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WO2019030088A1 - Mélanges herbicides comprenant du l-glufosinate et leur utilisation dans des cultures céréalières - Google Patents

Mélanges herbicides comprenant du l-glufosinate et leur utilisation dans des cultures céréalières Download PDF

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Publication number
WO2019030088A1
WO2019030088A1 PCT/EP2018/070930 EP2018070930W WO2019030088A1 WO 2019030088 A1 WO2019030088 A1 WO 2019030088A1 EP 2018070930 W EP2018070930 W EP 2018070930W WO 2019030088 A1 WO2019030088 A1 WO 2019030088A1
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Prior art keywords
esters
salts
methyl
sodium
glyphosate
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Inventor
Christian Winter
Markus Gewehr
Ryan Louis NIELSON
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BASF SE
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BASF SE
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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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives 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
    • A01N43/18—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 sulfur as the ring hetero atom
    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/74—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 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Definitions

  • Herbicidal mixtures comprising L-glufosinate and their use in cereal cultures
  • the present invention relates to herbicidal mixture comprising L-glufosinate and and a herbicidal compound II selected from clethodim, clodinafop, clodinafop-propargyl, cycloxydim, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, pinoxaden, 4- (2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (CAS 953075-27-9) and its esters, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-6-methoxy-2-methyl-3(2H)-pyridazinone (CAS 1384437-51 -7) and its
  • Tolerant or resistant cereal varieties provide the option to use herbicides, which are originally not selective in respective tolerant or resistant cereal in addition to conventional weed control system.
  • herbicides which are originally not selective in respective tolerant or resistant cereal in addition to conventional weed control system.
  • Examples are glyphosate, glufosinate and imidazolinones (e.g., imazamox) which can not only be used for pre-plant burn-down both in conventional cereal cultures and cereal plants that are tolerant against herbicides including glufosinate and/or the other mentioned herbicides; but which can also achieve effective weed control by post- emergence application in tolerant cereal cultures.
  • Glufosinate is a broad-spectrum herbicide that controls most grass and broadleaf herbicide species; however, there are a few tough to control species or resistant biotypes that it does not fully control. Another challenge is the duration of action, or the degradation rate of the herbicide. Furthermore, changes in the sensitivity of harmful plants, which may occur upon prolonged use of the herbicides or within a geographical limited area, must also be taken into consideration. The resulting loss of action against individu- al plants can sometimes compensated for to a certain extent by higher application rates of the herbicides. However, there is always a demand for methods to achieve the herbicidal effect with lower application rates of active compounds to reduce not only the amount of an active compound required for application, but also the amount of formulation auxiliaries. Thus, low application rates are for economic and environmental reasons an object eco-friendliness of the herbi- cide treatment.
  • One possibility for improving the use profile of a herbicide is the combination of the herbicide in question with one or more other active compounds which have the desired additional properties.
  • the combined use of a plurality of active compounds may lead to phenomena of a chemical, physical and biological incompatibility (e.g. instability of a coformulation, decomposition of an active compound or antagonism in the biological action of the active compounds).
  • finding effective glufosinate combinations with an additional herbicide faces the challenge that in many instances the effectiveness of such combinations is not satisfactory and high application rates are still required to achieve an acceptable weed control.
  • the persistence of the herbicidal activity of the mixture should be sufficiently long in order to achieve control of the weeds over a sufficient long time period thus allowing a more flexible application.
  • the mixtures should also show an accelerated action on harmful plants and not affect the growth of the cereal plant.
  • Glufosinate is a racemate of two enantiomers, out of which only one shows sufficient herbicidal activity (see e.g. US 4265654 and JP92448/83). Even though various methods to prepare L- glufosinate (and respective salts) are known, the mixtures known in the art do not point at the stereochemistry, meaning that the racemate is present (e.g. WO 2003024221 , WO2009141367, WO2013154396, DE 19815820).
