JPS60156601A - Herbicide for paddy field - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a herbicide for paddy fields. More specifically, the present invention relates to a weed killer containing a benzenesulfonyloxyanilide derivative as an active ingredient.

Many herbicides for paddy fields have been proposed and put into practical use. However, if the weeding effect is strong, seedlings may be damaged,
On the other hand, herbicides that do not cause chemical damage have had problems such as not being able to achieve sufficient weeding effects. Therefore, in order to overcome this problem, methods have been used such as applying several types of herbicides at different times and transplanting rice.

As a result, chemicals had to be sprayed many times, and expansion of the area of rice cultivation by flooding and direct seeding was prevented.As a result of intensive research into sulfonyloxyacetamide derivatives, the inventors of the present invention have unexpectedly discovered two 07 T-nyl group-containing -t-ruphenylsulfonylaniFJ are all (
The present inventors have discovered that this product exhibits excellent herbicidal activity against paddy field weeds without causing any chemical damage to paddy rice, and has completed the present invention.

That is, the present invention is a herbicide for paddy fields characterized by containing all of the phenylsulfonyl-oxyacetanilide derivatives represented by the following general formula (1).

[In the formula, W represents a methyl group or an ethyl group, t represents a pulkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, m is 0.1 or 2, and n is 0. Or represents 1. ] The genylsulfonyloxyacetanilide derivative represented by the general formula [I] is included in the compounds represented by the general formula of U.S. Patent No. 3,399,988, but is not specifically disclosed in that publication. The compound that is
Only phenylsulfonyloxyacetoalkylamides, phenylsulfonyloxyacetocycloalkyleneamides or alkylsulfonyloxyacetanilides, and no phenylsulfonyloxacetanilides having two phenyl groups. Not disclosed.

Furthermore, regarding herbicidal activity, the sulfonyloxyamides are only described against upland weeds;
There is no mention of application to paddy fields. Furthermore, there is no suggestion of herbicidal activity for phenylsulfonylox-7acetanilides. When the present inventors applied methanesulfonyloxy-N-methylacetanilide, which is a specific compound described in the publication, to rice fields, they found that it caused serious damage not only to directly sown rice but also to more advanced transplanted rice. It was found that it caused drug damage.

