(10 mmol) into a 50 ml round-bottom flask,
5 g (42 mmol) of thionyl chloride was added and the mixture was refluxed for 1 hour with a reflux condenser fitted with a calcium chloride tube. Thereafter, excess thionyl chloride was distilled off under reduced pressure to obtain 2-phenylsulfonyl-propionic acid chloride as a yellow oil. Separately, put 5-chloro-O into a 50ml eggplant-shaped flask.
- 1.78 g (10 mmol) of toluidine hydrochloride and 20 ml of acetone were added, and while stirring in an ice water bath, 2.1 g (20.8 mmol) of triethylamine was added. 2-Phenylsulfonyl-propionic acid chloride dissolved in 3 ml of acetone was then added dropwise over 10 minutes at 5-10 DEG C. and the mixture was heated under reflux for 30 minutes. After distilling off and recovering 15 ml of acetone, the reaction was brought to room temperature and poured into 150 ml of water.
The precipitated crystals were filtered, washed twice with water, and recrystallized from ethyl acetate to obtain 2.9 g of white crystals. melting point
125.5-126.5℃, yield 86.1%. Reference example 2 Production of (Compound No. 10) 2,4-dimethylaniline 1.21 g (10 mmol) and calcium carbonate 1.0 g (10 mmol)
into a four-necked round-bottom flask, and then add 20 ml of acetone. After keeping the internal temperature at 5 to 10°C in an ice water bath and stirring, a solution of 2.47 g (10 mmol) of 2-(2-methylphenylsulfonyl)propionic acid chloride dissolved in 5 ml of acetone was added dropwise over 10 minutes. Heat to reflux for 30 minutes. Then 15 ml of acetone was distilled off to bring it back to room temperature and poured into 150 ml of water. Extracted 3 times with 50 ml of ethyl acetate,
Wash with a 5% aqueous hydrochloric acid solution, a 5% aqueous sodium carbonate solution, and then water, add 5 g of Glauber's salt, shake, dry, filtrate, and distill off the ethyl acetate to obtain N-(2,4-dimethylphenyl). -2-(2-
3.18 g (yield: 96%) of white crystals of methylphenylsulfonyl)propionic acid amide were obtained. melting point
123-124℃. Reference example 3 Preparation of (Compound No. 23) 1.62 g (10 mmol) of 2,5-dichloroaniline and 1.22 g (10 mmol) of dimethylaniline are placed in a four-necked round-bottomed flask, and further 20 ml of benzene is added. Keep the internal temperature at 10℃ in an ice water bath and add 2.47 g (10 mmol) of 2-(3-methylphenylsulfonyl)propionic acid chloride while stirring.
A solution of 5 ml of benzene was added dropwise over 10 minutes, and the mixture was heated under reflux for 1 hour. After that, the temperature is returned to room temperature, 30 ml of benzene and 50 ml of water are added, stirred, and transferred to a separating funnel. Separate the water layer and remove the aqueous layer.
The benzene layer was washed with a 5% aqueous hydrochloric acid solution, a 5% aqueous sodium carbonate solution, and then water, and 2 g of calcium chloride was added.
Add, dry and strain. When the benzene in the liquid is distilled off, N-(2,5-dichlorophenyl)
3.55 g (yield: 95%) of white crystals of -2-(3-methylphenylsulfonyl)propionic acid amide are obtained. Melting point 92.5-95.5℃. Reference example 4 (Compound No. 65) Production 2-methyl-5-fluoroaniline 1.25g (10
mmol) and triethylamine 1.1 g (10.9
millimoles) into a four-necked round-bottomed flask, and also 20 ml of benzene. Keep the internal temperature at 5-10℃ in an ice water bath and add 2.60 g (10 mmol) of 2-(4-methylphenylsulfonyl)butyric acid chloride while stirring.
A solution of 5 ml of benzene was added dropwise over 10 minutes, followed by heating under reflux for 30 minutes. The reaction mixture is then brought to room temperature, 30 ml of water and 30 ml of benzene are added, stirred and transferred to a separating funnel. The aqueous layer separated by standing was removed, washed successively with a 5% aqueous hydrochloric acid solution, a 5% aqueous sodium carbonate solution, and water. 2 g of Glauber's salt was added, mixed, dried, and filtered. When the benzene in the liquid is distilled off, 3.41 g of white crystals of N-(2-methyl-5-fluorophenyl)-2-(4-methylphenylsulfonyl)butyric acid amide (yield 97.7) are obtained.
