JPS5920205A - Herbicide - Google Patents

Abstract

PURPOSE:A herbicide containing a substituted phenylsulfonylurea derivative and benzothiazol-2-yloxy-acetic acid N-methylanilide and pyrazolate, and capable of exhibiting very remarkable synergistic action in a small amount of application. CONSTITUTION:A herbicide containing a substituted phenylsulfonylurea derivative of formula I [X is O or single bond; Y is H or Cl; R is formula II or III (R<1> and R<2> are methyl or methoxyl)] and benzothiazol-2-yloxy-acetic acid N-methylanilide and 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl p-toluenesulfonate (pyrazolate) preferably at 1:(75-150):(75-150) weight ratio as active constituents. EFFECT:Safe with remarkable selective controlling effects and improved lasting effects. USE:Pre-emergence soil treating and foliar and soil treating agents for weeds in paddy fields.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to herbicides exhibiting excellent biological activity.

More specifically, substituted phenylsulfonyl represented by the general formula: (in the formula, or an oxygen atom or a single bond, Y is a hydrogen atom or a ral atom, and R1 and R2 represent a methyl group or a methoxy group) L7794 Benzthiazole-nizyloxy-acetic acid N-methylanilide (hereinafter referred to as compound (A)) represented by the formula: and p-toluenesulfonic acid 9- (,2,t
The present invention relates to a weed killer (1) characterized by containing pyrazolate (hereinafter referred to as virazolate) as an active ingredient.

The seven active ingredients, the active sulfonylurea conductor represented by the general formula (1), were disclosed by the applicant in the patent application b-g.
No. 977 and patent application No. 6-/tIll! ; It is a herbicide described in Publication No. 90.

However, benzthiazole-ni-1-ruoxy-acetic acid N-methylanilide (compound (A)) was obtained from JP-A-Sho, 3i1-
It is a herbicide known from Publication No. 4Z76.2.

Further, a mixture of penduti7zole-choyloxy-acetic acid N-methylanilide [compound (A)] and a virazolate agent is a herbicide known in Japanese Patent Application Laid-Open No. 5B-T and SGOB.

Virazolate is a commercially available herbicide that can be used to control annual grass weeds such as field weeds, broad-leaved weeds, and cypress.
It is known to be effective against perennial weeds such as firefly and weed. However, /annual and perennial weeds,
For example, there is a drawback that the control effect against water snails, firefly, etc. is significantly reduced.

A variety of herbicides with excellent control activity have been developed to control weeds such as Japanese field weed, Japanese grass weed, annual broad-leaved weeds, and perennial weed Pinella 1, which have traditionally been considered the most problematic among paddy field weeds. has been used as an admixture. As a result, as the rice paddy weeds mentioned above were controlled, competition among weeds decreased, so there were many weeds that could not be adequately controlled with conventional chemicals, such as perennial grasses such as fireflies, urikawa, and water cyperus. The grass grew thick and caused damage to the rice plants.Therefore, it was necessary to develop a broad-spectrum herbicide that could simultaneously control many 8i class weeds, such as the above-mentioned perennial and/or annual weeds, and broad-leaved weeds. In particular, it is desired to develop an excellent herbicide against the perennial weed Cyperus japonica, which is a particularly harmful and harmful weed.

Paddy field weeds, such as annual weeds, broad-leaved weeds, perennial weeds, etc., grow at the same time in various stages, so it is difficult to spray the same or different herbicides at once. Systematic processing is being carried out. Therefore, it is desired to develop a herbicide that can control different types of weeds at various growth stages by spraying a low dose of the herbicide seven times, and a herbicide that can be used over a wide range of applications during the suitable treatment period.

As a result of intensive research in order to solve the above problem, the present inventors have found that the herbicide of the present invention has accurate results when each constituent agent and each Type A mixture are used alone in a conventional manner. Even for grass species that do not exhibit a control effect, extremely significant cooperative and synergistic effects work at low application rates to achieve fully satisfactory selective weed control and to obtain a wide spectrum of weed control. I learned. In particular, in the control of perennial weeds such as water cypress, which are currently difficult to control,
For example, the herbicide of the present invention has a remarkable synergistic effect, has a rapid onset of herbicidal effect, and has an accurate herbicidal effect even in extremely overgrown paddy fields and extremely overgrown paddy fields with water leakage.
The present invention has been completed by solving the economical problem of causing no chemical damage to rice, showing sufficient effect after two treatments, maintaining its effectiveness for a long period of time, and controlling pest control at a low application rate.

