JP2000281513A - Mixed herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition capable of exhibiting a highly herbicidal effect by a synergistic effect with a small amount of agent, having high safety to rice plant, capable of controlling many kinds of important weeds for a long period of time by one application by using both a specific pyrimidine derivative and a controller for paddy rice plant. SOLUTION: This composition comprises (A) a pyrimidine derivative of the formula (X is an alkyl or an alkoxyalkyl; R is difluoromethyl or trifluoromethy) and (B) a compound selected from 2-chloro-2',6'-diethyl-N-(n- propoxyethyl)-acetanilide, N-butoxymethyl-2-chloro-2',6'-dimethylacetanilide, 2-chloro-N-(3-methoxy-2-thienyl)methyl-2',6'-dimethylacetanilide, etc., as active ingredients. The amount of the component B mixed is 0.01-500 pts.wt., preferably 0.1-100 wt.% based on 1 pt.wt. of the component A. Preferably the composition is used for a paddy field.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a novel mixed herbicidal composition.

[0002]

2. Description of the Related Art At present, various herbicides have been developed and put into practical use as paddy field herbicides, and are widely and generally used as single agents and mixed agents. In recent years, mixed herbicides, which are composed of a plurality of herbicides and have a broad herbicidal spectrum, and are called herbicides, are widely used. However,
As for the perennial cyperaceae, which is difficult to control, perennial cyperaceae, ivy, and perennial broadleaf weeds, such as urikawa and omodaka, the control effect of these herbicides is often insufficient. In addition, the residual efficacy against the annual weed Nobies and broadleaf weeds such as the onion, or perennial weeds such as fireflies mainly breeding on the seeds is not always sufficient, and post-generation occurs due to lack of residual effects of the drug. At present, the control of these remaining weeds is carried out by spraying or taking another herbicide called a mid-term herbicide or a late-stage herbicide applied 20 to 30 days after planting.

Further, in the use of conventional herbicides, climatic conditions such as temperature, wind and light, soil conditions such as soil and soil organic matter content, cultivation management conditions such as shallow transplanting depth, use of soft young seedlings and deep water management, It is known that crop damage may occur due to various factors such as a chemical application condition such as non-uniform application or excessive application of a herbicide.

[0004]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a mixed herbicidal composition, particularly a composition useful as an agent for controlling weeds occurring in paddy fields.

[0005]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, the mixed herbicidal composition of the present invention shows that various kinds of important weeds, including nobies, occur in a wide range of paddy fields. Was controlled for a long time by one application, and it was found that rice had high safety, and the present invention was completed.

The present invention relates to the general formula

[0007]

Embedded image [In the formula, X represents an alkyl group or an alkoxyalkyl group, and R represents a difluoromethyl group or a trifluoromethyl group. A pyrimidine derivative represented by the formula
2 ′, 6′-diethyl-N- (n-propoxyethyl)
-Acetanilide (pretilachlor, compound 1), N-
Butoxymethyl-2-chloro-2 ′, 6′-dimethylacetanilide (butachlor, compound 2), 2-chloro-N- (3-methoxy-2-thienyl) methyl-2 ′,
6'-dimethylacetanilide (thenylchlor, compound 3), 2- [4- (2 ', 4'-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4-methylacetophenone (benzo Fenap,
Compound 4), 4- (2,4-dichlorobenzoyl)-
1,3-dimethylpyrazol-5-yl-p-toluenesulfonate (pyrazolate, compound 5), 2,4-bis (ethylamino) -6-methylthio-1,3,5-triazine, (simetrine, compound 6) , 2-Ethylamino-4- (1,2-dimethylpropylamino) -6-methylthio-1,3,5-triazine (dimetamethrin,
Compound 7), 4- (4-chloro-2-methylphenoxy) butyric acid (MCPB, compound 8), 2- (2,4-dichloro-3-methylphenoxy) propionanilide (chromeprop, compound 9), 2- ( 2-naphthyloxy) propionanilide (naproanilide, compound 1)
0), S- (4-chlorobenzyl) N, N-diethylthiocarbamate (benthiocarb, compound 11), S-
(1-methyl-1-phenylethyl) piperidine-1-
Carbothioate (dimepiperate, compound 12) 2-
Bromo-N- (α, α-dimethylbenzyl) -3,3-
Dimethylbutyramide (bromobutide, compound 13),
1- (α, α-dimethylbenzyl) -3- (4-methylphenyl) urea (Dimron, compound 14), 2-benzothiazol-2-yloxy-N-methylacetanilide (mefenacet, compound 15), N, N- Diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide (Cafentrol, compound 16), 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-isopropyl Riden-1,3-oxazolidine-2,4-dione (pentoxazone, compound 17), 2,3-dihydro-
3,3-dimethylbenzofuran-5-ylethanesulfonate (benfresate, compound 18), 3-isopropyl-3H-2, 1,3-benzothiadiazine-4 (3
H) -one 2,2-dioxide (bentazone, compound 1
A mixed herbicidal composition comprising a compound selected from 9) as an active ingredient, particularly a mixed herbicidal composition useful as a weed controlling agent in paddy fields.

