WO2023159064A1 - Compositions herbicides - Google Patents

Compositions herbicides Download PDF

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Publication number
WO2023159064A1
WO2023159064A1 PCT/US2023/062658 US2023062658W WO2023159064A1 WO 2023159064 A1 WO2023159064 A1 WO 2023159064A1 US 2023062658 W US2023062658 W US 2023062658W WO 2023159064 A1 WO2023159064 A1 WO 2023159064A1
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Prior art keywords
als
inhibitor herbicide
als inhibitor
herbicide
imazapyr
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PCT/US2023/062658
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English (en)
Inventor
Virginia Marie URSIN
Hope Hsiao-Wang DANISON
Barry Andrew Martin
Yajie NIU
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Invaio Sciences, Inc.
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Publication of WO2023159064A1 publication Critical patent/WO2023159064A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides

Definitions

  • This application generally relates to the field of herbicides
  • Acetolactate synthase also known as acetohydroxyacid synthase, is the target for more than 50 commercial herbicides used globally to protect crops such as rice, com, wheat, and cotton.
  • ALS inhibitors There are various classes of ALS inhibitors. ALS inhibitors have several unique benefits including: (1) ability to control abroad spectrum of broadleaf weeds and grasses at rates ranging from 10 to 200g/ha; and (2) safety for non-target organisms including mammals, fish, birds, and insects because ALS does not exist in these organisms.
  • This disclosure provides herbicidal compositions containing a DHAD (dihydroxy acid dehydratase) inhibitor and at least one acetolactate synthase (ALS) inhibitor.
  • the DHAD inhibitor is aspterric acid or an agriculturally acceptable derivative thereof.
  • the compositions can be used to control undesirable vegetation that is otherwise resistant to treatment with an ALS herbicide inhibitor.
  • herbicidal compositions relying on the synergistic action of the aspterric acid or an agriculturally acceptable derivative thereof.
  • the disclosure is directed to herbicidal compositions containing: aspterric acid or an agriculturally acceptable derivative thereof; and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or ester (such as e.g. an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and/or combinations thereof).
  • the composition contains an herbicidal synergistic amount and/or ratio of the aspterric acid and the at least one ALS inhibitor herbicide and/or controls undesirable vegetation that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • the imidazolinone is selected from at least one of imazapyr, imazaquin, imazamethabenz-methyl, imazamox, imazapic, imazethapyr, and an environmentally compatible salt or ester thereof.
  • the disclosure is directed to methods for controlling undesirable vegetation in a field of crop plants which includes applying these herbicidal compositions to the field (i) prior to planting the crop plant or (ii) after planting and prior to emergence of the crop plant.
  • the disclosure is directed to methods controlling undesirable vegetation in a field comprising undesirable vegetation and a crop plant having tolerance to an ALS inhibitor herbicide.
  • the methods comprise applying an effective amount of theses herbicidal compositions to the field containing the crop plant to control the undesirable vegetation without significantly affecting the crop plant.
  • the DHAD inhibitor and the ALS inhibitor herbicide are applied concurrently.
  • the DHAD inhibitor and the ALS inhibitor herbicide are applied sequentially during a planting season.
  • the disclosure provides methods for controlling undesirable vegetation in a field of crop plants, the methods including applying a herbicidal composition to the field (i) prior to planting the crop plant or (ii) after planting and prior to emergence of the crop plant.
  • the herbicidal compositions used in the methods comprise an aspterric acid or an agriculturally acceptable derivative thereof; and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or ester (such as e.g. an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof).
  • ALS acetolactate synthase
  • the undesirable vegetation comprises one or more plants that are otherwise resistant to the at least one ALS inhibitor herbicide (such as e.g. imazapyr and/or a mixture comprising imazapyr and glyphosate).
  • the imidazolinone comprises at least one compound selected from the group consisting of imazapyr, imazaquin, imazamethabenz-methyl, imazamox, imazapic, imazethapyr, and an environmentally compatible salts or esters thereof.
  • the disclosure also provides for methods of improving efficacy of an ALS inhibitor herbicide against undesirable vegetation comprising plants resistant to the ALS inhibitor herbicide.
  • the methods comprise mixing aspterric acid or an agriculturally acceptable derivative thereof and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or ester (such as e.g. imazapyr and/or a mixture comprising imazapyr and glyphosate).
  • ALS acetolactate synthase
  • the methods increase the efficacy of the ALS inhibitor herbicide relative to the efficacy observed when the ALS inhibitor herbicide is used in the absence of the aspterric acid.
  • the disclosure provides for methods of improving efficacy of an ALS inhibitor herbicide comprising mixing aspterric acid or an agriculturally acceptable derivative thereof and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or esters at a molar ratio (such as e.g. imazapyr and/or a mixture comprising imazapyr and glyphosate) in the range of 100: 1 to 1 :5.
  • ALS acetolactate synthase
  • the methods increase the efficacy of the ALS inhibitor herbicide relative to the efficacy observed when the ALS inhibitor herbicide is used in the absence of the aspterric acid.
  • the disclosure provides for methods of controlling undesirable vegetation comprising contacting undesirable vegetation with an herbicidal composition
  • an herbicidal composition comprising: aspterric acid or an agriculturally acceptable derivative thereof; and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or esters (such as e.g. imazapyr and/or a mixture comprising imazapyr and glyphosate).
  • the composition contains an herbicidal synergistic amount and/or of the aspterric acid and the at least one ALS inhibitor herbicide.
  • the composition controls undesirable vegetation that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • the crop plant is genetically modified or genetically engineered to contain genetic material that confers resistance or tolerance to at least one ALS inhibiting herbicide.
  • the crop plant is selected from the group consisting of soybean, cotton, corn, sugar beet, peanut, rice, wheat, canola, alfalfa, sugarcane, sorghum, sunflower, and conifer crop species.
  • the conifer crop species is selected from the group consisting of Loblolly Pine (Pinus taeda). Loblolly X Pitch Hybrid, Longleaf Pine (Pinus palustris).
