Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION 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
  • A01N47/00—Biocides, 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
  • A01N47/08—Biocides, 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
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/36—Ureas 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
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION 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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

• the present invention relates to a synergistic herbicidal composition
• PTL 1 and PTL 2 disclose herbicidal compositions containing an isoxazoline derivative or its salt and a certain known herbicide, and as examples of the known herbicide, PTL 1 describes nicosulfuron, and PTL 2 describes flazasulfuron, respectively.
• PTL 3 discloses a herbicidal composition containing pyroxasulfone and an acetohydroxyacid synthase inhibitor, and as examples of the acetohydroxyacid synthase inhibitor, Patent Document 3 describes nicosulfuron and flazasulfuron.
• the herbicidal composition comprising (A) at least one member selected from the group consisting of flazasulfuron, nicosulfuron, and their salts and (B) pyroxasulfone or its salt exhibits a synergistic herbicidal effect.
• the present invention relates to a synergistic herbicidal composition
• a synergistic herbicidal composition comprising (A) at least one member selected from the group consisting of flazasulfuron, nicosulfuron, and their salts (hereinafter abbreviated as "Compound A”) and (B) pyroxasulfone or its salt (hereinafter abbreviated as "Compound B”).
• the present invention relates to a method of controlling weeds or inhibiting the growth thereof by applying an effective amount of the foregoing synergistic herbicidal composition to weeds or a place where they grow.
• the present invention relates to a method of controlling weeds or inhibiting the growth thereof by applying synergistic herbicidally effective amounts of Compound A and Compound B to weeds or a place where they grow.
• a herbicidal composition which has a broad weed spectrum, has a high activity, is reduced in an application amount of a herbicidal ingredient, and has a long residual effect can be provided.
• 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).
• ⁇ 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.
• 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.
• flazasulfuron (common name) is l-(4,6- dimethoxypyrimidin-2-yl)-3 -(3 -trilfuoromethyl-2-pyridylsulfonyl)urea, and
• nicosulfuron (common name) is 2-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)- N,N-dimethylnicotinamide.
• pyroxasulfone (common name) is 3-[5- (difluoromethoxy)-l-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5- dihydro-5,5-dimethyl-l,2-oxazole.
• 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
• a mixing ratio of Compound A to Compound B must be properly adjusted depending upon the formulation form, the weather condition, the type and growth state of the weed to be controlled, and the like and cannot be unequivocally defined.
• it is from 27:1 to 1 :50, preferably from 15:1 to 1 :40, and more preferably from 8: 1 to 1 :30 in terms of a Compound A:Compound B weight ratio.
• a mixing ratio of flazasulfuron to Compound B is, for example, from 27:1 to 1 :50, preferably from 15:1 to 1 :40, and more preferably from 8:1 to 1 :30 in terms of a Compound A:Compound B weight ratio.
• a mixing ratio of nicosulfuron to Compound B is, for example, from 15:1 to 1 :50, preferably from 4:1 to 1 :30, and more preferably from 2:1 to 1 :15 in terms of a Compound A.Compound B weight ratio.
• nicosulfuron and pyroxasulfone are mixed in the above ratio of from 2:1 to 1 :15, an especially excellent effect (for example, a synergistic herbicidal effect) is exhibited as compared with other mixing ratios.
• an application amount of each of Compound A and Compound B must be properly adjusted depending upon the mixing ratio of Compound A to Compound B, the formulation form, the weather condition, the type and growth state of the weed to be controlled, and the like and cannot be unequivocally defined.
• the application amount of Compound A is from 10 to 300 g/ha, preferably from 10 to 200 g/ha, and more preferably from 10 to 100 g/ha; and the application amount of Compound B is from 7.5 to 500 g/ha, preferably from 10 to 450 g/ha, and more preferably from 12.5 to 300 g/ha.
• the application amount of Compound A is from 10 to 200 g/ha, preferably from 10 to 150 g/ha, and more preferably from 10 to 100 g/ha; and the application amount of Compound B is from 7.5 to 500 g/ha, preferably from 10 to 400 g/ha, and more preferably from 12.5 to 300 g/ha.
• the application amount of Compound A is from 10 to 300 g/ha, preferably from 15 to 200 g/ha, and more preferably from 20 to 100 g ha; and the application amount of Compound B is from 20 to 500 g ha, preferably from 50 to 450 g ha, and more preferably from 50 to 300 g/ha.
• the herbicidal composition of the present invention may be applied to weeds 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 weeds. 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 broad range of weeds such as annual weeds and perennial weeds.
• the weeds to be controlled by the herbicidal composition of the present invention may, for example, be cvperaceae such as green kyllinga (Cyperus brevifolia var. leiolepis), purple nutsedge (Cyperus rotundus L.), yellow nutsedge (Cyperus esculentus L.), or amur cyperus (Cyperus microiria).
