WO2009064001A2

WO2009064001A2 - Herbicidal composition

Info

Publication number: WO2009064001A2
Application number: PCT/JP2008/070829
Authority: WO
Inventors: Hajime Ikeda; Satoru Kizawa
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2007-11-12
Filing date: 2008-11-10
Publication date: 2009-05-22
Anticipated expiration: 2010-05-12
Also published as: AR069179A1; JP2009137944A; WO2009064001A3; CL2008003343A1

Abstract

The present invention provides a novel herbicidal composition comprising 1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea and 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-ylsulfonyl)urea as active ingredients.

Description

DESCRIPTION HERBICIDAL COMPOSITION

Technical Field The present invention relates to a herbicidal composition.

Background Art

Nowadays, a number of herbicides are commercially available for practical use (see Crop Protection Handbook, vol.89 (2003), Meister Publishing Company, ISBN: 1-892829- 06-1) . However, existing herbicides do not always provide satisfactory effect because there are a wide variety of weeds to be controlled which emerge at different times of year. Thus there is still a need for development of novel herbicides .

Disclosure of the Invention

An object of the present invention is to provide a novel herbicidal composition.

Thus, the present invention provides: (1) A herbicidal composition comprising l-(2- chloroimidazo [1, 2-a] pyridin-3-ylsulfonyl) -3- (4 , 6- dimethoxypyrimidin-2-yl) urea and 1- (4 , 6-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3- ylsulfonyl) urea as active ingredients (hereinafter, referred to as "the composition of the present invention");

(2) A weed control method which comprises applying l-(2- chloroimidazo [1, 2-a] pyridin-3-ylsulfonyl) -3- (4 , 6- dimethoxypyrimidin-2-yl ) urea and 1- (4 , 6-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3- ylsulfonyl) urea to weeds or to the soil of a place where weeds grow or will grow;

(3) A weed control method in a wheat field, a lawn, a tree land or a non-crop land, which comprises applying 1- (2- chloroimidazo [1, 2-a] pyridin-3-ylsulfonyl) -3- (4 , 6- dimethoxypyrimidin-2-yl) urea and 1- (4 , β-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3- ylsulfonyl) urea to weeds or to the soil of a place where weeds grow or will grow (hereinafter, the above (2) and (3) may be collectively referred to as "the method of the present invention"); and

(4) Use of a combination of 1- (2-chloroimidazo [1, 2- a] pyridin-3-ylsulfonyl) -3- (4 , 6-dimethoxypyrimidin-2-yl) urea and 1- (4 , β-dimethoxypyrimidin-2-yl) -3- (2- ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea for controlling weeds in a wheat field, a lawn, a tree land or a non-crop land.

Best Mode for Carrying Out the Invention One active ingredient of the composition of the present invention, 1- (2-Chloroimidazo [1, 2-a] pyridin-3- ylsulfonyl) -3- (4 , 6-dimethoxypyrimidin-2-yl) urea (common name: imazosulfuron, hereinafter, referred to as "the compound 1") is a herbicidally active compound described in Crop Protection Handbook, vol.89 (2003), Meister Publishing Company, ISBN: 1-892829-06-1, pp.C440, and can be prepared by a known method.

The other active ingredient of the composition of the present invention, 1- ( 4 , 6-dimethoxypyrimidin-2-yl) -3- (2- ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea (common name: sulfosulfuron, hereinafter, referred to as "the compound 2") is a herbicidally active compound described in Crop Protection Handbook, Vol. 89 (2003), Meister Publishing Company, ISBN: 1-892829-06-1, pp.C434, and can be prepared by a known method.

Formulations containing the compound 1 and formulations containing the compound 2 are also commercially available. The composition of the present invention has herbicidal effect on a wide variety of weeds and can be used in various situations (e.g., a crop land and a non- crop land) . For example, the composition of the present invention can control a wide variety of weeds effectively in a wheat field where the wheat is cultivated with or without tillage, a lawn, a tree land or a non-crop land.