  • Shortleaf Pine Pine (Pinus echinata), Virginia Pine (Pinus virginiand), Slash Pine (Pinus elliottii), Douglas Fir (Pseudotsuga menziesii). Coastal Redwood (Sequoia sempervirens), Western Hemlock (Tsuga heterophylld), California Red Fir (Abies magnified), California White Fir (Abies concolor), Jack Pine (Pinus banksiana), Lodgepole Pine (Pinus conlorta). Pitch Pine (Pinus rigida), Ponderosa Pine (Pinus ponderosa). Sugar Pine (Pinus lambertiand), White Pine (Pinus slrobus). Black Spruce (Picea mariana). Red Spruce (Picea rubens), and White Spruce (Picea glauca).
  • FIG. 1 depicts the branched -chain amino acid biosynthetic pathway that is present in bacteria, archaea, fungi, and plants.
  • DHAD is involved in the conversion of dihydroxyisovalerate to ketoisovalerate and in the conversion of dihydroxymethylvalerate to ketomethylvalerate.
  • Ketoisovalerate and Ketomethyl valerate are precursors to valine, leucine, and isoleucine.
  • FIG. 2 depicts the relative efficacy of aspterric acid, imazapyr, and Roundup® towards Arabidopsis strain Col-0. Plotted are plant weight as a function of the concentration of the compounds used. Plant weight was determined fourteen days after treatment. Results show the average and standard deviation of an experiment with eight sample replicates per group.
  • FIG. 3 depicts a comparison between the susceptibility of Arabidopsis strain Col-0 and imazapyr-resistant Arabidopsis strain Csrl-2, to aspterric acid.
  • FIG. 4 shows the relative efficacy of imazapyr (“ima”), aspterric acid (“aa”) and the combination of imazapyr and aspterric acid towards Arabidopsis strain Col-0. Plotted are the plant weight as a function of the concentration of the compounds, tested either alone or in combination, at the indicated concentrations. Plant weight was determined fourteen days after treatment. Results show the average and standard deviation of two experiments, each with eight sample replicates per group.
  • ima imazapyr
  • aa aspterric acid
  • FIG. 5A-5D depict a comparison of the relative efficacy of imazapyr, aspterric acid and the combination of imazapyr and aspterric acid towards Arabidospsis strain Col-0 (FIG. 5 A and FIG. 5B) and Arabidopsis strain Csrl-2 (FIG. 5C and FIG. 5D). Plotted are the plant weight as a function of the concentration of the compounds, tested either alone or in combination, at the indicated concentrations. Plant weight was determined fourteen days after treatment. Results show the average and standard deviation of an experiment with eight sample replicates per group.
  • FIG. 6A-6B depict images of Barnyard grass (FIG. 6A) and Palmer Amaranth (FIG. 6B), four days post-spray after herbicide treatment.
  • imazapyr 1% of the commercially available formulation Ecomazapyr in water
  • FIG. 7A-7B depict images of Arabidopsis Col-0 (FIG. 7 A) and Arabidopsis csrl-2 (FIG. 7B) plants, four days post-spray.
  • FIG. 8A-8B depict images Barnyard grass treated imazapyr and aspterric acid combinations, seven days post-treatment.
  • FIG. 8 A Ima: 2 mL imazapyr (1% in water); Ima+ AA: combination of 1 ml of 1% Imazapyr and 1 ml of aspterric acid (comprising 100 ⁇ M in 5mM MES and 0.05% silwet, pH 5.5); Water: 2 mL water.
  • FIG. 8B Barnyard grass treated first with imazapyr and then aspterric acid or with the combination of imazapyr and aspterric acid.
  • Ima-> AA sprayed 1 mL imazapyr (1% in water) followed by spraying 1 mL aspterric acid (100 ⁇ M in 5mM MES and 0.05% silwet, pH 5.5); Ima+ AA: 2 mL combined imazapyr and aspterric acid solution.
  • compositions containing a combination of a DHAD inhibitor (e.g. aspterric acid) and an acetolactate synthase (ALS) inhibitor herbicide are more effective than using the individual components alone.
  • a DHAD inhibitor e.g. aspterric acid
  • ALS acetolactate synthase
  • ALS inhibitor-resistance is conferred through substitutions of at least one of Alal22, Prol97, Ala205, Asp376, Arg377, Trp574, Ser653, and Gly654 in ALS.
  • Ser653 is substituted by Asn653, conferring resistance of a plant to ALS inhibitors.
  • Ser653Asn is substituted by Asn653 (Ser653Asn), conferring resistance to ALS inhibitors.
  • Arabidopsis csrl-2 is resistant to imazapyr.
  • Arabidopsis csrl-2 is sensitive to aspterric acid.
  • Arabidopsis csrl-2 is sensitive to the combination of an ALS inhibitor (e.g. imazapyr) and aspterric acid.
  • an ALS inhibitor e.g. imazapyr
  • imazapyr and an ALS inhibitor act synergistically in inhibiting the growth of undesired vegetation.
  • compositions containing aspterric acid or an agriculturally acceptable derivative thereof may be used as an effective herbicide against plants that are resistant to imazapyr.
  • aspterric acid does not hinder imazapyr efficacy.
  • a DHAD inhibitor and an ALS inhibitor have a synergistic effect on growth inhibition.
  • aspterric acid and imazapyr act synergistically in growth inhibition.
  • aspterric acid and imazypyr act synergistically in inhibiting the growth of a plant that is resistant to ALS inhibitors (e.g. imazapyr).
  • aspterric acid inhibits the activity of DHAD (dihydroxy acid dehydratase).
  • DHAD is an enzyme that is present in the branched-chain amino acid (valine, leucine, and isoleucine) biosynthetic pathway that is present in bacteria, archaea, fungi, and plants (FIG. 1). In this pathway, DHAD is involved in the conversion of dihydroxyisovalerate to ketoisovalerate and in the conversion of dihydroxymethylvalerate to ketomethylvalerate.
  • DHAD is an essential and highly conserved enzyme among plant species, showing >80% sequence similarity among even distally related plant species.
  • aspterric acid inhibits DHAD proteins in different species.
  • sequences of DHADs expressed in different species are disclosed WO2018175635 (US Patent Application Publication 20200037609), which is incorporated by reference herein in its entirety.
  • aspterric acid inhibits the activity of DHADs expressed in different species.
  • the articles “a” and “an” are used to refer to one or to more than one (i.e., to at least one) of the grammatical object of the article.
  • an element means one element or more than one element.
