KR970007084B1 - Herbicides for weed control in rice - Google Patents

Abstract

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Description

Herbicides for weed control of rice

The present invention relates to a method for controlling weeds in rice cultivation by applying an effective amount of a novel composition comprising a mixture of two herbicides, and a herbicide comprising only the mixture itself or a composition comprising the mixture itself. will be.

There is always a need for new compounds that are effective in controlling the growth of weeds. In the most common state, these chemicals have been studied to selectively control weed growth in useful grains such as cotton, rice, corn, wheat and soybeans. The uncontrolled weed growth of such grains can cause significant losses that reduce farmers' profits and raise costs for consumers. Especially in the cultivation of rice, there has been a demand to find a compound that selectively controls the growth of weeds. According to rice's availability

"Sulfonylurea" herbicides are a class of highly effective herbicides discovered in recent years. Although there are many structural modifications in this class of herbicides, this class of herbicides typically consists of a sulfonylurea bridge-SO ₂ NHCONH- linking two aromatic or heteroaromatic rings.

US Pat. No. 4,394,506 describes compounds within the scope of formula (I) according to the present invention.

U.S. Patent No. 4,383,113 also describes compounds within the scope of formula (I) according to the present invention.

US Pat. No. 4,645,527 discloses the use of certain sulfonamides to protect cereal grains from damage by compounds within the scope of formula (I) according to the invention, wherein X is CH ₃ , Y is OCH ₃ and Z is N. It is described.

However, none of the patent documents describes the use of the compound for controlling weeds in rice.

(Summary of invention)

The present invention provides a mixture of a compound of the general formula (I) with a compound selected from 2, 4-dichlorophenoxyacetic acid, bensulfuron methyl, thiobencarb, dimepiperate, esprocarb, dimelone and propanyl. It relates to a composition comprising.

…(Ⅰ)

… (Ⅰ)

Wherein X is CH ₃ or OCH ₃ , Y is OCH ₃ , Z is N or CH, provided that when Z is CH, X is OCH ₃ and when Z is N, X is CH ₃ .

Preferred mixtures of the present invention are mixtures of a compound of formula (I) with bensulfur methyl, wherein Z is N, X is CH ₃ and Y is OCH ₃ .

In addition, the present invention is a method for controlling weed growth in rice by applying the effective amount of the compound of the general formula (I) to the rice alone or by mixing it with other herbicides after rice transplanting or rice germination It is about.

For reasons of more effective weed control or better grain resistance, the preferred method of the present invention is:

1. A method of controlling weed growth in rice by applying an effective amount of a compound of the general formula (I) in which Z is N, X is CH ₃ and Y is OCH ₃ after rice transplanting or germination;

2. A method of controlling weed growth in rice by applying an effective amount of a compound of formula (I) in which Z is CH and X and Y are OCH ₃ after rice transplanting or germination, respectively;

3. Process of using the compound of the general formula (I) mentioned in the above paragraph 1 as a mixture with an herbicidally effective amount of 2,4-dichlorophenoxyacetic acid;

4. A process using the compound of formula (I) as mentioned in paragraph 1 above as a mixture with a herbicidally effective amount of bensulfuron methyl;

5. A mixture of S-[(4-chlorophenyl) methyl] diethylcarbamothioate (thiobencarb) with the general formula (I)

6. Process of using the compound of the general formula (I) mentioned in the above paragraph 1 as a mixture with S-1-methyl-1-phenylethylpiperidine-1-carbothioate (dimepiperate);

7. Process of using the compound of general formula (I) mentioned in the above paragraph 1 as a mixture with S-benzyl-N-ethyl-N- (1,2-dimethyl) propylthiol carbamate (esprocarb);

8. Process of using the compound of the general formula (I) mentioned in the above paragraph 1 as a mixture with 1- (α, α-dimethylbenzyl) -3-p-tolylurea (daimone); And

9. A process using a compound of formula (I) wherein Z is N and X is CH ₃ as a mixture with benzylfuron methyl.

Weeds in rice, especially broadleaf weeds, can be controlled by applying an effective amount of the compound of the general formula (I) to rice after seeding or germination.

Compounds of the general formula (I) may be used for other rice herbicides [eg, 2,4-dichlorophenoxy acetic acid, bensulfuron methyl, S-[(4-chlorophenyl) methyl] diethylcarbamothioate, S-1- Methyl-1-phenylethylpiperidine-1-carbothioate, S-benzyl-N-ethyl-N- (1,2-dimethyl) propylterol carbamate or 1- (α, α-dimethylbenzyl)- 3-p-tolylurea] can be used to expand the range of weed control.

(Detailed Description of the Invention)

Compounds of formula (I) are known in the art. Their chemical names are: methyl 2-[[[[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] benzoate (X is CH ₃ , Y is OCH ₃ , Z is N), and methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoate (X is OCH ₃ , Y is OCH ₃ and Z is CH).

