EP4096400A1 - Compositions de sulfonylurée liquides - Google Patents

Compositions de sulfonylurée liquides

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Publication number
EP4096400A1
EP4096400A1 EP21711356.2A EP21711356A EP4096400A1 EP 4096400 A1 EP4096400 A1 EP 4096400A1 EP 21711356 A EP21711356 A EP 21711356A EP 4096400 A1 EP4096400 A1 EP 4096400A1
Authority
EP
European Patent Office
Prior art keywords
methyl
combination
tribenuron
ethyl
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21711356.2A
Other languages
German (de)
English (en)
Inventor
Charles MANZI-NSHUTI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fmc Ip Technology GmbH
Cheminova AS
Original Assignee
FMC Agricultural Caribe Industries Ltd
Cheminova AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by FMC Agricultural Caribe Industries Ltd, Cheminova AS filed Critical FMC Agricultural Caribe Industries Ltd
Publication of EP4096400A1 publication Critical patent/EP4096400A1/fr
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • 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

  • This invention relates to liquid herbicidal compositions comprising a non-aqueous liquid carrier, at least one sulfonylurea herbicide and at least one inorganic salt selected from alkali metal silicates.
  • the invention also relates to the use of an inorganic salt selected from alkali metal silicates to improve chemical stabilization of sulfonylurea herbicides in liquid compositions that comprise non-aqueous liquid carriers.
  • Sulfonylureas are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth.
  • AHAS acetohydroxy acid synthase
  • ALS acetolactate synthase
  • Sulfonylurea herbicides provide a valued combination of excellent efficacy against weeds with low use rates and very low toxicity to animals.
  • Sulfonylurea herbicides like other agricultural chemicals, can be formulated as concentrates in a variety of different forms, including liquid compositions such as emulsifiable concentrates and solid compositions such as wettable powders and granules.
  • Liquid herbicidal compositions may be preferred over solid compositions because they are easier to handle in measuring, pouring, pumping, diluting and dispersing in water to provide easily sprayed aqueous solutions or dispersions during spraying operations. They may also exhibit superior biological efficacy.
  • Typical liquid formulations include oil-based formulations such as oil dispersions (OD), emulsifiable concentrates (EC), and soluble concentrates (SL) where one or more active ingredients are dissolved in and/or suspended in the liquid media of the formulation.
  • Hydrolysis and/or crystal growth can occur during storage of concentrated liquid formulations in which sulfonylureas are dissolved or dispersed, so that obtaining stable liquid formulations of sulfonylurea herbicides is problematical. Furthermore, some sulfonylurea herbicides are also prone to degradation due to chemical incompatibilities when other herbicidal ingredients are incorporated in the formulation. This makes the development of liquid formulations that comprise sulfonylurea herbicides and additional herbicidal ingredients even more challenging.
  • PCT Patent Application WO2016/102499 discloses a liquid herbicidal composition comprising a non-aqueous liquid carrier, at least one sulfonylurea herbicide and at least one inorganic salt selected from the metal carbonates and metal phosphates.
  • Metal carbonates and metal phosphates are taught therein to improve chemical stabilization of a sulfonylurea herbicide in a liquid composition comprising a non-aqueous liquid carrier.
  • the present invention is based on the surprising finding that the chemical stability of several sulfonylureas in liquid composition comprising a non-aqueous liquid carrier can be improved by incorporating an inorganic salt selected from alkali metal silicates in the composition.
  • This invention provides a liquid herbicide composition
  • a liquid herbicide composition comprising: a non-aqueous liquid carrier; at least one sulfonylurea herbicide; and at least one inorganic salt selected from alkali metal silicates.
  • This invention also relates to a method for improving the chemical stability of a sulfonylurea herbicide in a liquid herbicide composition comprising a non-aqueous liquid carrier, the method comprising including an inorganic salt selected from alkali metal silicates in the composition.
  • This invention also relates to the use of an inorganic salt selected from alkali metal silicates to improve chemical stabilization of a sulfonylurea herbicide in a liquid herbicide composition comprising a non-aqueous liquid carrier.
  • This invention also relates to a method for controlling unwanted vegetation comprising applying a herbicidally effective amount of a composition as defined above to a locus where such control is desired.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains,” “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • a mixture, composition or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such mixture, composition or method.
  • transitional phrase “consisting essentially of’ is used to define a mixture, composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • the term “consisting essentially of’ occupies a middle ground between “comprising” and “consisting of’.
  • the herbicidal composition of this invention is a liquid.
  • liquid is meant that the composition takes the form of a liquid at standard temperature and pressure.
  • Suitable liquid compositions that can be used in the present invention include the oil-based liquid formulations defined in the “Catalogue of pesticide formulation types and interational coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • Exemplary liquid compositions for use in the present invention include a dispersible concentrate (DC), an emulsifiable concentrate (EC), the liquid part(s) of a solid/liquid (KK) or liquid/liquid (KL) combi-pack, an oil dispersion (OD), an oil miscible flowable concentrate (OF), an oil miscible liquid (OL), an oil-based soluble concentrate (SL), a spreading oil (SO), an oil-based ultra-low volume liquid (UL) or suspension (SU), or any other oil-based liquid not yet designated by a specific code in the CropLife monograph (AL).
  • DC dispersible concentrate
  • EC emulsifiable concentrate
  • KK emulsifiable concentrate
  • KL liquid/liquid
  • OD oil disper
  • oil dispersions OD
  • DC dispersible concentrates
  • EC emulsifiable concentrates
  • SL oil-based soluble concentrates
  • the invention is particularly suited to improving the chemical stability of sulfonylureas in oil dispersions (OD), dispersible concentrates (DC), emulsifiable concentrates (EC), and soluble concentrates (SL).
  • OD oil dispersions
  • DC dispersible concentrates
  • EC emulsifiable concentrates
  • SL soluble concentrates
  • oil dispersion is to be understood as meaning a dispersion concentrate based on a non-aqueous liquid carrier in which one or more solid active compounds are suspended and wherein further active ingredients are optionally dissolved in the non-aqueous liquid carrier.
  • at least one sulfonylurea compound is suspended in the non-aqueous liquid carrier. Additional sulfonylurea compounds may be co-suspended and/or dissolved in the non- aqueous liquid carrier.
  • one or more non- sulfonylurea herbicidal compounds may be suspended and/or dissolved in the non-aqueous liquid carrier.
  • the inorganic salt is also suspended in the non-aqueous liquid carrier.
  • non-sulfonylurea herbicidal compound refers to herbicidal compounds other than sulfonylureas.
  • the terms “suspended” and “dissolved” take their ordinary meaning in this technical field. Whether a compound is suspended or dissolved can be determined at standard temperature and pressure.
  • the term “suspended” can be taken to mean that 80 weight% or more, preferably 90 weight% or more, even more preferably 95 weight% or more of the compound in question is suspended as solid particles within the liquid composition whereas the term “dissolved” can be taken to mean that 90 weight% or more, preferably 95 weight% or more, even more preferably 99 weight% or more of the compound in question is dissolved in the liquid composition.
  • Embodiment 1 The composition according to the Summary of the Invention, wherein the inorganic salt comprises a metal selected from sodium (Na) and potassium (K).
  • Embodiment 2. The composition according to the Summary of the Invention or Embodiment 1, wherein the inorganic salt is selected from sodium silicate, sodium metasilicate, sodium orthosilicate, sodium trisilicate, sodium pyrosilicate, hydrates thereof, or mixtures thereof.
  • Embodiment 3 The composition according to Embodiment 2 wherein the inorganic salt comprises sodium silicate.
  • Embodiment 4 The composition according to Embodiment 2 wherein the inorganic salt comprises sodium metasilicate or hydrates thereof.
  • Embodiment 5 The composition according to the Summary of the Invention or any of Embodiments 1 through 4, wherein the inorganic salt further comprises an alkali metal phosphate or alkali metal carbonate
  • Embodiment 5a The composition according to the Summary of the Invention or any of Embodiments 1 through 4, wherein the inorganic salt further comprises sodium phosphate.
  • Embodiment 6 The composition according to the Summary of the Invention or any of Embodiments 1 through 5a, which is formulated as an oil dispersion (OD), a dispersible concentrate (DC), an emulsifiable concentrate (EC), or a soluble concentrate (SL).
  • OD oil dispersion
  • DC dispersible concentrate
  • EC emulsifiable concentrate
  • SL soluble concentrate
  • Embodiment 7 The composition according to Embodiment 6, which is formulated as an oil dispersion (OD) and wherein the at least one sulfonylurea is suspended in the non- aqueous liquid carrier.
  • OD oil dispersion
  • Embodiment 8 The composition according to the Summary of the Invention or any of Embodiments 1 through 7, wherein the at least one inorganic salt is suspended in the non-aqueous liquid carrier.
  • Embodiment 9. The composition according to the Summary of the Invention or any of Embodiments 1 through 8, wherein the at least one sulfonylurea herbicide is selected from amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron, nicosulfuron, orthosul
  • Embodiment 10 The composition according to Embodiment 9, wherein the at least one sulfonylurea is selected from tribenuron-methyl, thifensulfuron-methyl, metsulfuron- methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron-ethyl, chlorsulfuron, amidosulfuron, and triasulfuron.
  • Embodiment 11 The composition according to Embodiment 10, wherein the at least one sulfonylurea is selected from tribenuron-methyl, thifensulfuron-methyl or metsulfuron-methyl.
  • Embodiment 12 The composition according to Embodiment 11, wherein the at least one sulfonylurea is tribenuron-methyl.
  • Embodiment 13 The composition according to the Summary of the Invention or any of Embodiments 1 through 8, comprising at least two sulfonylurea herbicides.
  • Embodiment 14 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise nicosulfuron and thifensulfuron-methyl.
  • Embodiment 15 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise nicosulfuron and prosulfuron.
  • Embodiment 16 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and iodosulfuron-methyl;
  • Embodiment 17 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and sulfosulfuron.
  • Embodiment 18 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and thifensulfuron-methyl.
  • Embodiment 19 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and bensulfuron methyl.
  • Embodiment 20 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and chlorsulfuron.
  • Embodiment 21 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and chlorimuron-ethyl.
  • Embodiment 22 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise metsulfuron-methyl and tribenuron-methyl.
  • Embodiment 23 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise tribenuron-methyl and thifensulfuron-methyl.
  • Embodiment 24 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise tribenuron-methyl and chlorimuron-ethyl.
  • Embodiment 25 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise tribenuron-methyl and bensulfuron-methyl.
  • Embodiment 26 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise tribenuron-methyl and mesosulfuron.
  • Embodiment 27 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise tribenuron-methyl and iodosulfuron-methyl.
  • Embodiment 28 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise iodosulfuron-methyl and mesosulfuron methyl.
  • Embodiment 29 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise iodosulfuron-methyl and amidosulfuron.
  • Embodiment 30 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise iodosulfuron-methyl and foramsulfuron.
  • Embodiment 31 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise mesosulfuron and iodosulfuron-methyl.
  • Embodiment 32 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise foramsulfuron and iodosulfuron-methyl.
  • Embodiment 33 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise rimsulfuron and thifensulfuron.
  • Embodiment 34 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise rimsulfuron and nicosulfuron.
  • Embodiment 35 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise bensulfuron-methyl and thifensulfuron-methyl.
  • Embodiment 36 The composition according to Embodiment 13 wherein the at least two sulfonyl herbicides comprise thifensulfuron-methyl and chlorimuron-ethyl.
  • Embodiment 37 The composition according to the Summary of the Invention or any of Embodiments 1 through 36, in combination with one or more other biologically active agents selected from herbicidal compounds other than sulfonylureas, plant growth regulants, herbicide safeners, insecticides, insect antifeedants, miticides, nematocides, bactericides and fungicides.
  • herbicidal compounds other than sulfonylureas plant growth regulants, herbicide safeners, insecticides, insect antifeedants, miticides, nematocides, bactericides and fungicides.
  • Embodiment 38 The composition according to Embodiment 37 wherein the other biologically active agent comprises at least one non-sulfonylurea herbicidal compound.
  • Embodiment 39 The composition according to Embodiment 38 comprising a herbicidal mixture comprising (a) a compound selected from sulfonylurea herbicides, N-oxides, and salts thereof, and (b) at least one additional herbicidal active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors other than sulfonylureas, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitor
  • Embodiment 40 The composition according to Embodiment 38, wherein the non- sulfonylurea herbicidal compound is selected from acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, beflubutamid, S-beflubutamid (beflubutamid-M), benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox
  • Embodiment 41 The composition according to Embodiment 40 wherein the non- sulfonylurea herbicidal compound is selected from 2,4-D and esters and salts thereof, acetochlor, aminopyralid, atrazine, bentazone, benzobicyclon, bromobutide, bromoxynil, butachlor, carfentrazone ethyl, clodinafop, clomeprop, clopyralid, cyprosulfamide, daimuron, dicamba, diflufenican, diflupenzopyr, dimethametryn, fenoxaprop-P-ethyl, fentrazamide, florasulam, flumetsulam, flumioxazin, fluroxypyr or an ester thereof, glyphosphate, glyphosate-ammonium, imazapyr, imazethapyr, indanofan, isoxadifen-ethyl,
  • Embodiment 42 The composition according to Embodiment 41 wherein the non- sulfonylurea herbicidal compound is selected from 2,4-D and esters and salts thereof, bromoxynil, carfentrazone ethyl, clodinafop, clopyralid, dicamba, florasulam, fluroxypyr, glyphosphate, mecoprop-P, MCPA, MCPB, pinoxaden, pyroxsulam, quinclorac, and any ester thereof and any salt thereof.
  • the non- sulfonylurea herbicidal compound is selected from 2,4-D and esters and salts thereof, bromoxynil, carfentrazone ethyl, clodinafop, clopyralid, dicamba, florasulam, fluroxypyr, glyphosphate, mecoprop-P, MCPA, MCPB, pinoxaden, py
  • Embodiment 43 The composition according to Embodiment 42 wherein the non- sulfonylurea herbicidal compound is selected from an MCPA ester, fluroxypyr- meptyl, clodinafop-propargyl, pinoxaden and pyroxsulam.
  • Embodiment 44 The composition according to Embodiment 40 comprising tribenuron-methyl in combination with 2,4-D or ester or salt thereof.
  • Embodiment 45 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with MCPB or an ester thereof.
  • Embodiment 46 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with bromoxynil.
  • Embodiment 47 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with glyphosphate.
  • Embodiment 48 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with fluroxypyr or an ester thereof.
  • Embodiment 49 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with dicamba.