  • mixtures of L-glufosinate or its salt and the herbicidal compound II show enhanced herbicide action against undesirable vegetation in pre-plant burn-down prior to planting of conventional cereal plants and cereal plants that are tolerant against herbicides including glufosinate and in post-emergence use in cereals which are suitable for the se- lective use of such mixtures, and/or show superior compatibility with cereals which are suitable for the selective use of such mixtures, i.e.
  • Cereals are barley, wheat, rye, oat, triticale, preferably wheat.
  • the present invention relates to herbicidal mixtures of
  • a herbicidal compound II selected from clethodim, clodinafop, clodinafop-propargyl, cy- cloxydim, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxa- prop-P-ethyl, pinoxaden, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)- pyridazinone (CAS 953075-27-9) and its esters, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-6- methoxy-2-methyl-3(2H)-pyridazinone (CAS 1384437-51 -7) and its esters, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P
  • Glufosinate [common name of DL-4-[hydroxyl(methyl)phosphinoyl]-DL-homoalaninate] and its salts such as glufosinate ammonium and its herbicidal acitivity have been described e.g. by F. Schwerdtle et al. Z. convincedr. Wunsch, 1981 , Sonderheft IX, pp. 431 -440. Racemic glufosinate and its salts are commercially available, e.g. from Bayer CropScience under the tradenames BastaTM and LibertyTM.
  • L-Glufosinate also called glufosinate-P
  • (2S)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid (CAS Reg. No. 35597-44-5).
  • Relevant salts of L-glufosinate are L-glufosinate-ammonium (also called glufosinate-P-ammonium), which is ammonium (2S)-2-amino-4- (methylphosphinato)butyric acid (CAS Reg. No.
  • L-glufosinate-sodium also called glufosinate-P-sodium
  • (2S)-2-amino-4-(methylphosphinato)butyric acid CAS Reg. No. 70033-13-5
  • L-glufosinate-potassium also called glufosinate-P-potassium
  • L-Glufosinate as used in the present invention comprises more than 70% by weight of the L- enantiomer; preferably more than 80% by weight of the L-enantiomer; more preferably more than 90% of the L-enantiomer, most preferably more than 95% of the L-enantiomer and can be prepared as referred to above.
  • the abovementioned invention relates to herbicidal mixtures as described above, wherein L-glufosinate comprises more than 70% by weight of the L-enantiomer.
  • L-Glufosinate can be prepared according to methods known in the art, e.g. as described in WO2006/104120, US5530142, EP0127429 and J. Chem. Soc. Perkin Trans. 1 , 1992, 1525- 1529.
  • the weight ratio of compound I to compound II is preferably from 1000: 1 to 1 : 500, 400:1 to 1 :40, more preferably 500:1 to 1 :250, in particular from 200:1 to 1 :20, even more preferably from 100:1 to 1 :10, most preferably 50:1 to 1 :5.
  • mixtures are preferred, which contain L-glufosinate-ammonium or L-glufosinate- sodium as L-glufosinate salts or L-glufosinate as free acid.
  • mixtures which contain L-glufosinate-ammonium as L-glufosinate salt.