In addition, methyl 2-[[[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] benzoate is metsulfuron methyl It is known by the generic name.

Compounds of formula (I) wherein X is OCH ₃ , Y is OCH ₃ and Z is CH and compounds of formula (I) wherein X is CH ₃ and Y is OCH ₃ and Z is N are described in U.S. Patent Nos. 4,394,506 And Examples 1, 3 to 6, 12, and 13 of US Pat. No. 4,383,113.

As discussed in the section "Solubility", the compounds of the invention may be combined with 2, 4-dichlorophenoxyacetic acid (2, 4-D), agriculturally suitable esters or salts thereof, or with bensulfuron methyl When combined with thiobencarb, with dimepiperate, with esprocarb, or with dimeron, it is particularly effective for controlling broadleaf weeds and sedges. 2, 4-D, esters thereof and salts thereof are well known in the field of weed control. More frequently used, some of its esters are prepared from 2-propanol, n-butanol, 2-butoxy ethanol and 6-methyl-1-heptanol. More frequently used, some of its salts are sodium, dietanolamine, diethylamine, dimethylamine, ethanolamine, methylamine and triethanolamine. It is not intended to be limited to the esters or salts described above.

)라는 상품명으로 판매되고 있다. 이것은 미합중국 특허 제4,420,325호에 상세히 기재되어 있으며, 이 특허에 기술된 일반적인 방법으로 제조할 수 있다.The full chemical name of bensulfuron methyl is methyl 2-[[[[[(4, 6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] methyl] benzoate. This was done by E.I. du Pont de Nemours & Co. to help control weeds in rice.

It is sold under the brand name. This is described in detail in US Pat. No. 4,420,325, which may be prepared by the general method described in this patent.

(Formulation)

Useful body forms of the compound of formula (I) can be prepared by conventional methods. These include powders, granules, pellets, solutions, suspensions, emulsions, wetting powders, emulsifying thickeners and the like. Many of these can also be applied directly. Sprayable formulations can be extended in a suitable medium and can be used in spray volumes from several liters to several hundred liters per ha. High concentration compositions are first used as intermediates for further formulation. The body shape can vary widely from about 1 to 99% by weight of the active ingredient (s), and (a) from about 0.1 to 20% by weight of the surfactant (s) and (b) from about 5 to 99% by weight of a solid or liquid At least one of the diluent (s). More particularly, the formulation may contain these ingredients in the following approximate proportions.

The active ingredient at low or high concentrations may, of course, be present depending on the intended use and the physical properties of the compound. A higher ratio of surfactant to active ingredient is sometimes preferred, which is achieved by incorporation into the body shape or by tank mixing.

Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents & Carriers", 2nd Ed., Dorland Books, Caldwell, NJ, but other solids mined or prepared may also be used. Higher absorbent diluents are preferred for wettable powders, and higher density diluents are preferred for powders. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, NY (1985). Less than 0.1% for "McCutcheon's Detergents & Emulsifiers Annual", MC Publishing Corp., Ridgewood, NJ; And Sisely & Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., NY (1964), describe surfactants and recommended uses. All formulations contain small amounts of additives, which can reduce foaming, caking, corrosion, microbial growth and the like.

Methods of preparing such compositions are well known. Liquid formulations are prepared by simply mixing the components. Fine solid compositions are prepared by blending and grinding, usually as in a hammer or fluid energy grinder. Suspensions are prepared by wet milling (see, eg, US Pat. No. 3,060,084 to Littleler). Granules and pellets can be prepared by spraying the actives on pre-formed granular carriers or by flocculation techniques (see, eg, US Pat. No. 3,060,084 to Littleler). Granules and pellets can be prepared by spraying the actives on preformed granular carriers or by agglomeration techniques. J. E. Browning, "Agglomeration", Chemical Engineering, pp. 147ff. (Dec. 4, 1967); And "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, NY, pp. 8-57ff. (1973).

For further information in the field of formulation, see, for example, US Pat. No. 3,235,361 (1966. 2.15) to H.M.Loux in column 6, lines 16 to 7, line 19, and Examples 10-41; US Patent No. 3,309,192 to RW Luckenbaugh (March 14, 1967), Line 5, Lines 43 to 7, Line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; US Pat. No. 2,891,855 (June 23, June 23, 1959) by J. Gysin & E. Knusli, column 3, lines 66 to 5, line 17, and Examples 1-4; See G.C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., NY, pp. 81-96 (1961); And in J.D. Fryer & S.A. Evans, "Weed Conterol Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, pp. 101-103 (1968).

(Related patent application)

The present invention is a partial serial application of US Patent Application No. 082,697 filed August 7, 1987, and a partial continuous application of US Patent Application No. 157,548 filed February 12, 1988, May 1988 Partial serial application of US Patent Application No. 194,549, filed 16.

