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WO2025006659A1 - Mélanges de bixlozone avec déflecteurs d'électrons du photosystème i - Google Patents

Mélanges de bixlozone avec déflecteurs d'électrons du photosystème i Download PDF

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Publication number
WO2025006659A1
WO2025006659A1 PCT/US2024/035696 US2024035696W WO2025006659A1 WO 2025006659 A1 WO2025006659 A1 WO 2025006659A1 US 2024035696 W US2024035696 W US 2024035696W WO 2025006659 A1 WO2025006659 A1 WO 2025006659A1
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WO
WIPO (PCT)
Prior art keywords
mixture
diquat
bixlozone
active
isoflex
Prior art date
Application number
PCT/US2024/035696
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English (en)
Inventor
David HENNENS
Ana Paula MEIRELLES MENZANI
Murilo VILLAS BOAS BAGATTA
Stephen Pettenon
Original Assignee
Fmc Corporation
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Publication of WO2025006659A1 publication Critical patent/WO2025006659A1/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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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 invention relates to a herbicidal mixture of bixlozone with one or more photosystem I electron diverters and salts or esters thereof and methods of their use for controlling undesirable vegetation.
  • United States Patent 4,405,357 discloses certain 3-isoxazolidinones which exhibit desirable selective activity and are shown to be effective in controlling grassy and broadleaf weed species.
  • 2-[(2,4- dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone CA No. 81777-95-9.
  • a mixture including 2-[(2,4-dichlorophenyl)methyl]-4.4-dimethyl-3-isoxazolidinone, along with several other active ingredients is taught in WO2015/127259.
  • This invention is directed to a mixture comprising bixlozone and at least one herbicide selected from photosystem I electron diverters and agriculturally acceptable salts and esters thereof.
  • this invention is directed to an agrochemical composition comprising bixlozone and at least one herbicide selected from photosystem I electron diverter wherein the bixlozone and photosystem I electron diverter are present in synergistically effective amounts.
  • This invention is also directed to a method of controlling undesired vegetation comprising applying a herbicidally effective amount of a mixture comprising bixlozone and at least one herbicide selected from a photosystem I electron diverter to the locus of the undesired vegetation.
  • This invention also includes a herbicidal mixture comprising (a) a mixture as described above, and further comprising (b) at least one additional active ingredient selected from (bl) through (bl 5); and salts of compounds of (bl) through (b 15), as described below.
  • the terms “comprises,’' “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover anon-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’.
  • seedling used either alone or in a combination of words means a young plant developing from the embry o of a seed.
  • narrowleaf used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to descnbe a group of angiosperms characterized by embryos having two cotyledons.
  • bixlozone is synonymous with “2,4-DC” which describes 2— [(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone.
  • Bixlozone is provided available under the tradename “IsoflexTM Active” and is found in some markets as a formulated product under the trade name “Overwatch®”.
  • Photosystem I electron diverters are chemical compounds that accept electrons from Photosy stem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty 7 acids and chlorophyll.
  • Photosystem I electron diverters are classified in the HRAC Mode Of Action Group 22 and are ty pically used in non-selective foliar knockdown applications. Examples of photosystem I electron diverters include cyperquat, diquat, morfamquat and paraquat, and salts thereof. It has now been identified that field populations of Lolium multiflorum and Urochloa decumbens that are resistant photosystem I electon diverters are controlled by a mixture of bixlozone and at least one photosystem I electon diverter.
  • a mixture of bixlozone with at least one photosystem 1 electon diverter is synergistic and able to overcome the resistance to the Group 22 herbicides.
  • the unexpected element is that the activity of bixlozone is mainly by uptake via the roots and shoots (residual efficacy) and therefore less efficacy is expected on already established weeds.
  • a mixture of diquat and paraquat is provided by Spray. Seed® 250 as a soluble concentrate (SL) liquid formulation containing the equivalent of 135 g/L paraquat and 115 g/L diquat.