Examples of the lawn, as used herein, include a golf course, a baseball stadium, a soccer field, a playground, a racetrack, a park and a lawn field, on which Zoysia japonica (Japanese lawngrass), Zoysia matrella (Manila grass), Cynodon dactylon (Bermuda grass), Pennisetum clandestinum (Kikuyu grass), Paspalum notatum (Bahia grass), Paspalum vaginatum (Seashore paspalum) , Stenotaphrum secundatum (St. Augustine grass), Buchloe dactyloides (Buffalo grass), Eremochloa ophiuroides (Centiped grass), Andropogon (bluestems), Sorghastrum nutans (Indian grass), Eragrostis japonica (love grass), Bouteloua gracilis (blue grama), Panicum virgatum (switchgrass) , Agrostis stolonifera (creeping bent grass), Poa pratensis (Kentucky bluegrass), Lolium perenne (perennial ryegrass) or Festuca (fescue grass) is grown.

Examples of the tree land, as used herein, include an orchard, a tea field, a mulberry field, a coffee plantation, a banana plantation, a coconut plantation, a flowering tree plantation, a flowering tree field, a nursery garden, a tree nursery, forest land and garden. Examples of the orchard include pome fruits (apple, common pear, Japanese pear, Chinese quince, quince etc.), stone fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune etc.), citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruit etc.), tree nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut etc.), berry fruits (blueberry, cranberry, blackberry, raspberry etc.), grape, persimmon, olive, and loquat. Examples of the non-crop land, as used herein, include a playground, a vacant land, a railroad side, a park, a parking lot, a roadside, a dry riverbed, a lot under a power transmission line, a housing area and a plant site.

Examples of the weeds which can be controlled by the composition of the present invention include

Polygonaceae weeds: Polygonum lapathifolium, Polygonum longisetum and Rumex japonicus; Portulacaceae weeds: Portulaca oleracea;

Caryophyllaceae weeds: Stellaria media; Chenopodiaceae weeds: Chenopodium album;

Amaranthaceae weeds: Amaranthus retroflexus, Amaranthus viridis and Amaranthus lividus;

Cruciferae weeds: Raphanus raphanistrum, Sinapis arvensis and Capsella bursa-pastoris; Leguminosae weeds: Sesbania exaltata;

Malvaceae weeds: Abutilon theophrasti;

Violaceae weeds: Viola arvensis;

Rubiaceae weeds: Galium aparine;

Convolvulaceae weeds: Ipomoea hederacea, Ipomoea purpurea, Ipomoea hederacea var integriuscula, Ipomoea lacunosa;

Solanaceae weeds : Solanum nigrum; Scrophulariaceae weeds: Veronica hederaefolia; Lamiaceae weeds: Lamium amplexicaule; Asteraceae weeds: Xanthium pensylvanicum, Matricaria chamomilla, Artemisia princeps, Solidago altissima, Taraxacum officinale, Galinsoga ciliata;

Poaceae weeds: Echinochloa crus-galli, Setaria viridis, Setaria faberi, Digitaria sanguinalis, Sorghum halepense, Alopecurus myosuroides, Lolium multiflorum, Avefa fatua, Poa annua; and

Cyperaceae weeds: Cyperus rotundus, Cyperus esculentus, Kyllinga gracillima.

The ratio of the compound 1 to the compound 2 as active ingredients contained in the composition of the present invention is from about 1:0.01 to 1:100, preferably from about 1:0.02 to 1:20 by weight.

The composition of the present invention may be a mixture of the compound 1 and the compound 2 only. However, in addition to the compound 1 and the compound 2, the composition of the present invention usually contains a carrier such as a solid carrier or a liquid carrier and, if necessary, a surfactant and other auxiliary agents for formulation. The composition of the present invention may be prepared by mixing the compound 1 and the compound 2 together with a carrier, and then formulating the mixture into a suitable form, if necessary, after addition of a surfactant and other auxiliary agents for formulation to the mixture. Alternatively, the composition of the present invention may be prepared by formulating each of the compound 1 and the compound 2 into a suitable form together with a carrier and, if necessary, a surfactant and other auxiliary agents for formulation, and then mixing the formulations of the compound 1 and the compound 2.

In other words, the compound 1 and the compound 2 are used in combination in order to produce the composition of the present invention. The composition of the present invention can be produced by a method conventionally used for production of agricultural chemicals. When the composition of the present invention is in the form of an emulsifiable concentrate, a wettable powder, a water dispersible granule, a soluble concentrate, a water soluble powder, a suspension concentrate (also referred to as a flowable) or the like, the total amount of the compound 1 and the compound 2 contained in the composition of the present invention is usually from 1 to 90% by weight of the entire formulation. When the composition of the present invention is in the form of an oil solution, a dust, a DL- type dust or the like, the total amount of the compound 1 and the compound 2 contained in the composition of the present invention is usually from 0.01 to 10% by weight of the entire formulation. When the composition of the present invention is in the form of a micro granule, a micro granule F, a fine granule F, a granule or the like, the total amount of the compound 1 and the compound 2 contained in the composition of the present invention is from 0.05 to 10% by weight of the entire formulation. The above-described total amount of the compound 1 and the compound 2 contained in the composition of the present invention may be appropriately varied depending on the intended use.

