WO2019030086A2 - Mélanges herbicides comprenant du l-glufosinate et leur utilisation dans les cultures de colza - Google Patents

Mélanges herbicides comprenant du l-glufosinate et leur utilisation dans les cultures de colza Download PDF

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WO2019030086A2
WO2019030086A2 PCT/EP2018/070928 EP2018070928W WO2019030086A2 WO 2019030086 A2 WO2019030086 A2 WO 2019030086A2 EP 2018070928 W EP2018070928 W EP 2018070928W WO 2019030086 A2 WO2019030086 A2 WO 2019030086A2
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glufosinate
saflufenacil
salts
esters
ethyl
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PCT/EP2018/070928
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WO2019030086A3 (fr
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Christian Winter
Markus Gewehr
Ryan Louis NIELSON
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Basf Se
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Priority to AU2018314499A priority patent/AU2018314499A1/en
Publication of WO2019030086A2 publication Critical patent/WO2019030086A2/fr
Publication of WO2019030086A3 publication Critical patent/WO2019030086A3/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
    • 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
    • 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
    • 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 canola cultures
  • the present invention relates to herbicidal mixture comprising L-glufosinate and and a herbicidal compound II selected from clethodim, cycloxydim, fenoxaprop, fenoxaprop-ethyl, fenoxaprop- P, fenoxaprop-P-ethyl, fluazifop, f I uazif op-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, halox- yfop-methyl, haloxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,
  • Tolerant or resistant canola varieties provide the option to use herbicides, which are originally not selective in respective tolerant or resistant canola in addition to conventional weed control system.
  • herbicides which are originally not selective in respective tolerant or resistant canola in addition to conventional weed control system.
  • One example is glufosinate, which can not only be used for pre-plant burn-down both in conventional canola, and canola that is tolerant against herbicides including glufosinate; but which can also achieve effective weed control by post- emergence application in glufosinate tolerant canola.
  • 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.
  • 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 canola 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).
  • a herbicidal compound II selected from clethodim, cycloxydim, fenoxaprop, fenoxaprop- ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop- P-tefuryl, tepraloxydim, ethametsulfuron, ethametsulfuron-methyl, tritosulfuron, imaza
  • 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.
  • Compounds II as well as their pesticidal action and methods for producing them are generally known, for example in the Pesticide Manual V5.2 (ISBN 978 1 901396 85 0) (2008-201 1 ) amongst other sources.
  • Compound II-83 is known from EP 1 122244.
  • Compound II-84 is known from WO2016/1201 16.
  • Compounds II-85, II-86, II-87, II-88, II-90 and 11-91 are known from
  • 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.
  • the present present invention relates to herbicidal mixtures of
  • a herbicidal compound II selected from the group consisting of clethodim, cycloxydim, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, tepraloxydim, ethametsulfuron, ethametsulfuron- methyl, tritos
  • compounds II are clethodim, cycloxydim, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop- ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, tepraloxydim, ethametsulfuron, ethametsulfuron-methyl, imazamox, imazamox ammoni
  • compounds II are clethodim, cycloxydim, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, halox- yfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop- ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, tepraloxydim, ethametsulfuron, ethametsulfuron-methyl, imazamox, imazamox, ima
  • compounds II are clethodim, cycloxydim, tepraloxydim, ethametsul- furon, ethametsulfuron-methyl, imazapyr, imazapyr isopropylammoniumtribenuron-methyl, flo- rasulam, cyanazine, bromoxynil and its salts and esters, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, ethalfluralin, pendimethalin, triallate, propyzamide, carbetamide, metazachlor, napropamide, 2,4-D and its salts and esters
  • compounds II are imazapyr, tribenuron-methyl, florasulam; carfentrazone-ethyl, trifludimoxazin, sulfentrazone, pyraflufen-ethyl, tiafenacil, compounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92; mesotrione, topramezone, bromoxynil, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate; II-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H- indol-6-yl)-2-pyridinecarboxylic acid (CAS 1628702-28-2) and its salts and esters, 2,4-D and its salts and esters, dicamba and its salts and esters, aminopyralid, pic
  • compounds II are carfentrazone-ethyl, trifludimoxazin, sulfentrazone, pyraflufen-ethyl, tiafenacil, compounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92; mesotrione, topramezone, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate; II- 93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (CAS
  • the compounds II in the mixtures of the invention are selected from the group consisting of imazapyr, tribenuron-methyl and florasulam.
  • the compounds II in the mixtures of the invention are selected from the group consisting of carfentrazone-ethyl, trifludimoxazin, sulfentrazone, pyraflufen-ethyl, tiafenacil, compounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92.