Wettable powder

2.4-dichlorophenoxyacetic acid, sodium salt 60%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] canobil] amino] sulfonyl]

Benzoate 1%

Dodecylphenol Polyethylene Glycol Ether 2%

Sodium Lignin Sulfonate 4%

Sodium Silicoaluminate 6%

Sodium carbonate 2%

Montmorillonite (calcined) 25%

Blend the ingredients completely. Participation is by spraying a liquid surfactant onto the solid component in the blender. Grinding in a hammer mill essentially produces all particles up to 100 microns, then blends the material again and U.S.S. Filter and package through # 50 sheave (diameter: 0.3㎜).

(Example 2)

Wettable powder

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino]

Benzoate 40%

Dioctyl Sodium Sulfosuccinate 1.5%

Sodium Lignin Sulfonate 3%

Low Viscosity Methyl Cellulose 1.5%

Ether pearlite 54%

The ingredients are thoroughly blended and passed through an air mill to produce an average particle size of less than 15 microns, blended again, filtered through a U.S.S # 50 sheave (caliber: 0.3 mm) and packaged.

(Example 3)

Granulation

25% wettable powders of Example 2

Gypsum 64%

Potassium Sulfate 11%

The components are blended in a rotary mixer and granulated by water spray. When most of the materials have reached the desired range of 1.0 to 0.42 mm (U.S.S. # 18 to 40 sheaves), the granules are transferred to dry and screened.

The larger material is crushed to produce additional material in the desired range. These granules contain 10% of the active ingredient.

(Example 4)

Oil suspension

Methyl 2-[[[[(4-methoxy-6-methyl-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoate 25%

5% polyoxyethylene sorbitol hexaoleate

70% high aliphatic hydrocarbon oil

The components are ground together in a sand mill until the solid particles are smaller than about 5 microns. The resulting thick suspending agent may also be applied directly, but it is preferred to apply it by weight with oil or after emulsification in water.

(Example 5)

Aqueous suspensions

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 25%

Hydration attapulgite 3%

Coarse Calcium Lignin Sulfonate 10%

Sodium Dihydrogen Phosphate 0.5%

61.5% of water

The components are ground together in a ball mill or roller mill until the solid particles are reduced to a diameter of less than 10 microns.

(Example 6)

Wettable powder

Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl) -amino] carbonyl] amino] sulfonyl] benzoenite 95%

Dioctyl Sodium Sulfosuccinate 0.5%

Sodium Lignin Sulfonate 1.5%

Synthetic Microsilica 3.0%

Particles are prepared by blending the components and grinding in a hammer mill, with almost all particles less than 100 microns in size. The material is filtered through a U.S.S # 50 (diameter: 0.3 mm) screen and packaged.

(Example 7)

Granulation

8% wettable powder of Example 6

2% wettable powder of Example 2

Aterpulgite granulation (U.S.S. # 20 to 40 mesh) 90%

The wet powder slurry is sprayed onto the granulation surface and mixed in the blender. After the slurry is added, the granules are removed from the blender and dried and packaged.

(Example 8)

Oil suspension

2.4-dichlorophenoxyacetic acid, butoxyethyl ester 24.6%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 0.4%

5% polyoxyethylene sorbitol hexaoleate

Higher aliphatic hydrocarbon oil 70%

The components are ground together in a sand mill until the solid particles are reduced to less than about 5 microns. The resulting thick suspending agent may also be applied directly, but it is preferred to extend it with oil or apply it after emulsification in water.

(Example 9)

Extruded pellets

Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoate 25%

Anhydrous sodium sulfate 10%

Coarse Calcium Lignin Sulfonate 5%

Sodium Alkalnaphthalenesulfonate 1%

Calcium / Magnesium Bentonite 59%

The components are blended, ground in a hammer mill and then humidified with about 12% water. The mixture is extruded and cut into cylinders (diameter: about 3 mm) to produce pellets (length: about 3 mm). These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S # 20 sheave (diameter: 0.84 mm). U.S.S. The granules remaining on the # 40 sheave (caliber: 0.42 mm) are packaged for use and the fine material is recycled.

(Example 10)

Granulation

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbonyl] amino] sulfonyl]

Benzoate 10%

Methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] methyl]

Benzoate 50%

Wetting Agent 1%

Dispersant 2%

Crude ligninsulfonate salt (containing 5 to 20% natural sugars) 10%

Aterpulzite Clay 27%

The ingredients are blended and ground and passed through a 100 mesh screen. This material is then added to a fluid bed granulator, airflow is added to slowly fluidize the material, and then finely sprayed water is sprayed onto the fluidized material. Fluidization and spraying continue until granules are produced in the desired range of sizes. Spraying stops, but fluidization continues, optionally using heat, until the water content drops to the desired amount, usually less than 1%. Subsequently, the material is released and screened for the desired size range, typically 14 to 100 mesh (1410 to 149μ), then packaged for use.

