JPH0551304A - Herbicide composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide composition showing synergistically increased herbicidal effects by using both a herbicidal oxyacetamides and a herbicidal compound, having high herbicidal effects and herbicidal spectrum with a small amount of the agent. CONSTITUTION:(A) A herbicidal oxyacetamides shown by the formula (R<1> and R<2> are halogen or R<1> and R<2> may be subjected to benzo condensation with ring to which R<1> and R<2> are bonded or the ring may be replaced with halogen; further R<1> is CN; R<3> is Y or 1-4C alkyl; X is 0 or S; n is 0 or 1) such as 4,5- dichlorothiazol-2-yloxy-N-methylacetanilide and (B) one or more herbicidal components selected from among a herbicidal sulfonamide, a herbicidal pyrazole, a herbicidal propionanilide, a herbicidal triazine, a herbicidal carbamate, a herbicidal diphenyl ether and a herbicidal acid amide are blended as active ingredients to give a herbicide composition having the above-mentioned effects, a wide application width and excellent residual effects.

Description

Detailed Description of the Invention

[0001]

This invention relates to herbicidal compositions. More specifically, the present invention relates to a mixed herbicide containing known herbicidal oxyacetamides and known herbicidal compounds as active ingredients.

[0002]

2. Description of the Related Art It is already well known that oxyacetamides have herbicidal activity. (Japanese Patent Publication Sho 61-4
395, JP-A-55-147267, JP-A-60-24.
6379, JP-A-1-47774, JP-A-2-4547.
(See 7 etc.) These oxyacetamides are particularly noted as an active compound that exerts a strong herbicidal action on weeds that thrive in paddy fields, especially on the fly, and does not cause phytotoxicity on paddy rice. ..

[0003]

In addition to the characteristics of the above-mentioned active compounds, in addition to strong demands such as reduction of pesticide use, expression of herbicidal effect at low doses, extension of herbicidal spectrum, etc., Development of a more preferable herbicide composition is desired.

[0004]

[Means for Solving the Problems]

[Chemical 2] In the formula, R ¹ represents a halogen atom or cyano, R ² represents a halogen atom, R ¹ and R ² together may be benzo-fused with a ring to which they are bonded, Is optionally substituted by a halogen atom, R
³ represents a C _1-4 alkyl group, X represents O or S,
Y represents a C _1-4 alkyl group, and n represents 0 or 1, and herbicidal oxyacetamide, herbicidal sulfonamides, herbicidal pyrazoles, herbicidal propionanilides, herbicidal Triazines, herbicidal carbamates, herbicidal diphenyl ethers, and at least one selected from the group consisting of herbicidal acid amides, a herbicidal composition characterized by containing as an active ingredient particularly high herbicidal activity I found it.

Surprisingly, the herbicidal composition of the present invention has a substantially higher herbicidal effect than the sum of the effects of each of the active compounds as compared with the case of using each of them alone. As a result, when controlling weeds, it is possible to substantially reduce the concentration of each individual drug that has been used so far, and at the same time obtain a broad herbicidal spectrum, and the suitable treatment period for a long time. In addition, for example, in paddy rice cultivation, it exhibits an excellent herbicidal effect from the initial stage of weeding immediately after transplantation to the growing season, and has a long-lasting effect, excellent residual effect, and phytotoxicity to rice. It shows excellent herbicidal effect.

In the formula (I) of the active compound in the herbicidal composition of the present invention, preferably R ¹ is chloro,
Or cyano, R ² represents chloro, and R ¹ and R
² together may form a chloro-substituted benzofused with the ring to which they are attached, R ³ is methyl or isopropyl, X is O or S, Y is methyl, And n shows 0 or 1.

Specific examples of the compound of formula (I) include, for example, 4,5-dichlorothiazol-2-yloxy-N.
-Methylacetanilide, 6-chlorobenzoxazol-2-yloxy-N-methylaceto (2-methylanilide), 6-chlorobenzoxazol-2-yloxy-N-methylaceto (3-methylanilide), 5-
Chloro-4-cyanothiazol-2-yloxy-N-
Methyl acetanilide, 6-chlorobenzoxazol-2-yloxy-N-isopropylaceto (3-methylanilide), and 7-chlorobenzothiazole-2-
Iloxy-N-methylacetanilide can be exemplified.
These compounds are already known compounds. (Japanese Patent Laid-Open Nos. 54-154762, 55-147267, 6)
0-246379, JP-A-1-47774, and 2-
(See 45477)

