WO2019034934A1 - Formulation dispersable dans l'huile - Google Patents

Formulation dispersable dans l'huile Download PDF

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Publication number
WO2019034934A1
WO2019034934A1 PCT/IB2018/001019 IB2018001019W WO2019034934A1 WO 2019034934 A1 WO2019034934 A1 WO 2019034934A1 IB 2018001019 W IB2018001019 W IB 2018001019W WO 2019034934 A1 WO2019034934 A1 WO 2019034934A1
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WIPO (PCT)
Prior art keywords
formulation
stable formulation
stable
amount
aqueous liquid
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PCT/IB2018/001019
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English (en)
Inventor
Vladimir GUBRIY
Shlomo WINDREICH
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Adama Agan Ltd.
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Publication date
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Priority to CN201880052736.XA priority Critical patent/CN110996660A/zh
Publication of WO2019034934A1 publication Critical patent/WO2019034934A1/fr

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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
    • A01N43/72—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
    • A01N43/82—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 three ring hetero atoms
    • 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
    • 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
    • A01N25/22—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 ingredients stabilising the active ingredients
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present subject matter relates to pesticidal compositions for use in agricultural pest control applications.
  • this subject matter provides a stable herbicidal liquid formulation comprising flufenacet and at least one sulfonylurea herbicide.
  • Sulfonylureas and oxyacetamides are generally known to have herbicidal activity.
  • Sulfonylurea herbicides are acetolactate synthase (ALS) or acetohydroxyacid synthase (AHAS) inhibitors. They act by inhibiting biosynthesis of branched-chain amino acids, such as valine and isoleucine, thereby inhibiting cell division and plant growth.
  • ALS acetolactate synthase
  • AHAS acetohydroxyacid synthase
  • Oxyacetamide herbicides including flufenacet, inhibit fatty acid metabolism thereby also inhibiting cell division and plant growth .
  • Flufenacet an oxyacetamide herbicide, is a highly sensitive molecule which rapidly decomposes in various conditions.
  • N-isomer of flufenacet which is less active and/or more toxic, is one of the decomposition products of flufenacet.
  • Sulfonylurea herbicides and oxyacetamide herbicides are each formulated as solid and liquid formulations in presence of stabilizing agents such as pH adjuster.
  • Sulfonylurea herbicides are sensitive to acidic conditions and hydrolyzed rapidly in aqueous and/or acid environment. Sulfonylurea herbicides can be stable at pH values above 7.
  • Flufenacet is not stable in neutral or basic conditions. In neutral or basic conditions, isomerization of the molecule takes place causing rapid formation and accumulation of N-isomers .
  • flufenacet is formulated as a solid composition and stabilized with acid.
  • EP922388B discloses solid dry compositions where the flufenacet is stabilized by adding an amount of citric acid to reduce the pH of the composition and thus preventing the formation of N-isomer.
  • liquid formulations are preferred due to the advantage of better miscibility which reduces problems of flowability . Accordingly, the problem to be solved by the subject invention is to combine sulfonylurea and flufenacet into a single stable liquid formulation.
  • stable liquid formulations comprising both sulfonylurea herbicide (s) and flufenacet.
  • the present invention provides a stable herbicidal non-aqueous liquid formulation comprising: a) an amount of flufenacet;
  • the subject application also provides a method for controlling weeds comprising applying the stable herbicidal non-aqueous liquid formulation described herein to a weed, a portion of a weed, an area or soil adjacent to a weed, and/or a seed of a weed so as to thereby control the weeds.
  • the subject application also provides a method of controlling weed comprising: a) obtaining a stable herbicidal non-aqueous liquid formulation comprising an amount of flufenacet, an amount of at least one sulfonylurea herbicide; and an agrochemically acceptable non-aqueous liquid carrier, wherein in the flufenacet is dissolved in the non-aqueous liquid carrier and the sulfonylurea herbicide is suspended in the non-aqueous liquid carrier, and b) applying the stable herbicidal formulation to a weed, a portion of a weed, an area or soil adjacent to a weed, and/or a seed of a weed so as to thereby control the weed.
  • the present invention also provides a process for preparing the stable herbicidal non-aqueous liquid formulation described herein, wherein the method comprises the steps of:
  • step (i) dissolving the flufenacet in the non-aqueous carrier to form a solution; adding the sulfonamide herbicide to the solution of step (i) to form a suspension;
  • the term "about” when used in connection with a numerical value includes ⁇ 10% from the indicated value.