Examples of the solid carrier include fine powder and granules of clays (e.g., kaolinite, diatomaceous earth, synthetic hydrous silicon oxide, agalmatolite clay, bentonite and acidic white clay) , talc, other inorganic minerals (e.g., sericite, quartz powder, sulfur powder, activated carbon and calcium carbonate) and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea) . Examples of the liquid carrier include water, alcohols (e.g., methanol and ethanol), ketones (e.g., acetone, methyl ethyl ketone and cyclohexanone) , aromatic hydrocarbons (toluene, xylene, ethylbenzene and methylnaphthalene) , non-aromatic hydrocarbons (e.g., hexane, cyclohexane and kerosene), esters (e.g., ethyl acetate and butyl acetate), nitriles (e.g., acetonitrile and isobutyronitrile) , ethers (e.g., dioxane and diisopropyl ether), acid amides (e.g., dimethylformamide and dimethylacetamide) and halogenated hydrocarbons (e.g., dichloroethane and trichloroethylene) .

Examples of the surfactant include alkyl sulfate esters, alkyl sulfonate salts, alkylaryl sulfonate salts, alkylaryl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol ethers, polyvalent alcohol esters and sugar alcohol derivatives.

Examples of the other auxiliary agents for formulation include sticking agents and dispersants such as casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives and alginic acid) , lignin derivatives, bentonite and synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid) ; and stabilizers such as PAP (acidic isopropyl phosphate), BHT (2 , 6-tert-butyl-4-methylphenol) , BHA (2-/3- tert-butyl-4-methoxyphenol) , vegetable oils, mineral oils, fatty acids and fatty acid esters.

According to the method of the present invention, the composition of the present invention as it is or a dilution of the composition of the present invention with water or the like may be applied to the plant bodies of targeted weeds or to the soil of a place where weeds grow or will grow. Specific examples of a method of applying the composition of the present invention to soil include spraying of the composition over the soil surface before the germination of useful plants to be protected and before the emergence of weeds; spraying of the composition from above over the soil surface after the germination of useful plants to be protected and before the emergence of weeds; spraying of the composition to the soil surface between furrows or between plants after the germination of useful plants to be protected and before the emergence of weeds; and spraying of the composition from above over the soil surface after the germination of useful plants to be protected and after the emergence of weeds. Specific examples of a method of applying the composition of the present invention to the plant bodies of targeted weeds include spraying of the composition from above to the foliage of the weeds before the germination of useful plants to be protected and after the emergence of the weeds; and spraying of the composition from above to the foliage of the weeds after the germination of useful plants to be protected and after the emergence of the weeds.

The composition of the present invention can be used in admixture with other herbicidally active compound. A mixture of the composition of the present invention and the other herbicidally active compound is expected to produce an enhanced herbicidal effect. The composition of the present invention can be also used in admixture with or in combination with an insecticide, a fungicide, a plant growth regulator, a fertilizer, a safener and/or a soil conditioner .

In the method of the present invention, the application rate of the composition of the present invention may be usually varied depending on a mixing ratio of the compound 1 and the compound 2 as active ingredients, a climate condition, the form of a formulation, an application time, an application method, a place to be applied, a targeted weed and a crop to be protected. In the case of soil application, the application rate of the composition of the present invention usually is from about 1 to about 1,500 g per hectare of the active ingredients in total. In the case of application to the plant body of a targeted weed, the application rate of the composition of the present invention usually is from about 1 to about 1,500 g per hectare of the active ingredients in total.

When the composition of the present invention in the form of an emulsifiable concentrate, a wettable powder or a suspension concentrate is applied to soil, the predetermined amount of the composition is diluted with about 100 to 2,000 liters per hectare of water and then sprayed. When the composition of the present invention in the form of an emulsifiable concentrate, a wettable powder or a suspension concentrate is applied to the plant body of a targeted weed, the predetermined amount of the composition is diluted with about 100 to 200 liters per hectare of water and then sprayed. When soil is treated with the composition of the present invention in the form of a granule, the granule is usually applied to the soil surface as it is. Further, in the case of application to the plant body of a targeted weed, an adjuvant may be added to the composition of the present invention or a dilution thereof. The addition of an adjuvant to the composition of the present invention or a dilution thereof is expected to result in an enhancement of the herbicidal effect.

