WO2021151143A1 - Herbicidal emulsion concentrate - Google Patents

Herbicidal emulsion concentrate Download PDF

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Publication number
WO2021151143A1
WO2021151143A1 PCT/AU2021/050042 AU2021050042W WO2021151143A1 WO 2021151143 A1 WO2021151143 A1 WO 2021151143A1 AU 2021050042 W AU2021050042 W AU 2021050042W WO 2021151143 A1 WO2021151143 A1 WO 2021151143A1
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WO
WIPO (PCT)
Prior art keywords
water
herbicide
emulsion concentrate
previous
herbicidal
Prior art date
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PCT/AU2021/050042
Other languages
French (fr)
Inventor
Rodrigo ADAMY
Yves COSTA
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Nufarm Australia Limited
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Filing date
Publication date
Priority claimed from AU2020900213A external-priority patent/AU2020900213A0/en
Application filed by Nufarm Australia Limited filed Critical Nufarm Australia Limited
Priority to BR112022014742A priority Critical patent/BR112022014742A8/en
Publication of WO2021151143A1 publication Critical patent/WO2021151143A1/en
Priority to CONC2022/0010626A priority patent/CO2022010626A2/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N25/02—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 containing liquids as carriers, diluents or solvents
    • 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
    • A01N25/02—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 containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N43/72—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 invention relates to a herbicidal emulsion concentrate containing two or more herbicides, to a method for preparing the concentrate composition and its use in control of weeds.
  • Herbicidal compositions containing multiple herbicides are useful in weed control as they allow combination of actives having complementary modes of action. Combinations offer the benefit of broadening the spectrum of weed control and managing herbicidal resistance which may develop in certain weeds through prolonged herbicide use.
  • Tank-mixing has previously been used as a way of combining different active agents in the spay-tank shortly before application.
  • tank mixing requires handling of a number of chemicals and has the risk of leading to over-dosing or under-dosing through error or inappropriate use.
  • Combinations in concentrate form provide predetermined control of proportions and avoid the need for multiple applications of herbicidal compositions.
  • a herbicidal emulsion concentrate composition comprising; a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, preferably the continuous water-immiscible (oil) phase is, or comprises the water-insoluble herbicide which is a liquid at ambient temperature; a discontinuous aqueous phase comprising a dispersed solid particulate herbicide; and optionally a water-soluble herbicide dissolved in the discontinuous aqueous phase.
  • the emulsion is thus of the water-in-oil type comprising an external oil phase and a dispersed, internal aqueous phase.
  • the dispersed solid particulate herbicide which is typically a further water- insoluble herbicide may, and typically will, be insoluble in the continuous water- immiscible phase.
  • the preferred herbicidal emulsion concentrate may contain at least one water-soluble herbicide in solution in the discontinuous aqueous phase.
  • the herbicidal emulsion concentrate will generally comprise a water-in-oil emulsifier.
  • emulsifiers are known surfactants.
  • the water-in- oil emulsifier has an HLB in the range of from 3 to 9, preferably 3 to 7.
  • the continuous oil phase may in one set of embodiments further comprise a surfactant which has a higher HLB of 12 to 18 to assist in stabilising the composition on dilution with water.
  • the solid particulate water-insoluble herbicide which is dispersed in the discontinuous aqueous phase is preferably flumioxazin;
  • the continuous water-immiscible phase comprises a herbicide selected from chloroacetamide and chloroacetanilide herbicides, such as metolachlor (typically as S-metalachlor);
  • the dispersed aqueous phase comprises a dissolved water-soluble herbicide selected from the group consisting of: organophosphorus herbicides including glyphosate salts, glufosinate salts such as glufosinate ammonium (which may be glufosinate-P, such as glufosinate-P; salts of imidazolinone herbicides such as imazethapyr, particularly imazethapyr-ammonium; auxin herbicide salts including salts of one or more aryloxy herbicides such as 2,4-D, MCPA, clopyralid, dichlor
  • the invention provides a method of preparing the emulsion concentrate composition comprising a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, the method comprising; combining a fine suspension of solid water-insoluble herbicide, preferably comprising a polymeric dispersant, with a water-soluble herbicide, preferably as an aqueous solution of the water-soluble herbicide, to form an aqueous composition; and dispersing the aqueous composition in a water-immiscible phase comprising a water- insoluble herbicide (preferably water-insoluble liquid herbicide) in the presence of a water-in-oil type emulsifier to form the emulsion.
  • a water-immiscible herbicide preferably water-insoluble liquid herbicide
  • the total herbicide concentration is typically in the range of from 10g/L to 900 g/L of emulsion composition.
  • the composition comprises 0.5 g/L to 300 g/L of dispersed solid particulate herbicide; 0.5 g/L to 700 g/L of water-insoluble herbicide in the continuous phase and 0.5 g/L to 500 g/L of water-soluble herbicide dissolved in the dispersed aqueous phase.
  • a liquid water-insoluble herbicide such as metolachlor in the continuous external water-immiscible phase of the emulsion.
  • (meth)acrylate refers to acrylate and/or methacrylate.
  • HLB hydrophile- lipophile balance. HLB values are published by emulsifier manufacturers and listed in references such as McCutcheon’s Emulsifiers and Detergents MC Publishing Co.; 2018 edition (April 5, 2018). HLB may be determined by calculating values for the different regions of the molecule, as described by Griffin in 1949 and 1954 “Calculation of HLB Values of Non- Ionic Surfactants", Journal of the Society of Cosmetic Chemists, 5 (4): 249-56 and by ICI Americas Inc “The HLB System a timesaving guide to emulsifier selection, March 1980.
  • polymer and polymeric includes homopolymers, copolymers and oligomers.
  • ambient temperature refers to 20°C and ambient pressure refers to atmospheric pressure (1 atm).
  • water-soluble herbicide as used herein includes any herbicide which is water-soluble at the concentration used in the concentrate.
  • the water-soluble herbicide such as the water-soluble salt of a herbicidal acid, will have a solubility in pure water of at least 50g/L, such as 100 g/L, at least 150 g/L, at least 200 g/L, at least 300 g/L, at least 500g/L or at least 600 g/L at a temperature of 25°C.
  • water-insoluble herbicide includes a component which is partially soluble in the aqueous concentrate such that at least a proportion thereof is present as an undissolved component.
  • Typical water-insoluble herbicides which may form the dispersed solid particulate herbicide component include flumioxazin, flumiclorac-pentyl, alachlor, indaziflam, tebuthiuron, sulfentrazone, diuron, linuron, sulfometuron, chlorsulphuron, metsulfuron, chlorimuron, atrazine, simazine, quizalofop, butroxydim, nicosulfuron, primsulfuron, bensulfuron, ametryn, pendimethalin, isoproturon, chlortoluron, diflufenican, mesotrione, aclonifen, flurochloridone, oxyfluorfen, isoxaflutole
  • water-insoluble and water immiscible preferably refer to components such as solbents, herbicideshaving a water solubility of no moe than 10 g / 100 ml, more preferably no moe than 5g/100 ml such as no more than 10 g/L or 5 g/L at ambient terperature and pressure
  • the dispersed solid particulate herbicide may be present in the aqueous phase component of the composition in an amount of 5 g/L to 500g/L of the aqueous phase and preferably from 10 g/L to 400 g/L such as 50 g/L to 350 g/L or 50 g/L to 200 g/L. as a proportion of the emulsion composition the dispersed particulate herbicide is typicall from 0.5 g/L to 300 g/L, preferably from 10 g/L to 250 g/L such as 10 g/L to 200 g/L or 10 g/L to 10Og/L of emulsion concentrate.
