WO2012175899A1 - Composition herbicide comprenant un herbicide pyranedione et un herbicide sulfonylurée - Google Patents

Composition herbicide comprenant un herbicide pyranedione et un herbicide sulfonylurée Download PDF

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Publication number
WO2012175899A1
WO2012175899A1 PCT/GB2011/000946 GB2011000946W WO2012175899A1 WO 2012175899 A1 WO2012175899 A1 WO 2012175899A1 GB 2011000946 W GB2011000946 W GB 2011000946W WO 2012175899 A1 WO2012175899 A1 WO 2012175899A1
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WIPO (PCT)
Prior art keywords
compound
salt
formula
herbicidal composition
calculated
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PCT/GB2011/000946
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English (en)
Inventor
Jane Elisabeth Corbin
Christopher John Mathews
Claudio Screpanti
Original Assignee
Syngenta Limited
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Publication date
Application filed by Syngenta Limited filed Critical Syngenta Limited
Priority to PCT/GB2011/000946 priority Critical patent/WO2012175899A1/fr
Priority to ARP120102217A priority patent/AR086701A1/es
Priority to UY0001034153A priority patent/UY34153A/es
Priority to TW101122382A priority patent/TW201313125A/zh
Publication of WO2012175899A1 publication Critical patent/WO2012175899A1/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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

Definitions

  • Herbicidal composition comprising a pyrandione herbicide and a sulfonyl urea herbicide
  • the present invention relates to a new herbicidal composition, for example suitable for controlling weeds (e.g. grassy weeds) in crops of useful plants, especially in crops of rice; which composition comprises a herbicidally active pyrandione [specifically, a 4-(substituted biphenyl-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4 ,6 -/)-dione; or more specifically, a 4-(4- ethyl or 4-cyclopropyl, 2'-chloro- or 2'-fluoro-, 4'-chloro-biphenyl-3-yl)-2,2,6,6-tetramethyl-2AV- pyran-3,5(4H,6 -/)-dione], or an enol ketone tautomer thereof; and a sulfonyl urea herbicide.
  • a herbicidally active pyrandione specifically, a 4-
  • WO 2008/071405 A1 (Syngenta Participations AG and Syngenta Limited) discloses pyrandione, thiopyrandione and cyclohexanedione compounds, and enol ketone tautomer derivatives thereof, suitable for use as herbicides. WO 2008/071405 A1 also discloses mixtures of these pyrandione, thiopyrandione or cyclohexanedione compounds with any of a large number of herbicidal mixture partners.
  • One of the many specific pyrandione herbicidal compounds disclosed in WO 200 A-45 whose structure is:
  • WO 2010/ 36431 A9 (Syngenta Limited) discloses a genus of spirocyclic epoxy ketones, and their use as intermediates in the preparation of herbicidally active substituted 4-phenyl-3,5- pyrandiones, 4-phenyl-3,5-thiopyrandiones and 6-phenylcyclohexane-1 ,3,5-triones including those disclosed in WO 2008/071405 A1.
  • Two of the several specific pyrandione compounds disclosed in WO 2010/136431 A9 are Example P8 and Example P10, whose structures are shown below:
  • WO 2010/136431 A9 WO 2010/136431 A9 Metazosulfuron (NC-620), whose CAS (Chemical Abstracts Service) registry number is 868680-84-6, is a herbicide of the sulfonyl urea class which has the following structure:
  • Metazosulfuron has the following chemical name: 3-chloro-4-(5,6-dihydro-5-methyl-1 ,4,2- dioxazin-3-yl)-/ ⁇ /-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1 H-pyrazole-5- sulfonamide.
  • Metazosulfuron may be used in the form of a salt (e.g. agriculturally acceptable salt) thereof.
  • Metazosulfuron and its synthesis is disclosed as Compound no. 1 in Examples 1 , 10, 11 and 12 on pages 18, 23 and 47 of EP 1 748 047 A1 (Nissan Chemical Industries, Ltd) which is derived from WO 2005/103044.
  • a mixture suitable for use in crops of rice for example either transplanted flooded rice (e.g. using post-emergent application to the flood-waters) or direct-seeded rice (e.g. using post- emergent foliar and/or spray application), preferably having low or relatively low levels of phytotoxicity on the rice crops; and/or
  • a first aspect of the present invention provides a herbicidal composition comprising:
  • R 1 is ethyl or cyclopropyl, and R 2 is chlorine or fluorine;
  • the herbicidal composition typically comprises:
  • the agriculturally acceptable salt of the compound of formula (I) can, for example, be an agriculturally acceptable base addition salt such as an alkali metal (e.g. sodium, potassium or lithium) salt, alkaline earth (e.g. calcium or magnesium) salt, ammonium salt, or a
  • tetraC C 4 alkylammonium e.g. tetramethylammonium, tetra-ethyl-ammonium or tetra-n- butylammonium
  • the anion of the base addition salt of the compound of formula (I) may, for example, have the following structure, where the negative charge is delocalized over the two diones and over the biphenyl:
  • the compound of formula (I) is present as the free compound (e.g. as a substantially salt-free compound). ln the compound of formula (I) or the salt thereof, in one preferred embodiment, R 1 is ethyl.
  • R 1 is cyclopropyl
  • R 1 is ethyl and R 2 is chlorine.
  • the compound of formula (I) is:
  • the above-shown compound has the following chemical name: 4-(2',4'-dichloro-4- ethylbiphenyl-3-yl)-2,2 ) 6,6-tetramethyl-2H-pyran-3,5(4 Y,6H)-dione. Still more preferably, this compound or the salt thereof is present as the free compound (e.g. as a substantially salt- free compound).
