WO2013180309A1 - Herbicidal composition comprising nicosulfuron and bicyclopyrone - Google Patents

Herbicidal composition comprising nicosulfuron and bicyclopyrone Download PDF

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Publication number
WO2013180309A1
WO2013180309A1 PCT/JP2013/065635 JP2013065635W WO2013180309A1 WO 2013180309 A1 WO2013180309 A1 WO 2013180309A1 JP 2013065635 W JP2013065635 W JP 2013065635W WO 2013180309 A1 WO2013180309 A1 WO 2013180309A1
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Prior art keywords
herbicidal composition
herbicidal
spp
salt
compound
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PCT/JP2013/065635
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French (fr)
Inventor
Ryu Yamada
Hiroyuki Okamoto
Takashi Terada
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Ishihara Sangyo Kaisha, Ltd.
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Publication of WO2013180309A1 publication Critical patent/WO2013180309A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to a herbicidal composition
  • a herbicidal composition comprising (a) nicosulfuron or its salt (hereinafter referred to as compound A) and (b) bicyclopyrone or its salt (hereinafter referred to as compound B).
  • Patent Document 1 discloses a selective herbicidal composition comprising a herbicidally effective amount of a compound having a specific chemical structure and a synergistically effective amount of at least one compound selected from specific herbicides.
  • Patent Document 1 failed to specifically disclose remarkable
  • Patent Document 1 European Patent Application No. 1842426
  • herbicidal compositions have been developed and used, but there are a variety of types of undesired plants represented by weeds to be controlled. Further, undesired plants having lowered sensitivity to herbicides (herbicide-resistant weeds) emerged, and in some applications, practically, herbicides have only
  • the object of the present invention is to provide a high active herbicidal composition having a broader herbicidal spectrum, and a method for controlling undesired plants or inhibiting their growth using it. SOLUTION TO PROBLEM
  • herbicidally active ingredients in the present invention as compared with a case where the respective compounds are applied individually.
  • the present invention relates to a herbicidal composition comprising compound A and compound B as herbicidally active ingredients.
  • the present invention further relates to a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the herbicidal composition to the undesired plants or to a place where they grow.
  • the present invention further relates to a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of compound A and a herbicidally effective amount of compound B, to the undesired plants or to a place where they grow.
  • the herbicidal composition of the present invention is capable of controlling a wide range of undesired plants emerging in agricultural fields or non-agricultural fields. It surprisingly represents a synergistic effect i.e. a herbicidal effect higher than the mere addition of the respective herbicidal effects of the active ingredients.
  • a herbicidal composition of the present invention can be applied at a low dose as compared with a case where the respective active ingredients are applied individually. Thus, it is effective to reduce the environmental load on an area where the composition is applied or a surrounding area thereof.
  • the herbicidal activity in a case where two active ingredients are combined is larger than the simple sum of the respective herbicidal activities of the two active ingredients (the expected activity), it is called a synergistic effect.
  • the activity expected by the combination of two active ingredients can be calculated as follows (Colby S.R., "Weed", vol. 15, p. 20-22, 1967).
  • the activity by the combination can be regarded as showing a synergistic effect.
  • the herbicidal composition of the present invention shows a synergistic effect when calculated by the above formula.
  • nicosulfuron (common name) is 2-(4,6-dimethoxypyrimidin-2- ylcarbamoylsulfamoyl)-N,N-dimethylnicotinamide.
  • bicyclopyrone (common name) is 4-hydroxy-3- ⁇ 2-[(2- methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridylcarbonyl ⁇ bicyclo[3.2.1]oct-3-en-2- one.
  • the salt included in compound A and compound B may be any salt so long as it is agriculturally acceptable.
  • alkali metal salts such as a sodium salt and a potassium salt
  • alkaline earth metal salts such as a magnesium salt and a calcium salt
  • ammonium salts such as a monomethylammonium salt, a dimethylammonium salt and a triethylammonium salt
  • inorganic acid salts such as a hydrochloride, a perchlorate, a sulfate and a nitrate, and organic acid salts such as an acetate and a methanesulfonate.
  • the mixing ratio of compound A to compound B cannot generally be defined, as it varies depending upon various conditions such as the type of the formulation, the weather conditions, and the type and the growth stage of the undesired plants, and is, for example, from 7.5:1 to 1 :100, preferably from 4:1 to 1 :30 by the weight ratio.
  • herbicidally effective amounts of compounds A and B cannot generally be defined, as they vary depending upon various conditions such as the mixing ratio of the respective compounds, the type of the formulation, the weather conditions, and the type and the growth stage of the undesired plants.
  • compound A is applied in an amount of from 5 to 150 g/ha, preferably from 10 to 100 g/ha
  • compound B is applied in an amount of from 20 to 500 g/ha, preferably from 25 to 300 g/ha.
  • the herbicidal composition of the present invention may be applied to undesired plants or may be applied to a place where they grow. Further, it may be applied at any time either before or after the emergence of the undesired plants. Further, the herbicidal composition of the present invention may take various application forms such as soil application, foliar application, irrigation application, and submerged application, and it can be applied to agricultural fields such as upland fields, orchards and paddy fields, and non-cropland such as ridges of fields, fallow fields, play grounds, golf courses, vacant lands, forests, factory sites, railway sides and roadsides.
  • the herbicidal composition of the present invention can control a wide range of undesired plants such as annual weeds and perennial weeds.