  • the dispersed aqueous phase may comprise a dissolved water-soluble herbicide, particularly such a herbicide selected from the group consisting of: organophosphorus herbicides such as glyphosate salts (e.g. isopropyl ammonium and potassium salts), glufosinate salts such as glufosinate ammonium (which may be glufosinate-P, such as glufosinate-P; salts of imidazolinone herbicides such as imazethapyr, particularly imazethapyr-ammonium; and auxin herbicide salts including salts of one or more aryloxy herbicides such as 2,4-D, MCPA, clopyralid, dichlorprop, triclopyr and mecoprop; salts of one or more aromatic acid herbicides such as dicamba, aminopyralid, clopyralid and picloram.
  • organophosphorus herbicides such as glyphosate salts (e.g. isopropy
  • the amount of water-soluble herbicide in the aqueous phase of the emulsion may be 5g/L to 600 g/L based on the aqueous phase components, preferably 10 g/L to 500 g/L, such as 50 g/L to 500 g/L or 100 g/L to 400 g/L of the aqueous phase component of the emulsion.
  • the water- soluble herbicide may be 0.5 g/L to 500 g/L, preferably 10 g/L to 400 g/L such as 30 g/L to 300 g/L or 50 g/L to 200 g/L of the emulsion composition.
  • the continuous water-immiscible (oil) phase comprises a water-insoluble herbicide which is preferably a liquid at ambient temperature.
  • the water-immiscible phase may comprise a water-immiscible solvent in which the water-insoluble herbicide may be dissolved in the case of a solid or miscible where it is a liquid.
  • the water-immiscible solvent where present, may be selected from hydrocarbons such mineral oils aliphatic, cycloaliphatic and aromatic hydrocarbons.
  • the continuous water-immiscible phase comprises a significant proportion of the liquid water-insoluble herbicide (preferably a liquid at ambient temperature) such as at least 50 wt%, at least 70 wt%, at least 80 wt% or at least 90 wt% of the water-immiscible phase.
  • the liquid water-insoluble herbicide preferably a liquid at ambient temperature
  • the weight ratio of aqueous phase components to water-immiscible phase components may vary widely depending on the concentration of solid particulate material in the aqueous phase, whether an active is present in the aqueous phase and any further adjuvants such as dispersants, wetting agents or the like.
  • the weight ratio of aqueous phase is in the range of 1 :10 to 10:1 , preferably 1 :5 to 5:1 more preferably 1 :1 to 1 :4.
  • the composition of the invention may contain a water-immiscible solvent.
  • Suitable solvents may be selected from the group consisting of mineral oil fractions such as, for example, kerosene, solvent naphtha, petroleum, coal tar oils and aromatic petroleum fractions; aliphatic, cycloaliphatic and aromatic hydrocarbons such as, for example, paraffin, cyclohexane, tetrahydronaphthalene and alkylated aromatics such as alkylated benzenes and naphthalenes.
  • An example of a particularly preferred hydrocarbon liquid carrier is a long chain alkylbenzene composition such as the Cs - Cio di- and trialkylbenzenes available from Exxon Mobil as SOLVESSO 150TM.
  • Another group of solvents include fatty alkyl amide solvents such as selected from the group consisting of ⁇ , ⁇ -dimethyl octanamide, N,N-dimethyl decanamide, N,N-dodencenamide, ⁇ , ⁇ -dimethyl caprylamide, N,N-dimethyl 2- ethylhexanoamide, ⁇ , ⁇ -dimethyl oleamide, N,N-dimethylLauricamide, N,N- dimethylmyristicamide, ⁇ , ⁇ -dimethyl 9-decenamide, and mixtures of two or more thereof.
  • the solvent is present in an amount of no more than 70wt% and preferably no more than 50 wt% of the water-immiscible phase such as no more than 30 wt%, no more than 20 wt% or no more than 10 wt% of the water-immiscible phase.
  • the amount of water- immiscible solvent is no more than 20 wt% and more preferably no more than 10 wt% of the water-immiscible phase.
  • the continuous water-immiscible phase has a melting point below about 0°C at 1 atm.
  • the continuous water-immiscible (oil) phase consist essentially or substantially of a water-immiscible liquid herbicide selected from chloroacetamide and chloracetanilide herbicides.
  • chloracetanilide herbicides that are liquid at ambient temperatures and can be formulated in compositions as the continuous water- immiscible phase without the need for an organic solvent, include acetochlor, butachlor, metolachlor (including S- metolachlor) and pretilachlor.
  • any suitable organic solvent known in the agricultural chemical formulating art in which the chloroacetamide herbicide is adequately soluble can be used.
  • the organic solvent is one in which the chloroacetamide herbicide is highly soluble, so that as high as possible a concentration of the chloroacetanilide herbicide can be accommodated in the oil phase and in the composition.
  • the more preferred liquid herbicides for use as the continuous water-immiscible (oil) phase are chloracetamide and metolachlor (particularly S-metolachlor).
  • the water-insoluble herbicide present in the continuous water-immiscible phase may comprise 10 g/L to 900 g/L of the water-immiscible phase, preferably 50 g/L to 900 g/L and more preferably 100 g/L to 900 g/L, still more preferably 300 g/L to 900 g/L such as 400 g/L to 900 g/L 500 g/L to 900 g/L, 600 g/L to 900 g/L or 650 g/L to 800 g/L of the continuous water-immiscible phase.
  • the water-insoluble herbicide present in the water-immiscible phase may be 5 g/L to 850 g/L of the emulsion concentrate, preferably 10 g/L to 850 g/L, more preferably 50 g/L to 850 g/L such as 100 g/L to 850 g/L, 200 g/L to 850 g/L, 300 g/L to 850 g/L or 400 g/L to 800 g/L of the emulsion concentrate.
  • the emulsion may comprise a water-in-oil emulsifier such as a surfactant of HLB of 3 to 9, preferably 3 to 7, more preferably 4 to 7 such as 4 to 6.
  • the water-in-oil emulsifier is selected from glycol, glycerol, and sorbitol esters of oleic, stearic, palmitic, and lauric acids, polyethoxylated fatty alcohols having 2 to 9 ethylene oxide units, sorbitan, monooleate, sorbitan monostearate, and sorbitan monopalmitate and polyethoxylated nonyl phenols having 2 to 9 ethylene oxide units.
  • Sorbitan monooleate is available under the trade name Span 80.
  • a further example of a water-in-oil emulsifier is an ethoxylated polyhydroxystearic acid having an HLB of about 5-6.
  • One example of such an emulsifier is ATLOXTM 4912.
  • a further example of a useful water-in-oil emulsifiers are alkyd-polyethylene glycol resins such as polyisobutylene succinic anhydride condensates with polyethylene glycol. Such an emulsifier is available from Croda,
  • water-in-oil type emulsifier is a star emulsifier comprising and ethoxylated sorbitol base having esterified with fatty acid chains such as 2 - 6 fatty acid chains.
  • a star emulsifier comprising and ethoxylated sorbitol base having esterified with fatty acid chains such as 2 - 6 fatty acid chains.
  • Such an emulsifier is commercially available from Croda, Inc. as ATLOXTM 4916.