  • Preferred compounds II are clethodim, clodinafop, clodinafop-propargyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, pinoxaden, 4-(2,6- diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (CAS 953075-27-9) and its esters, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-6-methoxy-2-methyl-3(2H)-pyridazinone (CAS 1384437-51 -7) and its esters, sethoxydim, tralkoxydim, prosulfocarb, triallate, amidosulfuron, chlorsulfuron, flupyrsulfuron, flupyrsulfuron-methyl-so
  • preferred mixtures of the present invention are mixtures of L-glufosinate-ammonium or L- glufosinate-sodium as L-glufosinate salts or L-glufosinate as free acid and a herbicidal compound II selected from the group consisting of clethodim, clodinafop, clodinafop-propargyl, diclo- fop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, pinoxa- den, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (CAS 953075- 27-9) and its esters, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-6-methoxy-2-methyl-3(2H)- pyridazinone
  • pyraflufen II-78 4-(2,6-diethyl-4- II-93 pyrafluf en-ethyl II-79 methylphenyl)-5-hydroxy- 2,6-dimethyl-3(2H)- oxyfluorfen II-80
  • More preferred mixtures of the present invention are mixtures of L-glufosinate-ammonium or L- glufosinate-sodium as L-glufosinate salts or L-glufosinate as free acid and at least one compound II selected from the group consisting of clodinafop, clodinafop-propargyl, diclofop, diclo- fop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, pinoxaden, 4-(2,6- diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (CAS 953075-27-9) and its esters, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-6-methoxy-2-methyl-3(2H)-pyridazinone (CAS 1384437-51 -7) and
  • inventive mixtures can further contain one or more insecticides, fungicides, herbicides.
  • the inventive mixtures can be converted into customary types of agrochemical mixtures, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • mixture types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wetable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g.
  • the mixtures are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkylated
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the inventive mixtures on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, biological or synthetic waxes, and cellulose ethers.
  • 10-60 wt% of an inventive mixture and 5-15 wt% wetting agent e.g. alcohol alkoxylates
  • a wetting agent e.g. alcohol alkoxylates
  • the active substance dissolves upon dilution with water.
  • an inventive mixture and 1 -10 wt% dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylben- zenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzene- sulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • 20-60 wt% of an inventive mixture are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1 - 2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1 - 2 wt% thickener e.g. xanthan gum
  • an inventive mixture 50-80 wt% of an inventive mixture are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water- dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active sub- stance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 50-80 wt% of an inventive mixture are ground in a rotor-stator mill with addition of 1 -5 wt% dis- persants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dis- persants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • an inventive mixture In an agitated ball mill, 5-25 wt% of an inventive mixture are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • an inventive mixture 5-20 wt% are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamicallystable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of an inventive mixture, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of an inventive mixture according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
  • diphenylmethene-4,4'- diisocyanatae are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of pol- yurea microcapsules.
  • the monomers amount to 1-10 wt%. The wt% relate to the total CS mixture.
  • Dustable powders (DP, DS)
  • an inventive mixture are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
  • solid carrier e.g. finely divided kaolin
  • an inventive mixture is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
  • solid carrier e.g. silicate
  • organic solvent e.g. aromatic hydrocarbon
  • the mixtures types i) to xii) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% color- ants.
  • auxiliaries such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% color- ants.
  • the resulting agrochemical mixtures generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow- ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the mixtures in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
  • Application can be carried out before or during sowing.
  • Methods for applying the inventive mixtures and mixtures thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • the inventive mixtures or the mixtures thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the inventive mixtures comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the inventive mixtures in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the mixture according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemi- cal mixture is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical mixture according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to- use spray liquor are applied per hectare of agricultural useful area.
  • inventive mixtures provide excellent pre-plant burn-down, pre- and post-emergence control of weeds in cereals which are suitable for the selective use of the inventive mixtures, including cereal that is tolerant to herbicides including glufosinate.
  • the compounds present in the inventive mixtures can be applied for pre-plant burn- down (to control emerged weeds prior to planting, pre-emergence (before the emergence of undesirable vegetation) or post-emergence (i.e., during and/or after emergence of the undesirable vegetation).
  • the invention relates to a method of an inventive mixture for controlling undesirable vegetation in cereals, which are suitable for the selective use of such mixtures and which comprises applying the compounds present in the inventive mixtures to a locus of planted crops where undesirable vegetation occurs or might occur.
  • the application is done before the emergence of undesirable vegetation or during and/or after emergence of the undesirable vegetation.
  • the application can be done after seeding of the cereals or during and/or after emergence of the cereals.
  • locus means the area in which the vegetation or plants are growing or will grow, typically a field.