  • a measurable value such as an amount, a temporal duration, and the like
  • the term "about” is meant to encompass variations of ⁇ 20% or ⁇ 10%, more preferably ⁇ 5%, even more preferably ⁇ 1%, and still more preferably ⁇ 0.1% from the specified value, as such variations are appropriate to perform the disclosed methods.
  • a person of ordinary skill in the art can select the precise variation based on the context of the measurable value.
  • the terms “comprising,” “including,” “containing” and “characterized by” are exchangeable, inclusive, open-ended and do not exclude additional, unrecited elements or method steps. Any recitation herein of the term “comprising,” particularly in a description of components of a composition or in a description of elements of a device, is understood to encompass those compositions and methods consisting essentially of and consisting of the recited components or elements.
  • DHAD refers to dihydroxy acid dehydratase.
  • Other names for the enzyme are acetohydroxyacid dehydratase; a,P-dihydroxyacid dehydratase; 2,3- dihydroxyisovalerate dehydratase; a,P-dihydroxyisovalerate dehydratase; 2,3-dihydroxy-acid hydro-lyase, or EC 4.2.1.9.
  • ALS refers to acetolactate synthase.
  • Other names for the enzyme are a-acetohydroxy acid synthetase; a-acetohydroxyacid synthase; a-acetolactate synthase; a-acetolactate synthetase; acetohydroxy acid synthetase; acetohydroxyacid synthase; acetolactate pyruvate-lyase; or EC 2.2.1.6.
  • ALS inhibitor herbicide includes an ALS inhibitor herbicide or one of its environmentally compatible salts or esters.
  • Ranges throughout this disclosure, various aspects of the invention can be presented in a range format. It should be understood that the description in range format is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the invention. Accordingly, the description of a range should be considered to have specifically disclosed all the possible subranges as well as individual numerical values within that range. For example, description of a range such as from 1 to 6 should be considered to have specifically disclosed subranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6 etc., as well as individual numbers within that range, for example, 1, 2, 2.7, 3, 4, 5, 5.3, and 6. This applies regardless of the breadth of the range.
  • compositions containing a DHAD inhibitor e.g. an aspterric acid or an agriculturally acceptable derivative thereof
  • at least one acetolactate synthase (ALS) inhibitor herbicide e.g. an aspterric acid or an agriculturally acceptable derivative thereof
  • the compositions comprise a herbicidal synergistic amount of an aspterric acid or an agriculturally acceptable derivative thereof and at least one acetolactate synthase (ALS) inhibitor herbicide.
  • the compositions are used to control undesirable vegetation that is otherwise resistant to treatment with an ALS herbicide inhibitor.
  • the compositions do not contain an additional active ingredient.
  • the compositions comprise an agriculturally acceptable carrier.
  • Aspterric acid ((3R,4R,6aS,9aS)-octahydro-4-hydroxy-7-(l-methylethylidene)-lH-3,9a- methanocyclopent[c]oxocin-4-carboxylic acid), has the following structure:
  • composition of the disclosure may contain aspterric acid or an agriculturally acceptable derivative thereof.
  • the agriculturally acceptable derivative of aspterric acid is one of the aspterric derivatives disclosed in WO 2018/175635, the disclosure of which is herein incorporated in its entirety.
  • aspterric acid or agriculturally acceptable derivatives are made using methods as described in WO 2018/175635.
  • Acetolactate synthase (ALS) inhibitor herbicide ALS
  • the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • the at least one ALS inhibitor herbicide is an imidazoline. In another embodiment, the at least one ALS inhibitor herbicide is imazapyr, or an environmentally compatible salt or ester thereof.
  • the at least one ALS inhibitor is an imidazolinone such as at least one compound selected from the group consisting of: imazapyr, imazaquin, imazamethabenz- methyl, imazamox, imazapic, and imazethapyr, or environmentally compatible salts or esters thereof.
  • the at least one ALS inhibitor is a pyrimidinyl benzoate.
  • the pyrimdinyl benzoate is at least one compound selected from bispyribac-sodium and bispyribac-sodium, or environmentally compatible salts or esters thereof.
  • the at least one ALS inhibitor is a sulfonanilide comprising at least one compound selected from the group consisting of: flucarbazone- sodium and propoxycarbazone-sodium, or environmentally compatible salts or esters thereof.
  • the at least one ALS inhibitor is an a sulfonylurea comprising at least one compound selected from the group consisting of: bensulfuron-methyl, chlorimuron- ethyl, chlorsulfuron, foramsulfuron, halosulfuron-methyl, mesosulfuron-methyl, metsulfuron- methyl, nicosulfuron, primisulfuron-methyl, prosulfuron, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifl oxysulfuron-sodium, and triflusulfuron-methyl, or environmentally compatible salts or esters thereof.
  • the at least one ALS inhibitor is a triazolopyrimidine comprising at least one compound selected from the group consisting of: cloransulam-methyl, diclosulam, florasulam, flumetsulam, penoxsulam, and pyroxsulam, or environmentally compatible salts or esters thereof.
  • compositions of the disclosure may be supplemented with additional components commonly used in agrochemicals.
  • the compositions further include at least one inert liquid and/or solid carrier and, optionally, at least one surfactant, adjuvant, safener, or combination thereof.
  • compositions are directed to methods of using the compositions.
  • the disclosure provides for methods of controlling undesirable vegetation, e.g. in a field of crop plants, in a forest, in a body of water, in turf grass, around a home, etc.
  • the disclosure provides for methods of controlling undesirable vegetation in a field of crop plants, wherein the crop plants are tolerant to treatment with an herbicide.
  • the methods are used to control undesirable vegetation that is resistant to an herbicide.
  • herbicide or “herbicidal agent” refers to a substance that decrease the fitness (e.g., kills, inhibits the growth, inhibits proliferation, inhibits reproduction, inhibits spread, etc.) of undesirable vegetation.
  • composition and methods of the disclosure can include other herbicides.
