JPH10226603A - 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 a 2-chloro-4-fluoro-5-(4- methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetic ester derivative 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 be 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 as a result, have found that 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3
-Pyridazinone-2-yl) phenoxyacetic acid ester derivative and ammonium-DL-homoalanine-4-yl (methyl) phosphinate (generic name glufosinate-
Ammonium, hereinafter referred to as glufosinate-ammonium. A) a herbicidal composition containing
By foliar treatment of weeds, weeds can be effectively removed from a variety of weeds generated on agricultural or non-agricultural lands, and the herbicidal efficacy is synergistically increased as compared with the case where they are used alone. The present invention has been found to be able to be applied in a medicinal amount, to broaden the herbicidal spectrum, and to be able to selectively remove a wide range of weeds, particularly in a corn field and a soybean field. That is, the present invention relates to a herbicide for foliar treatment containing 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and glufosinate-ammonium as active ingredients. The present invention also provides a herbicidal composition (hereinafter referred to as the composition of the present invention) and a method for herbicidal treatment of weeds with foliage.

[0004]

DETAILED DESCRIPTION OF THE INVENTION 2-Chloro-4-fluoro-5- (4-methyl-5) which is one of the active ingredients of the composition of the present invention.
-Trifluoromethyl-3-pyridazinone-2-yl)
In the phenoxyacetic acid ester derivative, the ester means C1 to C7 alkyl ester, C5 to C6 cycloalkyl ester, and C2 to C6 alkenyl ester, and these compounds 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
2.4 g (5.5 mmol) of ethyl -pyridazinone-2-yl) phenoxyacetate (hereinafter referred to as compound A) was obtained. Melting point: 102.0 ° C. Production Example 2 In the above Production Example 1, except that the following reagents were used instead of ethyl bromoacetate, the same operation was carried out to obtain the desired 2-chloro-4-fluoro-5- ( 4
-Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester 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 E 0.88 (3H, t, J = 7 Hz), 1.2-1.4
(4H, m), 1.55-1.70 (2H, m), 2.
43 (3H, q, J = 2 Hz), 4.19 (2H, t,
J = 7 Hz), 4.68 (2H, s), 6.98 (1
H, d, J = 7 Hz), 7.33 (1H, d, J = 8H)
z), 7.99 (1H, s) Compound H 1.26 (6H, d, J = 6.3 Hz), 2.43 (3
H, q, J = 2 Hz), 4.65 (2H, s), 5.0
5-5.18 (1H, m), 6.98 (1H, d, J =
7 Hz), 7.33 (1H, d, J = 8 Hz), 7.9
8 (1H, s) Compound I 0.90 (6H, d, J = 6.6 Hz), 1.85 −
2.03 (1H, m), 2.42 (3H, q, J = 1.
8 Hz), 3.98 (2H, d, J = 6.5 Hz),
4.70 (2H, s), 6.99 (1H, d, J = 6.
3Hz), 7.33 (1H, d, J = 9.1 Hz),
7.98 (1H, s) Compound J 1.45-1.53 (9H, m), 2.39-2.45
(3H, m), 4.58-4.60 (2H, m), 6.
96-7.00 (1H, m), 7.30-7.36 (1
H, m), 7.96-8.00 (1H, m) Compound K 1.5-1.9 (8H, m), 2.43 (3H, q, J
= 2 Hz), 4.65 (2H, s), 5.2-5.4
(1H, m), 6.97 (1H, d, J = 7 Hz),
7.33 (1H, d, J = 8 Hz), 7.98 (1H, d, J = 8 Hz)
s) Compound M 2.42 (3H, q, J = 1.9 Hz), 4.67-
4.72 (2H, m), 5.23-5.37 (2H,
m), 5.84-5.98 (1H, m), 7.00 (1
H, d, J = 6.3 Hz), 7.33 (1H, d, J =
9.2 Hz), 7.99 (1H, s) Compound N 2.42 (3H, q, J = 1.8 Hz), 4.68−
4.71 (1H, m), 4.77 (2H, s), 4.9
4-5.01 (1H, m), 7.03 (1H, d, J =
6.3 Hz), 7.26-7.31 (1H, m), 7.
34 (1H, d, J = 9.0 Hz), 7.99 (1H, d, J = 9.0 Hz)
s) Glufosinate-ammonium is from Farm Chemicals Han
dbook, 1995 (published by Meister, PublishingCo.,
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, the mixing ratio of 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and glufosinate-ammonium as active ingredients Can vary depending on the target weed species, application scenes, application conditions, etc., but usually in a weight ratio of 1: 2 to 2
00 range.