Examples of the useful plant that can be grown or cultivated in a crop land where the active ingredients (i.e., the compound 1 and the compound 2) are applied for weed control include plants having resistance to herbicides including HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors, glutamine synthetase inhibitors, auxin-type herbicides such as 2,4-D and dicamba, and bromoxynil, which resistance is conferred by classic breeding technique, a genetic engineering technique or the like .

Examples of the useful plant to which herbicidal resistance is conferred by a classic breeding technique include crop plants having resistance to imidazolinone herbicides such as imazethapyr, and STS soybean which is resistant to sulfonylurea ALS inhibitor herbicides such as thifensulfuron-methyl .

Examples of the useful plant to which herbicidal resistance is conferred by a genetic engineering technique include plants having resistance to glyphosate and/or glufosinate .

The above useful plant also include crop plants having an ability to produce insecticidal toxins known as selective toxins produced from Bacillus bacteria, which ability is conferred by a genetic engineering technique.

Examples of the insecticidal toxin expressed in such a genetically engineered plant include insecticidal proteins produced from Bacillus cereus or Bacillus popilliae; δ- endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl and Cry9C produced from Bacillus thuringiensis; insecticidal proteins such as VIPl, VIP2, VIP3 and VIP3A; insecticidal proteins produced from nematode; toxins produced by animals such as a scorpion toxin, a spider toxin, a bee toxin and an insect specific nervous system toxin; filamentous fungus toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin and papain inhibitors; ribosome inactivation proteins (RIP) such as ricins, corn-RIP, abrins, luffin, saporins, and bryodin; steroid metabolism enzymes such as 3- hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; Juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl synthase; chitinase; and glucanases.

Further examples of the insecticidal toxin include hybrid toxins of the above-described insecticidal toxin (e.g., δ-endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl and Cry9C and insecticidal proteins such as VIPl, VIP2, VIP3 and VIP3A) ; and insecticidal proteins in which a part of amino acids constituting the above-described insecticidal proteins is deleted or modified. The hybrid toxins are created by combining different domains of the above-described insecticidal proteins by a genetic engineering technique. An example of the toxin in which a part of amino acids constituting the insecticidal protein is deleted includes CrylAb in which a part of amino acids is deleted. An example of the toxin in which a part of amino acids constituting the insecticidal protein is modified is made by substitution of one or more amino acids of a natural toxin.

The insecticidal toxins and genetically engineered crop plants which have the ability to produce the insecticidal toxins are described, for example, in EP-A- 0374753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A- 451878 and WO 03/052073.

The useful plants which are given the ability to produce the insecticidal toxins by a genetic engineering technique have resistance to attack by Coleopteran pests, Dipteran pests and/or Lepidopteran pests.

Genetically engineered plants having one or more pest- resistant genes and expressing one or more insecticidal toxins are already known, and some of them are commercially available.

The useful plants also include plants having an ability to produce selective anti-pathogen substances, which ability is conferred by a genetic engineering technique. As an example of the anti-pathogen substances, PR proteins (PRPs, described in EP-A-0392225) is known. Such anti-pathogen substances and genetically engineered plants capable of producing them are described, for example, in EP-A-0392225, WO 95/33818 and EP-A-0353191. Examples of the anti-pathogen substances expressed in the genetically engineered plants include ion channel inhibitors such as sodium channel inhibitors, and calcium channel inhibitors (e.g., KPl, KP4 and KP6 toxins produced by virus are known) ; stilbene synthase; bibenzyl synthase; chitinase; glucanase; microorganism-producing substances such as peptide antibiotics, antibiotics having a heterocycle, and protein factors relating to plant disease resistance (referred to as plant disease-resistant genes and described in WO 03/000906) .

Examples

The present invention will be further specifically illustrated by the following Formulation Examples and Test Examples which the present invention is not limited to.

Formulation Examples are shown below. In the following Examples, the term "part(s)" means part(s) by weight .

