WO2014181281A1 - Mélange herbicide d'imazethapyr et de propaquizafop - Google Patents

Mélange herbicide d'imazethapyr et de propaquizafop Download PDF

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Publication number
WO2014181281A1
WO2014181281A1 PCT/IB2014/061291 IB2014061291W WO2014181281A1 WO 2014181281 A1 WO2014181281 A1 WO 2014181281A1 IB 2014061291 W IB2014061291 W IB 2014061291W WO 2014181281 A1 WO2014181281 A1 WO 2014181281A1
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WO
WIPO (PCT)
Prior art keywords
mixture
imazethapyr
propaquizafop
herbicidal
amount
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Ceased
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PCT/IB2014/061291
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English (en)
Inventor
Josef GOLDSHMIDT
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Adama Quena NV
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Quena Plant Protection NV
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Filing date
Publication date
Application filed by Quena Plant Protection NV filed Critical Quena Plant Protection NV
Priority to BR112015028146A priority Critical patent/BR112015028146A2/pt
Priority to UAA201512066A priority patent/UA119849C2/uk
Priority to RU2015151447A priority patent/RU2656400C2/ru
Publication of WO2014181281A1 publication Critical patent/WO2014181281A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines

Definitions

  • the present subject matter relates to a herbicidal mixture for controlling undesired vegetation. Specifically, the present subject matter relates to a herbicidal mixture comprising a synergistic combination of propaquizafop and imazethapyr.
  • Mixtures of selected herbicides have several advantages over the use of a single herbicide including (a) an increase in the spectrum of weeds controlled or an extension of weed control over a longer period of time, (b) an improvement in crop safety by using minimum doses of selected herbicides applied in combination rather than a single high dose of one herbicide and (c) a delay in the appearance of resistant weed species to selected herbicides ⁇ Int. J. Agri. Biol., Vol. 6, No. 1, 2004, pages 209-212).
  • Propaquizafop ((R)-2- [[( 1 -methylethylidene)amino] oxyjethyl 2- [4- [(6-chloro-2- quinoxalinyl)oxy]phenoxy]propanoate), disclosed in US4545807, is a Fatty acid synthesis inhibitor which inhibits acetyl CoA carboxylase (ACCase). It is a systemic post-emergence herbicide absorbed by foliage and roots, and translocated throughout the plant.
  • ACCase acetyl CoA carboxylase
  • Propaquizafop is used for the control of a wide range of annual and perennial grasses (including Sorghum halepense, Agropyron repens and Cynodon dactylon) in soya beans, cotton, sugar beet, potatoes, peanuts, peas, oilseed rape and vegetables.
  • grasses including Sorghum halepense, Agropyron repens and Cynodon dactylon
  • Imazethapyr (R5)-5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) nicotinic acid, disclosed in US 4,798,619, is a branched chain amino acid synthesis (ALS or AHAS) inhibitor. Hence reduces levels of valine, leucine and isoleucine, leading to disruption of protein and DNA synthesis.
  • Imazethapyr is a systemic herbicide, absorbed by the roots and foliage. Imazethapyr control many major annual and perennial grass and broad leaved weeds.
  • the subject matter relates to a herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.
  • the weight ratio of imazethapyr to propaquizafop may be from 20: 1 to 1:20
  • the weight ratio of imazethapyr to propaquizafop may be from 5: 1 to 1 :5.
  • the compounds of the mixture may be applied jointly or in a succession.
  • the application rate of the mixture may be from 0.1 liter/ha to 10 liter/ha. In a specific embodiment, the application rate of the mixture may be 1.25 liter/ha.
  • the mixture may be applied in an amount of 125 g/ha.
  • the amount of imazethapyr to be applied may be 75 g/ha and the amount of propaquizafop may be 50 g/ha.
  • composition comprising imazethapyr and propaquizafop, esters, salts or combination thereof and at least one agriculturally acceptable carrier.
  • the composition may further include at least one surfactant, solid diluent, liquid diluent, or a combination thereof.