The sulfonylanilide derivative represented by the general formula used in the present invention is a compound which the present inventors have found to be safe in rice and to have a herbicidal effect (Japanese Patent Application No. 10-214635). No. and Japanese Patent Application Hei 10-
No. 235438). This sulfonylanilide derivative is
Despite having a wide spectrum of weed killing, controlling high-growth and perennial weeds requires high doses, and using high doses may reduce the safety against rice .

On the other hand, pretilachlor, butachlor,
Tenylchlor, benzofenap, pyrazolate, simethrin, dimethamethrin, MCPB, clomeprop, naproanilide, benthiocarb, dimepiperate, bromobutide, dimelone, mefenacet, cafentrol, pentoxazone, benfresate, bentazone are herbicides commonly used as herbicides for paddy rice. However, it is difficult for these agents to control weeds such as gramineous weeds, broadleaf perennial weeds, and cyperaceae perennial weeds simultaneously with a single compound, and moreover, from before the onset until the growing season. Further, in order to control weeds that have grown, a high dose is required, in which case it is difficult to ensure safety against rice.

The present invention relates to a sulfonylanilide derivative represented by the general formula and pretilachlor, butachlor, tenylchlor, benzofenap, pyrazolate, simethrin, dimethamethrin, MCPB, clomeprop, naproanilide, benthiocarb, dimepiperate, bromobutide, dimbutrone, mefenaspent, cafenstrole, cafenstrole, And a compound selected from benfresate and bentazone as an active ingredient, particularly a mixed herbicidal composition useful as an agent for controlling weeds generated in paddy fields.

Representative examples of the pyrimidine derivative represented by the general formula used in the present invention are shown below. The compound numbers will be referred to in the following description. Representative examples of the sulfonylanilide derivative used in the present invention are shown below, but the present invention is not limited thereto.

[0012]

[Table 1]

X of the pyrimidine derivative represented by the general formula used in the present invention is an alkyl group, an alkoxyalkyl group,
It is preferably a lower alkyl group or a lower alkoxy lower alkyl group, and the lower of the lower alkyl and the lower alkoxy means an integer having 1 to 4 carbon atoms.

The pyrimidine derivative represented by the general formula used in the present invention is an ortho-pyrimidinylmethylaniline derivative obtained by condensing an orthohalogenonitrobenzene derivative and a pyrimidinylacetonitrile derivative, followed by oxidative decyanation and reduction. Can be prepared by sulfonylation with a halogenomethylsulfonyl halide or a corresponding acid anhydride. These compounds and methods for producing the compounds are described in JP-A-11-60562, "Sulfonanilide Derivatives and Herbicides", and Japanese Patent Application No. 10-214635, "Difluoromethanesulfonanilide Derivatives, a method for producing the same and a herbicide containing the same as an active ingredient. , Japanese Patent Application No. 10-2354
No. 38 `` trifluoromethanesulfonylanilide derivative,
Production method and herbicide containing the same as active ingredient ".

