JPH10291908A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject safe composition having high herbicidal effects and a wide weeding spectrum by including a specific phenoxyacetic acid ester derivative and one selected from acifluorfen-sodium, lactofen and fomesafen as active ingredients therein. SOLUTION: This composition is obtained by including 0.5-90 wt.% total amount of 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenoxyacetic acid ester derivative and one selected from the group consisting of a sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, ethyl O-[5-(2- chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoyl]-DL-lactate and 5-[2- chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide 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-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3).
-Pyridazinone-2-yl) phenoxyacetic acid ester derivative and 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoic acid sodium salt (generic name acifluorophen-sodium,
Hereinafter referred to as acifluorophen-sodium), ethyl O- [5- (2-chloro-α, α, α, -trifluoro-p-tolyloxy) -2-nitrobenzoyl] -DL
-Lactate (generic name lactofen, hereinafter referred to as lactofen) and 5- [2-chloro-4- (trifluoromethyl) phenoxy] -N- (methylsulfonyl) -2
A herbicidal composition containing, as an active ingredient, a herbicide composition containing one selected from the group consisting of nitrobenzoamides (generic name fomesafen, hereinafter referred to as fomesafen) as foliage treatment on weeds, so that it can be used on agricultural or non-agricultural lands. Various weeds that occur can be effectively weeded, and their herbicidal efficacy is synergistically increased compared to when they are used alone, can be applied at a low dose, and the herbicidal spectrum is further expanded,
In particular, it has been found that a wide range of weeds can be selectively removed in a soybean field, and the present invention has been achieved. That is, the present invention
1 selected from the group consisting of -chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and acifluorophen-sodium, lactofen and fomesafen Provided is a herbicidal composition for foliage treatment containing a seed as an active ingredient (hereinafter referred to as the composition of the present invention) and a method for foliar application of the composition to weeds.

[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 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone was added to a mixture of 5.3 g (53.3 mmol) of sodium acetate and about 100 ml of water under ice-cooling. 2 at ℃
Stirred for 0 minutes. The reaction was cooled to room temperature and
A solution of 5.8 g (21.5 mmol) of fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the mixture was stirred at room temperature for 1 hour. The ether layer was separated and concentrated, and about 60 ml of tetrahydrofuran (hereinafter referred to as "THF") was added to the residue, and 8.3 g (23.0 mm) of carbethoxyethylidenetriphenylphosphorane was added thereto.
ol) and heated to reflux for 2 hours. After the THF was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography.
To give 3.8 g (10.5 mmol) of 2- [2-fluoro-4-chloro-5-isopropoxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one. 2
3.5 g (9.7 mmol) of-[2-fluoro-4-chloro-5-isopropoxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one was added under ice-cooling to about 10 m of concentrated sulfuric acid.
l and warmed to room temperature. After 10 minutes, about 1
00 ml of water was added, and the resulting crystals were collected by filtration and twice with 20 ml of water.
Washing was sequentially performed once with 10 ml of hexane. The obtained crystals were recrystallized from isopropanol to give 2- [2-fluoro-4
-Chloro-5-hydroxyphenyl] -4-methyl-5
3.2 g of trifluoromethylpyridazin-3-one (9.9 m
mol). 2- [2-fluoro-4-chloro-5-
Hydroxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one 3.2 g (9.9 mmol) in DMF
Dissolve in about 50 ml and add sodium hydride (60 wt%
Add 0.44 g (11 mmol) of oil dispersion and add 30
After leaving at room temperature for 10 minutes, the mixture was cooled on ice, and ethyl bromoacetate (1.8 g, 11 g) was added.
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 purified by silica gel column chromatography.
And ethyl 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetate (hereinafter referred to as compound A).
2.4 g (5.5 mmol) were obtained. Melting point 102.0 ° C

Production Example 2 The same procedure as in Production Example 1 was carried out except that the following reaction reagents were used instead of ethyl bromoacetate, whereby 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.)

[0006] ¹ H-NMR (250 MHz or 300 MHz)
MHz, CDCl 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)

Acifluorophen-sodium is from Farm C
Chemicals Handbook, 1995 (Meister, Publishing
Co., 1995) C55. Lactofen is available from the Farm Chemicals Handbook, 199
5 (Meister, Publishing Co., 1995) C
Compound described on page 93. Fomesafen is Farm C
Chemicals Handbook, 1995 (Meister, Publishing
Co., published in 1995) C177.

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. In particular, major weeds in soybean fields, such as buckwheat, Sanaetada, Sasaetada, Purslane, Shiroza, Aogetou, Noharagarashi, Tsunoxanem, Ebisugusa, Ichibi, American dragon deer, American morning glory, Malva morning glory, Malva American Dicotyledonous plants such as morning glory, artichoke mackerel, dogwood, onamimomi, sunflower, medaka, mulberry, euphorbia americana, ragweed, etc. Yatta - Ke - while effectively herbicidal monocotyledons such emissions, no phytotoxicity, such as a problem with respect to maize crop after soybeans and soybean crop.

In the composition of the present invention, 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative as an active ingredient, The mixing ratio with one selected from the group consisting of phen-sodium, lactofen and fomesafen can vary depending on the target weed species, application scenes, application conditions, and the like, but is usually in the range of 1: 1 to 100 by weight. is there.

[0010] 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 formulation, etc., to form an emulsion, a wettable powder, a suspension and the like. It is used after conversion. In these formulations, 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-
The total amount of the 3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and one selected from the group consisting of acifluorophen-sodium, lactofen and fomesafen is generally 0.5 to 90% by weight, preferably 1 to 8% by weight.
0% by weight is contained.