%) is obtained. Melting point 128-129.5℃. Reference example 5 Preparation of (Compound No. 70) 1.42 g (10 mmol) of 2-methyl-5-chloroaniline and 1.0 g (10 mmol) of calcium carbonate are placed in a four-necked round-bottomed flask, and then 25 ml of acetone is added. Maintain the internal temperature at 5-10℃ in an ice water bath and add 2.75 g (10 mmol) of 2-(4-methylphenylsulfonyl)valeric acid chloride while stirring.
A solution prepared by dissolving the above in 5 ml of acetone was added dropwise over 10 minutes, and the mixture was heated under reflux for 1 hour. 20 ml of acetone are distilled off and the temperature is returned to room temperature. 80ml benzene and water
Add 50ml, stir, and pour into a separating funnel to separate and remove the aqueous layer. Next, the mixture is washed with a 5% aqueous hydrochloric acid solution, a 5% aqueous sodium carbonate solution, and water in this order, and 2 g of Glauber's salt is added, mixed, dried, and filtered. If the benzene in the liquid is distilled off, 3.75 g of white crystals of N-(2-methyl-chlorophenyl)-2-(4-methylphenylsulfonyl)valeric acid amide (yield 99%)
is obtained. Melting point 155-156℃. Reference example 6 Preparation of (Compound No. 81) 1.28 g (10 mmol) of 2-chloroaniline and 1.06 g (10 mmol) of soda carbonate are placed in a four-necked round-bottomed flask, and 20 ml of acetone is added. Keep the internal temperature at 5-10℃ in an ice water bath and stir while stirring.
(4-ethylphenylsulfenyl)propionic acid chloride 2.61 g (10 mmol) in acetone 5 ml
After dropping a solution dissolved in water over 10 minutes, the mixture was refluxed for 1 hour. After distilling off 10ml of acetone, add toluene.
Add 50 ml and 50 ml of water, stir, transfer to a separating funnel, separate the liquids, and remove the aqueous layer. Next, the mixture is washed with a 5% aqueous hydrochloric acid solution, a 5% aqueous sodium carbonate solution, and water in this order, and 2 g of Glauber's salt is added thereto, shaken, dried, and filtered. If liquid toluene is distilled off under reduced pressure, N-
White crystals of (2-chlorophenyl)-2-(4-ethylphenylsulfonyl)propionic acid amide
3.45 g (98% yield) is obtained. Melting point is 89.5~
It showed 90.5℃. Reference example 7 Preparation of (Compound No. 115) 1.62 g (10 mmol) of 2,5-dichloroaniline and 1.22 g (10 mmol) of dimethylaniline are placed in a four-necked round-bottomed flask, and then 25 ml of toluene is added. Keep the internal temperature at 5-10℃ in an ice water bath and add 2.61 g of 2-(2,4-dimethylphenylsulfonyl)propionic acid chloride while stirring.
(10 mmol) dissolved in 5 ml of toluene.
After dropping for 10 minutes, heat at 80°C for 30 minutes. Then bring it back to room temperature and add 20ml of toluene and 50ml of water.
ml and stir, transfer to a separating funnel, separate the liquids, and remove the aqueous layer. Wash with a 5% aqueous hydrochloric acid solution, a 5% aqueous sodium carbonate solution, and water in this order, add 2 g of Glauber's Salt, shake, dry, and filter. If the toluene in the liquid is distilled off under reduced pressure, white crystals of N-(2,5-dichlorophenyl)-2-(2,4-dimethylphenylsulfonyl)propionic acid amide 3.7
g (yield 96%) is obtained. Melting point 137-139℃. Reference example 8 Preparation of (Compound No. 134) 1.61 g (10 mmol) of 2-trifluoromethylaniline and 1.1 g (10.9 mmol) of triethylamine are placed in a four-necked round-bottom flask, and 25 ml of benzene is added. Keep the internal temperature at 5-10℃ in an ice water bath and add 2-(3-chloro-4-methylphenylsulfonyl)propionic acid chloride while stirring.
A solution of 2.81 g (10 mmol) dissolved in 5 ml of benzene was added dropwise over 10 minutes, followed by heating under reflux for 30 minutes. After that, return to room temperature, add 30ml of benzene and water.
