WO2012057743A1 - Synergistic herbicidal composition containing fluroxypyr and quinclorac - Google Patents

Synergistic herbicidal composition containing fluroxypyr and quinclorac Download PDF

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Publication number
WO2012057743A1
WO2012057743A1 PCT/US2010/054232 US2010054232W WO2012057743A1 WO 2012057743 A1 WO2012057743 A1 WO 2012057743A1 US 2010054232 W US2010054232 W US 2010054232W WO 2012057743 A1 WO2012057743 A1 WO 2012057743A1
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WO
WIPO (PCT)
Prior art keywords
quinclorac
fluroxypyr
mixture
herbicidal
vegetation
Prior art date
Application number
PCT/US2010/054232
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English (en)
French (fr)
Inventor
Richard Mann
Ändrea MCVEIGH-NELSON
Original Assignee
Dow Agrosciences Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to RU2013123996/13A priority Critical patent/RU2539937C2/ru
Priority to JP2013536571A priority patent/JP5764662B2/ja
Priority to MYPI2013700659A priority patent/MY183729A/en
Priority to CN201080070962.4A priority patent/CN103281899B/zh
Priority to AU2010363056A priority patent/AU2010363056B2/en
Priority to BR112013010388-4A priority patent/BR112013010388B1/pt
Application filed by Dow Agrosciences Llc filed Critical Dow Agrosciences Llc
Priority to PCT/US2010/054232 priority patent/WO2012057743A1/en
Priority to EP10773803.1A priority patent/EP2632262A1/en
Priority to KR1020137013312A priority patent/KR101787355B1/ko
Priority to UAA201306490A priority patent/UA105451C2/uk
Publication of WO2012057743A1 publication Critical patent/WO2012057743A1/en
Priority to CR20130176A priority patent/CR20130176A/es

