AU2018314499B2 - Herbicidal mixtures comprising L-glufosinate and their use in canola cultures - Google Patents
Herbicidal mixtures comprising L-glufosinate and their use in canola cultures Download PDFInfo
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- AU2018314499B2 AU2018314499B2 AU2018314499A AU2018314499A AU2018314499B2 AU 2018314499 B2 AU2018314499 B2 AU 2018314499B2 AU 2018314499 A AU2018314499 A AU 2018314499A AU 2018314499 A AU2018314499 A AU 2018314499A AU 2018314499 B2 AU2018314499 B2 AU 2018314499B2
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- AU
- Australia
- Prior art keywords
- glufosinate
- saflufenacil
- salts
- esters
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 title claims abstract description 219
- 239000000203 mixture Substances 0.000 title claims abstract description 185
- 240000000385 Brassica napus var. napus Species 0.000 title claims abstract description 78
- 235000004977 Brassica sinapistrum Nutrition 0.000 title claims abstract description 73
- 235000006008 Brassica napus var napus Nutrition 0.000 title claims abstract description 69
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 title claims abstract description 68
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 title claims abstract description 68
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 59
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 claims abstract description 318
- 150000003839 salts Chemical class 0.000 claims abstract description 126
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 claims abstract description 120
- 239000005504 Dicamba Substances 0.000 claims abstract description 111
- 150000002148 esters Chemical class 0.000 claims abstract description 109
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims abstract description 105
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000005578 Mesotrione Substances 0.000 claims abstract description 63
- 239000005620 Tembotrione Substances 0.000 claims abstract description 60
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1r,5s)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 claims abstract description 57
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims abstract description 57
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims abstract description 55
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000005591 Pendimethalin Substances 0.000 claims abstract description 53
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000005625 Tri-allate Substances 0.000 claims abstract description 48
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 claims abstract description 47
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims abstract description 47
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 claims abstract description 42
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims abstract description 41
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims abstract description 38
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000005489 Bromoxynil Substances 0.000 claims abstract description 37
- PJPDUXCVLFAQBM-UHFFFAOYSA-N quinclorac-dimethylammonium Chemical compound CNC.ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 PJPDUXCVLFAQBM-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000005500 Clopyralid Substances 0.000 claims abstract description 32
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 30
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000005468 Aminopyralid Substances 0.000 claims abstract description 28
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims abstract description 28
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims abstract description 28
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000005595 Picloram Substances 0.000 claims abstract description 26
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims abstract description 26
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000005497 Clethodim Substances 0.000 claims abstract description 25
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 claims abstract description 25
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 claims abstract description 25
- GHLCSCRDVVEUQD-UHFFFAOYSA-N 1-({1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl}oxy)ethyl methyl carbonate Chemical compound CCN1N=CC(C(=O)C=2C(=C(OCCOC)C(=CC=2)S(C)(=O)=O)C)=C1OC(C)OC(=O)OC GHLCSCRDVVEUQD-UHFFFAOYSA-N 0.000 claims abstract description 24
- IOYNQIMAUDJVEI-ZFNPBRLTSA-N 2-[N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-3-hydroxy-5-(oxan-4-yl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOC\C=C\Cl)CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-ZFNPBRLTSA-N 0.000 claims abstract description 24
- 239000005501 Cycloxydim Substances 0.000 claims abstract description 22
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 claims abstract description 22
- 239000005615 Quizalofop-P-tefuryl Substances 0.000 claims abstract description 20
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 claims abstract description 20
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 claims abstract description 20
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 claims abstract description 19
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005529 Florasulam Substances 0.000 claims abstract description 17
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005566 Imazamox Substances 0.000 claims abstract description 17
- 239000005593 Pethoxamid Substances 0.000 claims abstract description 17
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005605 Pyraflufen-ethyl Substances 0.000 claims abstract description 16
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 claims abstract description 16
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000005509 Dimethenamid-P Substances 0.000 claims abstract description 15
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000005580 Metazachlor Substances 0.000 claims abstract description 15
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000005585 Napropamide Substances 0.000 claims abstract description 15
- 239000005602 Propyzamide Substances 0.000 claims abstract description 15
- 239000005608 Quinmerac Substances 0.000 claims abstract description 15
- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 claims abstract description 15
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 claims abstract description 15
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims abstract description 15
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 claims abstract description 15
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 claims abstract description 15
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 claims abstract description 15
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims abstract description 14
- WXZVAROIGSFCFJ-CYBMUJFWSA-N (R)-napropamide Chemical compound C1=CC=C2C(O[C@H](C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-CYBMUJFWSA-N 0.000 claims abstract description 13
- KCTKQZUYHSKJLP-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylate;propan-2-ylazanium Chemical compound CC(C)[NH3+].N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C([O-])=O KCTKQZUYHSKJLP-UHFFFAOYSA-N 0.000 claims abstract description 13
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims abstract description 13
- KPSTXQYTZBZXMM-UHFFFAOYSA-N 2-[8-chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carbonyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2C(CCCC2=O)=O)=NC2=C(Cl)C=CC=C21 KPSTXQYTZBZXMM-UHFFFAOYSA-N 0.000 claims abstract description 13
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 claims abstract description 13
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- SLYAVQCIBHSIQW-UHFFFAOYSA-N 4-amino-3,6-dichloropyridine-2-carboxylic acid;1-[bis(2-hydroxypropyl)amino]propan-2-ol Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl.CC(O)CN(CC(C)O)CC(C)O SLYAVQCIBHSIQW-UHFFFAOYSA-N 0.000 claims abstract description 13
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005490 Carbetamide Substances 0.000 claims abstract description 13
- 239000005499 Clomazone Substances 0.000 claims abstract description 13
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 claims abstract description 13
- GNZZHGJSMCDMBU-UHFFFAOYSA-N azane;5-(methoxymethyl)-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 GNZZHGJSMCDMBU-UHFFFAOYSA-N 0.000 claims abstract description 13
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims abstract description 13
- IRLGCAJYYKDTCG-UHFFFAOYSA-N ethametsulfuron Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 IRLGCAJYYKDTCG-UHFFFAOYSA-N 0.000 claims abstract description 13
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 claims abstract description 12
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 claims abstract description 12
- HYOWIYLMXADQFD-UHFFFAOYSA-N 4-amino-3,6-dichloropyridine-2-carboxylic acid;n-methylmethanamine Chemical compound CNC.NC1=CC(Cl)=NC(C(O)=O)=C1Cl HYOWIYLMXADQFD-UHFFFAOYSA-N 0.000 claims abstract description 12
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005508 Dimethachlor Substances 0.000 claims abstract description 12
- 239000005609 Quizalofop-P Substances 0.000 claims abstract description 12
- 239000005614 Quizalofop-P-ethyl Substances 0.000 claims abstract description 12
- 239000005617 S-Metolachlor Substances 0.000 claims abstract description 12
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims abstract description 12
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 claims abstract description 12
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 claims abstract description 12
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 claims abstract description 12
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 claims abstract description 12
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 claims abstract description 12
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Abstract
The present invention relates to herbicidal mixtures and their methods and uses for controlling undesirable vegetation in glufosinate-tolerant canola, wherein the herbicidal mixture comprises L-glufosinate and and 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, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, tribenuron-methyl, florasulam, cyanazine, bromoxynil and its salts and esters, bentazone, bentazone-sodium, pyridate, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, picolinafen, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalfluralin, pendimethalin, triallate, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, diflufenzopyr, diflufenzopyr-sodium, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, topramezone, sethoxydim, pethoxamid, clopyralid, picloram, fluroxypyrand other compounds.
Description
Herbicidal mixtures comprising L-glufosinate and their use in canola cultures Description 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, quizalofop-P-tefuryl, tepraloxydim, ethamet- sulfuron, ethametsulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isoprop- ylammonium, imazethapyr, imazethapyr ammonium, tribenuron-methyl, florasulam, cyanazine, bromoxynil and its salts and esters, bentazone, bentazone-sodium, pyridate, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraf I uf en-ethyl, flumioxazin, tiafenacil, picolinafen, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalfluralin, pendimethalin, triallate, trifluralin, propyzamide, car- betamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S- metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, diflufenzopyr, diflufenzopyr-sodium, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, 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, topramezone, sethoxydim, pethoxamid, clopyralid, picloram, fluroxypyr, 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), II-85: 2-[[3-[[3-chloro- 6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]- 2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1 ), II-86: 2-[[3-[[3-chloro-6-[3,6- dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2- pyridinyl]oxy]-acetic acid ethyl ester (CAS 2158274-56-5), II-87: 2-[2-[[3-chloro-6-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N- (methylsulfonyl)-acetamide (CAS 2158274-53-2), II-88: 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl- 2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid ethyl ester (CAS 2158274-50-9), II-89: ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo- 1 ,2,4-triazol-1 -yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), II-90: 2-[[3-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 11-91 : 2-[2-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3) and II-92: me-thyl 2-[[3-[2- chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1 -yl]-4-fluoro-phenoxy]-2- pyridyl]oxy]acetate.
The invention also relates to methods and uses for controlling undesirable vegetation in glufosinate-tolerant canola.
Tolerant or resistant canola varieties (e.g. transgenic 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. 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. 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. However, 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). Thus, 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.
Thus, it is an object of the present invention to find combinations of active compounds with a favorable profile of action, high stability and, ideally, synergistically enhanced activity for application in glufosinate tolerant canola, which allows the application rate to be reduced in comparison with solutions provided by prior art mixtures. Moreover, 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).