  • undesirable vegetation As used herein, the terms “undesirable vegetation”, “undesirable species”, “undesirable plants”, “harmful plants”, “undesirable weeds”, or “harmfull weeds” are synonyms.
  • the active compounds present in the inventive mixtures can be applied simultaneously or in succession, where undesirable vegetation may occur.
  • compounds present in the inventive mixtures are formulated jointly or separately and applied jointly or separately, and, in the case of separate application, in which order the application takes place. It is only necessary, that the compounds present in the inventive mixtures are applied in a time frame, which allows simultaneous action of the active ingredients on the undesirable plants.
  • the inventive mixtures have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants.
  • the inventive mixtures also act efficiently on perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs and which are difficult to control.
  • the inventive mixtures are suitable for controlling a large number of harmful plants in agricultural crops, including monocotyledonous weeds, in particular annual weeds such as gramineous weeds (grasses) including Echinochloa species such as barnyardgrass (Echinochloa crusgalli var.
  • Poa species such as Poa annua or Poa trivialis L., Puccinellia distans, Rottboellia cochinchinensis, Sclerochloa kengiana (Ohwi) Tzvel., Trichloris crinita, Urochloa or Brachiaria species such as Brachiaria decumbens, Brachiaria plantaginea, Brachiaria platyphylla, Urochloa panicoides, Urochloa ramosa and the like.
  • Both L-glufosinate alone as well as the inventive mixtures are also suitable for controlling a large number of dicotyledonous weeds, in particular broad leaf weeds including Polygonum species such as wild buckwheat (Polygonum convolvolus), Polygonum pensilvanicum, Polygonum persicaria or prostrate knotweed (Polygonum aviculare), Amaranthus species such as pigweed (Amaranthus retroflexus), Palmer amaranth (Amaranthus palmeri), tall waterhemp (Amaranthus tuberculatus or Amaranthus rudis), redroot pigweed (Amaranthus retroflexus), green amaranth (Amaranthus hybridus), purple amaranth (Amaranthus lividus), prickly amaranth (Amaranthus spinosus) or Amaranthus quitensis, Chenopodium species such as common lambsquarters (Chenopodium album L.), Chenopodium serotinum or
  • Both L-glufosinate alone as well as the inventive mixtures are also suitable for controlling a large number of annual and perennial sedge weeds including Cyperus species such as purple nutsedge (Cyperus rotundus L), yellow nutsedge (Cyperus esculentus L), hime-kugu (Cyperus brevifolius H.), sedge weed (Cyperus microiria Steud), rice flatsedge (Cyperus iria L), Cyperus difformis, Cyperus difformis L, Cyperus esculentus, Cyperus ferax, Cyperus flavus, Cyperus iria, Cyperus lanceolatus, Cyperus odoratus, Cyperus rotundus, Cyperus serotinus Rottb., Eleo- charis acicularis, Eleocharis kuroguwai, Fimbristylis dichotoma, Fimbristylis miliace
  • Both L-glufosinate alone as well as the inventive mixtures are also suitable for controlling weeds that are resistant to commonly used herbicides such as, for example, weeds that are resistant to glyphosate, weeds that are resistant to auxin inhibitor herbicides such as e. g. 2,4-D or dicam- ba, weeds that are resistant to photosynthesis inhibitors such as e. g. atrazine, weeds that are resistant to ALS inhibitors such as e. g. sulfonylureas, imidazolinones or triazolopyrimidines, weeds that are resistant to ACCase inhibitors such as e. g.
