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WO2025212359A1 - Mélange de bixlozone, composition et procédé herbicide - Google Patents

Mélange de bixlozone, composition et procédé herbicide

Info

Publication number
WO2025212359A1
WO2025212359A1 PCT/US2025/021717 US2025021717W WO2025212359A1 WO 2025212359 A1 WO2025212359 A1 WO 2025212359A1 US 2025021717 W US2025021717 W US 2025021717W WO 2025212359 A1 WO2025212359 A1 WO 2025212359A1
Authority
WO
WIPO (PCT)
Prior art keywords
mixture
component
methyl
undesired vegetation
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/021717
Other languages
English (en)
Inventor
Atul Puri
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
FMC Corp
Original Assignee
FMC Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by FMC Corp filed Critical FMC Corp
Publication of WO2025212359A1 publication Critical patent/WO2025212359A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—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
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • 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 mixture of bixlozone in combination with a second active ingredient, compositions containing the mixture, and methods for using the mixture for controlling undesirable vegetation.
  • This invention is directed to a mixture comprising (a) bixlozone, and salts thereof and (b) a compound of Formula I or Formula II
  • This invention also includes the herbicidal mixture further comprising (c) at least one additional active ingredient.
  • This invention also relates to a herbicidal composition comprising a mixture of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains,” “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • a mixture, composition or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such mixture, composition or method.
  • narrowleaf used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
  • Combinations of herbicides are typically used to broaden the spectrum of plant control or enhance the level of control of any given species through additive effect. Certain rare combinations surprisingly give a greater-than-additive effect. Such valuable mixtures, compositions and methods have now been discovered.
  • United States Patent 4,405,357 discloses certain 3-isoxazolidinones which exhibit desirable selective herbicidal activity. Specifically, such compounds are shown to be effective in controlling grassy and broadleaf weed species while leaving legumes, particularly soybeans, unaffected. Among the compounds specifically disclosed in this patent is 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (CA No. 81777-95-9) which is biologically active against a number of weed species.
  • Bixlozone is a herbicide recently introduced by FMC with the CAS name of 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone.
  • bixlozone is sold commercially as (a formulated material as) “Overwatch” and has also previously been referred to as “DCPMI”, “F9600”, “2,4-DC” and “dichloroclomazone”.
  • DCPMI a formulated material as
  • bixlozone may be technical grade bixlozone with purity range of 90 to 95% by weight.
  • the bixlozone may be a composition comprising more than 95% by weight pure 2-(2,4-dichlorophenyl) methyl-4,4-dimethyl-3-isoxazolinone.
  • pure bixlozone means 100% pure 2-(2,4- dichlorophenyl) methyl-4,4-dimethyl-3-isoxazolinone.
  • Bixlozone can be prepared according to the procedure described in WO 2019/209847. Alternatively, bixlozone can be purchased as a composition (formulation) as Overwatch® from the FMC corporation.
  • the compound of Formula I is assigned the common name “rimisoxafen” and can be prepared by using general procedures described in WO 2015/108779 or WO 2021/113284.
  • the compound of Formula II can be prepared as described in WO 2016/196606.
  • Bixlozone can exist as one or more rotomers, or in different crystal forms (for example WO 2019/030177 and WO 2019/243104).
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers are therefore included in this disclosure.
  • Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers (also known as geo isomers) and atropisomers.
  • Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species.
  • Rimixoafen i.e. a compound of Formula I, CAS No. 1801862-02-1
  • Rimixoafen can also exist in various rotomeric forms, depending on if the compouind is in the solid form, or if it is dissolved in a particular solvent. This discloseure encompasses all of the various forms of both bixlozone and rimisoxafen. For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.
  • This disclosure comprises racemic mixtures, for example, equal amounts of one rotamer/crystal form.
  • this disclosure includes a mixture of either bixlozone and rimisoxafen that is enriched in one rotamer/crystal form in comparison to the opposite rotamer or other crystal structure. Also included in this disclosure is the essentially pure rotamer/crystal form of bixlozone and the compound of Formulae I or II.