  • the compounds II in the mixtures of the invention are selected from the group consisting of mesotrione, topramezone, bromoxynil, tembotrione, pyrasulfotole, bicyclopy- rone, tolpyralate; preferably selected from the group of mesotrione, topramezone, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate.
  • the compounds II in the mixtures of the invention are selected from the group consisting of 11-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2- pyridinecarboxylic acid (CAS 1628702-28-2) and its salts and esters, 2,4-D and its salts and esters, dicamba and its salts and esters, aminopyralid, picloram and fluroxypyr.
  • the compounds II in the mixtures of the invention are selected from the group consisting of pendimethalin, ethalfluralin, triallate.
  • 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, cycloxydim, fenoxaprop, fenoxaprop- ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop
  • Preferred mixtures 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, cycloxydim, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop- methyl, haloxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-
  • the mixtures 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, cycloxydim, tepraloxydim, ethametsul- furon, ethametsulfuron-methyl, imazapyr, imazapyr isopropylammoniumtribenuron-methyl, flo- rasulam, cyanazine, bromoxynil and its salts and esters, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, mesotrione, tembotrione,
  • Preferred mixtures 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 imazapyr, tribenuron-methyl, florasulam; carfentrazone-ethyl, trifludimoxazin, sulfentrazone, pyraflufen-ethyl, tiafenacil, compounds II-83, II-84, II-85, II-86, II-87, II-88, II- 89, II-90, 11-91 , II-92; mesotrione, topramezone, bromoxynil, tembotrione, pyrasulfotole, bicyclo- pyrone, tolpyralate; H-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-
  • Preferred mixtures 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 carfentrazone-ethyl, trifludimoxazin, sulfentrazone, pyraflufen-ethyl, tiafenacil, compounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92; mesotrione, topramezone, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate; N-93: 4-amino-3-chloro-5- fluoro-6-(7-f!uoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (CAS 1628702-28-
  • the mixtures 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 select- ed from the group consisting of imazapyr, tribenuron-methyl and florasulam.
  • the mixtures 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 carfentrazone-ethyl, trifludimoxazin, sulfentra- zone, pyraf I uf en-ethyl, tiafenacil, compounds 11-83, 11-84, 11-85, 11-86, 11-87, 11-88, 11-89, 11-90, II- 91 , II-92.
  • a herbicidal compound II selected from the group consisting of carfentrazone-ethyl, trifludimoxazin, sulfentra- zone, pyraf I uf en-ethyl, tiafenacil, compounds 11-83, 11-84, 11-85, 11-86, 11
  • the mixtures 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 mesotrione, topramezone, bromoxynil, tembotrione, pyrasul- fotole, bicyclopyrone, tolpyralate; preferably selected from the group of mesotrione, topramezone, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate.
  • a herbicidal compound II selected from the group consisting of mesotrione, topramezone, bromoxynil, tembotrione, pyrasul- fotole, bicyclopyrone, tolpyralate; preferably selected from the group of mesotrione, topramezone, tembotrione, pyrasulfotole, bicyclopyrone, tol
  • the mixtures 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 II-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H- indol-6-yl)-2-pyridinecarboxylic acid (CAS 1628702-28-2) and its salts and esters, 2,4-D and its salts and esters, dicamba and its salts and esters, aminopyralid, picloram and fluroxypyr.
  • a herbicidal compound II selected from the group consisting of II-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H- indol-6-yl)-2-pyridinecarboxylic acid (CAS 1628702-28-2) and its salts and esters, 2,4-D
  • the mixtures 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 pendimethalin, ethalfluralin, triallate.
  • aminopyralid- Compound Abbreviation Compound Abbreviation dimethylammonium mesotrione II-62 aminopyralid-tris(2- II-36 alachlor II-63 hydroxypropyl)ammonium metolachlor II-64 and its esters S-metolachlor II-65 clopyralid and its salts and II-37 carbetamide II-66 esters 2,4-D and its salts and esII-67 dicamba and its salts and II-38 ters
  • II-83 ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4- tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6; S-3100).
  • II-84 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221 -16-9)
  • 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 clethodim, cycloxydim, haloxyfop, haloxyfop- methyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, tepraloxydim, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, triben
  • the 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.
  • 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 WP
  • SP WS
  • DP DS
  • pressings e.g. BR, TB, DT
  • gran- ules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g. LN
  • gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • 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, al- kylated 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, al-
  • 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 colloid, 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 con- densed 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.
  • Exam- pies of 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 sus- pension. 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
  • water ad 100 wt% to give a fine active substance sus- pension.