  • the undesired plants to be controlled by the herbicidal composition of the present invention may, for example, be specifically cvperaceae such as sedge (Cyperus spp.) (such as purple nutsedge (Cyperus rotundus L), smallflower umbrella sedge (Cyperus difformis L), yellow nutsedge (Cyperus esculentus L.) or amur cyperus (Cyperus microiria Steud.)) or spikesedge (Kyllinga spp.) (such as green kyllinga (Kyllinqa brevifolia Rottb. var. leiolepis)); gramineae such as barnyard grass (Echinochloa spp.) (such as
  • barnyardgrass Echinochloa crus-galli L
  • early watergrass Echinochloa oryzicola vasing.
  • Japanese millet Echinochloa utilis Ohwi et Yabuno
  • crabgrass Digitaria spp.
  • summergrass Digitaria ciliaris (Retz.) Koel
  • large crabgrass Digitaria sanguinalis L
  • violet crabgrass Digitaria violascens Link
  • Jamaican crabgrass Digitaria horizontalis Willd.
  • goosegrass Eleusine spp.
  • foxtail (Setaria spp.) (such as green foxtail (Setaria viridis (L.))
  • sorghum (Sorghum spp.) (such as johnsongrass (Sorghum halepense (L.) Pers.) or shattercane (Sorghum bicolor (L.) Moench.)
  • oat (Avena spp.) (such as wild oat
  • brome Bromus spp.
  • meadowgrass (such as annual bluegrass (Poa annua L.)
  • foxtail grass (Alopecurus spp.) (such as blackgrass (Alopecurus myosuroides Huds.), shortawn foxtail (Alopecurus aegualis Sobol. var.
  • et Sherff beggarticks (Bidens subalternans DC.)), hairy fleabane (Convza bonariensis (L.) Cronq.), dandelion (Taraxacum officinale Weber), horseweed (Convza spp.) (such as Canadian horseweed (Convza canadensis (L.) Cronquist)), cocklebur (Xanthium spp.) (such as common cocklebur (Xanthium strumarium L.)), ragweed (Ambrosia spp.) (such as annual ragweed (Ambrosia artemisiifolia L.)), ragwort (Senecio spp.) (such as old-man-in-the-spring (Senecio vulgaris L.)); lequminosae such as rattlepod or rattlebox (Crotalaria spp.) (such as sunn-hemp (Crotalaria
  • sesbania pea or sesbania pea (Sesbania cannabina (Retz.) Pers. )), korean lespedeza (Kummerowia stipulacea (Maxim.) Makino) or white clover (Trifolium repens L.)); carvophvllaceae such as sticky chickweed (Cerastium glomeratum Thuill.) or starwort (Stellaria spp.) (such as common chickweed (Stellaria media L.)); euphorbiaceae such as garden spurge (Euphorbja hirta Lj, thj js ⁇ eeded copperleaf (Acalypha australis L.LorJireplant
  • Plantaqinaceae such as asiatic plantain (Plantaqo asiatica L.); oxalidaceae such as creeping woodsorrel (Oxalis corniculata L.); apiaceae such as lawn pennywort (Hvdrocotyle sibthorpioides Lam.); violaceae such as violet (Viola mandshurica W.
  • iridaceae such as blue-eyedgrass (Sisyrinchium rosulatum Bicknell); qeraniaceae such as Carolina geranium (Geranium carolinianum L.); labiatae such as purple deadnettle (Lamium purpureum L.) or henbit (Lamium amplexicaule L.); malvaceae such as velvetleaf (Abutilon theophrasti MEDIC.) or prickly sida (Sida spinosa L.); convolvulaceae such as ivy-leaved morningglory (Ipomoea hederacea (L.) Jacq.), common morningglory (Ipomoea purpurea ROTH), cypressvine morningglory (Ipomoea quamoclit L), Ipomoea qrandifolia (DAMMERMANN) O'DONNELL.
  • ivy-leaved morningglory Ipomoe
  • hairy merremia (Merremia aeqyptia (L.) URBAN) or field bindweed (Convolvulus arvensis L); chenopodiaceae such as goosefoot (Chenopodium spp.) (such as common lambsquarters (Chenopodium album L.)); portulacaceae such as common purslane (Portulaca oleracea L); amaranthaceae such as pigweed (Amaranthus spp.) (such as prostrate pigweed (Amaranthus blitoides S.
  • chenopodiaceae such as goosefoot (Chenopodium spp.) (such as common lambsquarters (Chenopodium album L.)
  • portulacaceae such as common purslane (Portulaca oleracea L)
  • amaranthaceae such as pigweed (Amaranthus spp.) (such as prostrate pigweed (Amaranthus
  • amaranth (Amaranthus rudis Sauer.)); solanaceae such as nightshade (Solanum spp.) (such as black nightshade (Solanum nigrum L.)); polvqonaceae such as knotweed
  • Polygonum spp. such as spotted knotweed (Polygonum lapathifolium L.) or green smartweed (Polygonum scabrum MOENCH)
  • cruciferae such as flexuous bittercress (Cardamine flexuosa WITH.), or mustard (Sinapis spp.) (such as Charlock (Sinapis arvensis L.)); cucurbitaceae such as burcucumber (Sicyos angulatus L);
  • commelinaceae such as common dayflower (Commelina communis L); rosaceae such as mock strawberry (Duchesnea chrysantha (Zoll. et Mor. ) Miq.); molluqinacea such as carpetweed (Mollugo verticillata L); or rubiaceae such as false cleavers (Galium spurium var. echinospermon (Wallr.) Hayek) or stickywilly (Galium aparine L).