  • the above-shown compound, present as the free compound is named Compound no. 1.
  • This compound (as the enol ketone tautomer) was previously disclosed as compound A-45 in WO 2008/071405 A1, and as Example P10 within WO 2010/136431 A9, and can in general be synthesized using the methods of preparation disclosed in either of these publications.
  • R 1 is cyclopropyl and R 2 is fluorine.
  • the compound of formula I) is:
  • the above-shown compound has the following chemical name: 4-(4'-chloro-4-cyclopropyl-2'- fluorobiphenyl-3-yl)-2,2 ) 6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione. Still more preferably, this compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound).
  • the above-shown compound, present as the free compound is named Compound no. 2.
  • the above-shown compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound).
  • the above-shown compound present as the free compound (e.g. as a substantially salt-free compound).
  • Compound no. 3 This compound (as the enol ketone tautomer) was previously disclosed as compound A-66 in WO 2008/071405 A1 , and can in general be synthesized using the methods of preparation disclosed in either WO 2008/071405 A1 or WO 2010/136431 A9.
  • R 1 is cyclopropyl and R 2 is chlorine.
  • the compound of formula (I) is:
  • the above-shown compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound).
  • the free compound e.g. as a substantially salt-free compound.
  • Compound no. 4 This compound (as the enol ketone tautomer) was previously disclosed as Example P9 within WO 2010/136431 A9, and can in general be synthesized using the methods of preparation disclosed in either WO 2008/071405 A1 or WO 2010/136431 A9.
  • the compound of formula (I) can be present as the first or the second of the two equilibrating tautomeric forms shown below or as a mixture of both tautomeric forms.
  • the compound of formula (I), as used in the present invention, encompasses the first tautomeric form, the second tautomeric form, and a mixture of the first and second tautomeric forms:
  • an agriculturally acceptable salt of metazosulfuron is used, more particularly an agriculturally acceptable base addition salt such as an alkali metal (e.g.
  • An alkali metal (M) salt of metazosulfuron may, for example, have the following structure:
  • the metazosulfuron or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound).
  • the weight ratio of the compound of formula (I) or the salt thereof e.g. Compound no. 1 or 2, or a salt thereof, calculated as the free compound, to the
  • metazosulfuron or the salt thereof, calculated as the free compound, is:
  • the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the metazosulfuron or the salt thereof, calculated as the free compound, is:
  • the weight ratio of the compound of formula (I) or the salt thereof e.g. Compound no. 1 or 2, or a salt thereof, calculated as the free compound, to the metazosulfuron or the salt thereof, calculated as the free compound, is:
  • the herbicidal compositions of the present invention can be prepared in a variety of ways using various formulation aids, such as carriers (e.g. liquid or solid carrier), solvents and/or surface-active substances. Therefore, preferably, the herbicidal composition of the present invention is a formulation comprising a carrier (e.g. liquid or solid carrier, preferably liquid), a solvent and/or a surface-active substance.
  • a carrier e.g. liquid or solid carrier, preferably liquid
  • the herbicidal composition can be in various physical forms, for example in the form of a dustable powder (DP), a gel, a wettable powder (WP), a granule (GR) (such as an emulsifiable granule (EG) or more particularly a water-dispersible granule (WG)), a water- dispersible tablet (WT), an effervescent compressed tablet, an emulsifiable concentrate (EC), a microemulsifiable concentrate, an oil-in-water emulsion (EW), an oil flowable (e.g. a spreading oil (SO)), an aqueous dispersion (e.g.
  • DP dustable powder
  • WP wettable powder
  • GR granule
  • EG emulsifiable granule
  • WT water- dispersible tablet
  • EW oil-in-water emulsion
  • EW oil flowable
  • SO spreading oil
  • aqueous suspension concentrate SC
  • OD oily dispersion
  • SE suspo-emulsion
  • CS capsule suspension
  • soluble liquid a water-soluble concentrate (with water or a water-miscible organic solvent as carrier), an impregnated polymer film, or in another form such as a form known, for example, from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999.
  • the herbicidal composition is in the form of a wettable powder (WP), a granule (GR) (such as an emulsifiable granule (EG) or more particularly a water-dispersible granule (WG)), an emulsifiable concentrate (EC), a microemulsifiable concentrate, an oil-in-water emulsion (EW), an oil flowable (e.g. a spreading oil (SO)), an aqueous dispersion (e.g.
  • WP wettable powder
  • GR granule
  • EG emulsifiable granule
  • WG water-dispersible granule
  • EW oil-in-water emulsion
  • SO spreading oil
  • aqueous dispersion e.g.
  • aqueous suspension concentrate SC
  • OD oily dispersion
  • a soluble liquid a soluble liquid
  • a water- soluble concentrate wherein the water-soluble concentrate is with water or a water-miscible organic solvent as carrier.
  • the herbicidal composition is in the form of an emulsifiable concentrate (EC).
  • EC emulsifiable concentrate
  • the herbicidal composition of the invention can for example be used directly or, more typically, can be diluted prior to use.
  • Diluted liquid herbicidal compositions can be prepared, for example, by mixing (e.g. in a tank) the herbicidal composition of the invention with water, fertiliser(s) (e.g. liquid or granular fertiliser(s)), micronutrient(s), biological organism(s), oil and/or solvent(s); and/or by mixing the herbicidal composition of the invention with water and optionally other ingredients (typically fertiliser(s), micronutrient(s), biological organism(s), oil and/or solvent(s)).
