JPH0122263B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the formula [] N-t-butyl-3-methyl-4- represented by
This invention relates to trifluoromethanesulfonamide-benzenesulfonamide, its production method, and herbicides containing them as active ingredients. In the present invention, N-
Also included are salts of t-butyl-3-methyl-4-trifluoromethanesulfonamide-benzenesulfonamide, such as sodium, potassium, calcium, ammonium,
Propylammonium, diethylammonium,
Examples include triethylammonium, hydroxyethylammonium, and dihydroxyethylammonium salts. Special Publication No. 54-11297 and U.S. Patent No.
It is known from No. 3639474 that trifluoromethanesulfonanilide derivatives exhibit herbicidal activity. However, trifluoromethanesulfonanilide derivatives substituted with N-substituted sulfamoyl groups are not known. In general, it is well known that the physiological activity of a compound varies greatly depending on the type of substituent and the substitution mode, such as the position of substitution, even within related compounds. In particular, the selective herbicidal properties between plant species, regardless of whether they are weeds or crops, vary greatly depending on the substitution mode and are difficult to predict. While investigating the herbicidal activity of trifluoromethanesulfonanilide derivatives, the present inventors discovered that N-
It has been found that t-butyl-3-methyl-4-trifluoromethanesulfonamide-benzenesulfonamide has strong herbicidal activity and exhibits high crop selectivity. The compound of the present invention represented by the formula [] has a herbicidal action, and has a strong effect on upland weeds such as barnyard grass, crabgrass, blueberry, whiteweed, polygonum, chickweed, and cyperus. The compound of the present invention is useful for Cyperus rotundus, which has become a worldwide problem in recent years, and the highly harmful grass Cyperus rotundus.
It exhibits strong activity against the rhizome of esculentus seiban, and is also characterized by its strong effects on difficult-to-control large-seeded weeds such as morning glory, Japanese sorghum, Japanese sorghum, and other large-seeded weeds. When the compound of the present invention is applied to upland fields, it has a strong effect both in soil treatment before the emergence of weeds and in foliage treatment performed in the early stages of growth, and is safe and harmless to major crops such as soybean, cotton, and sugar beet. It has the property of being usable. The compounds of the present invention are also effective as herbicides for various cereals, vegetables, orchards, lawns, pastures, tea gardens, mulberry gardens, rubber gardens, forest lands, non-agricultural lands, and the like. These excellent properties as herbicides, as shown in the examples below, far exceed those of the compounds described in the citations. The compounds of the present invention can generally be produced by the following method. That is, by heating 2-methyl-trifluoromethanesulfonanilide and chlorosulfonic acid in a suitable solvent such as methylene chloride or chloroform, 3-methyl-4-trifluoromethane represented by the following formula [] is produced. Sulfonamide-benzenesulfonyl chloride is obtained. Compound [] obtained by the above method and t
-butylamine in a suitable solvent such as tetrahydrofuran, dimethoxyethane, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dimethylformamide, dimethyl sulfoxide, water, etc., if necessary, with a suitable basicity. Catalysts, such as triethylamine, tributylamine, pyridine, N-methylmorpholine, N,N-diethylaniline, N,N-dimethylaniline, potassium carbonate, sodium carbonate, caustic potash, caustic soda, etc.
Preferably in the presence of triethylamine, preferably by reacting at 0°C to 50°C, the desired N-t-butyl-3- represented by the formula []
Methyl-4-trifluoromethanesulfonamide-benzenesulfonamide is obtained. This substance is acidic in nature, and depending on the reaction conditions and recovery procedure, it can be in free form (compound []) or in salt form (i.e., a compound [] in which the hydrogen bonded to the nitrogen of the sulfonamide is replaced by a cation).
obtained as. Conversion of the free form of the compound [ ] into the salt form and vice versa can be carried out by conventional methods. Specific production examples of the compounds of the present invention will be described, but the present invention is of course not limited to these. Example 1 Process for producing Nt-butyl-3-methyl-4-trifluoromethanesulfonamide-benzenesulfonamide 3-Methyl-4-trifluoromethanesulfonamide in 40 ml tetrahydrofuran containing 0.65 g of t-butylamine. 1.5 g of benzenesulfonyl chloride was added and left overnight. Concentrate the reaction solution,
The obtained oil was extracted with chloroform, washed with 5% aqueous hydrochloric acid, further washed with water, and dried over magnesium sulfate. Chloroform was distilled off from the extract, and benzene was added to the residue for crystallization. The crystals were filtered, recrystallized with toluene, and Nt-butyl-3-
0.57 g of methyl-4-trifluoromethanesulfonamide-benzenesulfonamide was obtained. melting point
139.5-140.5°C When actually using the compound of the present invention, the active substance itself may be sprayed, or granules, fine granules, powders, etc.