  • the formation of the water-in-oil emulsion may be assisted by the presence of a hydrophilic (high HLB surfactant such as HLB 12 - 20) such as an EO-PO block copolymer.
  • a hydrophilic surfactant is ATLASTM G-5000.
  • a further example of a useful nonionic surfactant which may be used in combination with the water-in-oil emulsifier include polyoxyethylene polystyryl phenyl ethers such as mono-, di- or tri-styryl- phenol ethoxylate having 5 to 60 oxyethylene groups (e.g Soprophor 796P having an HLB of about 13.5, commercially available from Rhodia).
  • polyoxyethylene polystyryl phenyl ethers such as mono-, di- or tri-styryl- phenol ethoxylate having 5 to 60 oxyethylene groups (e.g Soprophor 796P having an HLB of about 13.5, commercially available from Rhodia).
  • water-in-oil emulsifiers include poly glycerol fatty acid esters such as Polyglycerol Oleate, Polyglycerol Stearate and Polyglycerol Palmitate.
  • poly glycerol fatty acid esters such as Polyglycerol Oleate, Polyglycerol Stearate and Polyglycerol Palmitate.
  • Specific examples of such emulsifiers include triglycerol diisostearate (HLB 4.7), triglycerol triisostearate (HLB 2.6), hexaglycerol triisostearate (HLB 5.3), hexaglycerol hexaisostearate, (HLB 2.4) and octaglycerol pentaisostearate (HLB3.8).
  • the herbicidal emulsion concentrate comprises a water-in-oil emulsifier of HLB of 3 to 9, preferably 3 to 7, more preferably 4 to 7 such as 4 to 6 in an amount in the range of from 1 g/L to 100 g/L, preferably 5 g/L to 80 g/L such as 10 g/L to 60 g/L of the emulsion.
  • the emulsion comprises a dispersed aqueous phase comprising a suspension of water-insoluble herbicide such as flumioxazin.
  • the water-insoluble herbicide solid particles are typically of size in the range of 1 micron to 10 microns such as 1 microns to 8 microns.
  • the mean particle size D50 is between 1 and 10 microns, between 2 and 9 microns, between 3 and 8 microns, between 1 and 5 microns.
  • the emulsion composition may comprise a chelating agent, such as EDTA, and citric acid, typically as part of the dispersed aqueous phase.
  • a chelating agent such as EDTA
  • citric acid typically as part of the dispersed aqueous phase.
  • the emulsion typically comprises a dispersant to stabilise the solid particulate herbicide in the dispersed aqueous phase.
  • dispersants include naphthalene sulfonate-formaldehyde condensates that may optionally be alkyl substituted and salts thereof; polycarboxylates; comb-type graft copolymers such as polymers have a backbone chain of a polymer such as (meth) acrylic polymer or copolymer to which are appended polyoxyalkylated lateral groups such as polyoxyethylene groups; and ethoxylated tristyrylphenol sulfates.
  • Lignosulfonates such as sodium lignosulfonates.
  • the surfactant component of the aqueous phase including dispersants and wetters are present in an amount of from 5 g/L to 100 g/L, preferably 8 g/L to 80 g/L such as 8 g/L to 50 g/L or 8 g/L to 30 g/L of the aqueous phase.
  • the dispersed solid particulate herbicide which is typically water insoluble may be present in the aqueous phase in a range of concentrations depending on the efficacy and desired weed control.
  • the solid particulate herbicide will be present in an amount of from 0.5 g/L to 500 g/L of the aqueous phase such as 10g/L to 400 g/L or 50 g/L to 360 g/L.
  • the aqueous phase may optionally include a water-soluble herbicide in solution.
  • the amount of dissolved herbicide in the aqueous phase may, for example be 0.5 g/L to 800 g/L, preferably 10 g/L to 750 g/L and more preferably 50 g/L to 750 g/L such as 100 g/L to 700 g/L.
  • the herbicidal emulsion concentrate composition comprises: a continuous water-immiscible (oil) phase comprising S-metolachlor from in an amount of 650 g/L to 850 g/L of emulsion; a discontinuous aqueous phase comprising flumioxazin dispersed in solid particulate form in an amount of 10 g/L to 100g/L of the emulsion concentrate;
  • the invention provides a method of preparing the emulsion concentrate composition comprising continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, the method comprising; combining a fine suspension of solid particulate water-insoluble herbicide, preferably comprising a polymeric dispersant, with a water-soluble herbicide, preferably as an aqueous solution of the water-soluble herbicide to form an aqueous composition; and dispersing the aqueous composition in a water-immiscible phase comprising a water-insoluble herbicide (preferably being liquid at ambient temperature) in the presence of a water-in-oil type emulsifier to form the emulsion.
  • aqueous composition will comprise a dispersant and optionally a wetting agent to provide a stable dispersion of the particulate solid herbicide.
  • the water-insoluble herbicide may be provided in the form of a solution comprising an oil-in-water emulsifier, optionally with a hydrophobic organic solvent and optionally a surfactant.
  • the aqueous and water-immiscible phases are combined, generally with rapid mixing, which may be high shear mixing.
  • the aqueous phase may be added to the water-immiscible phase or the water-immiscible phase may be added to the aqueous phase though we have generally followed the practice of adding the water- immiscible phase to the aqueous phase.
  • the emulsion composition may comprise one or more wetting agents, one or more antifoam agents, one or more antifreeze agents, one or more thickening agents, and/or one or more water-soluble solvents.
  • the aqueous suspension concentrate phase preferably comprises a thickening agent such as selected from the group consisting of xanthan gum, water- soluble polyacrylic acid, polyvinyl pyrrolidone and silicates is included in the formulation in an amount sufficient to provide the desired viscosity.
  • a thickening agent such as selected from the group consisting of xanthan gum, water- soluble polyacrylic acid, polyvinyl pyrrolidone and silicates is included in the formulation in an amount sufficient to provide the desired viscosity.
  • the thickener is from 0.5% to 4% by weight of the aqueous phase such as 0.5 % to 2% by weight of the aqueous phase.
  • An antifreeze agent such as propylene glycol
  • propylene glycol may be incorporated in the composition.
  • the incorporation of an antifoam agent is often useful to prevent foaming at high sheer rates.
  • antifoam include siloxane antifoams such as SILFOAMTM SRE
  • the invention further provides a method for control of weeds in an area.
  • the herbicidal emulsion composition may be applied to the site in which weed control is required by dilution with water and application to the site, for example, by spray application.
  • the emulsion concentrate may be applied at a range of rates per acre of land depending on the weeds to be controlled and the growth stage of the weeds.
  • the emulsion concentrate composition is applied at a rate of concentrate of at least about 100 ml/hectare and typically diluted to a spray volume of at 20 liters to 1000 liters per hectare.
  • the emulsion concentrate can be used for the control of a wide range of broad-leaved weeds, including marestale, Palmer amaranth, waterhemp, charlock, chickweed, cleavers, common poppy, field pansy, fumitory, groundsel, speedwells, mayweed, red deadnettle, coffee senna, common ragweed, dandelion, eclipta, evening primrose, false chamomile, Florida beggarweed, Florida pusley, golden crown beard, hairy indigo, hemp sesbania, henbit, jimsonweed, kochia, lambsquarters, mustard, nightshades, pigweeds, prickly sida, puncturevine, purslane, radish, redmaids, redweed, smallflower morningglory, spurred anoda, tropic croton, Venice mallow, waterhemp, wild poinsettia, and Shepherd’s purse, as well as control of annual
  • Example 1 preparation of aqueous phase suspension concentrate
  • Thickener was prepared by adding PROXEL GXLTM and then KELZANTMAP to water in the following proportions shown in Table 1
  • An aqueous solution of imazethapyr was prepared by adding 98% technical imazethapyr to water followed by ammonium hydroxide 28% which was stirred following addition to stabilise the pH. Acetic acid was added and stirred to provide a pH of 7.8 to 8.2. Table 2 shows the proportions of materials used.