Therefore, an object of the present invention is to provide a novel mixture, particularly a herbicide, and the present invention has been completed based on the above discovery.

Preferred examples of the substituted phenylsulfonylurea derivative represented by the general formula (+) used in the herbicide of the present invention include the following compounds.

1/7
, mp, '99-20.2. °C compound 1st month (
2) N-Ω-biphenylylsulfonyl, N'-(<7.6-
dimeglubilimidine, 2-4) urea, mp,
2.03~,2ogc Compound Natsuki (3) N-,1--y/quinphenylsulfonyl, N'-(
Goumetquin-6-methyl-pyrimidine-norl)urea, mp/9~, 20θ℃ Compound number (/l) N-2-(2-/rolphenoxy)phenylsulfonyl, N'-(4-methoxy- Otsu-methyl-pyrimidine-Ω-zuru) urea, mp, 2. / bN, 2.2
(,7℃ Compound number (,1t) N-,2-phenoxyphenylsulfonyl, N'-(q
, 4-dimethyl-pyrimidine-niyl)urea, oral]
177g~7g0℃ Compound number (ro) N-,)-biphenylylsulfonyl, N'-('<j-
Methoxy-O-methyl-/, 3,3-triazine-niyl)urea, mp/90~/93°C Compound No. (7) N-λ-biphenylylsulfonyl, N'-(4,4-dimethoxy-/, , 3. Left-triazine-flood-vine) urea, mp/7. t~/gO℃ Compound number (g) N-,2-phenoxyphenylsulfonyl, N'-(q
-methoxy-ot-methyl-/, 3. ! -) riazine-niyl)urea, [7g3-790℃ Compound No. (9) N-,2-phenoxyphenylsulfonyl, N'-(g
, O-dimethoxy-/, 3.3-) riazine-a-1
Le) Urea, mp/60~//,! r℃ compound number (1
0) N-2-(,21'rolphenoxy)phenylsulfonyl, N'-(tl,6-simethoxy7.3.3-triazin-2-1l)urea, mp 20 /~20q°C
.

Non-explosion (destructive agent d), low toxicity to warm-blooded animals,
71 good for cultivated plants? Since fElj has the property of being harmful to cultivated plants in winter, that is, it does not cause any phytotoxicity to cultivated plants at the usual concentration, it can be conveniently used as a deterrent to control weeds. The word weed here means all plants that grow in undesirable locations in the widest range of areas.

The herbicide of the present invention exhibits excellent selective control efficacy and excellent persistence of efficacy, particularly when used as a pre-emergence soil treatment agent for paddy field weeds or as a foliage and soil treatment agent.

As mentioned above, the mixed agent of Fuwari 1 is excellent in safety and exhibits excellent herbicidal activity, exhibiting a wide herbicidal spectrum and excellent persistence of efficacy.

It has the characteristic that it has no harmful effect at all.

When using the herbicide of the present invention, either dilute it directly with water and use it directly, or use a pesticide adjuvant to remove the herbicide.
It can be used in various formulations using methods commonly practiced in the Z field. In actual use, these various formulations can be used directly or diluted with water to a desired concentration. Examples of agricultural chemical auxiliaries mentioned here include diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, dispersants, wetting agents), stabilizers, and fixing agents.

Solvents include water: organic solvent; hydrocarbons [for example, naphtha, petroleum fractions (paraffin wax, kerosene, light oil, middle oil, heavy oil), benzene, toluene, xylenes], halogenated hydrocarbons [for example, Chlormethylene, carbon tetrachloride, trichlorethylene, ena L/chloride, tooled ethylene, chlorobenzene, chloroform], alcohol 1
Example 1j: Methyl alcohol, ethyl alcohol, flobyl alcohol, ethylene glycol], ethers [
For example, ethyl ether, ethylene oxide, dioxane], alcohol ether (e.g., ethylene glycol monomer ether), ketone 9:AC (e.g. IrJ), setone, inholon], esters [
Examples include ethyl acetate, amyl acetate], amide Fs [eg, dimethylformamide, dimethylacetoamide], and sulfoxides [eg, dimethylsulfoxide].

