WO2007132703A1

WO2007132703A1 - Herbicidal composition

Info

Publication number: WO2007132703A1
Application number: PCT/JP2007/059560
Authority: WO
Inventors: Hajime Ikeda; Satoru Kizawa
Original assignee: Sumitomo Chemical Company, Limited
Priority date: 2006-05-17
Filing date: 2007-04-27
Publication date: 2007-11-22
Also published as: CL2007001396A1; JP2007308400A

Abstract

An object of the present invention is to provide a method for controlling a wide variety of weeds with higher herbicidal activity without significant phytotoxicity to crops, and the present invention provide a herbicidal composition comprising [a] 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-ylsulfonyl)urea and [b] a compound represented by the formula (II): as active ingredients, which can be effectively used particularly in crop fields.

Description

DESCRIPTION HERBICIDAL COMPOSITION

Technical Field The present invention relates to a herbicidal composition.

Background Art

At the present time, many herbicides are commercially available and used (see, e.g., Crop Protection Handbook,

Vol.89 (2003), Meister Publishing Company, ISBN: 1-892829- 06-1) . There are, however, many species of weeds to be controlled and their growth extends over a long time. For this reason, requested are herbicides having higher herbicidal activity, a wider herbicidal spectrum, and no problem for phytotoxicity to crops.

•Disclosure of Invention

An object of the present invention is to provide a method for controlling a wide variety of weeds with higher herbicidal activity without significant phytotoxicity to crops, and the like.

The present inventors studied intensively under the circumstances, and as a result, accomplished the present invention. That is, the present invention provides: 1. A herbicidal composition which comprises: [a] 1- (4, β-dimethoxypyrimidin-2-yl) -3- (2- ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea, and [b] a compound represented by the formula (II) :

as active ingredients (hereinafter, referred to as the composition of the present invention) ;

2. A herbicidal composition for controlling weeds in crop fields which comprises [a] 1- (4, 6-dimethoxypyrimidin-2-yl) - 3- (2-ethylsulfonylimidazo [1, 2-a]pyridin-3-ylsulfonyl) urea and [b] a compound represented by the formula (II) as active ingredients, wherein the weight ratio of [a] ^' : [b] is from 1:0.1 to 1:10; 3. A method for controlling weeds in crop fields which comprises applying [a] 1- (4, 6-dimethoxypyrimidin-2-yl) -3- ( 2-ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea and [b] a compound represented by the formula (II) in combination as a mixture or separate compositions, to weeds or to soil in 'a place where weeds grow or will grow;

4. A method for controlling weeds in crop fields which comprises applying [a] 1- (4, 6-dimethoxypyrimidin-2-yl) -3- (2-ethylsulfonylimidazo[l, 2-a]pyridin-3-ylsulfonyl) urea and [b] a compound represented by the formula (II) in combination as a mixture or separate compositions, wherein the weight ratio of [a] : [b] is from 1:0.1 to 1:10, to weeds or to soil in a place where the weeds grow or will grow; and

5. Use of a combination of [a] 1- (4, 6-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a]pyridin-3- ylsulfonyl) urea and [b] a compound represented by the formula (II) as active ingredients of a herbicidal composition for controlling weeds in crop fields.

According to the present invention, a wide variety of weeds in crop fields can be controlled by applying a small amount of the herbicidal composition.

Mode for Carrying Out the Invention

In the present invention, 1- (4, 6-dimethoxypyrimidin-2- yl) -3- (2-ethylsulfonylimidazo [1, 2-a]pyridin-3- ylsulfonyl) urea is a compound represented by the formula (I):

(I) (hereinafter, referred to as the compound 1) and has a generic name, sulfosulfuron (CAS RN 141776-32-1) . The compound 1 can be prepared according to a known method described in USP-5534482, or is commercially available. The compound represented by the above formula (II) (hereinafter, referred to as the compound 2) can be prepared according to a known method described in EP- 1466527.

The composition of the present invention can effectively control annual and perennial weeds growing in crop fields, including wild oat (Avena fatua) , downy brome (Bromus tectorum) , poverty brome (Bromus sterilis) , cheat (Bromus secalinus) , blackgrass (Alopecurus myosuroides) , littleseed canarygrass (Phalaris minor) , loose silkybent (Apera spica-venti) , quackgrass (Agropyron repens), johnsongrass (Sorghum halepense) , barnyardgrass (Echinochloa crus-galli) , catchweed bedstraw (Galium spurium) , wild mustard (Sinapis arvensis) , Indian mustard ■ (Brassica juncea) , common chickweed (Stellaria media) , wild chamomile (Matricaria chamomilla) , ipomoea, amaranthus, polygonum, velvetleaf (Abutilon theophrasti) , common cocklebur (Xanthium strumarium) , common ragweed (Ambrosia artemisiifolia) , dandelion (Taraxacum officinale) , purple nutsedge (Cyperus rotundus) and yellow nutsedge (Cyperus esculentus). Further, the composition of the present invention has high safety (low phytotoxicity) to field crops, particularly to Triticeae crops such as wheat.