[0011] The solid carrier used in the preparation includes, for example, clays (kaolinite, diatomaceous earth, synthetic hydrous silicon oxide, fubasamikure, bentonite, acid clay, etc.), talc, and other inorganic minerals (sericite, quartz) Powder, sulfur powder, activated carbon, calcium carbonate, etc.) and fine powders and granular materials such as chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, salt ammonium salt, urea, etc.). Examples of the liquid carrier include water, alcohol and the like. (E.g., methanol, ethanol), ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, methylnaphthalene), non-aromatic hydrocarbons (e.g., hexane, cyclohexane) , Kerosene, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile) Le etc.), e - ethers (dioxane, diisopropyl et - ether, etc.), 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, and polyethylene glycol ethers.
Examples include ters, polyhydric alcohol esters, and sugar alcohol derivatives. Other formulation aids include:
For example, fixing 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.). And dispersant, PAP (isopropyl 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.

The composition of the present invention can also be prepared by formulating each of the active ingredients 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: 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester which is an active ingredient compound. A mixture of a derivative and one selected from the group consisting of acifluorophen-sodium, lactofen and fomesafen, weather conditions, formulation, application time, application method, application place, weeds to be controlled,
Although it may vary depending on the target crop, the total amount of the active ingredient compound per hectare is usually 10 to 200 g.
Emulsions, wettable powders, suspensions and the like are applied by diluting a predetermined amount thereof with 100 to 1,000 liters of water per hectare.

[0015]

[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,
10 parts of compound K, compound L, compound M or compound N, 50 parts of lactofen, calcium ligninsulfonate 3
Parts, 2 parts of sodium lauryl sulfate and 35 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,
5 parts of compound K, compound L, compound M or compound N, 70 parts of acifluorfen-sodium, 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 form a wettable powder. obtain. Formulation Example 3 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, 70 parts of fomesafen, calcium ligninsulfonate 3
Parts, 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 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, 25 parts of lactofen, 3 parts of polyoxyethylene sorbitan monooleate, CMC (carboxymethyl cellulose)
3 parts and 64 parts of water are mixed and wet-ground to a particle size of 5 microns or less to obtain a suspending agent. 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 N2 parts, acifluorfen-sodium 30 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose) 3 parts and water 62 parts are mixed. And wet pulverization until the particle size becomes 5 microns or less to obtain a suspension. 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, Fomesafen 30 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethyl cellulose-
S) 3 parts and 64 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspending agent.

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.times.19 cm.sup.2 and a depth of 7 cm was filled with field soil and soybean, Aquino nokorogosa,
The crabgrass was sowed and grown in a greenhouse for 23 days. Compound A 10 parts, polyoxyethylene styryl phenyl ether 14 parts, calcium dodecylbenzenesulfonate 6
A, a lactofen preparation (trade name: Cobra: manufactured by Verent) and a mixture of the compound A emulsion and the lactofen preparation obtained by thoroughly mixing 35 parts of xylene and 35 parts of cyclohexanone. A predetermined amount of each was diluted with water, and sprayed uniformly from above the plant with a small sprayer. The plants were grown in a greenhouse for 4 days after the treatment, and the herbicidal efficacy and the safety against soybean were investigated. In addition, the same test was performed for compound E. Table 2 shows the results.

[Table 2]

Test Example 2 Field soil was filled in a plastic pot having an area of 26.5 × 19 cm ² and a depth of 7 cm, soybean, Aquino edulis,
The crabgrass and rice millet were sowed and grown in a greenhouse for 23 days. An emulsion of compound A obtained by thoroughly mixing 10 parts of compound A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, an acifluorfen-sodium preparation (product) First name Blaze
r: BASF), fomesafen preparation (brand name R)
eflex: manufactured by Zeneca Ag Products), Compound A
And acifluorfen-sodium preparations,
A predetermined amount of each of the mixture of the compound A and the fomesafen preparation was diluted with water, and the mixture was uniformly sprayed from above the plant with a small sprayer. The plants were grown in a greenhouse for 5 days after the treatment, and their herbicidal efficacy and safety against soybean were investigated. Table 3 shows the results.

[Table 3]

[0020]

EFFECT OF THE INVENTION By using the composition of the present invention, a wide range of weeds in a soybean field, particularly in a soybean field, can be selectively removed.

Claims (4)

[Claims] (1) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2)
-Yl) phenoxyacetic acid ester derivative and 5- [2-
Chloro-4- (trifluoromethyl) phenoxy] -2
-Nitrobenzoic acid sodium salt, ethyl O
-[5- (2-chloro-α, α, α, -trifluoro-
p-tolyloxy) -2-nitrobenzoyl] -DL-
Lactate and 5- [2-chloro-4- (trifluoromethyl) phenoxy] -N- (methylsulfonyl)-
A herbicidal composition for foliage treatment comprising, as an active ingredient, one selected from the group consisting of 2-nitrobenzoamide. 2. The herbicidal composition according to claim 1, for controlling weeds in a soybean field. (3) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2)
-Yl) phenoxyacetic acid ester derivative and 5- [2-
Chloro-4- (trifluoromethyl) phenoxy] -2
-Nitrobenzoic acid sodium salt, ethyl O
-[5- (2-chloro-α, α, α, -trifluoro-
p-tolyloxy) -2-nitrobenzoyl] -DL-
Lactate and 5- [2-chloro-4- (trifluoromethyl) phenoxy] -N- (methylsulfonyl)-
A herbicidal method characterized by treating a weed with foliage using a herbicide containing, as an active ingredient, one selected from the group consisting of 2-nitrobenzoamide. 4. A method for treating weeds in a soybean field.
The method for weeding described in 1.