Surprisingly, it has been found that 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 canola and canola that is tolerant against herbicides including glufosinate and in post-emergence use in glufosinate tolerant canola and/or show superior compatibility with canola, i.e. their use leads to a reduced damage of the canola plants and/or does not result in increased damage of the canola plants, if compared to mixtures of racemic glufosinate and the herbicidal compound II, or if compared to L-glufosinate or its salts alone. Thus, the present invention relates to herbicidal mixtures of
1 ) L-glufosinate or its salt as compound I and
2) 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- methabenz, imazamethabenz-methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, tribenuron-methyl, florasulam, cyanazine, bromoxynil and its salts and esters, benta- zone, bentazone-sodium, pyridate, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfen- trazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, picolinafen, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalflu- ralin, pendimethalin, triallate, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, bu- tachlor, dimethachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide- M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, diflufenzopyr, diflufen- zopyr-sodium, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dime- thylammonium, 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, topramezone, sethox- ydim, pethoxamid, clopyralid, picloram, fluroxypyr, 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), II-85: 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-
1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1 ), II-86: 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid ethyl ester (CAS 2158274-56-5), II-87: 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)- acetamide (CAS 2158274-53-2), II-88: 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid ethyl ester (CAS 2158274-50-9), II-89: ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-
triazol-1 -yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4) , II-90: 2-[[3-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom
pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 11-91 : 2-[2-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3) and II-92: methyl 2-[[3- [2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1 -yl]-4-fluoro-phenoxy]-2- pyridyl]oxy]acetate.
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. Pflanzenkr. Pflanzenschutz, 1981 , Sonderheft IX, pp. 431 -440. Racemic glufosinate and its salts are commercially available, e.g. from Bayer CropScience under the tradenames Basta™ and Liberty™.
L-Glufosinate, also called glufosinate-P, is (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. 73777-50-1 ); L-glufosinate-sodium (also called glufosinate-P-sodium), which is sodium (2S)-2-amino-4-(methylphosphinato)butyric acid (CAS Reg. No. 70033-13-5) and L-glufosinate-potassium (also called glufosinate-P-potassium), which is potassium (2S)-2-amino-4-(methylphosphinato)butyric acid.
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.
In a preferred embodiment, 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
WO2017/202768. Compounds II-89 and II-92 are known from WO2018/108695. Compound II- 93 is known from WO 2014/151005.
In the inventive mixtures 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.
Furthermore, mixtures are preferred, which contain L-glufosinate-ammonium or L-glufosinate- sodium as L-glufosinate salts or L-glufosinate as free acid. Especially preferred are mixtures, which contain L-glufosinate-ammonium as L-glufosinate salt. In one embodiment, the present present invention relates to herbicidal mixtures of
1 ) L- glufosinate and its salts, and
2) 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, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazethapyr, cyanazine, bromoxynil and its salts and esters, bentazone, benta- zone-sodium, pyridate, carfentrazone, carfentrazone-ethyl, saflufenacil, trifludimoxazin, pic- olinafen, clomazone, mesotrione, Fenquinotrione, ethalfluralin, pendimethalin, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, metolachlor-S, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, diflufenzopyr, diflufenzopyr-sodium, cinmethylin, dimethena- mid, dimethenamid-P, quinclorac, topramezone, sethoxydim, pethoxamid, clopyralid and pi- cloram.
In one embodiment, 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 ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammoni- urn, cyanazine, bromoxynil and its salts and esters, pyridate, carfentrazone, carfentrazone- ethyl, saflufenacil, trifludimoxazin, clomazone, mesotrione, fenquinotrione, ethalfluralin, pendimethalin, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, topramezone, sethoxydim, pethoxamid, clopyralid, picloram.
In one embodiment, 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 ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammoni-
um, tribenuron-methyl, florasulam, cyanazine, bromoxynil and its salts and esters, pyridate, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalfluralin, pendimethalin, triallate, trifluralin, propyzamide, car- betamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S- metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, 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, topramezone, sethoxydim, pethoxamid, clopyralid, picloram, fluroxy- pyr, compounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92.
In a preferred embodiment, 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, aminopyralid and its salts, clopyralid and its salts and esters, dicamba and its salts and esters, quin- merac, cinmethylin, quinclorac, quinclorac dimethylammonium, II-93: 4-amino-3-chloro-5-fluoro- 6-(7-f!uoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (CAS 1628702-28-2) and its salts and esters, topramezone, sethoxydim, pethoxamid, picloram, fluroxypyr, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92. In a preferred embodiment, 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, picloram, fluroxypyr, pendimethalin, ethalfluralin, triallate.
In another preferred embodiment, 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
1628702-28-2) and its salts and esters, 2,4-D and its salts and esters, dicamba and its salts and esters, aminopyralid, picloram, fluroxypyr.
In another embodiment, the compounds II in the mixtures of the invention are selected from the group consisting of imazapyr, tribenuron-methyl and florasulam.
In another preferred embodiment, 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.
In another embodiment, 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.
In another preferred embodiment, 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.
In another embodiment, the compounds II in the mixtures of the invention are selected from the group consisting of pendimethalin, ethalfluralin, triallate.
Thus, 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-P-ethyl, quizalofop-P-tefuryl, tepra- loxydim, ethametsulfuron, ethametsulfuron-methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, cyanazine, bromoxynil and its salts and esters, pyridate, carfentrazone, carfentra- zone-ethyl, saflufenacil, trifludimoxazin, clomazone, mesotrione, fenquinotrione, ethalfluralin, pendimethalin, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, butachlor, di- methachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, ami- nopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, topramezone, sethoxydim, pethoxamid, clopyralid, picloram.
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-ethyl, quizalofop-P-tefuryl, tepraloxydim, ethametsulfu- ron, ethametsulfuron-methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, tribenuron- methyl, florasulam, cyanazine, bromoxynil and its salts and esters, pyridate, carfentrazone, car- fentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalfluralin, pendimethalin, triallate, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters,
clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, 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, topramezone, sethoxydim, pethoxamid, clopyralid, picloram, fluroxypyr com- pounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 and II-92.
In a preferred embodiment, 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, pyrasulfotole, bicyclopyrone, tolpyralate, ethalfluralin, pendimethalin, triallate, propyzamide, carbetamide, metazachlor, napropamide, 2,4-D and its salts and esters, amino- pyralid and its salts, clopyralid and its salts and esters, dicamba and its salts and esters, quin- merac, cinmethylin, quinclorac, quinclorac dimethylammonium, N-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, topramezone, sethoxydim, pethoxamid, picloram, fluroxypyr, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 and II-92. 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-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, fluroxypyr, pendimethalin, ethalfluralin and triallate.
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 1628702-28-2) and its salts and esters, 2,4-D and its salts and esters, dicamba and its salts and esters, aminopyralid, picloram, fluroxypyr.
In one embodiment, 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.
In another preferred embodiment, 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.
In another embodiment, 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.
In another preferred embodiment, 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. In another embodiment, 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.
