JP2000053509A - Herbicide composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicide composition having excellent herbicidal effects. SOLUTION: This herbicidal composition for treating leaves and stalks contains a 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenoxyacetic acid ester derivative and one compound selected from the group consisting of 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione, 2-(4-mesyl-2- nitrobenzoyl)cyclohexane-1,3-dione, 5-cyclopropyl-4-(2-methylsulfonyl-4- trifluoromethylbenzoyl)isoxazole and 4-chloro-2-mesylphenyl 5- cyclopropyl-1,2-oxazol-4-yl ketone as effective ingredients.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a herbicidal composition for foliage treatment and a method for foliar application of the composition to weeds.

[0002]

2. Description of the Related Art At present, many herbicides are commercially available and used. However, since many kinds of weeds are to be controlled and their occurrence is long-term, more effective herbicidal effects are obtained. There is a need for a herbicide that has a high herbicide spectrum, a broad herbicidal spectrum, and does not cause phytotoxicity problems for crops.

[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, 2- (2-chloro-4-mesylbenzoyl) cyclohexane-1,3-dione (generic name sarcotrione, hereinafter referred to as sarcotrione), 2- (4-mesyl-2-nitrobenzoyl) cyclohexane-1,3-dione (mesotrione, hereinafter referred to as mesotrione), 5
-Cyclopropyl-4- (2-methylsulfonyl-4
-Trifluoromethylbenzoyl) isoxazole (generic name isoxaflutol, hereinafter referred to as isoxaflutol) and 4-chloro-2-mesylphenyl 5-cyclopropyl-1,2-oxazol-4-yl ketone (general A name of isoxacrotol, hereinafter referred to as isoxacrotol) is used as an active ingredient in a herbicidal composition containing as an active ingredient a foliage treatment of weeds, thereby cultivating land or non-agricultural land. 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 weeded in corn and soybean fields, and have reached the present invention. That is, the present invention relates to 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative, sarcotrione, mesotrione,
Herbicide composition for foliage treatment (hereinafter, referred to as the composition of the present invention) containing, as an active ingredient, one selected from the group consisting of isoxaflutol and isoxacrotol, and foliar treatment of the herbicide on weeds. Provide a weeding method.

[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) was added to N, N
-Dissolve in about 50 ml of dimethylformamide and add 0.44% sodium hydride (60% by weight oil dispersion) at room temperature.
g (11 mmol), leave at room temperature for 30 minutes, cool on ice,
1.8 g (11 mmol) of ethyl bromoacetate were added. After stirring at room temperature for 1 hour, diethyl ether and water were sequentially added and extracted. The organic layer was washed successively with 10% aqueous hydrochloric acid, a saturated aqueous solution of sodium bicarbonate 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-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-
2.4 g (5.5 mmol) of ethyl 3-pyridazinone-2-yl) phenoxyacetate (hereinafter referred to as compound A) was 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 (1H, d, J = 7 Hz), 7.33 (1H,
d, J = 8 Hz), 7.99 (1 H, s) Compound H: 1.26 (6 H, d, J = 6.3 Hz),
2.43 (3H, q, J = 2 Hz), 4.65 (2H,
s), 5.05-5.18 (1H, m), 6.98 (1
H, d, J = 7 Hz), 7.33 (1H, d, J = 8H)
z), 7.98 (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 = 6.3 Hz), 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 (1H, m), 7.96-8.00 (1H,
m) Compound K: 1.5-1.9 (8H, m), 2.43 (3
H, q, J = 2 Hz), 4.65 (2H, s), 5.2
−5.4 (1H, m), 6.97 (1H, d, J = 7H)
z), 7.33 (1H, d, J = 8 Hz), 7.98
(1H, 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 (1H, 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), 4.94-5.01 (1H, m), 7.03 (1
H, d, J = 6.3 Hz), 7.26-7.31 (1
H, m), 7.34 (1H, d, J = 9.0 Hz),
7.99 (1H, s)

[0007] Sarcotrione is obtained from Farm Chemicals Handboo.
k, 1998 (Meister, Publishing Co., 19
98) C263. Mesotrione is available from AGROW 1998 (No296 January)
16th, 1998), p. 22.
Isoxaflutol is AG CHEM NEW COMP
OUND REVIEW, VOLUME 15, 1997
Year (AG CHEM INFORMATION SERV
ICES), page 44. Isoxacrotol is available from AGROW 1998 (No296 Janu).
ry 16th, 1998) p.22.