  • salts of photosystem I electron diverters can be found in equilibrium with their corresponding nonsalt forms, salts share the biological utility 7 of the nonsalt forms.
  • the salts of a mixture of the invention 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.
  • Salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises photosystem I electron diverters and agriculturally suitable salts thereof.
  • Embodiment Al The mixture as described in the Summary of the Invention.
  • Embodiment A2 The mixture as descried in Embodiment Al wherein the photosystem I electron diverter is selected from cyperquat, diquat, diquat dibromide, morfamquat and paraquat or combinations thereof.
  • Embodiment A3 The mixture as described in Embodiment A2 wherein the photosystem I electron diverter is selected from diquat and paraquat or combinations thereof.
  • Embodiment Bl The mixture of any of Embodiments A2 to A3 wherein the photosystem I electron diverter is a combination of diquat and paraquat.
  • Embodiment B2 The mixture of Embodiment Bl wherein the diquat is provided at 135 g/L and the paraquat is provided at 115 g/L.
  • Embodiment B3 The mixture of Embodiment B2 wherein the diquat is provided at 135 g/L and the paraquat is provided at 115 g/L in a soluble concentrate (SL) formulation.
  • SL soluble concentrate
  • Embodiment B4 The mixture of any one of Embodiments Bl through B3 wherein the diquat and paraquat are provided by Spray. Seed® 250 herbicide.
  • Embodiment CL The mixture as described in any of Embodiments Al through A3 wherein the mixture comprises bixlozone and diquat.
  • Embodiment C2 The mixture as described in Embodiment Cl wherein the mixture is synergistic.
  • Embodiment C3 The mixture of Embodiment C2 wherein the synergistic effect is observed on Urocloa spp. Or Lolium spp.. Embodiment C4. The mixture as described in Embodiment C3 wherein the synergistic effect is observed on Urocloa decumbens (BRADC) or Lolium multiflorum (LOLMU).
  • BRADC Urocloa decumbens
  • LELMU Lolium multiflorum
  • Embodiment C5. The mixture as described in Embodiment C4 wherein the synergistic effect is observed on Urocloa decumbens (BRADC).
  • Embodiment C6 The mixture as described in Embodiment C5 wherein the synergistic effect is observed on Lolium multiflorum (LOLMU).
  • LLOLMU Lolium multiflorum
  • Embodiment C7 The mixture as described in Embodiment C4 wherein the synergistic effect is observed on Lolium rigidum (LOLRI).
  • LLOLRI Lolium rigidum
  • Embodiment C8 The mixture as described in any one of Embodiments Cl through C7 wherein the ratio of bixlozone to diquat is from about 1.5 : 1 to about 3 : 2.
  • Embodiment C9 The mixture as described in Embodiment C8 wherein the ratio of bixlozone to diquat is about 1.5 : 1.
  • Embodiment CIO The mixture as described in Embodiment C8 wherein the ratio of bixlozone to diquat is about 3 : 2.
  • Embodiment Cl 1 The mixture as described in any one of Embodiment Cl through C7 wherein the ratio of bixlozone to diquat is from about 3 : 2 to about 7.2 : 5.
  • Embodiment Cl 2.
  • Embodiment Cl 3 The mixture as described in Embodiment C12 wherein the ratio of bixlozone to diquat is about 7.2 : 5.
  • Embodiment Cl 4 The mixture as described in any of Embodiments Cl to Cl 3 wherein the application rate of bixlozone is from about 100 to about 700 g/ha (grams per hectare).
  • Embodiment Cl 5 The mixture as described in Embodiment C14 wherein the application rate of bixlozone is from about 125 to about 650 g/ha.
  • Embodiment Cl 6 The mixture of Embodiment C 15 wherein the application rate of bixlozone is from about 150 to about 600 g/ha.
  • Embodiment C 17 The mixture of Embodiment C 16 wherein the application rate of bixlozone is from about 150 to about 400 g/ha.
  • Embodiment C 18 The mixture of Embodiment C 17 wherein the application rate of bixlozone is from about 150 to about 300 g/ha.