  • all ranges directed to the same component or property herein are inclusive of the endpoints, are independently combinable, and include all intermediate points and ranges. It is understood that where a parameter range is provided, all integers within that range, and tenths thereof, are also provided by the invention. For example, “0.1-80%” includes 0.1%, 0.2%, 0.3%, etc. up to 80%.
  • the term “pesticide” broadly refers to an agent that can be used to control and/or kill a pest.
  • the term is understood to include but is not limited to fungicides, insecticides, nematicides, herbicides, acaricides, parasiticides or other control agents.
  • fungicides insecticides, nematicides, herbicides, acaricides, parasiticides or other control agents.
  • specific compounds of each class see "The Pesticide Manual Thirteenth Edition” (British Crop Protection Council, Hampshire, UK, 2003) , as well as “The e- Pesticide Manual, Version 3" (British Crop Protection Council, Hampshire, UK, 2003-04), the contents of each of which are incorporated herein by reference in their entirety.
  • weed includes any undesired vegetation.
  • the term "plant” or “crop” includes reference to whole plants, plant organs (e.g. leaves, stems, twigs, roots, trunks, limbs, shoots, fruits etc.), plant cells, or plant seeds. This term also encompasses plant crops such as fruits.
  • the term "plant” may include the propagation material thereof, which may include all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers, which can be used for the multiplication of the plant.
  • locus includes not only areas where pests, including weeds, may already be growing, but also areas where pests, including weeds, have yet to emerge, and also to areas under cultivation.
  • mixture or “combination” refers, but is not limited to, a combination in any physical form, e.g., blend, solution, alloy, or the like.
  • the term "effective amount” refers to an amount of the compound that, when ingested, contacted with or sensed, is sufficient to achieve a good level of control.
  • agrochemically acceptable carrier means carriers which are known and accepted in the art for the formation of formulations for agricultural or horticultural use.
  • the term "adjuvant” is broadly defined as any substance that itself is not an active ingredient but which enhances or is intended to enhance the effectiveness of the active ingredient with which it is used. Adjuvants may be understood to include, spreading agents, penetrants, compatibility agents, and drift retardants.
  • the term “additive” is defined as any substance that is not an active ingredient but is added to the formulation such as sticking agents, surfactants, synergists, buffers, acidifiers, defoaming agents and thickeners.
  • an “ultra-low naphthalene solvent” is a solvent with a naphthalene concentration of less than 0.1 wt %.
  • a "low naphthalene solvent” is a solvent with a naphthalene concentration of less than 1 wt % .
  • stable when used in connection with a formulation means that no significant decomposition of the active ingredients in the formulation is observable after at least 7 days of storage at a temperature of at least 20°C. For example, no significant amount of flufenacet N-isomer will form after at least 7 days of storage at a temperature of at least 20°C.
  • U.S. Patent No. 6,479,432 disclosed a liquid suspension formulation comprising one or more herbicidally active compounds from the group of the sulfonylureas in suspended form and one or more active compounds which are partially or completely dissolved in the formulation.
  • a liquid suspension formulation comprising one or more herbicidally active compounds from the group of the sulfonylureas in suspended form and one or more active compounds which are partially or completely dissolved in the formulation.
  • sul fonylurea ( s ) and flufenacet will not result in a formulation that is stable as defined above.
  • tank mix means that two or more chemical pesticides or formulations are mixed in the spray tank at the time of spray application.
  • safety refers to an agent that increase the tolerance of plants to herbicides without significantly affecting the effectiveness of the active ingredients .
  • thickener refers to an agent that increase the viscosity of a liquid formulation without substantially changing other properties of the formulation.
  • non-aqueous when used to describe an agrochemically acceptable carrier or a formulation means that the agrochemically acceptable carrier or the formulation is substantially free of water.
  • Water vapor is one of the most abundant atmospheric gases. Some chemical compounds and formulations tend absorb moisture when they are exposed to the water in the atmosphere. The amount and rate of absorption depends on a variety of factors such as the hygroscopic properties of the chemical compound or formulation, atmospheric conditions (ex. humidity) and duration of exposure. Some chemical compounds and formulations also tend to absorb water from other ingredients/components in the formulation. Accordingly, the agrochemically acceptable carriers and formulations of the subject invention may contain slight amounts of water, but they should be deemed "non-aqueous" as long as no water was affirmatively added to the agrochemically acceptable carrier or the formulation.
  • the amount of water absorbed into a compound or a formulation may be measured using a number of techniques including Karl Fischer titration.