After adding 50 ml and stirring, transfer to a separating funnel and remove the aqueous layer. 5% aqueous hydrochloric acid solution for the benzene layer,
Wash with a 5% aqueous sodium carbonate solution and then with water, add 2 g of Glauber's salt, mix, dry, and filter.
When the benzene in the liquid is distilled off, N-(2-trifluoromethylphenyl)-2-(3-chloro-4-
Methylphenylsulfonyl) propionic acid amide
3.9 g (yield 96%) is obtained. Melting point 76.5-79.5
℃. Reference example 9 Production of (Compound No. 140) 2-Methyl-5-fluoroaniline 1.25g (10
1.0 g (10 mmol) of calcium carbonate and 1.0 g (10 mmol) of calcium carbonate were placed in a four-necked round-bottomed flask and added with acetone.
Add 20ml. Keep the internal temperature at 5-10℃ in an ice water bath.
While stirring, a solution of 2.67 g (10 mmol) of 2-(4-chlorophenylsulfonyl)propionic acid chloride dissolved in 5 ml of acetone was added dropwise over 10 minutes, followed by heating under reflux for 1 hour. acetone 15
ml and return to room temperature. Add 50 ml of water and 50 ml of ethyl acetate, stir and transfer to a separating funnel, remove the aqueous layer, and add 5% aqueous hydrochloric acid solution and 5% ethyl acetate layer.
The mixture is washed with an aqueous sodium carbonate solution and then with water, and 3 g of Glauber's salt is added, mixed, dried, and filtered.
When the ethyl acetate in the liquid is distilled off, N-(2-methyl-
White crystals of 5-fluorophenyl)-2-(4-chlorophenylsulfonyl)propionic acid amide
3.45 g (97% yield) is obtained. Melting point 118.5~
120.5℃. Reference example 10 (Compound No. 146) 1.41 g (10 mmol) of 2-methyl-5-chloroaniline and 1.5 g (10.9 mmol) of calcium carbonate were placed in a four-necked round-bottomed flask, and benzene
Add 30ml. While keeping the internal temperature at 5 to 10°C in an ice water bath, a solution of 3.01 g (10 mmol) of 2-(2,5-dichlorophenylsulfonyl)propionic acid chloride dissolved in 5 ml of benzene was added dropwise over 10 minutes while stirring. Then, heat under reflux for 1 hour. Return this to room temperature, add 20ml of benzene and 50ml of water,
After stirring, transfer to a separating funnel and separate the liquids to remove the aqueous layer. Add benzene layer to 5% hydrochloric acid aqueous solution, 5%
After sequentially washing with an aqueous sodium carbonate solution and water, 3 g of Glauber's salt was added, mixed, dried, and filtered. When the benzene in the liquid was distilled off, 3.9 g (yield 96%) of white crystals of N-(2-methyl-5-chlorophenyl)-2-(2,5-dichlorophenylsulfonyl)propionic acid amide was obtained. Melting point 120
~122℃. Table 1 shows the compounds produced by the method of the present invention.

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[Table] When actually using the compound of the present invention as a herbicide, the compound of the present invention may be sprayed as it is on the soil or foliage of crop cultivation areas, but the herbicidal effect of the compound of the present invention is In order to achieve its full potential, it is mixed with suitable carriers and auxiliary agents such as surfactants, binders, stabilizers, etc., and prepared as wettable powders, emulsions, aqueous solutions, oil suspensions, etc. using conventional methods. It is preferable to use it in the form of a powder, fine granule, coarse powder, or the like. In the above, the carrier is not limited to any particular carrier, as long as it is commonly used for agricultural and horticultural chemicals, either solid or liquid can be used. For example, solid carriers include mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite,
Gypsum, calcium carbonate, apatite, white carbon, slaked lime, silica sand, ammonium sulfate, urea, etc.), vegetable powders (soybean flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyester, etc.) (vinyl chloride, ketone resin, dammargum, etc.), alumina, silicates, sugar polymers, highly dispersed silicic acid, waxes, etc. Liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chloride, etc.). benzene, cumene,
methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane,
chloroethylene, trichlorofluoromethane, dichlorodifluoromethane, etc.), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone,
methyl isobutyl ketone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.),
Nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether,
ethylene glycol monoethyl ether, etc.),
Aliphatic or alicyclic hydrocarbons (n-hexane,
cyclohexane, etc.), industrial gasoline (petroleum ether, solvent naphtha, etc.), and petroleum distillates (paraffins, kerosene, light oil, etc.). In addition, surfactants (or emulsifiers) are used for the purposes of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading, etc. in the formulation of emulsifiers, wettable powders, flowable agents, and the like. Such surfactants include nonionic types (polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester,
sorbitan alkyl ester, etc.), anionic type (alkylbenzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate, etc.), cationic type [alkylamines (laurylamine, stearyltrimethylammonium chloride, etc.) (alkyldimethylbenzyl ammonium chloride, etc.), polyoxyethylene alkyl amines], amphoteric type (carboxylic acid (betaine type), sulfuric acid ester salt, etc.), but of course the present invention is not limited to these examples. In addition to these, various adjuvants such as polyvinyl alcohol, carboxymethylcellulose, gum arabic, polyvinyl acetate, gelatin, casein, sodium alginate, gum tragacanth, and the like can be used. Furthermore, the compound of the present invention can be used in combination with other herbicides in order to improve herbicidal efficacy or to expect a synergistic herbicidal effect. Examples of this include phenoxy herbicides (2, 4
-dichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxybutyric acid and their esters,
Thioesters and salts, 2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxypropionate n-butyl]), diphenyl ether herbicides (2,4-dichlorophenyl-4') ―
Nitrophenyl ether, 2,4,6-trichlorophenyl-4'-nitrophenyl ether, 2-
Chloro-4-trifluoromethyl-3'-ethoxy-4'-nitrophenyl ether, 2,4-dichlorophenyl-4'-nitro-3'-methoxyphenyl ether, 2,4-dichlorophenyl- 3′-methoxycarbonyl-4′-nitrophenyl ether, etc.), triazine herbicides (2-chloro-4,6
-bisethylamino-1,3,5-triazine,
2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-methylthio-4,6-bisethylamino-1,3,5-
triazine, 2-methylthio-4,6-bisisopropylamino-1,3,5-triazine, etc.), urea herbicides {3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3- (3,4
-dichlorophenyl)-1-methoxy-1-methylurea, 1-(2,2-dimethylbenzyl)-3
-P-tolylurea}, carbamate herbicides {isopropyl-N-(3-chlorophenyl) carbamate, methyl-N-(3,4-dichlorophenyl)-carbamate}, thiol carbamate herbicides {S-(4 -chlorobenzyl) N,N-diethylol carbamate, S-ethyl-N,N
-hexamethylenethiol carbamate), acid anilide herbicides (3,4-dichloropropionanilide, N-methoxymethyl-2,6-diethyl-α-chloroacetanilide, 2-chloro-2',
6′-diethyl-N-butoxymethyl)-acetanilide, 2-chloro-2,6-diethyl-N-
(n-propoxyethyl)-acetanilide, N
-Chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester, uracil herbicide (5-bromo-3-secondary butyl-6-methyluracil, 3-cyclohexyl-5,6-trimethylene) uracil, etc.), pyridinium chlorine herbicides (1,1'-dimethyl-4,4'-bispyridinium chloride, etc.), phosphorus herbicides {N-(phosphonomethyl)glycine, O-ethyl-O-(2-nitro -5-methylphenyl-N-secondary butyl phosphoramidothioate, S-(2-methyl-1-
piperidylcarbonylmethyl)-O,O-di-n
-Propyldithiophosphate, S-(2-methyl-1-piperidylcarbonylmethyl)-O,O
-diphenyldithiophosphate, ammonium-(3-amino-carboxypropyl)-methylphosphinate, 2-amino-4-methylphosphinobutylalanylalanine, toluidine herbicide (α,α,α-trifluoro -2,6-dinitro-N,N-dipropyl-P-toluidine, etc.), others {5-tert-butyl-3-(2,4
-Dichloro-5-isopropoxyphenyl)-
1,3,4-oxadiazolin-2-one, 3-
Isopropyl-1H-2,1,3-benzothiadiazine-(4)-3H-one-2,2-dioxide,
α-(β-naphthoxy)-propionanilide,
4-(2,4-dichlorobenzoyl)-1,3-