• gramineae such as barnyardgrass (Echinochloa crus-galli L., Echinochloa oryzicola vasing.), crabgrass (Digitaria sanguinalis (L). Scop., Digitaria ischaemum Muhl., Digitaria adscendens Henr., Digitaria microbachne Henr., Digitaria horizontalis Willd.), green foxtail (Setaria viridis L.), goosegrass (Eleusine indica L.), johnsongrass (Sorghum halepense L.), annual bluegrass (Poa annua L.), panic grass (Panicum spp.) guinea grass (Panicum maximum Jacq.), marmeladegrass or signal grass (Brachiaria spp.), Surinam grass (Brachiaria decumbens Stapf), paspalum (Paspalum spp.), itchgrass (Rottboellia cochinchinchinensis (L
• iridaceae such as blue-eyedgrass (Sisyrinchium rosulatum Bicknell); geraniaceae 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 tall morningglory (Ipomoea purpurea L.), or field bindweed (Convolvulus arvensis L.); chenopodiaceae such as common lambsquarters (Chenopodium album L.); portulacaceae such as common purslane (Portulaca oleracea L.); amaranthaceae such as redroot pigweed (Amaranthus retroflexus L.); solanaceae such
• polygonapere such as spotted knotweed (Polygonum lapathifolium L.), or green smartweed (Polygonum scabrum MOENCH); cruciferae such as flexuous bittercress (Cardamine flexuosa WITH.).
• the herbicidal composition of the present invention has advantages such as exhibiting a high control effect on, for example, perennial gramineae such as johnsongrass or paspalum; cyperaceae such as green kyllinga, purple nutsedge, yellow nutsedge or amur cyperus; or inhibiting the growth of weeds for a long time.
• the herbicidal composition of the present invention may further contain one or more other herbicidal compounds in addition to the above-described active ingredients, and there is a case where it is thereby possible to improve e.g. the range of weeds to be controlled, the timing for application of the herbicidal composition, the herbicidal activities, etc. to more desirable ways.
• Such other herbicidal compounds include, for example, the following compounds (common names and the like by ISO, or test codes, here, "under application for approval by ISO” means common), and one or more of them may suitably be selected for use. Even when not specifically mentioned here, in a case where such compounds have salts, alkyl esters, hydrates, different crystal forms, various structural isomers, etc., they are, of course, all included.
• a urea type such as chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, karbutilate, methabenzthiazuron, metoxuron, monolinuron, neburon, siduron, terbumeton, trietazine or metobromuron
• a triazine type such as simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, triaziflam, indaziflam, terbutryn, propazine, metamitron or prometon
• a uracil type such as bromacil, bro
• phenmedipham a hydroxybenzonitrile type such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium or ioxynil- sodium; and others such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole or pentanochlor.
• Quaternary ammonium salt type such as paraquat or diquat, which is believed to be converted to free radicals by itself to form active oxygen in the plant body and shows rapid herbicidal efficacy.
• a photosensitizing peroxide substance in the plant body such as a diphenylether type such as nitrofen, chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen- sodium, oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl (HC-252), fluoroglycofen- ethyl or fluoroglycofen; a cyclic imide type such as chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet or fluthiacet-methyl; and others such as oxadiargyl, oxadiazon, sulfentrazone, carf
• carotenoids such as a pyrid
• aryloxyphenoxypropionic acid type such as diclofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P, fluazifop-P-butyl, haloxyfop-methyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, cyhalofop- butyl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metam
• sulfonylurea type such as chlorimuron- ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, azimsulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron-methyl-sodium, flupyrsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl, halosulfuron, halosulfuron, halosulfuron, halosulfuron, halosulfuron, halosulfuron
• ethoxysulfuron oxasulfuron, ethametsulfuron, ethametsulfuron-methyl, iodosulfuron, iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron, tritosulfuron, foramsulfuron, trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron- methyl, mesosulfuron, orthosulfamuron, flucetosulfuron, amidosulfuron,
• propyrisulfuron TH-547
• metazosulfuron or a compound disclosed in the claim of WO2005092104
• a triazolopyrimidinesulfonamide type such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam or pyroxsulam
• an imidazolinone type such as imazapyr, imazapyr-isopropylammonium, imazethapyr, imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox- ammonium, imazamethabenz, imazamethabenz-methyl or imazapic
• a triazolopyrimidinesulfonamide type such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam or p
• pyrimidinylsalicylic acid type such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid or pyrimisulfan; a
• sulfonylaminocarbonyltriazolinone type such as flucarbazone, flucarbazone-sodium, propoxycarbazone-sodium, propoxycarbazone or thiencarbazone; and others such as glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate-isopropylammonium, glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodiuni, bilanafos, bilanafos-sodium or cinmethylin.