  • Dilution with water gives a stable suspension of the active substance.
  • binder e.g. polyvinylalcohol
  • 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 substance.
  • 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% colorants.
  • 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 powders (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 propaga- tion 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.
  • the inventive mixtures provide excellent pre-plant burn-down, pre- and post-emergence control of weeds in canola, including canola 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 canola, including canola that is tolerant to herbicides including glufosinate, 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 canola or during and/or after emergence of the canola.
  • Canola is also called oil seed rape.
  • locus means the area in which the vegetation or plants are growing or will grow, typically a field.
  • the active com- pounds 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 mix- tures also act efficiently on perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs and which are difficult to control.
  • it does not matter whether the compounds of the inventive mixtures are applied before sowing, pre-emergence or post-emergence. Pre-plant burn-down, post-emergence application, or early pre-sowing or pre- emergence application, are preferred.
  • 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 an- nua 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 (Ama- ranthus 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 serotin
  • Sysimbrium species Solanum species such as black nightshade (Solanum nigrum), Xanthium species, Veronica species such as Veronica polita, Viola species, common chickweed (Stellaria media), velvetleaf (Abutilon theophrasti), Sesbania species such as Sesbania exaltata, Ses- bania herbacea or hemp sesbania (Sesbania exaltata Cory), Anoda cristata, Bidens species such as Bidens frondosa or Bidens pilosa, Brassica kaber, Capsella species such as Capsella media or Capsella bursa-pastoris, Centaurea cyanus, Galeopsis tetrahit, Galium aparine, Heli- anthus annuus, Desmodium tortuosum, Kochia scoparia, Mercurialis annua, Myosotis arvensis, Papaver rhoeas, Raphanus species such as wild radish (R
  • 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 Inter- national 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 and further herbicides can be used in any of the treatment combinations outlined below that consist of pre-plant burn down, pre-emergence/pre-plant volunteer canola control, post-emergence and pre-harvest desiccation treatments.
  • treatment combinations can be particularly suitable if the canola 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 canola, glyphosate tolerant canola, canola that is tolerant to imid- azolinone herbicides (e. g. imazamox, imazapyr), HPPD herbicides (e. g. topramezone, meso- trione, tembotrione, pyrasulfotole, bicyclopyrone), auxin herbicides (e. g. 2,4-D, dicamba) and/or PPO herbicides (e. g. carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, sulfentra- zone).
  • imid- azolinone herbicides e. g. imazamox, imazapyr
  • HPPD herbicides e. g. topramezone, meso- trione, tembotrione, pyrasulfotole, bi
  • 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).
  • the following active compounds of the inventive mixtures and further herbicides are particularly suitable as pre-emergence weed control components or components for pre-plant control of volunteer canola in such treatment combinations: Pendimethalin, trifluralin, ethalfluralin, triallate, trifludimoxazin, saflufenacil, sulfentrazone, isoxaflutole, bicyclopyrone, tembotrione, topramezone, topramezone/bromoxynil, pyrasulfotole and mesotrione.
  • 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, imazamox, imazapyr, tribenuron-methyl, florasulam, ethametsulfuron-methyl, carfentrazone-ethyl, saflufenacil, trifludimoxazin, sulfentrazone, mesotrione, topramezone, bicyclopyrone, tolpyralate, tembotrione, pyrasulfotole, aminopyralid, aminopyralid triisopropanolamine salt, clopyralid, clopyralid ethanolamine salt, picloram, piclor
  • active compounds of the inventive mixtures and further herbicides are particularly suitable as pre-harvest desiccation components in such treatment combinations: L-Glufosinate, L-glufosinate ammonium, L-glufosinate sodium, glyphosate, glyphosate dimethylammonium, glyphosate potassium, glyphosate isopropylammonium, carfentrazone-ethyl, saflufenacil, triflu- dimoxazin and sulfentrazone.
  • the treatment combinations 4.1 to 4.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and clethodim.
  • the treatment combinations 5.1 to 5.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and clethodim.
  • the treatment combinations 21.1 to 21.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and halox- yfop-P-ethyl.
  • the treatment combinations 22.1 to 22.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate and quizalofop-P- tefuryl.
  • treatment combinations 42.1 to 42.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium, quinclorac dimethylammonium and cycloxydim.
  • the treatment combinations 64.1 to 64.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac dime- thylamine salt and haloxyfop-P-ethyl.
  • treatment combinations 65.1 to 65.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quinclorac dimethylamine salt and haloxyfop-P-ethyl.
  • treatment combinations 66.1 to 66.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium, quinclorac dimethylamine salt and haloxyfop-P-ethyl.