Formulation Example 1

Twenty parts of the compound 1, 5 parts of the compound 2, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 70 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 Ten parts of the compound 1, 10 parts of the compound 2, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 75 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 3

Five parts of the compound 1, 20 parts of the compound 2, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 70 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 4 Ten parts of the compound 1, 10 parts of the compound 2, 3 parts of polyoxyethylene sorbitan monoolate, 3 parts of CMC (carboxymethyl cellulose) and 74 parts of water are mixed and then wet-ground until the grain size become 5 micron or less to obtain a suspension concentrate.

Formulation Example 5

Twenty parts of the compound 1, 5 parts of the compound 2, 3 parts of polyoxyethylene sorbitan monoolate, 3 parts of CMC (carboxymethyl cellulose) and 69 parts of water are mixed and then wet-ground until the grain size become 5 micron or less to obtain a suspension concentrate.

Formulation Example 6

Fifty five parts of the compound 1, 20 parts of the compound 2, 3 parts of polyoxyethylene sorbitan monoolate, 3 parts of CMC (carboxymethyl cellulose) and 69 parts of water are mixed and then wet-ground until the grain size become 5 micron or less to obtain a suspension concentrate.

Formulation Example 7

In a small-sized kneader, 1 part of the compound 1, 1 part of the compound 2, 0.5 part of Neocol YSK (a dialkylsulfosuccinate surfactant; Daiichi Kogyo Seiyaku Co., Ltd.), 2 parts of Toxanon GR31A (a polycarboxylic acid anionic surfactant; Sanyo chemical industries, Ltd.), 30 parts of Kunigel Vl (a bentonite; Kunimine Industries Co., Ltd.) and 65.5 parts of calcium carbonate are placed, mixed, kneaded, granulated with an extrusion granulator, dried in a fluidized bed drier, and then sieved at 16 to 48 mesh to obtain a granule.

Test Examples will be described below. [Evaluation Criteria]

A herbicidal effect is rated on a scale of 0 to 10, and is shown as a score of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The score'O" indicates that the germination or growth state of a tested weed is little different from that of an untreated weed. The score "10" indicates that a tested weed is killed completely or the germination or growth of a tested weed is completely suppressed.

Evaluation of crop injury is shown as "non-injury" indicating that little injury is observed, "mild" indicating that mild crop injury is observed, "moderate" indicating that moderate crop injury is observed or "severe" indicating that severe crop injury is observed.

Test Example 1

A plastic pot with a width of 32 cm, a depth of 22 cm and a height of 8 cm was filled with field soil, and seeds of Lolium multiflorum were sown thereon.

On the day of sowing, each of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.), a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto), and a mixture of the imazosulfuron suspension concentrate and the sulfosulfuron water dispersible granule was diluted with water and then sprayed over the soil surface uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 1 could be attained.

The plants were grown in a greenhouse. A herbicidal effect was determined 28 days after the chemical treatment Results are shown in Table 1. [Table 1]

(In the table, Lm denotes Lolium multiflorum. )

As shown in Table 1, by the treatment with the composition of the present invention, an excellent herbicidal effect was synergistically provided, as compared with that by the treatment with the compound 1 alone or compound 2 alone.

Test Example 2 A plastic pot with a width of 32 cm, a depth of 22 cm and a height of 8 cm was filled with field soil, and seeds of wheat, Alopecurus myosuroides, Sinapis arvensis, Stellaria media and Chenopodium album were sown thereon. On the day of sowing, a mixture of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.) and a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto) was diluted with water and then sprayed over the soil surface uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 2 could be attained.

The plants were grown in a greenhouse. A herbicidal effect and crop injury were determined 28 days after the chemical treatment. Results are shown in Table 2. [Table 2]

(In Table 2, Am denotes Alopecurus myosuroides, Sa denotes Sinapis arvensis, Sm denotes Stellaria media and Ca denotes Chenopodium album. )

As shown in Table 2, by the treatment with the composition of the present invention, an excellent herbicidal effect was provided. On the other hand, injury to wheat was determined to be "non-injury". Test Example 3

A plastic pot with a width of 32 cm, a depth of 22 cm and a height of 8 cm was filled with field soil, and seeds of wheat, Avefa fatua, Alopecurus myosuroides, Sinapis arvensis and Stellaria media were sown thereon.

Fourteen days after sowing, a mixture of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.) and a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto) was diluted with water and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 3 could be attained.

The plants were grown in a greenhouse. A herbicidal effect and crop injury were determined 28 days after the chemical treatment. Results are shown in Table 3.