  • Embodiment 50 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with mecoprop-P.
  • Embodiment 51 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with MCPA or an ester thereof.
  • Embodiment 52 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with clopyralid.
  • Embodiment 53 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with carfentrazone ethyl.
  • Embodiment 54 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with clodinafop or an ester thereof.
  • Embodiment 55 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with quinclorac.
  • Embodiment 56 The composition according to Embodiment 40, comprising tribenuron-methyl in combination with florasulam.
  • Embodiment 57 The composition according to Embodiment 40, comprising nicosulfuron in combination with dicamba.
  • Embodiment 58 The composition according to Embodiment 40, comprising nicosulfuron in combination with atrazine.
  • Embodiment 59 The composition according to Embodiment 40, comprising nicosulfuron in combination with flumetsulam.
  • Embodiment 60 The composition according to Embodiment 40, comprising nicosulfuron in combination with clopyralid.
  • Embodiment 61 The composition according to Embodiment 40, comprising nicosulfuron in combination with diflupenzopyr.
  • Embodiment 62 The composition according to Embodiment 40, comprising nicosulfuron in combination with metolachlor.
  • Embodiment 63 The composition according to Embodiment 40, comprising nicosulfuron in combination with terbuthylazine.
  • Embodiment 64 The composition according to Embodiment 40, comprising nicosulfuron in combination with mesotrione.
  • Embodiment 65 The composition according to Embodiment 40, comprising nicosulfuron in combination with bentazone.
  • Embodiment 66 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with acetochlor.
  • Embodiment 67 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with carfentrazone ethyl.
  • Embodiment 68 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with imazapyr.
  • Embodiment 69 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with aminopyralid.
  • Embodiment 70 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with fluroxypyr or an ester thereof.
  • Embodiment 71 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with mecoprop-p.
  • Embodiment 72 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with picloram.
  • Embodiment 73 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with pyraflufen ethyl.
  • Embodiment 74 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with propanil.
  • Embodiment 75 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with glyphosate-ammonium.
  • Embodiment 76 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with dicamba.
  • Embodiment 77 The composition according to Embodiment 40, comprising metsulfuron- methyl in combination with 2,4-D or ester or salt thereof.
  • Embodiment 78 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with acetochlor.
  • Embodiment 79 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with butachlor.
  • Embodiment 80 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with daimuron.
  • Embodiment 81 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with mefenacet.
  • Embodiment 82 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with indanofan.
  • Embodiment 83 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with clomeprop.
  • Embodiment 84 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with pretilachlor.
  • Embodiment 85 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with fentrazamide.
  • Embodiment 86 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with thenylchlor.
  • Embodiment 87 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with pentoxazone.
  • Embodiment 88 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with pyriminobac-methyl.
  • Embodiment 89 The composition according to Embodiment 40, comprising bensulfuron-methyl in combination with bromobutide.
  • Embodiment 90 The composition according to Embodiment 40, comprising triflusulfuron methyl in combination with sulfentrazone.
  • Embodiment 91 The composition according to Embodiment 40, comprising iodosulfuron-methyl in combination with isoxadifen-ethyl.
  • Embodiment 92 The composition according to Embodiment 40, comprising iodosulfuron-methyl in combination with propoxycarbazone.
  • Embodiment 93 The composition according to Embodiment 40, comprising iodosulfuron-methyl in combination with diflufenican.
  • Embodiment 94 The composition according to Embodiment 40, comprising iodosulfuron-methyl in combination with fenoxaprop-P-ethyl.
  • Embodiment 95 The composition according to Embodiment 40, comprising iodosulfuron-methyl in combination with thiencarbazone-methyl.
  • Embodiment 96 The composition according to Embodiment 40, comprising mesosulfuron in combination with diflufenican.
  • Embodiment 97 The composition according to Embodiment 40, comprising mesosulfuron in combination with propoxycarbazone.
  • Embodiment 98 The composition according to Embodiment 40, comprising foramsulfuron in combination with isoxadifen ethyl.
  • Embodiment 99 The composition according to Embodiment 40, comprising foramsulfuron in combination with thiencarbazone-methyl.
  • Embodiment 100 The composition according to Embodiment 40, comprising foramsulfuron in combination with cyprosulfamide.
  • Embodiment 101 The composition according to Embodiment 40, comprising foramsulfuron in combination with thiencarbazone-methyl.
  • Embodiment 102 The composition according to Embodiment 40, comprising thifensulfuron-methyl in combination with flumioxazin.
  • Embodiment 103 The composition according to Embodiment 40, comprising chlorimuron-ethyl in combination with acetochlor.
  • Embodiment 104 The composition according to Embodiment 40, comprising chlorimuron-ethyl in combination with flumioxazin.
  • Embodiment 105 The composition according to Embodiment 40, comprising chlorimuron-ethyl in combination with imazethapyr.
  • Embodiment 106 The composition according to Embodiment 40, comprising chlorimuron-ethyl in combination with metribuzin.
  • Embodiment 107 The composition according to Embodiment 40, comprising chlorimuron-ethyl in combination with sulfentrazone.
  • Embodiment 108 The composition according to Embodiment 40, comprising pyrasulfuron-ethyl in combination with pretilachlor.
  • Embodiment 109 The composition according to Embodiment 40, comprising pyrasulfuron-ethyl in combination with benzobicyclon.
  • Embodiment 110 The composition according to Embodiment 40, comprising pyrasulfuron-ethyl in combination with dimethametryn.
  • Embodiment 111 The composition according to Embodiment 40, comprising rimsulfuron in combination with mesotrione.
  • Embodiment 112. The composition according to Embodiment 40, comprising rimsulfuron in combination with metolachlor.
  • Embodiment 113 The composition according to Embodiment 40, comprising rimsulfuron in combination with dicamba.
  • Embodiment 114 The composition according to Embodiment 40 comprising tribenuron-methyl in combination with an MCPA ester.
  • Embodiment 115 The composition according to Embodiment 40 comprising tribenuron-methyl in combination with fluroxypyr-meptyl.
  • Embodiment 116 The composition according to Embodiment 40 comprising tribenuron-methyl in combination with clodinafop-propargyl.
  • Embodiment 117 The composition according to Embodiment 40 comprising tribenuron-methyl in combination with pinoxaden.
  • Embodiment 118 The composition according to Embodiment 40 comprising tribenuron-methyl in combination with pyroxsulam.
  • Embodiment 119 The composition according to Embodiment 40, comprising tribenuron-methyl and thifensulfuron-methyl in combination with fluroxypyr-meptyl.
  • Embodiment 120 The composition according to any of Embodiments 38 through 119, wherein the at least one sulfonylurea herbicide is in combination with at least one non- sulfonylurea herbicidal compound in a single formulation.
  • Embodiment 121 The composition according to Embodiment 120, wherein at least one non-sulfonylurea herbicidal compound is dissolved in the non-aqueous liquid carrier.
  • Embodiment 122 The composition according to the Summary of the Invention or any of Embodiments 1 through 121 wherein the inorganic salt comprises a sodium silicate.
  • Embodiment 123 The composition according to Embodiment 122, wherein the inorganic salt comprises sodium metasilicate and the at least one sulfonylurea comprises tribenuron-methyl, thifensulfuron-methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron-ethyl, chlorsulfuron, amidosulfuron, or triasulfuran.
  • the inorganic salt comprises sodium metasilicate and the at least one sulfonylurea comprises tribenuron-methyl, thifensulfuron-methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron-ethyl, chlorsulfuron, amidosulfuron, or triasulfuran.
  • Embodiment 124 The composition according to Embodiment 123, wherein the sulfonylurea comprises tribenuron-methyl, thifensulfuron-methyl or metsulfuron-methyl.
  • Embodiment 125 The composition according to Embodiment 124, wherein the sulfonylurea comprises tribenuron-methyl.
  • Embodiment 126 The composition according to Embodiment 125, comprising tribenuron-methyl, thifensulfuron-methyl in combination with fluroxypyr-meptyl.
  • Embodiment 127 The composition according to the Summary of the Invention or any of Embodiments 1 through 121 wherein the inorganic salt comprises a sodium silicate.
  • Embodiment 128 The composition according to the Summary of the Invention or any of Embodiments 1 through 124, wherein the sulfonylurea exhibits at least 60% chemical stability when stored at 54 °C for two weeks.
  • Embodiment 129 The composition according to the Summary of the Invention or any of Embodiments 1 through 128, wherein the chemical stability of the sulfonylurea is improved by at least 10% compared to a corresponding liquid composition that does not contain the at least one inorganic salt selected from alkali metal silicates.
  • Embodiment 130 The method for improving the chemical stability of a sulfonylurea herbicide in a liquid composition comprising a non-aqueous liquid carrier according to the Summary of the Invention, wherein the liquid composition comprises a composition according to the Summary of the Invention or any of Embodiments 1 through 129.
  • Embodiment 131 The method according to Embodiment 130, wherein the sulfonylurea exhibits at least 60% chemical stability when stored at 54 °C for two weeks.
  • Embodiment 132 The method according to Embodiment 130 or Embodiment 131, wherein the chemical stability of the sulfonylurea is improved by at least 10% compared to a corresponding liquid composition that does not contain the at least one inorganic salt selected from alkali metal silicates.
  • Embodiment 133 The use of an inorganic salt selected from alkali metal silicates according to the Summary of the Invention wherein the liquid composition is a composition according to the Summary of the Invention or any of Embodiments 1 through 129.
  • Embodiment 134 The use according to Embodiment 133, wherein the sulfonylurea exhibits at least 60% chemical stability when stored at 54 °C for two weeks. Embodiment 135. The use according to Embodiment 133 or Embodiment 134, wherein the chemical stability of the sulfonylurea is improved by at least 10% compared to a corresponding liquid composition that does not contain the at least one inorganic salt selected from alkali metal silicates.
  • Embodiment 136 The method for controlling unwanted vegetation according to the Summary of the Invention wherein the composition comprises a composition according to the Summary of the Invention or any of Embodiments 1 through 129.
  • Embodiments of this invention including Embodiments of the Summary of the Invention or any of Embodiments 1 through 133 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compositions of this invention, but also to the methods or uses of any of the compositions of the invention.
  • Preferred Embodiments include the following.
  • Embodiment P1 A liquid herbicidal composition comprising: a non-aqueous liquid carrier; at least one sulfonylurea herbicide; and at least one inorganic salt selected from alkali metal silicates.
  • Embodiment P2 The composition according to Embodiment P1, wherein the inorganic salt comprises a metal selected from sodium and potassium.
  • Embodiment P3 The composition according to Embodiment P1 or Embodiment P2, wherein the inorganic salt is selected from sodium silicate, sodium metasilicate, sodium orthosilicate, sodium trisilicate, sodium pyrosilicate, hydrates thereof, or mixtures thereof.
  • Embodiment P4 The composition according to any of Embodiments P1 through P3 wherein the inorganic salt comprises sodium silicate.
  • Embodiment P5 The composition according to any of Embodiments P1 through P3 wherein the inorganic salt comprises sodium metasilicate or hydrates thereof.
  • Embodiment P6 The composition according to Embodiment P1 or Embodiment P2, wherein the inorganic salt comprises potassium silicate.
  • Embodiment P7 The composition according to any of Embodiments P1 through P6, which is formulated as an oil dispersion (OD), a dispersible concentrate (DC), an emulsifiable concentrate (EC), or a soluble concentrate (SL).
  • OD oil dispersion
  • DC dispersible concentrate
  • EC emulsifiable concentrate
  • SL soluble concentrate
  • Embodiment P8 The composition according to any of Embodiments P1 through P7, which is formulated as an oil dispersion (OD) and wherein at least one sulfonylurea is suspended in the non-aqueous liquid carrier.
  • Embodiment P9. The composition according to any of Embodiments P1 through P8, wherein at least one inorganic salt is suspended in the non-aqueous liquid carrier.
  • Embodiment P10 The composition according to any of Embodiments P1 through P9, wherein the sulfonylurea herbicide is selected from amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron,
  • Embodiment P11 The composition according to any of Embodiments P1 through P10, wherein the at least one inorganic salt comprises sodium metasilicate and the at least one sulfonylurea is selected from tribenuron-methyl, thifensulfuron-methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron-ethyl, chlorsulfuron, amidosulfuron, and triasulfuron.
  • the at least one inorganic salt comprises sodium metasilicate and the at least one sulfonylurea is selected from tribenuron-methyl, thifensulfuron-methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron-ethyl, chlorsulfuron, amidosulfuron, and triasulfuron.
  • Embodiment P12 The composition according to Embodiment Pll, wherein the at least one sulfonylurea is selected from tribenuron-methyl, thifensulfuron-methyl and metsulfuron-methyl.
  • Embodiment P13 The composition according to Embodiment P12, wherein the at least one sulfonylurea comprises tribenuron-methyl.
  • Embodiment P14 The composition according to any of Embodiments P1 through P10, comprising at least two sulfonylurea compounds, wherein the at least two sulfonylurea compounds are selected from: nicosulfuron and thifensulfuron-methyl; nicosulfuron and prosulfuron; metsulfuron-methyl and iodosulfuron-methyl; metsulfuron-methyl and sulfosulfuron; metsulfuron-methyl and thifensulfuron-methyl; metsulfuron-methyl and bensulfuron methyl; metsulfuron-methyl and chlorsulfuron; metsulfuron-methyl and chlorimuron-ethyl; metsulfuron-methyl and tribenuron-methyl; tribenuron-methyl and thifensulfuron-methyl; tribenuron-methyl and chlorimuron-ethyl; tribenuron-methyl and chlor
  • Embodiment P15 The composition according to any of Embodiments P1 through P14 comprising a herbicidal mixture comprising (a) a compound selected from sulfonylurea herbicides, N-oxides, and salts thereof, and (b) at least one additional herbicidal active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors other than sulfonylureas, (b3) acetyl- CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol- pymvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitor
  • Embodiment P16 The composition according to any of Embodiments P1 through P14, in combination with at least one non-sulfonylurea herbicidal compound.
  • Embodiment P17 The composition according to Embodiment P16, wherein the non-sulfonylurea herbicidal compound is selected from acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein, alachlor, alloxydim, ametryn, amicarbazone, aminocyclopyrachlor and its esters and salts, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, beflubutamid, S-beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxy
  • Embodiment P18 The composition according to Embodiment P17 wherein the non-sulfonylurea herbicidal compound is selected from an MCPA ester, fluroxypyr- meptyl, clodinafop-propargyl, pinoxaden and pyroxsulam.