  • Agrochemical oil dispersions are stable suspensions of agrochemical active ingredients, such as pesticides and crop protection chemicals, in non-aqueous fluids, which may contain other dissolved active ingredients. Oil dispersions are particularly useful for formulating organic, ' insoluble, and solid active ingredients.
  • Oil dispersion formulations are concentrated non-aqueous liquid formulations which are diluted with water before use to produce an aqueous composition which is - used in crop protection.
  • such formulations contain emulsifiers, dispersants and further formulation components such as thickeners, antifoaming agents and solid carriers.
  • Oil dispersions are often chosen if the active ingredient is sensitive to water or if the oil is required to act as an adjuvant in order to improve biological performance of the pesticide. Oil dispersions are usually free of water. This is to prevent degradation of active ingredients and/or phase separation of the formulation .
  • Oil dispersion formulations provide certain advantages to the farmer. Active ingredients which are usually unstable in water may now be formulated in solid suspended form. Oil-based adjuvants may also be combined with these types of formulations in order to enhance efficacy. Further, suspension of active ingredients in non-aqueous liquid carrier can possibly lead to formulations with higher concentration of active ingredient than would otherwise be possible. This is because active ingredients have a solubility limit on the amount that can be added into a formulation .
  • non-aqueous liquid formulation may include an adjuvant and/or safener therein, as opposed to adding the adjuvant and/or safener in the spray tank. This further brings logistic, packaging and storage benefits to the farmer, as a single product can be used instead of two or more.
  • the non-aqueous liquid formulation of the present invention comprising flufenacet and at least one sulfonylurea herbicide was found to be stable and no decomposition products of flufenacet were formed, when the formulation was stored at various conditions and for various durations.
  • a major advantage of this formulation is its ability to suspend at least one sulfonylurea herbicide in non-aqueous liquid carrier and dissolve flufenacet without loss of stability of the formulation.
  • EC emulsifiable concentrate
  • SC suspenpension concentrate
  • WG water dispersible granule
  • the present invention provides a stable herbicidal non-aqueous liquid formulation comprising: a) an amount of flufenacet;
  • the sulfunylurea herbicide is azimusulfuron, flazasulfuron, thifensulfuron, flucetosufuron, mesosulfuron, or nicosulfuron . In some embodiments, the sulfonylurea herbicide is mesosulfuron .
  • Non-aqueous liquid carriers refer but is not limited to esters, amides, aromatic hydrocarbons, paraffins, petroleum, vegetable oil, alkyl ester of vegetable oils, alkyl phosphate, diesel, mineral oil, fatty acid amides, fatty acids, tall oil fatty acids, alkyl esters of fatty acids, modified vegetable oils and any combination thereof.
  • the non-aqueous liquid carrier is selected , from a group consisting of esters, amides, aromatic hydrocarbons, paraffins, petroleum, vegetable oil, alkyl ester of vegetable oils, alkyl phosphate, diesel, mineral oil, fatty acid amides, fatty acids, tall oil fatty acids, alkyl esters of fatty acids, modified vegetable oils and any combination thereof .
  • the non-aqueous liquid carrier is selected from a group consisting of aromatic hydrocarbons, paraffins, petroleum, diesel, mineral oil, fatty acids, tall oil fatty acids, and any combination thereof.
  • the non-aqueous liquid carrier is an aromatic hydrocarbon. In some embodiments, the non-aqueous liquid carrier is a combination of aromatic hydrocarbon and one or more additional non-aqueous liquid carrier.
  • the aromatic hydrocarbon is selected from a group consisting of toluene, o-xylene, m-xylene, p-xylene, ethylbenzene , isopropylbenzene , tert- butylbenzene , naphthalenes, and mono- or polyalkyl-substituted naphthalenes .
  • the aromatic hydrocarbon is a CIO aromatic hydrocarbon. In some embodiments, the aromatic hydrocarbon is a C12 aromatic hydrocarbon. In some embodiments, the aromatic hydrocarbon is ultra-low naphthalene solvent (ULN) . In some embodiments, the aromatic hydrocarbon is low naphthalene solvent (LN) .
  • the aromatic hydrocarbon is the SolvessoTM grades from ExxonMobil Chemical, especially SolvessoTM 100 (CAS No. 64742-95-6), SolvessoTM 150 (CAS No. 64742-94-5), and SolvessoTM 200 (CAS No. 64742-94-5) .
  • the aromatic hydrocarbon is CaromaxTM 28 LN (sold by Petrochem Carless ) .
  • the non-aqueous liquid carrier is a paraffin.
  • the paraffin is selected from a group consisting of octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, hepta-decane , octa-decane, nona-decane, eicosane, heneicosane, docosane, tricosane, tetracosane, pentacosane, and branched chain isomers thereof .
