WO2023114652A1 - Procédé d'application d'une composition comprenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique ou son dérivé - Google Patents

Procédé d'application d'une composition comprenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique ou son dérivé Download PDF

Info

Publication number
WO2023114652A1
WO2023114652A1 PCT/US2022/080891 US2022080891W WO2023114652A1 WO 2023114652 A1 WO2023114652 A1 WO 2023114652A1 US 2022080891 W US2022080891 W US 2022080891W WO 2023114652 A1 WO2023114652 A1 WO 2023114652A1
Authority
WO
WIPO (PCT)
Prior art keywords
inhibitors
rice
formula
compound
ester
Prior art date
Application number
PCT/US2022/080891
Other languages
English (en)
Inventor
Natalino DALLA VALLE
Richard K. Mann
Original Assignee
Corteva Agriscience Llc
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 Corteva Agriscience Llc filed Critical Corteva Agriscience Llc
Publication of WO2023114652A1 publication Critical patent/WO2023114652A1/fr

Links

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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01P13/02—Herbicides; Algicides selective

Definitions

  • compositions comprising 4-amino-3-chloro-
  • compositions comprising an herbici dally effective amount of a compound of the formula (I): or an agriculturally acceptable salt or ester of thereof.
  • the composition additionally may contain an agriculturally acceptable adjuvant or carrier.
  • the composition is applied to a rice paddy prior to planting rice.
  • a compound of formula (I), or an agriculturally acceptable salt or ester thereof, and (b) a second herbicide are applied to a rice paddy subsequent to emergence of dry seeded rice, wet seeded rice or planting transplanted rice and/or prior to or after emergence of undesirable vegetation.
  • the second herbicide is a tiazolopyrimidine sulfonamide.
  • Exemplary triazolopyrimidine sulfonamides include, but are not limited to, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof.
  • the second herbicide is penoxsulam.
  • the compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (i.e., florpyrauxifen) and has been described in U.S. Patent Nos. 8,883,688 and 8,906,825, among others, each of which is incorporated by reference herein in its entirety.
  • the compound of formula (I) and its benzyl ester have been found to control undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.
  • the methods provided herein have demonstrated control of the following typically undesirable vegetation: Heteranthera reniformis R.
  • Echinocloa species e.g., Echinocloa crus-galli (L.) P.Beauv., i.e., “barnyardgrass,” “ECHCG”)
  • Cyperus difformis L e.g., Cyperus difformis L.
  • triazolopyrimidine sulfonamides are a chemical class of herbicides having a triazolopyrimidine sulfonamide core structure. Without being limited by any theory, the mode of action of triazolopyrimidine sulfonamides is believed to involve the inhibition of acetolactate synthase (“ALS”), an enzyme common to plants and microorganisms but not found in animals. Exemplary herbicidal uses of triazolopyrimidine sulfonamides include, but are not limited to, use for control of nuisance sedge, broadleaf and grass weeds.
  • ALS acetolactate synthase
  • Exemplary triazolopyrimidine sulfonamides include, but are not limited to, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam.
  • cloransulam-methyl is methyl 3-chloro-2-[[(5-ethoxy-7- fhioro[l,2,4]triazolo[l,5-c]pyrimidin-2-yl)sulfonyl]amino]benzoate and possesses the following structure:
  • diclosulam is 7V-(2,6-dichlorophenyl)-5-ethoxy-7- fhioro[l,2,4]triazolo[l,5-c]pyrimidine-2-sulfonamide and possesses the following structure:
  • Exemplary uses of diclosulam include its use as a herbicide for broadleaf weed control in peanuts and soybeans.
  • florasulam is A-(2,6-difluorophenyl)-8-fluoro-5- methoxy[l,2,4]triazolo[l,5-c]pyrimidine-2-sulfonamide and possesses the following structure:
  • florasulam includes its use as a herbicide in post-emergence control of broadleaf weeds in cereals and maize.
  • flumetsulam is A-(2,6-difluorophenyl)-5- methyl[l,2,4]triazolo[l,5-a]pyrimidine-2-sulfonamide and possesses the following structure:
  • flumetsulam examples include its use as a herbicide for the control of broadleaf weeds and grasses in soya beans, field peas and maize.
  • metosulam is A-(2,6-dichloro-3-methylphenyl)-5,7- dimethoxy[l,2,4]triazolo[l,5-a]pyrimidine-2-sulfonamide and possesses the following structure:
  • metosulam includes its use as a herbicide for post-emergence control of broadleaf weeds in wheat, barley and rye, and pre- or post-emergence control of broadleaf weeds in maize.
  • penoxsulam is 2-(2,2-difluoroethoxy)-A-(5,8- dimethoxy[l,2,4]triazolo[l,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide and possesses the following structure:
  • penoxsulam Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of penoxsulam includes its use as a herbicide for post-emergence control of Echinochloa spp., broadleaf weeds and annual sedge weeds in rice, as well as Echinochloa spp. and broadleaf weeds in sorghum, turf, cereals and tree and vine crops. In another example, penoxsulam is used to control aquatic weeds in lakes and ponds.
  • pyroxsulam is A-(5,7-dimethoxy[l,2,4]triazolo[l,5-a]pyrimidin-2- yl)-2-methoxy-4-(trifluoromethyl)-3 -pyridinesulfonamide and possesses the following structure:
  • herbicide means a compound, e.g., active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
  • a herbicidally effective amount or vegetation controlling amount each is an amount of active ingredient that causes an adversely modifying effect to the vegetation, e.g., causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.
  • controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation.
  • Described herein are methods of controlling undesirable vegetation through the application of certain herbicide combinations or compositions.
  • Methods of application include, but are not limited to applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, as well as preemergence, postemergence, foliar, and in-water applications.
  • plants and vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
  • agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide.
  • exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid, which, depending on certain factor(s) including, e.g., pH, may be in the dissociated or undissociated form.
  • Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines.
  • Exemplary cations include sodium, potassium, magnesium, and aminium cations of the formula:
  • Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methyl- thiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.
  • a metal hydroxide such as sodium hydroxide
  • an amine such as ammonia, trimethylamine, diethanolamine, 2-methyl- thiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine
  • a tetraalkylammonium hydroxide such as tetramethylammonium hydroxide or choline hydroxide.
  • esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl -substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1 -butanol, 2-ethylhexanol, butoxy ethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols.
  • Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy.
  • Esters can be prepared by coupling of the acids with the alcohol using any number of suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkylhalides or alkyl sulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
  • the compound of formula (I) is a benzyl ester of the compound of formula (I).
  • compositions comprising an herbicidally effective amount of a compound of the formula (I): or an agriculturally acceptable salt or ester thereof.
  • the compound of formula (I) or agriculturally acceptable salt or ester thereof is a benzyl ester of the compound of formula (I):
  • composition additionally may contain an agriculturally acceptable adjuvant or carrier.
  • the composition is applied to a rice paddy prior to planting of rice (i.e., “pre-planting”).
  • a compound of formula (I), or an agriculturally acceptable salt or ester thereof, and (b) a second herbicide are applied to a rice paddy subsequent to emergence of rice plants and/or undesirable vegetation (z.e., “postemergence”).
  • the second herbicide is a tiazolopyrimidine sulfonamide.
  • Exemplary triazolopyrimidine sulfonamides include, but are not limited to, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof.
  • the second herbicide is penoxsulam.
  • the compound of formula (I), z.e., the carboxylic acid is applied pre-planting to a rice paddy.
  • a carboxylate salt of the compound of formula (I) is applied pre-planting to a rice paddy.
  • an aralkyl or alkyl ester is applied pre-planting to a rice paddy.
  • a benzyl, substituted benzyl, or Ci-4 alkyl, e.g., n-butyl ester is applied pre-planting to a rice paddy.