The herbicide of the present invention is highly effective against various weeds in paddy fields, and is also highly safe against paddy rice at all growth stages (from the time of germination to the growing season), that is, it is clearly highly selective between paddy rice and weeds. It has biological activity. Therefore, it is extremely safe for flooded direct-seeded paddy rice from the time of germination to about 10 days after germination, and young seedlings immediately after transplantation, so it can be used for any stage of direct-seeded paddy rice and transplanted paddy rice, especially for direct-seeded paddy rice. The weeds that can be controlled by the herbicide of the present invention are mainly grass weeds such as field weeds that propagate in rice paddies, cypress weeds,
These include weeds of the Cyperaceae family, such as pine needles and bulrushes, or broad-leaved weeds such as cyperus japonica, japonica, azalea, apno, meadow, and water chickweed. □・ Compounds of formula (1) contained in the herbicide of the present invention include the following: ・ Compound and: Compound name □ □・ (1) 2- (benzene, sulfonyloxy)-
N-methyl-N・-phenylacedo, mido... (2) 2-□(benzenesulfonyloxy・,)-N
-(4-methoxyphenyl)-N-methylacetamide (a) 2-(benzenesulfonyloxy)-N-(3-
chlorophenyl)-N- □, methylacetamide □-(4) 2-(benzenesulfonyloxy)-N-
Ethyl-N=(2-methyl-rufe-nyl)acetamide (512-(benzenes, sulfonyloxy)' -N-
ethyl-N-(2,4-dichlorophenyl)acetamide (6) 2-(benzenesulfonyloxy)-N=ethyl-N-(2,5-dimethoxyphenyl)acetamide (7)' 2-(4-methyl benzenesulfonyloxy)-N-methyl-N-phenylacetamide (8) 2- (4-methylbenzenesulfonyloxy)
-N-ethyl-N-phenylacetamide (9) 2-(4-methylbenzenesulfonyloxy')-N-(2-chlorophenyl)-N-methyruacetamide (2) 2-(4-methylbenzenesulfonyloxy') )
-N-(3-chlorophenyl)-N-methylacetamide OJ 2-(4-methylbenzenesulfonyloxy)-
N-(4-chlorophenyl)-N-methylacetamide (2) 2-(4-methylbenzenesulfonyloxy)
-N-(2-chloroform α-wound iN-ethylacetamide (2) 2-(4-methylbenzenesulfonyloxy)
, -N-methyl-N-(2-methylphenyl)acetamide a◆ 2-(4-methylbenzenesulfonyloxy)-
N-(4-methylphenyl)acetamide 0→ 2- (4-methylbenzenesulfonyloxy)
~N-(2-methoxyphenyl)-N-methylacetamide 01 2-(4-, l-methylbenzenesulfonyloximine N-ethyl-N-(2-methoxyphenyl)acetamide) (li 2-(
4-methylbenzenesulfonyloxy)-N-(3-methoxyphenyl)-N-methylacetamide) 2- (2-, I-methylbenzenesulfonyloxy)
)-N-(2-methoxyphenyl)-N-methylacetamide 2-(4-methylbenzenesulfonyloxy)-N-ethyl-N-(2-methoxyphenyl)acetamide 2-(4-methylbenzenesulfonyloxy) )-N-(2,5-dimethoxyphenyl)-N
-Methylacetamide 2- (2-methylbenzenesulfonyloxy)-N-(2,5-dimethoxyphenyl)-N
-Methylacetamide 2-(4-methylbenzenesulfonyloxy)-N-ethyl-N-(2-ethoxy-5-methylphenyl)acetamide 2-<4-l methylbenzenesulfonyloxy) -N-(2-ethoxy- 5-methylphenyl)-N-methylacetothymide 2-(4-, l-methylbenzenesulfonyloxy)-N-(2-methoxy-5-)f-ruphenyl)-N-methylacetamide-(c) 2-( 4-methylbenzenesulfonyloxy)
-N-(3,4-dichlorophenyl)-N-ethylacetamide (c) 2-(2-,l-methylbenzenesulfonyloxy)-N-(2,5-dichlorophenyl)-N-methylacetamide @ 2-(4 -, l-methylbenzenesulfonyloxy)-
N-(2,4-dimethylphenyl)-N-ethylacetamide ■ 2-(4-)Tylbenzenesulfonyloxy)-N
-(2-chloro-5-methylphenyl)-N-methylacetamide 2-(4-/Tylbenzenesulfonyloximine N-
Ethyl-N-(5-chloro-2-methoxyphenyl)acetamide The compound of the present invention can be produced, for example, by the method of the following reaction formula: (II) [I[1] (1) [Formula In the formula, R', R'', m and n are the same as described above.] That is, sulfonyl chloride (0) and glycolic acid amide (II) are mixed with acid in an inert solvent. It is obtained by reacting in the presence of a binder.The solvent used in this reaction may be any solvent that is inert to this reaction, such as evadichloromethane, chloroform, tetracyclic carbon L 1,2-dichloro □Halogenated hydrocarbons such as loethane, n-hexane,
Aliphatic hydrocarbons such as cyclohexane, aromatic hydrocarbons such as benzene and toluene, ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether, tetrahydrofuran and dioxane, acetonitrile,
Examples include nitriles such as propionitrile. Examples of the acid binder include organic bases such as pyridine and triethylamine, and inorganic bases such as sodium hydroxide and potassium carbonate. This reaction can be carried out over a wide temperature range of -50°C to 150°C, but the reaction is slow at low temperatures.
From the viewpoint of side reactions occurring at high temperatures and energy costs, the temperature is preferably -30 to 100°C, particularly preferably -
The temperature is 20-70°C.

After completion of the reaction, the compound of the present invention can be obtained by carrying out a usual post-treatment.