On the other hand, specific examples of the herbicidal sulfonamides include, for example, N-2-biphenylylsulfonyl.
N '-(4,6-dimethoxy-1,3,5-triazin-2-yl) urea, ethyl 5- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl]
-1-Methylpyrazole-4-carboxylate, methyl 2- [3- (4,6-dimethoxypyrimidine-2-
Il) ureidosulfonylmethyl] benzoate, 3-
(4,6-dimethoxy-1,3,5-triazine-2-
Yl) -1- [2- (2-methoxyethoxy) -phenylsulfonyl] urea, N- (2-chloroimidazole [1,2-a] pyridin-3-yl-sulfonyl)-
N '-(4,6-dimethoxy-2-pyrimidyl) urea, and N'-(4,6-dimethoxypyrimidine-2-
Il) -N "-(4-methylphenylsulfonylamino) -N""-(4-ethoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -guanidine. These compounds are also well known. (JP-B-59-481, JP-A-57-11237).
9, ibid. 57-56452, ibid. 59-122488, JP-A-1-38091, ibid. 1-70475).

Specific examples of the herbicidal pyrazoles include 4- (2,4-dichlorobenzoyl) -1,3-
Dimethylpyrazol-5-yl p-toluenesulfonate, 2- [4- (2,4-dichlorobenzoyl) -1,
3-dimethylpyrazol-5-yl] acetophenone,
And 2- [4- (2,4-dichloro-m-toluoyl)
-1,3-Dimethylpyrazol-5-yloxy] -4
-Methyl acetophenone can be illustrated. Specific examples of herbicidal propionanilides include, for example, 2- (β-naphthyloxy) propionanilide and (RS) -2.
An example is-(2,4-dichloro-m-tolyloxy) propionanilide. Specific examples of the herbicidal triazines include, for example, 2,4-bis (ethylamino) -6-
(Methylamino) -1,3,5-triazine, and 2-
An example is ethylamino-4- (1,2-dimethylpropylamino) -6-methylthio-1,3,5-triazine.

Specific examples of herbicidal carbamates include:
For example, S-p-chlorobenzyl diethylthiocarbamate, S-1-methyl-1-phenylethylpiperidine-1-carbothioate, and S-benzyl 1,
2-dimethylpropyl (ethyl) thiocarbamate can be illustrated. Specific examples of herbicidal diphenyl ethers include, for example, 2,4,6-trichlorophenyl-4′-
Examples include nitrophenyl ether and 2,4-dichlorophenyl-3'-methoxy-4'-nitrophenyl ether. Specific examples of the herbicidal acid amides include (RS) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutyramide. The above-mentioned active compounds are Pesticide Man
ual (Pesticide Manual), 1991, T
he British Crop Protect C
It is a known herbicidal compound described by Ouncil.

In the herbicidal composition of the present invention, the mixing weight ratio of the active ingredients can be varied within a relatively wide range. Generally, 0.01 to 2 parts by weight of herbicidal sulfonamides per 1 part by weight of the compound of formula (I), preferably
0.05 to 1 part by weight, herbicidal pyrazoles 2.5 to 3
5 parts by weight, preferably 3 to 15 parts by weight, herbicidal propionanilides 0.6 to 50 parts by weight, preferably
2.0 to 28 parts by weight, herbicidal triazines 0.06 to
10 parts by weight, preferably 0.15 to 6 parts by weight, herbicidal carbamates 3 to 15 parts by weight, preferably 5-1
0 parts by weight, 5 to 35 parts by weight of herbicidal diphenyl ethers, preferably 7 to 15 parts by weight, and 3.5 to 25 parts by weight of herbicidal acid amides, preferably 4.0 to 10 parts by weight. Can be used respectively.

The mixed composition according to the invention exhibits a strong herbicidal effect. Therefore, the composition can be used as a herbicide composition, and particularly preferably as a selective herbicide for paddy rice. The herbicidal composition of the present invention can be used for the following paddy field weeds, for example. Dicotyledons of the following genera : Polygonu
m), Capsicum genus (Rorippa), Scutellaria (Rotala), Genus Agena (Lindernia),
Bidens, Abuta (Dopat)
rym), genus Takasaburo (Eclipta), genus Ezotine (Elatine), genus Oobanome (Gra)
tiola), Capsicum (Linderni)
a), genus Ludwigia, genus Oenanthe, genus Ranuncu
lus), Pepper (Deinostem)
a). Monocotyledonous plants of the following genera : Echinochlo
a), genus (Panicum), genus Poa (Poa), genus Cyperus (Cyperus), genus Astragalus (Monochoria), genus Acacia (Fi)
mbristylis), genus Kwai (Sagittar
ia), genus Eleocharis, genus Firefly (Scirpus), genus Heramode (Alism)
a), Genus Aranema, Suba (B)
lyxa), genus Eriocaulon, genus Potamogeton.