[ Table 3 ]

(In Table 3, Af denotes Avefa fatua, Am denotes Alopecurus myosuroides, Sa denotes Sinapis arvensis, and Sm denotes Stellaria media.)

As shown in Table 3, by the treatment with the composition of the present invention, an excellent herbicidal effect was provided. On the other hand, injury to wheat was determined to be "non-injury".

Test Example 4

A plastic pot with a diameter of 240 cm and a height of 21 cm was filled with field soil, and seeds of Ipomoea hederacea and Abutilon theophrasti were sown thereon. Fourteen days after sowing, a tomato seedling at the 2 leaf stage (variety: Patio) was transplanted in the pot.

Five days after the transplantion, a mixture of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.) and a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto) was diluted with water and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 4 could be attained.

The plants were grown in a greenhouse. A herbicidal effect and crop injury were determined 33 days after the chemical treatment. Results are shown in Table 4. [Table 4]

(In Table 4, Ih denotes Ipomoea hederacea and At denotes Abutilon theophrasti . )

As shown in Table 4, by the treatment with the composition of the present invention, an excellent herbicidal effect was provided. On the other hand, injury to the transplanted tomato was determined to be "non- injury" .

Test Example 5 A plastic pot with a diameter of 160 cm and a height of 136 cm was filled with field soil. Subterranean stems of Equisetum arvense were transplanted in the pot and then grown. Sixty-nine days after the transplantation, shoots were cut at 3 cm above the ground level. Seventy-six days after the transplantation of

Equisetum arvense, a mixture of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.) and a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto) was diluted with water and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 5 could be attained. As a comparative example, the imazosulfuron suspension concentrate and a wettable powder of 3-chloro-5- (4, 6-dimethoxypyrimidin-2-ylsulfamoyl) -l-methylpyrazole-4- carboxylic acid methyl ester (common name: halosulfuron methyl; hereinafter, referred to as "the compound 3") (a wettable powder containing 10% of the compound 3; trade name: Inpool wettable powder manufactured by Nissan Chemical Industries Ltd.) were mixed and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 5 could be attained.

The plants were grown in a greenhouse. Twenty-nine days after the chemical treatment, shoots were cut at 5 mm above the ground level. Twenty-eight days after the cut, it was determined whether the shoot regeneration occurred or not, and the plant height of the largest individual was measured. Results are shown in Table 5. [Table 5]

As shown in Table 5, by the treatment with the composition of the present invention in combination with cutting of shoots (simulation of mowing) after the chemical treatment, a high herbicidal effect on Equisetum arvens, which is a troublesome weed in non-crop land, was provided.

Test Example 6

A plastic pot with a diameter of 160 cm and a height of 80 cm was filled with field soil. Seeds of Bermudagrass (variety: Savanna) were sown in the pot and then grown. Ninety-two days after sowing, shoots were cut at 3 cm above the ground level. Then, seeds of Sorghum halepense were sown in the pot. On the next day of sowing Sorghum halepense, each of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.), a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto), and a mixture of the imazosulfuron suspension concentrate and the sulfosulfuron water dispersible granulewas diluted with water and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 6 could be attained. As a comparative example, the imazosulfuron suspension concentrate and a halosulfuron methyl wettable powder (a wettable powder containing 10% of the compound 3; trade name: Inpool wettable powder manufactured by Nissan

Chemical Industries Ltd.) were mixed and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 6 could be attained. The plants were grown in a greenhouse. Thirty-seven days after the chemical treatment, shoots were cut at 3 cm above the ground level. Fourteen days after cutting, a herbicidal effect and crop injury were determined. Results are shown in Table 6. [Table 6]

As shown in Table 6, by the treatment with the composition of the present invention in combination with cutting of shoots (simulation of lawn mowing) after the chemical treatment, a high herbicidal effect on Sorghum halepense was provided. The herbicidal effect was synergistically high as compared with the treatment with the compound 1 or compound 2 alone. On the other hand, injury to the lawn of Bermudagrass was determined to be "non-injury" .

Test Example 7

A plastic pot with a diameter of 120 cm and a height of 80 cm was filled with field soil. Seeds of Kentucky bluegrass (variety: Blue velvet) were sown in the pot and then grown. Ninety-two days after sowing, shoots were cut at 3 cm above the ground level. Then, seeds of Sorghum halepense were sown in the pot.