  • fertiliser(s) e.g. liquid or granular fertiliser(s)
  • micronutrient(s) e.g. liquid or granular fertiliser(s)
  • biological organism(s) e.g., oil and/or solvent(s)
  • optionally other ingredients typically fertiliser(s), micronutrient(s), biological organism(s), oil and/or solvent
  • the herbicidal compositions can be prepared, for example, by mixing the active ingredient with one or more formulation aids.
  • the composition can e.g. be formed in the form of finely divided solids, granules, solutions, dispersions or emulsions.
  • the active ingredients can also be mixed with other formulation aids, for example finely divided solids, mineral oils, vegetable oils, modified vegetable oils, organic solvents, water, surface-active substances or combinations thereof.
  • the active ingredients can also be contained in very fine
  • microcapsules consisting of a polymer.
  • Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into their surroundings in controlled amounts (e.g. slow release).
  • Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients can be present in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the encapsulating membranes comprise, for example, natural and synthetic gums, cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art in this connection.
  • the active ingredient is present in the form of finely divided particles in a solid matrix of a base substance, but in that case the microcapsule is not encapsulated.
  • composition aids suitable for the preparation of the compositions according to the invention can include those known per se.
  • liquid carrier there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylenes carbonate, chlorobenzene, cyclo- hexane, cyclohexanol, alkyl esters of acetic acid (e.g.
  • methoxypropanol methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine,
  • octadecanoic acid octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, or higher molecular weight alcohols (i.e.
  • an alcohol having a higher molecular weight than isopropanol such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, 2-ethyl-hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, hexylene glycol, or glycerol), or A/-methyl-2-pyrrolidone, /V-octyl-2- pyrrolidone, a mixture of heavy aromatic hydrocarbons (e.g. containing a mixture of
  • naphthalene e.g. Solvesso 200TM
  • a similar liquid carrier and/or a similar solvent.
  • Water is generally the carrier of choice for the dilution of a concentrate (e.g. emulsifiable concentrate) herbicidal composition.
  • Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica (silicon dioxide), attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montomorillonite, cottonseed husks, wheatmeal, soybean flour, pumice, wood flour, ground walnut shells, lignin and/or similar materials, as described, for example, in CFR 180.1001. (c) & (d).
  • a surface-active substance can advantageously be used both in solid and in liquid herbicidal compositions, especially in those herbicidal compositions which can be diluted with a carrier prior to use.
  • Surface-active substances may be anionic, cationic, non-ionic or polymeric and they may be used as emulsifiying, wetting or suspending agents or for other purposes.
  • Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecyl- benzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, 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, polyethylene glycol esters of
  • Further formulation aids which can usually be used in the herbicidal composition include crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, anti- oxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and/or buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, anti-freezes, microbiocides, and/or liquid and/or solid fertilisers.
  • the herbicidal compositions may also comprise additional active substances, for example one or more further herbicides, herbicide safeners, plant growth regulators, fungicides and/or insecticides.
  • compositions according to the invention can additionally include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.
  • the amount of oil additive used in the composition according to the invention is generally from 0.01 to 10 %, based on the spray mixture.
  • the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared.
  • Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® (Rhone-Poulenc Canada Inc.), alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow.
  • a preferred additive contains, for example, as active components essentially 80 % by weight alkyl esters of fish oils and 15 % by weight methylated rapeseed oil, and also 5 % by weight of customary emulsifiers and pH modifiers.
  • Especially preferred oil additives comprise alkyl esters of C 8 -C 2 2 fatty acids, especially the methyl derivatives of C 12 -Ci 8 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid, being important.
  • Those esters are known as methyl laurate (CAS-1 1 1 -82-0), methyl palmitate (CAS-1 12-39-0) and methyl oleate (CAS-1 12-62-9).
  • a preferred fatty acid methyl ester derivative is Emery® 2230 and 2231 (Cognis GmbH).
  • Those and other oil derivatives are also known from the Compendium of Herbicide Adjuvants, 5th Edition, Southern Illinois University, 2000.
  • the application and action of the oil additives can be further improved by combining them with surface-active substances, such as non-ionic, anionic or cationic surfactants.
  • surface-active substances such as non-ionic, anionic or cationic surfactants.
  • suitable anionic, non-ionic and cationic surfactants are listed on pages 7 and 8 of
  • Preferred surface-active substances are anionic surfactants of the dodecyl- benzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C 12 -C 22 fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available surfactants are the Genapol types (Clariant AG). Also preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltrisiloxanes, which are commercially available e.g. as Silwet L-77®, and also perfluorinated surfactants.
  • the concentration of surface-active substances in relation to the total additive is generally from 1 to 30 % by weight.
  • oil additives that comprise or consist of mixtures of oils or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (a mixture of surfactant, 1-octanol and petroleum oil) (Syngenta AG, CH), and Actipron® (BP Oil UK Limited, GB).
  • the said surface-active substances may also be used in the herbicidal compositions alone, that is to say without oil additives.
  • an organic solvent to the oil additive/surfactant mixture can contribute to a further enhancement of action.
  • Suitable solvents are, for example, Solvesso® (ESSO) and Aromatic Solvent® (Exxon Corporation). The concentration of such solvents can be from 10 to 80 % by weight of the total weight.
  • Such oil additives which may be in admixture with solvents, are described, for example, in US-A-4 834 908.
  • a commercially available oil additive disclosed therein is known by the name MERGE® (BASF Corporation).
  • a further oil additive that is preferred according to the invention is SCORE® (Syngenta Crop Protection Canada.)