(Example 11)

Wettable powder

Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)] amino] carbonyl] amino] sulfonyl] benzoate 80%

Sodium Alkyl Naphthalene Sulfonate 2%

Sodium Lignin Sulfonate 2%

Amorphous synthetic silica 3%

Kaolinite 13%

The components are blended and then polished in a hammer mill to produce particles with an average particle size of less than 25 μm in diameter. The material is blended again and U.S.S. Filter through # 50 sheave (diameter: 0.3㎜) and package.

(Example 12)

Wettable powder

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 4%

Methyl 2-[[[[(4,6-dimethoxy-6-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] methyl]

Benzoate 36%

Dioctyl Sodium Sulfosuccinate 1.5%

Sodium Lignin Sulfonate 3%

Low Viscosity Methyl Cellulose 1.5%

Attapulgite 54%

The ingredients are thoroughly blended and passed through an air mill to produce an average particle size of less than 15 microns, blended again, filtered through a U.S.S # 50 sieve (caliber: 0.3 mm) and packaged.

All compounds of the invention can be formulated in the same manner.

(Example 13)

Extruded pellets

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 1%

Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] methyl]

Benzoate 24%

Anhydrous sodium sulfate 10%

Coarse Calcium Lignin Sulfonate 5%

Sodium Alkyl Naphthalene Sulfonate 1%

Calcium / Magnesium Bentonite 59%

The ingredients are blended and ground in a hammer mill and then humidified with about 12% water. The mixture is extruded and cut into cylinders (diameter: about 3 mm) to produce pellets (length: about 3 mm). These may be used directly after drying, or the pellet may be crushed to pass the U.S.S # 20 sheave (diameter: 0.84 mm). The granules remaining on the U.S.S # 40 sheave (diameter: 0.42 mm) can be packaged for use and the fine material is recycled.

(Example 14)

Wettable powder

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 65%

Dodecylphenol Polyethylene Glycol Ether 2%

Sodium Lignin Sulfonate 4%

Sodium Silicoaluminate 6%

Montmorillonite 23%

Blend the ingredients completely. Liquid surfactants are added by spraying on the solid component in the blender. After grinding in a hammer mill to substantially produce all particles up to 100μ, the materials are blended again and filtered and packaged through a U.S.S # 50 sheave (caliber: 0.3 mm).

(Example 15)

Wettable powder

2,4-dichlorophenoxyacetic acid, sodium salt 49.5%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 0.5%

Sodium Alkyl Naphthalene Sulfonate 2%

Low Viscosity Methyl Cellulose 2%

Diatomaceous Earth 46%

The components are blended and coarsely ground in a hammer mill and then air milled to produce substantially all of the active particles with a diameter of 10 microns or less. The product is blended again and packaged.

(Example 16)

Wettable powder

S-[(4-chlorophenyl) methyl] diethylcarbamothioate 60%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl] amino] carbonyl] amino] sulfonyl

Benzoate 1%

Dodecylphenol Polyethylene Glycol Ether 2%

Sodium Lignin Sulfonate 4%

Sodium Silicoaluminate 6%

Sodium carbonate 2%

Montmorillonite (calcined) 25%

Blend the ingredients completely. Liquid surfactants are added by spraying on the solid components in the blender. After grinding in a hammer mill, substantially all of the particles were produced to 100 μm or less, and then the material was blended again and U.S.S. Filter and package through # 50 sheave (diameter: 0.3mm).

(Example 17)

Wettable powder

S-1-methyl-1-phenylethylpiperidine-1-carbothioate 60%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] canobil] amino] sulfonyl]

Benzoate 1%

Dodecylphenol Polyethylene Glycol Ether 2%

Sodium Lignin Sulfonate 4%

Sodium Silicoaluminate 6%

Sodium carbonate 2%

Montmorillonite (calcined) 25%

Blend the ingredients completely. Liquid surfactants are added by spraying on the solid component in the blender. After grinding with a hammer grinder, substantially all of the particles were produced to 100 µm or less, and then the material was blended again and U.S.S. Filter and package through # 50 sheave (diameter: 0.3mm).

(Example 18)

Wettable powder

S-benzyl-N-ethyl-N- (1,2-dimethyl) propylthiol carbamate 60%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 1%

Dodecylphenol Polyethylene Glycol Ether 2%

Sodium Lignin Sulfonate 4%

Sodium Silicoaluminate 6%

Sodium carbonate 2%

Montmorillonite (calcined) 25%

Blend the ingredients completely. Liquid surfactants are added by spraying on the solid components in the blender. After grinding in a hammer mill to substantially produce all particles up to 100 microns, the material is blended again and filtered and packaged through a U.S.S # 50 sheave (caliber: 0.3 mm).