Inorganic materials such as slaked lime, magnesium lime, gypsum, calcite, sandstone, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zemerat, clay minerals (Example 9... Its ,
Ha<lofila, talcum, montmorillon, bar, vermicular, kaolinite, cloud): Plant organic substances such as: flour, starch, processed denso, sugar,
Glucose, 1 cup of crushed plant stems: Synthetic resins such as phenol resins, urea resins, and vinyl chloride resins.

Kai ■ 11 live bamboo 'A1j is anion (yin 1 on)
Surface-active alkyl sulfate esters (e.g. monolithium lauryl sulfate), esters of esters (e.g. alkylaryl sulfonate, sodium alkylnaphthalene sulfonate), polyester salts, polyethylene glycol alkyl Aryl ether sulfate ester salts: Cationic surfactants; Alkylamines [e.g., laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzyl ammonium chloride], polyoxyethylene alkylamines: Nondion Surfactant; polyoxyethylene glycol ethers [e.g., polyoxyethylene alkylaryl ether and condensates thereof], polyoxyethylene glycol esters C91-1, e.g., polyoxyethylene fatty rR ester], polyhydric alcohol esters [For example, polyoxyethylene sorbitan monolaurate] diampholytic surfactants, etc. can be mentioned.

Other stabilizers, fixing agents [e.g., agricultural soap, Kazezun lime, sodium alginate, polyvinyl alcohol (
PVA), vinyl acetate adhesive, and acrylic adhesive].

The mixed active compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Examples of formulation forms include emulsions, oils, wettable powders, suspensions, powders, granules, powders, tablets, capsules, and the like.

This herbicide contains 0.00% of the mixed active ingredient Ail. /~7
It can be contained in an amount of 0.00 weight percent, preferably 1 to 9 weight percent.

In actual use, the above-mentioned ready-to-use preparations and ready-to-use preparations are used.
The content of mixed active compound in the active compound is generally 0.01
~9 SIU, preferably 0. The range of O5-Otsu θ Jubunichi is appropriate.

The content of these mixed active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, and weed growth status.

The herbicide of the present invention may also be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, carminicides, antiviral agents, herbicides,
Plant growth regulators [e.g., organophosphoric ester compounds, carbamate compounds, dibuo (thiol)]
A carbamate-based compound, a carbamate-based compound, a dinitro-thread compound, an organic sulfur or gold layer-based compound, an antibiotic, a substituted diphenyl ether-based compound, a urea-based compound, a triazine-based compound] or/and fertilizer, etc. can also be co-existed. .

Various formulations or ready-to-use preparations containing the mixed active ingredients of the invention.
(ratio) refers to application methods and spraying (e.g., liquid spraying (spraying)) commonly used in the agricultural chemical manufacturing field.
, dusting, granulation, water surface application]: Can be carried out by soil application [for example, soil mixing], etc.

The application amount per unit area is based on each active ingredient,
Benzthiazole-2-4yloxyacetic acid N-methylanilide [Compound (A)] 550 to 2 parts by weight of the substituted phenylsulfonylurea derivative of the general formula ([)]
00 parts by weight Bilagrate 30 to 200 parts by weight, preferably 375 to 200 parts by weight of [Compound (A)]
At a mixing ratio of 7 parts by weight of ISO and 7 parts by weight of virazolate to 0 parts by weight, approximately 0.0 parts by weight of mixed active compound per hectare.
3~/,, to 2? , preferably 0. S ~ 0.9h is used for 1, but in special cases it is possible, and sometimes even necessary, to exceed these ranges. .

The present invention uses a compound selected from a substituted phenylsulfonylurea derivative represented by the general formula (1) as an active ingredient and a benzthiazole-flood-yloxy-acetic acid N-methyl-rnilide represented by the formula (n). [Compound (A
)] and virazolate, and a herbicidal composition containing a diluent (solvent and/or filler and/or carrier) and a surfactant, and if necessary, for example, a stabilizer and a fixing agent. #! - to be done.

Furthermore, the present invention applies the mixed active compound of the present invention alone to the outside cars and their growth areas, and also uses a diluent (solvent and/or filler and/or carrier) and/or a surfactant. An external control method is provided in which the above herbicidal composition is mixed with a herbicidal agent and, if necessary, a stabilizer and a fixing agent.