  • Embodiment Cl 9 The mixture of Embodiment C18 wherein the application rate of bixlozone is from about 150 to about 200 g/ha.
  • Embodiment C20 The mixture of any one of Embodiments Cl through C19 wherein the mixture further comprises mineral oil.
  • Embodiment DI The mixture as described in any of Embodiments Al through A3 wherein the mixture comprises bixlozone and paraquat.
  • Embodiment D2 The mixture as described in Embodiment DI wherein the mixture is synergistic.
  • Embodiment D3 The mixture as described in Embodiment DI or D2 wherein the synergistic effect is observed on ryegrass (3RYGC).
  • Embodiment D4 The mixture as described in Embodiment D3 wherein the synergistic effect is observed on wild-type ryegrass or paraquat-resistant ryegrass.
  • Embodiment D5 The mixture as described in any one of Embodiments DI through D5 wherein the ratio of bixlozone to paraquat is from about 2.5 : 1 to about 1 : 1.
  • Embodiment D6 The mixture as described in Embodiment D5 wherein the ratio of bixlozone to paraquat is about 2 : 1.
  • Embodiment D7 The mixture as described in any one of Embodiments DI through D6 wherein the application rate of bixlozone in from about 100 to about 700 g/ha.
  • Embodiment D8 The mixture of Embodiment D7 wherein the application rate of bixlozone is from about 250 to about 600 g/ha.
  • Embodiment D9 The mixture of Embodiment D8 wherein the application rate of bixlozone is from about 350 to about 550 g/ha.
  • Embodiment D10 The mixture of Embodiment 26B wherein the application rate of bixlozone is from about 450 to about 550 g/ha.
  • Embodiment Dl l The mixture of Embodiment 26B wherein the application rate of bixlozone is about 500 g/ha.
  • Embodiment El The mixture of any one of Embodiments Al through A3 or Bl through B5 or C 1 through C20 or D 1 through D 11 wherein the mixture further comprises a third active ingredient.
  • Embodiment E2 The mixture of any one of Embodiments Al through A3 or Bl through B5 or C 1 through C20 or D 1 through D 11 wherein the mixture is in a form selected from a suspension concentrate, a capsule suspension, an emulsifiable concentrate, granules and wettable granules, and combinations thereof.
  • Embodiment Fl. A method of making the mixture as described in any one of Embodiments Al through A3, or Bl through B5, or Cl through C20, or DI through Dl l, or El through E2.
  • Embodiment G1 A method of using the mixture as described in any of one of Embodiments Al through A3, or Bl through B5, or Cl through C20, or DI through Dl l, or prepared as described in Embodiment Fl comprising the steps of applying a herbicidally effective amount of the mixture to the locus of an undesirable plant.
  • Embodiment G2 The method of Embodiment G1 wherein the method comprises applying an agrochemical composition of bixlozone, paraquat and diquat for preplant bumdown.
  • Embodiment G3 The method of Embodiment G1 wherein the method comprises applying an agrochemical composition of i) bixlozone and paraquat; or ii) bixlozone and diquat for pre-plant burndow n.
  • Embodiments of this invention including Embodiments Al through A3, or Bl through B5, or Cl through C20, or DI through Dl l, or prepared as described in Embodiment Fl, or used as described in Embodiments G1 through G3 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 mixtures but also the methods of using the mixtures.
  • embodiments of this invention including Embodiments Al through A3, or Bl through B5, or Cl through C20, or DI through DI 1, or prepared as described in Embodiment Fl, or used as described in Embodiments G1 through G3 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions of the mixtures and methods of using the compositions of the present invention.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the mixtures of the invention (e.g., as a composition described herein).
  • the mixtures of the invention e.g., as a composition described herein.