  • compositions of alkylpyrrolidones e.g. Agrimax®
  • Compositions of synthetic latices such as, for example, polyacrylamide, polyvinyl compounds or poly-1-p-menthene (e.g. Bond®, Courier® or Emerald®) can also be used.
  • Solutions that contain propionic acid, for example Eurogkem Pen-e-trate®, can also be mixed into the spray mixture as activity-enhancing agents.
  • the herbicidal compositions generally contain:
  • formulation aids e.g. a total of from 5 to 99.5%, or from 20 to 98%, or from 40% to 95%, by weight of the herbicidal composition, of: any carrier (e.g. liquid or solid carrier) (if present), any solvent (if present), any surface-active substance (if present), and any other formulation aids which may be present).
  • the formulation aid(s) preferably include(s) from 1 to 25 % by weight of a surface-active substance, e.g. one or more emulsifiers. Unless the context requires otherwise, in this specification, % by weight means % by weight of the herbicidal composition.
  • Preferred formulations have especially the following compositions:
  • Emulsifiable concentrates are:
  • active ingredient 1 to 95 %, in particular 1 to 60 % (e.g. 1 to 40 %) or 60 to 90 %
  • surface-active agent 1 to 30 %, preferably 5 to 30 % or 5 to 20 %
  • liquid carrier (and/or solvent) 1 to 90 % or 1 to 80 %, in particular 1 to 35 % or 35 to 90
  • active ingredient 0.1 to 10 %, preferably 0.1 to 5 %
  • solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
  • active ingredient 2 to 75 % or 5 to 75 %, preferably 10 to 50 %
  • surface-active agent 1 to 40 %, preferably 2 to 30 %
  • active ingredient 0.5 to 90 %, preferably 1 to 80 %
  • surface-active agent 0.5 to 20 %, preferably 1 to 15 %
  • solid carrier 5 to 95 %, preferably 15 to 90 %
  • active ingredient 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %, where the term "active ingredient” refers to the mixture of compound of formula (I) with a co- herbicide.
  • Emulsifiable concentrates a) b) c) d) active ingredient 5 % 10% 25% 50% calcium dodecylbenzene- sulfonate 6 % 8% 6% 8% castor oil polyglycol ether 4 % 4% 4%
  • Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
  • NMP (/V-methylpyrrolidone) - - 30% 10% aromatic hydrocarbon 75 % 60 %
  • the solutions are suitable for application in the form of microdrops.
  • Wettable powders a) b) c) d) active ingredient 5 % 25% 50%
  • the active ingredient is thoroughly mixed with the formulation aid(s) and the mixture is thoroughly ground in a suitable mill, yielding wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • F4. Coated granules a) b) c) active ingredient 0.1% 5% 15% highly dispersed silicic acid 0.9 % 2 % 2 % inorganic carrier 99.0 % 93 % 83 %
  • the active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier and the solvent is subsequently evaporated off in vacuo.
  • the finely ground active ingredient is applied uniformly, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • the active ingredient is mixed and ground with the formulation aid(s) and the mixture is moistened with water. The resulting mixture is extruded and then dried in a stream of air.
  • F7. Dusts a) b) c) active ingredient 0.1 % 1 % 5 % talcum 39.9 % 49 % 35 % kaolin 60.0 % 50 % 60 %
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.
  • Suspension concentrates a) b) c) d) active ingredient 3 % 10 % 25 % 50 % ethylene glycol 5 % 5 % 5 % 5 % nonylphenol polyglycol ether - 1 % 2 % -
  • the finely ground active ingredient is intimately mixed with the formulation aid(s), yielding a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
  • active ingredient in the examples mentioned above refers to the mixture of compound of formula (I) with a co-herbicide.
  • a second aspect of the present invention relates to a method of controlling weeds in crops of useful plants, which comprises applying a herbicidal composition of the invention as defined herein to the weeds and/or useful plants (e.g. flooded weeds and/or flooded useful plants) and/or to the locus (e.g. flooded locus) thereof.
  • a herbicidal composition of the invention as defined herein to the weeds and/or useful plants (e.g. flooded weeds and/or flooded useful plants) and/or to the locus (e.g. flooded locus) thereof.
  • the second aspect of the invention also relates also to a method for the control (e.g.
  • weeds in crops of useful plants which comprises treating the weeds and/or useful plants (e.g. flooded weeds and/or flooded useful plants), and/or the area under cultivation (e.g. flooded area), and/or the locus (e.g. flooded locus) thereof, with a herbicidal composition according to this invention.
  • useful plants e.g. flooded weeds and/or flooded useful plants
  • area under cultivation e.g. flooded area
  • locus e.g. flooded locus
  • the invention also relates to a herbicidal composition as defined herein, for controlling weeds in crops of useful plants (e.g. flooded plants), especially in crops of rice (e.g. flooded rice).
  • crops of useful plants e.g. flooded plants
  • crops of rice e.g. flooded rice
  • the application of the herbicidal composition is preferably post- emergence (e.g. after the emergence of the crop(s) and/or the weed(s)).
  • the crops of useful plants e.g. in which the compositions according to the invention can be used, are in particular cereals, cotton, soybeans, sugar beet, sugar cane, potatoes, plantation crops, rape (e.g. oilseed rape), maize or rice; or more particularly cotton, soybeans, sugar beet, sugar cane, potatoes, rape (e.g. oilseed rape), or rice.
  • the crops of useful plants are preferably rice, in particular indica rice (such as IR-64,
  • Ciherang Pusa e.g. Pusa-1 121 , Jiayu 293, or NK-3325 hybrid); or japonica rice (such as Koshihikari, Arborio, or Liangyou peiju e.g. Liangyou peiju PS3100).