  • Component (b) of the present invention is a compound of Formula I or Formula II.
  • Preferred as a compound of component (b) is a compond of Formula II. More preferred as a compound of component (b) is a compond of Formula I.
  • component (a) or component (b) of the present recitatation contain a nitrogen atom with a free pair of electons capable of protonation
  • salt formation can occour in the presence of an acid. Under some conditions, salt formation can be brought about in th presence of a base.
  • the molecular weight of Formula I is 358.13 g/mole
  • that of Formula II is 365.13 g/mole.
  • the compounds of Formulae I and II can exist in more than one form, and thus include all crystalline and non-crystalline forms of the compounds they represent.
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
  • polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • beneficial effects e.g., suitability for preparation of useful formulations, improved biological performance
  • Preparation and isolation of a particular polymorph of compounds of component (a) or (b) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • crystallization using selected solvents and temperatures.
  • salts of compounds of Formulae I and II are useful for control of undesired vegetation (i.e. are agriculturally suitable).
  • the salts of compounds of Formulae I and II 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.
  • Embodiment 2 The mixture of Embodiment 1 wherein component (b) is the compound of Formula I.
  • Embodiment 3 The mixture of Embodiment 1 wherein component (b) is the compound of Formula II.
  • Embodiment 4 The mixture of any one of Embodiments 1 through 3 wherein component (a) is applied from about 25 g a.i./ha to about 1000 g a.i./ha.
  • Embodiment 5 The mixture of Embodiment 4 wherein component (a) is applied at from about 30 g a.i./ha to about 500 g a.i./ha.
  • Embodiment 7 The mixture of Embodiment 6 wherein component (a) is applied from about 50 g a.i./ha to about 400 g a.i./ha.
  • Embodiment 8 The mixture of Embodiment 7 wherein component (a) is applied from about 60 g a.i./ha to about 350 g a.i./ha.
  • Embodiment 9 The mixture of Embodiment 8 wherein component (a) ia applied from about 65 g a.i./ha to about 300 g a.i./ha.
  • Embodiment 10 The mixture of Embodiment 9 wherein component (a) is applied from about 70 g a.i./ha to about 275 g a.i./ha.
  • Embodiment 11 The mixture of Embodiment 10 wherein component (a) is applied from about 75 g a.i./ha to about 250 g a.i./ha.
  • Embodiment 13 The mixture of Embodiment 12 wherein component (a) is applied at least about 80 g a.i./ha.
  • Embodiment 15 The mixture of Embodiment 12 wherein component (a) is applied at least about 100 g a.i./ha.
  • Embodiment 16 The mixture of Embodiment 12 wherein component (a) is applied at least about 110 g a.i./ha.
  • Embodiment 18 The mixture of Embodiment 12 wherein component (a) is applied at least about 130 g a.i./ha.
  • Embodiment 19 The mixture of Embodiment 12 wherein component (a) is applied at least about 140 g a.i./ha.
  • Embodiment 19A The mixture of any one of Embodiments 1 through 19 wherein component (b) is applied at least about 20 g a.i./ha.
  • Embodiment 19B The mixture of Embodiment 19A wherein component (b) is applied at least about 30 g a.i./ha.
  • Embodiment 19C The mixture of Embodiment 19B wherein component (b) is applied at least about 40 g a.i./ha.
  • Embodiment 19D The mixture of Embodiment 19C wherein component (b) is applied at least about 50 g a.i./ha.
  • Embodiment 19E The mixture of Embodiment 19C wherein component (b) is applied at least about 60 g a.i./ha.
  • Embodiment 191 The mixture of any one of Embodiments 19A through 19F wherein component (b) is applied at less than about 125 g a.i./ha.
  • Embodiment 19J The mixture of any one of Embodiments 19A through 19F wherein component (b) is applied at less than about 100 g a.i./ha.