The active substance combinations according to the invention can be used in particular for the following paddy weeds, for example: Botanical name Latin name Dicotyledon Rottara indica Koehne Rotana indica Koehne Azena Lindernia Procumbens Philcox Ludwigia prostrata Roxburg h Kuroguwai Ohwi Cyperus difformis L. Cyperus serotinus Rottboel Urikawa Sagittaria pygmaea Miq Hera modaka Alisma canaliculatum A. Br. Et B
ouche Firefly Scirpus juncoides Roxburgh However, the use of the herbicidal composition of the present invention is not limited to these weeds and can be similarly applied to other weeds.

The herbicidal composition of the present invention can be made into a usual formulation form. And as such a form, a liquid preparation, an emulsion, a wettable powder, a suspension, a powder, a soluble powder, a granule, a suspension emulsion concentrate, and a microcapsule in a polymer substance can be mentioned. These formulations can be manufactured by a known method. Such a process comprises, for example, applying the active compound to a spreading agent, ie a liquid diluent and / or a solid diluent, if necessary a surfactant, ie an emulsifier and / or dispersant and / or a foam former. By mixing with.

If water is used as the extender, organic solvents, for example, can also be used as auxiliary solvents. Examples of the liquid diluent include aromatic hydrocarbons (eg, xylene, toluene or alkylnaphthalene), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, methylene chloride, etc.) ), Aliphatic hydrocarbons [eg, cyclohexane or paraffins (eg, mineral oil fractions, minerals and vegetable oils)], alcohols (eg, butanol, glycol and ethers and esters thereof), ketones (eg, Mention may also be made of acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents such as dimethylformamide and dimethylsulfoxide and water.

As solid diluents, ammonium salts and soil natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.) and soil synthetic minerals (for example, highly dispersed silicic acid, alumina, Silicate etc.) can be mentioned. Solid carriers for granules include crushed and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles of organic materials (eg, , Sawdust, coconut coconut, corn cob and tobacco stem). Examples of emulsifiers and / or foaming agents include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (eg, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates). , Aryl sulfonates, etc.)], and albumin hydrolysis products.

Suitable dispersants are, for example, lignin sulfite waste liquors and methylcellulose. Adhesives can also be used in formulations (powder, granules, emulsions),
Such fixing agents include carboxymethyl cellulose and natural and synthetic polymers (eg gum arabic, polyvinyl alcohol and polyvinyl acetates) and natural phospholipids (eg cephalins and lecithins) and synthetic phospholipids. You can Furthermore, mineral and vegetable oils can be used as additives. Colorants can also be used, such as inorganic pigments (for example iron oxide, titanium oxide and Prussian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and ,iron,
Mention may be made of trace elements such as salts of manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally comprise between 0.1 and 95% by weight of active compound mixture, preferably between 0.5 and 90%.

The active compound mixtures according to the invention can be used as such or in the form of their preparations for controlling weeds, they can also be in the form of preparations or tank mixtures, and still other known active compounds. , Active compounds commonly used in paddy fields, such as fungicides, insecticides,
It is also possible as a mixture with plant growth regulators, plant nutrients, soil conditioners, safeners and other herbicides. As a good example thereof, the herbicidal composition of the present invention contains 1- (α, α-dimethylbenzyl) -3-p as a phytotoxic agent per 1 part by weight of the herbicidal sulfonamide in the composition.
1 to 200 parts by weight of tolyl urea, preferably 2
~ 100 parts by weight can be added.

The active compound mixture is used as it is, or in the form of a preparation thereof, or an application form prepared by further diluting the preparation, for example, a preparation liquid for spraying (ready-t).
It can be used in the form of o-use solution), emulsion, suspension, powder, wettable powder and granule. These forms can be prepared by a conventional method, for example, liquid spray (w
atering), spraying (atom)
It can be used for izing), dusting or granulation.

The herbicidal composition according to the present invention can be applied before or after germination of plants. The amount of the composition applied can vary within a substantial range. The amount applied is 0.1 to 3.5 kg / ha, preferably 0.2 to 3.0 kg / ha, as the amount of active ingredient. Although individual active substances have weaknesses in herbicidal action, the compositions show a very broad herbicidal spectrum that is effective against various weeds, far beyond the mere effects of action. The excellent effects of the herbicidal composition according to the present invention can be mentioned in the following examples. However, the present invention should not be limited to this.

