JPH10231213A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a composition useful as a herbicidal composition capable of selectively killing a wide range of weeds especially in corn fields by including a specific ether compound and another specified compound. SOLUTION: This composition contains (A) a 2-chloro-4-fluoro-5-(4-methyl-5- trifluoromethyl-3-pyridazinon-2-yl)phenyl 1-5C acyclic hydrocarbyl ether and (B) one kind of compound selected from 2-(2-benzothiazoloxy)-N-methyl-N- phenylacetamide, 4'-fluoro-N-methyl-2-(5-trifluoromethyl-1,3,4-thiazol-2-yloxy) acetanilide and 4'-fluoro-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiazol-2-yloxy) acetamide as active ingredients usually in an (A):(B) weight ratio of 1:5 to 1000.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a herbicidal composition.

[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, 2- (2-benzothiazolyloxy) -N-methyl-N-phenylacetamide (generic name mefenacet, hereinafter referred to as mefenacet), 4'-fluoro-N-methyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy) acetanilide (hereinafter referred to as anilide compound)
And 4'-fluoro-N-isopropyl-2- (5-trifluoromethyl-1,3,4-thiadiazole-2-
Iloxy) acetanilide (generic name thiafluamide,
1) selected from the group consisting of:
By treating a soil or a weed with a herbicidal composition containing a seed and an active ingredient as an active ingredient, it is possible to effectively weed out various weeds that occur on agricultural or non-agricultural land, and the herbicidal efficacy of the herbicide is reduced by The present invention has been found to increase synergistically compared with the case of using alone, to be able to be applied at a low dose, to further broaden the herbicidal spectrum, and to be able to selectively weed a wide range of weeds, particularly in a corn field. Was. That is, the present invention relates to 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2
-Yl) phenyl A herbicidal composition containing a C1-C5 acyclic hydrocarbyl ether (hereinafter referred to as an ether compound) and one selected from the group consisting of mefenacet, an anilide compound and thiafluamide as active ingredients. An agent composition (hereinafter, referred to as the composition of the present invention) is provided.

[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) Mefenacet is obtained from Farm Chemicals Handbook, 1995
(Meister, Publishing Co., 1995) C2
Compound described on page 00. The anilide compound is produced according to Production Example 1 described in European Patent Application Publication No. EP 0626380 A1 (solidification point: 51 ° C.). Thiafluamide is described in German Patent Application DE 32 184.
82A1.

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. While effectively weeding off dicotyledonous plants and monocotyledonous plants such as barnyardgrass, enokorogosa, Achinonokorogosa, chinoko nokoro, crabgrass, ohishiba, seiban sorghum, barley, corngrass, etc. It does not cause harm to the patient.

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 mefenacet, an anilide compound and thiafluamide is determined based on the target weed species, application scene, application conditions and the like. The weight ratio is usually in the range of 1: 5 to 500.

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. Etc. and used as a formulation. In these preparations, the total amount of ether compound and one kind selected from the group consisting of mefenacet, anilide compound and thiafluamide is generally 0.1.
The content is 5 to 90% by weight, preferably 1 to 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 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 determined by the mixing ratio of the ether compound, the mefenacet, the anilide compound and the thiafluamide, which are the active ingredient compounds, the weather conditions, the formulation, the application time, the application method, the application place, Although it may vary depending on the weeds and crops to be controlled, the total amount of the active ingredient compound per hectare is usually 5 to 2000 g. Emulsions, wettable powders, suspensions and the like are applied by diluting a predetermined amount thereof with water of usually 100 to 1000 liters per hectare, and granules and the like are usually applied without any dilution.