  • Mixtures of the invention are particularly useful for selective control of weeds selected from the group consisting of annual blue grass, annual ryegrass (Lolium rigidum), ball medic (Medicago spp.), barley grass (Hordeum murinum), bedstraw (Galium tricornutum), Benghal dayflower, bifora (Bifora testiculatd), black grass, black night shade, broadleaf signal grass, brome grass (Bromus spp.), Canada thistle, capeweed (Arctotheca calendula), cheat, chickweed (Stellaria media), common cocklebur (Xanthium pensylvanicum), common ragweed, com poppies, doublegee (Emex australis), field violet, fleabane (Conyza bonariensis) giant foxtail, fumitory' (Fumaria spp), goose grass, green fox tail, guinea grass, hairy beggarticks, herbicide-resistant black grass, horseweed, Indian
  • wild oat (Avena fatua), wild pointsettia, wild radish (Raphanus raphanistrum). wild turnip (Rapistrum rugosum, Brassica tournamentfortii). wireweed (Polygonum aviculare), yellow foxtail, yellow nutsedge (Cyperus esculentus) in crops such as bananas, barley, beans, beets, cassava, cereals, citrus, cocoas, coconuts, coffee, com, grapes, groundnuts, hops, oil palm, oilseed rape, peas, peanuts, potato, rice, sugar cane, sunflower, tea, tobacco, turf and wheat.
  • crops such as bananas, barley, beans, beets, cassava, cereals, citrus, cocoas, coconuts, coffee, com, grapes, groundnuts, hops, oil palm, oilseed rape, peas, peanuts, potato, rice, sugar cane, sunflower, tea, tobacco, turf and wheat.
  • herbicidal compositions of the present invention comprising the mixtures of embodiments described above.
  • the mixtures the invention can be prepared by general methods known in the art.
  • a compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • a composition i.e. formulation
  • additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil ty pe, moisture and temperature.
  • Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in -water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels.
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from filmforming solutions or flowable suspensions are particularly useful for seed treatment.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient.
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
  • Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Typical solid diluents are described in Watkins et ⁇ .. Handbook of Insecticide Dust Diluents and Carriers, 2 nd Ed., Dorland Books. Caldwell, New Jersey.
  • Liquid diluents include, for example, water.
  • MA-dimethylalkanamides e.g., M/V-dimelhyl formamide
  • limonene dimethyl sulfoxide
  • A-alkylpyrrolidones e.g., JV-methylpyrrolidinone
  • alkyl phosphates e.g., triethyl phosphate
  • paraffins e.g., white mineral oils, normal paraffins, isoparaffins
  • alkylbenzenes alkydnaphthalenes, glycerine, glycerol triacetate
  • sorbitol aromatic hydrocarbons, dearomatized aliphatics, alkydbenzenes, alkydnaphthalenes, ketones such as
  • Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C 6 -C 22 ), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, com (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof.
  • plant seed and fruit oils e.g., oils of olive, castor, linseed, sesame, com (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
  • animal-sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
  • Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
  • alkylated fatty acids e.g., methylated, ethylated, butylated
  • Typical liquid diluents are described in Marsden, Solvents Guide, 2 nd Ed., Interscience, New York, 1950.
  • the solid and liquid compositions of the present invention often include one or more surfactants.
  • surfactants also known as ‘'surface-active agents”
  • 'surface-active agents generally modify, most often reduce, the surface tension of the liquid.
  • surfactants can be useful as w etting agents, dispersants, emulsifiers or defoaming agents.
  • Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene
  • Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
  • Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as JV-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary’ ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquatemary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
  • amines such as JV-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxyl
  • compositions with nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants are also useful for the present mixtures.
  • Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety' of published references including McCutcheon ’s Emulsifiers and Detergents, annual American and International Editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
  • compositions of this invention may also contain formulation auxiliaries and additives, know n to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
  • formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes.
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon ’s Volume 2: Functioned Materials, annual International and North American editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the mixture of the invention and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry 7 diluent.
  • Solutions, including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water.
  • Active ingredient slurries, with particle diameters of up to 2,000 pm can be wet milled using media mills to obtain particles with average diameters below 3 pm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S.
  • Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill).
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”’, Chemical Engineering, December 4, 1967, pp 147-48, Perry ’s Chemical Engineer 's Handbook, 4 th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546.
  • Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Mixture A, B, C, D, E or F 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%
  • Emulsion in Water Mixture A, B, C, D, E or F 10.0% butyl polyoxyethylene/polypropylene block copolymer 4.0% stearic acid/poly ethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1% l,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0
  • Oil Dispersion Mixture A, B, C, D, E or F 25% polyoxyethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5%
  • the mixtures of the inention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil).
  • postemergence weed control i.e. applied after weed seedlings emerge from the soil
  • preemergence weed control i.e. applied before weed seedlings emerge from the soil.
  • Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures.
  • Mixtures of this invention by virtue of selective metabolism in crops versus weeds, or by selective activity' at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture.
  • selectivity factors within a mixture or group of mixtures can readily be determined by performing routine biological and/or biochemical assays.
  • Mixtures of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, com (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
  • important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, com (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, coco
  • Mixtures of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all mixtures are equally effective against all weeds.
  • the mixtures of the invention have both preemergent and postemergent herbicidal activity 7 , to control undesired vegetation by killing or injuring the vegetation or reducing its growth
  • the mixtures can be usefully applied by a variety 7 of methods involving contacting a herbicidally effective amount of a mixture of the invention, or a composition comprising said mixture and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
  • a herbicidally effective amount of the mixtures of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of mixtures of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • a mixture of the invention is applied, typically in a formulated composition, to a locus comprising desired vegetation (e.g., crops) and undesired vegetation (i.e. weeds), both of which may be seeds, seedlings and/or larger plants, in contact with a growth medium (e.g.. soil).
  • desired vegetation e.g., crops
  • undesired vegetation i.e. weeds
  • a growth medium e.g. soil
  • a composition comprising a mixture of the invention can be directly applied to a plant or a part thereof, particularly of the undesired vegetation, and/or to the growth medium in contact with the plant.
  • Plant varieties and cultivars of the desired vegetation in the locus treated with a mixture of the invention can be obtained by conventional propagation and breeding methods or by genetic engineering methods.
  • Genetically modified plants are those in which a heterologous gene (transgene) has been stably integrated into the plant’s genome.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • mixtures of the invention are used to control undesired vegetation
  • contact of desired vegetation in the treated locus with mixtures of the invention may result in super-additive or synergistic effects with genetic traits in the desired vegetation, including traits incorporated through genetic modification.
  • traits incorporated through genetic modification For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic/abiotic stresses or storage stability may be greater than expected from the genetic traits in the desired vegetation.
  • Mixtures of this invention can also be mixed with one or more other biologically active mixtures or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active mixtures or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • Mixtures of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes.
  • the present invention also pertains to a composition
  • a composition comprising a mixture of the invention (in a herbicidally effective amount) and at least one additional biologically active mixture or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent.
  • the other biologically active mixtures or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent.
  • one or more other biologically active mixtures or agents can be formulated together with a mixture of the invention, to form a premix, or one or more other biologically active mixtures or agents can be formulated separately from the mixture of the invention, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
  • a mixture of one or more of the following herbicides with a mixture of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal). alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, bixlozone, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon,
  • dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimesulfazet, dimepiperate, dimethachlor.
  • indanofan indaziflam, indolauxipyr, indolauxipyr-cyanomethyl, indolauxipyr-propargyl, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone.
  • iptriazopyrid isoproturon, isouron.
  • oxadiazon oxasulfuron.
  • oxaziclomefone oxyfluorfen, paraquat dichloride, pebulate.
  • pelargonic acid pendimethalin, penoxsulam.
  • pentanochlor pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham.
  • picloram picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxy carbazone, propyrisulfuron, propyzamide.
  • prosulfocarb prosulfuron, pyraclonil, pyraflufen-ethyl, pyraquinate, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, siduron,
  • herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • Mixtures of this invention can also be used in combination with plant growth regulators such as aviglycine.
  • plant growth regulators such as aviglycine.