  • rosaceae such as mock strawberry (Duchesnea chrysantha (Zoll. et Mor. ) Miq.); molluqinacea such as carpetweed (Mollugo verticillata L); or rubiaceae such as false cleavers (Galium spurium var. echinospermon (Wallr.) Hayek) or stickywilly (Galium aparine L).
  • the herbicidal composition of the present invention is very useful in practical application. For example, the following cases may be mentioned.
  • a herbicidal composition having a long lasting herbicidal effect i.e. a long lasting residual activity, as compared with a case where compound A and compound B are applied individually, may be provided in some cases.
  • a herbicidal composition having a broad spectrum having high effects against both gramineae and broad leaf weeds, as compared with a case where compound A and compound B are applied individually, may be provided in some cases.
  • Emergence of herbicide-resistant weeds and weeds having lowered sensitivity to herbicides may be suppressed in some cases as compared with a case where compound A and compound B are applied individually.
  • Safety for useful crop plants may be improved in some cases as compared with a case where compound A and compound B are applied individually.
  • the herbicidal composition of the present invention may be mixed with or may be used in combination with other herbicides, fungicides, antibiotics, plant hormones, insecticides, fertilizers, phytotoxicity-reducing agents, etc., in addition to the above active ingredients, without departing from the intention and the scope of the present invention, whereby more excellent effects and activities may sometimes be obtained.
  • Such other herbicides may, for example, be (1) those which are believed to exhibit herbicidal effects by disturbing hormone activities of plants, (2) those which are believed to exhibit herbicidal effects by inhibiting photosynthesis of plants, (3) those which are believed to be converted to free radicals by themselves to form active oxygen in the plant body and show rapid herbicidal efficacy, (4) those which are believed to exhibit herbicidal effects by inhibiting chlorophyll biosynthesis of plants and abnormally accumulating a photosensitizing peroxide substance in the plant body, (5) those which are believed to exhibit herbicidal effects characterized by bleaching activities by inhibiting chromogenesis of plants such as carotenoids, (6) those which exhibit strong herbicidal effects specifically to gramineous plants, (7) those which are believed to exhibit herbicidal effects by inhibiting an amino acid biosynthesis of plants, (8) those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants, (9) those which are believed to exhibit herbicidal effects by inhibiting protein biosynthesis or lipid bio
  • the herbicidal composition of the present invention may be prepared by mixing compound A and compound B, as active ingredients, with various agricultural additives in accordance with conventional formulation methods for agricultural chemicals, and applied in various formulations such as dusts, granules, water dispersible granules, wettable powders, tablets, pills, capsules (including a formulation packaged by a water soluble film), water-based suspensions, oil-based suspensions, microemulsions, suspoemulsions, water soluble powders, emulsifiable concentrates, soluble
  • compound A and compound B may be mixed together for the formulation, or they may be separately formulated.
  • the additives to be used for the formulation include, for example, a solid carrier such as kaolinite, sericite, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite or starch; a solvent such as water, toluene, xylene, solvent naphtha, dioxane, dimethylsulfoxide, ⁇ , ⁇ -dimethylformamide, dimethylacetamide, N-methyl-2- pyrrolidone or an alcohol; an anionic surfactant such as a salt of fatty acid, a benzoate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyi sulfate, an alkylaryl sulfate, an alkyi diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyi sul
  • alkylnaphthalene sulfonic acid condensed with formaldehyde a nonionic surfactant such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an
  • oxyalkylene block polymer a polyoxyethylene alkyi ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, polyethylene glycol, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil or a polyoxypropylene fatty acid ester; a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil or liquid paraffins; and a transesterified vegetable oil such as methylated rapeseed oil or ethylated rapeseed oil.
  • a vegetable oil or mineral oil such as
  • additives may suitably be selected for use alone or in combination as a mixture of two or more of them, so long as the object of the present invention is met. Further, additives other than the above-mentioned may be suitably selected for use among those known in this field. For example, various additives commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, an anti-mold agent, a bubble agent, a disintegrator and a binder, may be used.
  • the mix ratio by weight of the active ingredients to such various additives in the herbicidal composition of the present invention may be from 0.001 :99.999 to 95:5, preferably from about 0.005:99.995 to about 90:10.
  • a proper method can be employed among various methods depending upon various conditions such as the application site, the type of the formulation, and the type and the growth stage of the undesired plants to be controlled, and for example, the following methods may be mentioned.
  • Compound A and Compound B are mixed and formulated together, and the formulation is applied as it is.
  • Compound A and Compound B are mixed and formulated together, and the formulation is diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
  • a spreader such as a surfactant, a vegetable oil or a mineral oil
  • Compound A and compound B are separately formulated, and as the case requires, the formulations are diluted to predetermined concentrations with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added, and the formulations are applied.
  • a spreader such as a surfactant, a vegetable oil or a mineral oil
  • Compound A and compound B are separately formulated, and the formulations are mixed when diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
  • a spreader such as a surfactant, a vegetable oil or a mineral oil
  • a herbicidal composition comprising (a) nicosulfuron or its salt and (b) bicyclopyrone or its salt.
  • the herbicidal composition according to (1) which comprises (a) and (b) in amounts to show a herbicidally synergistic effect (synergistic herbicidally effective amounts).
