JPH10226605A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicidal composition, especially the one suitable for controlling weeds in corn and soybean fields. SOLUTION: This herbicidal composition comprises one selected from the group consisting of O-[2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3- pyridazinon-2-yl)phenoxyacetyl]-N,N-dimethylhydroxylamine and O-[2-chloro-4- fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetyl] -N,N- diethylhydroxylamine and ammonium DL-homoalanin-4-yl(methyl)phosphinate as active ingredients. The foliar treatment of weeds can be carried out by using the herbicidal composition to thereby effectively remove various weeds growing in crop or non-crop lands. The weeding efficacy thereof is synergistically increased as compared with the case of single use thereof and the composition can be applied in a low dose. Furthermore, the weeding spectrum is enlarged and a wide range of weeds can selectively by removed especially in corn and soybean fields.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a herbicide composition, and more particularly to a herbicide composition for foliage treatment and a method for herbicide treatment by foliar application of the composition to weeds.

[0002]

2. Description of the Related Art At present, a large number of herbicides are commercially available and used. Therefore, there is a demand for safe herbicides in crops, which have a wide spectrum of herbicides and which have high cropping rates.

[0003]

The present inventors have conducted intensive studies to find an excellent herbicide and found that O- [2-chloro-4]
-Fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O-
[2-Chloro-4-fluoro-5- (4-methyl-5-
Trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and ammonium-DL
-Agriculture by foliar application of a herbicide composition containing-homoalanine-4-yl (methyl) phosphinate (generic name: glufosinate-ammonium, hereinafter referred to as glufosinate-ammonium) as an active ingredient. Various kinds of weeds that occur on land or non-agricultural land can be effectively weeded, and their herbicidal efficacy is synergistically increased as compared with the case where they are used alone. The spectrum has been expanded, and it has been found that a wide range of weeds can be selectively removed in particular in a corn field and a soybean field, and the present invention has been achieved. That is, the present invention relates to O- [2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O- [2-chloro- 4-Fluoro-5-
Foliage treatment containing, as active ingredients, one selected from the group consisting of (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and glufosinate-ammonium as active ingredients. Provided are a herbicide composition for use (hereinafter, referred to as the present composition) and a method for foliar application of the composition to weeds.

[0004]

DETAILED DESCRIPTION OF THE INVENTION O- [2-Chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-) which is one of the active ingredients of the composition of the present invention is described.
Yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O- [2-chloro-4-fluoro-5
-(4-Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine can be produced by the method shown in the following Production Examples. Production Example 1 To a solution obtained by mixing 5.3 g (53.3 mmol) of sodium acetate and about 100 ml of water, 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone was added under ice-cooling. For 20 minutes. The reaction was cooled to room temperature and
5.8 g (21.5 mmol) of -fluoro-4-chloro-5-isopropoxyphenylhydrazine is added to about 20 ml of diethyl ether.
Was added and stirred at room temperature for 1 hour. The ether layer was separated, concentrated, and about 60 ml of THF was added to the residue.
8.3 g (23.0 mmol) of carbethoxyethylidenetriphenylphosphorane was added thereto, and the mixture was refluxed for 2 hours. After distilling off THF under reduced pressure, the residue was subjected to silica gel column chromatography to give 2- [2-fluoro-4-chloro-5-isopropoxyphenyl] -4-methyl-5-
3.8 g of trifluoromethylpyridazin-3-one (10.5
mmol). Dissolve 3.5 g (9.7 mmol) of 2- [2-fluoro-4-chloro-5-isopropoxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one in about 10 ml of concentrated sulfuric acid under ice-cooling and bring to room temperature. The temperature rose. After 10 minutes, about 100 ml of water was added to the reaction solution, and the resulting crystals were collected by filtration and washed successively twice with 20 ml of water and once with 10 ml of hexane.
The obtained crystals were recrystallized from isopropanol to give 2-
3.2 g (9.9 mmol) of [2-fluoro-4-chloro-5-hydroxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one was obtained. 3.2 g of 2- [2-fluoro-4-chloro-5-hydroxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one
(9.9 mmol) was dissolved in about 50 ml of DMF, and 0.44 g of sodium hydride (60% by weight oil dispersion) was dissolved at room temperature.
(11 mmol), left at room temperature for 30 minutes, cooled on ice, and added with ethyl bromoacetate (1.8 g, 11 mmol). After stirring at room temperature for 1 hour, diethyl ether and water were sequentially added and extracted. The organic layer was washed successively with a 10% aqueous hydrochloric acid solution, a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was subjected to silica gel column chromatography to give 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3
-Pyridazinone-2-yl) ethyl phenoxyacetate 2.4g
(5.5 mmol) were obtained. Melting point 102.0 ° C 1.0 g of ethyl 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetate was added to 1,4-dioxane 15m.
and 15 ml of concentrated hydrochloric acid was added. The solution was heated to 60 ° C., stirred for 6 hours, and extracted with ethyl acetate. The organic layer was washed successively with heavy water and saturated saline and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was dissolved in 5 g of thionyl chloride, heated under reflux for 1 hour, and concentrated under reduced pressure. Further dissolved in 20 ml of THF at room temperature,
After dropping 0.65 g of N, N-diethylhydroxylamine, the mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain O- [2-chloro-4-fluoro-5-
1.1 g of (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine (hereinafter referred to as compound A) was obtained. 1H-NMR (250 MHz, CDCl3, TMS, δ
(Ppm)) 1.10 (6H, t, J = 7.1H)
z), 2.42 (3H, q, J = 1.9 Hz), 2.9
4 (4H, q, J = 7.1 Hz), 4.74 (2H,
S), 7.01 (1H, d, J = 6.3 Hz), 7.3
3 (1H, d, J = 9.1 Hz) 7.97 (1H, S) Production Example 2 In Production Example 1, except that N, N-dimethylhydroxylamine was used instead of N, N-diethylhydroxylamine. By performing the same operation, O- [2
-Chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine (hereinafter referred to as compound B) can be obtained. Glufosinate-ammonium is from the Farm Chemicals Handbook
, 1995 (published by Meister, Publishing Co., 19
1995) C188.