  • Non-limiting examples of herbicides include: glufosinate; propaquizafop; metamitron; metazachlor; pendimethalin; flufenacet; diflufenican; clomazone; nicosulfuron; mesotrione; pinoxaden; sulcotrione; prosulfocarb; sulfentrazone; bifenox; quinmerac; triallate; terbuthylazine; atrazine; oxyfluorfen; diuron; trifluralin; chlorotoluron; benzoic acid herbicides, such as dicamba; phenoxyalkanoic acid herbicides, such as 2,4-D, MCPA and 2,4-DB; aryl oxy phenoxy propionic acid herbicides, such as clodinafop, cyhalofop, fenoxaprop, fluazifop, haloxyfop, and quizalofop;
  • herbicides are selected from the group consisting of: 2,4-D, 2,4-DB, acetochlor, acifluorfen, alachlor, ametryn, amitrole, asulam, atrazine, azafenidin, benefin, bensulfuron, bensulide, bentazon, bromacil, butylate, carfentrazone, chloramben, chlorimuron, chlorproham, chlorsulfuron, clethodim, clopyralid, cloransulam, cyanazine, cycloate, DCPA, desmedipham, dichlobenil, diclofop, diclosulam, diethatyl, difenzoquat,
  • the undesirable vegetation is resistant to an ALS inhibitor (e.g. imazapyr).
  • the vegetation is resistant to glyphosate (Roundup ®).
  • the vegetation is resistant to both an ALS inhibitor (e.g. imazapyr) and glyphosate (Roundup ®).
  • the undesirable vegetation is resistant to glufosinate.
  • the undesirable vegetation is resistant to glufosinate and glyphosate.
  • the undesirable vegetation is resistant to glufosinate and an ALS inhibitor.
  • the undesirable vegetation is resistant to glufosinate, glyphosate, and an ALS inhibitor.
  • a method for controlling undesirable vegetation in a field of crop plants which includes applying a composition of the invention to the field.
  • the composition may be applied (i) prior to planting the crop plant (for example burn-down or planting preparation) and/or (ii) after planting but before emergence of the crop plant.
  • the composition is applied to burn-down undesirable vegetation in the field such as for example prior to planting the crop.
  • the composition is applied to the field prior to planting the crop plant.
  • the composition is applied to the field at any time during an interval from about 20 days prior to planting of the crop plant to immediately prior to planting the crop plant. In other embodiments, the composition is applied to the field after planting but before emergence of the crop plant. In alternate embodiments, the composition is applied to the field at any time during an interval from about 1 day after planting of the crop plant up to, but not including emergence of the crop plant.
  • Yet another embodiment of the invention is a method of selectively controlling undesirable vegetation in a field containing undesirable vegetation and a crop plant which has tolerance to the ALS-inhibiting herbicide.
  • the method includes applying an effective amount of the composition of the disclosure to the field containing the crop plant to control the undesirable vegetation without significantly affecting the crop plant.
  • the tolerance to an ALS-inhibiting herbicide is native to the crop plant, alternatively the crop plant is genetically modified or genetically engineered to contain genetic material that confers resistance or tolerance to at least one ALS inhibitor.
  • the methods of the invention may be used with a variety of crop plants.
  • the crop plant is selected from the group consisting of soybean, cotton, com, sugar beet, peanut, rice, wheat, canola, alfalfa, sugarcane, sorghum, sunflower, and conifer crop species.
  • the conifer crop species is selected from the group consisting of Loblolly Pine (Pinus taeda) , Loblolly X Pitch Hybrid, Longleaf Pine (Pinus palustris ).
  • Shortleaf Pine Pine (Pinus echinata). Virginia Pine (Pinus virginiana), Slash Pine (Pinus elliottii), Douglas Fir (Pseudotsuga menziesii), Coastal Redwood (Sequoia sempervirens), Western Hemlock (Tsuga heterophylla), California Red Fir (Abies magnifica), California White Fir (Abies concolor) , Jack Pine (Pinus banksiana) , Lodgepole Pine (Pinus contorta), Pitch Pine (Pinus rigida) , Ponderosa Pine (Pinus ponderosa) , Sugar Pine (Pinus lambertiana), White Pine (Pinus strobus) , Black Spruce (Picea mariana) , Red Spruce (Picea rubens) , and White Spruce (Picea glauca) .
  • the undesirable vegetation includes at least one annual or perennial grass, annual or perennial broadleaf weed, vine, bramble, woody brush, or tree.
  • the undesirable vegetation are volunteer plants (e.g. seeds dropped by crops in previous years or seeds).
  • the undesirable vegetation is undesirable vegetation controlled by imazapyr.
  • the undesirable vegetation cannot be controlled by imazapyr.
  • the undesirable vegetation cannot be controlled by (e.g. is resistant to) a combination of imazapyr and Roundup®.
  • the undesirable vegetation is resistant to glufosinate.
  • the undesirable vegetation is resistant to both glufosinate and an ALS inhibitor (e.g. imazapyr).
  • the disclosure provides for methods of controlling undesirable vegetation comprising contacting undesirable vegetation with an herbicidal composition, which include a DHAD inhibitor (e.g. aspterric acid or an agriculturally acceptable derivative thereof) or an agriculturally acceptable derivative thereof, and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or ester.
  • a DHAD inhibitor e.g. aspterric acid or an agriculturally acceptable derivative thereof
  • ALS acetolactate synthase
  • the compositions for use in these methods include an herbicidal synergistic amount of the DHAD inhibitor (e.g. aspterric acid or an agriculturally acceptable derivative thereof) and the at least one ALS inhibitor herbicide and/or they control undesirable vegetation that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • the disclosure provides for methods of controlling undesirable vegetation comprising contacting undesirable vegetation with an herbicidal composition, which include an effective amount of a DHAD inhibitor (e.g. aspterric acid or an agriculturally acceptable derivative thereof) or an agriculturally acceptable derivative thereof, and an effective amount of at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or ester.
  • a DHAD inhibitor e.g. aspterric acid or an agriculturally acceptable derivative thereof
  • ALS acetolactate synthase
  • the disclosure provides for methods of controlling undesirable vegetation which decrease the amount of ALS inhibitor herbicide necessary by adding a DHAD inhibitor (e.g. aspterric acid or an agriculturally acceptable derivative thereof).
  • the disclosure is directed to methods of decreasing the amount of at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or esters necessary for controlling undesirable vegetation.
  • the methods include providing a composition comprising: aspterric acid or an agriculturally acceptable derivative thereof; and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or esters.
  • the amount of the at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or esters in the composition is less than the amount of at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or esters in a composition lacking the aspterric acid or agriculturally acceptable derivative thereof.