  • clodinafop clethodim or pinoxaden or weeds that are resistant to protoporphyrinogen-IX-oxidase inhibitors such as e. g. sulfentra- zone, flumioxazine, fomesafen or acifluorfen, for example the weeds that are listed in the International Survey of Resistant Weeds
  • Rapistrum rugosum Rorippa indica, Rotala indica, Rotala pusilla, Rumex dentatus, Sagittaria guayensis, Sagittaria pygmaea, Sagittaria trifolia
  • Schoenoplectus fluviatilis Schoenoplectus juncoides
  • Schoenoplectus wallichii Sida spinosa, Silene gallica, Sinapis alba, Sisymbrium thel- lungii, Sorghum bicolor
  • mice Micranthos, Cirsium arvense, Commelina diffusa, Echinochloa crus-pavonis, Soliva sessilis and Sphenoclea zeylanica, HPPD inhibitor resistant Amaranthus palmeri and Amaranthus rudis, PPO inhibitor resistant Acalypha australis, Amaranthus hybridus, Amaranthus palmeri, Amaranthus retroflexus, Amaranthus rudis, Ambrosia artemisifolia, Avena fatua, Conyza sumatrensis, Descurainia sophia, Euphorbia heterophylla and Senecio vernalis, carotenoid biosynthesis inhibitor resistant Hydrilla verticillata, Raphanus raphanistrum, Senecio vernalis and Sisymbrium orientale, VLCFA inhibitor resistant Alopecurus myosuroides, Avena fatua and Echinochloa crus-galli.
  • the compounds of the inventive mixtures are applied to the soil surface before germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely.
  • the active compounds of the inventive mixtures are applied post-emergence to the green parts of the plants, growth likewise stops drastically a very short time after the treatment and the weed plants remain at the growth stage of the point of time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the cereal plants, is eliminated at a very early point in time and in a sustained manner.
  • the active compounds of the inventive mixtures can be used jointly or in succession. They can also conveniently be combined with further herbicide treatments to treatment combinations that ensure a more complete or long-lasting weed control, or to ensure control of weeds that are resistant against certain herbicides through combined action of mutiple herbicides with different modes of action.
  • the active compounds of the inventive mixtures and further herbicides can be used in any of the treatment combinations outlined below that consist of pre-plant burn down, pre-emergence and post-emergence and treatments. These treatment combinations can be particularly suitable if the cereal crop is tolerant to the action of one or more herbicides present in the treatment combination, including tolerance that is a result of breeding and/or genetic modification.
  • Such tolerant plants include glufosinate tolerant wheat; glyphosate tolerant wheat; wheat and barley that is tolerant to imidazolinone herbicides (e. g. imazamox, imazapyr; Clearfield® wheat and Clearfield barley); wheat that is tolerant to ACCase inhibitors (e. g.
  • PPO herbicides e. g. carfentra- zone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, sulfentrazone.
  • the following active compounds of the inventive mixtures and further herbicides are particularly suitable as pre-plant burn-down weed control components in such treatment combinations: L- Glufosinate, L-glufosinate ammonium, L-glufosinate sodium, glyphosate, glyphosate dime- thylammonium, glyphosate potassium, glyphosate isopropylammonium, paraquat, trifludimoxazin, saflufenacil, 2,4-D, 2,4-D choline salt, dicamba, dicamba ethanolamine salt, dicamba di- glycolamine salt, dicamba potassium and dicamba BAPMA salt (i. e. dicamba N,N-bis(3- aminopropyl)methylamine salt).
  • active compounds of the inventive mixtures and further herbicides are particularly suitable as pre-emergence weed control components in such treatment combinations: Prosul- focarb, triallate, chlorotoluron, isoproturon, saflufenacil, trifludimoxazin, 2-[(2,4- dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (CAS 81777-95-9), pendimethalin, triflu- ralin, flufenacet, pyroxasulfone, cinmethylin.
  • the following active compounds of the inventive mixtures and further herbicides are particularly suitable for post-emergence weed control components in such treatment combinations: L- Glufosinate, L-glufosinate ammonium, L-glufosinate sodium, glyphosate, glyphosate dime- thylammonium, glyphosate potassium, glyphosate isopropylammonium, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, pinoxaden, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6- dimethyl-3(2H)-pyridazinone (CAS 953075-27-9) and its esters, 4-(2,6-dieth
  • the active compounds of the inventive mixtures have an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds
  • the tolerant, or cross-tolerant, cereals are damaged only to a minor extent, or not at all.