  • the rice is preferably flooded rice.
  • the rice can for example be direct-seeded [e.g. dry-sown (dry-seeded) or wet-sown] rice; which can optionally be flooded (e.g. before or after the herbicidal composition is applied).
  • the rice is transplanted rice, which is typically flooded (e.g. before the herbicidal composition is applied).
  • Non-selective weed control might also be a possibility in some circumstances.
  • the weeds to be controlled may be monocotyledonous and/or dicotyledonous weeds, such as, for example, Echinochloa (e.g. Echinochloa crus-galli), Brachiaria (e.g. Brachiaria plantaginia), Leptochloa (e.g. Leptochloa chinensis), Digitaria, Setaria, Scirpus (e.g. Scirpus maritimus or Scirpus juncoides), Monochoria, Fimbristylis, Cyperus, Commelina, Sagittaria, Elatine, Lindernia, Ludwigia, Stellaria, Nasturtium, Agrostis, Avena, Sinapis, Lolium,
  • Echinochloa e.g. Echinochloa crus-galli
  • Brachiaria e.g. Brachiaria plantaginia
  • Leptochloa e.g. Leptochloa chin
  • the weeds to be controlled comprise: monocotyledonous weeds, and/or weeds found in rice fields e.g. rice paddy fields.
  • the weeds to be controlled comprise: Echinochloa (e.g.
  • Echinochloa crus-galli Echinochloa oryzoides, Echinochloa colona orcolonum (ECHCO), Echinochloa crus-pavonis, or Echinochloa oryzicola; or Echinochloa muricata or Echinochloa stagnina
  • Brachiaria e.g. Brachiaria plantaginia (BRAPL)
  • Leptochloa e.g. Leptochloa chinensis (LEFCH) or Leptochloa panicoides
  • Digitaria Setaria
  • Scirpus e.g.
  • Scirpus maritimus SCPMA
  • Scirpus juncoides SCPJU
  • Scirpus maritimus Scirpus fluviatilis, Scirpus pendulus, Scirpus triangulatus, or one of many other Scirpus species
  • Monochoria e.g. Monochoria vaginalis (OOVA) or Monochoria korsakovii
  • Fimbristylis e.g. Fimbristylis miliacea (FIMMI)
  • Cyperus e.g. Cyperus serotinus
  • Commelina Sagittaria, Elatine, Lindernia and/or Ludwigia
  • Schoenoplectus e.g. Schoenoplectus mucronatus or Schoenoplectus juncoides.
  • the weeds to be controlled comprise: Echinochloa (e.g. Echinochloa crus- galli (ECHCG), Echinochloa oryzoides, Echinochloa colona or colonum (ECHCO),
  • Echinochloa e.g. Echinochloa crus- galli (ECHCG), Echinochloa oryzoides, Echinochloa colona or colonum (ECHCO)
  • BRAPL Brachiaria plantaginia
  • Leptochloa e.g. Leptochloa chinensis (LEFCH) or Leptochloa panicoides
  • Scirpus e.g. Scirpus mari
  • Monochoria vaginalis (MOOVA) or Monochoria korsakovii), Fimbristylis (e.g. Fimbristylis miliacea (FIMMI)), and/or Cyperus (e.g. Cyperus serotinus).
  • MOOVA Monochoria vaginalis
  • FIMMI Fimbristylis miliacea
  • Cyperus e.g. Cyperus serotinus
  • the weeds to be controlled comprise Echinochloa, such as Echinochloa crus-galli (ECHCG), and/or Brachiaria, such as Brachiaria plantaginia (BRAPL).
  • Echinochloa such as Echinochloa crus-galli (ECHCG)
  • Brachiaria such as Brachiaria plantaginia (BRAPL).
  • the weeds to be controlled are in crops of flooded rice, especially crops of flooded transplanted rice.
  • the term "crops" is to be understood as also including crops that have been rendered tolerant to herbicides or classes of herbicides (for example ALS, GS, EPSPS, PPO, ACCase or HPPD inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • crops that have been rendered tolerant e.g. to imidazolinones, such as imazamox, by conventional methods of breeding are Clearfield® summer rape (Canola) or Clearfield® rice.
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate-resistant or glufosinate-resistant maize or rice varieties, e.g. those commercially available under the trade names RoundupReady® (glyphosate-resistant maize or rice) or LibertyLink® (glufosinate-resistant maize or rice).
  • Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to
  • Bt maize are the Bt-176 maize hybrids of NK® (Syngenta Seeds).
  • the Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins and transgenic plants able to synthesise such toxins are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529.
  • transgenic plants that contain one or more genes which code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®.
  • Plant crops and their seed material can be resistant to herbicides and at the same time also to insect feeding ("stacked" transgenic events). Seed can, for example, have the ability to express an insecticidally active Cry3 protein and at the same time be glyphosate-tolerant.
  • the term "crops" is to be understood as also including crops obtained as a result of conventional methods of breeding or genetic engineering which contain so-called output traits (e.g. improved flavour, storage stability, nutritional content).
  • Areas under cultivation are to be understood as including land where the crop plants are already growing as well as land intended for the cultivation of those crop plants.
  • each of the herbicides may vary within wide limits, and for example can depend upon the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed to be controlled, the prevailing climatic conditions, and/or other factors governed by the method of application, the time of application and/or the target crop.
  • the herbicidal composition is applied to the plants and/or the weeds, or to the locus thereof, at an application rate as defined below.