  • Embodiment P19 The composition according to Embodiment P17 wherein the non-sulfonylurea herbicidal compound is selected from an MCPA ester, fluroxypyr- meptyl, clodinafop-propargyl, pinoxaden and pyroxsulam.
  • composition according to Embodiments P17 or P18 comprising at least one sulfonylurea herbicide in combination with at least one non-sulfonylurea herbicidal compound, wherein the at least one sulfonylurea herbicide in combination with the at least one non-sulfonylurea herbicidal compound is selected from: tribenuron-methyl in combination with 2,4-D or ester or salt thereof; tribenuron-methyl in combination with MCPB; tribenuron-methyl in combination with bromoxynil; tribenuron-methyl in combination with glyphosphate; tribenuron-methyl in combination with fluroxypyr or an ester thereof; tribenuron-methyl in combination with dicamba; tribenuron-methyl in combination with mecoprop-P; tribenuron-methyl in combination with MCPA or an ester thereof; tribenuron-methyl in combination with clopyralid; tribenuron-methyl in combination with carfentrazone eth
  • Embodiment P20 The composition according to any of Embodiments P16 through P19, wherein the at least one sulfonylurea herbicide is in combination with at least one non-sulfonylurea herbicidal compound in a single formulation.
  • Embodiment P21 The composition according to Embodiment P20, wherein at least one non-sulfonylurea herbicidal compound is dissolved in the non-aqueous liquid carrier.
  • Embodiment P22 The composition according to any of Embodiments P1 through P21 wherein the inorganic salt comprises sodium metasilicate.
  • Embodiment P23 The composition according to any of Embodiments P1 through P22, wherein the sulfonylurea comprises tribenuron-methyl, thifensulfuron-methyl or metsulfuron-methyl.
  • Embodiment P24 The composition according to Embodiment P23, wherein the sulfonylurea comprises tribenuron-methyl.
  • Embodiment P25 The composition according to any of Embodiments P1 through P24, comprising tribenuron-methyl and thifensulfuron-methyl in combination with fluroxypyr-meptyl.
  • Embodiment P26 The composition according to any of Embodiments P1 through P21 wherein the inorganic salt comprises potassium silicate.
  • Embodiment P27 The composition according to any of Embodiments P1 through P26, wherein the sulfonylurea exhibits at least 60% chemical stability when stored at 54 °C for two weeks.
  • Embodiment P28 The composition according to any of Embodiments P1 through P27, wherein the chemical stability of the sulfonylurea is improved by at least 10% compared to a corresponding liquid composition that does not contain the at least one inorganic salt selected from metal silicates.
  • Embodiment P29 A method for improving the chemical stability of a sulfonylurea herbicide in a liquid composition, the method comprising including an inorganic salt selected from alkali metal silicates in the composition to provide a composition of any of Embodiments P1 through P28.
  • Embodiment P30 Use of an inorganic salt selected from alkali metal silicates to improve chemical stabilization of a sulfonylurea herbicide in a liquid composition according to any of Embodiments P1 through P28.
  • Embodiment P31 A method for controlling unwanted vegetation comprising applying a herbicidally effective amount of a composition according to any of Embodiments P1 through P28 to a locus where such control is desired.
  • This invention provides a liquid composition comprising one or more sulfonylurea herbicides amounting from about 0.1 to about 20%, more typically from about 0.5 to about 10%, by weight of the composition.
  • Sulfonylurea herbicides, salts and esters thereof are well known in the art and can be prepared as described in W02007/027863,.
  • amidosulfuron N-[[[[[(4,6-dimethoxy-2-pyrimdinyl)amino]carbonyl]amino]sulfonyl]-N-methyl- methanesulfonamide
  • azimsulfuron N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1- methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide
  • bensulfuron-methyl methyl 2-[[[[[[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoate
  • chlorimuron-ethyl ethyl 2-[[[[[[(4-chloro-6-methoxy-2-pyrimidinyl
  • Example sulfonylureas for use in the compositions of this invention include amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron,
  • Preferred sulfonylureas for use in the compositions of this invention include tribenuron- methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron- ethyl, chlorsulfuron, amidosulfuron, and triasulfuron. More preferred, the sulfonylurea comprises tribenuron-methyl. Also of note are compositions comprising a combination of tribenuron-methyl and thifensulfuron-methyl.
  • Salts of sulfonylureas can include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • Preferred salts of sulfonylureas include lithium, sodium, potassium, triethylammonium, and quaternary ammonium salts.
  • Preferred salts of the sulfonylureas mentioned above include the sodium salt thereof and the potassium salt thereof.
  • Salts of sulfonylureas can be prepared by ways known in the art, including contact of a sulfonylurea with an acid or base, or using ion exchange with a sulfonylurea salt.
  • the sulfonylurea preferably comprises an amount of at least 0.1 weight% based on the total weight of the liquid composition.
  • the sulfonylurea preferably comprises in an amount of 60 weight% or less based on the total weight of the liquid composition. More preferably, the sulfonylurea comprises an amount in a range from a lower limit of at least 0.2 weight%, 0.5 weight%, 0.7 weight%, 1 weight%, 2 weight%, 5 weight% or 7 weight% to an upper limit of 50 weight%, 40 weight%, 30 weight%, 25 weight%, 20 weight%, 10 weight%, 5 weight%, 2 weight%, or 1 weight%.
  • any of the preferred lower weight% limits of the amount of sulfonylurea can be combined with any of the preferred upper weight% limits to define further suitable weight% ranges for the present invention.
  • Exemplary ranges of the amount of sulfonylurea in the liquid composition include 0.1 to 60 weight%, 1 to 50 weight%, 2 to 40 weight%, 5 to 30 weight%, 0.5 to 20 weight%, 7 to 30 weight%, 5 to 10 weight%, 0.2 to 5 weight%, 0.5 to 2 weight% and 0.5 to 1 weight%.
  • the weight% amounts that are described herein refer to the weight amount of the modified sulfonylurea.
  • the amounts described herein refer to the sum amount of all the sulfonylureas present in the composition.
  • the sulfonylurea has a particle size (D50) in a range from a lower limit of at least 100 nm, 200 nm, 500 nm, 1 ⁇ m, 2 ⁇ m, or 3 ⁇ m, as a particle size less than this can generate excess heat during milling and possibly degrade the sulfonylurea.
  • the sulfonylurea has a particle size (D50) in a range from any of the lower limits above to an upper limit of 30 ⁇ m, 15 ⁇ m, 10 ⁇ m,
  • any of the preferred lower limits for the sulfonylurea particle size can be combined with any of the preferred upper limits to define further suitable particle size ranges for the present invention.
  • Exemplary ranges for the particle size (D50) of the sulfonylurea include 0.1-30 ⁇ m, 0.2-15 ⁇ m, 0.5-10 ⁇ m, 0.1-0.5 ⁇ m, 0.2-1 ⁇ m, 0.5-3 ⁇ m, 1-15 ⁇ m, 1-10 ⁇ m, 1-7 ⁇ m, 2-15 ⁇ m, 2-10 ⁇ m, 2-7 ⁇ m, 3-15 ⁇ m, 3-10 ⁇ m, and 3-7 ⁇ m.
  • D50 refers to the volume median particle size and can be determined by laser light scattering using the method described in CIPAC MT187.
  • the liquid composition of the invention may comprise more than one sulfonylurea herbicide compound.
  • the liquid composition may comprise any combination of sulfonylureas as disclosed herein.
  • the liquid composition may comprise tribenuron-methyl and any other sulfonylurea described herein; the liquid composition may comprise metsulfuron-methyl and any other sulfonylurea described herein; or the liquid composition may comprise nicosulfuron and any other sulfonylurea described herein.
  • composition of the present invention comprises at least one inorganic salt selected from alkali metal silicates.
  • the inorganic salt comprises a metal selected from sodium and potassium.
  • Alkali metal silicates may be typically provided as aqueous solutions/dispersions, but are also available as solids, such as powders. Suitable alkali metal silicates include sodium silicate, potassium silicate, lithium silicate, and combinations thereof. In embodiments the alkali metal silicate is selected from sodium silicate, potassium silicate, and combinations thereof.
  • the inorganic salt is selected from sodium silicates, including wherein the inorganic salt is selected from sodium silicate, sodium metasilicate, sodium orthosilicate, sodium trisilicate, sodium pyrosilicate, hydrates thereof, or mixtures thereof.
  • Notable liquid compositions are those wherein the inorganic salt comprises sodium silicate.
  • Sodium silicate is the common name for materials comprising sodium, oxygen and silicon in various ratios, such as materials comprising the nominal formulae Na 2x SiO 2+x or (Na 2 O) x SiO 2 .
  • sodium silicates include sodium orthosilicate, Na 4 SiO 4 , sodium trisilicate, Na 2 Si 3 O 7 , and sodium pyrosilicate Na 6 Si 2 O 7 .
  • Solid sodium silicate is generally an amorphous powder and typically may be prepared with various ratios of SiO 2 :Na 2 O.
  • Sodium silicate solutions may also be referred to as “waterglass”.
  • Commercially available sodium silicate solutions and powders have a weight ratio of SiO 2 :Na 2 O in the range of about 1.5 to about 3.75. The ratio represents an average of various molecular weight silicate species present in the sodium silicate. Grades with this ratio below 2.85:1 are considered as alkaline. Those with a higher SiO 2 :Na 2 O ratio are described as neutral.
  • Suitable sodium silicate compositions have a weight ratio of SiO 2 :Na 2 O in the range of about 1.5 to about 3.5, about 2 to about 3.2, about 2.1 to about 3.2, or about 2.5 to about 3.2, or about 3.0 to about 3.2; for example, about 2.5, about 2.6, about 2.7, about 2.8, about 2.9, about 3.0, about 3.1, or about 3.2.
  • Sodium silicate solids may comprise various hydrate forms resulting from their crystallization from aqueous solutions.
  • a notable sodium silicate for use in the liquid compositions is sodium metasilicate, preferably anydrous sodium metasilicate.
  • the anhydrous compound can be prepared by fusing silicon dioxide, SiO2, with sodium oxide, Na20, in 1:1 molar ratio.
  • the metasilicate anion is actually polymeric, consisting of comer-shared ⁇ SiO 4 ⁇ tetrahedra, and not a discrete SiO 3 2- ion.
  • there are hydrates with the formula Na 2 SiO 3 ⁇ nH 2 O (where n 5, 6, 8, 9), which contain the discrete, approximately tetrahedral anionSiO 2 (OH) 2 2- with water of hydration.
  • the sodium silicate pentahydrate Na2SiO3-5H20 and the nonahydrate Na 2 SiO 3 ⁇ 9H 2 0 are commercially available.
  • a notable alkali metal silicate for use in the liquid compositions is potassium silicate.
  • compositions may optionally comprise other inorganic salts in addition to the alkali metal silicates.
  • exemplary optional metal salts include those derived from the alkali metals such as lithium, sodium and potassium, the alkaline earth metals such as magnesium and calcium, as well as those derived from other metals such as aluminum.
  • Exemplary optional salts include Na 3 PO 4 , Na 2 CO 3 , AIPO 4 , Mg3(PO 4 ) 2 and Na 2 HPO 4 .
  • Preferred optional salts for the present invention include sodium phosphate, potassium phosphate and sodium carbonate in their various forms. Both the anhydrous and hydrated forms of the optional metal salts can be used but the anhydrous form is preferred to minimize the amount of water introduced into the liquid compositions.
  • sodium phosphate and the term “potassium phosphate” includes the various forms of sodium phosphate and potassium phosphate, respectively, as well as all anhydrous and hydrated forms thereof.
  • “sodium phosphate” includes monosodium phosphate (anhydrous), monosodium phosphate (monohydrate), monosodium phosphate (dihydrate), disodium phosphate (anhydrous), disodium phosphate (dihydrate), disodium phosphate (heptahydrate), disodium phosphate (octahydrate), disodium phosphate (dodecahydrate), trisodium phosphate (anhydrous, hexagonal), trisodium phosphate (anhydrous, cubic), trisodium phosphate (hemihydrate), trisodium phosphate (hexahydrate), trisodium phosphate (octahydrate), trisodium phosphate (dodecahydrate), monosodium diphosphate (
  • sodium silicate salts provide for liquid sulfonylurea compositions with superior chemical stability than many of the other salts mentioned herein, particularly with respect to those sulfonylureas that are more prone to hydrolysis in liquid compositions.
  • tribenuron- methyl was found to have excellent chemical stability in the presence of a sodium silicate, such as sodium metasilicate.
  • the sulfonylurea is one or more selected from tribenuron-methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron-ethyl, chlorsulfuron, amidosulfuron, and triasulfuron. Accordingly, the invention also relates to formulations, as described herein, comprising the above preferred combination of silicate salt and sulfonylurea.
  • the invention also relates to the use of alkali metal silicates to improve chemical stabilization of sulfonylureas such as tribenuron- methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron- ethyl, chlorsulfuron, amidosulfuron, or triasulfuron in all such formulations.
  • sulfonylureas such as tribenuron- methyl, metsulfuron-methyl, nicosulfuron, bensulfuron-methyl, foramsulfuron, pyrazosulfuron- ethyl, chlorsulfuron, amidosulfuron, or triasulfuron in all such formulations.
  • the inorganic salt is preferably included in the liquid composition of the invention in an amount of at least 0.01 weight% based on the total weight of the liquid composition.
  • the inorganic salt is preferably included in the composition in an amount of 30 weight% or less to reduce physical stability problems of the formulation and to reduce interference with the function of any surfactants that are optionally present.
  • the amount of inorganic salt in the liquid compositions comprises an amount in a range from a lower limit of at least 0.03 weight%, 0.05 weight%, 0.1 weight%, 0.2 weight%, 0.5 weight%, 1 weight%, 2 weight% to an upper limit of 25 weight%, 20 weight%, 15 weight%, 10 weight%, 8 weight%, 6 weight%, 5 weight%, 2 weight%, 1 weight%, or 0.7 weight% or less. Any of the preferred lower weight% limits can be combined with any of the preferred upper weight% limits to define further suitable weight% ranges of inorganic salt in the liquid composition.
  • Exemplary amounts of inorganic salt in the liquid composition include 0.01 to 30weight%, 0.1 to 25 weight%, 1 to 20 weight%, 1 to 10 weight%, 0.5 to 10 weight%, 1 to 5 weight%, 0.5 to 5 weight%, 0.1 to 2 weight%, 0.2 to 2 weight%, 0.2 to 1 weight%, and 0.2 to 0.7 weight%.
  • the weight ranges above refer to the total amount of inorganic salt that is present in the liquid compositions.