[0021]

【Example】

Biological tests and formulation examples: -Active compounds Herbicidal oxyacetamides of the formula (I) I. 1: 4,5-Dichlorothiazol-2-yloxy-N-methylacetanilide I. 2: 6-Chlorobenzoxazol-2-yloxy-N-methylaceto (2-methylanilide) I. 3: 6-chlorobenzoxazol-2-yloxy-N-methylaceto (3-methylanilide) I. 4: 5-chloro-4-cyanothiazol-2-yloxy-N-methylacetanilide I. 5: 6-chlorobenzoxazol-2-yloxy-N-isopropylaceto (3-methylanilide) I.V. 6: 7-chlorobenzothiazol-2-yloxy-N-methylacetanilide A: methyl 2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonylmethyl] benzoate B: ethyl 5- [3- ( 4,6-Dimethoxypyrimidin-2-yl) ureidosulfonyl] -1-methylpyrazole-4-carboxylate C: 4- (2,4-dichlorobenzoyl) -1,3-
Dimethyl-5-pyrazolyl-p-toluenesulfonate D: 2- (β-naphthyloxy) propionanilide E: 2-Ethylamino-4- (1,2-dimethylpropylamino) -6-methylthio-1,3,5 -Triazine F: Sp-chlorobenzyl diethyl thiocarbamate

Test Example 1 Test of herbicidal effect against weeds in paddy method Method: A pot (25 × 20 × 9 cm) of 1/2000 are filled with paddy soil, and rice seedlings of 2.5 leaf stage (plant height: 15 cm) (variety: (Nihonbare), 3 plants per plant per pot were transplanted at 2 sites. Then, it was inoculated with Tainubie, Pleurotus cornucopia, Konagi, broad-leaved weeds (Azena, Kishigusa, Mizohakobe, Himezohagi, Abu Nome, etc.), various firefly seedlings, tubers of Urikawa, and small pieces of pine nuts, and watered for about 2 to 3 cm. Seven days after the transplantation of paddy rice, the active compound mixture in the form of granules prepared according to Preparation Example 1 below and the active compound were surface-treated. After the treatment, the inundated state of 3 cm was maintained, and 3 weeks after the treatment with the chemical, the herbicidal effect and the degree of chemical damage were evaluated in%. 100%: Complete death 0%: No effect or chemical damage The results are shown in Table 1.

[0023]

[Table 1]

[0024]

[Table 2]

[0025]

[Table 3]

[0026]

[Table 4]

Test Example 2 Test Method for Herbicidal Effect and Residual Effectiveness Against Taenia muscaria Similar to Test Example 1, rice seedlings were cultivated, seeds of Taenia japonicus were inoculated, and water was flooded for about 2 to 3 cm. Tainubie 2.5〜
The active compound mixture and active compound prepared according to Formulation Example 1 below at 3.0 leaf stage were surface-treated on the water surface, and the herbicidal effect was evaluated in% after 3 weeks from the drug treatment in the same manner as in Test Example 1 and the residual effect was obtained. The sex was evaluated by the germination suppression period (days) of the sea urchin. The results are shown in Table 2.

[0028]

[Table 5]

Formulation Example 1 Active Compound I. 1 part by weight of 1 and 0.25 of active compound A
To a mixture of 30 parts by weight, bentonite of 30 parts, talc of 66.75 parts by weight, and lignin sulfonate of 2 parts by weight, water is added and kneaded well, and then granulated and dried to obtain granules. Formulation Example 2 The crushed mineral particles having a particle size distribution of 0.2 to 2 mm were dissolved in an organic solvent, and the active compound I. 1 part by weight of 2 and 4 parts by weight of surfactant are sprayed on, and then the active compound N'-
(4,6-dimethoxypyrimidin-2-yl) -N "-
(4-Methylphenylsulfonylamino) -N "-(4
Granules are obtained by uniformly adhering 0.1 part by weight of -ethoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -guanidine and 5 parts by weight of powdered ground powder of white carbon.