All preferred mixtures are listed in table 2, wherein the following abbreviations are used in table 1 :
Table 1
Compound Abbreviation nium
imazethapyr 11-17 imazethapyr ammonium ll-17a bromoxynil and its salts 11-18 and esters
carfentrazone 11-19 carfentrazone-ethyl II-20 saflufenacil 11-21 trifludimoxazin II-22 clomazone II-23 fenquinotrione II-24 ethalfluralin II-25 pendimethalin II-26 trifluralin II-27 propyzamide II-28 acetochlor II-29 butachlor II-30 dimethachlor 11-31 metazachlor II-32 napropamide II-33 napro-pamide-M II-34 aminopyralid and its salts II-35
such as 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
esters tribenuron-methyl II-68 quin-merac II-39 florasulam II-69 cinmethylin II-40 sulfentrazone II-70 dimethenamid 11-41 pyraflufen-ethyl 11-71 dimethen-amid-P II-42 tembotrione II-72 quinclorac II-43 pyrasulfotole II-73 quinclorac dimethylammoll-43a bicyclopyrone II-74 nium triallate II-75 topramezone II-44 2,4-D and its salts and esII-76 sethoxydim II-45 ters
pethoxamid II-46 aminopyralid and its salts II-77 clopyralid II-47 fluroxypyr II-78 picloram II-48 see below II-83 fenoxaprop II-49 see below II-84 fenoxaprop-ethyl II-50 see below II-85 fenoxaprop-P 11-51 see below II-86 fenoxaprop-P-ethyl II-52 see below II-87 fluazifop II-53 see below II-88 fluazifop-butyl II-54 see below II-89 fluazifop-P II-55 see below II-90 fluazifop-P-butyl II-56 see below 11-91 propaquizafop II-57 see below II-92 ethametsulfuron II-58 see below II-93 ethametsulfuron-methyl II-59 tiafenacil II-94 cyanazine II-60 tolpyralate II-95 pyridate 11-61
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)
II-85: 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1 ) II-86: 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid ethyl ester (CAS 2158274-56-5)
II-87: 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl^ fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2) II-88: 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid ethyl ester (CAS 2158274-50-9)
II-89: ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1 -yl]-4-fluoro- phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4)
II-90: 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pynmidinyl]-5 fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9) 11-91 : 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3)
II-92: methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1 -yl]-4-fluoro- phenoxy]-2-pyridyl]oxy]acetate
II-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (CAS
1628702-28-2)
Table 2
No I II No I II
M-1 1-1 11-1 M-27 1-1 M-27
M-2 1-1 M-2 M-28 1-1 M-28
M-3 1-1 M-3 M-29 1-1 M-29
M-4 1-1 M-4 M-30 1-1 M-30
M-5 1-1 M-5 M-31 1-1 11-31
M-6 1-1 M-6 M-32 1-1 M-32
M-7 1-1 M-7 M-33 1-1 M-33
M-8 1-1 M-8 M-34 1-1 M-34
M-9 1-1 M-9 M-35 1-1 M-35
M-10 1-1 11-10 M-36 1-1 M-36
M-1 1 1-1 11-1 1 M-37 1-1 M-37
M-12 1-1 11-12 M-38 1-1 M-38
M-13 1-1 11-13 M-39 1-1 M-39
M-14 1-1 11-14 M-40 1-1 M-40
M-15 1-1 11-15 M-41 1-1 11-41
M-16 1-1 11-16 M-42 1-1 M-42
M-17 1-1 11-17 M-43 1-1 M-43
M-18 1-1 11-18 M-44 1-1 M-44
M-19 1-1 11-19 M-45 1-1 M-45
M-20 1-1 M-20 M-46 1-1 M-46
M-21 1-1 11-21 M-47 1-1 M-47
M-22 1-1 M-22 M-48 1-1 M-48
M-23 1-1 M-23 M-49 1-1 M-49
M-24 1-1 M-24 M-50 1-1 M-50
M-25 1-1 M-25 M-51 1-1 11-51
M-26 1-1 M-26 M-52 1-1 M-52
No I I I No I I I
M-53 1-1 M-53 M-94 I-2 M-27
M-54 1-1 M-54 M-95 I-2 M-28
M-55 1-1 M-55 M-96 I-2 M-29
M-56 1-1 M-56 M-97 I-2 M-30
M-57 1-1 M-57 M-98 I-2 11-31
M-58 1-1 M-58 M-99 I-2 M-32
M-59 1-1 M-59 M-100 I-2 M-33
M-60 1-1 M-60 M-101 I-2 M-34
M-61 1-1 11-61 M-102 I-2 M-35
M-62 1-1 M-62 M-103 I-2 M-36
M-63 1-1 M-63 M-104 I-2 M-37
M-64 1-1 M-64 M-105 I-2 M-38
M-65 1-1 M-65 M-106 I-2 M-39
M-66 1-1 M-66 M-107 I-2 M-40
M-67 1-1 M-67 M-108 I-2 11-41
M-68 I-2 11-1 M-109 I-2 M-42
M-69 I-2 M-2 M-1 10 I-2 M-43
M-70 I-2 M-3 M-1 1 1 I-2 M-44
M-71 I-2 M-4 M-1 12 I-2 M-45
M-72 I-2 M-5 M-1 13 I-2 M-46
M-73 I-2 M-6 M-1 14 I-2 M-47
M-74 I-2 M-7 M-1 15 I-2 M-48
M-75 I-2 M-8 M-1 16 I-2 M-49
M-76 I-2 M-9 M-1 17 I-2 M-50
M-77 I-2 11-10 M-1 18 I-2 11-51
M-78 I-2 11-1 1 M-1 19 I-2 M-52
M-79 I-2 11-12 M-120 I-2 M-53
M-80 I-2 11-13 M-121 I-2 M-54
M-81 I-2 11-14 M-122 I-2 M-55
M-82 I-2 11-15 M-123 I-2 M-56
M-83 I-2 11-16 M-124 I-2 M-57
M-84 I-2 11-17 M-125 I-2 M-58
M-85 I-2 11-18 M-126 I-2 M-59
M-86 I-2 11-19 M-127 I-2 M-60
M-87 I-2 M-20 M-128 I-2 11-61
M-88 I-2 11-21 M-129 I-2 M-62
M-89 I-2 M-22 M-130 I-2 M-63
M-90 I-2 M-23 M-131 I-2 M-64
M-91 I-2 M-24 M-132 I-2 M-65
M-92 I-2 M-25 M-133 I-2 M-66
M-93 I-2 M-26 M-134 I-2 M-67
No I II No I II
M-135 I-3 11-1 M-176 I-3 II-42
M-136 I-3 II-2 M-177 I-3 II-43
M-137 I-3 II-3 M-178 I-3 II-44
M-138 I-3 II-4 M-179 I-3 II-45
M-139 I-3 II-5 M-180 I-3 II-46
M-140 I-3 II-6 M-181 I-3 II-47
M-141 I-3 II-7 M-182 I-3 II-48
M-142 I-3 II-8 M-183 I-3 II-49
M-143 I-3 II-9 M-184 I-3 II-50
M-144 I-3 11-10 M-185 I-3 11-51
M-145 I-3 11-1 1 M-186 I-3 II-52
M-146 I-3 11-12 M-187 I-3 II-53
M-147 I-3 11-13 M-188 I-3 II-54
M-148 I-3 11-14 M-189 I-3 II-55
M-149 I-3 11-15 M-190 I-3 II-56
M-150 I-3 11-16 M-191 I-3 II-57
M-151 I-3 11-17 M-192 I-3 II-58
M-152 I-3 11-18 M-193 I-3 II-59
M-153 I-3 11-19 M-194 I-3 II-60
M-154 I-3 II-20 M-195 I-3 11-61
M-155 I-3 11-21 M-196 I-3 II-62
M-156 I-3 II-22 M-197 I-3 II-63
M-157 I-3 II-23 M-198 I-3 II-64
M-158 I-3 II-24 M-199 I-3 II-65
M-159 I-3 II-25 M-200 I-3 II-66
M-160 I-3 II-26 M-201 I-3 II-67
M-161 I-3 II-27 M-202 1-1 ll-14a
M-162 I-3 II-28 M-203 1-1 ll-15a
M-163 I-3 II-29 M-204 1-1 ll-16a
M-164 I-3 II-30 M-205 1-1 ll-17a
M-165 I-3 11-31 M-206 1-1 ll-43a
M-166 I-3 II-32 M-207 1-1 II-68
M-167 I-3 II-33 M-208 1-1 II-69
M-168 I-3 II-34 M-209 1-1 II-70
M-169 I-3 II-35 M-210 1-1 11-71
M-170 I-3 II-36 M-21 1 1-1 II-72
M-171 I-3 11-37 M-212 1-1 II-73
M-172 I-3 11-38 M-213 1-1 II-74
M-173 I-3 11-39 M-214 1-1 II-75
M-174 I-3 11-40 M-215 1-1 II-76
M-175 I-3 11-41 M-216 1-1 II-77
No I II No I II
M-217 1-1 II-78 M-254 I-3 ll-14a
M-218 1-1 II-83 M-255 I-3 ll-15a
M-219 1-1 II-84 M-256 I-3 ll-16a
M-220 1-1 II-85 M-257 I-3 ll-17a
M-221 1-1 II-86 M-258 I-3 ll-43a
M-222 1-1 11-87 M-259 I-3 II-68
M-223 1-1 11-88 M-260 I-3 II-69
M-224 1-1 11-89 M-261 I-3 II-70
M-225 1-1 11-90 M-262 I-3 11-71
M-226 1-1 11-91 M-263 I-3 II-72
M-227 1-1 II-92 M-264 I-3 II-73
M-228 I-2 ll-14a M-265 I-3 II-74
M-229 I-2 ll-15a M-266 I-3 II-75
M-230 I-2 ll-16a M-267 I-3 II-76
M-231 I-2 ll-17a M-268 I-3 II-77
M-232 I-2 ll-43a M-269 I-3 II-78
M-233 I-2 II-68 M-270 I-3 II-83
M-234 I-2 II-69 M-271 I-3 II-84
M-235 I-2 II-70 M-272 I-3 II-85
M-236 I-2 11-71 M-273 I-3 II-86
M-237 I-2 II-72 M-274 I-3 II-87
M-238 I-2 II-73 M-275 I-3 II-88
M-239 I-2 II-74 M-276 I-3 II-89
M-240 I-2 II-75 M-277 I-3 II-90
M-241 I-2 II-76 M-278 I-3 11-91
M-242 I-2 II-77 M-279 I-3 II-92
M-243 I-2 II-78 M-280 1-1 II-93
M-244 I-2 II-83 M-281 I-2 II-93
M-245 I-2 II-84 M-282 I-3 II-93
M-246 I-2 II-85 M-283 1-1 II-94
M-247 I-2 II-86 M-284 I-2 II-94
M-248 I-2 II-87 M-285 I-3 II-94
M-249 I-2 II-88 M-286 1-1 II-95
M-250 I-2 II-89 M-287 I-2 II-95
M-251 I-2 II-90 M-288 I-3 II-95
M-252 I-2 11-91
M-253 I-2 II-92
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, tribenuron-methyl, florasulam, bromoxynil and its salts and esters, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraf I uf en-ethyl, flumioxazin, tiafenacil, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalfluralin, pendimethalin, triallate, trifluralin, propyzamide, aceto- chlor, butachlor, dimethachlor, metazachlor, napropamide, napropamide-M, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quin- clorac dimethylammonium, topramezone, sethoxydim, pethoxamid, clopyralid, picloram, fluroxy- pyr, compounds II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92 and II-93. Thus, preferred are mixtures M-1 , M-2, M-3, M-4, M-5, M-6, M-7, M-8, M-9, M-10, M-1 1 , M-12, M-13, M-14, M-15, M-16, M-17, M-18, M-19, M-20, M-21 , M-22, M-23, M-24, M-25, M-26, M-27, M-28, M-29, M-30, M-31 , M-32, M-33, M-34, M-35, M-36, M-37, M-38, M-39, M-40, M-41 , M-42, M-43, M-44, M-45, M-46, M-47, M-48, M-49, M-50, M-51 , M-52, M-53, M-54, M-55, M-56, M-57, M-58, M-59, M-60, M-61 , M-62, M-63, M-64, M-65, M-66, M-67, M-68, M-69, M-70, M-71 , M-72, M-73, M-74, M-75, M-76, M-77, M-78, M-79, M-80, M-81 , M-82, M-83, M-84, M-85, M-86, M-87, M-88, M-89, M-90, M-91 , M-92, M-93, M-94, M-95, M-96, M-97, M-98, M-99, M-100, M-101 , M- 102, M-103, M-104, M-105, M-106, M-107, M-108, M-109, M-1 10, M-1 1 1 , M-1 12, M-1 13, M- 1 14, M-1 15, M-1 16, M-1 17, M-1 18, M-1 19, M-120, M-121 , M-122, M-123, M-124, M-125, M- 126, M-127, M-128, M-129, M-130, M-131 , M-132, M-133, M-134, M-135, M-136, M-137, M- 138, M-139, M-140, M-141 , M-142, M-143, M-144, M-145, M-146, M-147, M-148, M-149, M- 150, M-151 , M-152, M-153, M-154, M-155, M-156, M-157, M-158, M-159, M-160, M-161 , M- 162, M-163, M-164, M-165, M-166, M-167, M-168, M-169, M-170, M-171 , M-172, M-173, M- 174, M-175, M-176, M-177, M-178, M-179, M-180, M-181 , M-182, M-183, M-184, M-185, M- 186, M-187, M-188, M-189, M-190, M-191 , M-192, M-193, M-194, M-195, M-196, M-197, M- 198, M-199, M-200, M-201 , M-202, M-203, M-204, M-205, M-206, M-207, M-208, M-209, M- 210, M-21 1 , M-212, M-213, M-214, M-215, M-216, M-217, M-218, M-219, M-220, M-221 , M- 222, M-223, M-224, M-225, M-226, M-227, M-228, M-229, M-230, M-231 , M-232, M-233, M- 234, M-235, M-236, M-237, M-238, M-239, M-240, M-241 , M-242, M-243, M-244, M-245, M- 246, M-247, M-248, M-249, M-250, M-251 , M-252, M-253, M-254, M-255, M-256, M-257, M- 258, M-259, M-260, M-261 , M-262, M-263, M-264, M-265, M-266, M-267, M-268, M-269, M-
270, M-271 , M-272, M-273, M-274, M-275, M-276, M-277, M-278,M-279, M-280, M-281 , M-282, M-283, M-284, M-285, M-286, M-287 and M-288..