(Example 19)

Wettable powder

1- (α, α-dimethyl benzyl) -3-3-p-tolylurea 60%

Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl]

Benzoate 1%

Dodecylphenol Polyethylene Glycol Ether 2%

Sodium Lignin Sulfonate 4%

Sodium Silicoaluminate 6%

Sodium carbonate 2%

Montmorillonite (calcined) 25%

Blend the ingredients completely. Liquid surfactants are added by spraying on the solid component in the blender. After grinding in a hammer mill to substantially produce all particles up to 100 microns, the material is blended again and filtered and packaged through a U.S.S # 50 sheave (caliber: 0.3 mm).

(Usefulness)

The compounds of the present invention are useful for weed control of rice and can be used in both cases of rice transplanted or directly sown. This compound can be applied to grain after germination and from 7 days after transplanting or germination until the end of rice harvest and until weeds no longer need to be chemically controlled. This compound can be applied as a foliar spray sufficient to evenly distribute the treatment. Additives may be included in the spray to aid penetration of the treatment agent.

Chemicals are particularly effective at controlling broadleaf weeds and can be combined with other rice herbicides to broaden the range of weed control. The chemical is particularly effective against broadleaf weeds and weeds when combined with 2,4-dichlorophenoxyacetic acid (2, 4-D), its agriculturally suitable esters or salts, or when combined with bensulfuron methyl.

Particularly useful combinations with 2, 4-D include a ratio of the present compound to 2, 4-D in the range from 4: 125 to 1: 625. Particularly useful, combinations with bensulfron methyl have a ratio of 1: 2 to 1:50 of the compound relative to bensulfron methyl. The compounds of the present invention also contain thiovancarb, esprocarb, dimelone, dimepiperate, butachlor, molinate, ethyl 5-[[[[(4, 6-dimethoxy-2-pyrimidinyl) amino ] Carbonyl] amino] sulfonyl] -1-methyl-1H-pyrazole-4-carboxylate, naproanilide, betazone, synmethylene, chlormethoxyl, quinclolac, pretalaclo

The application amount of the compound of the present invention can be varied from 0.5 to 10 g / ha (preferably 1 to 5 g / ha) depending on the weeds to be controlled, the growth stages of grains and weeds, the types of grains, and the environmental conditions of the application time have. One of ordinary skill in the art can select the amount to use for each situation.

The following examples clearly demonstrate the utility of the compounds of the invention both alone and as mixtures.

(Example)

Methyl 2-[[[[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] benzoate (Compound 1), and others Its mixtures with the compounds are applied by spraying (using hand sprayers) to the rice (planted or directly sown) in several rice growing regions in Southeast Asia and the United States. Tables 1 to 26 show these test results and clearly illustrate the usefulness of the present invention. A detailed description of each application is included in the table.

Compound 1

Compound 2

TABLE 1 Herbicidal efficacy of compound 1 in Thailand

1. 100 means complete control, 0 means no control.

2. Application amount of active ingredient (g / ha) (GAI: grams active ingredient)

3. Treatments applied 36 days after sowing.

4. WAA = weeks after application (evaluation).

5. Abbreviation: SZ = Sphenoclea zeylanica.

CY = Cyperus species.

Table 2 Effect of Compound 1 on the basis of the average of three results on rice growth in Thailand

1. Application amount of active ingredient (g / ha).

2. Phytotoxicity rating is 0 = No effect.

3 = Not acceptable.

10 = 100% plant death.

3. DAS = number of days after planting (time of application).

TABLE 3 Herbicidal efficacy of the combination of Compounds 1, 2, and 4-D based on the average of three results in Thailand

1. Application amount of active ingredient (g / ha).

2.% Control Rate evaluated after 6 weeks of application.

3. DAS = number of days after planting (time of application).

TABLE 4 Effect of Compound 1 on Rice Growth Based on Tax Results in Thailand

1. Application amount of active ingredient (g / ha).

2. Phytotoxicity rating is 0 = No effect.

3 = not allowed.

10 = 100% plant death.

3. DAS = number of days after planting (time of application).

Table 5 Herbicidal efficacy of compound 1 on application time in Indonesia

1. Plot drained before application and submerged after 3 days.

2. Application amount of active ingredient (g / ha).

3. Abbreviation: MV = Monochoria vaginalis.

CI = Cyperus iria.

PS = Pistia stratioides.

4. Number of weeks after application (evaluation).

5. WAT = weeks after migration (application).

TABLE 6 Herbicidal efficacy of compound 1 in Indonesia

1. Apply 2 weeks after transplanting.

Plots are drained before application and submerged again 3 days after application.

2. Application amount of active ingredient (g / ha).

3. Abbreviation: SM = Salvinia molesta.

MV = Monochoria vaginalis.