The composition of the present invention may take the forms for conventional agricultural chemicals. In other words, the composition of the present invention may take the forms of formulations such as emulsifiable concentrate, oil, spray, wettable agent, powder, DL (driftless) powder, granule, fine-granule, fine-granule F, flowable formulation, JUMBO-formulation, tablet and the like, which can be prepared by dissolving or dispersing the active ingredients in a suitable liquid carrier, mixing the active ingredients with a suitable solid carrier, or adsorbing the active ingredients to a suitable solid carrier. Such formulations may further contain, if necessary, an emulsifier, a dispersant, a spreading agent, a penetrating agent, a wetting agent, a thickening agent, a stabilizer, and the like, and can be prepared by a method known per se.

Examples of a liquid carrier (solvent) that may be used for preparing the composition of the present invention include water, alcohols (e.g. methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, etc.), ketones (e.g. acetone, methyl ethyl ketone, etc.), ethers (e.g. dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (e.g. kerosene, fuel oil, machine oil, etc.) , aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (e.g. dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (e.g. dimethylformamide, dimethylacetamide, etc.), esters (e.g. ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), and nitriles (e.g. acetonitrile, propionitrile, etc.), one or more of which may be used alone or as a mixture in a suitable ratio. Examples of a solid carrier (diluent/bulking agent) that may be used for preparing the composition of the present invention include vegetable powders (e.g. soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powders (e.g. clays such as kaolin, bentonite, acid terra alba, and clay; talcs such as talcum powder and agalmatolite powder; silicas such as kieselguhr and mica powder, etc.), alumina, sulfur powder, and activated carbon, one or more of which may be used alone or as a mixture in a suitable ratio. The liquid or solid carrier can be used usually in an amount of about 1 to 99% by weight, preferably about 1 to 80% by weight of the total weight of the composition of the present invention.

A surfactant may be used as an emulsifier, a spreading agent, a penetrating agent, a dispersant or the like for preparing the composition of the present invention. Examples of such a surfactant include soaps, nonionic and anionic surfactants, for example, polyoxyethylene alkyl aryl ethers (e.g. NOIGEN EA142, manufactured by Dai-Ichi Kogyo Seiyaku Co., Ltd.), polyoxyethylene aryl ethers (e.g. NONAL, manufactured by Toho Chemical Industry Co., Ltd.), alkyl sulfates (e.g. EMAL 10, EMAL 40, manufactured by Kao Corporation), alkyl sulfonates (e.g. NEOGEN, NEOGEN T, manufactured by Dai-Ichi Kogyo Seiyaku Co., Ltd.; and NEOPELEX, manufactured by Kao Corporation) , polyethylene glycol ethers (e.g. NONIPOL 85, NONIPOL 100, NONIPOL 160, manufactured by Sanyo Chemical Industries Ltd. ) , and polyhydric alcohol esters (e.g. Tween 20, Tween 80, manufactured by KAO Corporation) . The surfactant can be used usually in an amount of about 0.1 to 50% by weight, preferably about 0.1 to 25% by weight of the total weight of the composition of the present invention.

When the composition of the present invention is an emulsifiable concentrate, a wettable agent or the like, it preferably comprises the compound 1 and the compound 2 in a total amount of about 1 to 90% by weight. When the composition of the present invention is an oil, a powder, a DL (driftless) powder or the like, it preferably comprises the compound 1 and the compound 2 in a total amount of about 0.01 to 10% by weight. When the composition of the present invention is a fine granule F, a granule or the like, it preferably comprises the compound 1 and the compound 2 in a total amount of about 0.05 to 10% by weight.

When the composition of the present invention is an emulsifiable concentrate, a wettable agent or the like, it is used after diluted with water or the like (e.g., 100 to 100,000 times) as appropriate.

The composition of the present invention can effectively control weeds in crop fields, particularly fields of Triticeae crops (e.g., wheat and the like). The composition of the present invention is usually used as a preemergence soil herbicide or postemergence foliar herbicide in crop fields. The composition of the present invention causes no phytotoxicity to crops, and therefore can be used safely. The application amount of the herbicidal composition of the present invention varies depending on climatic conditions, application timings and application methods, weeds to be controlled, crops to be protected. When the herbicidal composition of the present invention is used in crop fields, the application amount is generally around 30 g to 2000 g, preferably around 50 g to 1000 g of the active ingredients (the total amount of the compound 1 and the compound 2) per hectare.