  • the inventive mixtures are suitable for controlling a large number of harmful plants in cereals.
  • inventive mixtures are also suitable for controlling a large number of harmful plants in tolerant cereals, i.e. tolerance against glyphosate, glufosinate or imidazolinones (such as imazamox, imazapic, imazapyr or imazethapyr).
  • tolerant cereals includes also (cereal) plants which have been modified by mutagenesis, genetic engineering or breeding and mutation selection techniques in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • tolerant cereals are known in the art, for example, wheat events comprising tolerance are for example, but not excluding others, MON71800 (event code: MON-71800-3, gene: cp4 epsps (aroA:CP4), trade name: Roundup ReadyTM wheat), AP205CL (gene: als (mutant), trade name: Clearfield Wheat), AP602CL (gene: als (mutant), trade name: Clearfield Wheat), BW255-2, BW238-3 (gene: als (mutant), trade name: Clearfield Wheat), BW7 (gene: als (mutant), trade name: Clearfield Wheat), Teal 1 1A (gene: als (mutant), trade name: Clearfield Wheat) and SWP965001 (gene als (mutant)).
  • MON71800 event code: MON-71800-3, gene: cp4 epsps (aroA:CP4)
  • trade name: Roundup ReadyTM wheat AP205CL (gene: als (mutant), trade
  • the glufosinate tolerant cereal plant is a non-transgenic plant, in particular a cereal plant, wherein glufosinate toleranance is generated by breeding techniques.
  • the glufosinate tolerant plant is a non-transgenic plant, in particular a plant, wherein glufusinate toleranance is generated by breeding techniques and the plant is wheat.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific "event", which is referred to by a specific event name. Glufosinate tolerance can been created by using mutagenesis as well as using genetic engineering.
  • inventive mixtures can be applied in conventional manner by using techniques as skilled person is familiar with.
  • Suita- ble techniques include spraying, atomizing, dusting, spreading or watering.
  • the type of application depends on the intended purpose in a well known manner; in any case, they should ensure the finest possible distribution of the active ingredients according to the invention.
  • the inventive mixtures are applied to locus mainly by spraying, in particular foliar spraying of an aqueous dilution of the active ingredients of the mixture.
  • Application can be carried out by customary spraying techniques using, for example, water as carrier and spray liquor rates of from about 10 to 2000 l/ha or 50 to 1000 l/ha (for example from 100 to 500 l/ha).
  • Application of the inventive mixtures by the low-volume and the ultra-low-volume method is possible, as is their application in the form of microgranules.
  • the required application rate of the mixture of the pure active compounds depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the mixture is used and on the application method.
  • the rate of application of L-glufosinate is usually from 50 g/ha to 3000 g/ha and preferably in the range from 100 g/ha to 2000 g/ha or from 200 g/ha to 1500 g/ha of active substance (a.i.), and the rate of application of the secod herbicida compound II is from 1 g/ha to 2000 g/ha and preferably in the range from 5 g/ha to 1500 g/ha, more preferably from 25 g/ha to 900 g/ha of active substance (a.i.).
  • Synergism can be described as an interaction where the combined effect of two or more com- pounds is greater than the sum of the individual effects of each of the compounds.
  • the presence of a synergistic effect in terms of percent control, between two mixing partners (X and Y) can be calculated using the Colby equation (Colby, S. R., 1967, Calculating Synergistic and Antagonistic Responses in Herbicide Combinations, Weeds, 15, 21 -22):
  • the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate.
  • the seeds of the test plants were sown separately for each species and/or resistant biotype.
  • the active ingredients which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
  • test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10 - 25°C or 20 - 35°C, respectively.