  • treatment combinations 71.1 to 71.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quin- clorac dimethylamine salt and quizalofop-P-tefuryl.
  • the abovementioned properties and advantages are necessary under practical weed control conditions to keep the glufosinate tolerant canola free from undesired competing plants and thus to guarantee and/or increase the yields from the qualitative and quantitative point of view.
  • These novel combinations markedly exceed the technical state of the art with a view to the properties described.
  • the active compounds of the inventive mixtures have an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds
  • the tolerant, or cross-tolerant, glufosinate tolerant canola 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 glufosinate tolerant canola
  • glufosinate tolerant canola includes also (canola) 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.
  • 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 re- ferred 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 has been created by using mutagenesis as well as using genetic engineering.
  • Transgenic canola events comprising glufosinate tolerance genes are for example, but not excluding others, HCN10 (Topas 19/2) (event code: , gene: bar, e.g. commercially available as Liberty LinkTM IndependenceTM), HCN28 (T45) (event code: ACS-BN008-2, gene: pat, e.g. commercially available as InVigorTM Canola), HCN92 (Topas 19/2 (event code: ACS-BN007-1 , gene: bar, e.g.
  • canola plants of the invention include those plants which have been subjected to genetic modifications other than glufosinate tolerance by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific other classes of herbicides, such as PPO inhibitors (e. g. saflufenacil, trifludimoxazin), AHAS inhibitors (e. g. imidazo- linones such as imazamox, imazapyr); auxinic herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (e. g.
  • PPO inhibitors e. g. saflufenacil, trifludimoxazin
  • AHAS inhibitors e. g. imidazo- linones such as imazamox, imazapyr
  • auxinic herbicides such as dicamba or 2,4-D
  • EPSPS inhibitors such as glyphosate
  • glutamine synthetase (GS) inhibitors such as glufosinate
  • lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors such as "dims” ⁇ e.g., cycloxydim, sethoxydim, clethodim, or tepraloxydim), "fops” ⁇ e.g.
  • clodinafop diclofop, fluazifop, haloxyfop, or quizalofop
  • dens such as pinoxaden
  • oxynil ⁇ i.e. bromoxynil or ioxynil
  • canola plants of the invention can be made resistant to multiple classes of herbicides through multiple genetic modifications, such as for example resistance to both glyphosate and dicamba; glyphosate and2,4-D; glyphosate and glufosinate; glyphosate and HPPD inhibitors; glyphosate and AHAS inhibitors; glufosinate and AHAS inhibitors; glyphosate, glufosinate and AHAS inhibitors; glyphosate, glufosinate and HPPD inhibitors; glufosinate and HPPD inhibitors; glyphosate, glufosinate, dicamba and HPPD inhibitors; glyphosate, dicamba and glufosinate; glyphosate and PPO inhibitors; glufosinate and PPO inhibitors;
  • glyphosate, glufosinate and PPO inhibitors glyphosate, dicamba and PPO inhibitors; glyphosate, 2,4-D and PPO inhibitors; glyphosate, dicamba, glufosinate and PPO inhibitors; glyphosate, 2,4-D, glufosinate and PPO inhibitors; glyphosate, PPO inhibitors and HPPD inhibitors; glufosinate, HPPD inhibitors and PPO inhibitors; glyphosate, glufosinate, HPPD inhibitors and PPO inhibitors; glyphosate, dicamba, HPPD inhibitors and PPO inhibitors; glyphosate, 2,4-D, HPPD inhibitors and PPO inhibitors; glyphosate, dicamba, glufosinate, HPPD inhibitors and
  • PPO inhibitors glyphosate, 2,4-D, glufosinate, HPPD inhibitors and PPO inhibitors; glyphosate, glufosinate, AHAS inhibitors and HPPD inhibitors; glufosinate, AHAS inhibitors and HPPD inhib- itors; glyphosate, glufosinate, dicamba, AHAS inhibitors and HPPD inhibitors; glyphosate, dicamba, AHAS inhibitors and glufosinate; glyphosate, AHAS inhibitors and PPO inhibitors; glufosinate, AHAS inhibitors and PPO inhibitors; glyphosate, glufosinate, AHAS inhibitors and PPO inhibitors; glyphosate, glufosinate, AHAS inhibitors and PPO inhibitors; glyphosate, glufosinate, AHAS inhibitors and PPO inhibitors; glyphosate, dicamba, AHAS inhibitors and
  • herbicide resistance technologies are, for example, described in Pest Management Sci- ence (at volume, year, page): 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein.