  • PolyfonTM H dispersant was added to the main portion of water and mixed followed by SlifoamTM SRE antifoam and ProxelTM GXL biocide, SokalanTM HP53 thickener, SoprophorTM 4D384 anionic surfactant and PluronicTM PE10500 nonionic surfactant (previously melted at 80°C)/Genapol TMPF40 surfactant were added and the composition mixed to provide complete homogenization. Flumioxazin Tech was then added and mixed until completely wetted; CabosilTM M-5 thickener was added followed by the balance of water to make up the amount recorded, and the composition was mixed.
  • a water-immiscible organic phase is prepared by combining the components shown in Table 4 in the order specified.
  • a water-in-oil emulsion containing the aqueous phase suspension concentrate of Example 1 is prepared by addition of the organic base set out in Table 4 to the aqueous phase with constant vigorous mixing to form oil-in-water emulsions having the proportions shown in Table 5.
  • Example 3 to 5 The water-in-oil emulsion compositions (Comp.) of Example 3 to 5 are prepared by slowly adding the water-immiscible phase to the aqueous phase of Example 1 to the organic Phase in accordance with the tables below:

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  • Dispersion Chemistry (AREA)
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Abstract

A herbicidal emulsion concentrate composition comprising; a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, preferably the continuous water-immiscible (oil) phase is, or comprises a water-insoluble herbicide which is a liquid at ambient temperature; a discontinuous aqueous phase comprising a dispersed solid particulate herbicide; and optionally a water-soluble herbicide dissolved in the discontinuous aqueous phase.

Description

Herbicidal Emulsion Concentrate
Field
[0001] The invention relates to a herbicidal emulsion concentrate containing two or more herbicides, to a method for preparing the concentrate composition and its use in control of weeds.
Background
[0002] Herbicidal compositions containing multiple herbicides are useful in weed control as they allow combination of actives having complementary modes of action. Combinations offer the benefit of broadening the spectrum of weed control and managing herbicidal resistance which may develop in certain weeds through prolonged herbicide use.
[0003] It is frequently desirable to combine herbicides of different physicochemical properties which create significant difficulties for the formulator. These problems are an issue with many of the known formulation types such as solution concentrates, emulsions, suspensions, foams, powders and water dispersible granules.
[0004] Tank-mixing has previously been used as a way of combining different active agents in the spay-tank shortly before application. However, tank mixing requires handling of a number of chemicals and has the risk of leading to over-dosing or under-dosing through error or inappropriate use. Combinations in concentrate form provide predetermined control of proportions and avoid the need for multiple applications of herbicidal compositions.
[0005] Further complications arise where herbicides are poorly stable or chemically incompatible.
[0006] There is a need for new herbicidal concentrate compositions which improve the ability to combine herbicides of differing physicochemical properties. Summary of Invention
[0007] Accordingly, there is provided a herbicidal emulsion concentrate composition comprising; a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, preferably the continuous water-immiscible (oil) phase is, or comprises the water-insoluble herbicide which is a liquid at ambient temperature; a discontinuous aqueous phase comprising a dispersed solid particulate herbicide; and optionally a water-soluble herbicide dissolved in the discontinuous aqueous phase.
[0008] The emulsion is thus of the water-in-oil type comprising an external oil phase and a dispersed, internal aqueous phase.
[0009] The dispersed solid particulate herbicide, which is typically a further water- insoluble herbicide may, and typically will, be insoluble in the continuous water- immiscible phase.
[0010] The preferred herbicidal emulsion concentrate may contain at least one water-soluble herbicide in solution in the discontinuous aqueous phase.
[0011] The herbicidal emulsion concentrate will generally comprise a water-in-oil emulsifier. Such emulsifiers are known surfactants. In one embodiment the water-in- oil emulsifier has an HLB in the range of from 3 to 9, preferably 3 to 7.
[0012] The continuous oil phase may in one set of embodiments further comprise a surfactant which has a higher HLB of 12 to 18 to assist in stabilising the composition on dilution with water.
[0013] In a specific embodiment the solid particulate water-insoluble herbicide which is dispersed in the discontinuous aqueous phase is preferably flumioxazin; the continuous water-immiscible phase comprises a herbicide selected from chloroacetamide and chloroacetanilide herbicides, such as metolachlor (typically as S-metalachlor); the dispersed aqueous phase comprises a dissolved water-soluble herbicide selected from the group consisting of: organophosphorus herbicides including glyphosate salts, glufosinate salts such as glufosinate ammonium (which may be glufosinate-P, such as glufosinate-P; salts of imidazolinone herbicides such as imazethapyr, particularly imazethapyr-ammonium; auxin herbicide salts including salts of one or more aryloxy herbicides such as 2,4-D, MCPA, clopyralid, dichlorprop, triclopyr and mecoprop; salts of one or more aromatic acid herbicides such as dicamba, aminopyralid, clopyralid and picloram.
[0014] In a further aspect the invention provides a method of preparing the emulsion concentrate composition comprising a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, the method comprising; combining a fine suspension of solid water-insoluble herbicide, preferably comprising a polymeric dispersant, with a water-soluble herbicide, preferably as an aqueous solution of the water-soluble herbicide, to form an aqueous composition; and dispersing the aqueous composition in a water-immiscible phase comprising a water- insoluble herbicide (preferably water-insoluble liquid herbicide) in the presence of a water-in-oil type emulsifier to form the emulsion.
[0015] The total herbicide concentration is typically in the range of from 10g/L to 900 g/L of emulsion composition.
[0016] In one set of embodiments the composition comprises 0.5 g/L to 300 g/L of dispersed solid particulate herbicide; 0.5 g/L to 700 g/L of water-insoluble herbicide in the continuous phase and 0.5 g/L to 500 g/L of water-soluble herbicide dissolved in the dispersed aqueous phase. One of the significant advantages of the invention is that it allows the use of a high proportion of a liquid water-insoluble herbicide such as metolachlor in the continuous external water-immiscible phase of the emulsion. [0017] Detailed Description
[0018] Where the terms "comprise", "comprises", "comprised" or "comprising" are used in this specification (including the claims) they are to be interpreted as specifying the presence of the stated features, integers, steps or components, but not precluding the presence of one or more other features, integers, steps or components, or group thereof.
[0019] The term "(meth)acrylate" refers to acrylate and/or methacrylate.
[0020] As used herein and in the appended claims, "HLB" refers to hydrophile- lipophile balance. HLB values are published by emulsifier manufacturers and listed in references such as McCutcheon’s Emulsifiers and Detergents MC Publishing Co.; 2018 edition (April 5, 2018). HLB may be determined by calculating values for the different regions of the molecule, as described by Griffin in 1949 and 1954 "Calculation of HLB Values of Non- Ionic Surfactants", Journal of the Society of Cosmetic Chemists, 5 (4): 249-56 and by ICI Americas Inc “The HLB System a timesaving guide to emulsifier selection, March 1980.