[0015] The mixing ratio of the mixed herbicidal composition of the present invention
Grass type, weed condition, spraying time, useful crop type, etc.
Depending on the requirements and can be mixed over a wide range as needed
It is necessary to change the ratio and the amount of application. The mixing ratio is
Generally, 1 part by weight of the pyrimidine derivative used in the present invention
For pretilachlor, butachlor, and teniluku
Roll, benzofenap, pyrazolate, simetry
, Dimethamethrin, MCPB, clomeprop, nap
Roanilide, Benthiocarb, Dimepiperate, Bromo
Butide, Daimlon, Mefenacet, Kafenstro
, Pentoxazone, benfresate, bentazone
0.01 to 500 parts, preferably 0.1 to 100 parts,
More preferably, it is desirable to mix in the range of 1 to 50 parts.
Good.

More specifically, 2 parts to 50 parts of pretilachlor, 2 to 50 parts of butychlor, 2 to 50 parts of terenylchlor, 2 to 50 parts of benzophenap, 2 to 50 parts of pyrazolate, 2 to 50 parts of simethrin and 2 parts to pyrimidine derivative 50 parts, dimetamethrin 2 to 50 parts, MCPB2
~ 50 parts, clomeprop 2-50 parts, naproanilide 2-50 parts, benthiocarb 2-50 parts, dimepiperate 2-50 parts, bromobutide 2-50 parts, Daimron 2
It is preferable to mix 2 to 50 parts of mefenacet, 2 to 50 parts of cafenstrole, 2 to 50 parts of pentoxazone, 2 to 50 parts of benfresate or 2 to 50 parts of bentazone. Pyrimidine derivatives and pretilachlor,
Butachlor, tenylchlor, benzofenap, pyrazolate, simethrin, dimethamethrin, MCPB,
A good herbicidal effect can be obtained even when one or more of clomeprop, naproanilide, benthiocarb, dimepiperate, bromobutide, dimelone, mefenacet, cafentrol, pentoxazone, benfresate and bentazone are mixed together.

The mixed herbicidal composition of the present invention may be mixed with an insecticide, a fungicide, another herbicide, a plant growth regulator, a fertilizer, and the like, if necessary.

The mixed herbicidal composition of the present invention may be used by mixing the active ingredients as they are, but may be mixed with commonly used carriers, surfactants, dispersants or auxiliaries to form powders, hydrates and the like. It is preferable to use the composition as a preparation such as an agent, a flowable, an emulsion, a liquid, a granule or a fine granule.

[0019] Carriers used in the formulation include:
For example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane, methylnaphthalene, water, and the like can be given. .

Examples of the surfactant and dispersant include metal alkyl benzene sulfonate, metal dinaphthyl methane disulfonic acid, alcohol sulfate, alkyl aryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, and polyoxyethylene glycol ether. Oxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the adjuvant include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like.

The mixed herbicidal composition of the present invention is applied directly at the time of use or diluted to a concentration suitable for the purpose of use, and is used by foliage application, soil application or water application.

The amount of the active ingredient in the preparation of the composition of the present invention is appropriately selected as required. In the case of a powder, a fine granule or a granule, 0.01 to 50% (by weight), preferably 0.1 to 50%. 0
It is preferable to select from the range of 5 to 30% (weight).
In the case of wettable powders, flowables, emulsions and liquids, 1
It is preferable to select from the range of -90% (weight), preferably 5-80% (weight).

The application rate of the mixed herbicidal composition of the present invention varies depending on the kind of the compound used, the target weed, the tendency to emerge, the environmental conditions, the dosage form used, and the like. In such a case, 0.1 g to 5 kg, preferably 1 g to 1 kg, per 10 ares is used as an active ingredient.
Select and use from the range of kg. In the case of emulsions, wettable powders, flowables, liquids and the like which are used as they are or diluted with water, the concentration of the active ingredient when used is generally 1 to 50,000 ppm, preferably 5 to 50,000 ppm. 1
It is appropriately selected from the range of 000 ppm and used.