More preferred are mixtures M-16, M-18, M-19, M-20, M-22, M-25, M-26, M-38, M-44, M-48, M- 62, M-67, M-83, M-85, M-86, M-87, M-89, M-92, M-93, M-105, M-1 1 1 , M-1 15, M-129, M-134, M- 150, M-152, M-153, M-154, M-156, M-159, M-160, M-172, M-178, M-182, M-196, M-201 , M- 204, M-207, M-208, M-209, M-210, M-21 1 , M-212, M-213, M-214, M-215, M-216, M-217, M- 218, M-219, M-220, M-221 , M-222, M-223, M-224, M-225, M-226, M-227, M-230, M-233, M-
234, M-235, M-236, M-237, M-238, M-239, M-240, M-241 , M-242, M-243, M-244, M-245, M- 246, M-247, M-248, M-249, M-250, M-251 , M-252, M-253, M-256, M-259, M-260, M-261 , M- 262, M-263, M-264, M-265, M-266, M-267, M-268, M-269, M-270, M-271 , M-272, M-273, M- 274, M-275, M-276, M-277, M-278,M-279, M-280, M-281 , M-282, M-283, M-284, M-285, M-286, M-287 and M-288.
Also preferred are mixtures M-1 , M-2, M-3, M-4, M-5, M-6, M-7, M-8, M-9, M-10, M-1 1 , M-12, M- 13, M-14, M-15, M-16, M-17, M-18, M-19, M-20, M-21 , M-22, M-23, M-24, M-25, M-26, M-27, M- 28, M-29, M-30, M-31 , M-32, M-33, M-34, M-35, M-36, M-37, M-38, M-39, M-40, M-41 , M-42, M- 43, M-44, M-45, M-46, M-47 and M-48.
Most preferred are mixtures M-19, M-20, M-22, M-38, M-44, M-48, M-62, M-67, M-86, M-87, M- 89, M-105, M-1 1 1 , M-1 15, M-129, M-134, M-153, M-154, M-156, M-172, M-178, M-182, M-196, M-201 , M-209, M-210, M-21 1 , M-212, M-213, M-215, M-216, M-217, M-218, M-219, M-220, M- 221 , M-222, M-223, M-224, M-225, M-226, M-227, M-235, M-236, M-237, M-238, M-239, M- 241 , M-242, M-243, M-244, M-245, M-246, M-247, M-248, M-249, M-250, M-251 , M-252, M- 253, M-261 , M-262, M-263, M-264, M-265, M-267, M-268, M-269, M-270, M-271 , M-272, M- 273, M-274, M-275, M-276, M-277, M-278,M-279, M-280, M-281 , M-282, M-283, M-284, M-285, M-286, M-287 and M-288.
All above-referred mixtures are herein below referred to as "inventive mixtures".
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. Examples for 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), gran- ules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further mixtures types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
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. 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.
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. Examples of 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. Examples of 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. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides. Examples of 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 (e.g. in red, blue, or green) 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.
Examples for mixture types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of an inventive mixture and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of an inventive mixture and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a disper- sion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of an inventive mixture and 5-10 wt% emulsifiers (e.g. calcium dodecylben- zenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of an inventive mixture and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzene- sulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 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. For FS type mixture up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
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.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
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.
viii) Gel (GW, GF)
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.
ix) Microemulsion (ME)
5-20 wt% of an inventive mixture 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.
x) Microcapsules (CS)
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. Alternatively, 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). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of pol- yurea microcapsules. The monomers amount to 1-10 wt%. The wt% relate to the total CS mixture.
xi) Dustable powders (DP, DS)
1 -10 wt% of an inventive mixture are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
x) Granules (GR, FG)
0.5-30 wt% of an inventive mixture is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xii) Ultra-low volume liquids (UL)
1 -50 wt% of an inventive mixture are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
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. Preferably, 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.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) 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). 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. Usually, 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. Usually, 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. Thus, in the methods and uses of the invention, 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).
Thus, 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.
The term "locus", as used herein, means the area in which the vegetation or plants are growing or will grow, typically a field.
As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation", "undesirable species", "undesirable plants",
"harmful plants", "undesirable weeds", or "harmfull weeds" are synonyms.
When using the inventive mixtures in the methods of the present invention, the active com- pounds present in the inventive mixtures can be applied simultaneously or in succession, where undesirable vegetation may occur. Herein, it is immaterial whether 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.
In the above-mentioned methods of controlling weeds by application of the inventive mixtures, 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. In this context, 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.
Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compositions according to the invention, without the enumeration being a restriction to certain species. Both L-glufosinate alone as well as, in the methods of the present invention, 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. crus-galli), Echinchloa walteri (Pursh) Heller, jungle rice (Echinochloa colona), Echinochloa crus-pavonis, Echinochloa oryzicola, Digitaria species such as crabgrass (Digitaria sanguinalis), Digitaria hor- izontalis, sourgrass (Digitaria insularis) or naked crabgrass (Digitaria nuda), Setaria species such as green foxtail (Setaria viridis), giant foxtail (Setaria faberii), yellow foxtail (Setaria glauca or Setaria pumila) or Setaria verticillata, Sorghum species such as johnsongrass (Sorghum halepense Pers.), Avena species such as wild oats (Avena fatua), Avena sterillis or Avena stri- gosa, Cenchrus species such as Cenchrus species such as field sandbur (Cenchrus pauciflo- rus) or Cenchrus echinatus, Bromus species such as Bromus japonicus Thunb, Bromus sterilis or Bromus tectorum, Lolium species, Phalaris species such as Phalaris brachystachys, Phalaris minor or Phalaris persicaria, Eriochloa species, Panicum species such as fall panicum (Panicum
dichotomiflorum), Panicum fasciculatum or Panicum maximum, Brachiaria species, annual bluegrass (Poa annua), Alopecurus species such as blackgrass (Alopecurus myosuroides), Al- opecurus aequalis Sobol or Alopecurus japonicus Steud, Aegilops species such as Aegilops cylindrica or Aegylops tauschii, Apera spica-venti, Eleusine indica, Cynodon dactylon, couch grass (Agropyron repens or Elymus repens), Agrostis alba, Beckmannia syzigachne (Steud.) Fernald, Chloris species such as Chloris virgata, Commelina species such as Commelina ben- ghalensis, Commelina communis, Commelina diffusa or Commelina erecta, Dactyloctenium aegyptium, Hordeum jubatum, Hordeum leporinum, Imperata cylindrica, Ischaemum rogusum, Ixophorus unisetus, Leerisa hexandra, Leersia japonica, Leptochloa species such as Lepto- chloa chinensis, Leptochloa fascicularis, Leptochloa filiformis or Leptochloa panicoides, Lolium species such as Lolium multiflorum, Lolium perenne, Lolium persicum or rigid ryegrass (Lolium rigidum), Luziola subintegra, Murdannia nudiflora (L.) Brenan, Oryza latifolia, Oryza rufipogon, Paspalum distichum, Paspalum species, Pennisetum americanum, Pennisetum purpureum, Phleum paniculatum, Phragmites australia, Ploypogon fugax. N., 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 serotinum or Quinoa (Chenopodium quinoa), Sida species such as prickly sida (Sida spinosa L.), Ambrosia species such as com- mon ragweed (Ambrosia artemisiifolia) or giant ragweed (Ambrosia trifida), Acanthospermum species, Anthemis species such as Anthemis arvensis or Anthemis cotula, Atriplex species, Cirsium species such as Cirsium arvense, Convolvulus species such as field bindweed (Convolvulus arvensis), Conyza species such as horseweed (Conyza canadensis, Erigeron canadensis) or hairy fleabane (Conyza bonariensis, Erigeron bonariensis), Cassia species, Datura species such as jimsonweed (Datura stramonium), Euphorbia species such as toothed spurge (Euphorbia dentata), Euphorbia hirta, Euphorbia helioscopia or fireplant (Euphorbia heterophyl- la), Geranium species such as Geranium donianum or Geranium pusillum, Galinsoga species, morningglory (Ipomoea species), Lamium species such as henbit dead-nettle (Lamium amplexi- caule), Malva species such as dwarf mallow (Malva neglecta) or cheeseweed (Malwa parviflo- ra), Matricaria species such as chamomile (Matricaria chamomilla) or Matricaria inodora,
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 (Raphanus raphanistrum), Salsola species such as Salsola tragus or Salsola kali, Sinapis arvensis, Sonchus species sucha Sonchus asper, Sonchus arvensis or Sonchus oleraceus, Thlaspi arvense, Tagetes minuta, Richardia species such as Richardia scabra or Richardia brasiliensis, Aeschynomeme species such as Aeschynomene denticulata, Aeschynomene indica orAeschynomene rudis, Alisma species such as Alisma canaliculatum orAlisma plantago-aquatica, Borreria species such as Borreria verticil- lata, Brassica rapa, Carduus acanthoides, Parietaria debilis, Portulaca oleracea, Ipomoea species such as Ipomoea grandifolia, Ipomoea hederacea, Ipomoea indivisa, Ipomoea lacunose, Ipomoea lonchophylla or Ipomoea wrightii,, Senna obtusifolia, Sida species such as arrowleaf sida (Sida rhombifolia) or prickly sida (Sida spinosa), Spermacoce latifolia, Tridax procumbens, Trianthema portulacastrum, Parthenium hysterophorus, Portulaca oleracea, Acalypha australis, Ammi majus, Atriplex species, Orobanche species, Mercurialis annua, Cirsium arvense, Calys- tegia sepium, Stellaria media, Lamium species, Viola species, Celosia argentea, Melampodium divaricatum, Cleome viscosa, Molugo verticilatus, Borhevia erecta, Gomphrena species, Nican- dra physalodes, Ricinus communis, Geranium dissectum, Alternanthera species such as Al- thernanthera philoxeroides or Alternanthera tenella, Ammannia species such as Ammania coc- cinea, Anacamtodon fortunei Mitt., Anagallis arvensis, Aneilema keisak, Arenaria serpyllifolia, Argemone mexicana, Asphodelus tenuifolius, Atriplex patula, Bacopa rotundifolia, Brassica na- pus, Caperonia species sucha as Caperonia castaneifolia or Caperonia palustris, Cephalano- plos segetum, Corynopus didymus, Crepis capillaris, Crepis tectorum, Croton lobatus, Descu- minia sophia (L), Descurainia pinnata, Echinodorus grandiflorus, Eclipta alba, Eclipta prostrata, Eichhornia crassipes, Eleocharis species, Equisetum arvense, Fallopia convolvulus, Fallopia convolvulus, Heteranthera limosa, Jussiaea species, Kallstroemia maxima, Lactuca serriola, Lathyrus aphaca, Launea mudicaulis, Leucas chinensis, Limnocharis flava, Lindernia dubia, Lindernia pyxidaria, Litospermum arvense, Ludwigia species such as Ludwigia octovallis, Mac- roptilium lathyroides, Malachium aquaticum (L), Melilotus species, Merremia aegyptia, Momor- dica charantia, Monochoria hastate, Monochoria vaginalis, Mucuna species, Murdannia nudiflo- ra, Oxalis neaei, Phylanthus species, Physalis species, Pistia stratiotes, Potamogeton distinc- tus, Rorippa islandica, Rotala indica, Rotala ramosior, Rumex dentatus, Rumex obtusifolius, Sagittaria montevidensis, Sagittaria pygmaea Miq., Sagittaria sagittifolia, Sagittaria trifolia L, Senecio vulgaris, Sicyos polyacanthus, Silene gallica, chenopoSisymbrium species such as Sisymbrium oficinale, Solanum species, Spergula arvensis, Sphenoclea zeylanica, Trianthema spp., Tripleurospermum inodorum, Veronica species such as Veronica persica orVeronica polita Vicia sativa and the like. 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 miliacea, Scirpus grossus, Scirpus juncoides, Scirpus juncoides Roxb, Scirpus or Bolboschoenus maritimus, Scirpus or Schoenoplectus mucronatus, Scirpus planiculmis Fr. Schmidt and the like.