  • these methods are particularly useful for treating the turf of athletic fields, golf course or other conditions where lower amounts of the ALS inhibitor herbicide are desirable to provide for improved control of undesirable vegetation.
  • these methods are used when the ALS inhibitor is imazapyr.
  • the species of annual and perennial grasses controlled by imazapyr include the following (listed as common name (scientific name)): Annual bluegrass (Poa annua), Bahiagrass (Paspalum notatum), Bamyardgrass (Echinochloa crus-galli), Beardgrass (Andropogon spp.), Bermudagrass (Cynodon dactylonf), Big bluestem (Andropogon gerardii), Broadleaf signalgrass (Brachiaria platyphylla), Canada bluegrass (Poa compressa), Cattail (Typha spp.), Cheatgrass (Bromus secalinus), Cogongrass (Imperata cylindrica), Crabgrass (Digitaria spp.), Crowfootgrass (Dactyloctenium aegyptium), Dallisgrass (Paspalum dilatatum), Downy brome (Bromus tectorum), Fall panicum (Panicum dichotomif
  • the species of annual and perennial broad leaf weeds controlled by imazapyr include the following (listed as common name (scientific name)): Arrowwood (Pluchea sericea), Broom snakeweed (Gutierrezia sarothrae), Bull thistle (Cirsium vulgare), Burclover (Medicago spp.), Burdock (Arctium spp.), Camphorweed (Heterotheca subaxillaris), Canada thistle (Cirsium arvense), Carolina geranium (Geranium carolinianum), Carpetweed (Mullugo verticillata), Chickweed, mouse ear (Cerastium vulgatum), Clover (Trifolium spp.), Cocklebur (Xanthium strumarium), Common chickweed (Stellaria media), Common ragweed (Ambrosia artemisiifolia), Cudweed (Gnaphalium spp.), Dandelion (Taraxacum offic
  • Silverleaf nightshade Solanum elaeagnifolium
  • Smartweed Polygonum spp.
  • Sorrell Rall spp.
  • Sowthistle Sonchus spp.
  • Spurge annual (Euphorbia spp .)
  • Stinging nettle Urtica dioica
  • Sunflower Helianthus spp.
  • Sweet clover (Melilotus spp.).
  • Tansymustard Derivia pinnata
  • Texas thistle Cirsium texanum
  • Velvetleaf Abutilon theophrasti).
  • Western ragweed Ambrosia psilostachya), Wild carrot (Daucus carota).
  • Wild lettuce (Lactuca spp.). Wild parsnip (Pastinaca saliva), Wild turnip (Brassica campestris). Woollyleaf bursage (Ambrosia grayi), Yellow starthistle (Centaur ea solslilialis), and Yellow wood sorrel (Oxalis stricta).
  • the species of vines and brambles weeds controlled by imazapyr include the following (listed as common name (scientific name)): Field bindweed (Convolvulus arvensis). Hedge bindweed (Calystegia sequium). Honeysuckle (Lonicera spp.). Morning glory (Ipomoea spp.), Poison ivy (Rhus radicans), Redvine (Brunnichia cirrhosa), Trumpet creeper (Campsis radicans), Virginia creeper (Parthenocissus quinquefolia), Wild buckwheat (Polygonum convolvulus), Wild grape (Vitis spp.). Wild rose (Rosa sppi) including: Multiflora rose (Rosa multiflora), and Macartney rose (Rosa bracteata).
  • the species of woody brush and trees controlled by imazapyr include the following (listed as common name (scientific name)): Alder (Alnus sppi) including Red Alder (Alnus rubra), American beech (Fagus grandifolia), Ash (Fraxinus spp.), Aspen (Populus spp.), Autumn olive (Elaeagnus umbellata), Bald cypress (Taxodium distichum), Bigleaf Maple (Acer macrophyllum), Birch (Betula spp.), Black oak (Quercus kelloggii), Black gum (Nyssa sylvatica), Box elder (Acer negundo), Brazilian peppertree (Schinus terebinthifolius), Ceanothus (Ceanothus spp.), Cherry (Prunus spp.), Chinaberry (Melia azedarach), Chinese tallow-tree (Sapium sebiferum), Chi
  • Eucalyptus Eucalyptus spp.
  • Hawthorn Crataegus spp.
  • Hickory Caria spp.
  • Huckleberry Huckleberry (Gaylussacia spp.), Lyonia spp.
  • Fetterbush Locus lucida
  • Staggerbush Locus lucida
  • Madrone Albutus menziesii
  • Maple Acer spp.
  • Melaleuca Melaleuca quinquenervia
  • Mulberry Merns spp.
  • Oak Quercus spp.
  • Persimmon Deniospyros virginiana
  • Poison oak Rhus diversiloba
  • Popcom-tree Popcom-tree
  • Poplar Populus spp.
  • Privet Ligustrum vulgare
  • Red Maple Acer rubrum
  • Salt cedar Tin cedar
  • Sassafras Sassafras albidum
  • Sourwood Oxydendrum arboreum
  • Sumac Ramac
  • Sweetgum Liquidambar styraciflua
  • Sycamore Platanus occidentalis
  • Tan oak Liquidambar styraciflua
  • Floating Species of weeds controlled by imazapyr include the following (listed as common name (scientific name)): Duckweed (Lemna minor), Duckweed, Giant (Spirodela polyriza), Frogbit (Limnobium spongia), Spatterdock (Nuphar luteum ), Water Hyacinth (Eichhomia crassipes), and Water Lettuce (Pistia stratiotes).
  • Emerged Species of weeds controlled by imazapyr include the following (listed as common name (scientific name)): Alligatorweed (Alternanthera philoxeroides), Arrowhead, Duck-potato (Sagittaria spp)), Bacopa, lemon (Bacopa spp) , Parrot feather (Myriophyllum aquaticum), Pennywort (Hydrocotyle spp.), Pickerelweed (Pontederia cor data), Taro, wild; Dasheen; Elephant's Ear; Coco Yam (Colocasia esculentum), Water lily (Nymphaea odorata) , and Water primrose (Ludwigia uruguayensis).