[0024]

DETAILED DESCRIPTION OF THE INVENTION The present invention is used as a mixed herbicidal composition.

Next, the mixed herbicidal composition of the present invention will be described with reference to Examples and Test Examples. The types and compounding ratios of the compounds and additives are not limited to these and can be changed in a wide range. In the following description, “parts” means parts by weight.

Example 1 Wetting agent 1 part of compound P1 and 10 parts of pretilachlor were mixed with 0.5 part of polyoxyethylene octyl phenyl ether, β part
-0.5 parts of sodium salt of formalin condensate of naphthalenesulfonic acid, 20 parts of diatomaceous earth and 68 parts of clay are mixed and pulverized,
Obtain wettable powder.

Example 2 Wettable powder 0.5 part of polyoxyethylene octylphenyl ether was added to 0.5 part of compound P1 and 15 parts of benthiocarb,
0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, 20 parts of diatomaceous earth, 5 parts of white carbon, and 58.5 parts of clay are mixed and pulverized to obtain a wettable powder.

Example 3 Wettable powder 1 part of compound P2 and 10 parts of bromobutide were added to 0.5 part of polyoxyethylene octylphenyl ether, and β-naphthalenesulfonic acid formalin condensate sodium salt was added.
5 parts, 20 parts of diatomaceous earth, 5 parts of white carbon and 63 parts of calcium carbonate are mixed and pulverized to obtain a wettable powder.

Example 4 Water dispersible granules In 10 parts of compound P1 and 30 parts of pentoxazone, 5 parts of sodium ligninsulfonate, 1 part of polyoxyethylene alkylaryl ether, 3 parts of sodium polycarboxylate, 5 parts of white carbon, pregelatinized One part of starch, 45 parts of calcium carbonate and 10 parts of water are added, and the mixture is kneaded, pressed and granulated. The obtained granules are dried with a fluid bed dryer to obtain a wettable powder for granules.

Example 5 Flowable agent In 71.9 parts of water, 1 part of compound P2, chrome prop 1
0 parts, sodium lignin sulfonate 2 parts, ammonium polyoxyethylene alkyl aryl ether sulfate 4
Part, polyoxyethylene alkyl aryl ether
5 parts, Kitansan gum 0.1 parts, bentonite 0.5
And 10 parts of ethylene glycol, and mixed with a high-speed stirrer, and pulverized with a wet pulverizer to obtain a flowable agent.

Example 6 Granules 1 part of compound P1, 10 parts of Daimlon, 79 parts of a bulking agent obtained by mixing talc and bentonite at a ratio of 1: 3, 5 parts of white carbon, surfactant polyoxyethylene sorbitan alkylate, poly 10 parts of water is added to 5 parts of a mixture of an oxyethylene alkylaryl polymer and an alkylarylsulfonate, and the mixture is kneaded well, extruded through a sieve having a diameter of 1 mm, dried, and then cut to a length of 0.5 to 1 mm. To obtain granules.

Next, the effects of the mixed herbicidal composition of the present invention will be described with reference to test examples.

<Test Example 1> Test of herbicidal effect by paddy field flooding treatment A 1/2000 are plastic pot was filled with paddy field soil, and after scratching, it was replaced with a foxtail (Ec) and a corn (M).
o), seeds of seedlings of Indica fireflies (Si) were sown, and tubers of Spodoptera litura (Cy) and Urikawa (Sa) were implanted, and two-leaf stage rice (Or) was transplanted.
Flooded. Formulation Example 1 was grown outdoors when the average temperature was around 20 to 23 degrees C.
A predetermined amount of a wettable powder prepared according to the above was diluted with water and dropped into submerged water. After that, it is grown again outdoors and after treatment 2
On the eighth day, the air-dry weight of each above-ground part was measured, and the herbicidal effect and the degree of phytotoxicity were indicated by indexes according to the following criteria. The results are shown in Tables 3 and 4. The dose was shown as the amount of active ingredient per 10 ares.