  • the alkyl ester of fatty acid is a methyl ester of fatty acid.
  • the methyl ester of fatty acid is methyl caprylate/caprate.
  • the methyl caprylate/caprate is StepanTM C-25 (sold by the Stepan Company) .
  • the non-aqueous liquid carrier is a vegetable oil.
  • the vegetable oil is selected from a group consisting of olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cotton seed oil, soybean oil, rapeseed oil, ., linseed oil, tung oil, sunflower oil, safflower oil, and tall oil.
  • the non-aqueous liquid carrier is an alkyl ester of vegetable oil.
  • the alkyl ester of vegetable oils is selected from a group consisting of rapeseed oil methyl ester, rapeseed oil ethyl ester, rapeseed oil propyl esters, rapeseed oil butyl esters, and tall oil fatty acids esters .
  • the non-aqueous liquid carrier is a fatty acid amide.
  • the fatty acid amide is selected from a group consisting of C1-C3 amines, alkylamines and alkanolamines with C 6 - Cis carboxylic acids.
  • the non-aqueous liquid carrier is an alkyl ester of fatty acids.
  • the alkyl ester of fatty acids is selected from a group consisting of C1-C4 monohydric alcohol esters of Cs to C22 fatty acids such as methyl oleate and ethyl oleate.
  • the non-aqueous liquid carrier is substantially free of water. In some embodiments, the non ⁇ aqueous liquid carrier comprises an amount of water less than or equal to 1.5%, or 1%, or 0.7%, or 0.5%, or 0.2% or 0.1% by weight. In some embodiments, the non-aqueous liquid carrier comprises 0.16% of water by weight. In some embodiments, the non-aqueous liquid carrier is free of water.
  • the non-aqueous liquid formulation is substantially free of water. In some embodiments, the nonaqueous liquid formulation comprises water less than or equal to 1.5%, or 1%, or 0.7%, or 0.5%, or 0.2% or 0.1% by weight. In some embodiments, the non-aqueous liquid formulation comprises 0.16% of water by weight. In some embodiments, the non-aqueous liquid formulation is free of water.
  • the amount of water in the non-aqueous liquid carrier is measured by Karl Fischer titration. In some embodiments, the amount of water in the non-aqueous liquid formulation is measured by Karl Fischer titration. In some embodiments, the non-aqueous liquid carrier has no basic nature .
  • the non-aqueous liquid carrier is other than vegetable oil. In some embodiments, the non-aqueous carrier is other than rapeseed oil. In some embodiments, the non-aqueous carrier is other than rapeseed oil methyl ester.
  • the non-aqueous liquid carrier is other than dimethyl amides of fatty acids. In some embodiments, the non-aqueous carrier is other than methyl ester of fatty acids. In some embodiments, the non-aqueous carrier is other than morpholine amides of fatty acids.
  • the non-aqueous liquid carrier is other than N-octyl-2-pyrrolidone .
  • the amount of the flufenacet is 0.1-80% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the flufenacet is 0.1-70% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the flufenacet is 1-60% by weight based on the total weight of the stable formulation. In some embodiments, the amount of flufenacet is 5-50% by weight based on the total weight of the stable formulation. In some embodiments, the amount of flufenacet is 1-15% by weight based on the total weight of the stable formulation. In some embodiments, the amount of flufenacet is 10-20% by weight based on the total weight of the stable formulation. In some embodiments, the amount of flufenacet is 13% by weight based on the total weight of the stable formulation.
  • the concentration of the flufenacet in the stable formulation is between 50 to 500 g/L. In some embodiments, the concentration of the flufenacet in the stable formulation is between 50 to 300 g/L. In some embodiments, the concentration of the flufenacet in the stable formulation is between 100 to 200 g/L. In some embodiments, the concentration of the flufenacet in the stable formulation is between 100 to 150 g/L. In some embodiments, the concentration of the flufenacet in the stable formulation is about 128 g/L.
  • the amount of the sulfonylurea herbicide is 0.1-80% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the sulfonylurea herbicide is 0.1-70% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the sulfonylurea herbicide is 0.1-60% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the sulfonylurea herbicide is 0.1-40% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the sulfonylurea herbicide is 0.1-25% by weight based on the total weight of the stable formulation.
  • the amount of the sulfonylurea herbicide is 0.1-1% by weight based on the total weight of the stable formulation. In a specific embodiment, the amount of the sulfonylurea herbicide is 0.5% by weight based on the total weight of the stable formulation.