  • a method for controlling undesired plants or inhibiting their growth which comprises applying a herbicidally effective amount of a herbicidal composition comprising (a) and (b), to the undesired plants or to a place where they grow.
  • a method for controlling undesired plants or inhibiting their growth which comprises applying a herbicidally effective amount of (a) and a herbicidally effective amount of (b), to the undesired plants or to a place where they grow.
  • the growth inhibition rate (%) (measured value) and the growth inhibition rate (%) (calculated value) calculated by the Colby's formula are shown in Table 1.
  • ONEHOPE NYUZAI tradename
  • a wettable powder containing bicyclopyrone prepared by a conventional method
  • Upland field soil was put into a 1/1 ,000,000 ha pot, and seeds of annual ragweed (Ambrosia artemisiifolia L.) were sown.
  • annual ragweed Ambrosia artemisiifolia L.
  • predetermined amounts of ONEHOPE NYUZAI (tradename) and a wettable powder containing bicyclopyrone prepared by a conventional method were diluted with water in an amount corresponding to 300 LJha, and applied for foliar treatment by a small sprayer.
  • a herbicidal composition having a broad herbicidal spectrum, having high activity and having a long lasting effect can be provided. Further, according to the present invention, broadening of the herbicidal spectrum particularly against gramineae and application to genetically-modified crops resistant to ALS inhibitors are possible, and an increase in the application site can be expected ⁇

Abstract

At present, many herbicidal compositions have been developed and used, but there are a variety of types of undesired plants represented by weeds to be controlled. Thus, a high active herbicidal composition having a broader herbicidal spectrum has been desired. The present invention provides a herbicidal composition comprising (a) nicosulfuron or its salt and (b) bicyclopyrone its salt. According to the herbicidal composition of the present invention, a herbicidal composition having a broad herbicidal spectrum, having high activity and having a long-lasting effect can be provided.

Description

DESCRIPTION
TITLE OF INVENTION:
HERBICIDAL COMPOSITION COMPRISING NICOSULFURON AND BICYCLOPYRONE TECHNICAL FIELD
The present invention relates to a herbicidal composition comprising (a) nicosulfuron or its salt (hereinafter referred to as compound A) and (b) bicyclopyrone or its salt (hereinafter referred to as compound B).
BACKGROUND ART
Patent Document 1 discloses a selective herbicidal composition comprising a herbicidally effective amount of a compound having a specific chemical structure and a synergistically effective amount of at least one compound selected from specific herbicides.
However, Patent Document 1 failed to specifically disclose remarkable
synergistic effects obtainable by combination of compound A and compound B which are herbicidally active ingredients in the present invention.
PRIOR ART DOCUMENTS PATENT DOCUMENT
Patent Document 1 : European Patent Application No. 1842426
DISCLOSURE OF INVENTION TECHNICAL PROBLEM
At present, many herbicidal compositions have been developed and used, but there are a variety of types of undesired plants represented by weeds to be controlled. Further, undesired plants having lowered sensitivity to herbicides (herbicide-resistant weeds) emerged, and in some applications, practically, herbicides have only
insufficient effects. The object of the present invention is to provide a high active herbicidal composition having a broader herbicidal spectrum, and a method for controlling undesired plants or inhibiting their growth using it. SOLUTION TO PROBLEM
The present inventors have conducted extensive studies to solve the above problems and as a result, found that unexpectedly excellent herbicidal effects can be obtained by combination of specific compound A and compound B which are
herbicidally active ingredients in the present invention, as compared with a case where the respective compounds are applied individually.
That is, the present invention relates to a herbicidal composition comprising compound A and compound B as herbicidally active ingredients. The present invention further relates to a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the herbicidal composition to the undesired plants or to a place where they grow. The present invention further relates to a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of compound A and a herbicidally effective amount of compound B, to the undesired plants or to a place where they grow.
ADVANTAGEOUS EFFECTS OF INVENTION
The herbicidal composition of the present invention is capable of controlling a wide range of undesired plants emerging in agricultural fields or non-agricultural fields. It surprisingly represents a synergistic effect i.e. a herbicidal effect higher than the mere addition of the respective herbicidal effects of the active ingredients. Such a herbicidal composition of the present invention can be applied at a low dose as compared with a case where the respective active ingredients are applied individually. Thus, it is effective to reduce the environmental load on an area where the composition is applied or a surrounding area thereof.
When the herbicidal activity in a case where two active ingredients are combined, is larger than the simple sum of the respective herbicidal activities of the two active ingredients (the expected activity), it is called a synergistic effect. The activity expected by the combination of two active ingredients can be calculated as follows (Colby S.R., "Weed", vol. 15, p. 20-22, 1967).
Ε = (α+β) - (αβ)/100
where a: growth inhibition rate when treated with x (g/ha) of herbicide X, β: growth inhibition rate when treated with y (g/ha) of herbicide Y,
E: growth inhibition rate expected when treated with x (g/ha) of herbicide X and y
(g/ha) of herbicide Y.
That is, when the actual growth inhibition rate (measured value) is larger than the growth inhibition rate by the above calculation (calculated value), the activity by the combination can be regarded as showing a synergistic effect. The herbicidal composition of the present invention shows a synergistic effect when calculated by the above formula. DESCRIPTION OF EMBODIMENTS
As for compound A, nicosulfuron (common name) is 2-(4,6-dimethoxypyrimidin-2- ylcarbamoylsulfamoyl)-N,N-dimethylnicotinamide.