The composition of the present invention has a herbicidal activity against a wide range of weeds and has a high selectivity to crops. In addition to ordinary tillage cultivation, no-tillage cultivation, orchards and other agricultural and horticultural fields. It also has excellent herbicidal activity on non-cultivated lands such as athletic fields, vacant lots, forest lands, and track ends, and is therefore excellent as a herbicide. That is, the composition of the present invention has a herbicidal effect on the following various weeds which are problematic in corn, soybean, wheat, rice fields and the like. Polygonum weed: Polygonum con
volvulus), Polygonum (Polygonum)
lapathifolium), Polygonum pensylvanicu
m), Hartade (Polygonum persica)
ria), Rumex crisp
s), Rumex obtusifo (Rumex obtusifo)
lius) and knotweed (Polygonum csp)
idatum) Purslanaceae Weed: Purslane (Portulaca)
oleracea) Weeds: Stellaria med
ia) Chenopodium weed: Shiroza (Chenopodium al
bum), Butterfly (Kochia scopari)
a) Amaranthaceae weed: Amaranthus r
etroflexus)
lanthus hybridus Brassicaceae Weed: Wild Radish (Raphan)
us raphanistrum)
inapis arvensis, Capsicum (Caps)
ella bursa-pastoris Legume weed: American hornbrush (Sesbania)
exaltata), Ebisugusa (Cassia ob)
tusifolia), Florida Vega Weed (De)
smodium tortuosum, white clover (Trifolum repens) Malvaceae weed: Abutilon theop
hrusti), American deer (Sida sp.)
inosa) Violet weeds: Field panji (Viola ar)
vensis), Wild Panji- (Viola tr)
icor) Rubiaceae Weed: Gallium apari
ne) Convolvulaceae weed: American morning glory (Ipomoea)
hederacea), Malva Asagao (Ipomoe)
a purpura), Malva American morning glory (I
pomoea hederacea var integ
riuscula) and bean sagao (Ipomoea)
lacunosa), Convolvulus convolvulus (Convol)
vulus arvensis Lamiaceae Weeds: Lameur pur
puree), Photohenosa (Lamium ampl)
exicaule) Solanaceae weeds: Datura japonicus (Data)
a Stramonium), Dog Physalis (Sola)
num nigrum Scrophulariaceae Weed: Veronica
ca persica), scorpion (Veroni)
ca hederaefolia Asteraceae Weed: Xanthium pensy
lvanicum), wild sunflower (Helianth)
us annuus), dog chamomile (Matrica)
ria performata or inodora),
Common Gold (Chrysanthemum)
segetum), oro-shag (Matricari)
a matricarioides), Ragweed (Am)
brosia artemisiifolia, oobtaxa (Ambrosia trifidida), and swordweed (Erigeron canadensi)
s), mugwort (Artemisia print)
s), Solidago alga (Solidago al)
tissima) Purple weed: Forget-me-not (Myosotis a)
Ravensis (Coleoptera: Chrysomelidae): Asclepias
syriaca spurges weed: Euphorbi
a helioscopia), Onishikisou (Eu)
phorbia maculata Grass weed: Echinochloa cr
us-galli), Enokorogosa (Setaria)
viridis), Aquinoe nokorogosa (Setari)
a faberi), Meishishiba (Digitalias)
anguinalis), Hawkgrass (Eleusine)
indica), Poa annua (Poa annu)
a), Blackgrass (Alopecurus myo)
suloides), oats (Avena fat)
ua), Sorghum sorghum (Sorghum hale)
pense), barley (Agropyron rep)
ens), Umanohashiki (Bromus tecto)
rum), Cynodone dact (Cynodone dact)
ylon), cane millet (Panicum dich)
otomiflorum), Texas honeycomb (Pan)
icum texanum), Shata cane (Sor
ghum vulgare Cyperaceae Weed: Commelina co
mmunis) Rhododendron weeds: horsetail (Equisetum arve)
nse) Cyperaceae Weeds: Cygous cyperus (Cyperus)
iria), nectarine (Cyperus rotund)
us), yellowtail sedge (Cyperus esculen)
tus) On the other hand, the composition of the present invention does not cause harmful effects on crops such as corn, soybean, wheat and rice.

[0009] The composition of the present invention can be prepared by using known breeding methods or genetic engineering techniques or the like to obtain p-proteins such as sarcotrione, mesotrione, isoxaflutole and isoxacrotol.
-Hydroxyphenylpyruvate dioxygenase (p
-Hydroxyphenylpyruvate di
Oxygenase (hereinafter referred to as HPPD)) does not cause harmful injury to crops given resistance to inhibitory herbicides. A method for genetically producing a crop having resistance to an HPPD-inhibiting herbicide is described in detail in WO96 / 38567 and the like.