  • the application rate for the compound of formula (I) or the salt thereof is:
  • the application rate for the metazosulfuron or the salt thereof is:
  • the application rate for the compound of formula (I) or the salt thereof is:
  • the application rate for the metazosulfuron or the salt thereof is:
  • the application rate for the compound of formula (I) or the salt thereof is: from 30 to 250 g/ha, e.g. 60, 90, 120 or 240 g/ha; preferably from 50 to 180 g/ha or from 50 to 150 g/ha, e.g. 60, 90 or 120 g/ha; more preferably from 80 to 130 g/ha or from 90 to 120 g/ha, e.g. 90 or 120 g/ha;
  • the application rate for the metazosulfuron or the salt thereof is:
  • a third aspect of the present invention provides a herbicidal composition comprising:
  • R 1 is ethyl or cyclopropyl, and R 2 is chlorine or fluorine;
  • weight ratio of the compound of formula (I) or the salt thereof, calculated as the free compound, to the halosulfuron-methyl or the salt thereof, calculated as the free compound is from 30:60 to 250:3.
  • R 1 is ethyl and R 2 is chlorine, or R 1 is cyclopropyl and R 2 is fluorine.
  • an agriculturally acceptable salt of halosulfuron-methyl is used, more particularly an agriculturally acceptable base addition salt such as an alkali metal (e.g.
  • the halosulfuron-methyl or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound).
  • the weight ratio of the compound of formula (I) or the salt thereof e.g. Compound no. 1 or 2, or a salt thereof, calculated as the free compound, to the
  • halosulfuron-methyl or the salt thereof, calculated as the free compound, is:
  • a fourth aspect of the present invention relates to a method of controlling weeds in crops of useful plants, which comprises applying a herbicidal composition as defined in the third aspect of the invention to the weeds and/or useful plants (e.g. flooded weeds and/or flooded useful plants) and/or to the locus (e.g. flooded locus) thereof.
  • the preferable features of the fourth aspect of the invention are generally as described herein for the second aspect of the invention.
  • the application rate for the halosulfuron-methyl or the salt thereof is: from 3 to 60 g/ha, more preferably from 5 to 40 g/ha or from 5 to 30 g/ha, still more preferably from 10 to 20 g/ha, e.g. 10, 15 or 20 g/ha;
  • a fifth aspect of the invention provides a method of controlling Brachiaria weeds (e.g.
  • Brachiaria plantaginia BRAPL
  • flooded Brachiaria weeds in crops of useful plants
  • useful plants e.g. cotton, soybeans, sugar beet, sugar cane, potatoes, or rape (e.g. oilseed rape), or most preferably rice, e.g. flooded and/or transplanted rice
  • a compound of formula (I) or an agriculturally acceptable salt thereof preferably Compound no. 1 or 2, or a salt thereof
  • the compound of formula (I) or the salt thereof is applied at an application rate of: from 30 to 250 g/ha, e.g. 60, 90, 120 or 240 g/ha; preferably from 50 to 180 g/ha or from 50 to 150 g/ha, e.g. 60, 90 or 120 g/ha; more preferably from 80 to 130 g/ha or from 90 to 120 g/ha, e.g. 90 or 120 g/ha;
  • the compound of formula (I) or the salt thereof is not applied to the Brachiaria weeds or to the locus thereof together with (e.g. in a herbicidal composition containing) any of: fenoxasulfone, ipfencarbazone, propyrisulfuron, or /V-[2-[(4,6-dimethoxy-1 ,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1 ,1-difluoro-A/- methylmethanesulfonamide, or a salt of any of these.
  • Compound no. 1 or 2 alone appear to be herbicidally active (ca. 75-98%) against Brachiaria plantaginia, with little (0% to 5%) phytotoxicity on IR-64 indica rice, when applied by post- emergent foliar spray application as an EC formulation at an application rate of 90 or 120 g/ha of Compound no. 1 or at an application rate of 60, 90 or 120 g/ha of Compound no. 2 (see Biological Example 1 herein).
  • the herbicidal composition (and/or compound of formula (I) or salt thereof) according to any aspect of the invention described herein (above or below) can also be used in combination with one or more safeners.
  • the following mixtures with safeners especially, come into consideration: [herbicidal composition of the invention, or compound of formula (I) or salt] + a compound of
  • the herbicidal composition of the invention (or the compound of formula (I) or salt) to contain (or be mixed with) the compound of the following
  • the weight ratio of the compound of formula (I) or salt thereof e.g. Compound no. 1 or 2, or salt thereof
  • the safener e.g. the compound
  • cyprosulfamide is from 20: 1 to 1 :2, more preferably from 8: 1 to 1 :2 (e.g. 8:1 , 4: 1 or 2:1), still more preferably from 4:1 to 1 :1 , e.g. 4:1 or 2:1.
  • a herbicidal composition comprising:
  • R 1 is ethyl or cyclopropyl, and R 2 is chlorine or fluorine;
  • metazosulfuron or halosulfuron-methyl or an agriculturally acceptable salt thereof preferably metazosulfuron or a salt thereof
  • the weight ratio of the compound of formula (I) or salt thereof e.g. Compound no. 1 or 2, or salt thereof
  • the safener e.g. the compound
  • cyprosulfamide is from 20:1 to 1 :2, more preferably from 8:1 to 1 :2 (e.g. 8: 1 , 4:1 or 2:1 ), still more preferably from 4:1 to 1 :1 , e.g. 4:1 or 2:1.
  • the rate of application of safener in relation to herbicide depends largely on the method of application.
  • the ratio of the compound of formula (I) or salt (calculated as the free compound) to the safener is generally from 100: 1 to 1 : 10, preferably from 20: 1 to 1 :1.
