JPH10231209A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicidal composition, especially a herbicidal composition suitable for controlling weeds in corn fields and soybean fields. SOLUTION: This herbicidal composition contains a 2- 2-chloro-4-fluoro-5-(4- methyl-5-trifluoromethyl-3-pyridazinon-2-yl)anilino}propionic acid ester derivative and N-(phoshonomethyl)glycine or its salt as active ingredients. When used for the stems and leaves of various weeds, the herbicidal composition can effectively kill the weeds generated in farm lands or non-farm lands, and the herbicidal effects are synergistically increased in comparison with cases wherein the ingredients are singly used. The herbicidal composition can be applied at low dosages and has an expanded herbicidal spectrum. The herbicidal composition is especially effective for the control of a wide range of weeds in corn fields and soybean fields, before the crops are sowed, and does not give such a chemical damage as causing a problem to the corns and soybeans which are sowed after the treatment.

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 as a result, have found that 2- ｛2-chloro-4
-Fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino} propionate ester derivative and N- (phosphonomethyl) glycine (generic name glyphosate, hereinafter referred to as glyphosate) or a mixture thereof By applying foliar treatment to weeds with a herbicidal composition containing salt and an active ingredient, weeds can be effectively removed from various weeds that occur on agricultural or non-agricultural lands. The present invention has found that it is possible to selectively weed a wide range of weeds in a corn field and a soybean field, which increase synergistically, can be applied at a low dose, and further broaden the herbicidal spectrum as compared with the case where the present invention is used. Reached. That is, the present invention relates to 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) anilino}
Provided is a herbicidal composition for foliage treatment containing the propionate derivative and glyphosate or a salt thereof as active ingredients (hereinafter, referred to as the composition of the present invention) and a method for foliar application of the composition to weeds.

[0004]

DESCRIPTION OF THE PREFERRED EMBODIMENTS One of the active ingredients of the composition of the present invention, 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-), is used.
Il) In the anilino dipropionate derivative, the ester is a C1-C7 alkyl ester, C5
To C6 cycloalkyl ester and C2 to C6 alkenyl ester, and these compounds can be produced by the methods shown in the following production examples. Production Example 1 1) 30 g of 4-chloro-2-fluoroaniline was mixed with 150 ml of concentrated hydrochloric acid and stirred at 50 ° C. for 30 minutes. A solution obtained by dissolving 15 g of sodium nitrite in 40 ml of water was added dropwise to this mixture at 0 ° C. over 10 minutes. After stirring at 0 ° C for 1 hour, the mixture was cooled to -50 ° C. A solution prepared by dissolving 132 g of stannous chloride in 132 g of concentrated hydrochloric acid was quickly added dropwise at -50 ° C, and the temperature was gradually returned to room temperature and stirred for 1 hour.
The resulting solid was collected by filtration and dried at 80 ° C. under reduced pressure to obtain 70 g of crude crystals of 2-fluoro-4-chlorophenylhydrazine hydrochloride. 2) 49.2 g of sodium acetate and 1,1-dibromo-
40.5 g of 3,3,3-trifluoroacetone is added to water 40
Dissolved in 0 ml and heated at 80-90 ° C for 40 minutes. The solution was cooled to 0 ° C., and 75 g of crude crystals of 2-fluoro-4-chlorophenylhydrazine hydrochloride were added. The mixture was stirred at room temperature for 70 minutes, and the resulting crystals were collected and dried under reduced pressure.
3,3,3-trifluoro-2-oxopropanal 1
-(4-chloro-2-fluorophenylhydrazone) 3
2 g were obtained. 3) 3 g of 3,3,3-trifluoro-2-oxopropanal 1- (4-chloro-2-fluorophenylhydrazone) and 22.3 g of carboxyethylidenetriphenylphosphorane were dissolved in 110 ml of THF,
Heated to reflux for an hour. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 7 g of 2- (2-fluoro-4-chlorophenyl) -4-methyl-5-trifluoromethylpyridazin-3-one. 4) 50 ml of concentrated sulfuric acid was ice-cooled, and 7 g of 2- (2-fluoro-4-chlorophenyl) -4-methyl-5-trifluoromethylpyridazin-3-one was dissolved therein. To this, 1.51 g of fuming nitric acid was added dropwise at 5 ° C or less, and 0-5 ° C.
For 1 hour. The reaction solution was poured into 300 ml of ice water,
After three extractions with 50 ml of diethyl ether, the combined extracts were washed successively with about 100 ml of water and 100 ml of heavy water. The organic layer was dried over anhydrous magnesium sulfate, semi-concentrated, and the residue was subjected to silica gel column chromatography to give 2- (2-fluoro-4-chloro-5-nitrophenyl) -4-methyl-5-trifluoromethyl 6.1 g of pyridazin-3-one were obtained. 5) 5.0 g of iron powder, 75 ml of acetic acid and 10 ml of water were mixed, heated to about 80 ° C., and aged for about 15 minutes. In 40 ml of ethyl acetate, 6.0 g of 2- (2-fluoro-4-chloro-5-nitrophenyl) -4-methyl-5-trifluoromethylpyridazin-3-one was dissolved and added dropwise at 80 ° C. or lower. After aging at about 80 ° C. for 1 hour, it was allowed to cool to room temperature. After extracting twice with 100 ml of ethyl acetate, the combined extracts were washed twice with 50 ml of water and once with superimposed water. The organic layer was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (2-fluoro-4-chloro-5-
5.1 g of (aminophenyl) -4-methyl-5-trifluoromethylpyridazin-3-one were obtained. 6) Dissolve 0.6 g of 2- (2-fluoro-4-chloro-5-aminophenyl) -4-methyl-5-trifluoromethylpyridazin-3-one in 10 ml of methyl 2-bromopropionate and at 110 ° C. Stirred for 10 minutes. After allowing the reaction solution to cool to room temperature, it was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 2- {2-chloro-4-fluoro-5
-(4-Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino} propionate methyl
18 g (hereinafter referred to as compound A) were obtained. Production Example 2 In the above Production Example 1-6), except that methyl 2-bromopropionate was used and the following reaction reagents were used, the same operation was carried out to obtain the desired 2- {2-chloro-4- Fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino} propionate derivative can be obtained.