  • the mixing partners are typically used in the amounts similar to amounts customary when the mixture partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between one-half and the full application rate specified on product labels for use of active ingredient alone. These amounts are listed in references such as The Pesticide Manual and The BioPesticide Manucd.
  • the weight ratio of these various mixing partners (in total) to the mixture of the invention is typically between about 1 : 3000 and about 3000: 1. Of note are weight ratios between about 1 :300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1 ).
  • One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the mixture of the invention alone.
  • combinations of a mixture of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable.
  • synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.
  • safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
  • a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
  • Mixtures of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N- (aminocarbonyl)-2-methylbenzenesulfonamide, A-(aminocarbonyl)-
  • herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron,
  • Antidotally effective amounts of the herbicide safeners can be applied at the same time as the mixtures of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising mixture of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the grow th of undesired vegetation in a crop comprising contacting the locus of the crop with aherbicidally effective amount of a mixture of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
  • Mixtures of the invention can also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect.
  • composition comprising a mixture of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  • additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount)
  • at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents are mixtures of this invention with an additionoal herbicide.
  • Table Al lists specific combinations of a Component (a) further comprising Component (b) illustrative of the mixtures, compositions and methods of the present invention where Component (a) refers to a mixture as described in the Summary of the Invention.
  • the second column of Table Al lists the specific Component (b) compound (e.g., ‘‘2,4-D” in the first line).
  • the third, fourth and fifth columns of Table Al lists ranges of weight ratios for rates at which the Component (a) mixture is typically applied to a field-grown crop relative to Component (b) (i.e. (a): (b)).
  • the first line of Table Al specifically discloses the combination of Component (a) (i.e. a mixture of bixlozone and a photosystem 1 electron diverter) with 2,4-D is typically applied in a weight ratio between 1: 192 - 6: 1.
  • the remaining lines of Table Al are to be construed similarly.
  • Table A2 is constructed the same as Table Al above except that entries below the ⁇ ‘Component (a)’’ column heading are replaced with the respective Component (a) Column Entry shown below.
  • Mixture # in the Component (a) column is identified in Index Table A.
  • Table A2 the entnes below the “Component (a)” column heading all recite “Mixture #” (i.e. Mixture # identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Mixture # with 2.4-D.
  • Tables A3 through A4 are constructed similarly.
  • Preferred for better control of undesired vegetation e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety
  • a herbicide selected from the group consisting of chlorimuron-ethyl, clomazone, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tetflupyrolimet, tribenuron, pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, rimisoxafen, metolachlor and S- metolachlor.
  • a 400 g/L SC formulation of IsoflexTM Active was prepared (bixlozone 35.87%, water 53.7%) that included a liquid diluent, an anionic surfactant, a thickener, a silicone defoamer an antifreeze and an antimicrobial agent (e.g., Example G above).
  • compositions described above were tested for herbicidal efficacy on Brachiaria decumbens.
  • the weed was planted in 240 rnL pots filled with substrate with 3 repetitions for each treatment. The pots were left in a greenhouse under automatic irrigation until they reached the target size for the application compositions.
  • the test compositions were applied by spray application, individually and in combination at the rates indicated when Brachiaria decumbens reached 3 to 4 leaves stage (15 cm), and the control of weeds was assessed at 7, 14 and 21 days after the application and weed shoots was also collected at 21 days after the application to measure dry mass accumulation, as indicated in Tables 1, 2, 3 and 4 below.
  • Expected Control (%) is calculated by the following formula (Colby, 1967): wherein X and Y are the Control Observed (%) provided by the herbicides applied individually, and E is the Expected Control (%) for the combination at the same rate (X + Y).
  • Table 1 Control of Brachiaria decumbens 7 days after application.
  • Table 2 Control of Brachiaria decumbens 14 days after application.
  • Table 3 Control of Brachiaria decumbens 21 days after application.
  • Table 4 Inverse of the dry matter content of Brachiaria decumbens.
  • compositions described above were tested for herbicidal efficacy on Lolium multiflorum.