[0005] The composition of the present invention can be used to selectively control a wide range of weeds, especially in application to new cultivation methods such as no-till cultivation in corn and soybean fields. The present invention provides an effective composition for controlling a wide range of weeds occurring before the sowing of crops, and does not cause harmful harm to corn or soybean sown after treatment. In addition, the composition of the present invention is useful for cultivating crops to which resistance has been imparted by introducing a herbicide resistance gene or the like described in International Patent Application Publication No. WO95 / 34659. It can be effectively controlled. The composition of the present invention also provides an effective herbicidal composition for controlling a wide range of weeds in non-agricultural land. Also,
In particular, major weeds in corn fields and soybean fields, such as buckwheat, Sanaetada, Sasaenada, Purslane, Shiroza, Ao-geitou, Japanese aphid, Aesculus officinatum, Ebisugusa, Ichibuki, Snapdragon, Asagao, Malva Asagao,
Malva american morning glory, artichoke magnolia, dogwood, onamimomi, sunflower, western convolvulus, euphorbia, americana solanacea, ragweed, etc. While effectively damaging monocotyledonous plants, while not causing harmful harm to crops such as corn and soybean.

In the composition of the present invention, O- [2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-dimethylhydroxyl as an active ingredient Amine and O- [2-chloro-4-fluoro-5-
The mixing ratio between one kind selected from the group consisting of (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and glufosinate-ammonium is the target weed species. May vary depending on the application scene, application conditions, etc.
The weight ratio is usually in the range of 1: 2 to 200.

[0007] The composition of the present invention is usually mixed with a solid carrier, a liquid carrier and the like, and if necessary, added with a surfactant and other auxiliaries for the formulation to form an emulsion, wettable powder, suspension and the like. It is used after conversion. O- [2-Chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O-
[2-Chloro-4-fluoro-5- (4-methyl-5-
Trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and glufosinate-
The total amount of ammonium is generally comprised between 0.5 and 90% by weight, preferably between 1 and 80% by weight.

[0008] The solid carrier used in the preparation includes, for example, clays (kaolinite, diatomaceous earth, synthetic hydrous silicon oxide, fubasami clay, bentonite, acid clay, etc.), talc, and other inorganic minerals (sericite, quartz powder) , Sulfur powder, activated carbon, calcium carbonate, etc.) fine powders and granular materials such as chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, salt ammonium chloride, urea, etc.). Examples of the liquid carrier include water, alcohols (methanol, Ethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methylnaphthalene, etc.), non-aromatic hydrocarbons (hexane, cyclohexane, kerosene, etc.), esters ( Ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile) Etc.), ethers (dioxane, diisopropyl ether), acid amides (dimethylformamide, dimethylacetamide), halogenated hydrocarbons (dichloroethane, trichlorethylene, etc.) and the like.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugars. Alcohol derivatives and the like. Other formulation aids include:
Fixing agents and dispersing agents such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), PAP (acidic isopropyl phosphate), BHT (2,6-tert-butyl-4-methylphenol), BHA (2- / 3-tert-butyl-
4-methoxyphenol), vegetable oil, mineral oil, fatty acid,
Stabilizers such as fatty acid esters are included.

[0010] The composition of the present invention can also be prepared by formulating each active ingredient by the above-mentioned formulation technique and then mixing them. The composition of the present invention thus formulated is applied to a plant as it is or diluted with water or the like. The composition of the present invention can further be expected to enhance herbicidal efficacy by being used in combination with other herbicides, and can also be used in combination with insecticides, fungicides, plant growth regulators, fertilizers, soil improvers, and the like. it can.