[Table 1] (In the table, i represents iso, t represents tertiary, and c represents cyclo) ¹ H-NMR (250 MHz or 300 MH, CDC
l ₃ , TMS, δ (ppm)) Compound A 1.52 (3H, d, J = 6.9 Hz), 2.42 (3
H, q, J = 1.7 Hz), 3.75 (3H, s),
4.10 (1H, dt, J = 7.0, 7.0 Hz),
4.80 (1H, d, J = 7.0 Hz), 6.57 (1
H, d, J = 6.4 Hz), 7.24 (1H, d, J =
9.2 Hz), 7.98 (1 H, s) Compound B 1.25 (3 H, t, J = 7.5 Hz), 1.51 (3
H, d, J = 7.0 Hz), 2.42 (3H, q, J =
1.8 Hz), 4.0-4.18 (3H, m), 4.8
2 (1H, d, J = 7.9 Hz), 6.59 (1H,
d, J = 6.3 Hz), 7.23 (1H, d, J = 9.
Glyphosate is obtained from Farm Chemicals Handbook, 1995.
(Meister, Published Co., 1995) C1
Compound described on page 88. Further, the salt in the present invention means all agrochemically acceptable salts such as amine salts such as alkali metal salts, alkaline soil metal salts, isopropylamine salts and the like, and ammonium salts.

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. Especially the major weeds in corn fields,
For example, buckwheat, Sanaetada, U.S.
Purslane, Shiroza, Aogaito, Noharagarashi, Utsunotsusanem, Ebisugusa, Ichibi, U.S. stag, U.S. morning glory, Maruba Asagao, Malva U.S. An effective herbicidal composition for controlling monocotyledonous plants such as dicotyledonous plants, such as dog millet, enokorogosa, achinonokorogosa, chinoko nokoro, meishiba, ohishiba, seiban sorghum, shibagimugi, and shatter cane, before sowing the crop. It does not cause harmful harm to corn or soybean sown after treatment.

In the composition of the present invention, 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino} propionate as an active ingredient and glyphosate or The mixing ratio of the salt may vary depending on the target weed species, application scenes, application conditions, and the like, but is usually in the range of 1:10 to 1000 by weight.

[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. In these preparations, the total amount of 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino} propionate derivative and glyphosate or a salt thereof is contained. Generally 0.5-90% by weight, preferably 1-8
0% by weight is contained.

[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.

The application rate of the composition of the present invention is determined based on the amount of the active ingredient compound, 2- {2-chloro-4-fluoro-5- (4-
Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino dipropionate ester and its mixture ratio of glyphosate or its salt, weather conditions, formulation form, application time, application method, application place, weeds to be controlled, target Although it may vary depending on the crop, the total amount of the active ingredient compound is usually 10 to 2000 g per hectare.
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 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
1 part of compound K, compound L, compound M or compound N, 50 parts of glyphosate, calcium ligninsulfonate 3
Parts, 2 parts of sodium lauryl sulfate and 44 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 2 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
1.5 parts of compound K, compound L, compound M or compound N,
A wettable powder is obtained by sufficiently pulverizing and mixing 70 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 23.5 parts of synthetic silicon oxide hydrous. Formulation Example 3 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
0.5 parts of compound K, compound L, compound M or compound N,
A suspension is obtained by mixing 25 parts of glyphosate, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 68.5 parts of water, and wet-grinding the mixture until the particle size becomes 5 microns or less. . Formulation Example 4 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
Compound K, compound L, compound M or compound N, 1 part, glyphosate 35 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 58 parts are mixed, and the particle size is reduced to 5 microns or less. The suspension is obtained by wet-grinding until complete.

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 seeds of Aquino nokorogosa and Meeshiba were sowed and grown in a greenhouse for 23 days. Compound A10
Part, polyoxyethylene styryl phenyl ether 14
, Calcium dodecylbenzenesulfonate, 6 parts of xylene, and 35 parts of xylene and 35 parts of cyclohexanone, an emulsion of Compound A, a glyphosate preparation (trade name: Roundup by Monsanto Japan), and Compound A A predetermined amount of each mixture of the emulsion and the glyphosate preparation was diluted with water, and the mixture was uniformly sprayed from above the plants with a small sprayer. After the treatment, the plants were raised in a greenhouse for 4 days, and the herbicidal efficacy was examined. Table 2 shows the results.

[Table 2]

[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) 2- {2-chloro-4-fluoro-5-
A herbicide composition for foliage treatment comprising (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilinodipropionic acid ester derivative and N- (phosphonomethyl) glycine or a salt thereof as active ingredients. Stuff. 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) 2- ｛2-chloro-4-fluoro-5-
Foliar treatment of a weed with a herbicide containing (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) anilino dipropionate and N- (phosphonomethyl) glycine or a salt thereof as active ingredients. Characteristic weeding method. 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.
Weeding method described in