Next, the content of the present invention will be specifically explained using an actual Mlj example, but the present invention should not be limited to this only.

Examples/(Granules) Compound No. (3) 0.07 parts, compound of formula (II) (
A) Add 25 parts of water to a mixture of 7 parts of birazolate, 29 parts of bentonite (montmorillonite), 44.99 parts of talc, and 2 parts of lignosulfonate, knead well, and extrude into a granulator. The mixture is made into granules of 10 to 4 t0 mesh and dried at 4 to s θ°C to form granules. Sprinkle this on weeds and/or their growing areas.

Example 2 (granules) Compound number (7) θ, 07 parts, compound of formula (II) (A
) 7 parts, birazolate/part, bentonut, 29 parts, talc filter, 99 parts, lignin sulfonate 2 parts, add 2 parts of water, mix well, and extrude. Using a granulator, it is made into 10 to qO mesh granules and dried at 110 to 30°C to form granules. Sprinkle this on grass and/or where they grow.

Example 3 (powder) Clay mineral particles 9 having a particle size distribution of 0.00, 2 to 2, 9
Part g was placed in a mixer, and while rotating, 0.0.2 parts of Compound No. After extinguishing with @, dry at ll-θ~left OC to form granules. Sprinkle this on weeds and/or their growing areas.

Example t1. (Irrigation agent) Compound Bangetsu (3) 0.7 parts, compound of formula (It) (A
), 110 parts of Biragley, 711.9 parts of a polymer of powdered diatomaceous earth and powdered clay (/: 5), 1 part of sodium ammonzene sulfonate, and 3 parts of sodium alkylnaphthalene sulfonate polymeric condensate were ground and combined. 1. Use as a hydrating agent. Dilute this with water to remove weeds and/or
Or drop it onto the growing area.

Example left (emulsion) Compound delivery (7) θ, 2 parts, compound of formula (11) (A
), 20 copies, Billa plate 20 copies, Kinren tlo copy,
Methyl ethyl ketone 4'4&ll, 3 parts of polyoxene ethylene alkylphenyl ether, and 7 parts of calcium alkylbenzenesulfonate were mixed and stirred to form an emulsion. This is diluted with water and dripped onto weeds and/or their growing areas.

The unexpected superiority and remarkable efficacy of the mixed active compounds of the invention can be seen from the following test results when used against various paddy weeds.

Test example/ Control test of paddy field weeds by application in flooded sewage Test method: 1) Chemical treatment before rice transplant Weeds were artificially inoculated in the previous year, and a field where they were fully infested this year was used as a test. The field was harvested in spring, and the final planting was done s days later. Immediately after that, the field was expanded to 30 m2 (/O
m x 3 m) using a hard plastic sheet. Thereafter, a drug prepared in the same manner as in Example No. above was applied in water. Three days after applying the chemical, rice seedlings were grown in a special seedling box using a powered rice transplanter (/left eye leaf reiyu)
3-S plants per 7 plants were transplanted. The depth of water loss in the field is about 3 cm every 7 days.
The water depth υ was maintained at 3 to left cnt for a long period of time. After d weeks of chemical application, the control effect was investigated according to the latter criteria.

2) Chemical treatment test method after transplanting paddy rice The method described in 1) was followed until the final planting, and 3 days after the final planting, the water depth in the field was adjusted to 7 to 2 cm.
Paddy rice was transplanted using a power rice transplanter in the same manner as hIJ test method 1). Immediately after transplantation, the cells were divided into 30 m2 (#/m x 3 m) sections using hard plastic sheets. The water depth in the field is about 3 cm every 7 days, and the water depth is 3 cm for a long time! ; The control effect was investigated according to the criteria described below.

The evaluation of effectiveness is when compared to the untreated area.Left: Weed killing rate over the untreated area 95 cm or more (dead) 4t: Weed killing rate over the untreated area gO% or more and less than 93% 3: Weed killing rate SO% vs the untreated area 2: Weed killing rate for untreated area 30 or more and less than θ Chu/: Weed killing rate for untreated area 1
0 chi or more and less than 3θ so 0: Weed killing rate 10% compared to untreated area
Less than (no effect) Evaluation of phytotoxicity to paddy rice "0" indicates no phytotoxicity. The test results are shown in Tables 1 and 2.