SJ = Scirpus juncoides.

EC = Echinochloa crus-galli.

4. Number of weeks after application (evaluation).

5. 2, 4-D amine salt.

[Table 7] Effect of herbicide treatment on grain resistance of rice transplanted

1. Grain Tolerance Rating: 0 = No impact; 10 = complete kill.

2. Application amount of active ingredient (g / ha).

3. WAA = number of weeks after application (evaluation).

4. 2, 4-D amine salt.

TABLE 8 Herbicidal efficacy of the combination of Compounds 1, 2 and 4-D in Malaysia

1: Application 30 days after sowing.

Evaluation 22 days after treatment.

2. Application amount of active ingredient (g / ha).

3. Abbreviation: SG = Scirpus grossus.

MV = Monochoria vaginalis.

SZ = Sphenoclea zeylanica.

CD = Cyperus difformis.

FM = Fimbristylis miliacea.

MC = Marsilea crenata.

4. 2, 4-D is a dimethylamine salt.

TABLE 9 Wideleaf Weed Control Using Late Subsequent Application of Compound 1 in Beaumont, Texas

1.Compound applied with 0.25% AG-98 wetting agent 1.

2. The application amount is expressed in g of active ingredient per ha (g / ha).

3. 30 days after sowing (24 days after germination) until the soil is wet; Immerse in 24 days after germination (6 days after application); It is evaluated 70 days after sowing.

4. Abbreviation: EC = Echinochloa colonum.

SE = Sesbania exaltata.

AI = Aeschynomene indica.

CC = Caperonia castaniifolia.

COM = Commelina communis.

EA = Eclipta alba.

SEDGE = 1 year old four seconds (?).

Table 10 Test results in fields of compound 1 + bensulfuron methyl for weed control of rice sown directly

1. The application amount is expressed in g of active ingredient per ha (g / ha).

2. 10 is complete control, 0 is not controlled, WAA is the number of weeks after application (evaluation).

3. SZ = Sphenoclea zeylanica.

4. CI = Cyperus iria.

5. MC = Marsilea crenata.

Table 11 Test results of compound 1 + bensulfuron methyl applied to 7DAS ¹ for weed control of directly sown rice

1. DAS = number of days after sowing.

2. The application amount is expressed in g of active ingredient per ha (g / ha).

3. Phytotoxicity is rated as follows:

0 = no impact. 3 = Not acceptable. 10 = 100% plant death.

4. Controls are graded as follows:

0 = not controlled. 10 = complete control. WAA = weeks after application.

5. SZ = Sphenoclea zeylanica.

6. CD = Cyperus difformis.

7. Sodium salt of 2, 4-D.

Table 12 Test results of the field of compound 1 + bensulfuron methyl applied to 18DAS ¹ for weed control of directly sown rice

1. DAS = number of days after sowing.

2. The applied amount is expressed in g of the active ingredient (g / ha).

3. Phytotoxicity is rated as follows:

0 = no impact. 3 = Not acceptable. 10 = 100% plant death. WAA = weeks after application

4. Controls are graded as follows:

0 = not controlled. 10 = complete control. WAA = weeks after application.

5. SZ = Sphenoclea zeylanica.

6. CI = Cyperus iria.

7. FM = Fimbristylis miliacea.

8. JL = Jussiaea linifolia.

9. Sodium salt of 2, 4-D.

Table 13 Test results of compound 1 + bensulfron methyl applied to 25DAS ¹ for weed control of directly sown rice

1. DAS = number of days after sowing.

2. The applied amount is expressed in g of the active ingredient (g / ha).

3. Phytotoxicity is given in the following classes.

0 = no impact. 3 = Not acceptable. 10 = 100% plant death. WAA = Weeks after application.

4. Controls are graded as follows:

0 = not controlled. 10 = complete control. WAA = weeks after application.

5. SZ = Sphenoclea zeylanica.

6. CI = Cyperus iria.

7. Sodium salt of 2, 4-D.

[Table 14] 7DA averaged three times for weed control of rice sown directly in the Philippines

Test results in the field of compound 1 + bensulfuron methyl applied to S ¹

1. DAS = number of days after sowing.

2. The applied amount is expressed in g of the active ingredient (g / ha).

3. Phytotoxicity is rated as follows:

1 = no impact. 9 = 100% plant death. DAA = days after application.

4. Barnyardgrass (Echinochloa crus-galli).

TABLE 15 Effect of Compound 1 in Combination with Thiobencarb, Dimepiperate, Esprocarb and Dimelon on Rice Growth

1. Application amount of active ingredient (g / ha).

2. Visible grain injury (for untreated test) Grade: 0 to 100%

0 = no injury. 100 = 100% plant kill.

