JPH10226604A - 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 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 3-isopropyl-1 H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide as active ingredients.

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 3-isopropyl-1H-2,1,3-benzothiadiazine-4 ( 3H)
-One 2,2-dioxide (generic name bentazone; hereinafter referred to as bentazone) as an active ingredient is subjected to foliage treatment on weeds to produce various types of crops generated on agricultural or non-agricultural lands. Weeds can be effectively weeded, and their herbicidal efficacy is synergistically increased compared to when they are used alone, they can be applied at low doses, and the herbicidal spectrum is further expanded, especially in corn fields and soybeans. The present inventors have found that weeds can be selectively removed from a wide range of weeds in a field, and have reached the present invention. 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- It comprises one selected from the group consisting of 4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and bentazone as active ingredients. Provided is a herbicide composition for foliage treatment (hereinafter, referred to as the composition of the present invention) 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. Bentazone is described in the Farm Chemicals Handbook, 1995 (Meister
, Publishing Co., 1995) C48.

The composition of the present invention provides an effective herbicidal composition for selectively controlling a wide range of weeds and for applying to new cultivation methods such as no-tillage cultivation. In particular, major weeds in corn fields and soybean fields, for example, buckwheat, Sanaetada, A. serrata, Purslane, Shiroza, Ao-getou, Noharagarashi, Satsuma-kusananem, Ebisugusa, Ichibi, S. serrata, A. , Malva American morning glory, Artemisia americana, Dogwood physalis, Onamimomi, Sunflower, Pacific convolvulus, Euphorbiaceae, American dungweed, Ragweed, and other dicotyledonous plants, such as Inubie, Enokorogosa, Achinoekonokogusa, Kinnoenokoro, Mechinobako
While effectively weeding monocotyledonous plants such as oakgrass, sorghum sorghum, barley, and shutter cane, it does not cause 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 mixture ratio of one kind selected from the group consisting of (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and bentazone is the target weed species, application scene Although it may vary depending on the application conditions and the like, 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-
The total amount of one selected from the group consisting of trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetyl] -N, N-diethylhydroxylamine and bentazone is generally 0.5 to 90% by weight, preferably 1 to 80% by weight. %.

[0008] The solid carrier used in the formulation 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
-Mixing ratio of one selected from the group consisting of diethylhydroxylamine and bentazone, weather conditions, preparation form, application time, application method, application place, weeds to be controlled, target crops, but the active ingredient compound per hectare Is usually 10 to 2000 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, 56 parts of bentazone, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 37 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 2 1 part of Compound A or Compound B, 28 parts of bentazone, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 66 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 3 10 parts of compound A or compound B, 60 parts of bentazone, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 25 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 4 25 parts of Compound A or Compound B, 50 parts of bentazone, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 20 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 5 1 part of compound A or compound B, 28 parts of bentazone, 3 parts of polyoxyethylene sorbitan monooleate, CMC
(Carboxymethylcellulose) 3 parts and water 65 parts are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspending agent. Formulation Example 6 2 parts of compound A or compound B, 28 parts of bentazone, 3 parts of polyoxyethylene sorbitan monooleate, CMC
(Carboxymethylcellulose) 3 parts and water 64 parts are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspending agent. Formulation Example 7 1 part of compound A or compound B, 40 parts of bentazone, 3 parts of polyoxyethylene sorbitan monooleate, CMC
3 parts of (carboxymethylcellulose) and 53 parts of water are mixed and wet-pulverized until the particle size becomes 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 A plastic pot having an area of 26.5 × 19 cm ² and a depth of 7 cm was filled with field soil, and corn, soybean, Aquinoenokorogusa, and Meechishiba were sown, and corn was grown for 16 days in a greenhouse, and soybean, Aquinoenokorogusa, and Meishishiba were grown for 23 days. I let it. And sowed in a greenhouse for 23 days. An emulsion of compound A obtained by thoroughly mixing 10 parts of compound A, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone, a bentazone preparation (trade name Vasagran: Vasaglan popular) A predetermined amount of each of the compound A emulsion and the mixed solution of the compound A emulsion and the bentazone preparation was diluted with water, and the mixture was uniformly sprayed from above the plant with a small atomizer. The plants were raised in a greenhouse for 4 days after the treatment, and the herbicidal efficacy and the safety to corn and soybean were investigated. Table 1 shows the results.

[Table 1]

[0014]

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 3-isopropyl-1H-2,1,3-
A herbicide composition for foliage treatment, comprising benzothiadiazin-4 (3H) -one 2,2-dioxide 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 3-isopropyl-1H-2,1,3-
A herbicidal method comprising applying a herbicide containing benzothiadiazin-4 (3H) -one 2,2-dioxide as an active ingredient to weeds. 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.