  • the weight ranges above do not refer to other salts that might be present in the composition such as the salt of a sulfonylurea.
  • the weight ratio of the inorganic salt to sulfonylurea is 0.1 or greater.
  • the weight ratio of the inorganic salt to sulfonylurea is in a range from a lower limit 0.2, 0.3, 0.5, 0.7, or 1 to an upper limit of 5, 4, 3, 2, or 1.
  • the preferred weight ratios refer to the total amount of the alkali metal silicate and any optional inorganic salts described above to the total amount of sulfonylurea compounds in the liquid composition. Any of the preferred lower weight ratio limits can be combined with any of the preferred upper weight ratio limits to define further suitable weight ratio ranges for the present invention.
  • Exemplary ranges for the weight ratio of the inorganic salt to sulfonylurea include 0.1 to 5, 0.2 to 4, 0.3 to 3, 0.3 to 1, 0.5 to 2, 0.7 to 2, 0.1 to 2, 1 to 2 and 1 to 5.
  • the liquid herbicidal composition comprises: a non-aqueous liquid carrier, at least one sulfonylurea herbicide, wherein the total amount of sulfonylurea compounds is
  • the composition 1 to 50 weight% of the composition; and at least one inorganic salt comprising alkali metal silicates, and optionally metal carbonates and/or metal phosphates, wherein the total amount of inorganic salt comprises 0.1 to 20 weight%; such as wherein the weight ratio of inorganic salt to sulfonylurea is in the range of from 0.1 to 5.
  • the at least one inorganic salt comprises alkali metal silicates and optionally metal carbonates and/or metal phosphates.
  • the total amount of sulfonylurea compounds is 0.5 to 20 weight%
  • the total amount of inorganic salt is 1 to 20 weight%
  • the weight ratio of inorganic salt to sulfonylurea is in the range of from 0.1 to 5.
  • the total amount of sulfonylurea compounds is 1 to 20 weight%
  • the total amount of inorganic salt is 1 to 20 weight%
  • the weight ratio of inorganic salt to sulfonylurea is in the range of from 0.5 to 2.5, preferably 0.7 to 2.3.
  • the particle size (D50) of the inorganic salt is a range from a lower limit of at least 100 nm, 200 nm, 500 nm, 1 ⁇ m, 1.5 ⁇ m, 2 ⁇ m, or 3 ⁇ m, to an upper limit of 30 ⁇ m, 15 ⁇ m, 10 ⁇ m, 7 ⁇ m, 5 ⁇ m, 3 ⁇ m, 1 ⁇ m or 500 nm or less. Any of the preferred lower limits for the inorganic salt particle size can be combined with any of the preferred upper limits to define further suitable particle size ranges for the present invention.
  • Exemplary ranges for the particle size (D50) of the sulfonylurea include 0.1-30 ⁇ m, 0.2-15 ⁇ m, 0.5-10 ⁇ m, 0.1-0.5 ⁇ m, 0.2-1 ⁇ m, 0.5-3 ⁇ m, 1-15 ⁇ m, 1-10 ⁇ m, 1-7 ⁇ m, 1-5 ⁇ m, 1.5-5 ⁇ m, 2-15 ⁇ m, 2-10 ⁇ m, 2-7 ⁇ m, 2-5 ⁇ m, and 2-3 ⁇ m.
  • D50 refers to the volume median particle size and can be determined by laser light scattering using the method described in CIPAC MT187.
  • the liquid composition optionally further comprises at least one inorganic salt selected from metal carbonates and metal phosphates that is not calcium carbonate or sodium triphosphate. In other embodiments, the liquid composition does not comprise sodium phosphate, sodium carbonate, calcium carbonate or sodium triphosphate.
  • the amount of alkali metal silicates needed to provide a desired degree of stability depends upon the specific sulfonylurea herbicide(s) and other ingredients in the composition. As shown in Table A, the chemical stability of representative sulfonylureas in an oil dispersion (OD) formulation not containing alkali metal silicates subjected to accelerated heat aging can vary significantly. Tribenuron-methyl is particularly unstable in oil dispersions subjected to accelerated heat aging. The stability of a given sulfonylurea alone may not be the same as that exhibited when combined with another sulfonylurea in the same formulation.
  • the amount of stabilization of an individual sulfonylurea in a combination of two or more sulfonylureas may not be the same as that obtained for other sulfonylurea(s) in the combination (i.e. differentially stablilized).
  • compositions comprising metsulfuron-methyl, thifensulfuron-methyl or halosulfuron- methyl may require only a relatively small amount of alkali metal silicates (e.g., less than 1% of the composition by weight) to reduce the percent relative decomposition to less than 10% during accelerated aging of 2 weeks at 54 °C.
  • alkali metal silicates e.g., less than 1% of the composition by weight
  • Other sulfonylureas, such as tribenuron-methyl, may require larger amounts of alkali metal silicates.
  • the composition of the present invention comprises a non-aqueous liquid carrier.
  • non-aqueous liquid carrier means that one or more liquid carriers other than water (e.g., organic solvents) are used as the liquid carrier in the liquid composition. This does not mean to say that the liquid carrier must necessarily be completely free of water. Trace amounts of water may be present in the components that are used to prepare the non-aqueous liquid carrier. For instance, trace amounts of water may be introduced into the liquid carrier by organic solvents, surfactants or salts that are used to prepare the liquid herbicidal composition.
  • non-aqueous liquid carrier e.g., ODs, DCs, ECs and SLs employ a non-aqueous liquid carrier
  • the term can be taken to mean that the liquid composition comprises water in an amount of 5 weight% or less of the composition, preferably 3 weight% or less, preferably 2.5 weight% or less, more preferably 2 weight%, most preferably 1 weight% or less, or 0.5 weight% or less, or there is no water in the composition.
  • the sulfonylurea is dispersed, suspended or otherwise contained in the non-aqueous liquid carrier.
  • Typical liquid carriers are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
  • the non-aqueous liquid carrier preferably contains one or more aprotic organic solvents as the major constituent of the liquid carrier.
  • the amount of aprotic solvent in the liquid carrier is 50 weight% or more, the ability of the inorganic salt to chemically stabilize the sulfonylurea is greatly improved.
  • the one or more aprotic solvents make up 60 weight% or more, 70 weight% or more, 80 weight% or more and most preferably 90 weight% or more of the liquid carrier.
  • Suitable aprotic organic solvents for use in the present invention include, for example:
  • hydrocarbons which may be unsubstituted or substituted, for example (la) aromatic hydrocarbons, for example mono- or polyalkyl-substituted benzenes, such as toluene, xylenes, mesitylene, ethylbenzene, or mono- or polyalkyl-substituted naphthalenes, such as 1-methylnaphthalene, 2-methylnaphthalene or dimethylnaphthalene, or other benzene-derived aromatic hydrocarbons, such as indane or Tetralin®, or mixtures thereof, (lb) aliphatic hydrocarbons, for example straight-chain or branched aliphatics, for example of the formula C n H2n+2, such as pentane, hexane, octane, 2-methylbutane or 2,2,4-trimethylpentane, or cyclic, optionally alkyl-substituted aliphatics, such as cyclo
  • fatty acid esters for example of natural origin, for example natural oils, such as animal oils or vegetable oils, or of synthetic origin, for example the Edenor® series, for example Edenor® MEPa or Edenor® MESU, or the Agnique® ME series or Agnique® AE series (Cognis), the Salim® ME series (Salim), the Radia® series, for example Radia® 30167 (ICI), the Prilube® series, for example Prilube® 1530 (Petrofina), the Stepan® C series (Stepan) or the Witconol® 23 series (Witco).
  • the fatty acid esters are preferably esters of C 10 -C 22 fatty acids, preferably C 12 -C 20 fatty acids.
  • the C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 - C22 fatty acids, notably those having an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid, and particularly C 18 fatty acids, such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • fatty acid esters such as C 10 -C 22 fatty acid esters include glycerol and glycol esters of fatty acids such as C 10 -C 22 fatty acids, or transesterification products thereof, for example fatty acid alkyl esters such as C 10 -C 22 fatty acid C 1 -C 20 alkyl esters, which can be obtained, for example, by transesterification of the abovementioned glycerol or glycol fatty acid esters such as C 10 -C 22 fatty acid esters with C 1 -C 20 alkanols (for example methanol, ethanol, propanol or butanol).
  • fatty acid esters such as C 10 -C 22 fatty acid esters include glycerol and glycol esters of fatty acids such as C 10 -C 22 fatty acids, or transesterification products thereof, for example fatty acid alkyl esters such as C 10 -C 22 fatty acid C 1 -C 20 alkyl esters, which can
  • Preferred fatty acid alkyl esters such as C 10 -C 22 fatty acid C 1 -C 20 alkyl esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters.
  • Preferred glycol and glycerol fatty acid esters such as C 10 -C 22 fatty acid esters are the uniform or mixed glycol esters and glycerol esters of C 10 -C 22 fatty acids, notably such fatty acids having an even number of carbon atoms, for example crude acid, lauric acid, palmitic acid and particularly C 18 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • animal oils and vegetable oils are generally known and commercially available.
  • the term “animal oils” is to be understood as meaning oils of animal origin such as whale oil, cod-liver oil, musk oil or mink oil
  • vegetable oils is to be understood as meaning oils of oleaginous plant species, such as soybean oil, rapeseed oil, com oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil, walnut oil, arachis (peanut) oil, tung oil, sesame oil, olive oil or castor oil, in particular soybean oil or rapeseed oil, where the vegetable oils also include their transesterification products, for example alkyl esters, such as soybean oil methyl ester or rapeseed oil ethyl ester.
  • Vegetable oils are preferred and may comprise esters of C 10 -C 22 fatty acid esters as described above.
  • the vegetable oils can be contained in the mixtures for example in the form of commercially available vegetable oils, in particular rapeseed oils, such as rapeseed oil methyl ester, for example Phytorob® B (Novance, France), Edenor® MESU and the Agnique® ME series (Cognis, Germany) the Radia® series (ICI), the Prilube® series (Petrofina), or biodiesel or in the form of commercially available plant-oil-containing formulation additives, in particular those based on rapeseed oils, such as rapeseed oil methyl esters, for example Hasten® (Victoria Chemical Company, Australia), Actirob® B (Novance, France), Rako-Binol® (Bayer AG, Germany), Renol® (Stefes, Germany) or Mero® (Stefes, Germany).
  • rapeseed oils
  • Examples of synthetic acid esters are, for example, those derived from fatty acids having an odd number of carbon atoms, such as C 11 -C 21 -fatty acid esters.
  • Preferred organic liquid carriers arc hydrocarbons, in particular aromatic hydrocarbons and/or aliphatic hydrocarbons and fatty acid esters, such as vegetable oils, such as triglycerides of fatty acids having 10 to 22 carbon atoms, which may be saturated or else unsaturated, straight- chain or branched and which may or may not carry further functional groups, such as com oil, rapeseed oil, sunflower oil, cottonseed oil, linseed oil, soybean oil, coconut oil, palm oil, thistle oil or castor oil, and their trans-esterification products, such as fatty acid alkyl esters, and mixtures thereof.
  • vegetable oils such as triglycerides of fatty acids having 10 to 22 carbon atoms, which may be saturated or else unsaturated, straight- chain or branched and which may or may not carry further functional groups, such as com oil, rapeseed oil, sunflower oil, cottonseed oil, linseed oil, soybean oil, coconut oil, palm oil, thistle oil or
  • Preferred liquid carriers for use in the present invention include: linear or branched C 6 -C 30 paraffin oils, for example hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, their mixtures, or mixtures thereof with higher boiling homologs, such as hepta-, octa-, nona-decane, eicosane, heneicosane, docosane, tricosane, tetracosane, pentacosane, and the branched chain isomers thereof; aromatic or cycloaliphatic liquid carriers, which may be unsubstituted or substituted, C 7 -C 18 hydrocarbon compounds such as mono- or polyalkyl-substituted benzenes, or mono- or polyalkyl-substituted
  • Esters which can be used in the composition of the invention are thus, for example, benzyl acetate, caproic acid ethyl ester, isobomyl acetate, pelargonic acid ethyl ester, benzoic acid methyl or ethyl ester, salicylic acid methyl, propyl, or butyl ester, diesters of phthalic acid with saturated aliphatic or alicyclic C 1 -C 12 alcohols, such as phthalic acid dimethyl ester, dibutyl ester, diisooctyl ester; liquid amides of C 1 -C 3 amines, alkylamines or alkanolamines with C 6 -C 18 carboxylic acids; or mixtures thereof.
  • the liquid carrier of the single liquid-phase composition of the present invention comprises one or more fatty acid esters of C 1 -C 4 alkanols.
  • the C 1 -C 4 alkanol-derived portions of the fatty acid esters can be unbranched (i.e. straight- chain) or branched, but are typically unbranched.
  • the fatty acid esters are fatty acids esterified with C 1 - C 2 alkanols and more preferably C 1 alkanol (i.e. methanol).
  • the fatty acid alkanol esters in a composition of the present invention can be derived from a mixture of alcohols (e.g., methanol and ethanol).
  • the fatty acid portions of the fatty acid esters consist of a carboxylate moiety bound to a hydrocarbon chain, which can be unbranched or branched, but is typically unbranched in natural sources.
  • the hydrocarbon chain can be saturated or unsaturated; typically the hydrocarbon chain is saturated (i.e. alkyl) or contains 1 or 2 carbon-carbon double bonds (i.e. alkenyl).
  • Fatty acid esters formed from fatty acids containing an odd number of carbon atoms i.e. even number of carbon atoms in the hydrocarbon chain
  • fatty acids obtained from natural sources typically contain an even number of carbon atoms, and therefore esters of fatty acids containing an even number of carbon atoms are preferred for reason of commercial availability and cost.
  • Fatty acid compositions obtained from natural sources typically consist of fatty acids having a range of chain lengths and different degrees of unsaturation.
  • Fatty acid ester compositions derived from such fatty acid mixtures are generally useful in the compositions of the present invention without need to first separate the fatty acid esters.
  • Fatty acids contain at least 4 carbon atoms and are limited to about 22 carbon atoms from natural sources. Although esters of lower fatty acids (e.g., containing as few a 4 carbon atoms) are useful for the present compositions, esters of fatty acids having at least 8, more preferably at least 10, carbon atoms are preferred because of favorable physical properties (e.g., low volatility). Esters of lower fatty acids can be mixed with esters of higher fatty acids to decrease polarity, water solubility and volatility. As fatty acids obtained from natural sources typically contain 8 to 22 carbon atoms, more typically 10 to 22 carbon atoms, esters of these fatty acids are preferred for reason of commercial availability and cost.