Table 1 Note: Compound No. (7) represents the same N-,2-biphenylylsulfonyl, N'-(ti, b-cymethquine/3.tertriazine-2-1)urea as described above.

Compound (A) is the same benzthiazole-,
2--1 shows N-methylanilide.

Virazolate is the same p-toluenesulfonic acid p-(2+'l-dichlorobenzoyl)-/, 3
- Simeralvirazole - Left - Shown.

(1 blank space below) Table 2 Note) Compound number (7) is the same N-,2-biphenylylsulfonyl, N'-(tl,ly-sil) as above.
3-triazine-2-1) shows urea.

Compound (A) is the same penzthiazole 2 as described above.
-/I represents N-methylanilide.

Virazolate is the same as above 1)-toluenesulfonic acid'l-(2,'l-dichlorohair 7'/1
)-/, 3-dimethylpyrazol-5-4.

The above M'L: The test results show the effects of some representative examples of the active ingredients of the herbicide of the present invention, and other compounds can also be tested in similar tests to show the same extremely excellent synergistic effects. Shows selective herbicidal effect.

E. The invention, which has been explained in detail in the detailed description of the invention, can be summarized as follows.

(1) Substituted phenylsulfonylurea represented by the general formula: (wherein, X is an oxygen atom or a bond, Y is a hydrogen atom or a chloro atom, and R1 and R2 are a methyl group or a methoxy group) A compound selected from derivatives and benzthiazole-2-4yloxyacetic acid N represented by
-methylanilide and p-toluenesulfonic acid K -(2,'1
-dichlorobenzole)-/, 3-dimethylpyrazole-, 3--4 as an active ingredient.

(2)' At+ notation # The substituted phenylsulfonylurea derivative of formula (l)/parts by weight,
) of benzdeazole-,2-1-loxyacetic acid N-methylanilide Sθ~200 parts p- of the formula (In)
Toluenesulfonic acid 11-(,2,ll-dichlorobenzodur)-/,3-dimethylpyrazol-l-yl 5
0 to 200 parts by weight, preferably the general formula (1) (D
M-substituted phenylsulfonylurea derivative/in heavy μ part: 1 (
LJ, benzthiazole-λ-1-ruoxyacetic acid N-methylanilide 7S to 0 parts by weight of the above formula (■), $
, 1 of formula (m) p-)luenesulfonic acid (,2,
4Z-dichloropene, zodur) -/, 3-dimethylpyrazol-yl 7-/SO in a proportion of parts by weight of the herbicide.

(3) 611 active ingredient at 0.0/~9% by weight
, preferably from 0.0 to 40% by weight.

(4) ^ti pQ A compound selected from substituted phenylsulfonylurea derivatives of general formula (1) and penzthiazolesuyloxyacetic acid N of formula (II)
- For the control of weeds with a mixed active compound of methylanilide and p-toluenesulphonerll'l-(2,11,-dichlorobenzodur)-/,3-dimethylpyrazole-tal of the formula (III) A method for controlling weeds, which comprises applying an effective amount of the following to weeds and/or their growing areas.

(5) The method for controlling weeds according to item 9 above, wherein the weeds are paddy field weeds.

(6) the application rate of said mixed active compound is 9/ha/ha;
0.3-8-2Ky% preferably 0. s~θ, 9Ky
The method for controlling weeds according to item 9 above.

(7) Substituted phenylsulfonylurea derivative of the general formula (+) of M and benzthiazol-λ-yloxyacetic acid N of the formula (■) on weeds and/or their growing areas.
-Methylanilide and the formula (■) (7) p-) luenesulfone rR'l -(2,II-dichlorobenzodur)-/, 3-dimethylpyrazole-3-dil, individually, or applying said herbicide mixed with diluents (solvents and/or fillers and/or carriers) and/or surfactants and, if necessary, e.g. stabilizers, fixing agents. A method of deterrent power.

Agent's name: Kawahara 1) - Ho

Claims (1)

[Claims] A substituted phenylsulfonylurea derivative represented by the general formula: (wherein, and,
penzthiazole-choyloxy-acetic acid N-methylanilide and p-toluenesulfonic acid 4Z-(2,'l
-dichloropenzole)-7,3-dumepulvirazol-5-yl as an active ingredient.