  • the concentration of the sulfonylurea in the stable formulation is between 1 to 50 g/L. In some embodiments, the concentration of the sulfonylurea in the stable formulation is between 1 to 25 g/L. In some embodiments, the concentration of the sulfonylurea in the stable formulation is between 1 to 10 g/L. In some embodiments, the concentration of the sulfonylurea in the stable formulation is about 5 g/L.
  • the amount of the flufenacet and the at least one sulfonylurea herbicide is 0.1-90% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the flufenacet and the at least one sulfonylurea herbicide is 0.5-30% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the flufenacet and the at least one sulfonylurea herbicide is 1-15% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the flufenacet and the at least one sulfonylurea herbicide is 1-10% by weight based on the total weight of the stable formulation.
  • the amount of the flufenacet and the at least one sulfonylurea herbicide is 3-8% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the flufenacet and the at least one sulfonylurea herbicide is about 15% by weight based on the total weight of the stable formulation .
  • the concentration of the flufenacet and the sulfonylurea in the stable formulation is between 50 to 500 g/L. In some embodiments, the concentration of the flufenacet and the sulfonylurea in the stable formulation is between 50 to 300 g/L. In some embodiments, the concentration of the flufenacet and the sulfonylurea in the stable formulation is between 100 to 200 g/L. In some embodiments, the concentration of the flufenacet and the sulfonylurea in the stable formulation is between 100 to 150 g/L. In some embodiments, the concentration of the flufenacet and the sulfonylurea in the stable formulation is about 132 g/L.
  • the amount of the non-aqueous liquid carrier is 10-90% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the non-aqueous liquid carrier is 40-90% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the non-aqueous liquid carrier is 50-80% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the non-aqueous liquid carrier is 60-80% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the non-aqueous liquid carrier is 70-80% by weight based on the total weight of the stable formulation.
  • the amount of the non-aqueous liquid carrier is 75- 80% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the non-aqueous liquid carrier is 77% by weight based on the total weight of the stable formulation.
  • the concentration of the non-aqueous liquid carrier in the stable formulation is 300-900 g/L. In some embodiments, the concentration of the non-aqueous liquid carrier in the stable formulation is 400-700 g/L. In some embodiments, the concentration of the non-aqueous liquid carrier in the stable formulation is 500-600 g/L. In some embodiments, the concentration of the non-aqueous liquid carrier in the stable formulation is 575-600 g/L.
  • the formulation comprises at least one surfactant .
  • Surfactants may include but are not limited to alkyl-end-capped ethoxylate glycol, alkyl-end-capped alkyl block alkoxylate glycol, dialkyl sulfosuccinate , phosphated esters, alkyl sulfonates, alkyl aryl sulfonates, tristyrylphenol alkoxylates, natural or synthetic fatty acid alkoxylates, natural or synthetic fatty alcohols alkoxylates, alkoxylated alcohols (such as n-butyl alcohol poly glycol ether) , block copolymers (such as ethylene oxide-propylene oxide block copolymers and ethylene oxide-butylene oxide block copolymers) or combinations thereof.
  • surfactant is an alkyl-end-capped alkoxylate.
  • the adjuvant is a methyl-end- capped ethoxylate.
  • the adjuvant is a methyl- end-capped tridecyl ethoxylate.
  • the adjuvant is a methyl-end-capped tridecyl ethoxylate with six ethylene oxides.
  • the surfactant is Genapol® XM-60.
  • Genapol® XM-60 (CAS No. 345642-79-7, sold by Clariant) is a methyl-end- capped ethoxylate based on Genapol® X 060 (CAS No. 9043-30-5, sold by Clariant) .
  • the surfactant is selected from group consisting of synthetic end capped alcohol alkoxylates and alkyl aryl sulphonates .
  • the surfactant is calcium dodecylbenzene sulfonate.
  • the surfactant is Nansa® EVM 70/2E (sold by Huntsman International LLC) .
  • the surfactant is other than an isotridecyl alcohol polyglycol ether (6EO) .
  • the surfactant is other than an isotridecyl alcohol polyglycol ether (8EO) .
  • the surfactant is other than Genapol® X 060.
  • the surfactant is other than Genapol® X 080 (CAS 9043-30-5, sold by Clariant) . In some embodiments, the surfactant is other than an anionic sulfosuccinate . In some embodiments, the surfactant is other than a dioctyl sulfosuccinate . In some embodiments, the surfactant is other than 1 , 4-Bis ( 2-ethylhexyl ) sodium sulfosuccinate . In some embodiments, the surfactant is other than TRITONTM GR-7ME (CAS No. 577-11-7, sold by The Dow Chemical Company) or TRITONTM GR- 7M (CAS No.
