JPH10231225A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a composition useful as a herbicide for foliar treatment capable of selectively killing a wide range of weeds especially in corn and soybean fields by including a specific compound therein. SOLUTION: This herbicidal composition is obtained by including a 2- 2- chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)pheno xy}propionic acid ester derivative and N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4- benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide as active ingredients at usually 1:(0.1-100) weight ratio therein.

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} propionic acid ester derivative and N- (7-fluoro-3,4-
Dihydro-3-oxo-4-prop-2-ynyl-2H
-1,4-benzoxazin-6-yl) cyclohex-
A herbicidal composition containing 1-ene-1,2-dicarboxamide (generic name flumioxazine, hereinafter referred to as flumioxazine) as an active ingredient is subjected to foliage treatment on weeds, thereby cultivating or non-cultivating lands. Various kinds of weeds can be effectively weeded, and the herbicidal efficacy is synergistically increased as compared with the case where they are used alone, can be applied at a low dose, and the herbicidal spectrum is further expanded, In particular, the present inventors have found that a wide range of weeds can be selectively removed in a corn field and a soybean field, and have reached the present invention. That is,
The present invention relates to 2- {2-chloro-4-fluoro-5- (4-
Herbicide composition for foliage treatment (hereinafter, referred to as the composition of the present invention) containing a methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxydipropionate derivative and flumioxazin as active ingredients, and the same. Provided is a method for foliage treatment of 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 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) flumioxazin is The Pesticide Ma
10th edition (Crop Protection)
Publications, 1994) p. 489.

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) phenoxy} propionic acid ester derivative and flumioxazine as active ingredients are used. The mixture ratio depends on the target weed species, application scene,
Although it may vary depending on the application conditions and the like, the weight ratio is usually 1:
It is in the range of 0.1-100.

[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 flumioxazine is generally 0.5. -90% by weight, preferably 1-80% by weight
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-
Mixing ratio of methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxydipropionate derivative and flumioxazin, weather conditions, formulation, application time, application method, application location, weeds to be controlled, target crops However, 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,
20 parts of compound K, compound L, compound M or compound N, 30 parts of flumioxazine, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 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,
Compound K, Compound L, Compound M or Compound N (10 parts), flumioxazin (15 parts), calcium ligninsulfonate (3 parts), sodium lauryl sulfate (2 parts) and synthetic hydrous silicon oxide (70 parts) 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,
10 parts of compound K, compound L, compound M or compound N, 15 parts of flumioxazine, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 69 parts of water are mixed, and the particle size becomes 5 microns or less. To obtain a suspension. Formulation Example 4 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
5 parts of compound K, compound L, compound M or compound N, 7.5 parts of flumioxazin, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 81.5 parts of water were mixed to give a particle size of 5 parts. The suspension is obtained by wet milling to submicron size.

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 25 × 33 cm ² and a depth of 12 cm was filled with field soil, and seeds of Aquinoe nokorogosa and Brassica napus were sown. 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, and an emulsion of flumioxazin prepared according to the mixture , And a predetermined amount of each of the compound A emulsion and the flumioxazine emulsion were diluted with water, and the mixture was uniformly sprayed from above the plants with a small sprayer. After the treatment, corn and soybean were sowed and bred in a greenhouse for 19 days, and the herbicidal efficacy and the safety against corn and soybean were investigated.
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) phenoxy} propionate derivative and N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H- 1,4-benzoxazin-6-yl) cyclohex-1-ene-1,2
-A herbicide composition for foliage treatment, comprising dicarboxamide 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) phenoxy} propionate derivative and N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H- 1,4-benzoxazin-6-yl) cyclohex-1-ene-1,2
-A herbicidal method characterized by subjecting a weed to foliage treatment with a herbicide containing dicarboxamide 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