[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, 1 part, mefenacet 50 parts, calcium lignin sulfonate 3 parts, sodium lauryl sulfate 2 parts, and synthetic hydrous silicon oxide 44 parts 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 F, 13 parts, mefenacet 65 parts, calcium lignin sulfonate 3 parts, sodium lauryl sulfate 2 parts, and synthetic hydrous silicon oxide 17 parts were pulverized and mixed well. To obtain a wettable powder. Formulation Example 3 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 1 part, Mefenacet 50 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 43 parts are mixed. ,
The suspension is obtained by grinding until the particle size is less than 5 microns. Formulation Example 4 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 10 parts, Mefenacet 70 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 14 parts are mixed. The suspension is obtained by grinding until the particle size is less than 5 microns. Formulation Example 5 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 1 part, anilide compound, 50 parts, calcium ligninsulfonate, 3 parts, sodium lauryl sulfate, 2 parts and synthetic hydrous silicon oxide, 44 parts, are pulverized and mixed well. To obtain a wettable powder. Formulation Example 6 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 13 parts, anilide compound, 65 parts, calcium ligninsulfonate, 3 parts, sodium lauryl sulfate, 2 parts and synthetic hydrous silicon oxide, 17 parts, are pulverized and mixed well. To obtain a wettable powder. Formulation Example 7 Compound A, Compound B, Compound C, Compound D, Compound E or 1 part of compound F, 50 parts of anilide compound, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 43 parts of water are mixed. And
The suspension is obtained by grinding until the particle size is less than 5 microns. Formulation Example 8 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 10 parts, anilide compound 70 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 14 parts are mixed. Then, the suspension is obtained by grinding until the particle size becomes 5 microns or less. Formulation Example 9 1 part of Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 50 parts of thiafluamide, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 44 parts of synthetic hydrous silicon oxide are crushed and mixed well. To obtain a wettable powder. Formulation Example 10 Compound A, compound B, compound C, compound D, compound E or compound F, 13 parts, thiafluamide 65 parts, calcium ligninsulfonate 3 parts, sodium lauryl sulfate 2 parts, and synthetic hydrous silicon oxide 17 parts are pulverized and mixed well. To obtain a wettable powder. Formulation Example 11 Compound A, compound B, compound C, compound D, compound E or compound F, 1 part, thiafluamide 50 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 43 parts are mixed. And
The suspension is obtained by grinding until the particle size is less than 5 microns. Formulation Example 12 Compound A, Compound B, Compound C, Compound D, Compound E or Compound F, 10 parts, thiafluamide 70 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 14 parts are mixed. Then, the suspension is obtained by grinding until the particle size becomes 5 microns or less.

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 Field soil was packed into a plastic pot having an area of 704 cm ² and a depth of 30.6 cm, and corn and sorghum sorghum were sown. Compound A 5 parts, polyvinyl alcohol 10
A 50% aqueous solution and 45 parts of water are mixed and pulverized to a particle size of 5 microns or less. A suspension of compound A, 5 parts of mefenacet, 50 parts of a 10% aqueous polyvinyl alcohol solution and 45 parts of water are mixed. A predetermined amount of each of a suspension of mefenacet obtained by mixing and grinding to a particle size of 5 μm or less, and a suspension of a mixture of compound A and mefenacet obtained according to Formulation Example 3 is added to water. And sprayed evenly on the soil surface with a small sprayer. The same operation was performed for compound B. After the treatment, the plants were cultivated in a greenhouse, and the safety on corn on the fifth day and the herbicidal efficacy on sorghum on the ninth day were investigated. Table 2 shows the results.

[Table 2] Test Example 2 Field soil was packed in a plastic pot having an area of 704 cm ² and a depth of 30.6 cm, and corn and sorghum sorghum were sown. Compound A 5 parts, polyvinyl alcohol 10
% Aqueous solution and 45 parts of water are mixed and pulverized to a particle size of 5 μm or less, a suspension of compound A, 5 parts of anilide compound, 50 parts of a 10% aqueous solution of polyvinyl alcohol, 45 parts of water And a suspension of an anilide compound obtained by pulverizing the mixture to a particle size of 5 μm or less, and a suspension of a mixture of the compound A and the anilide compound obtained according to Formulation Example 3. The quantitation was diluted with water and evenly sprayed on the soil surface with a small sprayer. The same operation was performed for compound B. After the treatment, the plants were cultivated in a greenhouse, and the safety on corn on the fifth day and the herbicidal efficacy on sorghum on the ninth day were investigated. Table 3 shows the results.

[Table 3]

[0014]

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

Claims (2)

[Claims] (1) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2
-Yl) phenyl C1-C5 acyclic hydrocarbyl ether and 2- (2-benzothiazolyloxy) -N
-Methyl-N-phenylacetamide, 4'-fluoro-N-methyl-2- (5-trifluoromethyl-1,
3,4-thiadiazol-2-yloxy) acetanilide and 4'-fluoro-N-isopropyl-2- (5
-Trifluoromethyl-1,3,4-thiadiazole-
A herbicide composition comprising, as an active ingredient, one selected from the group consisting of 2-yloxy) acetanilide. 2. The herbicidal composition according to claim 1, for controlling weeds in a corn field.