  • Embodiment 20 The mixture of any one of Embodiments 1 through 19 wherein the weight ratio of (a) to (b) is from about 100:1 to about 1: 1.
  • Embodiment 21 The mixture of Embodiment 20 wherein the weight ratio of (a) to (b) is from about 75:1 to about 1: 1.
  • Embodiment 23 The mixture of Embodiment 20 wherein the weight ratio of (a) to (b) is from about 40:1 to about 1:1.
  • Embodiment 27 The mixture of Embodiment 20 wherein the weight ratio of (a) to (b) is from about 6: 1 to about 1.5: 1.
  • Embodiment 28 The mixture of Embodiment 20 wherein the weight ratio of (a) to (b) is from about 4: 1 to about 1.5: 1.
  • Embodiment 32 The mixture of any one of Embodiments 1 through 31 wherein the mixture further comprises a safener.
  • Embodiment 33 The mixture of Embodiment 32 wherein the ratio of component (a) to (b) to the safener is about 5:1 :0.35.
  • Embodiment 34 The mixture of Embodiment 33 wherein the safener is selected from mefenpyr and cloquintocet.
  • Embodiment 35 The mixture of Emodiment 34 wherein the safener is selected from mefenpyr-diethyl and cloquintocet-mexyl.
  • Embodiment 36 The mixture of Embodiment 35 wherein the safener is cloquintocet- mexyl.
  • Embodiment 37 A composition comprising the mixture as defined in any one of 1 through 36.
  • Embodiment 40 The composition of Embodiment 38 in the form of an oil dispersion (OD).
  • OD oil dispersion
  • Embodiment 41 The composition of Embodiment 38 in the form of a wettable powder (WP).
  • WP wettable powder
  • Embodiment 44 The composition of Embodiment 38 in the form of a capsule suspension (CS).
  • CS capsule suspension
  • Embodiment 45 The composition of Embodiments 43 and 44 in the form of a mixed formulation of a SE and CS (ZC).
  • Embodiment 46 A method for controlling undesired vegetation comprising appling a) the mixture defined in any of Embodiments 1 through 36, or b) the composition defined in any of Embodiments 37 through 45 to the undesired vegetation.
  • Embodiment 49 The method of any one of Embodiments 46 through 47 wherein the applying is post-emergence (i.e. after the undesired vegetation has emerged).
  • Embodiment 50 The method of any one of Embodiments 47 through 49 whererein the undesired vegetation is selected from the genus Amaranthus, Avena and Malva.
  • Embodiment 51 The method of Embodiment 50 wherein the undesired vegetation is redroot pigweed ⁇ Amaranthus relmjlexiis).
  • Embodiment 52 The method of Embodiments 46 through 47 wherein the undesired vegetation is selected from the genus Lolium and Raphanus.
  • Embodiment 53 The method of Embodiment 46 wherein said undesired vegetation is 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 testiculata), 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, corn 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
  • Embodiment 54 The method of Embodiment 53 wherein said undesired vegetation is selected from annual ryegrass (Lolium rigidum) and wild radish (Raphanus raphanistrum).
  • Embodiment 55 The method of Embodiment 54 wherein said undesired vegetation is selected from wild radish (Raphanus raphanistrum).
  • Embodiment 56 The method of Embodiment 50 wherein the undesired vegetation is wild oat (Avena fatua).
  • Embodiment 56A The method of Embodiment 56 wherein the undesired vegetation is wild oat (Avena fatua) evaluated at greater than 21-35 days after application.
  • wild oat Avena fatua
  • Embodiment 56B The method of Embodiment 56 wherein the undesired vegetation is wild oat (Avena fatua) evaluated at greater than 35 days after application.
  • Embodiment 56C The method of Embodiment 56B wherein the undesired vegetation is wild oat (Avena fatud) evaluated at greater than 40 days after application.