  • the surfactant is other than a mixture of fatty acid polyethylene glycol esters. In some embodiments, the surfactant is other than ALKAMULS® VO/2003 (CAS No. 220037-02- 5, sold by Rhodia Operations, a member of the SOLVAY Group.
  • the amount of surfactants present in the stable formulation is between 0.1-40% by weight based on the total weight of the stable formulation. In some embodiments, the amount of surfactants present in the stable formulation is between 0.1-35% by weight based on the total weight of the stable formulation. In some embodiments, the amount of surfactants present in the stable formulation is between 0.1-30% by weight based on the total weight of the stable formulation. In some embodiments, the amount of surfactants present in the stable formulation is between 1-20% by weight based on the total weight of the stable formulation. In some embodiments, the amount of surfactants present in the stable formulation is between 5-10% by weight based on the total weight of the stable formulation. In some embodiments, the amount of surfactants present in the stable formulation is about 17% by weight based on the total weight of the formulation.
  • the formulation further includes at least one adjuvant .
  • the adjuvant is selected from a group consisting of alkyl ethoxylate glycol, alkyl block alkoxylate glycol, alkyl-end-capped ethoxylate glycol, alkyl-end-capped alkyl block alkoxylate glycol, dialkyl sulfosuccinate, ethoxylated alcohols, phosphated esters, ethoxylated tristyryl phenol phosphate, sorbitan esters, Tween esters and combinations thereof .
  • alkyl-end-capped alkyl block alkoxylate glycol when used as the emulsifier, it can also function as an adjuvant.
  • the adjuvant is added to the formulation as tank mix, simultaneously or separately.
  • the adjuvant is present in an amount of at least 0.1% by weight based on the total weight of the stable formulation. In some embodiments, the adjuvant is present in an amount of at least 5% by weight based on the total weight of the stable formulation. In some embodiments, the adjuvant is present in an amount of at least 10% by weight based on the total weight of the stable formulation. In some embodiments, the adjuvant is present in an amount of at least 15% by weight based on the total weight of the stable formulation. In some embodiments, the adjuvant is present in an amount of at least 20% by weight based on the total weight of the stable formulation. In some embodiments, the adjuvant is present in an amount of at least 30% by weight based on the total weight of the stable formulation.
  • the formulation further include additional physical stabilizer such as buffers, acidifiers, defoaming agents, thickeners and drift retardants.
  • Thickener useful herein are silica, silica organo modified bentonites, inorganic clays and any combination thereof.
  • Silica may be a fumed and precipitated silica and any combination thereof .
  • Fumed and precipitated silica may be hydrophobic and hydrophilic silica and any combination thereof.
  • fumed silica examples include in the formulation of the subject invention but are not limited to Aerosil® A 200, Aerosil® R 202, Aerosil® R 972 and Aerosil® R 805 (all sold by Evonik) .
  • Examples of precipitated silica that may include in the formulation of the subject invention but are not limited to Sipernat® 22S (sold by Evonik) , Sipernat® D17 (sold by Evonik) and Tixosil® 38 (sold by Rhodia Operations, a member of the Solvay Group) .
  • organo modified bentonite that may be used in the formulation of the subject invention is Bentone® SD-1 (sold by Elementis Specialties) .
  • inorganic clays that may be used in the formulation of the subject invention is Attagel® 40 (sold by BASF) .
  • adjuvants that may be used in the formulations of the subject invention include sticking agents, spreading agents, synergists, penetrants, compatibility agents, buffers, acidifiers, defoaming agents, and drift retardants .
  • the stable formulation further comprises a safener .
  • the safeners is selected from a group consisting of mefenpyr diethyl, cloquintocet mexyl, fenchlorazole ethyl, benoxacor, dichlormid, isoxadifen ethyl, and any combination thereof.
  • the safener is mefenpyr diethyl.
  • the safener is added to the formulation as tank mix, simultaneously or separately.
  • the amount of the safener in the stable formulation is 0.1-80% by weight based on the total weight of the stable formulation. In some embodiments, the amount of safener in the stable formulation is 1-50% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the safener in the stable formulation is 1-25% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the safener in the stable formulation is 1-15% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the safener in the stable formulation is 1-10% by weight based on the total weight of the stable formulation. In some embodiments, the amount of the safener in the stable formulation is 1-5% by weight based on the total weight of the stable formulation.