3. Plant height (for untreated test) Grade: 0 to 100%

4. Dry weight (for untreated test) Grade: 0 to 100%

5. Grain Tolerance: 5 days after diversion (variant Nihon Bear) at 2.0 to 2.2 leaf stage, the compound is applied to the transferred rice. Graded 15 days after application. The results are averaged three times.

TABLE 16 Herbicidal Efficacy of Compound 1 in the United States

1. Evaluate 57 days after application.

2. Abbreviation: EA: Eclipse alba.

SE: Sesbania exaltata.

3. Application amount of active ingredient (g / ha).

TABLE 17 Herbicidal efficacy of compounds 1 and 2, 4-D in Thailand

1. Evaluate 14 days after treatment.

2. Nickname: CD = Cyperus difformis.

LL = Ludwigia linifolia.

MV = Monochoria vaginalis.

SZ = Sphenoclea zeylanica.

3. Application amount of active ingredient (g / ha).

TABLE 18 Herbicidal Efficacy of Compound 1, Bensulfron Methyl and 2, 4-D in Thailand

1. Evaluate 13 days after treatment.

2. Abbreviated name: CD = Cyperus difformis.

LL = Ludwigia linifolia.

SZ = Sphenoclea zeylanica

3. Application amount of active ingredient (g / ha).

TABLE 19 Herbicidal Efficacy of Compound 1, Bensulfron Methyl and 2, 4-D in Thailand

1. Evaluate 13 days after treatment.

2. Abbreviated name: CD = Cyperus difformis.

LL = Ludwigia linifolia.

SZ = Sphenoclea zeylanica

3. Application amount of active ingredient (g / ha).

TABLE 20 Herbicidal Efficacy of Compound 1, Bensulfron Methyl and 2, 4-D in Thailand

1. Evaluate 13 days after treatment.

2. Abbreviated name: CI = Cyperus iria.

FM = Fimbristylis miliacea.

LL = Ludwigia linifolia.

SZ = Sphenoclea zeylanica.

3. Application amount of active ingredient (g / ha)

Table 21. The herbicidal efficacy of compounds 1 and 2, 4-D in Malaysia

1. Evaluate 42 days after treatment.

2. Abbreviated name: FM = Fimbristylis miliacea.

LA = Ludwigia adscendens.

MC = Marsilea crenata.

MV = Monochoria vaginalis.

SG = Saggittaria guayanensis.

SS = Scirpus species.

3. Application amount of active ingredient (g / ha).

TABLE 22 Effect of Compound 1 in Combination with Thiobencarb and Bensulfron Methyl on Rice Growth

1. Application amount of active ingredient (g / ha).

2. Visible grain injury (for untreated test) Grade: 0 to 100%

0 = no injury. 100 = 100% plant kill.

3. Plant height (for untreated test) Grade: 0 to 100%.

4. Dry weight (for untreated test) Grade: 0 to 100%.

5. Grain tolerance: 7 days after seeding (variant Koshihikari) in the 2.0 to 2.2 leaf stage, the compound is applied to the seeded rice. Graded 21 days after application. The results are averaged three times.

TABLE 23Effect of Compound 1 with Bensulfuron Methyl and Thiobencarb or Pretilachlor on the Growth of Rice

1. Application amount of active ingredient (g / ha).

2. Visible grain injury (for untreated test) Grade: 0 to 100%

0 = no injury. 100 = 100% plant kill.

3. Plant height (for untreated test) Grade: 0 to 100%.

4. Dry weight (for untreated test) Grade: 0 to 100%.

5. Grain tolerance: 7 days after seeding (variant Koshihikari) in the 2.0 to 2.2 leaf stage, the compound is applied to the seeded rice. Graded 21 days after application. Results are averaged three times.

TABLE 24Effect of Compound 1 in Combination with Bensulfuron Methyl and Thiobencarb or Pretilachlor on Weed Control

1. Application amount of active ingredient (g / ha).

2. Visible weed control (for untreated test)

0 = no injury. 10 = complete control.

3. EO = Echinochloa oryzicola.

4. CD = Cyperus difformis.

5. MV = Monochoria vaginalis.

6. BL = Lindernia pyxidaria.

7. SJ = Scirpus juncoides.

8. SP = Sagittaria pygmaea.

9. CS = Cyperus serotinus.

10. Treat weeds at 1.0 leaf stage and assess after 4 weeks. Results are averaged twice.

TABLE 25Effect of Compound 1 with Bensulfuron Methyl and Thiobencarb or Pretilachlor on Weed Control

1. Application amount of active ingredient (g / ha).

2. Visible weed control (for untreated test) Grade: 0 to 10.

0 = no injury. 10 = complete control.