Claims (11)

[Claims] 1. The formula: In the formula, R ¹ represents a halogen atom or cyano, R ² represents a halogen atom, R ¹ and R ² together may be benzo-fused with a ring to which they are bonded, Is optionally substituted with a halogen atom, R ³ represents a C _1-4 alkyl group, X represents O or S, Y represents a C _1-4 alkyl group, and n represents 0. Or a herbicidal oxyacetamide represented by 1 and herbicidal sulfonamides, herbicidal pyrazoles, herbicidal propionanilides, herbicidal triazines, herbicidal carbamates, herbicidal diphenyl ethers, and herbicides A herbicidal composition comprising at least one selected from the group consisting of acid amides as an active ingredient. 2. In the formula (I), R ¹ represents chloro or cyano, R ² represents chloro, and R ¹ and R ² together form a ring to which they are bonded and chloro. Substituted benzocondensation is also possible, wherein R ³ represents methyl or isopropyl, X represents O or S, Y represents methyl, and n represents 0 or 1, and herbicidal oxyacetamide. The herbicidal composition according to claim 1, wherein the herbicide composition contains a class as an active ingredient. 3. The herbicidal oxyacetamides are as follows: 4,
5-dichlorothiazol-2-yloxy-N-methylacetanilide, 6-chlorobenzoxazole-2-
Yloxy-N-methylaceto (2-methylanilide), 6-chlorobenzoxazol-2-yloxy-N-methylaceto (3-methylanilide), 5-chloro-4-cyanothiazol-2-yloxy-N-methylacetanilide, 6-chlorobenzoxazole-2
The herbicidal composition according to claim 1, which is one selected from the group consisting of -yloxy-N-isopropylaceto (3-methylanilide) and 7-chlorobenzothiazol-2-yloxy-N-methylacetanilide. 4. Herbicidal sulfonamides are the following; N-2-
Biphenylylsulfonyl N '-(4,6-dimethoxy-
1,3,5-triazin-2-yl) urea, ethyl
5- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -1-methylpyrazole-4
-Carboxylate, methyl 2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonylmethyl] benzoate, 3- (4,6-dimethoxy-1,
3,5-triazin-2-yl) -1- [2- (2-methoxyethoxy) -phenylsulfonyl] urea, N-
(2-chloroimidazole [1,2-a] pyridine-3
-Yl-sulfonyl) -N '-(4,6-dimethoxy-
2-pyrimidyl) urea, or N '-(4,6-dimethoxypyrimidin-2-yl) -N "-(4-methylphenylsulfonylamino) -N""-(4-ethoxycarbonyl-1-methylpyrazole The herbicidal composition according to claim 1, which is -5-yl-sulfonyl) -guanidine. 5. The herbicidal pyrazoles are the following: 4- (2,4
-Dichlorobenzoyl) -1,3-dimethylpyrazol-5-yl p-toluenesulfonate, 2- [4-
(2,4-Dichlorobenzoyl) -1,3-dimethylpyrazol-5-yl] acetophenone, or 2- [4-
The herbicidal composition according to claim 1, which is (2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4-methylacetophenone. 6. The herbicidal propionanilides are as follows: 2-
(Β-naphthyloxy) propionanilide, or (R
The herbicidal composition according to claim 1, which is S) -2- (2,4-dichloro-m-tolyloxy) propionanilide. 7. The herbicidal triazines are as follows; 2,4-bis (ethylamino) -6- (methylamino) -1,3,5
-Triazine, or 2-ethylamino-4- (1,2-
Dimethylpropylamino) -6-methylthio-1,3,3
The herbicidal composition according to claim 1, which is 5-triazine. 8. Herbicidal carbamates are as follows; S-p-chlorobenzyl diethylthiocarbamate, S-1-methyl-1-phenylethylpiperidine-1-carbothioate, or S-benzyl 1,2-dimethylpropyl. The herbicidal composition according to claim 1, which is (ethyl) thiocarbamate. 9. The herbicidal diphenyl ethers are the following: 2,
The herbicidal composition according to claim 1, which is 4,6-trichlorophenyl-4'-nitrophenyl ether or 2,4-dichlorophenyl-3'-methoxy-4'-nitrophenyl ether. 10. The herbicidal composition according to claim 1, wherein the herbicidal acid amide is (RS) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutyramide. 11. 0.01 to 2 parts by weight of herbicidal sulfoneanilides per 1 part by weight of herbicidal oxyacetamides,
Herbicidal pyrazoles 2.5 to 35 parts by weight, herbicidal propionanilides 0.6 to 50 parts by weight, herbicidal triazines 0.06 to 10 parts by weight, herbicidal carbamates 3 to 1
The herbicidal composition according to claim 1, which has a composition ratio of 5 parts by weight, 5 to 35 parts by weight of the herbicidal diphenyl ethers, and 3.5 to 25 parts by weight of the herbicidal acid amides.