• Those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants such as a dinitroaniline type such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, butralin or dinitramine; an amide type such as bensulide, napropamide, propyzamide or pronamide; an organic compound having a dinitroaniline type such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, butralin or dinitramine; an amide type such as bensulide, napropamide, propyzamide or pronamide; an organic
• phosphorus type such as arniprofos-methyl, butamifos, anilofos or piperophos
• a phenyl carbamate type such as propham, chlorpropham, barban or carbetamide
• a cumylamine type such as daimuron, cumyluron, bromobutide or methyldymron
• others such as asulam, asulam-sodium, dithiopyr, thiazopyr, chlorthal-dimethyl, chlorthal or diphenamid.
• a chloroacetamide type such as alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, thenylchlor, pethoxamid, acetochlor, propachlor, dimethenamid, dimethenamid-P, propisochlor or dimethachlor
• a thiocarbamate type such as molinate, dimepiperate, pyributicarb, EPTC, butylate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, thiobencarb, diallate, tri-allate or orbencarb; and others such as etobenzanid, mefenacet, flufenacet, tridiphane, cafenstrole, fentrazamide, oxaziclomef
• MSMA, DSMA, CMA endothall, endothall-dipotassium, endothall- sodium, endothall-mono(N,N-dimethylalkylammonium), ethofumesate, sodium chlorate, pelargonic acid (nonanoic acid), fosamine, fosamine-ammonium, pinoxaden, ipfencarbazone (HOK-201), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid, dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, ferrous sulfate, flupropanate, flupropanate-sodium, isoxaben, mefiuidide, mefluidide-diolamine, metam,
• 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.
• Compound A and Compound B may be mixed together for the formulation, or they may be separately formulated and then mixed for application.
• 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 alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl 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 alkyl 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; and a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil,
• 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 ingredient to such various additives of the herbicidal composition of the present invention may be from 0.001 :99.999 to 95:5, preferably from 0.005:99.995 to 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 noxious plants to be controlled, and for example, the following methods may be mentioned.
• Compound A and Compound B are formulated together, and the formulation is applied as it is. 2. Compound A and Compound B are formulated together, 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 they are 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, respectively.
• 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
• Preferred embodiments of the present invention are hereunder described, but it should not be construed that the present invention is limited thereto.
• a synergistic herbicidal composition comprising (A) flazasulfuron or its salt and (B) pyroxasulfone or its salt.
• composition as set forth above in (1) wherein a mixing ratio of (A) flazasulfuron or its salt to (B) pyroxasulfone or its salt is from 8:1 to 1 :12 in terms of a (A):(B) weight ratio.
• a method of controlling an undesirable plant or inhibiting the growth thereof comprising applying an effective amount of a synergistic herbicidal composition containing (A) flazasulfuron or its salt and (B) pyroxasulfone or its salt to an undesirable plant or a place where it grows.
• a method of controlling an undesirable plant or inhibiting the growth thereof comprising applying synergistic herbicidally effective amounts of (A) flazasulfuron or its salt and (B) pyroxasulfone or its salt to an undesirable plant or a place where it grows.
• a synergistic herbicidal composition comprising (A) nicosulfuron or its salt and (B) pyroxasulfone or its salt.
• a method of controlling an undesirable plant or inhibiting the growth thereof comprising applying an effective amount of a synergistic herbicidal composition comprising (A) nicosulfuron or its salt and (B) pyroxasulfone or its salt to an
• a method of controlling an undesirable plant or inhibiting the growth thereof comprising applying synergistic herbicidally effective amounts of (A) nicosulfuron or its salt and (B) pyroxasulfone or its salt to an undesirable plant or a place where it grows.
• (A) nicosulfuron or its salt is applied in an amount of from 10 to 300 g/ha
• (B) pyroxasulfone or its salt is applied in an amount of from 20 to 500 g/ha.
• Upland field soil was put into a 1/1 ,000,000-ha pot, and seeds of common lambsquarters (Chenopodium album L.) were sown. After one day, prescribed amounts of a water-based suspension containing nicosulfuron as an active ingredient and a wettable powder containing pyroxasulfone as an active ingredient were diluted with water (corresponding to 300 L/ha) and applied for soil treatment by a small sprayer.
• Test Example 6 Upland field soil was put into a 1/300,000-ha pot, and seeds of wild oat (Ayena fatua L.) were sown. After one day, prescribed amounts of SHIBAGEN DF (trade name) and a wettable powder containing pyroxasulfone as an active ingredient were diluted with water (corresponding to 1 ,000 L/ha) and applied for soil treatment by a small sprayer.
• SHIBAGEN DF trade name
• a wettable powder containing pyroxasulfone as an active ingredient
• a herbicidal composition having a broad weed spectrum and having a high activity and a long residual effect can be provided.

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