[0034]

[Table 2]

[0035]

[Table 3]

[0036]

[Table 4]

<Test Example 2> Test of herbicidal effect by paddy field flooding treatment A 1/2000 are plastic pot was filled with paddy field soil, and after scratching, various seeds of Tainubie (Ec) and Inuhotarii (Si) were sown. In addition, the mistletoe (C
The tuber of y) was embedded, and after transplanting the rice plant (Or) at the two-leaf stage, it was flooded to a depth of 3 cm. Average temperature 22-25 degrees C. After growing up before and after outdoors, and when the rice flour reached the two-leaf stage, a predetermined amount of the wettable powder prepared according to Formulation Example 1 was diluted with water and dropped into submerged water. Thereafter, the plants were grown outdoors again, and on the 28th day after the treatment, the air-dry weight of each above-ground portion was measured, and the herbicidal effect and the degree of chemical damage were indicated by indexes according to the criteria in Table 2. The results are shown in Tables 5 and 6. The dose is 1
It was shown by the amount of the active ingredient per 0 ares.

[0038]

[Table 5]

[0039]

[Table 6]

[0040]

EFFECTS OF THE INVENTION The mixed herbicidal composition of the present invention can be used for pre-emergence of annual weeds such as barnyardgrass, tamagatsuri and konagi which occur in paddy fields and perennial weeds such as urikawa, omodaka, mizuganatsuri, shizui, kuroguwai, firefly and sprout. From a wide range of growing seasons to a wide range of growing seasons, it shows a high herbicidal effect at a low dose due to a synergistic effect, and at the same time, a single chemical treatment can control the emergence of weeds for a long period of time, and has a high safety in rice It reduces the labor of farmers and is useful as a mixed herbicide composition.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (Reference) A01N 43/10 A01N 43/10 E 43/12 43/12 A 43/56 43/56 C 43/70 43/70 43 / 76 43/76 43/78 101 43/78 101 43/88 105 43/88 105 47/12 47/12 Z 47/16 47/16 A 47/30 47/30 C 47/38 47/38 A

Claims (2)

[Claims] 1. A compound of the general formula [In the formula, X represents an alkyl group or an alkoxyalkyl group, and R represents a difluoromethyl group or a trifluoromethyl group. A pyrimidine derivative represented by the formula:
2 ′, 6′-diethyl-N- (n-propoxyethyl)
-Acetanilide, N-butoxymethyl-2-chloro-
2 ', 6'-dimethylacetanilide, 2-chloro-N
-(3-methoxy-2-thienyl) methyl-2 ', 6'
-Dimethylacetanilide, 2- [4- (2 ', 4'-
Dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4-methylacetophenone;
4- (2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yl-p-toluenesulfonate,
2,4-bis (ethylamino) -6-methylthio-1,
3,5-triazine, 2-ethylamino-4- (1,2
-Dimethylpropylamino) -6-methylthio-1,
3,5-triazine, 4- (4-chloro-2-methylphenoxy) butyric acid, 2- (2,4-dichloro-3-methylphenoxy) propionanilide, 2- (2-naphthyloxy) propionanilide, S- (4-chlorobenzyl) N, N-diethylthiocarbamate, S- (1-methyl-1-phenylethyl) piperidine-1-carbothioate, 2-bromo-N- (α, α-dimethylbenzyl) -3 , 3-dimethylbutyramide, 1- (α, α-
Dimethylbenzyl) -3- (4-methylphenyl) urea, 2-benzothiazol-2-yloxy-N-methylacetanilide, N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1 -Carboxamide, 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-isopropylidene-1,3-oxazolidine-2,4-dione, 2,3
-Dihydro-3, 3-dimethylbenzofuran-5-ylethanesulfonate, 3-isopropyl-1H-2,
1,3-benzothiadiazin-4 (3H) -one 2,2
-A mixed herbicidal composition comprising a compound selected from dioxide as an active ingredient. 2. The herbicidal composition according to claim 1, wherein the mixed herbicidal composition is for paddy fields.