In the composition of the present invention, the mixing ratio of the compound 1 to the compound 2 that are used as active ingredients is usually 1:0.01 to 100, preferably 1:0.1 to 10, and more preferably 1:1 to 10 by weight.

The composition of the present invention may be prepared by formulating respective active ingredients into separate compositions according to the above-described procedure and then mixing them.

The composition of the present invention can be used in admixture with other herbicides if necessary. The composition of the present invention can also be used together with an insecticide, a bactericide, a plant growth regulator, a fertilizer, a phytotoxicity-reducing agent, a soil conditioner, or the like.

The method for controlling weeds in crop fields of the present invention can be performed by applying a formulation containing the compound 1 and the compound 2 as described above to weeds or soil in crop fields.

Alternatively, the method for controlling weeds in crop fields of the present invention may be performed by applying a formulation containing the compound 1 and a formulation containing the compound 2 in combination to weeds or soil in crop fields.

Examples The present invention is further described in detail by reference to the following Examples including Formulation Examples and Test Examples, which are not intended to restrict the present invention. In Examples, the term "part(s)" means "part(s) by weight".

Formulation Example 1

In a small kneader, 1.0 part of the compound 1, 1.0 part of the compound 2, 0.5 part of NEOCOL YSK (trade name, dialkylsulfosuccinate salt surfactant), 2.0 parts of TOXANON GR31A (trade name, polycarboxylic acid surfactant) , 30.0 parts of KUNIGEL Vl (trade name, bentonite) and 65.5 parts of calcium carbonate are placed, mixed and kneaded. The mixture is granulated with an extrusion type granulator (RG-5M, manufactured by Kikusui Seisakusho Ltd. ) , dried with a fluidized bed dryer (MDB-400, manufactured by Fuji

Paudal Co., Ltd.), and then sieved through a 16- to 48-mesh to prepare a granule.

Formulation Example 2 A mixture of 1.9 parts of the compound 1, 1.9 parts of the compound 2, 9.0 parts of ethylene glycol, 0.3 part of ANTIFOAM E-20 (trade name, silicone emulsion), 0.1 part of sorbic acid, 10.0 parts of ISOELEAT L (trade name, maltosylcyclodextrin) , 3.0 parts of NEWKALGEN D-1518 (trade name, polyoxyethylene oleyl ether) and 2.0 parts of AGRISOL FL-2017 (trade name, polyoxyethylenearyl sulfate) is dispersed in 71.8 parts of water with a homomixer. The mixture thus obtained is subjected to wet grinding (1 pass) with a Dyno-mill (manufactured by Shinmaru Enterprises Corporation, 1.0 mm glass beads, filling rate: 85%, rotating rate: 10 m/s) to prepare a flowable formulation.

Formulation Example 3

To a mixture of 2.4 parts of the compound 1, 2.4 parts of the compound 2, 2.4 parts of MICROSPHERE F-80E (trade name, a hollow plastic' product), 3.0 parts of OLFINE ElOlO (trade name, acetylenediol/acetylene glycol), 2.0 parts of TOXANON GR-31A (trade name), 5.0 parts of sodium tripolyphosphate, 3.0 parts of CELLOGEN 7A (trade name, sodium carboxymethylcellulose) , 10.0 parts of KUNIGEL Vl

(trade name) and 69.8 parts of calcium carbonate is added a predetermined amount of water, and then kneaded. The mixture thus obtained is kneaded and then granulated with an extrusion type granulator (RG-5M, manufactured by Kikusui Seisakusho Ltd) equipped with a 1.5 mm screen, and then dried with a fluidized bed dryer (MDB-400, manufactured by Fuji Paudal Co., Ltd.) to prepare a granule,

Test Example 1: herbicidal effect on wild mustard (pot test in greenhouse) Plastic pots each having a size of 590 cm² x 8 cm were filled with steam sterilized soil. Seeds of wild mustard were sown in the pots and covered with soil of 1 cm thickness . A sulfosulfuron granular wettable agent (a granular wettable agent containing 80% of the compound 1; trade name: Monitor 80 granular wettable agent, manufactured by Monsanto) was diluted with water to prepare a dilution containing the compound 1. The compound 2 was dissolved in acetone containing 2% (W/V) of Tween 20 (surfactant), and then diluted with water so that the concentration of acetone in the resulting dilution is 10% to prepare a dilution containing the compound 2. In addition, a sulfosulfuron granular wettable agent (a granular wettable agent containing 80% of the compound 1; trade name: Monitor 80 granular wettable agent, manufactured by Monsanto) and a solution of the compound 2 in acetone containing 2% (W/V) of Tween 20 (surfactant) were mixed and diluted in a predetermined ratio to prepare a dilution containing the compound 1 and the compound 2. Each 500 L/ha of the dilutions thus obtained were sprayed onto the soil surface in the pots in which seeds of wild mustard were sown, immediately after sowing, so that the drug amounts listed in Table 1 were applied. Three weeks after the application, herbicidal effects of the dilutions on wild mustard were evaluated (herbicidal effect 0% indicates "no effect", and herbicidal effect 100% indicates "perfect weed death"). The results are shown in Table 1. [Table 1]