  • canola plants of the invention may also be tolerant to herbicides having other modes of action, for example, chlorophyll/carotenoid pigment inhibitors, cell membrane disrupters, photosynthesis inhibitors, cell division inhibitors, root inhibitors, shoot inhibitors, and combinations thereof.
  • herbicides having other modes of action for example, chlorophyll/carotenoid pigment inhibitors, cell membrane disrupters, photosynthesis inhibitors, cell division inhibitors, root inhibitors, shoot inhibitors, and combinations thereof.
  • Such additional tolerance traits may be expressed, e.g.: as mutant or wildtype PPO proteins, as mutant AHASL proteins, mutant ACCase proteins, mutant EPSPS proteins, or mutant glutamine synthetase proteins; or as mutant native, inbred, or transgenic aryloxyalkanoate dioxygenase (AAD or DHT), haloarylnitrilase (BXN), 2,2-dichloropropionic acid dehalogenase (DEH), glypho- sate-N- acetyltransferase (GAT), glyphosate decarboxylase (GDC), glyphosate oxidoreductase (GOX), glutathione-S-transferase (GST), phosphinothricin acetyltransferase (PAT or bar), or CYP450s proteins having an herbicide-degrading activity.
  • AAD or DHT transgenic aryloxyalkanoate dioxy
  • Glufosinate tolerant canola plants hereof can also be stacked with other traits including, but not limited to, pesticidal traits such as Bt Cry and other proteins having pesticidal activity toward coleopteran, lepidopteran, nematode, or other pests; nutrition or nutraceutical traits such as modified oil content or oil profile traits, high protein or high amino acid concentration traits, and other trait types known in the art.
  • pesticidal traits such as Bt Cry and other proteins having pesticidal activity toward coleopteran, lepidopteran, nematode, or other pests
  • nutrition or nutraceutical traits such as modified oil content or oil profile traits, high protein or high amino acid concentration traits, and other trait types known in the art.
  • the inventive mixtures can be applied in conventional manner by using techniques as skilled person is familiar with. Suitable techniques include spraying, atomizing, dusting, spreading or watering. The type of applica- tion 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 individual 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.
  • Compound II-83 5 % EC formulation (Compound 11-16: ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate)
  • 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 2 Post emergence treatment with the mixture of L-glufosinate with Compound II-83 (ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetate)
  • Example 8 Post emergence treatment with the mixture of L-glufosinate with bicyclopyrone

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Abstract

La présente invention concerne des mélanges herbicides et leurs procédés et utilisations pour lutter contre la végétation indésirable dans le colza tolérant au glufosinate, le mélange herbicide comprenant du L-glufosinate et un composé herbicide II choisi parmi les suivants : cléthodim, cycloxydim, fénoxaprop, fénoxaprop-éthyle, fénoxaprop-P, fénoxaprop-P-éthyle, fluazifop, fluazifop-butyle, fluazifop-P, fluazifop-P-butyle, haloxyfop, haloxyfop-méthyle, haloxyfop-P, haloxyfop-P-méthyle, propaquizafop, quizalofop, quizalofop-éthyle, quizalofop-téfuryle, quizalofop-P, quizalofop-P-éthyle, quizalofop-P-téfuryle, tépraloxydim, éthametsulfuron, éthametsulfuron-méthyle, tritosulfuron, imazaméthabenz, imazaméthabenz-méthyle, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazéthapyr, imazéthapyr ammonium, tribenuron-méthyle, florasulam, cyanazine, bromoxynil et ses sels et esters, bentazone, bentazone-sodium, pyridate, carfentrazone, carfentrazone-éthyle, saflufénacil, sulfentrazone, trifludimoxazin, pyraflufén-éthyle, flumioxazin, tiafénacil, picolinafen, clomazone, mésotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, éthalfluraline, pendiméthaline, triallate, trifluraline, propyzamide, carbétamide, acétochlor, alachlor, butachlor, diméthachlor, métazachlor, métolachlor, S-métolachlor, napropamide, napropamide-M, 2,4-D et ses sels et esters, aminopyralide et ses sels tels que l'aminopyralide-diméthylammonium, aminopyralide-tris(2-hydroxypropyl)ammonium et ses esters, clopyralide et ses sels et esters, dicamba et ses sels et esters, quinmérac, diflufenzopyr, diflufenzopyr-sodium, cinméthylin, diméthénamid, diméthenamide-P, quinclorac, quinclorac diméthylammonium, topramézone, séthoxydim, péthoxamide, clopyralide, picloram, fluroxypyr et d'autres composés.