Coarse powders, large powders, emulsions, aqueous solutions, oil suspensions, etc. may be prepared and used according to conventional methods. in this case,
The content of the compound of the present invention in each formulation is 0.1
-99%, preferably 3-80%. Solid carriers used in preparing these formulations include, for example, mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, apatite, etc.). , vegetable powder (soybean flour,
Wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl chloride, dammar gum, ketone resin, etc.), alumina, waxes, etc. Examples of liquid carriers include alcohols (methyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, methylnaphthalene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, monochlorobenzene, etc.), and ether. (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, etc.), acid amides (dimethylformamide, etc.), nitriles (acetonitrile, etc.) , ether alcohols (ethylene glycol ethyl ether, etc.),
Water etc. can be given. Surfactants that can be used for purposes such as emulsification, dispersion, and spreading include nonionic, anionic, cationic, and zwitterionic surfactants, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl, etc. Ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, oxyethylene oxypropylene polymer,
These include polyoxyethylene alkyl phosphates, fatty acid salts, alkyl sulfate salts, alkyl sulfonates, alkylaryl sulfonates, alkyl phosphate ester salts, polyoxyethylene alkyl sulfate esters, quaternary ammonium salts, and the like. For these purposes, gelatin, casein, sodium alginate, starch, agar,
Polyvinyl alcohol or the like can be used as an adjuvant. Examples of blending the compounds of the present invention are shown below. Formulation Example 1 80 parts by weight of compound [], 3 parts by weight of alkyl sulfate, 2 parts by weight of lignin sulfonate and 15 parts by weight of white carbon are thoroughly ground and mixed to obtain an 80% hydrating powder of compound []. Formulation Example 2 80 parts by weight of compound [], 6 parts by weight of 50% powder of polyoxyethylene alkylaryl ether, 2 parts by weight of lignin sulfonate, and 12 parts by weight of white carbon were thoroughly ground and mixed to make 80% water of compound []. Obtain Japanese medicine. Formulation example 3 Compound [] 10 parts by weight, emulsifier Solpol 2680
(Toho Chemical registered trademark name), 60 parts by weight of cyclohexanone, and 20 parts by weight of xylene are thoroughly mixed to obtain a 10% emulsion of compound []. Formulation Example 4 5 parts by weight of compound [], 1 part by weight of white carbon, 35 parts by weight of bentonite and 59 parts by weight of clay were thoroughly pulverized and mixed, water was added and the mixture was thoroughly kneaded, then granulated and dried to form 5 parts by weight of compound []. Obtain % granules. Formulation example 5 Compound [] 3 parts by weight, isopropyl phosphate
0.3 parts by weight, 66.7 parts by weight of clay, and 30 parts by weight of talc are thoroughly ground and mixed to obtain a 3% powder of the compound []. When the compounds of the present invention are used either pre- or post-emergence, the application rate can vary over a fairly wide range, but is usually from 1 g to 100 g per are, preferably from 3 g to 60 g. Furthermore, the compound of the present invention can be used in combination with other herbicides in order to improve its effectiveness as a herbicide, and in some cases a synergistic effect can be expected.
Examples include phenoxy herbicides such as 2,4-dichlorophenoxyacetic acid; 2-methyl-4-chlorophenoxybutyric acid; 2-methyl-4-chlorophenoxyacetic acid (including esters and salts); -Dichlorophenyl 4'-nitrophenyl ether; 2,4,6-trichlorophenyl
4′-nitrophenyl ether; 2-chloro-4
-Trifluoromethylphenyl 3'-ethoxy-
Diphenyl ethers such as 4'-nitrophenyl ether; 2,4-dichlorophenyl 4'-nitro-3'-methoxyphenyl ether; 2,4-dichlorophenyl 3'-methoxycarbonyl-4'-nitrophenyl ether Herbicide, 2-chlor-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;
Triazine herbicides such as 4-amino-6-tertiarybutyl-3-methylthio-1,2,4-triazin-5-one, 3-(3,4-dichlorophenyl)-1,1-dimethylurea; 3 -(3,
4-dichlorophenyl)-1-methoxy-1-methylurea, 1-(2,2-dimethylbenzyl)
- Urea herbicides such as 3-p-tolylurea, isopropyl N-(3-chlorophenyl) carbamate; carbamate herbicides such as methyl N-(3,4-dichlorophenyl) carbamate, S