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
(http://www.weedscience.org/Summary/SpeciesbySOATable.aspx). In particular, they are suitable for controlling the resistant weeds that are listed in the International Survey of Resistant Weeds, for example ACCase resistant Echinochloa crus-galli, Avena fatua, Alopecurus myosu- roides, Echinochloa colona, Alopecurus japonicus, Bromus tectorum, Hordeum murinum, Is- chaemum rugosum, Setaria viridis, Sorghum halepense, Alopecurus aequalis, Apera spica- venti, Avena sterilis, Beckmannia szygachne, Bromus diandrus, Digitaria sanguinalis, Echi- nocloa oryzoides, Echinochloa phyllopogon, Phalaris minor, Phalaris paradoxa, Setaria faberi, Setaria viridis, Brachypodium distachyon, Bromus diandrus, Bromus sterilis, Cynosurus echina- tus, Digitaria insularis, Digitaria ischaemum, Leptochloa chinensis, Phalaris brachystachis, Rot- boellia cochinchinensis, Digitaria ciliaris, Ehrharta longiflora, Eriochloa punctata, Leptochloa panicoides, Lolium persicum, Polypogon fugax, Sclerochloa kengiana, Snowdenia polystacha, Sorghum Sudanese and Brachiaria plantaginea, ALS inhibitor resistant Echinochloa crus-galli, Poa annua, Avena fatua, Alopecurus myosuroides, Echinochloa colona, Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis, Amaranthus retroflexus, Ambro- sia artemisifolia, Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Senecio ver- nalis, Alopecurus japonicus, Bidens pilosa, Bromus tectorum, Chenopodium album, Conyza bonariensis, Hordeum murinum, Ischaemum rugosum, Senecio vulgaris, Setaria viridis, Sisymbrium orientale, Sorghum halepense, Alopecurus aequalis, Amaranthus blitum, Amaranthus powellii, Apera spica-venti, Avena sterilis, Brassica rapa, Bromus diandrus, Descurainia sophia, Digitaria sanguinalis, Echinochloa oryzoides, Echinochloa phyllopogon, Euphorbia heterophylla, Lactuca serriola, Phalaris minor, Phalaris paradoxa, Setaria faberi, Setaria viridis, Sinapis arvensis, Solanum ptycanthum, Sonchus oleraceus, Stellaria media, Amaranthus blitoides, Amaranthus spinosus, Amaranthus viridis, Ambrosia trifida, Bidens subalternans, Bromus diandrus, Bromus sterilis, Capsella bursa-pastoris, Centaurea cyanus, Cynosurus echinatus, Cyperus difformis, Fimbristilis miliacea, Galeopsis tetrahit, Galium aparine, Galium spurium, Helianthus annuus, Hirschfeldia incana, Limnocharis flava, Limnophila erecta, Papaver rhoeas, Parthenium hysterophorus, Phalaris brachystachis, Polygonum convolvulus, Polygonum lapathifolium, Polygonum persicaria, Ranunculus acris, Rottboellia cochinchinensis, Sagittaria montevidensis,
Salsola tragus, Schoenoplectus mucronatus, Setaria pumila, Sonchus asper, Xanthium stru- marium, Ageratum conyzoides, Alisma canaliculatum, Alisma plantago-aquatica, Ammannia auriculata, Ammannia coccinea, Ammannia arvensis, Anthemis cotula, Bacopa rotundifolia, Bi- fora radians, Blyxa aubertii, Brassica tournefortii, Bromus japonicus, Bromus secalinus, Litho- spermum arvense, Camelina microcarpa, Chamaesyce maculata, Chrysanthemum coronarium, Clidemia hirta, Crepis tectorum, Cuscuta pentagona, Cyperus brevifolis, Cyperus compressus, Cyperus esculentus, Cyperus iria, Cyperus odoratus, Damasonium minus, Diplotaxis erucoides, Diplotaxis tenuifolia, Dopatrum junceum, Echium plantagineum, Elatine triandra, Eleocharis acicularis, Erucaria hispanica, Erysimum repandum, Galium tricornutum, Iva xanthifolia, Ixopho- rus unisetus, Lamium amplexicaule, Limnophilia sessiliflora, Lindernia dubia, Lindernia micran- tha, Lindernia procumbens, Ludwigia prostrata, Matricaria recutita, Mesembryanthemum crystal- linum, Monochoria korsakowii, Monochoria vaginalis, Myosoton aquaticum, Neslia paniculata, Oryza sativa var. sylvatica, Pentzia suffruticosa, Picris hieracioides, Raphanus sativus,
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, Spergula arvensis, Thlaspi arvense, Tripleurospermum perforatum, Vaccaria hispanica and Vicia sativa, photosynthesis inhibitor resistant Echinochloa crus-galli, Poa annua, Alopecurus myosuroides, Echinochloa colona, Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis, Amaranthus retroflexus, Ambrosia artemisifo- lia, Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Senecio vernalis, Alopecurus japonicus, Bidens pilosa, Bromus tectorum, Chenopodium album, Conyza bonariensis, Ischaemum rugosum, Senecio vulgaris, Setaria viridis, Sisymbrium orientale, Amaranthus blitum, Amaranthus powellii, Apera spica-venti, Beckmannia syzigachne, Brassica rapa, Digitaria san- guinalis, Euphorbia heterophylla, Phalaris minor, Phalaris paradoxa, Setaria faberi, Setaria viridis, Sinapis arvensis, Solanum ptycanthum, Stellaria media, Amaranthus blitoides, Amaranthus viridis, Bidens subalternans, Brachypodium distachyon, Capsella bursa-pastoris, Chloris bar- bata, Cyperus difformis, Echinochloa erecta, Epilobium ciliatum, Polygonum aviculare, Polygonum convolvulus, Polygonum lapathifolium, Polygonum persicaria, Portulaca oleracea, Schoe- noplectus mucronatus, Setaria pumila, Solanum nigrum, Sonchus asper, Urochloa panicoides, Vulpia bromoides, Abutilon theophrasti, Amaranthus albus, Amaranthus cruentus, Arabidopsis thaliana, Arenaria serpyllifolia, Bidens tripartita, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Crypsis schoenoides, Datura stramonium, Epilobium tetragonum, Galinsoga ciliata, Matricaria discoidea, Panicum capillare, Panicum dichotomiflorum, Plantago lagopus, Polygonum hydopiper, Polygonum pensylvanicum, Polygonum monspeliensis, Ros- traria, smyrnacea, Rumex acetosella, Setaria verticillata and Urtica urens, PS-l-electron diversion inhibitor resistant Poa annua, Conyza sumatrensis, Conyza canadensis, Alopecurus japonicus, Bidens pilosa, Conyza bonariensis, Hordeum murinum, Ischaemum rugosum, Amaranthus blitum, Solanum ptycanthum, Arctotheca calendula, Epilobium ciliatum, Hedyotis verticillata, Solanum nigrum, Vulpia bromoides, Convolvulus arvensis, Crassocephalum crepidioides,
Cuphea carthagensis, Erigeron philadelphicus, Gamochaeta pensylvanica, Landoltia punctata, Lepidium virginicum, Mazus fauriei, Mazus pumilus, Mitracarpus hirtus, Sclerochloa dura, Solanum americanum and Youngia japonica, glyphosate resistant Poa annua, Echinochloa colona,
Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis, Ambrosia artemisifolia, Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Bidens pilosa, Conyza bonariensis, Hordeum murinum, Sorghum halepense, Brassica rapa, Bromus diandrus, Lactuca serriola, Sonchus oleraceus, Amaranthus spinosus, Ambrosia trifida, Digitaria insularis, Hedyotis verticillata, Helianthus annuus, Parthenium hysterophorus, Plantago lanceolata, Salso- la tragus, Urochloa panicoides, Brachiaria eruciformis, Bromus rubens, Chloris elata, Chloris truncata, Chloris virgata, Cynodon hirsutus, Lactuca saligna, Leptochloa virgata, Paspalum pa- niculatum and Tridax procumbens, microtubule assembly inhibitor resistant Echinochloa crus- galli, Poa annua, Avena fatua, Alopecurus myosuroides, Amaranthus palmeri, Setaria viridis, Sorghum halepense, Alopecurus aequalis, Beckmannia syzigachne and Fumaria densifloria, auxin herbicide resistant Echinochloa crus-galli, Echinochloa colona, Amaranthus hybridus, Amaranthus rudis, Conyza sumatrensis, Kochia scoparia, Raphanus raphanistrum, Cheno- podim album, Sisymbrium orientale, Descurainia sophia, Lactuca serriola, Sinapis arvensis, Sonchus oleraceus, Stellaria media, Arctotheca calendula, Centaurea cyanus, Digitaria ischae- mum, Fimbristylis miliacea, Galeopsis tetrahit, Galium aparine, Galium spurium, Hirschfeldia incana, Limnocharis flava, Limnocharis erecta, Papaver rhoeas, Plantago lanceolata, Ranunculus acris, Carduus nutans, Carduus pycnocephalus, Centaurea soltitialis, Centaurea stoebe ssp. 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.