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 and sarcotrione The mixing ratio with one selected from the group consisting of, mesotrione, isoxaflutole and isoxacrotol can vary depending on the target weed species, application scenes, application conditions, etc., but usually the following weight ratios are used. It is. 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3
The mixing ratio of -pyridazinone-2-yl) phenoxyacetic acid ester derivative and sarcotrione is in the range of 1: 2 to 200, and 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl- 3-pyridazinone-2
The mixing ratio of -yl) phenoxyacetic acid ester derivative to mesotrione, isoxaflutole or isoxacrotol is in the range of 1: 0.5 to 50.

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, and the like, to prepare emulsions, wettable powders, suspensions and granules. Etc. and used as a formulation. In these formulations, 2-chloro-
Selected from the group consisting of 4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and sarcotrione, mesotrione, isoxaflutol and isoxacrotol 0.5 to 90% by weight,
Preferably, it is contained in an amount of 1 to 80% by weight.

[0012] The solid carrier used in the preparation includes, for example, clays (kaolinite, diatomaceous earth, synthetic hydrated 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, sugars and the like. 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.

The composition of the present invention can also be prepared by formulating the respective 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 when used in combination with other herbicides, and further, insecticides, fungicides, plant growth regulators, fertilizers, safeners, and soil improvement. It can also be used in combination with agents and the like.

The application rate of the composition of the present invention is determined by controlling the amount of the active ingredient compound, 2-chloro-4-fluoro-5- (4-methyl-
A mixing ratio of 5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and one selected from the group consisting of sarcotrione, mesotrione, isoxaflutole and isoxacrotol, weather conditions, The total amount of the active ingredient compound per hectare is as follows, although it may vary depending on the formulation form, application time, application method, application place, weeds to be controlled and target crops.
The total amount of 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and sarcotrione is usually 40 to 8000 g per hectare, preferably. Is 100 to 4000 g, and 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative, mesotrione, isoxaflutole or The total amount with Xacactol is 10-200 per hectare
0 g, preferably 10 to 1000 g. Emulsions, wettable powders, suspending agents and the like are usually used in a predetermined amount per hectare.
Dilute with 00-1000 liters of water and apply.

[0016]

[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,
Compound K, Compound L, Compound M or Compound N4 parts, sarcotrione 80 parts, calcium ligninsulfonate 3
Parts, 2 parts of sodium lauryl sulfate and 11 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,
0.5 parts of compound K, compound L, compound M or compound N,
50 parts of sarcotrione, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 44.5 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,
Compound F, Compound G, Compound H, Compound I, Compound J,
Compound K, Compound L, Compound M or Compound N5 parts, sarcotrione 25 parts, calcium ligninsulfonate 3
Parts, sodium lauryl sulfate 2 parts and synthetic hydrous silicon oxide 65 parts are sufficiently 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,
3 parts of compound K, compound L, compound M or compound N, 60 parts of sarcotrione, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 31 parts of water are mixed, and the particle size becomes 5 microns or less. To obtain a suspension. Formulation Example 5 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,
A suspension is obtained by mixing 50 parts of sarcotrione, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 43.5 parts of water, and wet-grinding the mixture until the particle size becomes 5 microns or less. Formulation Example 6 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, 5 parts of sarcotrione, 3 parts of polyoxyethylene sorbitan monooleate, CMC (carboxymethyl cellulose)
3 parts and 88 parts of water are mixed and wet-ground to a particle size of 5 microns or less to obtain a suspending agent.

Formulation Example 7 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
14 parts of compound K, compound L, compound M or compound N, 70 parts of mesotrione, calcium ligninsulfonate 3
Parts, 2 parts of sodium lauryl sulfate and 11 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 8 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, mesotrione 40 parts, calcium ligninsulfonate 3 parts,
2 parts of sodium lauryl sulfate and synthetic hydrous silicon oxide 5
3 parts are pulverized and mixed to obtain a wettable powder. Formulation Example 9 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, 10 parts of mesotrione, calcium ligninsulfonate 3
Parts, 2 parts of sodium lauryl sulfate and 75 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder.

Formulation Example 10 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), mesotrione (50 parts), polyoxyethylene sorbitan monooleate (3 parts), CMC (carboxymethylcellulose) (3 parts) and water (34 parts) are mixed until the particle size becomes 5 microns or less. The suspension is obtained by wet grinding. Formulation Example 11 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
1.5 parts of compound K, compound L, compound M or compound N,
30 parts of mesotrione, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 62.5 parts of water are mixed and wet-pulverized until the particle size becomes 5 μm or less to obtain a suspending agent. Formulation Example 12 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, Mesotrione 2 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethylcellulose) 3
And 90 parts of water are mixed and wet milled until the particle size is 5 microns or less to obtain a suspending agent.