3. EO = Echinochloa oryzicola.

4. CD = Cyperus difformis.

5. MV = Monochoria vaginalis.

6. BL = Lindernia pyxidaria.

7. SJ = Scirpus juncoides.

8. SP = Sagittaria pygmaea.

9. CS = Cyperus serotinus.

10. Treat the weeds at the 2.0 leaf stage and assess 4 weeks later. Results are averaged twice.

TABLE 26 Herbicidal efficacy and grain resistance of Compounds 1 and 2 in greenhouse tests

1. Application amount of active ingredient (g / ha).

2. Visible weed control or grain injury (for untreated test) Grade: 0 to 100%

0 = no injury. 100 = 100% plant kill

3. M101 = japonica rice variety M101.

4. LEMONT = Indica rice variety Lemont.

5. CD = Cyperus difformis.

6. AP = Alternanthera philoxeroides.

7. AT = Alisma triviale.

SR = Sagittaria rigida.

9. Transfer rice from 2.0 to 2.5 leaf stage and treat after 12 days. Grain injuries and weed control grades after 24 days of treatment.

TABLE 27 Expected ¹ and Observational Activity for Weeds of Combination of Compound 1 and Bensulfuron Methyl

1. Colby equation ² for calculating a synergistic effect (Kolby equation).

E = A + B-

E = expected value.

A = observed for compound 1.

B = observation for bensulfuron methyl.

If (observation-expected value) is a positive value, the blend is considered to have a synergistic effect.

For example :

For SZ at 4 g / ha in Table 20, A = 60

For SZ at 10 g / ha, B = 23

E = 60 + 23-

E = 69.2

The observed value of the combination of Compound 1 and Bensulfuron Methyl is 97 for spanoclea Jelanica in amounts of 4 and 10 g, respectively.

Observation-expectation

97-69.2 = + 27.8

2. Kolby, S.R., Weeds 15: 20-22, 1967.

TABLE 28 Expected and Observed Activity of Rice Combination of Compound 1 and Bensulfron Methyl

Injuries expected for rice (as calculated by the Colby's equation) are lowered by the combination of compound 1 and bensulfur methyl. This means that it is practically safe for rice grains.

Claims (12)

The following compound of formula (I) and methyl 2-[[[[[((4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] methyl] benzoate (bensulfur methyl) Herbicide composition for weed control of rice, characterized in that it comprises a mixture with.

Wherein X is CH ₃ or OCH ₃ ; Y is OCH ₃ ; Z is N or CH, provided that when Z is CH, X is OCH ₃ , and when Z is N, X is CH ₃ . The composition of claim 1 comprising a compound of formula (I) wherein Z is N together with bensulfuronmethyl. After rice transplanting or rice germination, 0.5 to 10 g / ha of the compound of the following general formula (I) is applied to rice alone or 2,4-dichlorophenoxyacetic acid, methyl 2-[[[[[(4, 6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] methyl] benzoate (bensulfuron methyl), S-[(4-chlorophenyl) methyl] diethylcarbamothioate (thio) Bencarb), S-1-methyl-1-phenylethylpiperidine-1-carbothioate (dimepiperate), S-benzyl-N-ethyl-N- (1,2-dimethyl) propylthiol carbamate Mixed with other herbicides selected from (esprocarb), 1- (α, α-dimethylbenzyl) -3-p-tolylurea (daimone) and N- (3,4-dichlorophenyl) propanamide (propanyl) To control weed growth in rice by application.

Wherein X is CH ₃ or OCH ₃ ; Y is OCH ₃ ; Z is N or CH, provided that when Z is CH, X is OCH ₃ , and when Z is N, X is CH ₃ . The method of claim 3 wherein Z is N, X is CH ₃ and Y is OCH ₃ . The method of claim 3, wherein Z is CH and X and Y are each OCH ₃ . The process according to claim 4, wherein a herbicidally effective amount of 2,4-dichlorophenoxyacetic acid is applied as a mixture with the compound of general formula (I). 5. A process according to claim 4, wherein a herbicidally effective amount of bensulfuron methyl is applied as a mixture with the compound of formula (I). 5. The method of claim 4, wherein a herbicidally effective amount of S-[(4-chlorophenyl) methyl] diethylcarbamothioate (thiobencarb) is applied as a mixture with the compound of formula (I). 5. A process according to claim 4, wherein a herbicidally effective amount of S-1-methyl-1-phenylethyl-piperidine-1-carbothioate (dimepiperate) is applied as a mixture with the compound of general formula (I). . The herbicidally effective amount of S-benzyl-N-ethyl-N- (1,2-dimethyl) propylthiol carbamate (esprocarb) is applied as a mixture with the compound of general formula (I). Way. 5. The method of claim 4, wherein a herbicidally effective amount of 1- (α, α-dimethylbenzyl) -3-p-tolylurea (dimeron) is applied as a mixture with the compound of formula (I). 5. A process according to claim 4, wherein a herbicidally effective amount of N- (3,4-dichlorophenyl) propanamide (propanyl) is applied as a mixture with the compound of general formula (I).