PCT/EP2018/070928 2017-08-09 2018-08-02 Mélanges herbicides comprenant du l-glufosinate et leur utilisation dans les cultures de colza WO2019030086A2 (fr)

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019195495A1 (fr) * 2018-04-04 2019-10-10 Dow Agrosciences Llc Lutte contre les mauvaises herbes par applications d'herbicides à base d'acide pyridine carboxylique et d'inhibiteurs de 4-hydroxyphényl-pyruvate dioxygénase (hppd)
WO2019195496A1 (fr) * 2018-04-04 2019-10-10 Dow Agrosciences Llc Lutte améliorée contre les mauvaises herbes par applications d'herbicides à base d'acide pyridine carboxylique et d'inhibiteurs d'acétyl coenzyme a caroxylase (accase)
US10555528B1 (en) 2019-03-20 2020-02-11 Sumitomo Chemical Company, Limited Herbicidal composition and method for controlling weeds
EP3675635A4 (fr) * 2017-09-01 2021-05-19 Dow Agrosciences LLC Compositions herbicides contenant des acides pyridine carboxyliques ou des dérivés de ceux-ci, avec du glyphosate ou du glufosinate, ou des dérivés de ceux-ci
WO2021151743A1 (fr) 2020-01-31 2021-08-05 Basf Se Combinaisons herbicides comprenant du glufosinate et de la trifludimoxazine
WO2021151738A1 (fr) 2020-01-31 2021-08-05 Basf Se Combinaisons herbicides comprenant du glufosinate et de l'epyrifenacil
US11122807B2 (en) 2017-08-09 2021-09-21 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and a second herbicide
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
WO2022152728A1 (fr) * 2021-01-15 2022-07-21 Bayer Aktiengesellschaft Compositions herbicides
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
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
WO2024052665A1 (fr) * 2022-09-07 2024-03-14 Upl Mauritius Limited Combinaison herbicide, composition et procédé de lutte contre les mauvaises herbes l'utilisant

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4265654A (en) 1977-12-28 1981-05-05 Meiji Seika Kaisha Ltd. Herbicidal compositions
EP0127429A2 (fr) 1983-05-27 1984-12-05 Meiji Seika Kaisha Ltd. Procédé de préparation de dérivés optiquement actifs d'acide((amino-3-carboxy-3)-propyl-1)phosphinique
US5530142A (en) 1988-05-27 1996-06-25 Hoechst Aktiengesellschaft Process for the preparation of phosphorus-containing L-amino acids and their esters and N-derivatives
DE19815820A1 (de) 1998-04-08 1999-10-14 Hoechst Schering Agrevo Gmbh Synergistische herbizide Mittel auf Basis von phosphorhaltigen Blattherbiziden, Imidazolinonen und Wuchsstoffherbiziden
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
WO2003024221A1 (fr) 2001-09-14 2003-03-27 Basf Aktiengesellschaft Melanges herbicides a base de 3-phenyluraciles
WO2006104120A1 (fr) 2005-03-29 2006-10-05 Meiji Seika Kaisha Ltd. Procede de production de l'acide l-2-amino-4-(hydroxymethylphosphinyl)butanoique
WO2009141367A2 (fr) 2008-05-21 2009-11-26 Basf Se Composition herbicide comprenant du glyphosate, du glufosinate ou leurs sels
WO2013154396A1 (fr) 2012-04-12 2013-10-17 Dongbu Farm Hannong Co., Ltd. Composition herbicide comprenant un composé uracile comme ingrédient actif
WO2014151005A1 (fr) 2013-03-15 2014-09-25 Dow Agrosciences Llc 4-amino-6-(hétérocycle)picolinates et 6-amino-2-2(hétérocycle) pyrimidine-4-carboxylates et leur utilisation comme herbicides
WO2016120116A1 (fr) 2015-01-29 2016-08-04 Basf Se Phénylpyridines herbicides
WO2017202768A1 (fr) 2016-05-24 2017-11-30 Basf Se Uracil-pyridines herbicides
WO2018108695A1 (fr) 2016-12-16 2018-06-21 Basf Se Phényltriazolinones herbicides

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19836700A1 (de) * 1998-08-13 2000-02-17 Hoechst Schering Agrevo Gmbh Herbizide Mittel für tolerante oder resistente Getreidekulturen