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as "synergism.”
  • synergism As described in the Herbicide Handbook of the Weed Science Society of America, Eighth Edition, 2002, p. 462 "'synergism' [is] an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response to each factor applied separately.”
  • the present invention is based on the discovery that fluroxypyr and quinclorac, already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination.
  • the present invention concerns a synergistic herbicidal mixture comprising an herbicidally effective amount of (a) fluroxypyr and (b) quinclorac.
  • the composition may also contain an agriculturally acceptable adjuvant and/or carrier.
  • the present invention also concerns herbicidal compositions for and methods of controlling the growth of undesirable vegetation, particularly in monocot crops including rice, wheat, barley, oats, rye, sorghum, corn, maize, pastures, grasslands, rangelands, fallowland, turf, IVM and aquatics and the use of these synergistic compositions.
  • quinclorac The species spectrum of quinclorac is broad and highly complementary with that of fluroxypyr.
  • a combination of quinclorac and fluroxypyr exhibits a synergistic action in the control of barnyardgrass (Echinochloa crus- galli; ECHCG), Chinese sprangletop (Leptochloa chinensis; LEFCH) and broadleaf signalgrass ⁇ Brachiaria platyphylla; BRAPP) at application rates equal to or lower than the rates of the individual compounds.
  • ECHCG barnyardgrass
  • Chinese sprangletop Chinese sprangletop
  • LEFCH Chinese sprangletop
  • LEFCH broadleaf signalgrass ⁇ Brachiaria platyphylla
  • BRAPP broadleaf signalgrass
  • Quinclorac is the common name for 3,7-dichloro-8-quinolinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Quinclorac controls Echinochloa spp., Brachiaria spp., Digitaria spp. and many broadleaf weeds in rice and turf.
  • the term herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
  • An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation, and the like.
  • plants and vegetation include germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation.
  • Herbicidal activity is exhibited by the compounds of the synergistic mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote non-selective or selective herbicidal action.
  • composition of the present invention postemergence to relatively immature undesirable vegetation to achieve the maximum control of weeds.
  • the weight ratio of fluroxypyr as measured in grams acid equivalent per hectare (g ae/ha) to quinclorac as measured in grams active ingredient per hectare (g ai/ha) at which the herbicidal effect is synergistic lies within the range of between 1 : 11 and 22: 1.
  • the rate at which the synergistic composition is applied will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application.
  • Quinclorac is applied at a rate between 26 g ai/ha and 560 g ai/ha
  • fluroxypyr is applied at a rate between 50 g ae/ha and 560 g ae/ha.
  • the components of the synergistic mixture of the present invention can be applied either separately or as part of a multipart herbicidal system, which can be provided as a premix or a tank mix.
  • the synergistic mixture of the present invention can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation.
  • the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides.
  • Some of the herbicides that can be employed in conjunction with the synergistic composition of the present invention include: 2,4-D, acetochlor, acifluorfen, aclonifen, AE0172747, alachlor, amidosulfuron,
  • diflufenzopyr dimethenamid, dimethenamid-p, diquat, dithiopyr, diuron, EK2612, EPTC, esprocarb, ET-751, ethoxysulfuron, ethbenzanid, F7967, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-ethyl + isoxadifen-ethyl, fentrazamide, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, flucetosulfuron (LGC-42153), flufenacet, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, flupyrsulfuron, fomesafen, foramsulfuron, fumiclorac, glufosinate, glufo
  • pyroxasulfone (KIH-485), quizalofop-ethyl-D, S-3252, sethoxydim, simazine, SL-0401, SL- 0402, S-metolachlor, sulcotrione, sulfentrazone, sulfosate, tebuthiuron, tefuryltrione (AVH- 301), terbacil, thiazopyr, thiobencarb, triclopyr, trifluralin and tritosulfuron.
  • the synergistic composition of the present invention can, further, be used in conjunction with glyphosate, glufosinate, dicamba, imidazolinones, sulfonylureas, or 2,4-D on glyphosate-tolerant, glufosinate-tolerant, dicamba-tolerant, imidazolinone-tolerant, sulfonylurea-tolerant and 2,4-D-tolerant crops. It is generally preferred to use the synergistic composition of the present invention in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. It is further generally preferred to apply the synergistic composition of the present invention and other complementary herbicides at the same time, either as a combination formulation or as a tank mix.
  • the synergistic composition of the present invention can generally be employed in combination with known herbicide safeners, such as benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, mefenpyr-diethyl, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
  • herbicide safeners such as benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil,
  • Cloquintocet is a particularly preferred safener for the synergistic compositions of the present invention, specifically antagonizing any harmful effect of the synergistic compositions on rice and cereals.
  • Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients.
  • Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions.
  • Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art.
  • Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C 9 -Cn
  • alkylpolyglycoside phosphated alcohol ethoxylate; natural primary alcohol (C 12 -C 16 ) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;
  • Liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2- pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for the dilution of concentrates.
  • Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like. It is usually desirable to incorporate one or more surface-active agents into the compositions of the present invention. Such surface-active agents are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application.
  • the surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
  • Surfactants conventionally used in the art of formulation and which may also be used in the present formulations are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980- 81.
  • Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate;
  • alkylphenol-alkylene oxide addition products such as nonylphenol-Cig ethoxylate
  • alcohol-alkylene oxide addition products such as tridecyl alcohol-Ci6 ethoxylate
  • soaps such as sodium stearate
  • alkylnaphthalene-sulfonate salts such as sodium dibutyl- naphthalenesulfonate
  • dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate
  • sorbitol esters such as sorbitol oleate
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • salts of mono and dialkyl phosphate esters such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut
  • compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
  • the concentration of the active ingredients in the synergistic composition of the present invention is generally from 0.001 to 98 percent by weight. Concentrations from 0.01 to 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration from 1 to 98 weight percent, preferably 5 to 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application, or applied as a dry or liquid formulation directly into flooded rice fields. The diluted compositions usually applied to weeds or the locus of weeds generally contain 0.0001 to 10 weight percent active ingredient and preferably contain 0.001 to 5.0 weight percent. The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
  • Seeds of the desired test plant species were planted in 80% mineral soil/20% grit planting mixture, which typically has a pH of 7.2 and an organic matter content of 2.9 percent, in plastic pots with a surface area of 128 square centimeters (cm 2 ).
  • the growing medium was steam sterilized.
  • the plants were grown for 7-19 days in a greenhouse with an approximate 14-hour (h) photoperiod which was maintained at 29 °C during the day and 26 °C during the night.
  • Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary.
  • the plants were treated with postemergence foliar applications when they reached the third to fourth true leaf stage. All treatments were applied using a randomized complete block trial design, with 4 replications per treatment.
  • Treatments consisted of the compounds as listed in Table 1 for each compound applied alone and in combination.
  • Formulated amounts of quinclorac and fluroxypyr-meptyl ester were placed in 60 milliliter (mL) glass vials and dissolved in a volume of 60 mL of a water solution containing Agri-dex crop oil concentrate in a 1% volume per volume (v/v) ratio.
  • Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha).
  • Spray solutions of the mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingredients in single and two way combinations.
  • Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha at a spray height of 18 inches (43 centimeters (cm)) above average plant canopy.
  • the treated plants and control plants were placed in a greenhouse as described above and watered by sub -irrigation to prevent wash-off of the test compounds. Treatments were rated at 21 days after application (DAA) as compared to the untreated control plants. Visual weed control was scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
  • Table 1 demonstrates the herbicidal synergistic efficacy of quinclorac + fluroxypyr- meptyl tank mixes on weed control. All treatment results, both for the single product and mixtures, are an average of 4 replicates evaluated at 21 days after application, and the tank mix interactions are significant at the P>0.05 level.
  • Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967, 15, 20-22.). The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
  • A observed efficacy of active ingredient A at the same concentration as used in the mixture.
  • B observed efficacy of active ingredient B at the same concentration as used in the mixture.
  • Rates of quinclorac are expressed in grams active ingredient/hectare (g ai/ha) and rates of fluroxypyr are expressed in grams acid equivalent per hectare (g ae/ha) in Table 1.
  • g ai/ha grams active ingredient per hectare
  • g ae/ha grams acid equivalent per hectare