The herbicide of the present invention can be obtained by processing the compound of formula (1) into a formulation such as a wettable powder, emulsion, powder, granule, fine granule, aqueous solution, or sol according to the conventional formulation method for agricultural chemicals. can be used. As the carrier or diluent, commonly used solid or liquid carriers are used. As a solid carrier,
Clays and talc represented by the kaolinite group, montmorillonite group, or attapulgite group; mica, phyllite, pumice, perminiquillite, gypsum, calcium carbonate, dolomite, diatomaceous earth, gnesium lime, apatite, Inorganic substances such as zeolite, silicic anhydride, and synthetic calcium silicate; Vegetable organic substances such as soybean flour, tano flour, walnut flour, wheat flour, wood flour, starch, and crystalline cellulose; Coumaron resin, petroleum resin, and alkyd resin. , polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, dammar gum, and other synthetic or natural polymer compounds; carnauba wax, beeswax, and other waxes, and urea.

Suitable liquid carriers include: kerosene, mineral oil, spindle oil, white oil, etc.) fluorine-based or naphthenic hydrocarbons; benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene, etc., aromatic hydrocarbons; Carbon chloride, chloroform, trichlorethylene,
Chlorinated hydrocarbons such as monochlorobenzene and 0-chlorotoluene; Ethers such as dioxane and tetrahydrofuran; Acetone, methyl ethyl ketone, diisobutyl 2
ke12,'7,,o,,yakashi2,aya) 7:
c/:y, ketones such as isophorone: ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, diptyl maleate, co□
, esters such as diethyl succinate; methanol, n□,
- Alcohols such as hexanol, ethylene glyconyl, diethylene glycol, cyclohegisanol, benzyl alcohol: ethylene glycol ethyl ether,
Ethylene glycol phenyl, diethylene glycol ethyl ether, diethylene glycol butyl ether, and other ether alcohols, polar solvents such as dimethylformamide, dimethyl sulfoxide, and water, etc. Emulsification, dispersion, wetting, and spreading. Surfactants used for purposes such as expansion, binding, disintegration adjustment, stabilization of active ingredients, and improvement of fluidity - rust prevention are nonionic, anionic, ・ □・
: Both cationic and zwitterionic 9 can be used, but usually non-ionic and/or
Anionic substances are used. Suitable nonionic surfactants include, for example, those obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl almal, sugearyl alcohol, and oleyl alcohol; and those obtained by polymerizing and adding ethylene oxide to alkylphenols such as inoctylphenol and nonylphenol. Products made by polymerizing and adding ethylene oxide and cyto to alkylnaphthols such as nibylnaphthol and octylnaphthol; products made by polymerizing and adding ethylene oxide to high-quality fatty acids such as palmi, cic acid, stearic acid, and oleic acidQ; Products obtained by polymerizing and adding ethylene oxide to monomodal or dialkyl phosphoric acids such as stearyl phosphoric acid and dilauryl phosphoric acid.Products obtained by polymerizing and adding ethylene oxide to amines such as nidodecylamine and stearic acid amide: Higher polyhydric alcohols such as norbitane. Fatty acid esters and those obtained by polymerizing and adding ethylene oxide to them: those obtained by polymerizing and adding ethylene oxide and propylene oxide, etc. Suitable anionic surfactants include, for example, alkyl sulfate ester salts such as sodium lauryl sulfate and oleyl alcohol sulfate ester amine salt; alkyl sulfones such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulfonate. Acid salts: Sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate 1) Arylsulfonates such as rum, sodium ligninsulfonate, and sodium dodecylbenzenesulfonate.

In addition, the compounds of the present invention may contain polymeric compounds such as casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, and other auxiliaries for the purpose of improving the properties of the preparation and increasing herbicidal activity. Agents can also be used in combination.

The above-mentioned carriers and various auxiliary agents are used individually or in combination as appropriate depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.

~ The content of the active ingredient of the compound of the present invention in the various formulations obtained in this manner varies depending on the formulation, but is 0.1 to 99% by weight, preferably 1 to 80% by weight. For example, 5 to 80% by weight in water preparations, 10 to 60% by weight in emulsions, and 1 to 15% in granules.
Preferably, it is used in % by weight.

The amount of the compound of the present invention to be used can be adjusted as appropriate depending on the application situation, method of use, type of target grass species, growth stage, and time of use, but in general, the active ingredient is 0.01 to 0.01/ha/ha. iol (g, preferably 0.1 to 4 Kf).