As for compound B, bicyclopyrone (common name) is 4-hydroxy-3-{2-[(2- methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridylcarbonyl}bicyclo[3.2.1]oct-3-en-2- one.
The salt included in compound A and compound B may be any salt so long as it is agriculturally acceptable. Examples thereof include alkali metal salts such as a sodium salt and a potassium salt; alkaline earth metal salts such as a magnesium salt and a calcium salt; ammonium salts such as a monomethylammonium salt, a dimethylammonium salt and a triethylammonium salt; inorganic acid salts such as a hydrochloride, a perchlorate, a sulfate and a nitrate, and organic acid salts such as an acetate and a methanesulfonate.
The mixing ratio of compound A to compound B cannot generally be defined, as it varies depending upon various conditions such as the type of the formulation, the weather conditions, and the type and the growth stage of the undesired plants, and is, for example, from 7.5:1 to 1 :100, preferably from 4:1 to 1 :30 by the weight ratio.
The herbicidally effective amounts of compounds A and B cannot generally be defined, as they vary depending upon various conditions such as the mixing ratio of the respective compounds, the type of the formulation, the weather conditions, and the type and the growth stage of the undesired plants. However, for example, compound A is applied in an amount of from 5 to 150 g/ha, preferably from 10 to 100 g/ha, and compound B is applied in an amount of from 20 to 500 g/ha, preferably from 25 to 300 g/ha.
The herbicidal composition of the present invention may be applied to undesired plants or may be applied to a place where they grow. Further, it may be applied at any time either before or after the emergence of the undesired plants. Further, the herbicidal composition of the present invention may take various application forms such as soil application, foliar application, irrigation application, and submerged application, and it can be applied to agricultural fields such as upland fields, orchards and paddy fields, and non-cropland such as ridges of fields, fallow fields, play grounds, golf courses, vacant lands, forests, factory sites, railway sides and roadsides.
The herbicidal composition of the present invention can control a wide range of undesired plants such as annual weeds and perennial weeds. The undesired plants to be controlled by the herbicidal composition of the present invention may, for example, be specifically cvperaceae such as sedge (Cyperus spp.) (such as purple nutsedge (Cyperus rotundus L), smallflower umbrella sedge (Cyperus difformis L), yellow nutsedge (Cyperus esculentus L.) or amur cyperus (Cyperus microiria Steud.)) or spikesedge (Kyllinga spp.) (such as green kyllinga (Kyllinqa brevifolia Rottb. var. leiolepis)); gramineae such as barnyard grass (Echinochloa spp.) (such as
barnyardgrass (Echinochloa crus-galli L), early watergrass (Echinochloa oryzicola vasing.) or Japanese millet (Echinochloa utilis Ohwi et Yabuno)), crabgrass (Digitaria spp.) (such as summergrass (Digitaria ciliaris (Retz.) Koel), large crabgrass (Digitaria sanguinalis L), violet crabgrass (Digitaria violascens Link) or Jamaican crabgrass (Digitaria horizontalis Willd.)), goosegrass (Eleusine spp.) (such as goosegrass
(Eleusine indica L.)), ryegrass (Lolium spp-l ijsuch as Italian ryegrass (Lolium
multiflorum Lam.)), foxtail (Setaria spp.) (such as green foxtail (Setaria viridis (L.))), sorghum (Sorghum spp.) (such as johnsongrass (Sorghum halepense (L.) Pers.) or shattercane (Sorghum bicolor (L.) Moench.)), oat (Avena spp.) (such as wild oat
(Avena fatua L.)), brome (Bromus spp.) (such as drooping brome (Bromus tectorum L.) or japanese brome (Bromus japonicus Thunb.)). meadowgrass (Poa spp.) (such as annual bluegrass (Poa annua L.)), foxtail grass (Alopecurus spp.) (such as blackgrass (Alopecurus myosuroides Huds.), shortawn foxtail (Alopecurus aegualis Sobol. var. amurensis)), bermudagrass (Cvnodon dactylon (L.) Pers.), panic grass (Panicum spp.) (such as guinea grass (Panicum maximum Jacq.) or fall panicum (Panicum dichotomiflorum (L.) Michx.)), signal grass (Brachiaria spp.) (such as plantain signal grass (Brachiaria plantaqinea (LINK) Hitchc), palisade signal grass (Brachiaria decumbens Stapf) or mauritius signal grass (Brachiaria mutica (Forssk.) Stapf)), paspalum (Paspalum spp.) (such as dallisgrass (Paspalum dilatatum Poir.) or vasey's grass (Paspalum urvillei Steud.)), itchgrass (Rottboellia spp.) (such as itchgrass (Rottboellia cochinchinensis (LOUR.) W.D.CLAYTON)), or sandbur (Cenchrus spp.) (such as southern sandbur (Cenchrus echinatus L.)); scrophulariaceae such as persian speedwell (Veronica persica Poir.) or corn speedwell (Veronica arvensis L.); compositae such as beggar ticks (Bidens spp.) (such as hairy beggarticks (Bidens pilosa L.), devils berggarticks (Bidens frondosa L.) or Bidens biternata (Lour.) Merr. et Sherff, beggarticks (Bidens subalternans DC.)), hairy fleabane (Convza bonariensis (L.) Cronq.), dandelion (Taraxacum officinale Weber), horseweed (Convza spp.) (such as Canadian horseweed (Convza canadensis (L.) Cronquist)), cocklebur (Xanthium spp.) (such as common cocklebur (Xanthium strumarium L.)), ragweed (Ambrosia spp.) (such as annual ragweed (Ambrosia artemisiifolia L.)), ragwort (Senecio spp.) (such as old-man-in-the-spring (Senecio vulgaris L.)); lequminosae such as rattlepod or rattlebox (Crotalaria spp.) (such as sunn-hemp (Crotalaria juncea L.)), poison bean (Sesbania spp.) (such as rostrate sesbania (Sesbania rostrata Bremek. & Oberm.) or sesbania pea (Sesbania cannabina (Retz.) Pers. )), korean lespedeza (Kummerowia stipulacea (Maxim.) Makino) or white clover (Trifolium repens L.)); carvophvllaceae such as sticky chickweed (Cerastium glomeratum Thuill.) or starwort (Stellaria spp.) (such as common chickweed (Stellaria media L.)); euphorbiaceae such as garden spurge (Euphorbja hirta Lj, thj js^eeded copperleaf (Acalypha australis L.LorJireplant
(Euphorbia heterophylla L.); plantaqinaceae such as asiatic plantain (Plantaqo asiatica L.); oxalidaceae such as creeping woodsorrel (Oxalis corniculata L.); apiaceae such as lawn pennywort (Hvdrocotyle sibthorpioides Lam.); violaceae such as violet (Viola mandshurica W. Becker); iridaceae such as blue-eyedgrass (Sisyrinchium rosulatum Bicknell); qeraniaceae such as Carolina geranium (Geranium carolinianum L.); labiatae such as purple deadnettle (Lamium purpureum L.) or henbit (Lamium amplexicaule L.); malvaceae such as velvetleaf (Abutilon theophrasti MEDIC.) or prickly sida (Sida spinosa L.); convolvulaceae such as ivy-leaved morningglory (Ipomoea hederacea (L.) Jacq.), common morningglory (Ipomoea purpurea ROTH), cypressvine morningglory (Ipomoea quamoclit L), Ipomoea qrandifolia (DAMMERMANN) O'DONNELL. hairy merremia (Merremia aeqyptia (L.) URBAN) or field bindweed (Convolvulus arvensis L); chenopodiaceae such as goosefoot (Chenopodium spp.) (such as common lambsquarters (Chenopodium album L.)); portulacaceae such as common purslane (Portulaca oleracea L); amaranthaceae such as pigweed (Amaranthus spp.) (such as prostrate pigweed (Amaranthus blitoides S. Wats.), livid amaranth (Amaranthus lividus L), purple amaranth (Amaranthus blitum L), smooth pigweed (Amaranthus hybridus L., Amaranthus patulus Bertol.), powell amaranth (Amaranthus powellii S.Wats.), slender amaranth (Amaranthus viridis L), palmer amaranth (Amaranthus palmeri S.Wats.), redroot pigweed (Amaranthus retroflexus L), tall waterhemp (Amaranthus tuberculatus (Moq.) Sauer.), common waterhemp (Amaranthus tamariscinus Nutt.), thomy amaranth (Amaranthus spinosus L.)), ataco (Amaranthus quitensis Kunth.) or roughfruit
amaranth (Amaranthus rudis Sauer.)); solanaceae such as nightshade (Solanum spp.) (such as black nightshade (Solanum nigrum L.)); polvqonaceae such as knotweed
(Polygonum spp.) (such as spotted knotweed (Polygonum lapathifolium L.) or green smartweed (Polygonum scabrum MOENCH)); cruciferae such as flexuous bittercress (Cardamine flexuosa WITH.), or mustard (Sinapis spp.) (such as Charlock (Sinapis arvensis L.)); cucurbitaceae such as burcucumber (Sicyos angulatus L);
commelinaceae such as common dayflower (Commelina communis L); rosaceae such as mock strawberry (Duchesnea chrysantha (Zoll. et Mor. ) Miq.); molluqinacea such as carpetweed (Mollugo verticillata L); or rubiaceae such as false cleavers (Galium spurium var. echinospermon (Wallr.) Hayek) or stickywilly (Galium aparine L).
The herbicidal composition of the present invention is very useful in practical application. For example, the following cases may be mentioned.
(1 ) It has a remarkable synergistic effect, and has a favorable herbicidal activity even if the doses of the respective compounds A and B are small, and accordingly the impact on the surrounding environment can be suppressed.
(2) A herbicidal composition having a long lasting herbicidal effect i.e. a long lasting residual activity, as compared with a case where compound A and compound B are applied individually, may be provided in some cases.
(3) A herbicidal composition having a broad spectrum having high effects against both gramineae and broad leaf weeds, as compared with a case where compound A and compound B are applied individually, may be provided in some cases.
(4) Emergence of herbicide-resistant weeds and weeds having lowered sensitivity to herbicides, may be suppressed in some cases as compared with a case where compound A and compound B are applied individually.
(5) Safety for useful crop plants may be improved in some cases as compared with a case where compound A and compound B are applied individually.
(6) Annual and perennial qramineae such as barnyard grass (Echinochloa spp.), crabgrass (Digitaria spp.), foxtail (Setaria spp.), meadowgrass (Poa spp.), oat (Avena spp.), wildrye (Agropyron spp.), foxtail grass (Alopecurus spp.), goosegrass (Eleusine spp.), itchgrass (Rottboellia spp.), sorghum (Sorghum spp.) and panic grass (Panicum spp.), which are problematic as noxious weeds in agricultural fields, particularly corn fields, can be controlled.