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  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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PCT/US2010/054232 2010-10-27 2010-10-27 Synergistic herbicidal composition containing fluroxypyr and quinclorac WO2012057743A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
JP2013536571A JP5764662B2 (ja) 2010-10-27 2010-10-27 フルロキシピルおよびキンクロラックを含有する相乗的除草剤組成物
MYPI2013700659A MY183729A (en) 2010-10-27 2010-10-27 Synergistic herbicidal composition containing fluroxypyr and quinclorac
CN201080070962.4A CN103281899B (zh) 2010-10-27 2010-10-27 包含氯氟吡氧乙酸和二氯喹啉酸的协同性除草组合物
AU2010363056A AU2010363056B2 (en) 2010-10-27 2010-10-27 Synergistic herbicidal composition containing fluroxypyr and quinclorac
BR112013010388-4A BR112013010388B1 (pt) 2010-10-27 2010-10-27 Mistura e composição herbicidas sinérgicas, e método para controlar vegetação indesejável
RU2013123996/13A RU2539937C2 (ru) 2010-10-27 2010-10-27 Синергическая гербицидная композиция, содержащая флуроксипир и квинклорак
PCT/US2010/054232 WO2012057743A1 (en) 2010-10-27 2010-10-27 Synergistic herbicidal composition containing fluroxypyr and quinclorac
EP10773803.1A EP2632262A1 (en) 2010-10-27 2010-10-27 Synergistic herbicidal composition containing fluroxypyr and quinclorac
KR1020137013312A KR101787355B1 (ko) 2010-10-27 2010-10-27 플루록시피르 및 퀸클로락을 함유하는 상승작용적 제초제 조성물
UAA201306490A UA105451C2 (uk) 2010-10-27 2010-10-27 Синергічна гербіцидна композиція, яка містить флуроксипір і квінклорак
CR20130176A CR20130176A (es) 2010-10-27 2013-04-23 Composicion herbicida sinergica de fluroxipir y quinclorac