  • a method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of the mixture comprising imazethapyr, propaquizafop esters, salts and/or combination thereof.
  • the crop may be selected from the group consisting of soybeans, blackgram, peanuts, green gram, pigeon pea, beans, field peas and cluster beans.
  • the mixture may be applied in an amount of 1 to 500 g/ha. In a preferred embodiment, the mixture may be applied in an amount of 125 g/ha.
  • the undesired vegetation may be selected from the group consisting of
  • Echinochloa Colona Dinebra Arabica, Cynotis sp, Eleusine Indica, Cynodon Dactylon, Euphorbia Hirta, Amaranthus Viridis, Digeria Arvensis, Digera sp., Panicum sp., Phyllanthus sp, Commelina benghalensis L, Parthenium, Trianthema Portulacasturm, Cleome viscosa, Digera arvensis, Parthenium hysterophorus, Cynadon dactylone, Commelina bengalensis and Dinebra sp., Portulaca sp., Trianthima sp., Dactyloctenium aegyptium, Corchprus sp., Trianthema monogyna, Brachiaria sp.
  • a method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of the composition comprising imazethapyr, propaquizafop esters, salts and/or combination thereof.
  • synergistic mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.
  • crop includes reference to whole plant, plant organ (e.g., leaves, stems, twigs, roots, trunks, limbs, shoots, fruits etc.), or plant cells.
  • locus includes not only areas where weeds may already be growing, but also areas where weeds have yet to emerge, and also to areas under cultivation.
  • agriculturally acceptable carrier means carriers of which are known and accepted in the art for the formation of formulations for agricultural or horticultural use.
  • surfactant refers to an agriculturally acceptable material which imparts emulsifiability, stability, spreading, wetting, dispersibility or other surface-modifying properties.
  • the present subject matter relates to a herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.
  • An embodiment relates to a synergistic herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.
  • the weight ratio of imazethapyr to propaquizafop in the mixture may be from about 50: 1 to 1 :50.
  • the weight ratio of imazethapyr to propaquizafop may be from about 20: 1 to 1:20.
  • the weight ratio of imazethapyr to propaquizafop may be from about 5: 1 to 1 :5.
  • the weight ratio of imazethapyr to propaquizafop may be from about 1.75: 1 to 1 : 1.75.
  • the weight ratio of imazethapyr to propaquizafop may be from about 1.5: 1 to 1 : 1.5. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 1.4: 1 to 1 :1.4. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 1.2: 1 to 1: 1.2.
  • the weight ratio of imazethapyr to propaquizafop may be about 1.1 :1.
  • composition comprising imazethapyr and propaquizafop including esters and salts thereof and an agriculturally acceptable carrier, is provided.
  • composition comprising at least one additional component selected from the group of surfactants, solid diluents and liquid diluents.
  • the herbicidal compositions and herbicidal mixtures may be applied jointly or in a succession.
  • compositions may include additional other crop protection agents, for example pesticides, safeners or agents for controlling phytopathogenic fungi or bacteria.
  • the herbicidal mixture may be applied in an amount of about 0.1 to 500 liter/ha. In yet another embodiment, the herbicidal mixture may be applied in an amount of about 0.1 to 100 liter/ha. In another embodiment, the herbicidal may be applied in an amount of about 0.1 to 10 liter/ha. In a specific embodiment, the mixture may be applied in an amount of about 1.25 liter/ha (equal to 0.50 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 1.35 liter/ha (equal to 0.55 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 1.50 liter/ha (equal to 0.60 liter/acre).
  • the mixture may be applied in an amount of about 2.00 liter/ha (equal to 0.80 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 2.25 liter/ha (equal to 0.90 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 2.50 liter/ha (equal to 1.00 liter/acre).