  • the weed was planted in 240 mL pots filled with substrate with 5 repetitions for each treatment. The pots were left in a greenhouse under automatic irrigation until they reached the target size for the application compositions.
  • the test compositions were applied by spray application, individually and in combination at the rates indicated when Lolium multiflorum reached the 2 tillers stage, and the control of weeds was assessed at 5, 7, 14 and 28 days after the application and weed shoots was also collected at 28 days after the application to measure dry mass accumulation, as indicated in Tables 5, 6, 7, 8 and 9 below.
  • Table 6 Control of Lolium multiflorum 7 days after application.
  • Table 7 Control of Lolium multiflorum 14 days after application.
  • Table 8 Control of Lolium multiflorum 28 days after application.
  • Table 9 Inverse of the dry matter content of Lolium multiflorum.
  • Herbicide solutions were prepared in 250 mL water for each herbicide. Herbicide solutions were prepared at least 30 mins before application to allow each herbicide commercial product to be fully dissolved in water. Bottles containing final herbicide solutions were vigorously agitated at least 10 times prior to herbicide application. Herbicide treatments at various dosages with the pre-emergence herbicide bixlozone were applied pre-emergence (PRE) with the herbicide in full contact with the weed seed. The seeds were not pregerminated on agar but were counted and placed into pots.
  • PRE pre-emergence
  • Post-emergence (POST) herbicide treatments were applied to two-leaf stage ryegrass seedlings. Plant survival (emergence followed by active growth) and plant growth (aboveground biomass) were assessed 6 weeks after treatments. Tillers and plant heads were counted 16-14 w eeks after spraying and the ability of each plant to set seed was expressed as percentage of untreated control.
  • Herbicide treatments listed in Table 10 were applied using a twin-nozzle laboratory sprayer calibrated to deliver 110 L of spray volume ha -1 at each pass at 210 kPa. Two hours after the PRE herbicide treatment weed and crop seeds were covered with a layer of potting mix of 0.5 cm and gently- watered afterwards. Each herbicide dose was applied to three replicated pots. The replicated pot was the experimental unit. The experiment was not repeated.
  • the percent plant survival values were calculated by dividing the number of survivors (ie plants able to emerge, establish and grow) by 33 which w as the total number of seeds sow n in each replicated pot.
  • For post-emergence plant survival (survivors / number of seedlings counted before the application of POST treatments) was also expressed as percentage. Plant growth was visually assessed and expressed as percent of the aboveground biomass of untreated control. Data were then transformed and expressed as plant mortality / kill rate percentage (100 - plant survival %) or percentage of plant biomass suppression (100 - visually estimated % of untreated control).
  • the seed set was estimated by counting the number of fertile tillers of plants surviving the herbicide treatment that could produce a fertile head with seeds filling and developing tow ards full maturity. Similarly to plant survival and biomass, the seed set data collected were transformed as percent of seed set reduction relative to the untreated control (100 - seed set % of untreated control).
  • E (Xi + X2)-[(Xi * X2)/100]) was used to assess the type of interaction between the herbicides tested in this study applied as stand-alones vs their respective binary- mixtures.
  • E is the expected level of weed control indicating additive interaction when two herbicides are combined in a mixture
  • Xi is the percentage of observed control with one herbicide (eg bixlozone)
  • X2 is the percentage of weed control with the second herbicide examined (eg paraquat or atrazine).
  • T-test was used to compare expected additive herbicide responses calculated with Colby equation and observed herbicide responses (plant mortality 7 % or plant biomass suppression %) and P-values calculated.

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Abstract

La présente invention concerne un mélange comprenant du bixlozone et au moins un herbicide choisi parmi les déflecteurs d'électrons du photosystème I et leurs sels et esters acceptables en agriculture. L'invention concerne également une composition agrochimique du mélange et un procédé d'utilisation du mélange ou de la composition.
PCT/US2024/035696 2023-06-30 2024-06-27 Mélanges de bixlozone avec déflecteurs d'électrons du photosystème i WO2025006659A1 (fr)

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