  • the test period extended to 20 days after treatment. During this time, the plants were tended, and their response to the individ- ual treatments was evaluated. The evaluation was carried out by using a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth. Data shown are the mean of two replications.
  • Trifludimoxazin 500 g/l SC formulation
  • 2,4-D dimethylammonium salt 500 g/l SL formulation (concentration calculated for 2,4-D acid)
  • Dicamba dimethylammonium salt 480 g/l SL formulation (concentration calculated for dicamba acid)
  • Bicyclopyrone 5 % EC formulation
  • Dimethenamid-P 720 g/l EC formulation
  • Example 1 Post emergence treatment with the mixture of L-glufosinate with saflufenacil
  • Example 3 Post emergence treatment with the mixture of L-glufosinate with pyroxasulfone
  • Example 5 Post emergence treatment with the mixture of L-glufosinate with dicamba dime- thylammonium salt

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Abstract

La présente invention concerne des mélanges herbicides et leur procédés et utilisations dans la lutte contre la végétation indésirable dans les céréales telles que l'orge, le blé, le seigle, l'avoine et le triticale, y compris les plantes céréalières tolérantes au glufosinate, le mélange herbicide comprenant du L-glufosinate et un composé herbicide II sélectionné parmi les suivants : cléthodim, clodinafop, clodinafop-propargyle, cycloxydim, diclofop, diclofop-méthyle, fénoxaprop, fénoxaprop-éthyle, fénoxaprop-P, fénoxaprop-P-éthyle, pinoxaden, 4-(2,6-diéthyl-4-méthylphenyl)-5-hydroxy-2,6-diméthyl-3(2H)-pyridazinone (CAS 953075- 27-9) et ses esters, 4-(2,6-diéthyl-4-méthylphenyl)-5-hydroxy-6-méthoxy-2-méthyl-3(2H)- pyridazinone (CAS 1384437-51-7) et ses esters, quizalofop, quizalofop-éthyle, quizalofoptéfuryle, quizalofop-P, quizalofop-P-éthyle, quizalofop-P-téfuryle, séthoxydim, tralkoxydim, prosulfocarb, triallate, amidosulfuron, chlorsulfuron, flupyrsulfuron, flupyrsulfuron-méthyl-sodium, iodosulfuron, iodosulfuron-méthyl-sodium, iofensulfuron,iofensulfuron-sodium, mésosulfuron, metsulfuron, metsulfuron-méthyle, sulfosulfuron, thifensulfuron, thifensulfuron-méthyle, tribénuron, tribénuron-méthyle, tritosulfuron, imazaméthabenz, imazaméthabenz-méthyle, imazamox, imazamox ammonium,imazapic, imazapic ammonium,imazapyr, imazapyr isopropyl ammonium,imazaquine, imazéthapyr, imazéthapyr ammonium, flumetsulam, florasulam, pyroxsulam, flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, thiencarbazone-méthyle, atrazine, metribuzine, chlorotoluron, isoproturon, bromoxynil et ses sels et esters, ioxynil et ses sels et esters, bentazone, bentazone-sodium, carfentrazone, carfentrazone-éthyle, oxyfluorfen, pyraflufen, pyraflufen-éthyle, saflufénacil, trifludimoxazine, diflufenican, flurtamone, picolinafen, bicyclopyrone, fenquinotrione, pyrasulfotole, topramézone, glyphosate, glyphosate diméthylammmonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-trimésium (sulfosate), 2-[(2,4-dichlorophenyl)méthyl]-4,4-diméthyl-3-isoxazolidinone (CAS 81777-95-9), pendiméthaline, trifluraline, acétochlor, diméthenamide, diméthenamide-P, métazachlor, métolachlor, S-métolachlor, flufénacet, pyroxasulfone, 2,4-D et ses sels et esters, aminopyralide et ses sels tels que l'aminopyralide-diméthylammonium, l'aminopyralide-tris(2- hydroxypropyl)ammonium et ses esters, clopyralide et ses sels et esters, dicamba et ses sels et esters, fluroxypyr, fluroxypyr-butométhyle, fluroxypyr-meptyle, MCPA et ses sels et esters, mécoprop-P et ses sels et esters, picloram et ses sels et esters, quinclorac, quinclorac diméthylammonium, quinmérac, triclopyr et ses sels et esters, diflufenzopyr, diflufenzopyr-sodium et cinméthyline.