  • the herbicidal mixture may be applied in an amount of about 1 to 1000 g/ha. In another embodiment, the herbicidal mixture may be applied in an amount of about 1 to 500 g/ha. In a specific embodiment, the mixture may be applied in an amount of about 125 g/ha. Correspondingly, the amount of imazethapyr is about 75 g/ha and propaquizafop is about 50 g/ha.
  • a method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of a mixture of imazethapyr and propaquizafop, esters, salts and/or combination thereof, is provided.
  • the mixtures and/or the herbicidal compositions may be applied pre-plant incorporated, pre- or post-emergence.
  • the mixture may be applied on crops which include soybeans, blackgram, peanuts, green gram, pigeon pea, cluster beans, field peas, mung beans, dry beans, peanuts, groundnuts, snap bean, alfalfa, lettuce, beans.
  • crops which include soybeans, blackgram, peanuts, green gram, pigeon pea, cluster beans, field peas, mung beans, dry beans, peanuts, groundnuts, snap bean, alfalfa, lettuce, beans.
  • the crop includes soybeans, groundnuts, blackgram, peanuts, green gram, pigeon pea, beans, field peas and cluster beans.
  • the mixture may be applied on tolerant or resistant mutants or transgenic crops plants such as soybean, and etc.
  • the undesired vegetation may include Hibiscus trionum,
  • the undesired vegetation may include Echinochloa Colona, Dinebra Arabica, Cynotis sp, Eleusine Indica, Cynodon Dactylon, Euphorbia Hirta, Amaranthus Viridis, Digeria Arvensis, Digera sp., Panicum sp., Phyllanthus sp, Commelina benghalensis L, Parthenium, Trianthema Portulacasturm, Cleome viscosa, Digera arvensis, Parthenium hysterophorus, Cynadon dactylone, Commelina bengalensis and Dinebra sp., Portulaca sp., Trianthima sp., Dactyloctenium aegyptium, Corchprus sp., Trianthema monogyna, Brachiaria sp.
  • compositions may be made at the time of use, or diluted, or else they can be concentrated compositions, or so-called "ready-to-use" compositions, that is to say, ready for marketing.
  • the formulation may be obtained by combining a synergistic amount of the active ingredients with an agriculturally acceptable carrier, a surfactant or other application-promoting adjuvant customarily employed in formulation technology.
  • the composition may be employed in any conventional form, for example, in the form of a twin pack, or as emulsion concentrates (EC), microemulsion concentrates (MEC), suspension concentrates (SC), soluble concentrates (SL), suspoemulsion (SE), oil dispersions (OD), water dispersible granules (WDG), water soluble granules (SG) and wettable powders (WP).
  • EC emulsion concentrates
  • MEC microemulsion concentrates
  • SC suspension concentrates
  • SL soluble concentrates
  • SE suspoemulsion
  • OD oil dispersions
  • WDG water dispersible granules
  • SG water soluble granules
  • WP wettable powders
  • Such compositions can be formulated using with agriculturally acceptable carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology and formulation techniques that are known in the art.
  • the composition of imazethapyr and propaquizafop is an emulsion concentrate, preferably a microemulsion.
  • the amount of the mixture of active ingredient in the composition may be about 0.1-99 wt. , specifically about 0.1-95 wt. , more specifically about 0.1-90 wt. , based on the total weight of the composition. In another embodiment, the amount of the mixture of active ingredient in the composition may be about 0.1-50 wt , specifically about 0.1-25 wt. , more specifically about 0.1-10 wt. , based on the total weight of the composition.
  • suitable liquid carriers to be used in the composition may include water, aromatic hydrocarbons such as alkylbenzenes and alkylnaphthalenes, alcohols such as methanol, cyclohexanol and decanol, ethylene glycol, polypropylene glycol and dipropropylene glycol, N,N-dimethylformamide, dimethylsulfoxide, N- alkylpyrrolidone, paraffins, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone and the like.
  • aromatic hydrocarbons such as alkylbenzenes and alkylnaphthalenes
  • alcohols such as methanol, cyclohexanol and decanol
  • ethylene glycol polypropylene glyco
  • suitable solid carriers to be used in the composition may include mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, sodium carbonate and bicarbonate, and sodium sulfate, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, sodium carbonate and bi