[0021] The terms polymer and polymeric includes homopolymers, copolymers and oligomers.
[0022] In the specification “ambient temperature” refers to 20°C and ambient pressure refers to atmospheric pressure (1 atm).
[0023] The term "water-soluble herbicide" as used herein includes any herbicide which is water-soluble at the concentration used in the concentrate. Typically, the water-soluble herbicide, such as the water-soluble salt of a herbicidal acid, will have a solubility in pure water of at least 50g/L, such as 100 g/L, at least 150 g/L, at least 200 g/L, at least 300 g/L, at least 500g/L or at least 600 g/L at a temperature of 25°C.
[0024] The term “water-insoluble herbicide” includes a component which is partially soluble in the aqueous concentrate such that at least a proportion thereof is present as an undissolved component. Typical water-insoluble herbicides which may form the dispersed solid particulate herbicide component include flumioxazin, flumiclorac-pentyl, alachlor, indaziflam, tebuthiuron, sulfentrazone, diuron, linuron, sulfometuron, chlorsulphuron, metsulfuron, chlorimuron, atrazine, simazine, quizalofop, butroxydim, nicosulfuron, primsulfuron, bensulfuron, ametryn, pendimethalin, isoproturon, chlortoluron, diflufenican, mesotrione, aclonifen, flurochloridone, oxyfluorfen, isoxaflutole, imazamox and thifensulfuron although the present invention does not depend critically on the nature of the water-insoluble herbicide and many others are published in the literature. The preferred water- insoluble solid particulate herbicide is flumioxazin.
[0025] The terms water-insoluble and water immiscible preferably refer to components such as solbents, herbicideshaving a water solubility of no moe than 10 g / 100 ml, more preferably no moe than 5g/100 ml such as no more than 10 g/L or 5 g/L at ambient terperature and pressure
[0026] The dispersed solid particulate herbicide may be present in the aqueous phase component of the composition in an amount of 5 g/L to 500g/L of the aqueous phase and preferably from 10 g/L to 400 g/L such as 50 g/L to 350 g/L or 50 g/L to 200 g/L. as a proportion of the emulsion composition the dispersed particulate herbicide is typicall from 0.5 g/L to 300 g/L, preferably from 10 g/L to 250 g/L such as 10 g/L to 200 g/L or 10 g/L to 10Og/L of emulsion concentrate.
[0027] The dispersed aqueous phase may comprise a dissolved water-soluble herbicide, particularly such a herbicide selected from the group consisting of: organophosphorus herbicides such as glyphosate salts (e.g. isopropyl ammonium and potassium salts), glufosinate salts such as glufosinate ammonium (which may be glufosinate-P, such as glufosinate-P; salts of imidazolinone herbicides such as imazethapyr, particularly imazethapyr-ammonium; and auxin herbicide salts including salts of one or more aryloxy herbicides such as 2,4-D, MCPA, clopyralid, dichlorprop, triclopyr and mecoprop; salts of one or more aromatic acid herbicides such as dicamba, aminopyralid, clopyralid and picloram.
[0028] The amount of water-soluble herbicide in the aqueous phase of the emulsion may be 5g/L to 600 g/L based on the aqueous phase components, preferably 10 g/L to 500 g/L, such as 50 g/L to 500 g/L or 100 g/L to 400 g/L of the aqueous phase component of the emulsion. As a proporion of emulsion the water- soluble herbicide may be 0.5 g/L to 500 g/L, preferably 10 g/L to 400 g/L such as 30 g/L to 300 g/L or 50 g/L to 200 g/L of the emulsion composition.
[0029] The continuous water-immiscible (oil) phase comprises a water-insoluble herbicide which is preferably a liquid at ambient temperature. The water-immiscible phase may comprise a water-immiscible solvent in which the water-insoluble herbicide may be dissolved in the case of a solid or miscible where it is a liquid. The water-immiscible solvent, where present, may be selected from hydrocarbons such mineral oils aliphatic, cycloaliphatic and aromatic hydrocarbons. In preferred examples the continuous water-immiscible phase comprises a significant proportion of the liquid water-insoluble herbicide (preferably a liquid at ambient temperature) such as at least 50 wt%, at least 70 wt%, at least 80 wt% or at least 90 wt% of the water-immiscible phase.
[0030] The weight ratio of aqueous phase components to water-immiscible phase components may vary widely depending on the concentration of solid particulate material in the aqueous phase, whether an active is present in the aqueous phase and any further adjuvants such as dispersants, wetting agents or the like. In one set of embodiments the weight ratio of aqueous phase is in the range of 1 :10 to 10:1 , preferably 1 :5 to 5:1 more preferably 1 :1 to 1 :4.
[0031] The composition of the invention may contain a water-immiscible solvent. Suitable solvents may be selected from the group consisting of mineral oil fractions such as, for example, kerosene, solvent naphtha, petroleum, coal tar oils and aromatic petroleum fractions; aliphatic, cycloaliphatic and aromatic hydrocarbons such as, for example, paraffin, cyclohexane, tetrahydronaphthalene and alkylated aromatics such as alkylated benzenes and naphthalenes. An example of a particularly preferred hydrocarbon liquid carrier is a long chain alkylbenzene composition such as the Cs - Cio di- and trialkylbenzenes available from Exxon Mobil as SOLVESSO 150™. Another group of solvents include fatty alkyl amide solvents such as selected from the group consisting of Ν,Ν-dimethyl octanamide, N,N-dimethyl decanamide, N,N-dodencenamide, Ν,Ν-dimethyl caprylamide, N,N-dimethyl 2- ethylhexanoamide, Ν,Ν-dimethyl oleamide, N,N-dimethylLauricamide, N,N- dimethylmyristicamide, Ν,Ν-dimethyl 9-decenamide, and mixtures of two or more thereof. [0032] Typically, the solvent is present in an amount of no more than 70wt% and preferably no more than 50 wt% of the water-immiscible phase such as no more than 30 wt%, no more than 20 wt% or no more than 10 wt% of the water-immiscible phase. Where the water-insoluble herbicide is a liquid it is preferred that the amount of water- immiscible solvent is no more than 20 wt% and more preferably no more than 10 wt% of the water-immiscible phase.
[0033] It is preferred that the continuous water-immiscible phase has a melting point below about 0°C at 1 atm. In one embodiment the continuous water-immiscible (oil) phase consist essentially or substantially of a water-immiscible liquid herbicide selected from chloroacetamide and chloracetanilide herbicides. Examples of chloracetanilide herbicides that are liquid at ambient temperatures and can be formulated in compositions as the continuous water- immiscible phase without the need for an organic solvent, include acetochlor, butachlor, metolachlor (including S- metolachlor) and pretilachlor. Where an organic solvent is desired or required, any suitable organic solvent known in the agricultural chemical formulating art in which the chloroacetamide herbicide is adequately soluble can be used. Preferably the organic solvent is one in which the chloroacetamide herbicide is highly soluble, so that as high as possible a concentration of the chloroacetanilide herbicide can be accommodated in the oil phase and in the composition. The more preferred liquid herbicides for use as the continuous water-immiscible (oil) phase are chloracetamide and metolachlor (particularly S-metolachlor).
