JPH10231205A - 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)phenoxy}propionic acid ester derivative and 6-chloro-N<2> -ethyl-N<4> -isopropyl-1,3,5-triazine-2,4,-diamine 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) phenoxy} propionate and 6-chloro-N ² -ethyl-N
⁴ -isopropyl-1,3,5-triazine-2,4-
A herbicide composition containing a diamine (generic name atrazine, hereinafter referred to as atrazine) as an active ingredient is subjected to foliage treatment on weeds, thereby effectively weeding various weeds that occur on agricultural land or non-agricultural land. And their herbicidal efficacy is synergistically increased compared to when they are used alone, can be applied at lower doses, further broadens the herbicidal spectrum, and has a wide range of weeds, especially in corn and soybean fields. Was found to be able to selectively remove weeds, leading to the present invention. That is, the present invention relates to 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3
-Pyridazinone-2-yl) phenoxydipropionic acid ester derivative and atrazine as active ingredients for foliage treatment (hereinafter referred to as the composition of the present invention) and a method for foliar application of the same to weeds. provide.

[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 phenoxy 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 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. 2- [2-Fluoro-4-chloro-5-hydroxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one
0 g was dissolved in about 20 ml of DMF, 0.5 g of potassium carbonate was added at room temperature, and 0.6 g of methyl 2-bromopropionate was further added. After stirring at room temperature for 3 hours, the mixture was extracted with diethyl ether. The organic layer was washed successively with 10% HCl water, overlay water and saturated saline, 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- {2-chloro-4-
1.0 g of methyl fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxy} propionate was obtained. (Hereinafter referred to as compound A.) Production Example 2 The same procedure as in Production Example 1 was carried out except that methyl 2-bromopropionate was used and the following reaction reagents were used. ｛2-Chloro-4-
A fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxy} 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 1.68 (3H, d, J = 7 Hz), 2.43 (3H,
q, J = 2 Hz), 3.76 (3H, s), 4.73
(1H, q, J = 7 Hz), 6.98 (1H, d, J =
7 Hz), 7.32 (1H, d, J = 8 Hz), 7.9
9 (1H, s) Compound B 1.25 (3H, t, J = 7.3 Hz), 1.68 (3
H, d, J = 6.8 Hz), 2.42 (3H, q, J =
2.0 Hz), 4.21 (2H, q, J = 7.3H)
z), 4.70 (1H, q, J = 6.8 Hz), 6.9
9 (1H, d, J = 6.8 Hz), 7.32 (1H, d, J = 6.8 Hz)
d, J = 9.3 Hz), 7.98 (1H, s) Compound M 1.69 (3H, d, J = 6.9 Hz), 2.42 (3
H, q, J = 1.9 Hz), 4.63 to 4.67 (2
H, m), 4.73 (1H, q, J = 6.9 Hz),
5.20 to 5.34 (2H, m), 5.80 to 5.95
(1H, m), 7.01 (1H, d, J = 6.4H)
z), 7.32 (1H, d, J = 9.3 Hz), 7.9
7 (1H, s) atrazine is described in Farm Chemicals Handbook, 1995 (Me
ister, Publishing Co., 1995) C32.

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, a mixture of 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxy} propionic acid ester derivative and atrazine as active ingredients The ratio can vary depending on the target weed species, application scenes, application conditions, and the like, but is usually 1:10 to 1 by weight.
000.

[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 the 2- {2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxy} propionate derivative and atrazine is generally 0.5 to 0.5. 90% by weight, preferably 1-80% 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.

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) phenoxydipropionate derivative and atrazine, mixing ratio, weather conditions, formulation, application time,
The total amount of the active ingredient compound per hectare is usually 10 to 2000 g, although it may vary depending on the method of application, the place of application, the weed to be controlled, and the target crop. Emulsions, wettable powders,
Suspensions and the like are usually prepared in an amount of 100
Dilute with ~ 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,
1 part of compound K, compound L, compound M or compound N, 25 parts of atrazine, 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 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 N2 parts, Atrazine 35 parts, lignin sulfonate calcium 3 parts, sodium lauryl sulfate 2 parts and synthetic hydrous silicon oxide 58
The mixture is pulverized and mixed well 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,
0.5 parts of compound K, compound L, compound M or compound N,
12.5 parts of atrazine, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 81 parts of water are mixed and wet-pulverized until the particle size becomes 5 μm or less to obtain a suspending agent. Formulation Example 4 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, 17.5 parts of atrazine, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 75.5 parts of water are mixed, and the particle size is 5 microns. The suspension is obtained by wet grinding until the following.

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
A, an atrazine preparation (trade name: AAtrex, manufactured by Ciba Geigy Co., Ltd.)
A predetermined amount of each of the mixture of the emulsion and the atrazine 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]

[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-
(4-Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxydipropionate derivative and 6-chloro-N ² -ethyl-N ⁴ -isopropyl-1,3,5-triazine-2,4-diamine A herbicidal composition for foliage treatment, comprising 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) 2- ｛2-chloro-4-fluoro-5-
(4-Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxydipropionate derivative and 6-chloro-N ² -ethyl-N ⁴ -isopropyl-1,3,5-triazine-2,4-diamine A herbicidal method comprising applying a foliage treatment to a weed with a herbicide contained 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.
Weeding method described in