TR200100618T2 (tr) * 1998-08-13 2001-10-22 Aventis Cropscience Gmbh Toleranslı ve dayanıklı mısır kültürleri için herbisitler
DE19836726A1 (de) * 1998-08-13 2000-02-17 Hoechst Schering Agrevo Gmbh Herbizide Mittel für tolerante und resistente Rapskulturen
DE19836660A1 (de) * 1998-08-13 2000-02-17 Hoechst Schering Agrevo Gmbh Herbizide Mittel für tolerante oder resistente Sojakulturen
US6369001B1 (en) * 1999-08-11 2002-04-09 Monsanto Technology, Llc Microemulsion coformulation of a graminicide and a water-soluble herbicide
JP5433120B2 (ja) * 1999-09-30 2014-03-05 モンサント テクノロジー エルエルシー 向上した安定性を有するパッケージミックス農薬組成物
JP5584452B2 (ja) * 2008-12-11 2014-09-03 石原産業株式会社 ベンゾイルピラゾール系化合物を含有する除草性組成物
CN103025167A (zh) * 2010-05-21 2013-04-03 拜耳知识产权有限责任公司 用于耐受性或抗性稻栽培种的除草剂
WO2011144685A1 (fr) * 2010-05-21 2011-11-24 Bayer Cropscience Ag Agents herbicides pour cultures de céréales tolérantes ou résistantes
WO2011144683A1 (fr) * 2010-05-21 2011-11-24 Bayer Cropscience Ag Agents herbicides pour cultures de colza tolérantes ou résistantes
EP2571366A1 (fr) * 2010-05-21 2013-03-27 Bayer Intellectual Property GmbH Agents herbicides pour cultures de maïs tolérantes ou résistantes
CN102027992A (zh) * 2010-12-21 2011-04-27 利尔化学股份有限公司 非耕地、果园用增效除草组合物
EP2524602A1 (fr) * 2011-05-20 2012-11-21 Bayer CropScience AG Agent herbicide pour cultures de soja tolérantes ou résistantes
WO2013149999A1 (fr) * 2012-04-05 2013-10-10 Basf Se Formulations liquides solubles de sels d'ammonium de quinclorac
CN103053610A (zh) * 2012-12-29 2013-04-24 广东中迅农科股份有限公司 草铵膦和芳氧基苯氧基丙酸类除草剂的除草组合物
CN103053609B (zh) * 2012-12-29 2014-12-31 广东中迅农科股份有限公司 草铵膦和吡啶羧酸类除草剂的除草组合物
EP3079470B1 (fr) * 2013-12-10 2020-01-22 Dow AgroSciences LLC Désherbage herbicide synergique à partir de combinaisons de 2,4-d-choline et glufosinate
AR103410A1 (es) * 2015-01-15 2017-05-10 Basf Se Combinación herbicida que comprende saflufenacil y glufosinato
US10045532B2 (en) * 2015-07-07 2018-08-14 Valent U.S.A., Corporation Synergistic herbicidal mixtures for glyphosate-resistant volunteer corn control
CN105660687A (zh) * 2016-03-01 2016-06-15 江苏七洲绿色化工股份有限公司 一种精草铵膦与麦草畏的复配组合物

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4265654A (en) 1977-12-28 1981-05-05 Meiji Seika Kaisha Ltd. Herbicidal compositions
EP0127429A2 (fr) 1983-05-27 1984-12-05 Meiji Seika Kaisha Ltd. Procédé de préparation de dérivés optiquement actifs d'acide((amino-3-carboxy-3)-propyl-1)phosphinique
US5530142A (en) 1988-05-27 1996-06-25 Hoechst Aktiengesellschaft Process for the preparation of phosphorus-containing L-amino acids and their esters and N-derivatives
DE19815820A1 (de) 1998-04-08 1999-10-14 Hoechst Schering Agrevo Gmbh Synergistische herbizide Mittel auf Basis von phosphorhaltigen Blattherbiziden, Imidazolinonen und Wuchsstoffherbiziden
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
WO2003024221A1 (fr) 2001-09-14 2003-03-27 Basf Aktiengesellschaft Melanges herbicides a base de 3-phenyluraciles
WO2006104120A1 (fr) 2005-03-29 2006-10-05 Meiji Seika Kaisha Ltd. Procede de production de l'acide l-2-amino-4-(hydroxymethylphosphinyl)butanoique
WO2009141367A2 (fr) 2008-05-21 2009-11-26 Basf Se Composition herbicide comprenant du glyphosate, du glufosinate ou leurs sels
WO2013154396A1 (fr) 2012-04-12 2013-10-17 Dongbu Farm Hannong Co., Ltd. Composition herbicide comprenant un composé uracile comme ingrédient actif
WO2014151005A1 (fr) 2013-03-15 2014-09-25 Dow Agrosciences Llc 4-amino-6-(hétérocycle)picolinates et 6-amino-2-2(hétérocycle) pyrimidine-4-carboxylates et leur utilisation comme herbicides
WO2016120116A1 (fr) 2015-01-29 2016-08-04 Basf Se Phénylpyridines herbicides
WO2017202768A1 (fr) 2016-05-24 2017-11-30 Basf Se Uracil-pyridines herbicides