In consideration of the application site of the herbicidal composition or the type or growth state of the undesired plants, the herbicidal composition of the present invention may be mixed with or may be used in combination with other herbicides, fungicides, antibiotics, plant hormones, insecticides, fertilizers, phytotoxicity-reducing agents, etc., in addition to the above active ingredients, without departing from the intention and the scope of the present invention, whereby more excellent effects and activities may sometimes be obtained.
Such other herbicides may, for example, be (1) those which are believed to exhibit herbicidal effects by disturbing hormone activities of plants, (2) those which are believed to exhibit herbicidal effects by inhibiting photosynthesis of plants, (3) those which are believed to be converted to free radicals by themselves to form active oxygen in the plant body and show rapid herbicidal efficacy, (4) those which are believed to exhibit herbicidal effects by inhibiting chlorophyll biosynthesis of plants and abnormally accumulating a photosensitizing peroxide substance in the plant body, (5) those which are believed to exhibit herbicidal effects characterized by bleaching activities by inhibiting chromogenesis of plants such as carotenoids, (6) those which exhibit strong herbicidal effects specifically to gramineous plants, (7) those which are believed to exhibit herbicidal effects by inhibiting an amino acid biosynthesis of plants, (8) those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants, (9) those which are believed to exhibit herbicidal effects by inhibiting protein biosynthesis or lipid biosynthesis of plants, and (10) those which are believed to exhibit herbicidal effects by being parasitic on plants.
The herbicidal composition of the present invention may be prepared by mixing compound A and compound B, as active ingredients, with various agricultural additives in accordance with conventional formulation methods for agricultural chemicals, and applied in various formulations such as dusts, granules, water dispersible granules, wettable powders, tablets, pills, capsules (including a formulation packaged by a water soluble film), water-based suspensions, oil-based suspensions, microemulsions, suspoemulsions, water soluble powders, emulsifiable concentrates, soluble
concentrates or pastes. It may be formed into any formulation which is commonly used in this field, so long as the object of the present invention is thereby met.
At the time of the formulation, compound A and compound B may be mixed together for the formulation, or they may be separately formulated.
The additives to be used for the formulation include, for example, a solid carrier such as kaolinite, sericite, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite or starch; a solvent such as water, toluene, xylene, solvent naphtha, dioxane, dimethylsulfoxide, Ν,Ν-dimethylformamide, dimethylacetamide, N-methyl-2- pyrrolidone or an alcohol; an anionic surfactant such as a salt of fatty acid, a benzoate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyi sulfate, an alkylaryl sulfate, an alkyi diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyi sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenylether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyi ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyi ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, a salt of polyoxyethylene aryl ether phosphoric acid ester, a naphthalene sulfonic acid condensed with formaldehyde or a salt of
alkylnaphthalene sulfonic acid condensed with formaldehyde; a nonionic surfactant such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an
oxyalkylene block polymer, a polyoxyethylene alkyi ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, polyethylene glycol, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil or a polyoxypropylene fatty acid ester; a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil or liquid paraffins; and a transesterified vegetable oil such as methylated rapeseed oil or ethylated rapeseed oil. These additives may suitably be selected for use alone or in combination as a mixture of two or more of them, so long as the object of the present invention is met. Further, additives other than the above-mentioned may be suitably selected for use among those known in this field. For example, various additives commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, an anti-mold agent, a bubble agent, a disintegrator and a binder, may be used. The mix ratio by weight of the active ingredients to such various additives in the herbicidal composition of the present invention may be from 0.001 :99.999 to 95:5, preferably from about 0.005:99.995 to about 90:10.
As a method of applying the herbicidal composition of the present invention, a proper method can be employed among various methods depending upon various conditions such as the application site, the type of the formulation, and the type and the growth stage of the undesired plants to be controlled, and for example, the following methods may be mentioned.
1. Compound A and Compound B are mixed and formulated together, and the formulation is applied as it is.
2. Compound A and Compound B are mixed and formulated together, and the formulation is diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
3. Compound A and Compound B are separately formulated, and the formulations are applied as they are.
4. Compound A and compound B are separately formulated, and as the case requires, the formulations are diluted to predetermined concentrations with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added, and the formulations are applied.
5. Compound A and compound B are separately formulated, and the formulations are mixed when diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
Preferred embodiments of the present invention will be described below, but the present invention is by no means restricted thereto.
(1) A herbicidal composition comprising (a) nicosulfuron or its salt and (b) bicyclopyrone or its salt.
(2) The herbicidal composition according to (1), which comprises (a) and (b) in amounts to show a herbicidally synergistic effect (synergistic herbicidally effective amounts).
(3) The herbicidal composition according to (1), wherein the weight ratio of (a) to (b) is within a range of from 7.5 :1 to 1 :100.
(4) The herbicidal composition according to (1), wherein the weight ratio of (a) to (b) is within a range of from 4:1 to 1 :30.
(5) A method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of a herbicidal composition comprising (a) and (b), to the undesired plants or to a place where they grow.
(6) A method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of (a) and a herbicidally effective amount of (b), to the undesired plants or to a place where they grow.
(7) The method according to (5) or (6), wherein the undesired plants are weeds having lowered sensitivity to herbicidal compounds.
(8) The method according to (5) or (6), wherein the undesired plants are weeds having lowered sensitivity to ALS inhibitors.