  • ingredients such as adhesives, neutrali zers , binders, sequestrates, biocides, stabilizers, buffers preservatives, antioxidants or anti-freeze agents, may also be added to the present compositions in order to increase the stability, density, and viscosity of the described compositions.
  • the stable formulation is an oil formulation. In some embodiments, the stable formulation is an oil dispersible formulation.
  • the stable formulation comprises: a) 1.0-15% by weight of flufenacet; b) 0.1-25% by weight of at least one sulfonylurea herbicide; c) 10-90% by weight of a non-aqueous liquid carrier; and d) optionally, 0.1-30% by weight of safener and/or adjuvant.
  • the formulation is stable after 7 days in storage. In some embodiments, the formulation is stable after 10 days in storage. In some embodiments, the formulation is stable after 14 days.
  • the formulation is stored at a temperature between 20 to 55 °C. In some embodiments, the formulation is stored at a temperature between 40 to 55 °C. In some embodiments, the formulation is stored at a temperature between 50 to 55°C. In some embodiments, the formulation is stored at a temperature of 54°C.
  • the formulation is stable after 14 days in storage at a temperature of 54°C.
  • the formulation comprises less than 5% of flufenacet N-isomer. In some embodiments, the formulation comprises less than 2% of flufenacet N-isomer. In some embodiments, the formulation comprises less than 1% of flufenacet N-isomer. In some embodiments, the formulation comprises less than 0.5% of flufenacet N-isomer. In some embodiments, the formulation comprises less than 0.1% of flufenacet N-isomer. In some embodiments, the formulation comprises an undetectable amount of flufenacet N-isomer. In some embodiments, the formulation comprises no flufenacet N-isomer.
  • the agricultural compositions herein may be used in conjunction with one or more other pesticides to control a wider variety of undesirable pests.
  • the herein described composition may be formulated with the other pesticide ( s ) , tank mixed with the other pesticide (s) or applied sequentially with the other pesticide (s) .
  • the herein described composition may, optionally, be combined with or blended with other pesticide composition ( s ) . This blend with pesticide composition ( s ) may be used to control pests in crops and non-crop environments.
  • the subject invention also provides a method for controlling weed comprising applying the stable herbicidal non-aqueous liquid formulation described herein to a weed, a portion of a weed, an area or soil adjacent to a weed, and/or a seed of a weed so as to thereby control the weed.
  • the subject invention also provides a method of controlling weed comprising : a) obtaining a stable herbicidal non-aqueous liquid formulation comprising an amount of flufenacet, an amount of at least one sulfonylurea herbicide, and an agrochemically acceptable non-aqueous liquid carrier, wherein in the flufenacet is dissolved in the non-aqueous liquid carrier and the sulfonylurea herbicide is suspended in the non-aqueous liquid carrier, and b) applying the stable herbicidal non-aqueous liquid formulation to a weed, a portion of a weed, an area or soil adjacent to a weed, and/or a seed of a weed so as to thereby control the weed.
  • Methods include adding the stable herbicidal non-aqueous liquid formulation to a carrier such as water and using the resulting solution containing the herbicidal organic formulation for spray applications to control weeds in plant or plant propagation material thereof in crop or non-crop environments.
  • a suspo- emulsion may be formed.
  • Effective application rates of the herbicidal composition cannot generally be defined, as it varies depending upon various conditions such as the type of weed, weather conditions, nature of the soil, and the type of crop.
  • the stable herbicidal non-aqueous liquid formulation is generally applied at a rate of about 1 to about 5 L/ha. In a preferred embodiment the stable herbicidal non- aqueous liquid formulation is applied at a rate of about 2 to 3 L/ha. In a specific embodiment the stable herbicidal non-aqueous liquid formulation is applied at a rate of about 2 L/ha. In another specific embodiment the stable herbicidal non-aqueous liquid formulation is applied at a rate of about 3 L/ha. In another specific embodiment the stable herbicidal non-aqueous liquid formulation is applied at a rate of about 2.5 L/ha.
  • the stable herbicidal non-aqueous liquid formulation may be diluted in a carrier such as water in an amount of from about 1 to 100 L of the stable formulation per 1000L of water. In a further embodiment, the stable herbicidal non-aqueous liquid formulation may be diluted in a carrier such as water in an amount of from about 1 to 30 L of the stable formulation per 1000 L of water. In yet another embodiment, the stable herbicidal non-aqueous liquid formulation may be diluted in a carrier such as water in an amount of from about 5 to 15 L of the stable formulation per 1000L of water.
  • crop plants may include, but are not limited to, cereals, soybean, corn, rice, papaya, melon, cacao and coffee.