  • the benzyl ester is applied pre-planting to a rice paddy.
  • the compound of formula (I) or salt or ester thereof and cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially post-emergence to a rice paddy.
  • compositions described herein are applied as a postemergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature undesirable vegetation to achieve the maximum control of weeds.
  • the methods provided herein are utilized to control undesirable vegetation (e.g., weeds) in rice.
  • the rice is direct seeded, water seeded, or transplanted rice.
  • the compositions and methods described herein be used to control undesirable vegetation on glyphosate-tolerant-, glufosinate-tolerant-, di camba-tol erant-, phenoxy auxin- tolerant-, pyridyloxy auxin-tolerant-, aryl oxyphenoxypropionate-tol erant-, acetyl CoA carboxylase (“ACCase”) inhibitor-tolerant-, imidazolinone-tolerant-, acetolactate synthase (“ALS”) inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor - tolerant-, protoporphyrinogen oxidase (“PPO”) inhibitor -tolerant-, triazine-tolerant-, bromoxy
  • ACCase acetyl Co
  • the methods may be used in controlling undesirable vegetation in rice possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or inhibitors of multiple modes of action.
  • the compound of formula (I) or salt or ester thereof and second herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop (e.g., rice) being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed.
  • the compositions described herein and other secondary herbicides are applied at the same time, either as a combination formulation or as a tank mix.
  • the methods provided herein are utilized to control undesirable vegetation in rice.
  • the undesirable vegetation is Urochloa platyphylla (Groseb.) Nash (/. ⁇ ., “broadleaf signalgrass,” “BRAPP”), Digitaria sanguinalis (L.) Scop, (i.e., “large crabgrass,” “DIGSA”), Echinocloa species (“ECHSS”), e.g., Echinochloa crus-galli (L.) P. Beauv.
  • Leptochloa chinensis L.
  • Nees i.e., “Chinese sprangletop,” “LEFCH”
  • Leptochloa fascicularis Lam.) Gray
  • Panicum dichotomiflorum L.) Michx. (z.e., “fall panicum,” “PANDI”)
  • Paspalum dilatatum Poir i.e., “saramollagrass,” “ISCRU”
  • Leptochloa chinensis L.
  • Nees i.e., “Chinese sprangletop,” “LEFCH”
  • Leptochloa fascicularis Lam.) Gray
  • ELOSS Fimbristylis miliacea (L.) Vahl (i.e., “globe fringerush,” “FIMMI”), Schoenoplectus juncoides Roxb. (i.e., “Japanese bulrush,” “SPCJU”), Schoenoplectus maritimus L. i.e., “sea clubrush,” “SCPMA”), Schoenoplectus mucronatus L. (i.e., “ricefield bulrush,” “SCPMU”), Aeschynomene species, (i.e., “jointvetch,” “AESSS”), Alternanthera philoxeroides (Mart.) Griseb.
  • alligatorweed i.e., “alligatorweed,” “ALRPH”
  • Alisma plantago-aquatica V. i.e., “common waterplantain,” “ALSPA”
  • Amaranthus species i.e., “AMASS,” e.g., pigweeds and amaranths
  • Ammannia coccinea Rottb. i.e., “redstem,” “AMMCO”
  • Eclipta alba L.
  • Presl ex Kuhth i.e., “monochoria,” “MOOVA”
  • MOOVA Murdannia midiflora
  • L. Brenan
  • POLSS Polygonum species
  • POLSS Polygonum pensylvanicum L.
  • Pennsylvania smartweed POLPY
  • POLPE Polygonum persicaria .
  • POLPE Polygonum hydropiperoides Michx.
  • compositions and methods provided herein are utilized to control undesirable vegetation consisting of grass, broadleaf and sedge weeds.
  • the compositions and methods provided herein are utilized to control undesirable vegetation including Brachiaria, Chamomilla, Cirsium, Cyperus, Digitaria, Echinochloa, Ipomoea, Lamium, Leptochloa, Salsola, Schoenoplectus, Veronica and Viola.
  • the compounds of formula I or agriculturally acceptable salt or ester thereof may be used to control herbicide resistant or tolerant weeds.
  • exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (“ALS”) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (“ACCase”) inhibitors, synthetic auxins, photosystem I inhibitors, 5- enolpyruvylshikimate-3 -phosphate (“EPSP”) synthase inhibitors, microtubule assembly inhibitors, lipid synthesis inhibitors, protoporphyrinogen oxidase (“PPG”) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (“VLCFA”) inhibitors, phytoene desaturase (“PDS”) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl -pyruvatedioxygenase (“HPPD”) inhibitors
  • ALS acetolactate synthase
  • ACCase acetyl CoA carboxylase