Examples include, but are not limited to, dimethylpyrazol-5-yl-P-toluenesulfonate, 2-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonylaminosulfonylmethyl]benzoic acid methyl ester}, etc. It's not a thing. The compound of the present invention can also be used in combination with an insecticide, nematocide, fungicide, water-applied insecticide, fungicide, soil-applied fungicide, plant growth regulator, fertilizer, or the like, if necessary. The application amount of the compound of the present invention of general formula () varies depending on the type of specific compound to be used, the type of weeds to be weeded, etc., but is generally in the range of 0.02 to 2 kg per 10 ares. It's good to have one. Examples of the herbicide of the present invention will be shown below, but the proportions of active ingredients, carriers and adjuvants and their types are not limited to the following examples. In addition, all parts in the formulation examples indicate parts by weight. Example 1 Wettable powder 30 parts of Compound No. 28, 2 parts of ligninsulfonic acid calcium salt, 3 parts of dodecylbenzenesulfonic acid sodium salt, and 65 parts of diatomaceous powder are thoroughly ground and mixed to obtain a wettable powder. Example 2 Granules 7 parts of compound No. 71, 2 parts of white carbon,
Five parts of the calcium ligninsulfonate salt and 88 parts of the clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, granulated, and dried to obtain granules. Example 3 Granules 60 parts of clay, 35 parts of bentonite and 5 parts of lignin sulfonic acid calcium salt are ground and mixed, water is added, kneaded and granulated and dried to produce active ingredient-free granules. Granules are obtained by impregnating 95 parts of the granules with 5 parts of Compound No. 106. Example 4 Granule 96 of bentonite sieved to 300-850 microns
part is impregnated with 4 parts of Compound No. 83 to obtain granules. Example 5 Powder 3 parts of compound No. 115, 36 parts of clay, talc
Add 60 parts and 1 part of isopropyl phosphate, and grind and mix with an atomizer at 12,000 rpm to obtain a powder. Example 6 Emulsion 30 parts of Compound No. 146, 60 parts of xylene and Solpol SM100 (trade name of a surfactant from Toho Chemical Industry Co., Ltd. containing a mixture of a nonionic surfactant and an anionic surfactant) ) to obtain an emulsion. (3) Effects of the invention Next, the herbicidal effects of the compounds of the present invention will be shown in test examples. Test Example 1 Flooded soil treatment herbicidal test A 1/15,500 are porcelain pot was filled with paddy soil, and the seeds of wild grass, bulrush, cypress, Japanese cypress, and Kikashigusa were sown uniformly on the surface layer, and then at a depth of 2 cm. After flooding, two paddy rice seedlings (variety: Nipponbare) at the two-leaf stage were transplanted. One day later, a predetermined amount of a diluted solution of the hydrating agent obtained according to Example 11 was uniformly dropped onto the water surface for treatment. Afterwards, the pots were kept in a greenhouse and watered at appropriate times. Twenty days after the chemical solution treatment, the herbicidal effect and the degree of chemical damage to paddy rice were investigated using the following criteria. This test example was conducted using a 3-pot system of 1 dose, and the average value was determined. The results are shown in Table 2. Weeding effect: 5: Weed killing rate 95% or more - complete death 4: Weed killing rate 80% or more - less than 95% 3: Weed killing rate 50% or more - less than 80% 2: Weed killing rate 30% or more - less than 50% 1: Weed killing rate 10% or more to less than 30% 0: Weed killing rate less than 10% Chemical damage -: Harmless ±: Slight damage (leaf tip blight) +: Moderate damage (leaf blight) 〓: Severe damage (growth suppression) 〓: Severe damage (death) )

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[Table] Comparative drugs have the following chemical structures, and these were formulated and tested in the same manner as the compounds of the present invention.

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Claims (1)

[Claims] 1. General formula {In the formula, R represents a hydrogen atom, a lower alkyl group, or a chlorine atom, m represents an integer of 1 or 2,
R ¹ represents a lower alkyl group or a lower alkenyl group, R ² represents a lower alkyl group, a lower alkenyl group, the formula [formula] (wherein, X represents a lower alkyl group, a halogen atom, a lower alkoxy group, or a trifluoromethyl group). and n is 0, 1, 2
or an integer of 3), a group of the formula [formula] (wherein P represents an integer of 0, 1, or 2), an α-methylbenzyl group, an α,α-dimethylbenzyl group, or a tetralinyl group. and R ³ represents a hydrogen atom or a lower alkyl group, or R ² and R ³ have 4 to 6 carbon atoms and can form a saturated ring}. A herbicide characterized by being an active ingredient.