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WO2021151743A1 (fr) 2020-01-31 2021-08-05 Basf Se Combinaisons herbicides comprenant du glufosinate et de la trifludimoxazine
US11122807B2 (en) 2017-08-09 2021-09-21 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and a second herbicide
CN114041470A (zh) * 2021-11-29 2022-02-15 陕西上格之路生物科学有限公司 一种含二氯异噁草酮的除草组合物
WO2022078972A1 (fr) 2020-10-12 2022-04-21 Basf Se Combinaison herbicide comprenant du glufosinate, du saflufénacil et de la trifludimoxazine
EP4000400A1 (fr) * 2020-11-17 2022-05-25 Basf Se Combinaison d'herbicides comprenant du glufosinate, du saflufenacil et de la trifludimoxazine
US11350631B2 (en) 2017-08-09 2022-06-07 Basf Se Herbicidal mixtures comprising l-glufosinate or its salt and at least one VLCFA inhibitor
US11363818B2 (en) 2017-08-09 2022-06-21 Basf Se Herbicidal mixtures comprising L-glufosinate and their use in soybean cultures
CN114903047A (zh) * 2021-02-10 2022-08-16 四川利尔作物科学有限公司 包含光合系统ⅱ抑制剂和合成激素类化合物的除草组合物及其应用
CN115104622A (zh) * 2021-03-22 2022-09-27 江苏七洲绿色化工股份有限公司 一种精草铵膦与苯唑草酮的复配组合物
CN115104623A (zh) * 2021-03-22 2022-09-27 江苏七洲绿色化工股份有限公司 除草组合物及其制备方法
CN115104624A (zh) * 2021-03-22 2022-09-27 江苏七洲绿色化工股份有限公司 一种精草铵膦与甲咪唑烟酸的复配组合物
US11477985B2 (en) 2017-08-09 2022-10-25 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and at least one photosynthesis inhibitor
US11589591B2 (en) 2017-08-09 2023-02-28 Basf Se Herbicidal mixtures comprising L-glufosinate and their use in corn cultures
US11666052B2 (en) 2017-08-09 2023-06-06 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and at least one bleacher herbicide
US11666053B2 (en) 2017-08-09 2023-06-06 Basf Se Herbicidal mixtures comprising L-glufosinate and their use in cotton cultures
CN117256622A (zh) * 2023-09-27 2023-12-22 江苏七洲绿色化工股份有限公司 一种含精草铵膦的复配除草剂
WO2023247971A1 (fr) * 2022-06-24 2023-12-28 Upl Mauritius Limited Combinaisons herbicides et procédé de lutte contre la végétation indésirable
WO2024057027A1 (fr) * 2022-09-16 2024-03-21 Upl Mauritius Limited Combinaison herbicide, composition et procédé de lutte contre les mauvaises herbes l'utilisant
WO2024057016A1 (fr) * 2022-09-14 2024-03-21 Upl Mauritius Limited Composition herbicide et procédé d'application pour le désherbage chimique
US12041935B2 (en) 2017-08-09 2024-07-23 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and at least one protoporphyrinogen-IX oxidase inhibitor
EP4171224A4 (fr) * 2020-06-29 2024-07-31 Monsanto Technology LLC Mélanges de l-glufosinate et d'herbicides à base d'auxine
US12262715B2 (en) 2020-02-05 2025-04-01 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and at least one protoporphyrinogen-IX oxidase inhibitor

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