JPH10231216A - Herbicide composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicide composition, especially a forage-treating herbicide composition suitable for controlling weeds in a barley field. SOLUTION: A herbicide composition composed of 2-chloro-4-fluoro-5-(4- methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl (1-5C) noncyclic hydrocarbonyl ether and one kind selected from a group consisting of ethyl-(R)-2-[4-(6-chloro-1,3- benzoxazol-2-yloxy)phenoxy]propanoate and methyl(RS)-2-[4-(2,4-dichlorophenoxy) phenoxy]propionate as active components is applied on weeds for forage treatment. This enables the effective control of various kinds of weeds growing in a crop land or a non-crop land, the synergistic enhancement of the controlling activity compared with single use of each of them, low-dose application, further the widening of herbicidal spectrum, and the selective controlling of wide range of weeds especially in a barley field.

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) phenyl C1-C5 acyclic hydrocarbyl ether and ethyl- (R) -2
-[4- (6-chloro-1,3-benzoxazole-2
-Yloxy) phenoxy] propanoate (generic name fenoxaprop-P-ethyl, hereinafter referred to as phenoxaprop-P-ethyl) and methyl (RS) -2- [4
-(2,4-dichlorophenoxy) phenoxy] propionate (generic name: diclopop-methyl, hereinafter referred to as diclo-op-methyl) and a herbicide composition containing, as an active ingredient, a weed killer composition. By foliar treatment, various weeds generated on agricultural or non-agricultural lands can be effectively weeded, and the herbicidal efficacy is synergistically increased as compared with the case where they are used alone. Can be applied in quantity, 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 wheat field, and have reached the present invention. That is, the present invention provides 2-
Chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenyl C1-C5 acyclic hydrocarbyl ether (hereinafter referred to as ether compound) and fenoxaprop-
Provided is a herbicidal composition (hereinafter, referred to as the present invention composition) containing, as an active ingredient, one selected from the group consisting of P-ethyl and diclofopmethyl, and a herbicidal method for foliar application of the composition to a weed. .

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION In the ether compound which is one of the active ingredients of the composition of the present invention, C1-C5 acyclic hydrocarbyl means 2-propynyl, 1-methyl-2-propynyl, allyl, It means 1-methylallyl, isopropyl or ethyl, 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 carboxyethylidenetriphenylphosphorane was added thereto, and the mixture was heated under reflux for 2 hours. THF was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to give 2- [2-fluoro- 3.8 g (10.5 mm) of 4-chloro-5-isopropoxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one
ol) obtained. 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
2 g was dissolved in about 50 ml of DMF, and 2.0 g of potassium carbonate was added thereto at room temperature. Further, 1.3 g of propargyl bromide was added, followed by stirring at room temperature for 30 minutes. Water 1
The resulting crystals were collected by filtration, washed with hexane, and recrystallized from isopropanol.
-[2-fluoro-4-chloro-5- (2-propynyloxy) phenyl] -4-methyl-5-trifluoromethylpyridazin-3-one (hereinafter referred to as compound A) 3.
4 g (mp 140.7 ° C: decomposition) were obtained. Production Example 2 In the above Production Example 1, instead of propargyl bromide,
By performing the same operation except that the following reaction reagents are used, the desired ether compounds can be obtained respectively.

[Table 1] ¹ H-NMR (300 MH, CDCl ₃ , TMS, δ
(Ppm)) Compound E 1.46 (3H, t, J = 5.8 Hz), 2.44 (3
H, q, J = 1.5 Hz), 4.07 (2H, q, J =
5.8 Hz), 6.94 (1H, d, J = 5.0H)
z), 7.29 (1H, d, J = 7.5 Hz), 8.0
1 (1H, s) Compound F 1.38 (6H, d, J = 6.3 Hz), 2.43 (3
H, q, J = 2.0 Hz), 4.47 (1H, m),
6.99 (1H, d, J = 5.0 Hz), 7.29 (1
H, d, J = 9.5 Hz), 8.00 (1H, s) Fenoxaprop-P-ethyl was obtained from Farm Chemicals Han.
dbook, 1995 (published by Meister, PublishingCo.,
1995) C164. Dichlophop methyl is described in Farm Chemicals Handbook, 1995.
(Meister, Publishing Co., 1995) C2
Compound described on page 01.

[0005] The composition of the present invention provides an effective herbicidal composition for the selective control of a wide range of weeds and for application to new cultivation methods such as no-tillage cultivation. Main weeds of wheat fields, in particular, for example, chickweed, jaemgra, oinoufuguri, hirasabasou, violet, himeodorikosou, hotokenoza, nazuna, nogeshi, inukamitsure, noharagarashi, forget-me-not, swordfish, blossoms Leaf plants and monocotyledonous plants such as barnyardgrass, enokorogusa, sparrow caterpillar, hornbudget, mugwort, chahiki and oats, etc., are effectively weeded, and phytotoxicity causing problems on crops such as wheat and corn which is a post-crop of wheat. Does not occur.

[0006] In the composition of the present invention, the mixing ratio of the ether compound as an active ingredient and one kind selected from the group consisting of fenoxaprop-P-ethyl and diclofopmethyl is determined based on the target weed species, Although it may vary depending on the situation, application conditions, and the like, the weight ratio is usually 1: 0.5 to 100.
It is in the range of 0.