Formulation Example 13 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
14 parts of compound K, compound L, compound M or compound N, 70 parts of isoxaflutol, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 11 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. . Formulation Example 14 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 2 parts, isoxaflutole 40 parts, lignin sulfonate calcium 3 parts, sodium lauryl sulfate 2 parts and synthetic hydrous silicon oxide 53 parts are pulverized and mixed to obtain a wettable powder. . Formulation Example 15 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, 10 parts of isoxaflutol, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 75 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. .

Formulation Example 16 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), isoxaflutole (50 parts), polyoxyethylene sorbitan monooleate (3 parts), CMC (carboxymethyl cellulose) 3 parts and water 34 parts are mixed, and the particle size is 5 microns or less. To obtain a suspension. Formulation Example 17 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
1.5 parts of compound K, compound L, compound M or compound N,
A mixture of 30 parts of isoxaflutol, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 62.5 parts of water has a particle size of 5 parts.
The suspension is obtained by wet milling to submicron size. Formulation Example 18 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, isoxaflutole 2 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethylcellulose) 3 parts and water 90 parts are mixed, and the particle size is 5 microns or less. To obtain a suspension.

Formulation Example 19 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
14 parts of compound K, compound L, compound M or compound N, 70 parts of isoxacrotol, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 11 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. . Formulation Example 20 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, isoxacrotol 40 parts, lignin sulfonate calcium 3 parts, sodium lauryl sulfate 2 parts and synthetic hydrous silicon oxide 53 parts are pulverized and mixed to obtain a wettable powder. . Formulation Example 21 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, 10 parts of isoxacrotol, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 75 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. .

Formulation Example 22 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), isoxacrotol (50 parts), polyoxyethylene sorbitan monooleate (3 parts), CMC (carboxymethyl cellulose) 3 parts and water 34 parts are mixed, and the particle size is 5 microns or less. To obtain a suspension. Formulation Example 23 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
1.5 parts of compound K, compound L, compound M or compound N,
A mixture of 30 parts of isoxacrotol, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 62.5 parts of water, having a particle size of 5
The suspension is obtained by wet milling to submicron size. Formulation Example 24 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, isoxacrotol 2 parts, polyoxyethylene sorbitan monooleate 3 parts, CMC (carboxymethylcellulose) 3 parts and water 90 parts are mixed, and the particle size is 5 microns or less. To obtain a suspension.

Test examples are shown below. Evaluation criteria The herbicidal efficacy was evaluated as “0” when the growth state of the test weed at the time of the survey was no or little different from that of the untreated plant, and the test plant completely died or completely grown. Suppressed ones are defined as “10”, and 1 of 0-10
Classify in one stage, 0, 1, 2, 3, 4, 5, 6, 7,
Shown at 8, 9, 10. Evaluation value of herbicidal efficacy "7",
“8”, “9” and “10” mean that the herbicidal effect is excellent, and an evaluation value “5” or less means that the herbicidal effect is insufficient for practical use. 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 a diameter of 14 cm and a depth of 12.5 cm was filled with field soil, and corn and crabgrass were sown.
Maize was grown in a greenhouse for 14 days and crabgrass for 21 days. An 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, a sarcotrione preparation (trade name: Mikado, Selling agency:
(Zeneca agrochemicals) and a predetermined amount of each of the mixture of the compound A emulsion and the sarcotrione preparation were diluted with water, and sprayed evenly from above the plants with a small sprayer. The plants were grown in a greenhouse for 4 days after the treatment, and the herbicidal efficacy and safety to corn were investigated. Table 1 shows the results.

[Table 2]

Test Example 2 A field pot was filled with plastic soil in a plastic pot having a diameter of 14 cm and a depth of 12.5 cm, sowed with crabgrass, and grown in a greenhouse for 21 days. An 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,
An isoxaflutole emulsion obtained by well mixing 10 parts of isoxaflutol, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone, and the compound A emulsion. A predetermined amount of each of the mixture with the isoxaflutole emulsion 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 3]

[0027]

Industrial Applicability By using the composition of the present invention, a wide range of weeds in a corn field, a soybean field, a wheat field, a rice field, etc. can be selectively removed.

Claims (2)

[Claims] (1) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2)
-Yl) phenoxyacetic acid ester derivative and 2- (2-
Chloro-4-mesylbenzoyl) cyclohexane-1,
3-dione, 2- (4-mesyl-2-nitrobenzoyl) cyclohexane-1,3-dione, 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethylbenzoyl) isoxazole and 4- Chloro-
A herbicide composition for foliage treatment comprising, as an active ingredient, one selected from the group consisting of 2-mesylphenyl 5-cyclopropyl-1,2-oxazol-4-yl ketone. 2. A method for herbicidal treatment comprising subjecting a weed to foliage treatment with the herbicidal composition according to claim 1.