If 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.
If 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 canola plants, is eliminated at a very early point in time and in a sustained manner.
When the active compounds of the inventive mixtures are used jointly, superadditive
(=synergistic) effects are observed. This means that the effect in the combinations exceeds the expected total of the effects of the individual herbicides employed. The synergistic effects allow the application rate to be reduced, a broader spectrum of broad-leaved weeds and weed grasses to be controlled, the herbicidal effect to take place more rapidly, the duration of action to be longer, the harmful plants to be controlled better while using only one, or few, applications, and the application period which is possible to be extended. In some cases, uptake of the compositions also reduces the amount of harmful constituents in the crop plant, such as nitrogen or oleic acid.
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. In particular, 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. These 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).
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, picloram potassium salt, fluroxypyr 1 -methylheptyl ester, quinclorac, quin- clorac dimethylammonium, II-93: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2- pyridinecarboxylic acid (II-93), 2,4-D, 2,4-D choline salt, dicamba, dicamba sodium, dicamba ethanolamine salt, dicamba diglycolamine salt, dicamba potassium and dicamba BAPMA salt. The following 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.
Particularly suitable treatment combinations of active compounds of the inventive mixtures and further herbicides are:
The treatment combinations 1 .1 to 1.478 in which one of the treatment combinations listed in the following table is combined with post-emergence use of L-glufosinate.
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
1 L-Glufosinate Pendimethalin -
2 L-Glufosinate Trifluralin -
3 L-Glufosinate Ethalfluralin -
4 L-Glufosinate Triallate -
5 L-Glufosinate Trifludimoxazin -
6 L-Glufosinate Saflufenacil -
7 L-Glufosinate Sulfentrazone -
8 L-Glufosinate Isoxaflutole -
9 L-Glufosinate Bicyclopyrone -
10 L-Glufosinate Tembotrione -
1 1 L-Glufosinate Mesotrione -
12 L-Glufosinate Pyrasulfotole -
13 L-Glufosinate Topramezone -
14 L-Glufosinate Topramezone + bro- - moxynil
15 L-Glufosinate ammonium Pendimethalin -
16 L-Glufosinate ammonium Trifluralin -
17 L-Glufosinate ammonium Ethalfluralin -
18 L-Glufosinate ammonium Triallate -
19 L-Glufosinate ammonium Trifludimoxazin -
20 L-Glufosinate ammonium Saflufenacil -
21 L-Glufosinate ammonium Sulfentrazone -
22 L-Glufosinate ammonium Isoxaflutole -
23 L-Glufosinate ammonium Bicyclopyrone -
24 L-Glufosinate ammonium Tembotrione -
25 L-Glufosinate ammonium Mesotrione -
26 L-Glufosinate ammonium Pyrasulfotole -
27 L-Glufosinate ammonium Topramezone -
28 L-Glufosinate ammonium Topramezone + bro- - moxynil
29 L-Glufosinate sodium Pendimethalin -
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
30 L-Glufosinate sodium Trifluralin -
31 L-Glufosinate sodium Ethalfluralin -
32 L-Glufosinate sodium Triallate -
33 L-Glufosinate sodium Trifludimoxazin -
34 L-Glufosinate sodium Saflufenacil -
35 L-Glufosinate sodium Sulfentrazone -
36 L-Glufosinate sodium Isoxaflutole -
37 L-Glufosinate sodium Bicyclopyrone -
38 L-Glufosinate sodium Tembotrione -
39 L-Glufosinate sodium Mesotrione -
40 L-Glufosinate sodium Pyrasulfotole -
41 L-Glufosinate sodium Topramezone -
42 L-Glufosinate sodium Topramezone + bro- - moxynil
43 Glyphosate Pendimethalin -
44 Glyphosate Trifluralin -
45 Glyphosate Ethalfluralin -
46 Glyphosate Triallate -
47 Glyphosate Trifludimoxazin -
48 Glyphosate Saflufenacil -
49 Glyphosate Sulfentrazone -
50 Glyphosate Isoxaflutole -
51 Glyphosate Bicyclopyrone -
52 Glyphosate Tembotrione -
53 Glyphosate Mesotrione -
54 Glyphosate Pyrasulfotole -
55 Glyphosate Topramezone -
56 Glyphosate Topramezone + bro- - moxynil
57 Glyphosate dimethylammo- Pendimethalin - nium
58 Glyphosate dimethylammo- Trifluralin - nium
59 Glyphosate dimethylammo- Ethalfluralin - nium
60 Glyphosate dimethylammo- Triallate - nium
61 Glyphosate dimethylammo- Trifludimoxazin - nium
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
62 Glyphosate dimethylammo- Saflufenacil - nium
63 Glyphosate dimethylammo- Sulfentrazone - nium
64 Glyphosate dimethylammo- Isoxaflutole - nium
65 Glyphosate dimethylammo- Bicyclopyrone - nium
66 Glyphosate dimethylammo- Tembotrione - nium
67 Glyphosate dimethylammo- Mesotrione - nium
68 Glyphosate dimethylammo- Pyrasulfotole - nium
69 Glyphosate dimethylammo- Topramezone - nium
70 Glyphosate dimethylammo- Topramezone + bro- - nium moxynil
71 Glyphosate potassium Pendimethalin -
72 Glyphosate potassium Trifluralin -
73 Glyphosate potassium Ethalfluralin -
74 Glyphosate potassium Triallate -
75 Glyphosate potassium Trifludimoxazin -
76 Glyphosate potassium Saflufenacil -
77 Glyphosate potassium Sulfentrazone -
78 Glyphosate potassium Isoxaflutole -
79 Glyphosate potassium Bicyclopyrone -
80 Glyphosate potassium Tembotrione -
81 Glyphosate potassium Mesotrione -
82 Glyphosate potassium Pyrasulfotole -
83 Glyphosate potassium Topramezone -
84 Glyphosate potassium Topramezone + bro- - moxynil
85 Glyphosate isopropylammo- Pendimethalin - nium
86 Glyphosate isopropylammo- Trifluralin - nium
87 Glyphosate isopropylammo- Ethalfluralin - nium
88 Glyphosate isopropylammo- Triallate -
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
nium
89 Glyphosate isopropylammo- Trifludimoxazin - nium
90 Glyphosate isopropylammo- Saflufenacil - nium
91 Glyphosate isopropylammo- Sulfentrazone - nium
92 Glyphosate isopropylammo- Isoxaflutole - nium
93 Glyphosate isopropylammo- Bicyclopyrone - nium
94 Glyphosate isopropylammo- Tembotrione - nium
95 Glyphosate isopropylammo- Mesotrione - nium
96 Glyphosate isopropylammo- Pyrasulfotole - nium
97 Glyphosate isopropylammo- Topramezone - nium
98 Glyphosate isopropylammo- Topramezone + bro- - nium moxynil
99 Saflufenacil Pendimethalin -
100 Saflufenacil Trifluralin -
101 Saflufenacil Ethalfluralin -
102 Saflufenacil Triallate -
103 Saflufenacil Trifludimoxazin -
104 Saflufenacil Saflufenacil -
105 Saflufenacil Sulfentrazone -
106 Saflufenacil Isoxaflutole -
107 Saflufenacil Bicyclopyrone -
108 Saflufenacil Tembotrione -
109 Saflufenacil Mesotrione -
1 10 Saflufenacil Pyrasulfotole -
1 1 1 Saflufenacil Topramezone -
1 12 Saflufenacil Topramezone + bro- - moxynil
1 13 Trifludimoxazin Pendimethalin -
1 14 Trifludimoxazin Trifluralin -
1 15 Trifludimoxazin Ethalfluralin -
1 16 Trifludimoxazin Triallate -
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
1 17 Trifludimoxazin Trifludimoxazin -
1 18 Trifludimoxazin Saflufenacil -
1 19 Trifludimoxazin Sulfentrazone -
120 Trifludimoxazin Isoxaflutole -
121 Trifludimoxazin Bicyclopyrone -
122 Trifludimoxazin Tembotrione -
123 Trifludimoxazin Mesotrione -
124 Trifludimoxazin Pyrasulfotole -
125 Trifludimoxazin Topramezone -
126 Trifludimoxazin Topramezone + bro- - moxynil
127 Saflufenacil + trifludimoxazin Pendimethalin -
128 Saflufenacil + trifludimoxazin Trifluralin -
129 Saflufenacil + trifludimoxazin Ethalfluralin -
130 Saflufenacil + trifludimoxazin Triallate -
131 Saflufenacil + trifludimoxazin Trifludimoxazin -
132 Saflufenacil + trifludimoxazin Saflufenacil -
133 Saflufenacil + trifludimoxazin Sulfentrazone -
134 Saflufenacil + trifludimoxazin Isoxaflutole -
135 Saflufenacil + trifludimoxazin Bicyclopyrone -
136 Saflufenacil + trifludimoxazin Tembotrione -
137 Saflufenacil + trifludimoxazin Mesotrione -
138 Saflufenacil + trifludimoxazin Pyrasulfotole -
139 Saflufenacil + trifludimoxazin Topramezone -
140 Saflufenacil + trifludimoxazin Topramezone + bro- - moxynil