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PCT/US2010/054232 WO2012057743A1 (en) 2010-10-27 2010-10-27 Synergistic herbicidal composition containing fluroxypyr and quinclorac

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WO2012057743A1 true WO2012057743A1 (en) 2012-05-03

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EP (1) EP2632262A1 (uk)
JP (1) JP5764662B2 (uk)
KR (1) KR101787355B1 (uk)
CN (1) CN103281899B (uk)
AU (1) AU2010363056B2 (uk)
BR (1) BR112013010388B1 (uk)
CR (1) CR20130176A (uk)
MY (1) MY183729A (uk)
RU (1) RU2539937C2 (uk)
UA (1) UA105451C2 (uk)
WO (1) WO2012057743A1 (uk)

Cited By (10)

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WO2017009144A1 (en) * 2015-07-10 2017-01-19 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
US10897898B2 (en) 2015-07-10 2021-01-26 BASF Agro B.V. Herbicidal composition comprising cinmethylin and acetochlor or pretilachlor
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
US11116213B2 (en) 2015-07-10 2021-09-14 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pethoxamid
US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
US11517018B2 (en) 2015-07-10 2022-12-06 BASF Agro B.V. Herbicidal composition comprising cinmethylin and saflufenacil

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AR100785A1 (es) * 2014-06-09 2016-11-02 Dow Agrosciences Llc Control herbicida de maleza a partir de combinaciones de fluroxipir e inhibidores de als
CN104542663A (zh) * 2014-12-23 2015-04-29 江西中迅农化有限公司 氯吡嘧磺隆和二氯喹啉酸及氯氟吡氧乙酸的除草组合物
CN106376568A (zh) * 2016-10-19 2017-02-08 陕西上格之路生物科学有限公司 一种三元除草组合物
CN106577671A (zh) * 2016-10-31 2017-04-26 浙江天丰生物科学有限公司 一种含有氰氟草酯、氯氟吡氧乙酸异辛酯和二氯喹啉酸的协同除草组合物
CN109964946A (zh) * 2019-04-08 2019-07-05 河南瀚斯作物保护有限公司 一种含有莠去津、二氯喹啉酸和氯氟吡氧乙酸的除草组合物

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US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
CN107846892A (zh) * 2015-07-10 2018-03-27 巴斯夫农业公司 包含环庚草醚和特异性喹啉羧酸的除草组合物
AU2016292677B2 (en) * 2015-07-10 2020-09-24 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
US10897898B2 (en) 2015-07-10 2021-01-26 BASF Agro B.V. Herbicidal composition comprising cinmethylin and acetochlor or pretilachlor
WO2017009144A1 (en) * 2015-07-10 2017-01-19 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US11116213B2 (en) 2015-07-10 2021-09-14 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pethoxamid
US11206827B2 (en) 2015-07-10 2021-12-28 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
US11517018B2 (en) 2015-07-10 2022-12-06 BASF Agro B.V. Herbicidal composition comprising cinmethylin and saflufenacil
CN107846892B (zh) * 2015-07-10 2024-02-20 巴斯夫农业公司 包含环庚草醚和特异性喹啉羧酸的除草组合物

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AU2010363056A1 (en) 2013-05-02
CR20130176A (es) 2013-09-18
KR101787355B1 (ko) 2017-10-19
BR112013010388A2 (pt) 2016-07-05
JP2013540811A (ja) 2013-11-07
MY183729A (en) 2021-03-10
JP5764662B2 (ja) 2015-08-19
CN103281899B (zh) 2015-04-08
RU2013123996A (ru) 2014-12-10
RU2539937C2 (ru) 2015-01-27
UA105451C2 (uk) 2014-05-12
KR20130126922A (ko) 2013-11-21

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