(9) The method according to (5) or (6), which comprises applying an amount to show a herbicidally synergistic effect (synergistic herbicidally effective amount) of (a) and an amount to show a herbicidally synergistic effect (synergistic herbicidally effective amount) of (b).
(10) The method according to (5) or (6), wherein (a) is applied in an amount of from 5 to 150 g/ha, and (b) is applied in an amount of from 20 to 500 g/ha.
(11) The method according to (5) or (6), wherein (a) is applied in an amount of from 10 to 100 g/ha, and (b) is applied in an amount of from 25 to 300 g/ha.
(12) The herbicidal composition according to (1), which further contains (c) an additive to be used for the formulation, having no herbicidal effect by itself.
(13) The herbicidal composition according to (12), wherein (c) the additive to be used for the formulation is at least one member selected from the group consisting of a surfactant, a carrier, a solvent, a vegetable oil, a mineral oil and a transesterified vegetable oil.
(14) The herbicidal composition according to (1), which contains none of S- metolachlor, terbuthylazine, prosulfuron and their salts.
(15) The herbicidal composition according to (1), which comprises only (a) and (b) as herbicidally active ingredients. EXAMPLES
Now, the present invention will be described in further detail with reference to Examples. However, the present invention is by no means restricted to such specific Examples.
TEST EXAMPLE 1
Upland field soil was put into a 1/300,000 ha pot, and seeds of wild oat (Avena fatua) L. were sown. On the next day, predetermined amounts of SC agent containing nicosulfuron as an active ingredient (tradename: ONEHOPE NYUZAI, manufactured by Ishihara Sangyo Kaisha, Ltd.) and a wettable powder containing bicyclopyrone prepared by a conventional method, were diluted with water in an amount corresponding to 1 ,000 L/ha, and applied for soil treatment by a small sprayer.
On the 28th day after treatment, the state of growth of the wild oat was visually observed to determine the growth inhibition rate in accordance with the following evaluation standard. The growth inhibition rate (%) (measured value) and the growth inhibition rate (%) (calculated value) calculated by the Colby's formula are shown in Table 1.
Growth inhibition rate (%) = 0 (equivalent to the non-treated area) to 100
(complete kill) TABLE 1
Figure imgf000013_0001
TEST EXAMPLE 2
Upland field soil was put into a 1/300,000 ha pot, and seeds of korean lespedeza
(Kummerowia stipulacea (Maxim.) Makino) were sown. On the next day,
predetermined amounts of ONEHOPE NYUZAI (tradename) and a wettable powder containing bicyclopyrone prepared by a conventional method, were diluted with water in an amount corresponding to 1 ,000 L/ha, and applied for soil treatment by a small sprayer.
On the 28th day after treatment, the state of growth of the korean lespedeza was visually observed to determine the growth inhibition rate. The growth inhibition rate (%) (measured value) and the growth inhibition rate (%) calculated in the same manner as in Test Example 1 are shown in Table 2.
TABLE 2
Figure imgf000013_0002
TEST EXAMPLE 3
Upland field soil was put into a 1/1 ,000,000 ha pot, and seeds of annual ragweed (Ambrosia artemisiifolia L.) were sown. When the annual ragweed reached 6.0 to 8.0-leaf stage, predetermined amounts of ONEHOPE NYUZAI (tradename) and a wettable powder containing bicyclopyrone prepared by a conventional method, were diluted with water in an amount corresponding to 300 LJha, and applied for foliar treatment by a small sprayer.
On the 20th day after treatment, the state of growth of the annual ragweed was visually observed to determine the growth inhibition rate. The growth inhibition rate (%) (measured value) and the growth inhibition rate (%) calculated in the same manner as in Test Example 1 are shown in Table 3.
TABLE 3
Figure imgf000014_0001
INDUSTRIAL APPLICABILITY
According to the present invention, a herbicidal composition having a broad herbicidal spectrum, having high activity and having a long lasting effect can be provided. Further, according to the present invention, broadening of the herbicidal spectrum particularly against gramineae and application to genetically-modified crops resistant to ALS inhibitors are possible, and an increase in the application site can be expected^
The entire disclosure of Japanese Patent Application No. 2012-124118 filed on May 3 , 2012 including specification, claims and summary is incorporated herein by reference in its entirety.

Claims

1. A herbicidal composition comprising (a) nicosulfuron or its salt and (b) bicyclopyrone or its salt.
2. The herbicidal composition according to Claim 1 , wherein the mixing ratio of (a) to (b) is from 7.5:1 to 1 :100 by the weight ratio.
3. The herbicidal composition according to Claim 1 , which controls qramineae, malvaceae, compositae or lequminosae or inhibits their growth.
4. A method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of (a) nicosulfuron or its salt and a herbicidally effective amount of (b) bicyclopyrone or its salt, to the undesired plants or to a place where they grow.
5. The method according to Claim 4, wherein (a) is applied in an amount of from 5 to 150 g/ha, and (b) is applied in an amount of from 20 to 500 g/ha.
6. The method according to Claim 4, wherein the undesired plants are qramineae, malvaceae, compositae or lequminosae.
7. The method according to Claim 4, wherein the undesired plants are annual or perennial qramineae.
8. The method according to Claim 4, wherein the undesired plants are noxious weeds in corn fields.
PCT/JP2013/065635 2012-05-31 2013-05-30 Herbicidal composition comprising nicosulfuron and bicyclopyrone WO2013180309A1 (en)

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