  • the C 10 -C 22 fatty acid esters with an even number of carbon atoms are, for example, erucic acid, lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid and linolenic acid.
  • the one or more fatty esters in the compositions of the present invention comprise at least about 80%, more preferably at least 90%, by weight of esters of fatty acids containing 8 to 22 carbon atoms, preferably 12 to 20 carbon atoms and more preferably 16 to 18 carbon atoms.
  • Fatty acid compositions obtained from natural sources typically consist of fatty acids having a range of chain lengths and different degrees of unsaturation.
  • Fatty acid ester compositions derived from such fatty acid mixtures can be useful in the compositions of the present invention without need to first separate the fatty acid esters.
  • Suitable fatty acid ester compositions obtained from plants include seed and fruit oils of sunflower, rapeseed, olive, com, soybean, cotton and linseed.
  • the one or more fatty acid esters comprise fatty acid methyl esters derived from seed oils of sunflower, soybean, cotton or linseed.
  • the one or more fatty acid esters comprise fatty acid methyl esters derived from soybean oil (also known as methylated soybean oil or methyl soyate).
  • Fatty acid esters of alkanols and methods for their preparation are well known in the art.
  • “biodiesel” typically comprises fatty acid esters of ethanol or more commonly methanol.
  • Two principal routes used to prepare fatty acid alkanol esters are transesterification starting with another fatty acid ester (often a naturally occurring ester with glycerol) and direct esterification starting with the fatty acid.
  • transesterification can be accomplished by contacting a fatty acid with an alkanol in the presence of a strong acid catalyst such as sulfuric acid.
  • Transesterification can be accomplished by contacting a starting fatty acid ester with the alcohol in the presence of a strong acid catalyst such as sulfuric acid but more commonly a strong base such as sodium hydroxide.
  • Alkylated seed oils are the transesterification products of seed oils with an alkanol.
  • methylated soybean oil also known as methyl soyate
  • Methyl soyate thus comprises methyl esters of fatty acids in the approximate molar ratio that the fatty acids occur esterified with glycerol in soybean seed oil.
  • Alkylated seed oils such as methyl soyate can be distilled or otherwise processed to modify the proportion of methyl fatty acid esters.
  • compositions of the present invention are generally in the form of oil dispersions or non-aqueous suspension concentrates.
  • liquid diluents include, for example, aprotic polar solvents, such as ethers, esters of C 1 -C 9 -alkanoic acids which may be mono-, di- or polyfunctional, such as their mono-, di- or triesters, for example with C 1 -C 18 -alkyl alcohols, ketones with a low tendency to tautomerize, such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as hexyl acetate, heptyl acetate and octyl acetate, phosphoric acid esters, amides, nitriles or sulfones, for example tris-2-ethylhexyl phosphate, diisobutyl adipate, Rhodiasolv® RPDE
  • aprotic polar solvents such as ethers, esters of C 1 -C 9 -al
  • Protic solvents include for example, ethylene glycol, polypropylene glycol, glycerin, alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol, amines and carboxylic acids.
  • alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol, amines and carboxylic acids.
  • polar solvents are best avoided as liquid carriers.
  • the total amount of protic organic solvent such as alcohols is preferably kept to 20 weight% or less based on the weight of the liquid composition.
  • the total amount of protic organic solvent is 15 weight% or less, 10 weight% or less, 5 weight% or less, 2 weight% or less, or 1 weight% or less of the composition.
  • the amounts described herein refer to the sum amount of all the protic solvents present in the composition.
  • the liquid carrier of the present compositions does not include substantial amounts of liquid diluents other than the hydrocarbons and/or fatty acid esters of C 1 -C 4 alkanols described above.
  • the non-aqueous liquid carrier is present in an amount such that it can act as a liquid carrier for the other components that are present in the composition.
  • the non-aqueous liquid carrier comprises an organic solvent in an amount of at least 5 weight% based on the weight of the composition.
  • a low amount of liquid carrier is possible when other components in the composition are also liquids (e.g., liquid herbicide and/or liquid emulsifier).
  • the non-aqueous liquid carrier comprises an organic solvent in an amount of 95 weight% or less of the composition.
  • the non-aqueous liquid carrier comprises an organic solvent in an amount in a range from a lower limit of least 10 weight%, 15 weight%, weight%, 25 weight%, 30 weight%, or 40 weight% of the composition to an upper limit of 90 weight%, 85 weight%, 80 weight%, 75 weight%, or 60 weight% or less of the composition.
  • Any of the disclosed lower weight% limits can be combined with any of the disclosed upper weight% limits to define further suitable weight% ranges of the amount of the organic solvent in the non-aqueous liquid carrier in compositions of this invention.
  • Exemplary ranges of the amount of the organic solvent in the composition include 5 to 95 weight%, 10 to 90 weight%, 20 to 80 weight%, 30 to 60 weight%, 40 to 60 weight%, 10 to 75 weight% and 20 to 60 weight%.
  • the amounts described herein refer to the sum amount of all the organic solvents present in the composition.
  • compositions and formulations comprising a sulfonylurea described herein can be combined with any other suitable additional or secondary agricultural active ingredients, or other suitable additional agricultural compositions such as liquid fertilizers, insecticides, herbicides, fungicides, nematicides, safeners and plant growth regulators.
  • suitable additional or secondary agricultural active ingredients such as liquid fertilizers, insecticides, herbicides, fungicides, nematicides, safeners and plant growth regulators.
  • suitable additional agricultural compositions such as liquid fertilizers, insecticides, herbicides, fungicides, nematicides, safeners and plant growth regulators.
  • suitable additional agricultural compositions such as liquid fertilizers, insecticides, herbicides, fungicides, nematicides, safeners and plant growth regulators.
  • the compositions, formulations, and methods comprising a sulfonylurea can be applied simultaneously or sequentially with the additional or secondary agricultural active ingredients.
  • a composition comprising a sulfonylurea can be combined with the additional agricultural active ingredient(s) in a single formulation, such as in a ready-to-use formulation that may be typically mixed with water to a prepare a final spray mixture for application.
  • a composition or formulation comprising a sulfonylurea can be combined with a separate composition comprising the additional agricultural active ingredient(s) in the form of a combination package, such as a twin pack, for mixing prior to application.
  • the compositions and formulations comprising a sulfonylurea of the present disclosure can be combined with the additional agricultural active ingredient(s) in the form of a tank mix.
  • the active compounds can be supplied (either separately or pre-mixed) in any appropriate formulation type, for example an emulsifiable concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), a water in oil emulsion (EO), an oil in water emulsion (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a dispersible concentrate (DC), a wettable powder (WP) or any other technically feasible formulation in combination with agriculturally acceptable adjuvants.
  • EC emulsifiable concentrate
  • SC suspension concentrate
  • SE suspo-emulsion
  • CS capsule suspension
  • WG water dispersible
  • liquid fertilizer refers to a fertilizer in a fluid or liquid form containing various ratios of nitrogen, phosphorous and potassium (for example, but not limited to, 10% nitrogen, 34% phosphorous and 0% potassium) and micronutrients, commonly known as starter fertilizers that are high in phosphorus and promote rapid and vigorous root growth.
  • Liquid fertilizers are commonly aqueous- based. As used herein, the term “aqueous- based” indicates that the predominant solvent or vehicle is water.
  • compositions described herein can be mixed with a liquid fertilizer to create a concentrated aqueous emulsion (EW) formulation, which may be further diluted with water, in a tank mix and then be applied to target crops or weeds.
  • EW concentrated aqueous emulsion
  • compositions, formulations, and methods of the invention can be applied simultaneously with, or sequentially with, other suitable additional or secondary agricultural active ingredients, or other suitable additional agricultural compositions such as insecticides, herbicides, fungicides, nematicides, safeners and plant growth regulators.
  • suitable additional insecticides, herbicides, fungicides, nematicides, safeners and plant growth regulators can include the following:
  • the liquid compositions of the present invention can comprise in addition to sulfonylurea herbicides one or more other biologically active agents.
  • the liquid compositions may comprise up to about 40% by weight of one or more other biologically active agents.
  • Other biologically active agents may include herbicidal compounds other than sulfonylureas and may also include plant growth regulants, herbicide safeners, insecticides, insect antifeedants, miticides, nematocides, bactericides and fungicides, including both chemical and biological agents.
  • additional non-sulfonylurea compounds may be liquids, waxy solids or powders and may be dissolved, dispersed, suspended or otherwise contained in the composition.
  • the additional biologically active agent is not particularly limited and can be any compound known in the art.
  • the compound may be selected from the herbicidal compounds listed in the 16th Edition of “The Pesticide Manual” (ISBN-10: 190139686X) and the literature cited therein.
  • the other active biologically active agents are herbicides and/or herbicide safeners.
  • the non-sulfonylurea herbicidal compounds may include compounds that inhibit acetolactate synthase, but also includes compounds that are herbicidal by other modes of action.
  • compositions where the weight ratio of other biologically active agents to sulfonylurea herbicides is between about 1:100 and about 100:1.
  • This invention also includes a herbicidal mixture comprising (a) a compound selected from sulfonylurea herbicides, N-oxides, and salts thereof, and (b) at least one additional herbicidal active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors other than sulfonylureas, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturas
  • HPPD 4-hydroxyphenyl-pyruvate dioxygenase
  • HHT solenesyltransererase
  • b14 cellulose biosynthesis inhibitors
  • other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts of compounds of (b1) through (b16).
  • Photosystem II inhibitors are chemical compounds that bind to the D-1 protein at the QB-binding niche and thus block electron transport from Q A to Q B in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction.
  • the QB-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil
  • binding site B binds the phenylureas such as diuron
  • binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn,
  • AHAS inhibitors are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth.
  • AHAS acetohydroxy acid synthase
  • ALS acetolactate synthase
  • non-sulfonylurea AHAS inhibitors that can be combined with the sulfonylureas described herein include bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, diclosulam, florasulam, flucarbazone-sodium, flumetsulam, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, metosulam, penoxsulam, propoxycarbazone-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, thiencarbazone and triafamone (N-[2-[(4,6- dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,l-difluoro-N- methylmethanesul
  • ACCase inhibitors are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl Co A carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back.
  • ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.
  • auxin is a plant hormone that regulates growth in many plant tissues.
  • auxin mimics are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species.
  • auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D and esters and salts thereof, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2- pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-
  • EPSP synthase inhibitors are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine.
  • EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points.
  • Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
  • Photosystem I electron diverters are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles “leak”, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.
  • PPO inhibitors are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out.
  • PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyrafluorfen-
  • GS inhibitors are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes.
  • the GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-
  • VLCFA elongase inhibitors are herbicides having a wide variety of chemical structures, which inhibit the elongase.
  • Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs.
  • very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains.
  • Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4- ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)-N,N-diethyl-2-(l-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxy
  • auxin transport inhibitors are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein.
  • auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1 -naphthy l)phthalamic acid and
  • PDS inhibitors are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step.
  • PDS inhibitors include beflubutamid, S-beflubutamid, beflubutamid-M, diflufenican, fluridone, flurochloridone, flurtamone, norflurzon and picolinafen.
  • HPPD inhibitors are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.
  • HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3- pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4- methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrion
  • HST inhibitors disrupt a plant’s ability to convert homogentisate to 2-methyl-6-solanyl- 1 ,4-benzoquinone, thereby disrupting carotenoid biosynthesis.
  • HST inhibitors include haloxydine, pyriclor, 3-(2-chloro-3 ,6-difluorophenyl)-4-hydroxy- 1 - methyl- 1 ,5-naphthyridin-2( 1H -one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8- hydroxypyrido[2,3-b]pyrazin-6(5H)-one and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6- dimethyl-3(2H)-pyridazinone.
  • HST inhibitors also include compounds of Formulae A and B.
  • R d1 is H, Cl or CF 3 ;
  • R d2 is H, Cl or Br;
  • R d3 is H or Cl;
  • R d4 is H, Cl or CF 3 ;
  • R d5 is CH 3 , CH 2 CH 3 or CH 2 CHF 2 ;
  • R el is H, F, Cl, CH 3 or CH 2 CH 3 ;
  • R e2 is H or CF 3 ;
  • R e3 is H, CH 3 or CH 2 CH 3 ;
  • R e4 is H, F or Br,
  • R e5 is Cl, CH 3 ,
  • R e6 is H, CH 3 , CH 2 CHF 2 or C ⁇ CH
  • a e8 is N or CH.
  • Cellulose biosynthesis inhibitors inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied preemergence or early postemergence on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N 2 -[(1R,2S)- 2,3-dihydro-2, 6-dimethyl- 1H-inden-1-yl]-6-(l- fluoroethyl)-1, 3, 5-triazine-2, 4-diamine), isoxaben and triaziflam.
  • “Other herbicides” include herbicides that act through a variety of different modes of action such as mitotic disrupters (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.
  • Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (b1) through (b14) or act through a combination of modes of action listed above.
  • herbicides examples include aclonifen, asulam, amitrole, bixlozone, bromobutide, cinmethylin, clomazone, cumyluron, cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4- pyridazinyl 4-morpholinecarboxylate), daimuron, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl- 3-isoxazolidinone, difenzoquat, etobenzanid, fiuometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4- difluorophenyl)- 1 ,5-dihydro-N-(1-methylethyl)-5-oxo-4H- 1 ,2,2,
  • herbicides (b15) also include a compound of Formula (b15A),
  • herbicides (b15) also include a compound of Formula (b15B) wherein R 1 is CH3, R 2 is Me, R 4 is OCHF2, G is H, and n is 0; R 1 is CH3, R 2 is Me, R 3 is 5-F, R 4 is Cl, G is H, and n is 1; R 1 is CH3, R 2 is Cl, R 4 is Me, G is H, and n is 0; R 1 is CH 3 , R 2 is Me, R 4 is Cl, G is H, and n is 0; R 1 is CH 3 , R 2 is Me, R 3 is 5-Me, R 4 is OCHF 2 , G is H, and n is 1; R 1 is CH 3 , R 2 is Me, R 3 is 5-Br, R 4 is OCHF 2 , G is H, and n is 1; R 1 is CH3, R 2 is Me, R 3 is 5-Cl, R 4 is Cl, G is H, and n is 1; or R 1 is CH 3 , R 2 is CH
  • herbicides (b15) also include a compound of Formula (b15C) wherein R 1 is CH3, R 2 is Cl, and G is H; or
  • R 1 is CH 3
  • R 2 is Cl
  • G is C(0)Me.
  • herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditman Fries, Phytophthora palmivora (Bull.) Bull, and Puccinia thlaspeos Schub.
  • bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditman Fries, Phytophthora palmivora (Bull.) Bull, and Puccinia thlaspeos Schub.
  • Herbicide safeners are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation.
  • the liquid composition of the present invention may comprise one or more safeners that may be dissolved, dispersed, suspended or otherwise contained in the composition. Suitable safeners include those listed in the “The Pesticide Manual” (ISBN- 10: 190139686X), as well as those listed in paragraphs [0113] to [0129] of US2006/0276337 Al.
  • Exemplary safeners include: (1) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type such as ethyl 1-(2,4-dichlorophenyl)-5-(ethoxy-carbonyl)-5-methyl-2-pyrazoline-3- carboxylate and related compounds, as described in W091/07874; (2) derivatives of dichlorophenylpyrazolecarboxylic acid, preferably compounds such as ethyl 1-(2,4- dichlorophenyl)-5-methylpyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5 - isopropylpyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(l,l-dimethylethyl)pyrazole-3- carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate and related compounds,
  • active compounds of the oxyimino compound type such as, for example, “oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino- (phenyl)acetonitrile), “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone 0-(l,3- dioxolan-2-ylmethyl) oxime, and “cyometrinil” or “CGA43089” ((Z)-cyanomethoxyimino- (phenyl)acetonitrile); (12) active compounds of the thiazolecarboxylic ester type, which are known as seed dressings, such as, for example, “flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3- thiazole-5-carboxy
  • Preferred herbicide safeners include but are not limited to benoxacor, BCS, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone ((4-methoxy-3- methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N-(aminocarbonyl)-2- fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfony
  • More preferred herbicide safeners include benoxacor, BCS, cloquintocet-mexyl, cyometrinil, cyprosulf amide, dichlormid, dicyclonon, 2-(dichloromethyl)-2-methyl- 1 ,3-dioxolane
  • MG 191 dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr, mefenpyr-ethyl, methoxyphenone, mephenate, naphthalic anhydride and oxabetrinil.
  • Insecticidal compounds that may be used in combination with the sulfonylureas in this invention include:
  • C1 carbamates such as aldicarb, alanycarb, benfuracarb, carbary 1, carbofuran, carbosulfan, methiocarb, methomyl, oxamyl, pirimicarb, propoxur and thiodicarb;
  • organophosphates such as acephate, azinphos-ethyl, azinphos-methyl, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidaphos, methidathion, mevinphos, monocrotophos, oxymethoate, oxydemeton-methyl, para- thion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, pirimiphos-methyl, quinalphos, terbufos, tetrachlor- vinphos, triazophos and trichlorfon;
  • fiproles such as ethiprole, fipronil, pyrafluprole and pyriprole;
  • neonicotinoids such as acetamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam;
  • spinosyns such as spinosad and spinetoram
  • chloride channel activators from the class of mectins such as abamectin, emamectin benzoate, ivermectin, lepimectin and milbemectin;
  • juvenile hormone mimics such as hydroprene, kinoprene, methoprene, fenoxycarb and pyriproxyfen;
  • selective homopteran feeding blockers such as pymetrozine, flonicamid and pyrifluquinazon;
  • mite growth inhibitors such as clofentezine, hexythiazox and etoxazole;
  • C11) inhibitors of mitochondrial ATP synthase such as diafenthiuron, fenbutatin oxide and propargite; uncouplers of oxidative phosphorylation such as chlorfenapyr, C12) nicotinic acetylcholine receptor channel blockers such as bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium; C13) inhibitors of the chitin biosynthesis type 0 from the benzoylurea class such as bistrifluron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, no- valuron and teflubenzuron; C14) inhibitors of the chitin biosynthesis type 1 such as buprofezin; C15) molting disruptors such as cyromazine;
  • ecdyson receptor agonists such as methoxyfenozide, tebufenozide, halofenozide and chromafenozide; C17) octopamin receptor agonists such as amitraz;
  • C22) compounds of unknown or uncertain mode of action such as azadirachtin, amidoflumet, bifenazate, fluensulfone, piperonyl butoxide, pyridalyl and sulfoxaflor.
  • C23) sodium channel modulators from the class of pyrethroids such as acrinathrin, allethrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta- cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, tau-fluvalinate, permethrin, silafluofen and tralomethrin.
  • acrinathrin such as acrinathrin, allethrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta- cyperme
  • Fungicidal compounds that may be used in combination with the sulfonylureas in this invention include: D1) azoles such as bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thia
  • D2 strobilurins such as azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate and methyl 2-(ortho- (2,5-dimethylphenyloxymethylene)- phenyl)-3-methoxyacrylate, 2-(2-(6-(3-chloro-2-methyl- phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl-
  • carboxamides such as carboxin, benalaxyl, benalaxyl-M, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, isopyrazam, thifluzamide, tiadinil, 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3- methoxyphenyl)ethyl)-2-methanesulfonyl-amino-3-methylbutyramide, N-
  • heterocyclic compounds such as fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, 5-chloro-7-(4-methyl-piperidin-
  • D5) carbamates such as mancozeb, maneb, metam, methasulphocarb, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, benthiavalicarb, propamocarb, propamocarb hydrochloride, 4-fluorophenyl N-( 1 -( 1 -(4-cyanophenyl)-ethanesulfonyl)but-2- yl)carbamate, methyl 3-(4-chloro-phenyl)-3-(2-isopropoxycarbonylamino-3-methyl- butyrylamino)propanoate;
  • D6 other fungicides such as guanidine, dodine, dodine free base, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane, organometallic compounds: fentin salts, organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl, organochlorine compounds: dichlofluanid, flusulf amide, hexachloro- benzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid, others: cyflufenamid, cym
  • compositions and methods of the invention wherein the non-sulfonylurea herbicidal compound is selected from acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, beflubutamid, S-beflubutamid (beflubutamid-M), benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos,
  • Notable non-sulfonylurea herbicidal compounds include 2,4-D and salts and esters thereof, acetochlor, aminopyralid, atrazine, bentazone, benzobicyclon, bromobutide, bromoxynil, butachlor, carfentrazone ethyl, clodinafop, clomeprop, clopyralid, cyprosulfamide, daimuron, dicamba, diflufenican, diflupenzopyr, dimethametryn, fenoxaprop-P-ethyl, fentrazamide, florasulam, flumetsulam, flumioxazin, fluroxypyr or an ester thereof, glyphosphate, glyphosate- ammonium, imazapyr, imazethapyr, indanofan, isoxadifen-ethyl, MCPA, MCPB, mecoprop-P, mefenace
  • non-sulfonylurea herbicidal compounds include 2,4-D and salts and esters thereof, bromoxynil, carfentrazone ethyl, clodinafop, clopyralid, dicamba, florasulam, fluroxypyr or an ester thereof, glyphosphate, mecoprop-P, MCPA, MCPB, quinclorac, and esters thereof.
  • the additional non-sulfonylurea herbicidal compound when present, is preferably included in the liquid composition of the invention in an amount of at least 0.1 weight%.
  • the non- sulfonylurea herbicidal compound is preferably included in the composition an amount of 95 weight% or less. A large amount of non-sulfonylurea herbicidal compound is possible when the non-sulfonylurea herbicidal compound is itself a liquid.
  • the non-sulfonylurea herbicidal compound comprises an amount of the liquid formulation in a range from a lower limit of at least 0.2 weight%, 0.5 weight%, 0.7 weight%, 1 weight%, 2 weight%, 5 weight%, 10 weight%, 15 weight%, 20 weight% or 25 weight% to an upper limit of 60 weight%, 50 weight%, 40 weight%, 35 weight%, 30 weight% or 25 weight%.
  • a lower limit of at least 0.2 weight%, 0.5 weight%, 0.7 weight%, 1 weight%, 2 weight%, 5 weight%, 10 weight%, 15 weight%, 20 weight% or 25 weight% to an upper limit of 60 weight%, 50 weight%, 40 weight%, 35 weight%, 30 weight% or 25 weight%.
  • Exemplary ranges of the amount of non-sulfonylurea herbicidal compound in the liquid composition include 0.1 to 95 weight%, 1 to 60 weight%, 2 to 50 weight%, 5 to 40 weight%, 10 to 30 weight%, 15 to 25 weight%, 25 to 35 weight% and 10 to 50 weight%.
  • the weight% amounts that are described herein refer to the weight of the salt or derivative.
  • the amounts described herein refer to the sum amount of all the non-sulfonylurea herbicidal compounds present in the composition.
  • one or more of the non-sulfonylurea herbicidal compounds may be partially or wholly encapsulated (e.g., microcapsules) such as is described in W02008/061721.
  • the weight% amounts that are described herein refer to the weight of the non- sulfonylurea herbicidal compounds without the encapsulating material.
  • the liquid composition of the invention may comprise any of the sulfonylureas described herein with any of the non-sulfonylurea herbicidal compounds described herein.
  • the liquid composition may comprise tribenuron-methyl and any of the other non-sulfonylurea herbicidal compounds described herein.
  • Exemplary combinations with tribenuron-methyl include tribenuron-methyl and 2,4-D (including esters or amine or choline salts); tribenuron-methyl and MCPA (e.g., as ester or amine); tribenuron-methyl and bromoxynil; tribenuron-methyl and glyphosate; tribenuron-methyl and fluroxypyr, tribenuron-methyl and dicamba (e.g., as the sodium salt or diglycolamine salt or ester); tribenuron-methyl and mecoprop- P; tribenuron-methyl and MCPB; tribenuron-methyl, fluroxypyr and clopyralid; tribenuron-methyl and carfentrazone ethyl; tribenuron-methyl and clopyralid (e.g., as MEA salt); tribenuron-methyl and
  • the liquid composition may comprise nicosulfuron and any of the other non-sulfonylurea herbicidal compounds described herein.
  • nicosulfuron include: nicosulfuron and dicamba (optionally as the sodium salt or ester); nicosulfuron and atrazine; nicosulfuron and flumetsulam; nicosulfuron and clopyralid (optionally as the potassium salt or ester); nicosulfuron and diflupenzopyr (optionally as the sodium salt or ester); nicosulfuron and metolachlor, nicosulfuron and terbuthylazine; nicosulfuron and mesotrione; and nicosulfuron and bentazone.
  • the liquid composition may comprise metsulfuron-methyl and any of the other non- sulfonylurea herbicidal compounds described herein.
  • Exemplary combinations with metsulfuron- methyl include metsulfuron-methyl and acetochlor; metsulfuron-methyl and carfentrazone ethyl; metsulfuron-methyl and imazapyr; metsulfuron-methyl and aminopyralid; metsulfuron-methyl and fluroxypyr, metsulfuron-methyl and mecoprop-p; metsulfuron-methyl and picloram; metsulfuron-methyl and pyraflufen ethyl; metsulfuron-methyl and propanil; metsulfuron-methyl and glyphosate-ammonium; metsulfuron-methyl and dicamba (optionally as the sodium, dimethylammonium or diglycolamine salt or as an ester); metsulfuron-methyl and 2,4-D (optionally as the dimethylam
  • exemplary combinations of sulfonylureas and non-sulfonylureas for use in the present invention include bensulfuron-methyl and acetochlor, bensulfuron-methyl and indanofan; bensulfuron-methyl and clomeprop; bensulfuron-methyl and pretilachlor, bensulfuron-methyl and fentrazamide; bensulfuron-methyl and thenylchlor; bensulfuron-methyl and pentoxazone; bensulfuron-methyl and pyriminobac-methyl; bensulfuron-methyl and bromobutide; bensulfuron- methyl, pentoxazone, pyriminobac-methyl, and bromobutide; bensulfuron-methyl and butachlor, bensulfuron-methyl and daimuron; bensulfuron-methyl and mefenacet; bensulfuron-methyl, daimur
  • the liquid composition of the invention may comprise any of the sulfonylureas described herein with any suitable safener described herein.
  • exemplary combinations of sulfonylurea and safener include: iodosulfuron-methyl (optionally as the sodium salt) and mefenpyr-diethyl; mesosulfuron (and/or as the methyl ester) and mefenpyr-di-ethyl; mesosulfuron (and/or as the methyl ester) and propoxycarbazone (e.g., sodium salt) and mefenpyr-di-ethyl.
  • compositions of the present invention can contain one or more additional formulating ingredients in a total amount by weight of 0 to about 50%.
  • the composition of the invention may comprise one or more additional co-formulants such as surfactants (e.g., emulsifiers and/or dispersants), thickeners and thixotropic agents, wetting agents, anti-drift agents, adhesives, penetrants, preservatives, antifreeze agents, antioxidants, solubilizers, fillers, carriers, colorants, antifoams, fertilizers, evaporation inhibitors and agents which modify pH and viscosity.
  • the liquid composition comprises at least one co-formulant that is an adjuvant, such as one of those listed in the Compendium of Herbicide Adjuvants, 12th Edition, Southern Illinois University, 2014, or any earlier edition thereof.
  • adjuvants include, but are not limited to, paraffin oil, horticultural spray oils (e.g., summer oil), methylated rape seed oil, methylated soybean oil, highly refined vegetable oil and the like, polyol fatty acid esters, polyethoxylated esters, ethoxylated alcohols, alkyl polysaccharides and blends, amine ethoxylates, sorbitan fatty acid ester ethoxylates, polyethylene glycol esters, alkylpolyglucosides and their derivatives (e.g., esters), organosilicone based surfactants, ethylene vinyl acetate terpolymers, ethoxylated alkyl aryl phosphate esters and the like.
  • paraffin oil e.g., summer oil
  • methylated rape seed oil methylated soybean oil
  • highly refined vegetable oil and the like polyol fatty acid esters
  • polyethoxylated esters ethoxylated alcohols
  • the liquid composition of the invention includes one or more surfactants, for example, to enable the forming of an emulsion if the compositions are to be diluted with water.
  • surfactants can be cationic, anionic or non-ionic, but are preferably anionic or non-ionic.
  • the properties of these surfactants include dispersants and wetting agents.
  • the surfactants can be nonionic or ionic (e.g., anionic) and can include polymeric moieties such as polyoxyethylation.
  • Typical surfactants are described in McCutcheon ’s Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964.
  • surfactants include polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, glycerol esters, polyoxy- ethylene/polyoxypropylene block copolymers, and alkylpolyglycosides where the number of glucose units, referred to as degree of polymerization (D.P.), can range from 1 to 3 and the alkyl units can range from C 6 to C 14 (see Pure and Applied Chemistry 72, 1255-1264).
  • degree of polymerization D.