141 Dicamba Pendimethalin -
142 Dicamba Trifluralin -
143 Dicamba Ethalfluralin -
144 Dicamba Triallate -
145 Dicamba Trifludimoxazin -
146 Dicamba Saflufenacil -
147 Dicamba Sulfentrazone -
148 Dicamba Isoxaflutole -
149 Dicamba Bicyclopyrone -
150 Dicamba Tembotrione -
151 Dicamba Mesotrione -
152 Dicamba Pyrasulfotole -
153 Dicamba Topramezone -
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
154 Dicamba Topramezone + bro- - moxynil
155 Dicamba ethanolamine salt Pendimethalin -
156 Dicamba ethanolamine salt Trifluralin -
157 Dicamba ethanolamine salt Ethalfluralin -
158 Dicamba ethanolamine salt Triallate -
159 Dicamba ethanolamine salt Trifludimoxazin -
160 Dicamba ethanolamine salt Saflufenacil -
161 Dicamba ethanolamine salt Sulfentrazone -
162 Dicamba ethanolamine salt Isoxaflutole -
163 Dicamba ethanolamine salt Bicyclopyrone -
164 Dicamba ethanolamine salt Tembotrione -
165 Dicamba ethanolamine salt Mesotrione -
166 Dicamba ethanolamine salt Pyrasulfotole -
167 Dicamba ethanolamine salt Topramezone -
168 Dicamba ethanolamine salt Topramezone + bro- - moxynil
169 Dicamba diglycolamine salt Pendimethalin -
170 Dicamba diglycolamine salt Trifluralin -
171 Dicamba diglycolamine salt Ethalfluralin -
172 Dicamba diglycolamine salt Triallate -
173 Dicamba diglycolamine salt Trifludimoxazin -
174 Dicamba diglycolamine salt Saflufenacil -
175 Dicamba diglycolamine salt Sulfentrazone -
176 Dicamba diglycolamine salt Isoxaflutole -
177 Dicamba diglycolamine salt Bicyclopyrone -
178 Dicamba diglycolamine salt Tembotrione -
179 Dicamba diglycolamine salt Mesotrione -
180 Dicamba diglycolamine salt Pyrasulfotole -
181 Dicamba diglycolamine salt Topramezone -
182 Dicamba diglycolamine salt Topramezone + bro- - moxynil
183 Dicamba potassium Pendimethalin -
184 Dicamba potassium Trifluralin -
185 Dicamba potassium Ethalfluralin -
186 Dicamba potassium Triallate -
187 Dicamba potassium Trifludimoxazin -
188 Dicamba potassium Saflufenacil -
189 Dicamba potassium Sulfentrazone -
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
190 Dicamba potassium Isoxaflutole -
191 Dicamba potassium Bicyclopyrone -
192 Dicamba potassium Tembotrione -
193 Dicamba potassium Mesotrione -
194 Dicamba potassium Pyrasulfotole -
195 Dicamba potassium Topramezone -
196 Dicamba potassium Topramezone + bro- - moxynil
197 Dicamba BAPMA salt Pendimethalin -
198 Dicamba BAPMA salt Trifluralin -
199 Dicamba BAPMA salt Ethalfluralin -
200 Dicamba BAPMA salt Triallate -
201 Dicamba BAPMA salt Trifludimoxazin -
202 Dicamba BAPMA salt Saflufenacil -
203 Dicamba BAPMA salt Sulfentrazone -
204 Dicamba BAPMA salt Isoxaflutole -
205 Dicamba BAPMA salt Bicyclopyrone -
206 Dicamba BAPMA salt Tembotrione -
207 Dicamba BAPMA salt Mesotrione -
208 Dicamba BAPMA salt Pyrasulfotole -
209 Dicamba BAPMA salt Topramezone -
210 Dicamba BAPMA salt Topramezone + bro- - moxynil
21 1 - Pendimethalin -
212 - Trifluralin -
213 - Ethalfluralin -
214 - Triallate -
215 - Trifludimoxazin -
216 - Saflufenacil -
217 - Sulfentrazone -
218 - Isoxaflutole -
219 - Bicyclopyrone -
220 - Tembotrione -
221 - Mesotrione -
222 - Pyrasulfotole -
223 - Topramezone -
224 - Topramezone + bro- - moxynil
225 L-Glufosinate - -
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
226 L-Glufosinate ammonium - -
227 L-Glufosinate sodium - -
228 Glyphosate - -
229 Glyphosate dimethylammo- - - nium
230 Glyphosate potassium - -
231 Glyphosate isopropylammo- - - nium
232 Saflufenacil - -
233 Trifludimoxazin - -
234 Saflufenacil + trifludimoxazin - -
235 Dicamba - -
236 Dicamba ethanolamine salt - -
237 Dicamba diglycolamine salt - -
238 Dicamba potassium - -
239 Dicamba BAP MA salt - -
240 L-Glufosinate Pendimethalin Saflufenacil
241 L-Glufosinate Trifluralin Saflufenacil
242 L-Glufosinate Ethalfluralin Saflufenacil
243 L-Glufosinate Triallate Saflufenacil
244 L-Glufosinate Trifludimoxazin Saflufenacil
245 L-Glufosinate Saflufenacil Saflufenacil
246 L-Glufosinate Sulfentrazone Saflufenacil
247 L-Glufosinate Isoxaflutole Saflufenacil
248 L-Glufosinate Bicyclopyrone Saflufenacil
249 L-Glufosinate Tembotrione Saflufenacil
250 L-Glufosinate Mesotrione Saflufenacil
251 L-Glufosinate Pyrasulfotole Saflufenacil
252 L-Glufosinate Topramezone Saflufenacil
253 L-Glufosinate Topramezone + bro- Saflufenacil
moxynil
254 L-Glufosinate ammonium Pendimethalin Saflufenacil
255 L-Glufosinate ammonium Trifluralin Saflufenacil
256 L-Glufosinate ammonium Ethalfluralin Saflufenacil
257 L-Glufosinate ammonium Triallate Saflufenacil
258 L-Glufosinate ammonium Trifludimoxazin Saflufenacil
259 L-Glufosinate ammonium Saflufenacil Saflufenacil
260 L-Glufosinate ammonium Sulfentrazone Saflufenacil
261 L-Glufosinate ammonium Isoxaflutole Saflufenacil
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
262 L-Glufosinate ammonium Bicyclopyrone Saflufenacil
263 L-Glufosinate ammonium Tembotrione Saflufenacil
264 L-Glufosinate ammonium Mesotrione Saflufenacil
265 L-Glufosinate ammonium Pyrasulfotole Saflufenacil
266 L-Glufosinate ammonium Topramezone Saflufenacil
267 L-Glufosinate ammonium Topramezone + bro- Saflufenacil
moxynil
268 L-Glufosinate sodium Pendimethalin Saflufenacil
269 L-Glufosinate sodium Trifluralin Saflufenacil
270 L-Glufosinate sodium Ethalfluralin Saflufenacil
271 L-Glufosinate sodium Triallate Saflufenacil
272 L-Glufosinate sodium Trifludimoxazin Saflufenacil
273 L-Glufosinate sodium Saflufenacil Saflufenacil
274 L-Glufosinate sodium Sulfentrazone Saflufenacil
275 L-Glufosinate sodium Isoxaflutole Saflufenacil
276 L-Glufosinate sodium Bicyclopyrone Saflufenacil
277 L-Glufosinate sodium Tembotrione Saflufenacil
278 L-Glufosinate sodium Mesotrione Saflufenacil
279 L-Glufosinate sodium Pyrasulfotole Saflufenacil
280 L-Glufosinate sodium Topramezone Saflufenacil
281 L-Glufosinate sodium Topramezone + bro- Saflufenacil
moxynil
282 Glyphosate Pendimethalin Saflufenacil
283 Glyphosate Trifluralin Saflufenacil
284 Glyphosate Ethalfluralin Saflufenacil
285 Glyphosate Triallate Saflufenacil
286 Glyphosate Trifludimoxazin Saflufenacil
287 Glyphosate Saflufenacil Saflufenacil
288 Glyphosate Sulfentrazone Saflufenacil
289 Glyphosate Isoxaflutole Saflufenacil
290 Glyphosate Bicyclopyrone Saflufenacil
291 Glyphosate Tembotrione Saflufenacil
292 Glyphosate Mesotrione Saflufenacil
293 Glyphosate Pyrasulfotole Saflufenacil
294 Glyphosate Topramezone Saflufenacil
295 Glyphosate Topramezone + bro- Saflufenacil
moxynil
296 Glyphosate dimethylammo- Pendimethalin Saflufenacil
nium
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
297 Glyphosate dimethylammo- Trifluralin Saflufenacil
nium
298 Glyphosate dimethylammo- Ethalfluralin Saflufenacil
nium
299 Glyphosate dimethylammo- Triallate Saflufenacil
nium
300 Glyphosate dimethylammo- Trifludimoxazin Saflufenacil
nium
301 Glyphosate dimethylammo- Saflufenacil Saflufenacil
nium
302 Glyphosate dimethylammo- Sulfentrazone Saflufenacil
nium
303 Glyphosate dimethylammo- Isoxaflutole Saflufenacil
nium
304 Glyphosate dimethylammo- Bicyclopyrone Saflufenacil
nium
305 Glyphosate dimethylammo- Tembotrione Saflufenacil
nium
306 Glyphosate dimethylammo- Mesotrione Saflufenacil
nium
307 Glyphosate dimethylammo- Pyrasulfotole Saflufenacil
nium
308 Glyphosate dimethylammo- Topramezone Saflufenacil
nium
309 Glyphosate dimethylammo- Topramezone + bro- Saflufenacil
nium moxynil
310 Glyphosate potassium Pendimethalin Saflufenacil
31 1 Glyphosate potassium Trifluralin Saflufenacil
312 Glyphosate potassium Ethalfluralin Saflufenacil
313 Glyphosate potassium Triallate Saflufenacil
314 Glyphosate potassium Trifludimoxazin Saflufenacil
315 Glyphosate potassium Saflufenacil Saflufenacil
316 Glyphosate potassium Sulfentrazone Saflufenacil
317 Glyphosate potassium Isoxaflutole Saflufenacil
318 Glyphosate potassium Bicyclopyrone Saflufenacil