  • from 1 to 200 g of safener/ha, preferably from 5 to 100 kg of safener/ha is generally applied.
  • the amounts of any oil additive which might be employed are generally from 0.01 to 2 %, based on the spray mixture.
  • the oil additive can, for example, be added to the spray tank in the desired concentration after the spray mixture has been prepared.
  • Emulsogen EL 360TM Emulsifier castor oil 36 moles of
  • Emulsifiable concentrate (EC) procedure (used for Formulation Examples 1, 2 and 3)
  • the solvent(s) are added to the vessel, followed by the emulsifiers.
  • the mixture is rolled until a clear solution is obtained.
  • the active ingredient is then added, and rolled till a clear solution is obtained.
  • Formulation Example 4 Emulsifiable concentrate (EC) formulation containing Compound no. 1 and metazosulfuron Formulation Example 4 is a variation of Formulation Example 1 in which, in the emulsifiable concentrate (EC), in addition to Compound no. 1 , there is present metazosulfuron, and wherein Compound no. 1 and the metazosulfuron are present in the following weight ratios:
  • Formulation Example 4 weight ratio of Compound no. 1 to metazosulfuron is: 60:100, 90:100, 120:100, 60:90, 90:90, 120:90, 60:60, 90:60, 120:60, 60:45, 90:45, 120:45, 60:22, 90:22, or 120:22.
  • Formulation Example 5 is a variation of Formulation Example 2 in which, in the emulsifiable concentrate (EC), in addition to Compound no. 2, there is present metazosulfuron, and wherein Compound no. 2 and the metazosulfuron are present in the following weight ratios: Formulation Example 5: weight ratio of Compound no. 2 to metazosulfuron is: 60:100,
  • Formulation Example 6 is a variation of Formulation Example 3 in which, in the emulsifiable concentrate (EC), in addition to Compound no. 3, there is present metazosulfuron, and wherein Compound no. 3 and the metazosulfuron are present in the following weight ratios:
  • Formulation Example 6: weight ratio of Compound no. 3 to metazosulfuron is: 60:100, 90:100, 120:100, 60:90, 90:90, 120:90, 60:60, 90:60, 120:60, 60:45, 90:45, 120:45, 60:22, 90:22, or 120:22.
  • Test plants (rice and weeds) were grown in a glasshouse (greenhouse) under hot and humid conditions, and the application of various herbicides and herbicidal mixtures were tested: - by post-emergence foliar spray application to rice or weeds (see Biological Example 1 below); and
  • Biological Example 1 Glasshouse test for post-emergence foliar spray application of mixtures of compounds of formula (I) with either metazosulfuron or halosulfuron- methyl, to rice or weeds (test 106)
  • Herbicide Application Post-emergence foliar spray application, 300 L/ha, single replicate
  • Rice Rice seeds, variety IR-64 (an indica type of rice), were sown in seed trays. After about 7-8 days the resulting plants were transplanted into 6-inch-diameter circular pots with no holes containing Boughton loam soil, which was then was saturated with water replicating swampy conditions. The herbicide application took place when the rice was at the 3-leaf 1 -tiller growth stage - this was 9 days after transplantation.
  • Echinochloa crus-galli EHCG - 2-3 leaves;
  • BRAPL Brachiaria plantaginia
  • Compound nos. 1 and 2 were each tested at 15, 60, 90 & 120 g/ha on the weeds, and 60, 90,120 & 240 g/ha on the rice; and were each tested alone or in combination with: 45g/ha metazosulfuron (technical sample, i.e.
  • Rice seeds of variety IR-64 (an indica type of rice), were sown in seed trays. After about 7-8 days the resulting plants were transplanted into 6-inch-diameter circular pots with no holes containing Boughton loam soil. The loam soil in the rice pots was saturated with water replicating swampy conditions. The post-emergence foliar spray application of the herbicide(s) to the rice took place when the rice was at the 3-leaf 1 -tiller growth stage - this was 9 days after transplantation and about 17 days after sowing.
  • Echinochloa crus-galli Echinochloa crus-galli
  • Leptochloa chinensis LEFCH
  • Brachiairia plantaginea BRAPL
  • Scirpus juncoides SPJU
  • Monochoria vaginalis MOOVA
  • test herbicidal solutions were prepared by mixing the appropriate aliquots of the test substance and adjuvant (Adsee at 0.2%v/v) in de-ionised water to give the desired treatment concentration.
  • DAA herbicide Application
  • etazosulfuron which was pure active ingredient (labelled as Technical' in the following results table), was prepared for the glasshouse test by dissolving in 10.56% Emulsogen EL TM (castor oil ethoxylate, CAS Registry number 61791-12-6), 42.22% AZ-methylpyrrolidone and 42.22% dipropylene glycol mono-ethyl ether to give a stock solution containing 5% of the test substance and 95% of (Emulsogen ELTM, ⁇ -methylpyrrolidone and dipropylene glycol mono-ethyl ether).
  • Emulsogen EL TM castor oil ethoxylate, CAS Registry number 61791-12-6
  • 42.22% AZ-methylpyrrolidone 42.22% dipropylene glycol mono-ethyl ether
  • Example 2 (Technical) 15 45 NT 65 0 55 100 95
  • Compound no. 1 alone achieved good control of ECHCG (control at 60g/ha), some activity on BRAPL (approx 80% at 90g/ha), and negligible activity on the remaining 3 weeds tested.
  • Addition of 45g/ha metazosulfuron to Compound no. 1 caused a slight reduction in ECHCG activity, a slight improvement to BRAPL activity (at low Compound no. 1 rates), and a large improvement to SCPJU and MOOVA activity.