  • Cereals may include, but are not limited to, wheat, barley, rye and oats.
  • the weeds may include, but are not limited to, grass weeds such as Poa, Lolium and broad leaves.
  • the stable herbicidal non-aqueous liquid formulation described herein may be mixed with water and/or fertilizers and may be applied to a desired locus by any means, such as airplane spray tanks, knapsack spray tanks, cattle dipping vats, farm equipment used in ground spraying (e.g., boom sprayers, hand sprayers), and the like.
  • the desired locus may be soil, plants, and the like.
  • the present stable herbicidal non-aqueous liquid formulation may include additional crop protection agents, for example insecticides, herbicides, fungicides, bactericides, nematicides, molluscicides , growth regulators, biological agents, fertilizers, or mixtures thereof.
  • additional crop protection agents for example insecticides, herbicides, fungicides, bactericides, nematicides, molluscicides , growth regulators, biological agents, fertilizers, or mixtures thereof.
  • the composition can be formulated with these co-agents, tank mixed with these co-agents or applied sequentially with these co- agents .
  • the present invention provides a process for preparing a stable herbicidal non-aqueous liquid formulation comprising an effective amount of flufenacet and an effective amount of at least one sulfonylurea herbicide, wherein the process comprises the steps of:
  • step (ii) adding the sulfonylurea herbicide to the solution of step (i) to form a suspension
  • the non-aqueous carrier - is added during step (ii) .
  • the process further comprise a step of adding at least one surfactant and/or adjuvant to the solution of step (i)- prior to performing step (ii) . In some embodiments, the process further comprise a step of adding at least one surfactant and/or adjuvant to the solution of step (ii) prior to performing step (iii) .
  • the process further comprise a step of adding a safener to the solution of step (i) prior to performing step (ii) .
  • the safener is mefenpyr diethyl.
  • the process further comprise a step of adding at least one surfactant to the solution of step (i) prior to performing step (ii) .
  • the surfactant is calcium dodecylbenzene sulfonate and/or methyl-end-capped ethoxylate .
  • the process further comprises a step of adding a thickener to the suspension of step (ii) prior to performing step (m) .
  • the thickener is fumed silica.
  • the non-aqueous liquid carrier is heated to completely dissolve the flufenacet and/or the additives.
  • Additives may include, but are not limited to, safener and adjuvant .
  • step (i) is performed at a temperature between 15°C to 65°C. In some embodiments, step (i) is performed at a temperature of about 20°C, 30°C, 40°C, 50°C or 60°C.
  • the suspension is milled until 90% of the particles have a particle size of about 1-10 ⁇ . In some embodiments, the suspension is milled until 90% of the particles have a particle size of less than 8 ⁇ .
  • each embodiment disclosed herein is contemplated as being applicable to each of the other disclosed embodiments.
  • the elements recited in formulation embodiments can be used in the method and use embodiments described herein and vise versa.
  • sulfonylurea herbicides are stable in pH value more than 7 and hydrolyze rapidly in aqua and/or acid environment.
  • Flufenacet on the other hand, is stable in acidic conditions. In neutral or basic conditions, flufenacet decomposes, wherein one of the decomposed product is N-isomers which are less active and/or more toxic.
  • the oil dispersion formulation of flufenacet 125 mesosulfuron 5 mefenpyr diethyl 15 was subjected to accelerated storage stability test - 14 days @ 54°C. All active ingredients were found to be stable. No decomposition product of flufenacet (such as N-isomer) were found after accelerated storage.
  • the stable herbicidal non-aqueous liquid formulation exemplified above has significant advantages over the mixtures and formulations which are known in the art. The formulation is physically stable and easy to use in the fields.
  • the formulation was applied to wheat and the results showed that the herbicidal non-aqueous liquid formulation performed at least as well as mixtures and formulations known in the art.

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

Abstract

La présente invention concerne une formulation liquide non aqueuse herbicide stable comprenant une quantité de flufénacet, une quantité d'au moins un herbicide à base de sulfonylurée, et un support liquide non aqueux agrochimiquement acceptable, le flufénacet étant dissous dans le support liquide non aqueux et l'herbicide à base de sulfonylurée étant suspendu dans le support liquide non aqueux. L'invention concerne également des procédés de lutte contre les mauvaises herbes comprenant l'application des formulations stables décrites dans la description et des procédés de préparation des formulations stables décrites dans la description.
PCT/IB2018/001019 2017-08-14 2018-08-13 Formulation dispersable dans l'huile WO2019034934A1 (fr)

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