Test Examples 2: herbicidal effect on loose silkybent (pot test in greenhouse)

Plastic pots each having a size of 590 cm² x 8 cm were filled with steam sterilized soil. Seeds of loose silkybent were sown in the pots and covered with soil of 1 cm thickness. The plant was allowed to grow to the second- leaf stage.

A sulfosulfuron granular wettable agent (a granular wettable agent containing 80% of the compound 1; trade name: Monitor 80 granular wettable agent, manufactured by Monsanto) was diluted with water to prepare a dilution containing the compound 1. The compound 2 was dissolved in acetone containing 2% (W/V) of Tween 20 (surfactant), and then diluted with water so that the concentration of acetone in the resulting dilution is 10% to prepare a dilution containing the compound 2. In addition, a sulfosulfuron granular wettable agent (a granular wettable agent containing 80% of the compound 1; trade name: Monitor 80 granular wettable agent, manufactured by Monsanto) and a solution of the compound 2 in acetone containing 2% (W/V) of Tween 20 (surfactant) were mixed and diluted in a predetermined ratio to prepare a dilution containing the compound 1 and the compound 2. Each 500 L/ha of the dilutions thus obtained were sprayed over the loose silkybent in the second-leaf stage in the pots so that the drug amounts listed in Table 2 were applied.

Three weeks after the application, herbicidal effects of the dilutions on loose silkybent were evaluated

(herbicidal effect 0% indicates "no effect", and herbicidal effect 100% indicates "perfect weed death"). The results are shown in Table 2.

[Table 2]

Test Examples 3: phytotoxicity to wheat (pot test in greenhouse) Plastic pots each having a size of 590 cm² x 8 cm were filled with steam sterilized soil. Seeds of wheat were sown in the pots and covered with soil of 1 cm thickness. A sulfosulfuron granular wettable agent (a granular wettable agent containing 80% of the compound 1; trade name: Monitor 80 granular wettable agent, manufactured by Monsanto) and a solution of the compound 2 in acetone containing 2% (W/V) of Tween 20 (surfactant) were mixed and diluted in predetermined ratios to prepare dilutions containing the compound 1 and the compound 2. Each 500 L/ha of the dilutions thus obtained were sprayed onto the soil surface in the pots in which seeds of wheat were sown so that the drug amounts listed in Table 3 were applied.

Three weeks after the application, herbicidal effects of the dilutions on wheat were evaluated (phytotoxicity 0% indicates "no effect", and phytotoxicity 100% indicates "perfect wheat death"). The results are shown in Table 3. [Table 3]

As seen from Test Examples, the composition of the present invention had high herbicidal effect on weeds (e.g., wild mustard and loose silkybent) , while the composition of the present invention had no phytotoxicity to crops (e.g. wheat) .

Industrial Applicability According to the present invention, a wide variety of weeds in crop fields can be controlled by applying a small amount of a herbicidal composition.

Claims

1. A herbicidal composition which comprises: [a] 1- (4, β-dimethoxypyrimidin-2-yl) -3- (2- ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea, and [b] a compound represented by the formula (II):

as active ingredients.

2. A herbicidal composition for controlling weeds in crop fields which comprises [a] 1- (4, 6-dimethoxypyrimidin-2-yl) -

3- ( 2-ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea and [b] a compound represented by the formula (II) as active ingredients, wherein the weight ratio of [a] : [b] is from 1:0.1 to 1:10.

3. A method for controlling weeds in crop fields which comprises applying [a] 1- (4 , β-dimethoxypyrimidin-2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea and [b] a compound represented by the formula (II) in combination as a mixture or separate compositions, to weeds or to soil in a place where weeds grow or will grow.

4. A method for controlling weeds in crop fields which comprises applying [a] 1- (4, 6-dimethoxypyrimidin-2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea and [b] a compound represented by the formula (II) in combination as a mixture or separate compositions, wherein the weight ratio of [a] : [b] is from 1:0.1 to 1:10, to weeds or to soil in a place where the weeds grow or will grow.