  • Suitable surfactants include non-ionic, anionic, cationic and ampholytic types such as alkoxylated fatty alcohols, ethoxylated polysorbate (e.g. tween 20), ethoxylated castor oil, lignin sulfonates, fatty acid sulfonates (e.g.
  • phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styrylphenol ethoxylates, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, alkylarylsulfonates, ethoxylated alkylphenols and aryl phenols, polyalkylene glycols and sorbitol esters.
  • phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styrylphenol ethoxylates, condensates of sulfonated naphthalene and naphthalene derivatives with formaldeh
  • ingredients such as wetting agents, anti-foaming, adhesives, neutralizers, thickeners, binders, sequestrants, stabilizers, solubilizer, salts, fertilizers or anti-freeze agents, may also be added to the disclosed compositions.
  • kits comprising the herbicidal mixture as described herein, or components thereof, is provided.
  • Such kits may comprise, in addition to the aforementioned active components, one or more additional active and/or inactive ingredients, either within the provided herbicidal composition or separately.
  • Certain kits comprise imazethapyr, propaquizafop, each in a separate container, and each optionally combined with a carrier.
  • synergistic effect exists wherever the action of a combination of active components is greater than the sum of the action of each of the components alone. Therefore, a synergistically effective amount (or an effective amount of a synergistic composition or combination) is an amount that exhibits greater pesticidal activity than the sum of the pesticidal activities of the individual components.
  • E represents the expected percentage of pesticidal control for the combination of the two pesticides at defined doses (for example equal to x and y respectively)
  • X is the percentage of herbicidal control observed by imazethapyr at a defined dose (equal to x)
  • Y is the percentage of herbicidal control observed by propaquizafop at a defined dose (equal to y).
  • the above formulation was prepared by forming a mixture comprising 37.5 g of imazethapyr, the surfactants, the additives and dipropylene glycol, propylene glycol and water as solvents. Afterwards, a premix of 25 g of propaquizafop dissolved in Solgad 200 ULN was added to the mixture. This was then stirred until a homogeneous mixture was obtained.
  • the experiments were conducted by tank mixing commercially available Agil (propaquizafop 10% EC, 100 gr/L) and commercially available Weedlock (imazethapyr 10% SL, 100 gr/L) on soybean, black gram, ground nut (peanut), red gram (pigeon peas), green gram, beans, field peas and cluster beans (tables 2-10) in different application rates.
  • the weeds that have been controlled include Dinebra, Echinochloa colona, Eleusine indica, Cynadon dactylone, Cynotis sp, Commelina bengalensis, Alternanthera, and Parthenium.
  • DAA days after treatment
  • DAA days after treatment
  • the sowing was done during second week of August with a variety K20.
  • Phenological Status Vegetative growth 20 DAS, Design & Plot size: RBD & 20 Sq.mt.
  • the weeds that have been controlled include Echinochloa colona, Trianthema portulcastrum, Cleome viscosa, Digera arvensis, and Parthenium 10 hysterophorus.
  • EXAMPLE 4 Tank mix of Propaquizafop + Imazethapyr on Pigeon peas (Red Gram)
  • DAA days after treatment
  • DAA days after treatment
  • the weeds that have been controlled include Echinochloa colona, Panicum sp, Amaranthus sp and Phyllanthus sp.
  • EXAMPLE 6 Tank mix of Propaquizafop + Imazethapyr on Ground nut (Peanut)
  • DAA days after treatment
  • Plot size RBD & 20 Sq.mt.
  • the weeds that have been controlled include Echinochloa colona, Brachiaria sp., Digera sp., and Trianthima sp.
  • DAA days after treatment
  • EXAMPLE 8 Tank mix of Propaquizafop + Imazethapyr on Field Peas
  • DAA days after treatment
  • the sowing was done during third week of October with a variety of field peas.
  • Phenological Status Vegetative growth 28 DAS, Design & Plot size: RBD & 20 Sq.mt.
  • the weeds that have been controlled include Eleusine indica, Dactyloctenium aegyptium, Corchprus sp., and Trianthema monogyna.
  • DAA days after treatment