  • Embodiment 56F The method of Embodiment 53 or 54 wherein the undesired vegetation is other than wild oat (Avena fatud).
  • Embodiment 57 The method of Embodiment 50 wherein the undesired species is round-leaved mallow (Malva pusilia).
  • Embodiment 58 The method of any one Embodiment 47 through 49 wherein the undersired vegetation is selected from the genus Avena, Alopecurus, Bromus, Ambrosia and Kochia.
  • Embodiment 59 The method of Embodiment 58 whererein the undesired vegetation is selected from Avena fatua, Alopecurus myosuroides, Bromus tectorum, Ambrosia artemisiifolia, Kochia scoparia.
  • Embodiment 60 The method of any of Embodiments 47 through 59 wherein the undesired vegetaion is growing in spring wheat (triticum aestivum).
  • Embodiment 61 The method of any of Embodiments 47 through 59 wherin the undesired vegetation is growing in banana, barley, bean, beet, cassava, citrus, cocoa, coconut, coffee, com, grape, hops, oil palm, oilseed rape, pea, peanut, pomes, potato, rice, sugar cane, sunflower, tea, tobacco, walnut, almond, pecan, hickory, cashew, hazelnut or wheat.
  • Embodiment 61 A The method of any of Embodiments 47 through 59 wherein the undesired vegetation is growing in banana, barley, bean, beet, cassava, citrus, cocoa, coconut, coffee, com, grape, hops, oats, oil palm, oilseed rape, pea, peanut, pomes, potato, rice, sugar cane, sunflower, tea, tobacco, walnut, almond, pecan, hickory, cashew, hazelnut or wheat.
  • Embodiment 6 IB The method of Embodiment 61 A wherein the undesired vegetation is growing in barley, oats and wheat.
  • Embodiment 61C The method of Embodiment 6 IB wherein the undesired vegetation is growing in barley and wheat.
  • Embodiment 61D The method of any of Embodiments 47 through 59 wherein the undesired vegetation is growing in pulse crops selected from soybean, mung bean, lupin, field pea, chickpea, faba bean and lentil.
  • Embodiment 6 IE The method of Embodiment 61D wherein the undesired vegetation is growing in pulse crops selected from lupin, field pea, chickpea, faba bean and lentil.
  • Embodiment 6 IF The method of Embodiment 6 ID wherein the undesired vegetation is growing in pulse crops selected from soybean and mung bean.
  • the mixture of this invention further comprising (c) at least one additional active ingredient includes 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 compounds 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 further comprising at least one additional biologically active compound 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 compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent.
  • one or more other biologically active compounds or agents can be formulated together with a present mixture, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula I, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
  • At least one additional active ingredient can be one or more of the following herbicides particularly useful for weed control: acetochlor, acifhiorfen 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, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquitrione, bensulfuron-methyl, bensul
  • herbicides also include bioherbicides such as Allernaria deslruens Simmons, Collelolrichum gloeosporiod.es (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • bioherbicides such as Allernaria deslruens Simmons, Collelolrichum gloeosporiod.es (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thla
  • Preferred for better control of undesired vegetation e.g., lower use rate such as from greater-than-additive effects, broader spectrum of weeds controlled, or enhanced crop safety
  • a herbicide selected from the group consisting of atrazine, azimsulfuron, beflubutamid, beflubutamid-M, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, ethametsulfuron-methyl, fhimetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-l- cyclohexen-l-yl)carbonyl]-2- methyl- 1, 2, 4-triazine-3,5-(2//,4//)-dione,
  • Mixtures of this invention can also be used in combination with plant growth regulators such as aviglycine, phenyl methyl)- 1 H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
  • plant growth regulators such as aviglycine, phenyl methyl)- 1 H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl
  • plant growth regulators such as Bacillus cereus strain BP01.
  • 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 Manual.
  • the weight ratio of these various mixing partners (in total) to the present mixture 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 present mixture alone.