  • Terrestrial/Marginal of weeds controlled by imazapyr include the following (listed as common name (scientific name)): Soda Apple, aquatic, Nightshade (Solanum tampicense), Bamboo, Japanese (Phyllostachys spp.), Brazilian Pepper; Christmasberry (Schinus terebinthifolius), Cattail (Typha spp.), Chinese Tallow Tree (Sapium sebiferum), Cogongrass (Imperata cylindrica) , Cordgrass, prairie (Spartina spp.), Cutgrass (Zizaniopsis miliacea) , Elephant Grass; Napier Grass (Pennisetum purpureum), Flowering rush (Butumu typla) , Giant Reed, Wild Cane (Arundo donax), Golden Bamboo (Phyllostachys aurea) , Junglerice (Echinochloa colonum), Knapweeds (Centaurea species'), Kno
  • Yet another aspect of the disclosure is methods of increasing efficacy of an ALS inhibitor herbicide.
  • the methods include mixing a DHAD inhibitor (e . g . aspterric acid or a derivative thereof) and an acetolactate synthase (ALS) inhibitor herbicide at a molar ratio in the range of 100:1 to 1 :5.
  • the methods increase the efficacy of the ALS inhibitor herbicide, relative to the efficacy observed when the ALS inhibitor herbicide is used in the absence of aspterric acid or a derivative thereof.
  • the ALS inhibitor herbicide is an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • the disclosure provides for methods of decreasing the effective amount of an ALS inhibitor herbicide for controlling undesirable vegetation.
  • the methods include mixing aspterric acid or a derivative thereof and an acetolactate synthase (ALS) inhibitor herbicide. Via use of these methods, it is possible to provide more applications of the ALS inhibitor herbicide (e.g. per acre) without exceeding approved/restricted amounts.
  • ALS acetolactate synthase
  • the ALS inhibitor herbicide is an imidazolonone comprising at least one compound selected from the group consisting of: imazapyr, imazaquin, imazamethabenz-methyl, imazamox, imazapic and imazethapyr, or environmentally compatible salts or esters thereof.
  • the ALS inhibitor herbicide is imazapyr.
  • Another embodiment is directed to the treatment of undesirable vegetation (e.g. weeds) in a field in which a percentage of the undesirable vegetation in the field is resistant to treatment with an herbicide (e.g. ALS inhibitors).
  • an herbicide e.g. ALS inhibitors
  • the percentage of undesirable vegetation in a field that is resistant to, e.g., ALS inhibitors is between 1 and 100%.
  • about 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90 or 99% of the undesirable vegetation in a field are resistant to ALS inhibitors.
  • about 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90 or 99% of the plants in a field are resistant to the ALS inhibitor (e.g. imazapyr).
  • the ALS inhibitor-resistant undesirable vegetation are weeds or volunteer plants.
  • treatment of ALS inhibitor-resistant undesirable vegetation with ALS inhibitors alone increases the growth of the ALS-inhibitor resistant undesirable vegetation.
  • treatment of ALS inhibitor-resistant undesirable vegetation with ALS inhibitors in combination with a DHAD inhibitor reduces the growth of the ALS inhibitor-resistant undesirable vegetation.
  • the ALS inhibitor and the DHAD inhibitor act synergistically in inhibiting growth of the undesirable vegetation.
  • the combination of an ALS inhibitor and a DHAD inhibitor e.g.
  • the molar ratio of the ALS inhibitor and aspterric acid in a formulation applied to the field is about 999: 1, 99: 1, 95:5, 90: 10, 85: 15, 80:20, 75:25, 70:30, 65:35, 60:40, 55:45, 50:50, 45:55, 40:60, 35: 65, 30:70, 25:75, 20:80, 15:85, 10:90, 5:95, 1 :99 or 1 :999, or ranges therebetween.
  • all undesirable vegetation regardless of whether they are ALS inhibitor-susceptible or ALS inhibitor-resistant are inhibited by the combination of an ALS inhibitor and a DHAD inhibitor (e.g. aspterric acid or a agriculturally acceptable derivative thereof).
  • a DHAD inhibitor e.g. aspterric acid or a agriculturally acceptable derivative thereof.
  • compositions as described herein may be formulated as a formulation type described in “Catalogue of Pesticide Formulation Types and International Coding System” Technical Monograph n° 2, 5th Edition by CropLife International (2002), which is incorporated by reference in its entirety.
  • This Example describes in detail the plate assay protocols used in the other examples. a) Preparing, plating, and germinating seeds q/'Aradiposis thaliana test plants
  • Seeds of Arabidopsis thaliana were sterilized in an appropriate container, for example a microfuge tube, in two steps.
  • the seeds were suspended in 70% ethanol by vortexing and then the seeds in suspension were allowed to settle (approximately 30 seconds) and the liquid was removed and discarded.
  • the seed pellet was suspended in a solution of 20% bleach and 0.01% triton by agitating the tube contents on a on rocker at room temperature for 10 minutes. The seeds were then allowed to settle, and the liquid was removed and discarded.
  • the seed pellet was then triple washed with water. After washing, water is added to the seed pellet to cover seeds. The seeds are incubated at 4°C for 2 days. After two days, the tubes of seeds were removed from 4°C and plated on pre-prepared 100mm petri dishes containing IX MS media (0.75% sucrose, 0.7% agar).
  • the seed-containing plates were germinated in a Pervical incubator with the following settings for 4 days: 23°C day, 16-hour light and 170 lux light intensity, 21°C night no light 8 hours. b) Evaluation of herbicide activity on seedling
  • Material preparation begins with melting 1.4% agar in a microwave and keeping it warm in 68°C bead bath.
  • the 2X treatment solutions are then prepared by adding 2 times the desired amount of herbicide stock (or active) to 2X liquid MS media.
  • the following are then transferred into a BSC: 48 well plates (48WP); sterile glass beaker (250mL); repeat pipettor; molten agar; and 2X treatment solutions.
  • 48WP 48 well plates
  • sterile glass beaker 250mL
  • repeat pipettor molten agar
  • 2X treatment solutions ii. Pouring Plates:
  • Example 2 Determining the efficacy of aspterric acid and ALS inhibitor herbicide
  • FIG. 3 shows that aspterric acid inhibited the growth of both an ALS-inhibitor susceptible strain (Col-0) and an ALS-inhibitor resistant strain (Csrl-2, resistant to Imazapyr).