  • EPP 5- enolpyruvyl
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with the second herbicide or salt, carboxylic acid, carboxylate salt, or ester thereof are used to control HETRE, HETLI, ECHGC, ECHSS, CPYDI, and/or AMMCO.
  • compositions described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation.
  • the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides.
  • herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4, 5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos- methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafen
  • compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and -phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
  • herbicide safeners such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide
  • the safeners are employed in rice, cereal, com, or maize settings.
  • the safener is cloquintocet or an ester or salt thereof.
  • cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals.
  • the safener is isoxadifen-ethyl.
  • compositions provided herein further comprise at least one agriculturally acceptable adjuvant or carrier.
  • Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients.
  • Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application.
  • They can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided as a pre-mix or tank mixed.
  • Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di- ec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate- 99.
  • Liquid carriers that can be employed include water and organic solvents.
  • the organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, //-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarbox
  • organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, 7V-methyl-2-pyrrolidinone, N,N-di methyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like.
  • Water is the carrier for the dilution of concentrates.
  • Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.
  • the compositions described herein further comprise one or more surface-active agents.
  • such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application.
  • the surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
  • Surfactants which may also be used in the present formulations are described, inter alia, in “McCutcheon’s Detergents and Emulsifiers Annual,” MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980-81.
  • Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol -alkylene oxide addition products, such as nonylphenol-Cis ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Ci6 ethoxylate; soaps, such as sodium stearate; alkyl- naphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; poly
  • these materials can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.
  • compositions include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like.
  • the compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
  • the concentration of the active ingredients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight.
  • the active ingredients in certain embodiments, are present in a concentration from about 0.1 to 98 weight percent, and in certain embodiments about 0.5 to 90 weight percent.
  • Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application.
  • the diluted compositions usually applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0003 to 1.5 weight percent active ingredient and in certain embodiments contain about 0.0008 to 1.0 weight percent.
  • compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
  • the described embodiments and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.
  • ORYSA Oriza sativa
  • HETRE Heteranthera reniformis R. & P.
  • Echinochloa crus-galli L.
  • EHCG Echinochloa crus-galli
  • Cyperus difformis L. z.e., “smallflower flatsedge,” “CYPDI”
  • POLSS Polygonum species
  • Formula A contained 25 g of the benzyl ester of the compound of formula (I) per liter.
  • Formula B contained 20 g of penoxsulam and 12.5 g of the benzyl ester of the compound of formula (I) per liter.
  • Cropping System Even Further Evaluation of Pre-Planting and additionally Post-Emergence Foliar- Applied Herbicidal Mixtures for Weed Control in Direct Seeded Rice.
  • Formula A contained 25 g of the benzyl ester of the compound of formula (I) per liter.
  • Formula B contained 20 g of penoxsulam and 12.5 g of the benzyl ester of the compound of formula (I) per liter.