-(4-Chlorbenzyl) N,N-diethylthiol carbamate; S-ethyl N,N-hexamethylenethiol carbamate; S-ethyl
N,N-diisobutylthiol carbamate; S
-Ethyl N,N-dinormalpropylthiol carbamate; S-normalpropyl N,N-
Thiol carbamate herbicides such as di-n-propylthiol carbamate, 3,4-dichloropropionanilide; N-methoxymethyl-2,
6-diethyl-α-chloroacetanilide; 2-
Chlor-2',6'-diethyl-N-(butoxymethyl)-acetanilide;2-chloro-2',6'-diethyl-N-(n-propoxyethyl)-acetanilide; N-chloroacetyl-N-( 2,6-
diethyl phenyl)-glycine ethyl ester;
Acid anilide herbicides such as 2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-(2-methoxy-1-methyl)acetamide, 5-bromo-3-secondary-butyl-6- Methyluracil: Uracil herbicides such as 3-cyclohexyl-5,6-trimethyleneuracil, pyridinium salt herbicides such as 1,1'-dimethyl-4,4-bispyridinium chloride, N,N-bis(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)
Phosphorous herbicides such as O,O-diphenyldiophosphate, α,α,α-tolufluoro-2,6-dinitro-N,N-dipropyl-p-toluidine;
Toluidine herbicides such as 2,6-dinitro-N-secbutyl-3,4-xylidine, 5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3, 4-Oxadiazolin-2-one; 3-isoprobyl-1H-2,
1,3-benzothiadiazine-4-3H-one-
2,2-dioxide, α-(β-naphthoxy)-
Propionanilide, 4-(2,4 dichlorobenzoyl)-1,3-dimethylpyrazole-5-
p-toluenesulfonate, 4' phenylsulfonyl-1,1,1-trifluorosulfono-
Examples include, but are not limited to, o-toluidide, 4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)pyridazon-3-(2H)-one, and the like. Furthermore, the compound of the present invention can be used in combination with insecticides, nematicides, fungicides, plant growth regulators, fertilizers, etc., if necessary. Next, the present invention will be explained in more detail by giving examples related to herbicidal efficacy. Example 2 Soil treatment test after sowing in the field Plastic pigtails (vertical 20 cm, horizontal 30 cm) were injected with crabgrass, blueberry, Seiban sorghum, hackberry, red deer, Japanese fir, weed seeds of morning glory, Cyperus esculentus tubers, Seiban sorghum rhizome, soybean, and cotton. After sowing or planting the seeds of the following crops and laying the soil, a predetermined amount of the raw material was made into an emulsion, diluted with water, and the soil was treated with a hand sprayer. After that, it was grown in a greenhouse and 20 years after treatment.
The herbicidal efficacy and crop damage were observed on the following day, and the results are shown in Table 1. The herbicidal efficacy is evaluated from 0 to 0 as shown below.
Represented by the number 5. However, phytotoxicity of crops is also shown using the same criteria as herbicidal efficacy. 0...Weed suppression rate 0-9% 1... 〃 10-29% 2... 〃 30-49% 3... 〃 50-69% 4... 〃 70-89% 5... 〃 90-100%

[Table] Example 3 Post-germination foliage treatment test in the field Seiban sorghum, hackberry, oat,
Seeds of morning glory, morning glory, sunflower, dogweed, chickweed, japonica, soybean, and sugar beet were sown, and tubers of red mulberry were planted. After covering with soil, they were grown in a greenhouse at 25°C for 20 hours. Two of these vats were lined up in a frame measuring 50 cm in length, 100 cm in width, and 40 cm in height, and the treatment amount of each chemical was applied to the entire area within the frame using a hand sprayer from above the plants. After being grown in a greenhouse for an additional three weeks after spraying the chemicals, each plant was examined for chemical damage or herbicidal efficacy. The results are shown in Table 2. As the treatment agent, an emulsion prepared according to the formulation in Formulation Example 3 was used, a predetermined amount was dispersed in water, and the test was conducted at a rate of 5 sprays per are. The size of the plants at the time of chemical treatment varied depending on the species, but they were approximately at the 2-6 true leaf stage and 2-20 cm tall.

[Table] ***Bentazon

Claims (1)

[Claims] 1 formula N-t-butyl-3-methyl-4- represented by
Trifluoromethanesulfonamide-benzenesulfonamide. 2 formulas Nt-butyl-3-methyl-4-trifluoromethanesulfonamide-benzenesulfonamide, which is characterized by reacting 3-methyl-4-trifluoromethanesulfonamide-benzenesulfonyl chloride represented by t-butylamine. manufacturing method. 3 formulas N-t-butyl-3-methyl-4- represented by
A herbicide characterized by containing trifluoromethanesulfonamide-benzenesulfonamide as an active ingredient.