[0034] The water-insoluble herbicide present in the continuous water-immiscible phase may comprise 10 g/L to 900 g/L of the water-immiscible phase, preferably 50 g/L to 900 g/L and more preferably 100 g/L to 900 g/L, still more preferably 300 g/L to 900 g/L such as 400 g/L to 900 g/L 500 g/L to 900 g/L, 600 g/L to 900 g/L or 650 g/L to 800 g/L of the continuous water-immiscible phase. The water-insoluble herbicide present in the water-immiscible phase may be 5 g/L to 850 g/L of the emulsion concentrate, preferably 10 g/L to 850 g/L, more preferably 50 g/L to 850 g/L such as 100 g/L to 850 g/L, 200 g/L to 850 g/L, 300 g/L to 850 g/L or 400 g/L to 800 g/L of the emulsion concentrate.
[0035] The emulsion may comprise a water-in-oil emulsifier such as a surfactant of HLB of 3 to 9, preferably 3 to 7, more preferably 4 to 7 such as 4 to 6. In one embodiment the water-in-oil emulsifier is selected from glycol, glycerol, and sorbitol esters of oleic, stearic, palmitic, and lauric acids, polyethoxylated fatty alcohols having 2 to 9 ethylene oxide units, sorbitan, monooleate, sorbitan monostearate, and sorbitan monopalmitate and polyethoxylated nonyl phenols having 2 to 9 ethylene oxide units. Sorbitan monooleate is available under the trade name Span 80.
[0036] A further example of a water-in-oil emulsifier is an ethoxylated polyhydroxystearic acid having an HLB of about 5-6. One example of such an emulsifier is ATLOX™ 4912. A further example of a useful water-in-oil emulsifiers are alkyd-polyethylene glycol resins such as polyisobutylene succinic anhydride condensates with polyethylene glycol. Such an emulsifier is available from Croda,
Inc. as ATLOX™ 4914. Yet another useful water-in-oil type emulsifier is a star emulsifier comprising and ethoxylated sorbitol base having esterified with fatty acid chains such as 2 - 6 fatty acid chains. Such an emulsifier is commercially available from Croda, Inc. as ATLOX™ 4916. In some embodiments the formation of the water-in-oil emulsion may be assisted by the presence of a hydrophilic (high HLB surfactant such as HLB 12 - 20) such as an EO-PO block copolymer. An example of such a hydrophilic surfactant is ATLAS™ G-5000. A further example of a useful nonionic surfactant which may be used in combination with the water-in-oil emulsifier include polyoxyethylene polystyryl phenyl ethers such as mono-, di- or tri-styryl- phenol ethoxylate having 5 to 60 oxyethylene groups (e.g Soprophor 796P having an HLB of about 13.5, commercially available from Rhodia).
[0037] Further examples of water-in-oil emulsifiers include poly glycerol fatty acid esters such as Polyglycerol Oleate, Polyglycerol Stearate and Polyglycerol Palmitate. Specific examples of such emulsifiers include triglycerol diisostearate (HLB 4.7), triglycerol triisostearate (HLB 2.6), hexaglycerol triisostearate (HLB 5.3), hexaglycerol hexaisostearate, (HLB 2.4) and octaglycerol pentaisostearate (HLB3.8).
[0038] In one set of embodiments the herbicidal emulsion concentrate comprises a water-in-oil emulsifier of HLB of 3 to 9, preferably 3 to 7, more preferably 4 to 7 such as 4 to 6 in an amount in the range of from 1 g/L to 100 g/L, preferably 5 g/L to 80 g/L such as 10 g/L to 60 g/L of the emulsion. [0039] The emulsion comprises a dispersed aqueous phase comprising a suspension of water-insoluble herbicide such as flumioxazin. The water-insoluble herbicide solid particles are typically of size in the range of 1 micron to 10 microns such as 1 microns to 8 microns. In some aspects of the invention, the mean particle size D50 is between 1 and 10 microns, between 2 and 9 microns, between 3 and 8 microns, between 1 and 5 microns.
[0040] The emulsion composition may comprise a chelating agent, such as EDTA, and citric acid, typically as part of the dispersed aqueous phase.
[0041] The emulsion typically comprises a dispersant to stabilise the solid particulate herbicide in the dispersed aqueous phase. Examples of dispersants include naphthalene sulfonate-formaldehyde condensates that may optionally be alkyl substituted and salts thereof; polycarboxylates; comb-type graft copolymers such as polymers have a backbone chain of a polymer such as (meth) acrylic polymer or copolymer to which are appended polyoxyalkylated lateral groups such as polyoxyethylene groups; and ethoxylated tristyrylphenol sulfates. Lignosulfonates such as sodium lignosulfonates. Typically, the surfactant component of the aqueous phase including dispersants and wetters are present in an amount of from 5 g/L to 100 g/L, preferably 8 g/L to 80 g/L such as 8 g/L to 50 g/L or 8 g/L to 30 g/L of the aqueous phase.
[0042] The dispersed solid particulate herbicide, which is typically water insoluble may be present in the aqueous phase in a range of concentrations depending on the efficacy and desired weed control. Typically, the solid particulate herbicide will be present in an amount of from 0.5 g/L to 500 g/L of the aqueous phase such as 10g/L to 400 g/L or 50 g/L to 360 g/L.
[0043] The aqueous phase may optionally include a water-soluble herbicide in solution. The amount of dissolved herbicide in the aqueous phase may, for example be 0.5 g/L to 800 g/L, preferably 10 g/L to 750 g/L and more preferably 50 g/L to 750 g/L such as 100 g/L to 700 g/L.
[0044] In one specific set of embodiments the herbicidal emulsion concentrate composition comprises: a continuous water-immiscible (oil) phase comprising S-metolachlor from in an amount of 650 g/L to 850 g/L of emulsion; a discontinuous aqueous phase comprising flumioxazin dispersed in solid particulate form in an amount of 10 g/L to 100g/L of the emulsion concentrate;
Imazethapyr dissolved in the discontinuous aqueous phase in an amount of 50 g/L to 200 g/L of the emulsion concentrate; a surfactant in the aqueous phase in an amount of from 8 g/L to 50 g/L of the aqueous phase; and an oil in water emulsifier of HLB 3 to 7 present in an amount of from 5 g/L to 80 g/L of emulsion concentrate.
[0045] In a further aspect the invention provides a method of preparing the emulsion concentrate composition comprising continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, the method comprising; combining a fine suspension of solid particulate water-insoluble herbicide, preferably comprising a polymeric dispersant, with a water-soluble herbicide, preferably as an aqueous solution of the water-soluble herbicide to form an aqueous composition; and dispersing the aqueous composition in a water-immiscible phase comprising a water-insoluble herbicide (preferably being liquid at ambient temperature) in the presence of a water-in-oil type emulsifier to form the emulsion.
[0046] Generally, with aqueous composition will comprise a dispersant and optionally a wetting agent to provide a stable dispersion of the particulate solid herbicide. The water-insoluble herbicide may be provided in the form of a solution comprising an oil-in-water emulsifier, optionally with a hydrophobic organic solvent and optionally a surfactant.
[0047] The aqueous and water-immiscible phases are combined, generally with rapid mixing, which may be high shear mixing. The aqueous phase may be added to the water-immiscible phase or the water-immiscible phase may be added to the aqueous phase though we have generally followed the practice of adding the water- immiscible phase to the aqueous phase.