[0011] The application rate of the composition of the present invention is as follows: O- [2-chloro-4-fluoro-5- (4-
Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O- [2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-) Yl) phenoxyacetyl] -N, N
The mixture ratio of one selected from the group consisting of diethylhydroxylamine and glufosinate-ammonium, weather conditions, formulation, application time, application method, application place, weeds to be controlled, 1 hectare Per total amount of the active ingredient compound, usually 10 to 200
0 g. Emulsions, wettable powders, suspending agents and the like are applied by diluting a predetermined amount thereof with water of usually 100 to 1000 liters per hectare.

[0012]

[Examples] Formulation examples are shown below. In the following examples, parts represent parts by weight. Formulation Example 1 2 parts of compound A or compound B, 50 parts of glufosinate-ammonium, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 43 parts of synthetic hydrous silicon oxide
The mixture is pulverized and mixed well to obtain a wettable powder. Formulation Example 2 1 part of compound A or compound B, 25 parts of glufosinate-ammonium, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 69 parts of synthetic hydrous silicon oxide
The mixture is pulverized and mixed well to obtain a wettable powder. Formulation Example 3 10 parts of compound A or compound B, 50 parts of glufosinate-ammonium, 3 parts of calcium ligninsulfonate,
2 parts of sodium lauryl sulfate and synthetic hydrous silicon oxide 3
5 parts are well pulverized and mixed to obtain a wettable powder. Formulation Example 4 Compound A or Compound B 25 parts, glufosinate-ammonium 50 parts, calcium lignin sulfonate 3 parts,
2 parts of sodium lauryl sulfate and synthetic hydrous silicon oxide 2
0 parts are pulverized and mixed well to obtain a wettable powder. Formulation Example 5 1 part of compound A or compound B, 25 parts of glufosinate-ammonium, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose)
And 68 parts of water are mixed and wet-ground to a particle size of 5 microns or less to obtain a suspension. Formulation Example 6 2 parts of compound A or compound B, 25 parts of glufosinate-ammonium, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose)
And 67 parts of water are mixed and wet-milled to a particle size of 5 microns or less to obtain a suspending agent. Formulation Example 7 1 part of compound A or compound B, 40 parts of glufosinate-ammonium, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose)
And 53 parts of water are mixed and wet-pulverized to a particle size of 5 microns or less to obtain a suspending agent.

Hereinafter, test examples will be described. Evaluation criteria Herbicidal efficacy was evaluated as “0” when the emergence or growth of the test weed at the time of the survey showed no or little difference from that of the untreated one, and the test plant completely died or emerged or "10" indicates that growth is completely suppressed
And divided into 11 stages of 0 to 10, 0, 1, 2,
3, 4, 5, 6, 7, 8, 9, and 10. The evaluation values "7", "8", "9", and "10" of the herbicidal effect indicate excellent herbicidal effects, and the evaluation value "6" or less indicates insufficient herbicidal effect. Evaluation of phytotoxicity is `` harmless '' when little phytotoxicity is found, `` small '' when mild phytotoxicity is found, `` medium '' when moderate phytotoxicity is found, and `` harmless '' when severe phytotoxicity is found Indicated by "Large". Test Example 1 area 26.5 × 19cm ^2, giant foxtail filled with upland soil in a plastic pot of depth 7 cm, seeded with crabgrass were grown in a greenhouse for 23 days. Compound A10
Part, polyoxyethylene styryl phenyl ether 14
A, an emulsion of compound A obtained by well mixing 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone, a glufosinate-ammonium preparation (trade name: Busta: manufactured by Hoechst Japan KK), and the compound A emulsion A predetermined amount of each of the mixture with the glufosinate-ammonium preparation was diluted with water, and the mixture was uniformly sprayed from above the plant with a small sprayer. After the treatment, the plants were raised in a greenhouse for 4 days, and the herbicidal efficacy was examined. Table 1 shows the results.

[Table 1]

EFFECT OF THE INVENTION By using the composition of the present invention, a wide range of weeds in a field weed and the like, particularly in a corn field and a soybean field can be selectively removed.

Claims (6)

[Claims] (1) O- [2-chloro-4-fluoro-5-
(4-Methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O- [2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-) Pyridazinone-2-yl) phenoxyacetyl]-
One selected from the group consisting of N, N-diethylhydroxylamine and ammonium-DL-homoalanine-4-
A herbicidal composition for foliage treatment comprising yl (methyl) phosphinate as an active ingredient. 2. The herbicidal composition according to claim 1, for controlling weeds in a corn field. 3. The herbicidal composition according to claim 1, for controlling weeds in a soybean field. 4. O- [2-chloro-4-fluoro-5-
(4-Methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenoxyacetyl] -N, N-dimethylhydroxylamine and O- [2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-) Pyridazinone-2-yl) phenoxyacetyl]-
One selected from the group consisting of N, N-diethylhydroxylamine and ammonium-DL-homoalanine-4-
A herbicidal method comprising subjecting a weed to foliage treatment with a herbicide containing yl (methyl) phosphinate as an active ingredient. 5. The method according to claim 4, wherein the weeds in the corn field are treated. 6. The method for treating weeds in a soybean field.
The method for weeding described in 1.