  • Example 3 Efficacy of aspterric acid and imazapyr in weed controls
  • This example shows the results of testing the efficacy of aspterric and imazapyr in weed controls. Treatments tested were 0, 10, 30 and 50 nM of aspterric acid and 0, 1, 5, 10, 30 and 50 nM of imazapyr in an Arabidopsis strain col-0 that is sensitive to ALS inhibitors, using the protocols described in Example 1. Results are shown in FIG. 5 A and 5B (repeat experiments).
  • Example 4 Efficacy of aspterric acid and imazapyr in weeds resistant to imazapyr
  • FIG. 6A-6B show the results of Barnyard grass and Palmer Amaranth, respectively, four days post-spray after herbicide treatment.
  • imazapyr 1% of the commercially available formulation Ecomazapyr in water
  • FIG. 7A-7B show the results of Arabidopsis Col-0 and Arabidopsis csrl-2 plants, four days post-spray.
  • FIG. 8A-8B show the results of Barnyard grass treated imazapyr and aspterric acid combinations, seven days post-treatment.
  • FIG. 8 A Ima: 2 mL imazapyr (1% in water); Ima+ AA: combination of 1 ml of 1% imazapyr and 1 ml of aspterric acid (comprising 100 ⁇ M in 5mM MES and 0.05% silwet, pH 5.5); Water: 2 mL water.
  • FIG. 8B Barnyard grass treated first with imazapyr and then aspterric acid or with the combination of imazapyr and aspterric acid.
  • Ima-> AA sprayed 1 mL imazapyr (1% in water) followed by spraying 1 mL aspterric acid (100 ⁇ M in 5mM MES and 0.05% silwet, pH 5.5); Ima+ AA: 2 mL combined imazapyr and aspterric Acid solution.
  • aspterric acid does not hinder imazapyr performance.
  • imazapyr + aspterric acid can be used together.
  • Embodiment 1 A herbicidal composition comprising: a dihydroxy acid dehydratase (DHAD) inhibitor; and at least one acetolactate synthase (ALS) inhibitor herbicide or one of its environmentally compatible salts or ester, wherein the composition comprises a herbicidal synergistic ratio of the DHAD inhibitor and the at least one ALS inhibitor herbicide or wherein the composition controls undesirable vegetation that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • DHAD dihydroxy acid dehydratase
  • ALS acetolactate synthase
  • Embodiment 2 The herbicidal composition of Embodiment 1, wherein the DHAD inhibitor is aspterric acid or an agriculturally acceptable derivative thereof.
  • Embodiment 3 The herbicidal composition of Embodiments 1 or 2, wherein the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • Embodiment 4 The herbicidal composition of Embodiment 3, wherein the at least one ALS inhibitor herbicide is an imidazolinone.
  • Embodiment 5 The herbicidal composition of Embodiment 4, wherein the imidazolinone comprises at least one compound selected from the group consisting of imazapyr, imazaquin, imazamethabenz- methyl, imazamox, imazapic and imazethapyr, or an environmentally compatible salt or ester thereof.
  • Embodiment 6 The herbicidal composition of Embodiment 3 or 4, wherein the at least one ALS inhibitor herbicide is imazapyr.
  • Embodiment 7 The herbicidal composition of any one of Embodiments 1-6, wherein the DHAD inhibitor and the at least one ALS inhibitor herbicide are present at a molar ratio in the range of about 100: 1 to about 1 :5.
  • Embodiment 8 The herbicidal composition of Embodiment 6, wherein the DHAD inhibitor and the at least one ALS inhibitor herbicide are present at a molar ratio in the range of about 100: 1 to about 1 :2.
  • Embodiment 9 The herbicidal composition of any one of Embodiments 1-8 further comprising at least one inert liquid and/or solid carrier.
  • Embodiment 10 The herbicidal composition of Embodiment 9 further comprising at least one surfactant, adjuvant, safener, or combination thereof.
  • Embodiment 11 The herbicidal composition of any one of Embodiments 1-10, wherein the composition controls undesirable vegetation that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • Embodiment 12 The herbicidal composition of any one of Embodiments 1-11, wherein the compositions comprises a herbicidal synergistic ratio of the DHAD inhibitor and the at least one ALS inhibitor herbicide.
  • Embodiment 13 The herbicidal composition of any one of Embodiments 1-12, wherein the composition does not comprise an additional herbicidally active ingredient.
  • Embodiment 14 A method for controlling undesirable vegetation in a field of crop plants, the method comprising applying the herbicidal composition of any one of Embodiments 1-13 to the field (i) prior to planting the crop plant or (ii) after planting and prior to emergence of the crop plant.
  • Embodiment 15 A method for controlling undesirable vegetation in a field of crop plants, the method comprising applying the herbicidal composition to the field (i) prior to planting the crop plant or (ii) after planting and prior to emergence of the crop plant, wherein the herbicidal composition comprisesa DHAD inhibitor; and at least one ALS inhibitor herbicide or one of its environmentally compatible salts or ester, wherein the undesirable vegetation comprises one or more plant that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • Embodiment 16 The method of Embodiment 15, wherein the DHAD inhibitor is an aspterric acid or an agriculturally acceptable derivative thereof.
  • Embodiment 17 The method of Embodiment 15 or 16, wherein the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • Embodiment 18 The method of Embodiment 17, wherein the at least one ALS inhibitor herbicide is an imidazolinone.
  • Embodiment 19 The method of Embodiment 18, wherein the imidazolinone comprises at least one compound selected from the group consisting of: imazapyr, imazaquin, imazamethabenz-methyl, imazamox, imazapic and imazethapyr, or an environmentally compatible salt or ester thereof.
  • Embodiment 20 The method of Embodiment 17 or 18, wherein the at least one ALS inhibitor herbicide is imazapyr.
  • Embodiment 21 The method of Embodiment 20, wherein the undesirable vegetation comprises one or more plants that are otherwise resistant of imazapyr and/or to a mixture comprising imazapyr and glyphosate.
  • Embodiment 22 The method of any one of Embodiments 14-21, wherein the herbicidal composition is applied to the field prior to planting the crop plant.
  • Embodiment 23 The method of Embodiment 22, wherein the herbicidal composition is applied to the field at any time during an interval from about 20 days prior to planting of the crop plant to immediately prior to planting the crop plant.
  • Embodiment 24 The method of any one of Embodiments 14-21, wherein the composition is applied to the field after planting and prior to emergence of the crop plant.