On the next day of sowing Sorghum halepense, a mixture of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.) and a sulfosulfuron water dispersible granule (a ■water dispersible granulecontaining 80% of the compound 2 ; trade name: Monitor 80 WDG manufactured by Monsanto) was diluted with water and then sprayed from above to the plants uniformly using a small-sized spray pump so that an application amount of the active ingredients shown in Table 7 could be attained. As a comparative example, the imazosulfuron suspension concentrate and a halosulfuron methyl wettable powder (a wettable powder containing 10% of the compound 3; trade name: Inpool wettable powder manufactured by Nissan Chemical Industries Ltd.) were mixed and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 7 could be attained.

The plants were grown in a greenhouse. Thirty-seven days after the chemical treatment, shoots were cut at 3 cm above the ground level. Fourteen days after cutting, a herbicidal effect and crop injury were determined. Results are shown in Table 7.

As shown in Table 7, by the treatment with the composition of the present invention in combination with cutting of shoots (simulation of lawn mowing) after the chemical treatment, a high herbicidal effect on Sorghum halepense was provided. On the other hand, injury to the lawn of Kentucky bluegrass was determined to be "non- injury" .

Test Example 8

A plastic pot with a diameter of 120 cm and a height of 80 cm was filled with field soil. Seeds of perennial ryegrass (variety: Citation IV) were sown in the pot and then grown. Ninety-two days after sowing, shoots were cut at 3 cm above the ground level. Then, seeds of Sorghum halepense were sown in the pot. On the next day of sowing Sorghum halepense, a mixture of an imazosulfuron suspension concentrate (a suspension concentrate containing 40% of the compound 1; trade name: Sibatite 40 manufactured by Sumitomo Chemical Takeda Agro Co., Ltd.) and a sulfosulfuron water dispersible granule (a water dispersible granulecontaining 80% of the compound 2; trade name: Monitor 80 WDG manufactured by Monsanto) was diluted with water and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 8 could be attained. As a comparative example, the imazosulfuron suspension concentrate and a halosulfuron methyl wettable powder (a wettable powder containing 10% of the compound 3; trade name: Inpool wettable powder manufactured by Nissan Chemical Industries Ltd.) were mixed and then sprayed from above to the plants uniformly using a small sprayer so that an application rate of the active ingredients shown in Table 8 could be attained.

The plants were grown in a greenhouse. Thirty-seven days after the chemical treatment, shoots were cut at 3 cm above the ground level. Fourteen days after cutting, a herbicidal effect and crop injury were determined. Results are shown in Table 8. [ Table 8 ]

As shown in Table 8, by the treatment with the composition of the present invention in combination with cutting of shoots (simulation of lawn mowing) after the chemical treatment, a high herbicidal effect on Sorghum halepense was provided. On the other hand, injury to the lawn of perennial ryegrass was determined to be "non- injury" .

Industrial Applicability- According to the present invention, it is possible to provide a novel herbicidal composition.

Claims

1. A herbicidal composition comprising 1- (2- chloroimidazo [1, 2-a] pyridin-3-ylsulfonyl) -3- (4 , 6- dimethoxypyrimidin-2-yl) urea and 1- (4 , 6-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3- ylsulfonyl) urea as active ingredients.

2. A weed control method which comprises applying 1- (2- chloroimidazo [1, 2-a] pyridin-3-ylsulfonyl) -3- (4 , 6- dimethoxypyrimidin-2-yl ) urea and 1- (4 , 6-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3- ylsulfonyl ) urea to weeds or to the soil of a place where weeds grow or will grow.

3. A weed control method in a wheat field, a lawn, a tree land or a non-crop land, which comprises applying l-(2- chloroimidazo [1, 2-a] pyridin-3-ylsulfonyl) -3- (4 , 6- dimethoxypyrimidin-2-yl) urea and 1- (4 , β-dimethoxypyrimidin- 2-yl) -3- (2-ethylsulfonylimidazo[l,2-a]pyridin-3- ylsulfonyl) urea to weeds or to the soil of a place where weeds grow or will grow.

4. Use of a combination of 1- (2-chloroimidazo [1, 2- a] pyridin-3-ylsulfonyl) -3- (4 , 6-dimethoxypyrimidin-2-yl) urea and 1- (4, β-dimethoxypyrimidin-2-yl) -3- (2- ethylsulfonylimidazo [1, 2-a] pyridin-3-ylsulfonyl) urea for controlling weeds in a wheat field, a lawn, a tree land or a non-crop land.