  • Preferred nonionic surfactants for use in this invention include: polyalkoxylated, preferably polyethoxylated, saturated and unsaturated aliphatic alcohols having 8 to 24 carbon atoms in the alkyl radical, which is derived from the corresponding fatty acids or from petrochemical products, and having 1 to 100, preferably 2 to 50, ethylene oxide units (EO), it being possible for the free hydroxyl group to be alkoxylated, which are commercially available, for example, as Genapol® X and Genapol® O series (Clariant), Crovol® M series (Croda) or as Lutensol® series (BASF); polyalkoxylated, preferably polyethoxylated, arylalkylphenols, such as, for example, 2,4,6-tris(l- phenylethyl)phenol (tristyrylphenol) having an average degree of ethoxylation of between 10 and 80, preferably from 16 to 40, such as, for example, Soprophor® B
  • Preferred ionic surfactants for use in this invention include: polyalkoxylated, preferably polyethoxylated, surfactants which are ionically modified, for example by conversion of the terminal free hydroxyl function of the polyethylene oxide block into a sulfate or phosphate ester (for example as alkali metal and alkaline earth metal salts), such as, for example, Genapol® LRO or dispersant 3618 (Clariant), Emulphor® (BASF) or Crafol® AP (Cognis); alkali metal and alkaline earth metal salts of alkylarylsulfonic acids having a straight-chain or branched alkyl chain, such as phenylsulfonate CA or phenylsulfonate CAL (Clariant), Atlox® 3377BM (Croda), or the Empiphos® TM series (Huntsman); polyelectrolytes, such as lignosulfonates, condensates of
  • OMS organo-modified siloxanes
  • WG2008/155108 those disclosed in WG2008/155108
  • polyether-polysiloxane copolymers described in GB 2496643 including those available from Evonik Industries under the trade names Break-Thru 9902TM, Break-Thru 9903TM, Break-Thru 5503TM, Break-Thru 9907TM and Break-Thru 9908TM.
  • the surfactant may comprise lignosulfonates.
  • the amount of the one or more lignosulfonates in the compositions of the present invention can range from about 0.1 to about 20% by weight, but for reasons of cost the amount is typically no more than about 10%, preferably no more than about 8%, more preferably no more than about 6% and most preferably no more than about 5% of the composition by weight.
  • the one or more lignosulfonates amount to at least about 0.5% of the composition by weight, although lesser amounts down to about 0.1% can be used. More typically the one or more lignosulfonates amount to at least about 1% of the composition and even more typically at least about 2% of the composition by weight.
  • Lignin the basic building block of the lignosulfonates of this invention is formed in woody plants and is a complex natural polymer regarding structure and homogeneity.
  • Lignosulfonates are sulfonated plant lignins and are commercially well-known co-products of the paper industry.
  • the lignosulfonates useful in the present compositions can be prepared by a chemical modification of the basic lignin building block using a sulfite pulping process or a kraft pulping (also known as sulfate pulping) process including subsequent sulfonation. These pulping processes are well known in the paper industry.
  • Crude lignosulfonate preparations typically contain in addition to sulfonated lignin other plant derived chemicals such as sugars, sugar acids and resins, as well as inorganic chemicals. Although such crude lignosulfonate preparations can be used for the compositions of the present invention, preferably the crude preparations are first refined to provide higher purity of lignosulfonate.
  • Lignosulfonates within the context of the present disclosure and claims also include lignosulfonates that have been extensively chemically modified.
  • lignosulfonates that have been extensively chemically modified are oxylignins in which the lignin has been oxidized in a process reducing the number of sulfonic acid and methoxyl groups and causing rearrangements increasing the number of phenolic and carboxylic acid groups.
  • An example of an oxylignin is Vanisperse A marketed by Borregaard LignoTech.
  • Lignosulfonates vary according to cation, degree of sulfonation and average molecular weight.
  • the lignosulfonates of the present invention can contain sodium, calcium, magnesium, zinc, potassium or ammonium cations or mixtures thereof, but preferably contain sodium.
  • the degree of sulfonation is defined as the number of sulfonate groups per 1000-unit molecular weight of lignosulfonate and in commercially available products typically ranges from about 0.5 to about 4.7.
  • the lignosulfonates in the compositions of the present invention preferably contain a degree of sulfonation ranging from about 0.5 to about 3.0.
  • Lignosulfonates containing a degree of sulfonation from about 0.5 to about 3.0 can be prepared by controlled sulfonation in the kraft pulping process.
  • the degree of sulfonation using the kraft pulping process is 2.9 for REAX 88A, 0.8 for RE AX 85A and 1.2 for REAX 907, which are described further below.
  • Average molecular weight of commercially available lignosulfonates typically ranges from about 2,000 to about 15,100.
  • the lignosulfonates of the present invention preferably have an average molecular weight above about 2,900.
  • Examples of commercially available refined lignosulfonate products useful in the compositions of the present invention include, but are not limited to, REAX 88A (sodium salt of a chemically modified low molecular weight kraft lignin polymer solubilized by five sulfonate groups, marketed by MeadWestvaco Corp.), RE AX 85A (sodium salt of a chemically modified high molecular weight kraft lignin polymer, marketed by MeadWestvaco Corp.), REAX 907 (sodium salt of a chemically modified high molecular weight kraft lignin polymer, marketed by MeadWestvaco Corp.), RE AX 100M (sodium salt of a chemically modified low molecular weight kraft lignin polymer marketed by MeadWestvaco Corp.) and Kraftspearse® DD-5 (sodium salt of a chemically modified high molecular weight kraft lignin polymer, marketed by MeadWestvac
  • anionic surfactants for this purpose are sulfonates such as calcium dodecyl benzenesulfonate.
  • nonionic surfactants are polyoxyethylated (POE) sorbitan esters such as POE (20) sorbitan trioleate and polyoxyethylated (POE) sorbitol esters such as POE (40) sorbitol hexaoleate.
  • POE (20) sorbitan trioleate is commercially available under the tradename Tween® 85 marketed by Uniqema.
  • POE (40) sorbitol hexaoleate is commercially available under the tradenames Atlas G1086 and CirrasolTM G-1086 marketed by Uniqema.
  • Other particularly suitable nonionic surfactants include polyethoxylated poly(12-hydroxystearic acid) having a degree of ethoxylation of between 10 and 80, preferably from 25 to 40.
  • a combination of a POE sorbitan ester with a POE sorbitol ester allows optimizing the HLB (hydrophilic-lipophilic balance) value of the surfactant to obtain the highest quality emulsion (smallest suspended droplets) when the composition is added to water. High quality of emulsions typically leads to optimal herbicidal performance.
  • a surfactant combination may comprise one or more nonionic surfactant in combination with one or more anionic surfactant.
  • composition of the present invention comprising one or more nonionic surfactants selected from polyethoxylated poly (12-hydroxystearic acid), polyoxyethylated (POE) sorbitan esters such as POE (20) sorbitan trioleate and polyoxyethylated (POE) sorbitol esters such as POE (40) sorbitol hexaoleate and mixtures thereof.
  • nonionic surfactants selected from polyethoxylated poly (12-hydroxystearic acid), polyoxyethylated (POE) sorbitan esters such as POE (20) sorbitan trioleate and polyoxyethylated (POE) sorbitol esters such as POE (40) sorbitol hexaoleate and mixtures thereof.
  • a notable combination of surfactants comprises a nonionic polymeric surfactant comprising a polyethoxylated poly (12-hydroxystearic acid), a nonionic polymeric surfactant comprising polyoxyethylene (40) sorbitol hexaoleate and an anionic surfactant comprising a calcium linear alkyl( such as C 12 )benzene.
  • the surfactant is preferably included in an amount of at least 1 weight% with respect to the total weight of the composition.
  • the surfactant is preferably included in the composition in an amount of 60 weight% or less. More preferably, the surfactant comprises an amount in a range from a lower limit of at least 2 weight%, 5 weight%, 10 weight%, 15 weight%, or 20 weight% to an upper limit of 50 weight%, 40 weight%, or 30 weight% of the total liquid composition. Any of the disclosed lower weight% limits can be combined with any of the disclosed upper weight% limits to define further suitable weight% ranges for the purposes of this invention.
  • Exemplary ranges of the amount of surfactant in the liquid composition include 1 to 60 weight%, 2 to 50 weight%, 5 to 40 weight%, 10 to 30 weight%, 5 to 50 weight% and 2 to 40 weight%. Where more than one surfactant is used the preferred ranges refer to the total amount of surfactant present in the liquid composition.
  • the present compositions can also contain one or more solid diluents in suspension in the liquid carrier.
  • the solid diluents can be water-soluble or water-insoluble. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
  • water-soluble solid diluents include salts such as alkali metal phosphates (e.g., sodium dihydrogen phosphate), alkaline earth phosphates, sulfates of sodium, potassium, magnesium and zinc, sodium and potassium chloride, and sodium benzoate, and sugars and sugar derivatives such as sorbitol, lactose and sucrose.
  • alkali metal phosphates e.g., sodium dihydrogen phosphate
  • alkaline earth phosphates e.g., sulfates of sodium, potassium, magnesium and zinc, sodium and potassium chloride, and sodium benzoate
  • sugars and sugar derivatives such as sorbitol, lactose and sucrose.
  • water- insoluble solid diluents include, but are not limited to, clays, synthetic and diatomaceous silicas, calcium and magnesium silicates, titanium dioxide, aluminum, calcium and zinc oxide, calcium and magnesium carbonate, sodium, potassium, calcium and barium sulfate,
  • Certain solid diluents such as clays have been discovered to provide significant resistance to separation of suspended or dispersed solid particles in the present composition, which otherwise would result in formation of a bleed layer (i.e. layer not containing suspended or dispersed solid particles). Further, it has been discovered that these solid diluents can impart a reversible gel structure to the composition.
  • a reversible gel provides high viscosity to the composition at low shear (e.g., when the composition is stored in a container), but low viscosity facilitating pouring results when high shear is applied (e.g., when a container of the composition is shaken).
  • a benefit of reversible gel structure is that formation of a bleed layer and sedimentation of particles to the bottom of the container are significantly reduced.
  • a composition of this invention containing at least about 0.1% clay by weight will form a reversible gel. More than 10% clay can be useful, but for reason of cost, no more than about 10% is preferred. More preferred is a range of from 0.1 to 5%, and most preferred is a range of from 0.5 to 3%.
  • Examples of clays useful in the present composition include magnesium aluminum silicates such as attapulgite (e.g., Attagel® 50 from BASF Corp.) and other aluminum silicates such as montmorillonite (e.g., Barden® clay from the Kentucky-Tennessee Clay Co.
  • formulation ingredients can be used in the present invention such as rheology modifiers, wetting agents, dyes, defoamers, drying agents, and the like. These ingredients are known to one skilled in the art and can be found described, for example, in McCutcheon’s 2001, Volume 2: Functional Materials published by MC Publishing Company.
  • composition of the invention can be prepared by known processes, for example by mixing the components and milling the suspended solids or dissolving the solids.
  • Any soluble agrochemically active compounds used can also be dissolved in the premix.
  • solid sulfonylurea, any other insoluble agrochemically active compounds used and the inorganic salts can be suspended in the mixture.
  • the methods for making the suspensions and dispersions of sulfonylurea particles useful for the compositions of the present invention are well known and include grinding, ball-milling, beadmilling, sand-milling, colloid milling and air-milling combined with high-speed blending.
  • the Examples of the present disclosure use a bead-milling process.
  • the coarse suspension is, if appropriate after milling or pregrinding, subjected to fine grinding.
  • solid sulfonylurea and, if appropriate, any insoluble components used are suspended in the non-aqueous liquid carrier and subjected to grinding. Any soluble active compounds used and any auxiliaries and additives which do not require grinding or are not required for the grinding process can be added after grinding.
  • customary mixing apparatus which, if required, are thermostatted.
  • pre-grinding it is possible to use, for example, high-pressure homogenizers or mills operating by the rotor-stator principle, such as Ultraturrax homogenizers, for example those from IKA, or toothed colloid mills, for example from Puck or Fryma.
  • Ultraturrax homogenizers for example those from IKA
  • toothed colloid mills for example from Puck or Fryma
  • fine grinding it is possible to use, for example, bead mills which operate batchwise, for example from Drais, or bead mills which operate continuously, for example from Bachofen or Eiger.
  • the sulfonylurea, the alkali metal silicate salt and the non- aqueous liquid carrier are selected such that the sulfonylurea exhibits at least 60% chemical stability.
  • the sulfonylurea exhibits at least 70% chemical stability, at least 80% chemical stability, at least 90% chemical stability, at least 95% chemical stability, and at least 98% chemical stability.
  • Chemical stability can be determined as a percentage of the sulfonylurea remaining (e.g., as determined by HPLC) when the liquid composition (e.g., a 50 mL sample of the liquid composition in a 60 mL hermetically sealed Winchester bottle) has been stored at an elevated temperature (e.g., 45 °C or 54 °C for periods ranging from 3 days to two weeks, such as at 45 °C for one week or two weeks, or at 54 °C for one week or two weeks).
  • the sample stored at an elevated temperature may be compared to a corresponding control sample that has been stored at -10 °C for two weeks or a corresponding control sample assayed less than one day after its preparation.
  • the liquid composition is one where chemical stability of the sulfonylurea is improved by at least 2% compared to a corresponding liquid composition that does not contain an alkali metal silicate according to the invention (instead of the silicate, an equivalent weight% of sodium phosphate is used).
  • Chemical stability of the sulfonylurea for each of the silicate-containing liquid composition and the non-silicate comparative composition can be determined as described immediately above. The difference in chemical stability can then be calculated to determine that an improvement of at least 2% is achieved.
  • the sulfonylurea exhibits at least a 5% improvement, more preferably at least a 10% improvement, and even more preferably at least a 50% improvement in chemical stability.
  • the liquid composition is one where the sulfonylurea exhibits at least 20% chemical stability (as described above), and is one where the chemical stability of the sulfonylurea is improved by at least 10% compared to a corresponding liquid composition that does not contain an inorganic silicate according to the invention (as described above).
  • the sulfonylurea exhibits at least 60% chemical stability, at least 70% chemical stability, at least 80% chemical stability, at least 90% chemical stability, at least 95% chemical stability, or at least 98% chemical stability.
  • This invention also relates to a method for controlling unwanted vegetation comprising applying a herbicidally effective amount of a composition as defined herein, including any of Embodiments 1 through 125, to a locus where such control is desired. Accordingly, this invention also relates to the use of a composition as defined herein, including any of Embodiments 1 through 125 for controlling unwanted vegetation.