  • Embodiment 25 The method of any one of Embodiments 14-21 wherein the composition is applied to the field at any time during an interval from about 1 day after planting of the crop plant up to, but not including, emergence of the crop plant.
  • Embodiment 26 A method of controlling undesirable vegetation in a field comprising undesirable vegetation and a crop plant, wherein the crop plant has tolerance to an ALS inhibitor herbicide, the method comprising applying an effective amount of the herbicidal composition of any one of paragraphs 1-13 to the field containing the crop plant to control the undesirable vegetation without significantly affecting the crop plant.
  • Embodiment 27 The method of Embodiment 26, wherein the method selectively controls undesirable vegetation.
  • Embodiment 28 The method of Embodiment 25 or 26, wherein the crop plant has tolerance to ALS- inhibiting herbicide in the herbicidal composition.
  • Embodiment 29 The method of Embodiment 28, wherein the ALS-inhibiting herbicide is imazapyr.
  • Embodiment 30 The method of any one of Embodiments 26-29, wherein the tolerance to the ALS-inhibiting herbicide is native to the crop plant.
  • Embodiment 31 The method of any one of Embodiments 26-30, wherein the crop plant is genetically modified or genetically engineered to contain genetic material that confers resistance or tolerance to at least one ALS inhibiting herbicide.
  • Embodiment 32 The method of any one of Embodiments 14-31, wherein the crop plant is selected from the group consisting of soybean, cotton, corn, sugar beet, peanut, rice, wheat, canola, alfalfa, sugarcane, sorghum, sunflower, and conifer crop species.
  • Embodiment 33 The method of Embodiment 32, wherein the conifer crop species is selected from the group consisting of Loblolly Pine (Pinus taedci). Loblolly X Pitch Hybrid, Longleaf Pine (Pinus palustris). Shortleaf Pine (Pinus echinata). Virginia Pine (Pinus virginiana), Slash Pine (Pinus elliottii), Douglas Fir (Pseudotsuga menziesii). Coastal Redwood (Sequoia sempervirens), Western Hemlock (Tsuga heterophylla), California Red Fir (Abies magnifica). California White Fir (Abies concolor). Jack Pine (Pinus banksiana).
  • Loblolly Pine Loblolly X Pitch Hybrid, Longleaf Pine (Pinus palustris). Shortleaf Pine (Pinus echinata). Virginia Pine (Pinus virginiana), Slash Pine (Pinus elliottii), Douglas Fi
  • Embodiment 34 The method of any one of Embodiments 14-27, wherein the undesirable vegetation is resistant to an ALS inhibitor herbicide.
  • Embodiment 35 The method of any one of Embodiments 14-34, wherein the undesirable vegetation includes at least one annual or perennial grass, annual or perennial broadleaf weed, vine, bramble, woody brush, or tree.
  • Embodiment 36 A method of improving efficacy of an ALS inhibitor herbicide against undesirable vegetation comprising plants resistant to the ALS inhibitor herbicide comprising mixing a DHAD inhibitor and at least one ALS inhibitor herbicide or one of its environmentally compatible salts or ester, wherein the efficacy of the ALS inhibitor herbicide is increased relative to the efficacy observed when the ALS inhibitor herbicide is used in the absence of the DHAD inhibitor.
  • Embodiment 37 A method of improving efficacy of an ALS inhibitor herbicide comprising a DHAD inhibitor and at least one ALS inhibitor herbicide or one of its environmentally compatible salts or ester at a molar ratio in the range of 100: 1 to 1 : 5, wherein the efficacy of the ALS inhibitor herbicide is increased relative to the efficacy observed when the ALS inhibitor herbicide is used in the absence of the DHAD inhibitor.
  • Embodiment 38 The method of Embodiment 36 or 37, wherein the DHAD inhibitor is aspterric acid or an agriculturally acceptable derivative thereof.
  • Embodiment 39 The method of any one of Embodiment 36 or 37, wherein the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • Embodiment 40 The method of Embodiment 39, wherein the at least one ALS inhibitor herbicide is an imidazolinone.
  • Embodiment 41 The method of Embodiment 40, wherein the imidazolinone comprises at least one compound selected from the group consisting of: imazapyr, imazaquin, imazamethabenz-methyl, imazamox, imazapic and imazethapyr, or an environmentally compatible salt or ester thereof.
  • Embodiment 42 The method of Embodiment 40 or 41, wherein the at least one ALS inhibitor herbicide is imazapyr.
  • Embodiment 43 A method of controlling undesirable vegetation comprising contacting undesirable vegetation with an herbicidal composition comprising: a DHAD inhibitor; and at least one ALS inhibitor herbicide or one of its environmentally compatible salts or ester, wherein the composition comprises an herbicidal synergistic ratio of the DHAD inhibitor and the at least one ALS inhibitor herbicide or wherein the composition controls undesirable vegetation that is otherwise resistant to the at least one ALS inhibitor herbicide.
  • Embodiment 44 The method of Embodiment 43, wherein the DHAD inhibitor is aspterric acid or an agriculturally acceptable derivative thereof.
  • Embodiment 45 The method of Embodiment 43, wherein the at least one ALS inhibitor herbicide is selected from the group consisting of an imidazolinone, a pyrimidinyl benzoate, a sulfonanilide, a sulfonylurea, a triazolopyrimidine, and combinations thereof.
  • Embodiment 46 The method of Embodiment 43, wherein the at least one ALS inhibitor herbicide is an imidazolinone.
  • Embodiment 47 The method of Embodiment 46, wherein the imidazolinone comprises at least one compound selected from the group consisting of: imazapyr, imazaquin, imazamethabenz-methyl, imazamox, imazapic and imazethapyr, or an environmentally compatible salt or ester thereof.
  • Embodiment 48 The method of Embodiment 45 or 46, wherein the at least one ALS inhibitor herbicide is imazapyr.

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Abstract

La présente divulgation concerne des compositions herbicides, des formulations et leur utilisation dans la régulation ou l'inhibition de la croissance des plantes. En particulier, les compositions herbicides et les formulations de la présente invention comprennent un inhibiteur de dihydroxy acide déhydratase (DHAD) (par exemple acide asptérique ou dérivé acceptable de celui-ci tel que présentement défini), en combinaison avec au moins un herbicide qui est un inhibiteur d'acétolactate synthase.
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