Landscapes

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

Abstract

L'invention concerne des procédés d'utilisation de compositions herbicides contenant un composé de formule (I) : (« acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique »), ou son sel ou ester acceptable en agriculture. Les procédés permettent de lutter contre la végétation indésirable dans des rizières. Des modes de réalisation des procédés comprennent, entre autres, l'application d'une composition herbicide contenant un composé de formule (I) « préplantation. »
PCT/US2022/080891 2021-12-16 2022-12-05 Procédé d'application d'une composition comprenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique ou son dérivé WO2023114652A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163290237P 2021-12-16 2021-12-16
US63/290,237 2021-12-16

Publications (1)

Publication Number Publication Date
WO2023114652A1 true WO2023114652A1 (fr) 2023-06-22

Family

ID=85018413

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2022/080891 WO2023114652A1 (fr) 2021-12-16 2022-12-05 Procédé d'application d'une composition comprenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique ou son dérivé

Country Status (1)

Country Link
WO (1) WO2023114652A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014018407A1 (fr) * 2012-07-24 2014-01-30 Dow Agrosciences Llc Compositions herbicides contenant de l'acide 4-amino -3-chloro -5-fluoro -6- (4-chloro -2-fluoro -3-méthoxyphényl) pyridine -2-carboxylique
WO2014018358A1 (fr) * 2012-07-24 2014-01-30 Dow Agrosciences Llc Compositions herbicides phytoprotectrices destinées à être utilisées dans le riz
US8883688B2 (en) 2011-01-25 2014-11-11 Dow Agrosciences, Llc. Arylalkyl esters of 4-amino-6-(substituted phenyl)-picolinates and 6-amino-2-(substituted phenyl)-pyrimidinecarboxylates and their use as selective herbicides for crops
US8906825B2 (en) 2012-07-24 2014-12-09 Dow Agrosciences, Llc. Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and triazolopyrimidine sulfonamides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8883688B2 (en) 2011-01-25 2014-11-11 Dow Agrosciences, Llc. Arylalkyl esters of 4-amino-6-(substituted phenyl)-picolinates and 6-amino-2-(substituted phenyl)-pyrimidinecarboxylates and their use as selective herbicides for crops
WO2014018407A1 (fr) * 2012-07-24 2014-01-30 Dow Agrosciences Llc Compositions herbicides contenant de l'acide 4-amino -3-chloro -5-fluoro -6- (4-chloro -2-fluoro -3-méthoxyphényl) pyridine -2-carboxylique
WO2014018358A1 (fr) * 2012-07-24 2014-01-30 Dow Agrosciences Llc Compositions herbicides phytoprotectrices destinées à être utilisées dans le riz
US8906825B2 (en) 2012-07-24 2014-12-09 Dow Agrosciences, Llc. Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and triazolopyrimidine sulfonamides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Encyclopedia of Surfactants", vol. I-III, 1980, CHEMICAL PUBLISHING CO., pages: 81
"McCutcheon's Detergents and Emulsifiers Annual", 1998, MC PUBLISHING CORP.
THE PESTICIDE MANUAL, 2009

Similar Documents

Publication Publication Date Title
AU2013293356B2 (en) Safened herbicidal compositions for use in rice
CA2879664C (fr) Compositions herbicides phytoprotectrices comprenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylique
AU2013315646B2 (en) Herbicidal compositions comprising aminopyralid and triclopyr
AU2022200660A1 (en) Herbicidal compositions containing 4-amino-3-chloro-6-(4-chloro-2-fluouro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and a cell membrane disruptor herbicide or a derivative thereof
WO2017044585A1 (fr) Compositions herbicides contenant de l'acide 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphényl) pyridine-2-carboxylique, un herbicide de type sulfonamide de triazolopyrimidine et un herbicide destructeur de membrane cellulaire
EP3664607A1 (fr) Compositions herbicides contenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique ou un dérivé de celui-ci et de la tembotrione ou de la topramézone
US10098349B2 (en) Herbicidal compositions containing imazapic, aminopyralid and optionally metsulfuron
US9451776B2 (en) Herbicidal compositions comprising fluroxypyr and flumetsulam
WO2017035065A1 (fr) Lutte contre les mauvaises herbes à large spectre dans des rizières inondées par application dans l'eau d'herbicides d'auxine
AU2013315651B2 (en) Herbicidal compositions comprising aminopyralid and bentazon
WO2023114652A1 (fr) Procédé d'application d'une composition comprenant de l'acide 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl) pyridine-2-carboxylique ou son dérivé
US9854800B2 (en) Herbicidal compositions comprising 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid or a derivative thereof and chlormequat chloride
AU2013315648B2 (en) Herbicidal compositions comprising aminopyralid and propanil

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22847048

Country of ref document: EP

Kind code of ref document: A1