  • compositions of this invention comprising tribenuron- methyl are useful for selective postemergence broadleaf weed control, including annual sowthistle, black mustard, blue/purple mustard, burning nettle, bushy wallflower/treacle mustard, Canada thistle, coast fiddleneck, common chickweed, common cocklebur, common dandelion, common groundsel, common lambsquarters, common purslane, common sunflower, com gromwell, com spurry, cowcockle, curly dock, deadnettle, dog fennel, early whitlowgrass, eastern black nightshade, false chamomile, field pennycress, flixweed, hairy buttercup, hairy nightshade, henbit, knotweed (prostrate), kochia, London rocket, marshelder, mayweed chamomile, miners lettuce, nightflowering catchfly, Pennsylvania smartweed, pineappleweed, prickly lettuce, puncturevine, redmaids, redroot pigweed,
  • compositions of this invention comprising tribenuron- methyl in combination with fluroxypyr-meptyl are useful for selective postemergence for control of annual and perennial broadleaf weeds and volunteer potatoes in wheat, barley, oats, or triticale not under-seeded with a legume, field com, sweet com, grain sorphum, and on-farm non-cropland.
  • Other crops include apple, bermudagrass, bluegrass, brome, crabapple, fescue, grass, loquat, mayhaw, millet, onion, orchardgrass, pear, quince, redtop, ryegrass, sudex and timothy.
  • weeds controlled by tribenuron-methyl include bedstraw, buckwheat, canola, chickweed, cleaver, cocklebur, devil's-claw, dogsbane, goldenrod, horsetail, kochia, lettuce, mallow, marestail, momingglory, pennycress, ragweed, sunflower, velvetleaf and vetch.
  • Compositions comprising fluroxypyr-meptyl are particularly effective on Kochia and chickweed, especially weed biotypes resistant to tribenuron.
  • compositions of this invention comprising tribenuron- methyl in combination with an MCPA ester are useful for selective postemergence broadleaf weed control in wheat, barley, rye, flax (excluding low linolenic acid varieties), pastures, roadsides and non-cropland areas.
  • weeds controlled by tribenuron-methyl include annual sow-thistle, burdock (before the 4-leaf stage), cocklebur, curled dock, plantain, flixweed, hemp-nettle, lambsquarters, mustards (except dog and tansy), prickly lettuce, ragweeds (including Group 2 and glyphosate-tolerant biotypes), Russian and other pigweed species, shepherd’ s-purse, stinkweed, vetch, wild radish and wild (annual) sunflower.
  • Compositions comprising a MCPA ester are particularly effective on weed biotypes resistant to tribenuron-methyl.
  • compositions of this invention comprising tribenuron- methyl and thifensulfuron-methyl are useful for selective postemergence broadleaf weed control in wheat (including durum), barley, oat, triticale and fallow.
  • Notable weeds controlled include annual knawel, annual sowthistle, black mustard, blue/purple mustard, broadleaf dock, bur buttercup, bushy wallflower/treacle mustard, Canada thistle, Carolina geranium, catchweed bedstraw, clasping pepperweed, coast fiddleneck, common buckwheat, common chickweed, common cocklebur, common groundsel, common lambsquarters, common mallow, common radish, common ragweed, common sunflower, com chamomile, com gromwell, com spurry, cowcockle, cress (mouse-ear), curly dock, cutleaf evening primrose, cutleaf nightshade, dandelion, false chamomile, field chickweed, field pennycress, flixweed, hairy nightshade, hempnettle, henbit, kochia, ladysthumb, lanceleaf sage, london rocket, little mallow, marshelder, mayweed cham
  • compositions of this invention comprising tribenuron- methyl, thifensulfuron-methyl and fluroxypyr-meptyl are useful for selective postemergence broadleaf weed control in wheat (including durum), barley, oat, triticale and fallow.
  • the compositions are also for selective postemergence control of annual and perennial broadleaf weeds and volunteer potatoes in small grains, field com, sweet com, grain sorghum, on-farm non- cropland, and grasses grown for seed, forage or hay.
  • weeds controlled by tribenuron-methyl and thifensulfuron-methyl include bedstraw, buckwheat, canola, chickweed, cleaver, cocklebur, devil's-claw, dogsbane, goldenrod, horsetail, kochia, lettuce, mallow, marestail, momingglory, pennycress, ragweed, sunflower, velvetleaf and vetch.
  • Compositions comprising fluroxypyr-meptyl are particularly effective on Kochia and chickweed, especially weed biotypes resistant to tribenuron-methyl and thifensulfuron-methyl.
  • a composition of the invention can be applied directly or can be diluted with water and then applied to plant foliage and/or soil by methods commonly employed in the art, such as conventional high-volume hydraulic sprays, low-volume sprays, air-blast, and aerial sprays.
  • the diluted composition may be applied to the plant foliage or to the soil or area adjacent to the plant.
  • the selection of the specific herbicidal compounds in the composition are determined by the selectivity of the herbicidal compounds to specific crops and by the prevalent weed species to be controlled and are known to those skilled in the art (e.g., see “The Pesticide Manual” (ISBN- 10: 190139686X) and all earlier editions thereof).
  • Tribenuron-methyl (technical grade, 99% purity) available from EMC.
  • Thifensulfuron-methyl (technical grade, 99% purity) available from EMC.
  • Metsulfuron (technical grade, 99% purity) available from EMC.
  • Fluroxypyr-meptyl (technical grade, 98% purity) available from Dow Chemicals.
  • MCPA EH (2-ethylhexyl ester available as an emulsifible concentrate; 95.9% from Nufarm Americas, Inc., Alsip, IL).
  • Potassium silicate (commercial grade from Beantown Chemical).
  • Steposol® ME a mixture of methyl oleate and methyl linoleate available commercially from Stepan Company, Northfield, Illinois.
  • AtloxTM 4914 a medium molecular weight nonionic polymeric surfactant comprising a hydrophilic portion comprising polyethylene oxide (PEG) and a hydrophobic portion comprising poly (12-hydroxystearic acid) (pHSA) having an HLB of 6, commercially available from Croda International Pic, Snaith Goole, East Yorkshire, United Kingdom.
  • CirrasolTM G-1086 a nonionic polymeric surfactant comprising polyoxyethylene (40) sorbitol hexaoleate having an HLB of 10, commercially available from Croda International Pic, Snaith Goole, East Yorkshire, United Kingdom.
  • Ninate® 60L an anionic surfactant comprising 60% active linear (C 12 alkyl) calcium alkylbenzene sulfonate in a non-aqueous carrier, commercially from Stepan Company, Northfield, Illinois.
  • Tween® 85 Polyoxyethylene (20) sorbitan trioleate commercially available from Croda International Pic, Snaith Goole, East Yorkshire, United Kingdom.
  • Bentone® 1000 an organic solvent-borne derivative of bentonite clay, commercially available from Elementis, East Windsor, NJ.
  • Oil dispersions containing tribenuron-methyl, or tribenuron-methyl and thifensulfuron- methyl, and optionally further containing MCPA ester or fluroxypyr-meptyl were prepared according to the following general procedure.
  • the same surfactants and thickener were used in each formulation at approximately the same ratios in each formulation, as shown in Table B.
  • the same liquid carrier was also used in all the formulations, with the amount adjusted to accommodate the amounts of active ingredients and formulation components in each composition.
  • the slurry was charged into an Eiger 50 Mini VSE Mill to reduce the particle size of technical to a DV90 ⁇ 10 microns (0.6 mm YTZ media, milling chamber cooled to 5 °C with a chiller; milling time was 45-60 min).
  • the stability of the sulfonylureas in the following compositions was determined by aging samples at ambient ( ⁇ 23 °C) or elevated temperatures in heated ovens for various periods of time as indicated in Tables 1 through 8. For example, stability samples were stored in an oven and kept at a controlled temperature of 54 ⁇ 1 °C for 3 to 14 days. The samples were then removed from storage and the stored samples were compared to identical samples assayed before aging to determine the amount of intact sulfonyl remaining as a percentage (%). Sulfonylurea content immediately after preparation and after the indicated storage conditions for each formulation was determined by assaying the compositions with high-pressure liquid chromatography (HPLC) using reverse phase columns and eluants.
  • HPLC high-pressure liquid chromatography
  • Comparative Example C1 is a composition that did not contain a silicate stabilizer component.
  • Comparative Examples C2 and C3 were compositions that contained sodium phosphate, taught in WO2016/102499 to be useful in stabilizing sulfonylureas.
  • Comparative Example C1 showed that tribenuron-methyl can be completely decomposed under accelerated heat aging without a stabilizer. Comparative Examples C2 and C3 showed that sodium phosphate improved stability of tribenuron-methyl under accelerated heat aging. Examples 1 and 2, compositions of this invention, demonstrated that sodium silicate effectively stabilizes tribenuron-methyl under accelerated heat aging. Notably, sodium silicate provided better stability for tribenuron-methyl than sodium phosphate.
  • Table 2 summarizes compositions comprising tribenuron-methyl alone and combined with either fluroxypyr-meptyl or MCPA-ester.
  • Comparative Examples C4, C5 and C6 are compositions that do not contain a silicate stabilizer component.
  • Comparative Examples C4, C5 and C6 showed that tribenuron-methyl was completely decomposed under accelerated heat aging without a stabilizer.
  • Examples 3, 4 and 5, compositions of this invention demonstrated that sodium silicate effectively stabilizes tribenuron-methyl, including when co-formulated with fluroxypyr-meptyl or MCPA-ester, under accelerated heat aging.
  • Comparative Example C7 was a composition that contained sodium phosphate, taught in WO2016/102499 to be useful in stabilizing sulfonylureas.
  • Comparative Example C7 showed that sodium phosphate can stabilize tribenuron-methyl under accelerated heat aging at 45 °C for 7 days but could not stabilize tribenuron-methyl under more rigorous accelerated heat aging at 54 °C for 14 days.
  • Examples 6 and 7, compositions of this invention demonstrated that sodium silicate effectively stabilizes tribenuron-methyl under both heat aging protocols.
  • sodium silicate provides better stability for tribenuron-methyl than sodium phosphate.
  • Sodium silicate provided better stabilization than compositions comprising an equal amount of sodium phosphate at both 45 °C and 54 °C (Example 6 compared to Comparative Example C7).
  • Example 7 with about one-third less sodium silicate than sodium phosphate on a weight basis, provided stability comparable to or superior to that of Comparative Example C7 at 45 °C for 7 days.
  • Example 7 also was superior to Comparative Example C7, providing some stability for tribenuron-methyl at 54 °C for 14 days, while Comparative Example C7 had no tribenuron-methyl remaining.
  • Both Example 6 and Example 7 provided stabilization of thifensulfuron-methyl comparable to Comparative Example C7 at 54 °C for 14 days.
  • Table 4 summarizes compositions comprising tribenuron-methyl, thifensulfuron-methyl and fluroxypyr-meptyl (In Table 4, “NT’ stands for “not tested”).
  • Comparative Example C8 was a composition that contains sodium phosphate, taught in WO2016/102499 to be useful in stabilizing sulfonylureas. Storage stability was assessed at several temperatures for Comparative Example C8, which showed increasing degradation of tribenuron-methyl and thifensulfuron-methyl at higher temperatures. Tribenuron-methyl was largely degraded when stored at 54 °C for 3 days.
  • Example 8 a composition of this invention, demonstrates that sodium silicate effectively stabilizes tribenuron- methyl under accelerated heat aging at 54 °C for 4 days. Notably, sodium silicate was superior to sodium phosphate in providing stability for tribenuron-methyl. Heat aging data of Example 8 compared to Comparative Example C8 at 54 °C showed significantly superior stability was achieved using sodium silicate. Sodium silicate also provided effective stabilization of thifensulfuron-methyl. Fluroxypyr-meptyl was not affected by the heat aging treatment.
  • Table 5 summarizes compositions comprising metsulfuron with or without sodium silicate stabilizer.
  • Comparative Example C9 is a composition that did not contain a silicate stabilizer. Metsulfuron was largely degraded when stored at 54 °C for 14 days.
  • Example 9 a composition of this invention, demonstrates that sodium silicate effectively stabilizes metsulfuron under accelerated heat aging at 54 °C for 7 days, and was significantly superior to Comparative Example C9 at stabilizing metsulfuron under accelerated heat aging at 54 °C for 14 days.
  • Table 6 summarizes compositions comprising tribenuron-methyl stabilized with sodium silicate, sodium phosphate, sodium carbonate, and mixtures of sodium silicate with sodium phosphate or sodium carbonate. (In Table 6, wt.% means weight%.)
  • Comparative Examples C10 and C11 were compositions that contained sodium phosphate or sodium carbonate, taught in WO2016/102499 to be useful in stabilizing sulfonylureas. Heat aging was conducted at at 40 and 54°C for 7 days.
  • Example 10 a composition of this invention, comprising sodium silicate-stabilized tribenuron-methyl performed comparably to Comparative Examples C11 and C12.
  • Examples 11-14 showed that mixtures of sodium silicate with sodium phosphate or sodium carbonate were also effective at stabilizing tribenuron-methyl.
  • Table 7 summarizes compositions comprising tribenuron-methyl stabilized with potassium silicate, sodium silicate pentahydrate, anhydrous sodium metasilicate or sodium orthosilicate.
  • silicates other than anhydrous sodium metasilicate are also useful in stabilizing tribenuron-methyl.
  • Formulations including sodium orthosilicate (Examples 18 and 19) exhibited increased viscosity during milling, which limited the ability to produce samples with higher salt loading levels.
  • Potassium silicate provided excellent stability under extended high temperature storage conditions (Example 15).
  • Table 8 summarizes formulations containing tribenuron-methyl stabilized with sodium silicate with and without fluroxypyr-meptyl or S-metolachlor. (In Table 8, wt.% means weight%.)
  • Sodium silicate provided very good stabilization at 54 °C for 14 days for each of Examples 20-22. Complete loss of tribenuron-methyl was observed for formulations containing sodium silicate and tribenuron-methyl with fluroxypyr-meptyl or S-metolachlor.

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Abstract

La présente invention concerne une composition herbicide liquide comprenant un support liquide non aqueux, au moins un herbicide de sulfonylurée et au moins un sel inorganique choisi parmi les silicates de métaux alcalins, ainsi qu'un procédé de lutte contre la végétation indésirable à l'aide de la composition. L'invention concerne également l'utilisation d'un sel inorganique choisi parmi les silicates de métaux alcalins pour améliorer la stabilisation chimique d'un herbicide de sulfonylurée dans une composition liquide comprenant un support liquide non aqueux.
EP21711356.2A 2020-01-29 2021-01-28 Compositions de sulfonylurée liquides Pending EP4096400A1 (fr)

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