  • Compound no. 2 alone achieved good control of ECHCG, marginally better than Compound no. 1 , also reasonable control of BRAPL (92% at 120g/ha, again better than Compound no. 1), and also control of SCPJU at 120g/ha.
  • Compound no. 2 was safer to rice and more active on the weeds (ECHCG, BRAPL and SCPJU) than Compound no. 1 , under the conditions tested.
  • the weed-control spectrum of Compound no. 1 and Compound no. 2 is increased and improved by inclusion of each of the two sulfonyl urea mixture partners, but no mixtures fully controlled LEFCH.
  • Rice seeds, variety IR-64 (an indica type of rice), were sown in seed trays. After about 7 days the resulting plants were transplanted as 3 groups of 2 plants, into 6-inch-diameter circular pots containing a loam soil (here, Boughton loam (clay, pH 7.0, 5.9% OM)) saturated with water, replicating swampy conditions. These were grown on for a further 9 days in a glasshouse bay (under the following climatic conditions: 30/20°C day/night; 18/6 hours light/dark; 75% humidity).
  • a loam soil here, Boughton loam (clay, pH 7.0, 5.9% OM)
  • Echinochloa crus-galli Echinochloa crus-galli
  • FIMMI Fimbristylis miliacea
  • SCP A Scirpus maritimus
  • MOOVA Monochoria vaginalis
  • ECHCG section 4 of trays: 0.5 to 1 leaves (early growth stage of ECHCG)
  • test substance metazosulfuron which was pure active ingredient (labelled as Technical' in the following results table), was prepared for testing by dissolving in 10.56% Emulsogen ELTM (castor oil ethoxylate, CAS Registry number 61791 -12-6), 42.22% A/-methylpyrrolidone and 42.22% dipropylene glycol mono-ethyl ether to give a stock solution containing 5% of the test substance and 95% of (Emulsogen ELTM, /V-methylpyrrolidone and dipropylene glycol mono-ethyl ether).
  • Application of the test substances was made by pipetting the required amount of the test solution or the test formulation gently into the flood water of the appropriate pot or
  • test plants were then grown on in the same glasshouse conditions, and watered twice daily keeping the flood water at a depth of ca. 2 - 3 cm.
  • Example 2 I) 60 90 NT 70 98 100 90 90 90
  • Example 2 1) 120 60 15 65 98 100 85 99 halo-
  • NC results not considered.
  • the results on the weeds for 120 g/ha of Compound no. 2 and 15 g/ha halosulfuron-methyl were clearly not consistent with other similar treatments, suggesting there may have been an error in chemical formulation for this specific treatment, and so the rice and weeds results have been removed and not considered where NC is shown.

Abstract

L'invention porte sur une composition herbicide comprenant : (a) un composé de formule (I) ou un sel acceptable en agriculture de celui-ci : dans laquelle R1 représente le groupe éthyle ou cyclopropyle et R2 représente l'atome de chlore ou de fluor ; et (b) du métazosulfuron ou un sel acceptable en agriculture de celui-ci. De préférence, R1 est le groupe éthyle et R2 est l'atome de chlore ; ou R1 est le groupe cyclopropyle et R2 est l'atome de fluor. L'invention porte également sur une composition herbicide comprenant : le composé de formule (I) ou un sel de celui-ci et de l'halosulfuron-méthyle ou un sel de celui-ci, le rapport pondéral du composé de formule (I) à l'halosulfuron-méthyle étant de 30:60 à 250:3. Les compositions herbicides servent de préférence à lutter contre des mauvaises herbes dans des cultures de plantes utiles (par exemple de riz), en particulier pour lutter contre Echinochloa, Brachiaria et/ou d'autres mauvaises herbes. L'invention porte également sur un procédé de lutte contre des mauvaises herbes Brachiaria dans des cultures de plantes utiles, qui comprend l'application du composé de formule (I) ou d'un sel acceptable en agriculture de celui-ci sur les mauvaises herbes Brachiaria ou le lieu de celles-ci.
PCT/GB2011/000946 2011-06-23 2011-06-23 Composition herbicide comprenant un herbicide pyranedione et un herbicide sulfonylurée WO2012175899A1 (fr)

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PCT/GB2011/000946 WO2012175899A1 (fr) 2011-06-23 2011-06-23 Composition herbicide comprenant un herbicide pyranedione et un herbicide sulfonylurée
ARP120102217A AR086701A1 (es) 2011-06-23 2012-06-21 Composicion herbicida que comprende un herbicida piranodionico y un herbicida sulfonilureico
UY0001034153A UY34153A (es) 2011-06-23 2012-06-22 ?composición herbicida que comprende un herbicida piranodiónico y un herbicida sulfonilureico?.
TW101122382A TW201313125A (zh) 2011-06-23 2012-06-22 包含哌喃二酮除草劑及磺醯脲除草劑之除草組合物

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WO2017220680A1 (fr) 2016-06-21 2017-12-28 Battelle Uk Limited Compositions herbicides contenant de la sulfonylurée liquide et du sel de li
EP3387904A1 (fr) 2014-12-22 2018-10-17 Mitsui AgriScience International S.A./N.V. Compositions herbicides contenant du sulfonylurea liquide
EP3900535A1 (fr) 2020-04-24 2021-10-27 Battelle UK Limited Composition herbicide de sulfonylurée liquide

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EP3549443A1 (fr) 2016-06-21 2019-10-09 Battelle UK Limited Compositions liquides herbicides contenant un sel de sulfonylurée et de li
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