[0048] The emulsion composition may comprise one or more wetting agents, one or more antifoam agents, one or more antifreeze agents, one or more thickening agents, and/or one or more water-soluble solvents.
[0049] The aqueous suspension concentrate phase preferably comprises a thickening agent such as selected from the group consisting of xanthan gum, water- soluble polyacrylic acid, polyvinyl pyrrolidone and silicates is included in the formulation in an amount sufficient to provide the desired viscosity. Typically, the thickener is from 0.5% to 4% by weight of the aqueous phase such as 0.5 % to 2% by weight of the aqueous phase.
[0050] An antifreeze agent, such as propylene glycol, may be incorporated in the composition. The incorporation of an antifoam agent is often useful to prevent foaming at high sheer rates. Examples of antifoam include siloxane antifoams such as SILFOAM™ SRE
[0051] The invention further provides a method for control of weeds in an area. The herbicidal emulsion composition may be applied to the site in which weed control is required by dilution with water and application to the site, for example, by spray application.
[0052] The emulsion concentrate may be applied at a range of rates per acre of land depending on the weeds to be controlled and the growth stage of the weeds. For example, in one embodiment the emulsion concentrate composition is applied at a rate of concentrate of at least about 100 ml/hectare and typically diluted to a spray volume of at 20 liters to 1000 liters per hectare.
[0053] The emulsion concentrate can be used for the control of a wide range of broad-leaved weeds, including marestale, Palmer amaranth, waterhemp, charlock, chickweed, cleavers, common poppy, field pansy, fumitory, groundsel, speedwells, mayweed, red deadnettle, coffee senna, common ragweed, dandelion, eclipta, evening primrose, false chamomile, Florida beggarweed, Florida pusley, golden crown beard, hairy indigo, hemp sesbania, henbit, jimsonweed, kochia, lambsquarters, mustard, nightshades, pigweeds, prickly sida, puncturevine, purslane, radish, redmaids, redweed, smallflower morningglory, spurred anoda, tropic croton, Venice mallow, waterhemp, wild poinsettia, and Shepherd’s purse, as well as control of annual meadow grass, black-grass, and rye -grass.
[0054] The invention will now be described with reference to the following examples. It is to be understood that the examples are provided by way of illustration of the invention and that they are in no way limiting to the scope of the invention.
[0055] EXAMPLES
[0056] Example 1 - preparation of aqueous phase suspension concentrate
[0057] Part A
[0058] Thickener was prepared by adding PROXEL GXL™ and then KELZAN™AP to water in the following proportions shown in Table 1
[0059] Table 1
Figure imgf000013_0001
[0060] Part B-lmazethapyr base
[0061] An aqueous solution of imazethapyr was prepared by adding 98% technical imazethapyr to water followed by ammonium hydroxide 28% which was stirred following addition to stabilise the pH. Acetic acid was added and stirred to provide a pH of 7.8 to 8.2. Table 2 shows the proportions of materials used.
[0062] Table 2
Figure imgf000014_0001
[0063] Part C - Flumioxazin suspension concentrate aqueous phase
[0064] Polyfon™ H dispersant was added to the main portion of water and mixed followed by Slifoam™ SRE antifoam and Proxel™ GXL biocide, Sokalan™ HP53 thickener, Soprophor™ 4D384 anionic surfactant and Pluronic™ PE10500 nonionic surfactant (previously melted at 80°C)/Genapol ™PF40 surfactant were added and the composition mixed to provide complete homogenization. Flumioxazin Tech was then added and mixed until completely wetted; Cabosil™ M-5 thickener was added followed by the balance of water to make up the amount recorded, and the composition was mixed. The Flumioxazin suspension concentrate aqueous phase was wet milled in the composition to achieve the Particle Size (D50) = 1 .0 to 2.0 microns Particle Size (D90) = 3.0 to 5.0 microns. The proportion of components is shown in Table 3
[0065] Table 3
Figure imgf000014_0002
Figure imgf000015_0001
# polyethylene glycol 2,4,6-tris(1 -phenylethyl)phenyl ether sulfate ammonium salt.
[0066] Example 2 - Preparation of emulsion
[0067] A water-immiscible organic phase is prepared by combining the components shown in Table 4 in the order specified.
[0068] Table 4
Figure imgf000015_0002
[0069] A water-in-oil emulsion containing the aqueous phase suspension concentrate of Example 1 is prepared by addition of the organic base set out in Table 4 to the aqueous phase with constant vigorous mixing to form oil-in-water emulsions having the proportions shown in Table 5.
[0070] Table 5
Figure imgf000015_0003
[0071] Examples 3 to 5 - Emulsion
[0072] The water-in-oil emulsion compositions (Comp.) of Example 3 to 5 are prepared by slowly adding the water-immiscible phase to the aqueous phase of Example 1 to the organic Phase in accordance with the tables below:
[0073] Example 3
[0074] Table 6
Figure imgf000016_0001
[0075] Example 4
[0076] Table 7
Figure imgf000016_0002
[0077] Example 5
[0078] Table 8
Figure imgf000017_0001

Claims

Claims
1. A herbicidal emulsion concentrate composition comprising; a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide; a discontinuous aqueous phase comprising a dispersed solid particulate herbicide; and optionally a water-soluble herbicide dissolved in the discontinuous aqueous phase.
2. The herbicidal emulsion concentrate of claim 1 , wherein the water-insoluble herbicide is a liquid at ambient temperature
3. The herbicidal emulsion concentrate comprising at least one water-soluble herbicide in solution in the discontinuous aqueous phase.
4. The herbicidal emulsion concentrate of any one of the previous claims comprising a water-in-oil type emulsifier, preferably an emulsifier of HLB in the range of from 3 to 9, preferably 3 to 7.
5. The herbicidal emulsion concentrate of any one of the previous claims comprising a water-in-oil type emulsifier in an amount of 1 g/L to 100 g/L, preferably 5 g/L 80 g/L of emulsion concentrate.
6. The herbicidal emulsion concentrate composition comprising; a continuous water-immiscible (oil) phase comprising a water-insoluble herbicide, preferably the continuous water-immiscible (oil) phase is, or comprises a water-insoluble herbicide which is a liquid at ambient temperature; a discontinuous aqueous phase comprising a dispersed solid particulate herbicide; and optionally a water-soluble herbicide dissolved in the discontinuous aqueous phase.
7. The herbicidal emulsion concentrate of any one of the previous claims wherein the dispersed solid particulate herbicide is at least one selected from the group consisting of flumiclorac-pentyl, alachlor, indaziflam, tebuthiuron, sulfentrazone, flumioxazin, diuron, linuron, sulfometuron, chlorsulphuron, metsulfuron, chlorimuron, atrazine, simazine, quizalofop, butroxydim, nicosulfuron, primsulfuron, bensulfuron, ametryn, pendimethalin, isoproturon, chlortoluron, diflufenican, mesotrione, aclonifen, flurochloridone, oxyfluorfen, isoxaflutole, imazamox and thifensulfuron.
8. The herbicidal emulsion concentrate of any one of the previous claims wherein the dispersed solid particulate herbicide is flumioxazin.
9. The herbicidal emulsion concentrate of any one of the previous claims wherein the dispersed solid particulate herbicide is present in an amount of from 0.5 g/L to 300 g/L, preferably 10 g/L to 250 g/L of the emulsion concentrate.
10. The herbicidal emulsion concentrate of any one of the previous claims, wherein the water-insoluble herbicide particles are of size in the range of 1 micron to 10 microns such as 2 microns to 8 microns.