  • combinations of a mixture of this invention with other biologically active (particularly herbicidal) compounds or agents can result in a greater-than-additive 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. When greater-than-additive effects 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.
  • bixlozone can be provided as a formulated mixture with pethoxamid as described in PCT/US23/34070 or as a formulated mixture with beflubutamid (or beflubutamid-M) as described in PCT/US23/34068.
  • the mixtures of this invention can also be used in combination with herbicide safeners (i.e. as component (c)) selected from 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, A-(aminocarbonyl)-2-methylbenzenesulfonamide, N- (aminocarbonyl) -
  • herbicide safeners i.e. as component (c)
  • component (c) selected from
  • 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 a 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 growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally 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.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the mixture of the invention (e.g., as a composition described herein).
  • the mixture of the invention e.g., as a composition described herein.
  • embodiments relating to methods of use are those involving the mixtures of embodiments described above.
  • Mixtures of the invention are particularly useful for selective control of weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.
  • crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice
  • specialty crops such as sugarcane, citrus, fruit and nut crops.
  • the present invention is the selective control of weeds in a transplanted rice crop.
  • the selective control of weeds in a direct- seeded rice crop are particularly useful for selective control of weeds in crops such
  • a mixture 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 type, 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 al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
  • Liquid diluents include, for example, water, N.A'-dimethylalkan amides (e.g., NW-dimethylformamide), limonene, dimethyl sulfoxide, -alkylpyrrolidones (e.g., A-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone
  • 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, 2nd 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 wetting 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, hut 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
  • 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.
  • the herbicidal mixture can be formulated as single, separate ingredients (i.e as a copack) and mixed together (i.e. as a tank mix). Alternatively, the herbicidal mixture can be formulated separately, then mixed together before adding to the spray tank (i.e. a homogenous blend of soluble granules). Alternatively, the herbicidal mixture can be formulated together, then formulated, (i.e. as soluble granules). The amount of each compound of the herbicidal mixture (i.e. as compounent (a) and (b) (and optionally (c)) can be adjusted according to field conditions present. Likewise, the method of applying the herbicidal mixture or composition also comprises the sequential application of component (a) followed by component (b), or in reverse order (otherwise known as a “split” application).
  • Seeds of wild oat (AVEFA, Avena fatua), blackgrass (ALOMY, Alopecurus myosuroides), downy brome (BROTE, Bromus teciorum).
  • AMBEL Ambrosia artemisiifolia
  • KCHSC Kochia scoparia
  • Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of approximately 16 h; daytime and nighttime temperatures were approximately 26-29 °C and 24-26 °C, respectively.
  • Colby’s Equation was used to determine the herbicidal effects expected from the mixtures and compare them with the observed efficacies.
  • Colby’s Equation (Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds' 1967 75(1), pp 20-22) calculates the expected additive effect of herbicidal mixtures and for two active ingredients is of the standard form.
  • Table A Observed and Expected Results (28 DAA) in Grass Weed Species From Bixlozone alone and The Compound of Formula I Alone and in Tank-Mix Combination Table A: Grass Weeds (Continued)

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Abstract

La présente invention concerne un mélange comprenant (a) de la bixlozone, et des sels de celle-ci et (b) un composé de formule I ou de formule II. L'invention concerne également une composition comprenant ce mélange. La présente invention concerne en outre un mélange herbicide comprenant en outre au moins un principe actif supplémentaire. L'invention concerne enfin un procédé d'application du mélange ou de la composition à une végétation indésirable comprenant la mise en contact de la végétation indésirable ou de son environnement avec une quantité efficace du mélange de l'invention.
PCT/US2025/021717 2024-03-30 2025-03-27 Mélange de bixlozone, composition et procédé herbicide Pending WO2025212359A1 (fr)

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WO2021113284A1 (fr) 2019-12-02 2021-06-10 Fmc Corporation Procédé de synthèse d'un 2-(5-isoxazolyle)-phénol

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