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 preparation, to give an emulsion, a wettable powder, a suspension and the like. It is used after being formulated. In these preparations, the total amount of the ether compound and one kind selected from the group consisting of fenoxaprop-P-ethyl and diclopropmethyl is generally 0.5 to 90% by weight, preferably 1 to 80% by weight. % 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 soil or a plant as it is or after 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 ether compound, which is an active ingredient compound, and fenoxaprop-P-.
Mixing ratio of ethyl and dicloflop methyl, weather conditions,
The total amount of the active ingredient compound per hectare is usually 2 to 1000 g, although it may vary depending on the formulation form, application time, application method, application place, weeds to be controlled and target crops. 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 or Compound F or 25 parts, fenoxaprop-P-ethyl 1
5 parts, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 55 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 or Compound F1 part, fenoxaprop-P-ethyl 70
Parts, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 24 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 3 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 25 parts, fenoxaprop-P-ethyl 1
5 parts, polyoxyethylene sorbitan monooleate 3
Parts, 3 parts of CMC (carboxymethylcellulose) and 54 parts of water are mixed and pulverized until the particle size becomes 5 microns or less to obtain a suspending agent. Formulation Example 4 Compound A, Compound B, Compound C, Compound D, Compound E or 1 part of Compound F, fenoxaprop-P-ethyl 70
Part, polyoxyethylene sorbitan monooleate 3
Parts, 3 parts of CMC (carboxymethylcellulose) and 23 parts of water are mixed and pulverized until the particle size becomes 5 microns or less to obtain a suspending agent. Formulation Example 5 1 part of compound A, compound B, compound C, compound D, compound E or compound F, 50 parts of diclohop methyl, 3 parts of calcium ligninsulfonate, sodium lauryl sulfate 2
Parts and 54 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 6 Compound A, Compound B, Compound C, Compound D, Compound E or 7 parts of compound F, 70 parts of diclohop methyl, 3 parts of calcium ligninsulfonate, sodium lauryl sulfate 2
And 18 parts of synthetic hydrous silicon oxide are crushed and mixed well to obtain a wettable powder. Formulation Example 7 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F 0.2 part, Diclohop methyl 40 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC
(Carboxymethylcellulose) 3 parts and water 53.8
Parts are mixed and ground to a particle size of 5 microns or less to obtain a suspending agent. Formulation Example 8 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 3 parts, diclohop methyl 30 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 61 parts Mix and grind to a particle size of 5 microns or less to obtain a suspension.

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 Upland soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and wheat and locust bean were sown and grown in a greenhouse. Compound A 5 parts, polyvinyl alcohol 10% aqueous solution 50 parts, water 45 parts are mixed and pulverized to a particle size of 5 microns or less, suspension of compound A, fenoxaprop-P-ethyl preparation (Trade name: Pumas: manufactured by Hoechst Co.) and a predetermined amount of a mixture of the compound A suspension and the fenoxaprop-P-ethyl preparation were diluted with water, and the foliage was applied from above the plant using a small sprayer. Sprayed evenly over the entire surface. The same operation was performed for compound B. The plants were grown in a greenhouse for 4 days after the treatment, and the herbicidal efficacy and safety to wheat were investigated. Table 2 shows the results.

[Table 2] Test Example 2 A field-shaped soil was packed in a cylindrical plastic pot having a diameter of 17 cm and a depth of 14.5 cm, and seeds of Achinoekorogosa and Echinochloa were sown. In a greenhouse, Achinonochorogosa was grown for 42 days and Echinochloa was grown for 31 days. Compound A 5 parts, polyvinyl alcohol 10% aqueous solution 50 parts, water 45 parts are mixed and pulverized to a particle size of 5 microns or less, suspension of compound A, fenoxaprop-P-ethyl preparation (Trade name: Pumas: manufactured by Hoechst Co.) and a predetermined amount of a mixture of the compound A suspension and the fenoxaprop-P-ethyl preparation were diluted with water, and the foliage was applied from above the plant using a small sprayer. Sprayed evenly over the entire surface. 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]

[0014]

EFFECTS OF THE INVENTION By using the composition of the present invention, a wide range of weeds in a field such as a field weed can be selectively removed.

Claims (4)

[Claims] (1) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2
-Yl) phenyl C1-C5 acyclic hydrocarbyl ether, ethyl- (R) -2- [4- (6-chloro-1,3-benzoxazol-2-yloxy) phenoxy] propanoate and methyl (RS) -2- [4
-(2,4-dichlorophenoxy) phenoxy] propionate; and a herbicide composition for foliage treatment, comprising as an active ingredient. 2. The herbicidal composition according to claim 1, for controlling weeds in a wheat field. (3) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2)
-Yl) phenyl C1-C5 acyclic hydrocarbyl ether, ethyl- (R) -2- [4- (6-chloro-1,3-benzoxazol-2-yloxy) phenoxy] propanoate and methyl (RS) -2- [4
-(2,4-dichlorophenoxy) phenoxy] a herbicide comprising, as an active ingredient, a herbicide comprising one selected from the group consisting of propionates, and the foliage treatment of weeds. 4. The method according to claim 3, wherein the weeds in the wheat field are treated.