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Mélange herbicide synergique destiné à lutter contre la végétation indésirable, contenant de l'imazethapyr et du propaquizafop, des esters, des sels et/ou des combinaison de ceux-ci.
PCT/IB2014/061291 2013-05-08 2014-05-08 Mélange herbicide d'imazethapyr et de propaquizafop Ceased WO2014181281A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BR112015028146A BR112015028146A2 (pt) 2013-05-08 2014-05-08 mistura herbicida, composição herbicida, método para controlar a vegetação indesejável, mistura herbicida sinergística e kit
UAA201512066A UA119849C2 (uk) 2013-05-08 2014-05-08 Гербіцидна суміш імазетапіру та пропаквізафопу
RU2015151447A RU2656400C2 (ru) 2013-05-08 2014-05-08 Гербицидная смесь имазетапира и пропаквизафопа

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN524KO2013 2013-05-08
IN524/KOL/2013 2013-05-08

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WO2014181281A1 true WO2014181281A1 (fr) 2014-11-13

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PCT/IB2014/061291 Ceased WO2014181281A1 (fr) 2013-05-08 2014-05-08 Mélange herbicide d'imazethapyr et de propaquizafop

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AR (1) AR096214A1 (fr)
BR (1) BR112015028146A2 (fr)
RU (1) RU2656400C2 (fr)
UA (1) UA119849C2 (fr)
WO (1) WO2014181281A1 (fr)

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CN111357629A (zh) * 2020-04-07 2020-07-03 浙江万里学院 一种海马齿浮床培育装置及培育方法

Citations (5)

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US4545807A (en) 1980-11-26 1985-10-08 Hoffmann-La Roche Inc. Oxime ester herbicides
US4798619A (en) 1980-06-02 1989-01-17 American Cyanamid Co. 2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicidal agents
EP0482491A2 (fr) * 1990-10-20 1992-04-29 Hoechst Aktiengesellschaft Agents herbicides synergiques
US5700758A (en) * 1989-11-30 1997-12-23 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
WO1998024321A1 (fr) * 1996-12-06 1998-06-11 Novartis Ag Composition herbicide et procede de desherbage

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CA2244141A1 (fr) * 1996-03-15 1997-09-25 Novartis Ag Composition herbicide et procede de lutte contre les mauvaises herbes

Patent Citations (5)

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US4798619A (en) 1980-06-02 1989-01-17 American Cyanamid Co. 2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicidal agents
US4545807A (en) 1980-11-26 1985-10-08 Hoffmann-La Roche Inc. Oxime ester herbicides
US5700758A (en) * 1989-11-30 1997-12-23 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
EP0482491A2 (fr) * 1990-10-20 1992-04-29 Hoechst Aktiengesellschaft Agents herbicides synergiques
WO1998024321A1 (fr) * 1996-12-06 1998-06-11 Novartis Ag Composition herbicide et procede de desherbage

Non-Patent Citations (4)

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Title
COLBY S. R.: "Calculation of the synergistic and antagonistic responses of herbicide combinations", JOURNAL WEEDS, vol. 15, 1967, pages 20 - 22
INT. J. AGRI. BIOL., vol. 6, no. 1, 2004, pages 209 - 212
MYERS P F ET AL: "ANTAGONISM OF GRAMINICIDE ACTIVITY ON ANNUAL GRASS SPECIES BY IMAZETHAPYR1", WEED TECHNOLOGY, CHAMPAIGN, IL, US, vol. 6, no. 2, 1 January 1992 (1992-01-01), pages 333 - 338, XP002049998, ISSN: 0890-037X *
PAUL F. MYERS; HAROLD D. COBLE, WEED TECHNOLOGY, vol. 6, no. 2, 1992, pages 333 - 338

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RU2015151447A (ru) 2017-06-15
AR096214A1 (es) 2015-12-16
BR112015028146A2 (pt) 2017-07-25
RU2656400C2 (ru) 2018-06-05
UA119849C2 (uk) 2019-08-27

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