[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-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and glufosinate-ammonium is generally 0.5 to 90. % By weight, preferably 1 to 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.

The application rate of the composition of the present invention is as follows: the active ingredient compounds, 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and glufosinate -The mixing ratio of ammonium, weather conditions, formulation, application time, application method, location of application, weeds to be controlled and target crops may vary, but the total amount of the active ingredient compound per hectare is usually 10 to 2000 g. Emulsions, wettable powders, suspending agents and the like are usually used in a predetermined amount per hectare.
Dilute with 00-1000 liters of water and apply.

[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,
Compound K, compound L, compound M or compound N, 2 parts, glufosinate-ammonium, 50 parts, calcium ligninsulfonate, 3 parts, sodium lauryl sulfate, 2 parts and 43 parts of synthetic hydrous silicon oxide are pulverized and mixed well 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,
Compound K, Compound L, Compound M or Compound N, 1 part, glufosinate-ammonium, 25 parts, calcium ligninsulfonate, 3 parts, sodium lauryl sulfate, 2 parts, and 69 parts of synthetic hydrous silicon oxide are pulverized and mixed to obtain a wettable powder. Formulation Example 3 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 (10 parts), glufosinate-ammonium (50 parts), calcium ligninsulfonate (3 parts), sodium lauryl sulfate (2 parts) and synthetic hydrous silicon oxide (35 parts) are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 4 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
25 parts of compound K, compound L, compound M or compound N, 50 parts of glufosinate-ammonium, 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 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, glufosinate-ammonium, 25 parts, polyoxyethylene sorbitan monooleate, 3 parts, CMC (carboxymethylcellulose), 3 parts, and 68 parts of water are mixed to give a particle size of 5 microns or less. The suspension is obtained by wet pulverization until the suspension is obtained. Formulation Example 6 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 N2 parts, glufosinate-ammonium 25 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethylcellulose) 3 parts and water 67 parts are mixed to obtain a particle size of 5 microns or less. The suspension is obtained by wet pulverization until the suspension is obtained. Formulation Example 7 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, glufosinate-ammonium, 40 parts, polyoxyethylene sorbitan monooleate, 3 parts, CMC (carboxymethylcellulose), 3 parts, and 53 parts of water are mixed to give a particle size of 5 microns or less. The suspension is obtained by wet pulverization until the suspension is obtained.

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 cylindrical plastic pot having a diameter of 17 cm and a depth of 14.5 cm was filled with field soil, and seeds of Aquinoe nokorogosa, Brassica juncea and Pseudomonata were sowed. In a greenhouse, Achinoe nokorogosa was grown for 42 days and Inubie and Pseudomonata were grown for 31 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 glufosinate-ammonium preparation (trade name: Busta: A predetermined amount of each of the mixture of the compound A emulsion and 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 2 shows the results.

[Table 2] Test Example 2 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 E10
Part, polyoxyethylene styryl phenyl ether 14
Of Compound E, a glufosinate-ammonium preparation, and a mixture of the Compound E emulsion and a glufosinate-ammonium preparation obtained by thoroughly mixing 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone Were diluted with water and sprayed evenly 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 3 shows the results.

[Table 3]

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-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2
A herbicidal composition for foliage treatment, comprising as active ingredients: -yl) phenoxyacetic acid ester derivative and ammonium-DL-homoalanine-4-yl (methyl) phosphinate. 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-Chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2
-A herbicide comprising foliar treatment of a weed with a herbicide comprising -yl) phenoxyacetic acid ester derivative and ammonium-DL-homoalanine-4-yl (methyl) phosphinate as active ingredients. 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.