The compound of the present invention can also be used as a labor-saving pest control agent by appropriately mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, etc. In particular, when used in combination with a herbicide, it is expected to not only reduce the drug strength and save labor, but also to expand the herbicidal spectrum due to the synergistic action of both agents, and to achieve even higher effects due to the synergistic action. Wrap it around.

Next, the present invention will be explained in detail using synthesis examples, formulation examples, and test examples.

(Left below) Synthesis Example 1 3.3 t (0,02 mob) of 2-hydroxy-N-methyl-N-phenylacetamide and 4.29 (0,022 moA) of p-toluenesulfonyl chloride were added to 50% acetone and cooled with water. The mixture was stirred to form a solution.

Add 3.0% triethylamine to this solution. Q,fCo,,
o 3mol) while keeping the reaction temperature at 0 to 10°C.
It was added dropwise in 0 minutes and reacted. After completion of the dropwise addition, after stirring at room temperature for 4 hours, 100 d of dichloromethane was added to the reaction solution.
Washed twice with 50m+7 distilled water. After drying the organic layer using anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel chromatography using a mixture of acetone and chloroform to obtain compound A (7).
4.2 f was obtained. Yield 66%, m, p, 82-3°C
- Synthesis Example 2 The following compound was synthesized in the same manner as Synthesis Example 1.

Compound shop Physical properties (2) mp, 93~5℃ (8) #79.5~81.5# (9) Oil QI NMR (δppm) 2.43 (3H,S) 3.23 (3H,S) 4.42(
2H, S) 7.03-7.43 (6H7m) 7.
73 (2H, d) 01) mp 59-60°C Oa Oil ae NMR (δppm) 2.43-2.46 (6H, S, S') 3.34 (3
H, S) 4.45 (2H, SJ 7.20 (4H, S
) 7.28 (2H, d) 7.73 (2H, d) ae Oil (l"Omp, 105~106°C (2) l 111~112I C1182~ 831 (Foundation) Oil formulation example 1 Wettable powder Example compound point 7 20 parts Zikrite 75 parts Tsurupol 5039 (registered trade name Toho Chemical Exhibition) 2.5
At least 2.5 parts of Carplex (registered trade name, manufactured by Shionogi & Co., Ltd.) were uniformly mixed and pulverized to prepare a wettable powder.

Formulation example 2 Granule embodiment Hardware shop 2 10 parts Bentonite 421 Talc 431 Likunin sulfonic acid sorter 51 The above ingredients are thoroughly mixed and crushed, water is added, stirred and kneaded, and granulated using a normal granulation method. Granules were obtained.

Formulation Example 3 Emulsion Example Hardware Store 9 aog Kijirol 60 parts Tsurupol 800A (registered product name Toho Kagakuten) □
An emulsion was obtained by uniformly mixing and dissolving 10 parts or more.

Test example (flooded top end treatment): Paddy fields and chemical fertilizers were placed in Wagner pots with an area of 200 cI/I for three pots of each concentration, and an appropriate amount of water was added to create a sufficiently stirred condition.

After sowing a certain amount of seeds of various weeds, two rice seedlings at the two-leaf stage were transplanted. Furthermore, 95 rice seeds that had germinated in a pigeon-chest shape were sown in each pot, and the pots were submerged in water to a depth of 2 to 3 m.

On the 4th day after seeding, a diluted solution of the wettable powder of the present invention prepared according to Formulation Example 1 is added to a predetermined amount of active ingredient. It was processed as follows. Thereafter, each plant was grown in a glass greenhouse with appropriate fertilization management. 300 days after chemical treatment, the herbicidal effect and degree of chemical damage were determined according to the following criteria, and the results are shown in Table 2.

Herbicidal effect: Percentage of remaining weeds in treated areas with chemical damage level) 5: Remaining rate 0% - No chemical damage 4: l 1-20% Slight damage 3: '1 21-40% Ten minor damage 2:, # 41-60% Plant damage 1: # 61-80% Minor damage 0: # 81% or more

Claims (1)

[Scope of Claims] A herbicide for rice fields, characterized by containing a phenylsulfonyloxyacetanilide derivative represented by the following general formula. [In the formula, R1 represents a methyl group or ethyl group, R2 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, m = 0.1 or 2, n
represents 0 or 1. ]