11. The herbicidal emulsion concentrate of any one of the previous claims, wherein the continuous phase comprises a water-immiscible liquid herbicide selected from the group consisting of chloroacetamide and chloracetanilide herbicides.
12. The herbicidal emulsion concentrate of any one of claim 10, wherein the water- immiscible liquid herbicide is a chloracetanilide herbicides selected from the group consisting of acetochlor, butachlor, metolachlor (including S-metolachlor) and pretilachlor.
13. The herbicidal emulsion concentrate of any one of the previous claims, wherein the water-insoluble herbicide present in the continuous phase is S-metolachlor.
14. The herbicidal emulsion concentrate of any one of the previous claims, wherein the water-insoluble herbicide present in the continuous phase is present in an amount of 10 g/L to 900 g/L, preferably 300 g/L to 850 g/L of the emulsion concentrate.
15. The herbicidal emulsion concentrate of any one of the previous claims, wherein the water-immiscible continuous phase comprises a water-immiscible solvent.
16. The herbicidal emulsion concentrate of any one of the previous claims, wherein the water-immiscible continuous phase comprises a water-immiscible solvent selected from the group consisting of aliphatic, cycloaliphatic and aromatic hydrocarbons.
17. The herbicidal emulsion concentrate of any one of the previous claims, wherein the water-immiscible continuous phase comprises a water-immiscible solvent present in an amount of no more than 50 wt%, preferably no more than 20 wt% of the water- immiscible phase.
18. The herbicidal emulsion concentrate of any one of the previous claims, wherein the dispersed aqueous phase comprises a dissolved water-soluble herbicide selected from at least one of the group consisting of: organophosphorus herbicides such as glyphosate salts, glufosinate salts such as glufosinate ammonium (which may be glufosinate-P, such as glufosinate-P; salts of imidazolinone herbicides such as imazethapyr, particularly imazethapyr-ammonium; and auxin herbicide salts including salts of one or more aryloxy herbicides such as 2,4-D, MCPA, clopyralid, dichlorprop, triclopyr and mecoprop; salts of one or more aromatic acid herbicides such as dicamba, aminopyralid, clopyralid and picloram.
19. The herbicidal emulsion concentrate of any one of the previous claims, wherein the dispersed aqueous phase comprises a dissolved water-soluble herbicide selected from the group consisting of glyphosate salts, glufosinate-ammonium and imazethapyr-ammonium.
20. The herbicidal emulsion concentrate of any one of the previous claims, wherein the dispersed aqueous phase comprises imazethapyr-ammonium.
21. The herbicidal emulsion concentrate of any one of the previous claims, wherein the dispersed aqueous phase comprises a dissolved herbicide present in an amount of 0.5 g/L to 500 g/L, preferably 10 g/L to 400 g/L of emulsion concentrate.
22. The herbicidal emulsion concentrate of any one of the previous claims comprising one or more dispersants.
23. The herbicidal emulsion concentrate of claim 21 wherein the one or more dispersants are at least one selected from the group consisting of sodium lignosulfonate, naphthalene sulfonate-formaldehyde condensates; polycarboxylates; comb-type graft copolymers; and ethoxylated tristyrylphenol sulfates.
24. The herbicidal emulsion concentrate claim 21 or claim 22 wherein the dispersant is present in an amount of from 5 g/L to 100 g/L, preferably 8 g/L to 50 g/L of the aqueous phase.
25. The herbicidal emulsion concentrate composition comprising: a continuous water-immiscible (oil) phase comprising S-metolachlorfrom in an amount of 650 g/L to 850 g/L of emulsion; a discontinuous aqueous phase comprising filumioxazin dispersed solid particulate herbicide in an amount of 10 g/L to 10Og/L of the emulsion concentrate;
Imazethapyr dissolved in the discontinuous aqueous phase in an amount of 50 g/L to 200 g/L of the emulsion concentrate; a surfactant in the aqueous phase in an amount of from 8 g/L to 50 g/L of the aqueous phase; an oil in water emulsifier of HLB 3 to 7 present in an amount of from 5 g/L to 80 g/L of emulsion concentrate.
26. The herbicidal emulsion concentrate composition of any one of the previous claims further comprising a thickener, an antifoam and an antifreeze.
27. A method of preparing the emulsion concentrate composition of any one of the previous claims comprising, the method comprising; combining a fine suspension of solid water-insoluble herbicide, preferably comprising a polymeric dispersant, with a water-soluble herbicide, preferably as an aqueous solution of the water-soluble herbicide to form an aqueous composition; and dispersing the aqueous composition in a composition comprising a water- insoluble herbicide in the presence of a water-in-oil type emulsifier to form the emulsion.
28. A method for control of weeds in an area comprising applying the herbicidal emulsion composition, optionally following dilution with water, to the site in which weed control is required.
PCT/AU2021/050042 2020-01-28 2021-01-25 Herbicidal emulsion concentrate WO2021151143A1 (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999045780A1 (en) * 1998-03-09 1999-09-16 Monsanto Company Concentrate herbicidal composition
WO2009103455A2 (en) * 2008-02-20 2009-08-27 Syngenta Participations Ag. Herbicide formulation
CN102939972A (en) * 2012-12-04 2013-02-27 张荣宝 Weeding composition and preparation thereof
CN107535505A (en) * 2016-06-28 2018-01-05 佛山市盈辉作物科学有限公司 Herbicidal combinations containing S-metolachlor and flumioxazin
CN108935507A (en) * 2018-08-01 2018-12-07 四川利尔作物科学有限公司 Agricultural active ingredients and its application
CN109479877A (en) * 2018-11-26 2019-03-19 浙江天丰生物科学有限公司 A kind of sunflower field herbicidal composition
WO2019236738A1 (en) * 2018-06-05 2019-12-12 Monsanto Technology Llc Herbicidal compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999045780A1 (en) * 1998-03-09 1999-09-16 Monsanto Company Concentrate herbicidal composition
WO2009103455A2 (en) * 2008-02-20 2009-08-27 Syngenta Participations Ag. Herbicide formulation
CN102939972A (en) * 2012-12-04 2013-02-27 张荣宝 Weeding composition and preparation thereof
CN107535505A (en) * 2016-06-28 2018-01-05 佛山市盈辉作物科学有限公司 Herbicidal combinations containing S-metolachlor and flumioxazin
WO2019236738A1 (en) * 2018-06-05 2019-12-12 Monsanto Technology Llc Herbicidal compositions
CN108935507A (en) * 2018-08-01 2018-12-07 四川利尔作物科学有限公司 Agricultural active ingredients and its application
CN109479877A (en) * 2018-11-26 2019-03-19 浙江天丰生物科学有限公司 A kind of sunflower field herbicidal composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GRICHAR, W. ET AL.: "Interaction of Flumioxazin with Dimethenamid or Metolachlor in Peanut (Arachis hypogaea L.", PEANUT SCIENCE, vol. 31, 2004, pages 12 - 16, XP055846803 *
WILSON, D. ET AL.: "Potato (Solanum tuberosum) Variety and Weed Response to Sulfentrazone and Flumioxazin", WEED TECHNOLOGY, vol. 16, no. 3, 2002, pages 567 - 574 *

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CO2022010626A2 (en) 2022-11-08
BR112022014742A2 (en) 2022-09-20

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