WO2018108695A1 (fr) 2016-12-16 2018-06-21 Basf Se Phényltriazolinones herbicides

Non-Patent Citations (19)

* Cited by examiner, † Cited by third party
Title
"McCutcheon's, Vol.1: Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES
"Pesticide Manual", vol. 5.2, 2008
"Technical Monograph", May 2008, CROPLIFE INTERNATIONAL, article "Catalogue of pesticide formulation types and international coding system"
AUSTRALIAN JOURNAL OF AGRICULTURAL RESEARCH, vol. 58, 2007, pages 708
COLBY, S. R.: "Calculating Synergistic and Antagonistic Responses in Herbicide Combinations", WEEDS, vol. 15, 1967, pages 21 - 22
F. SCHWERDTLE ET AL., Z. PFLANZENKR. PFLANZENSCHUTZ, 1981, pages 431 - 440
J. CHEM. SOC. PERKIN TRANS., vol. 1, 1992, pages 1525 - 1529
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
KNOWLES: "Agrow Reports DS256", 2006, T&F INFORMA, article "Adjuvants and additives"
MOLLET; GRUBEMANN: "Formulation technology", 2001, WILEY VCH
PEST MANAGEMENT SCIENCE, vol. 61, 2005, pages 246
PEST MANAGEMENT SCIENCE, vol. 61, 2005, pages 258
PEST MANAGEMENT SCIENCE, vol. 61, 2005, pages 269
PEST MANAGEMENT SCIENCE, vol. 61, 2005, pages 277
PEST MANAGEMENT SCIENCE, vol. 61, 2005, pages 286
PEST MANAGEMENT SCIENCE, vol. 64, 2008, pages 326
PEST MANAGEMENT SCIENCE, vol. 64, 2008, pages 332
SCIENCE, vol. 316, 2007, pages 1185
WEED SCIENCE, vol. 57, 2009, pages 108

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11589591B2 (en) 2017-08-09 2023-02-28 Basf Se Herbicidal mixtures comprising L-glufosinate and their use in corn cultures
US11477985B2 (en) 2017-08-09 2022-10-25 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and at least one photosynthesis inhibitor
US11350631B2 (en) 2017-08-09 2022-06-07 Basf Se Herbicidal mixtures comprising l-glufosinate or its salt and at least one VLCFA inhibitor
US11122807B2 (en) 2017-08-09 2021-09-21 Basf Se Herbicidal mixtures comprising L-glufosinate or its salt and a second herbicide
US11363818B2 (en) 2017-08-09 2022-06-21 Basf Se Herbicidal mixtures comprising L-glufosinate and their use in soybean 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
EP3675635A4 (fr) * 2017-09-01 2021-05-19 Dow Agrosciences LLC Compositions herbicides contenant des acides pyridine carboxyliques ou des dérivés de ceux-ci, avec du glyphosate ou du glufosinate, ou des dérivés de ceux-ci
WO2019195496A1 (fr) * 2018-04-04 2019-10-10 Dow Agrosciences Llc Lutte améliorée contre les mauvaises herbes par applications d'herbicides à base d'acide pyridine carboxylique et d'inhibiteurs d'acétyl coenzyme a caroxylase (accase)
WO2019195495A1 (fr) * 2018-04-04 2019-10-10 Dow Agrosciences Llc Lutte contre les mauvaises herbes par applications d'herbicides à base d'acide pyridine carboxylique et d'inhibiteurs de 4-hydroxyphényl-pyruvate dioxygénase (hppd)
US10555528B1 (en) 2019-03-20 2020-02-11 Sumitomo Chemical Company, Limited Herbicidal composition and method for controlling weeds
WO2021151738A1 (fr) 2020-01-31 2021-08-05 Basf Se Combinaisons herbicides comprenant du glufosinate et de l'epyrifenacil
WO2021151743A1 (fr) 2020-01-31 2021-08-05 Basf Se Combinaisons herbicides comprenant du glufosinate et de la trifludimoxazine
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
WO2022152728A1 (fr) * 2021-01-15 2022-07-21 Bayer Aktiengesellschaft Compositions herbicides
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
CN115104622B (zh) * 2021-03-22 2024-01-02 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
WO2024052665A1 (fr) * 2022-09-07 2024-03-14 Upl Mauritius Limited Combinaison herbicide, composition et procédé de lutte contre les mauvaises herbes l'utilisant

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