319 Glyphosate potassium Tembotrione Saflufenacil
320 Glyphosate potassium Mesotrione Saflufenacil
321 Glyphosate potassium Pyrasulfotole Saflufenacil
322 Glyphosate potassium Topramezone Saflufenacil
323 Glyphosate potassium Topramezone + bro- Saflufenacil
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
moxynil
324 Glyphosate isopropylammo- Pendimethalin Saflufenacil
nium
325 Glyphosate isopropylammo- Trifluralin Saflufenacil
nium
326 Glyphosate isopropylammo- Ethalfluralin Saflufenacil
nium
327 Glyphosate isopropylammo- Triallate Saflufenacil
nium
328 Glyphosate isopropylammo- Trifludimoxazin Saflufenacil
nium
329 Glyphosate isopropylammo- Saflufenacil Saflufenacil
nium
330 Glyphosate isopropylammo- Sulfentrazone Saflufenacil
nium
331 Glyphosate isopropylammo- Isoxaflutole Saflufenacil
nium
332 Glyphosate isopropylammo- Bicyclopyrone Saflufenacil
nium
333 Glyphosate isopropylammo- Tembotrione Saflufenacil
nium
334 Glyphosate isopropylammo- Mesotrione Saflufenacil
nium
335 Glyphosate isopropylammo- Pyrasulfotole Saflufenacil
nium
336 Glyphosate isopropylammo- Topramezone Saflufenacil
nium
337 Glyphosate isopropylammo- Topramezone + bro- Saflufenacil
nium moxynil
338 Saflufenacil Pendimethalin Saflufenacil
339 Saflufenacil Trifluralin Saflufenacil
340 Saflufenacil Ethalfluralin Saflufenacil
341 Saflufenacil Triallate Saflufenacil
342 Saflufenacil Trifludimoxazin Saflufenacil
343 Saflufenacil Saflufenacil Saflufenacil
344 Saflufenacil Sulfentrazone Saflufenacil
345 Saflufenacil Isoxaflutole Saflufenacil
346 Saflufenacil Bicyclopyrone Saflufenacil
347 Saflufenacil Tembotrione Saflufenacil
348 Saflufenacil Mesotrione Saflufenacil
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
349 Saflufenacil Pyrasulfotole Saflufenacil
350 Saflufenacil Topramezone Saflufenacil
351 Saflufenacil Topramezone + bro- Saflufenacil
moxynil
352 Trifludimoxazin Pendimethalin Saflufenacil
353 Trifludimoxazin Trifluralin Saflufenacil
354 Trifludimoxazin Ethalfluralin Saflufenacil
355 Trifludimoxazin Triallate Saflufenacil
356 Trifludimoxazin Trifludimoxazin Saflufenacil
357 Trifludimoxazin Saflufenacil Saflufenacil
358 Trifludimoxazin Sulfentrazone Saflufenacil
359 Trifludimoxazin Isoxaflutole Saflufenacil
360 Trifludimoxazin Bicyclopyrone Saflufenacil
361 Trifludimoxazin Tembotrione Saflufenacil
362 Trifludimoxazin Mesotrione Saflufenacil
363 Trifludimoxazin Pyrasulfotole Saflufenacil
364 Trifludimoxazin Topramezone Saflufenacil
365 Trifludimoxazin Topramezone + bro- Saflufenacil
moxynil
366 Saflufenacil + trifludimoxazin Pendimethalin Saflufenacil
367 Saflufenacil + trifludimoxazin Trifluralin Saflufenacil
368 Saflufenacil + trifludimoxazin Ethalfluralin Saflufenacil
369 Saflufenacil + trifludimoxazin Triallate Saflufenacil
370 Saflufenacil + trifludimoxazin Trifludimoxazin Saflufenacil
371 Saflufenacil + trifludimoxazin Saflufenacil Saflufenacil
372 Saflufenacil + trifludimoxazin Sulfentrazone Saflufenacil
373 Saflufenacil + trifludimoxazin Isoxaflutole Saflufenacil
374 Saflufenacil + trifludimoxazin Bicyclopyrone Saflufenacil
375 Saflufenacil + trifludimoxazin Tembotrione Saflufenacil
376 Saflufenacil + trifludimoxazin Mesotrione Saflufenacil
377 Saflufenacil + trifludimoxazin Pyrasulfotole Saflufenacil
378 Saflufenacil + trifludimoxazin Topramezone Saflufenacil
379 Saflufenacil + trifludimoxazin Topramezone + bro- Saflufenacil
moxynil
380 Dicamba Pendimethalin Saflufenacil
381 Dicamba Trifluralin Saflufenacil
382 Dicamba Ethalfluralin Saflufenacil
383 Dicamba Triallate Saflufenacil
384 Dicamba Trifludimoxazin Saflufenacil
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
385 Dicamba Saflufenacil Saflufenacil
386 Dicamba Sulfentrazone Saflufenacil
387 Dicamba Isoxaflutole Saflufenacil
388 Dicamba Bicyclopyrone Saflufenacil
389 Dicamba Tembotrione Saflufenacil
390 Dicamba Mesotrione Saflufenacil
391 Dicamba Pyrasulfotole Saflufenacil
392 Dicamba Topramezone Saflufenacil
393 Dicamba Topramezone + bro- Saflufenacil
moxynil
394 Dicamba ethanolamine salt Pendimethalin Saflufenacil
395 Dicamba ethanolamine salt Trifluralin Saflufenacil
396 Dicamba ethanolamine salt Ethalfluralin Saflufenacil
397 Dicamba ethanolamine salt Triallate Saflufenacil
398 Dicamba ethanolamine salt Trifludimoxazin Saflufenacil
399 Dicamba ethanolamine salt Saflufenacil Saflufenacil
400 Dicamba ethanolamine salt Sulfentrazone Saflufenacil
401 Dicamba ethanolamine salt Isoxaflutole Saflufenacil
402 Dicamba ethanolamine salt Bicyclopyrone Saflufenacil
403 Dicamba ethanolamine salt Tembotrione Saflufenacil
404 Dicamba ethanolamine salt Mesotrione Saflufenacil
405 Dicamba ethanolamine salt Pyrasulfotole Saflufenacil
406 Dicamba ethanolamine salt Topramezone Saflufenacil
407 Dicamba ethanolamine salt Topramezone + bro- Saflufenacil
moxynil
408 Dicamba diglycolamine salt Pendimethalin Saflufenacil
409 Dicamba diglycolamine salt Trifluralin Saflufenacil
410 Dicamba diglycolamine salt Ethalfluralin Saflufenacil
41 1 Dicamba diglycolamine salt Triallate Saflufenacil
412 Dicamba diglycolamine salt Trifludimoxazin Saflufenacil
413 Dicamba diglycolamine salt Saflufenacil Saflufenacil
414 Dicamba diglycolamine salt Sulfentrazone Saflufenacil
415 Dicamba diglycolamine salt Isoxaflutole Saflufenacil
416 Dicamba diglycolamine salt Bicyclopyrone Saflufenacil
417 Dicamba diglycolamine salt Tembotrione Saflufenacil
418 Dicamba diglycolamine salt Mesotrione Saflufenacil
419 Dicamba diglycolamine salt Pyrasulfotole Saflufenacil
420 Dicamba diglycolamine salt Topramezone Saflufenacil
421 Dicamba diglycolamine salt Topramezone + bro- Saflufenacil
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
moxynil
422 Dicamba potassium Pendimethalin Saflufenacil
423 Dicamba potassium Trifluralin Saflufenacil
424 Dicamba potassium Ethalfluralin Saflufenacil
425 Dicamba potassium Triallate Saflufenacil
426 Dicamba potassium Trifludimoxazin Saflufenacil
427 Dicamba potassium Saflufenacil Saflufenacil
428 Dicamba potassium Sulfentrazone Saflufenacil
429 Dicamba potassium Isoxaflutole Saflufenacil
430 Dicamba potassium Bicyclopyrone Saflufenacil
431 Dicamba potassium Tembotrione Saflufenacil
432 Dicamba potassium Mesotrione Saflufenacil
433 Dicamba potassium Pyrasulfotole Saflufenacil
434 Dicamba potassium Topramezone Saflufenacil
435 Dicamba potassium Topramezone + bro- Saflufenacil
moxynil
436 Dicamba BAPMA salt Pendimethalin Saflufenacil
437 Dicamba BAPMA salt Trifluralin Saflufenacil
438 Dicamba BAPMA salt Ethalfluralin Saflufenacil
439 Dicamba BAPMA salt Triallate Saflufenacil
440 Dicamba BAPMA salt Trifludimoxazin Saflufenacil
441 Dicamba BAPMA salt Saflufenacil Saflufenacil
442 Dicamba BAPMA salt Sulfentrazone Saflufenacil
443 Dicamba BAPMA salt Isoxaflutole Saflufenacil
444 Dicamba BAPMA salt Bicyclopyrone Saflufenacil
445 Dicamba BAPMA salt Tembotrione Saflufenacil
446 Dicamba BAPMA salt Mesotrione Saflufenacil
447 Dicamba BAPMA salt Pyrasulfotole Saflufenacil
448 Dicamba BAPMA salt Topramezone Saflufenacil
449 Dicamba BAPMA salt Topramezone + bro- Saflufenacil
moxynil
450 - Pendimethalin Saflufenacil
451 - Trifluralin Saflufenacil
452 - Ethalfluralin Saflufenacil
453 - Triallate Saflufenacil
454 - Trifludimoxazin Saflufenacil
455 - Saflufenacil Saflufenacil
456 - Sulfentrazone Saflufenacil
457 - Isoxaflutole Saflufenacil
Treatment Pre-plant burn-down Pre-emergence or pre- Pre-harvest desiccombination plant control of volunteer cation
canola
458 - Bicyclopyrone Saflufenacil
459 - Tembotrione Saflufenacil
460 - Mesotrione Saflufenacil
461 - Pyrasulfotole Saflufenacil
462 - Topramezone Saflufenacil
463 - Topramezone + bro- Saflufenacil
moxynil
464 L-Glufosinate - Saflufenacil
465 L-Glufosinate ammonium - Saflufenacil
466 L-Glufosinate sodium - Saflufenacil
467 Glyphosate - Saflufenacil
468 Glyphosate dimethylammo- - Saflufenacil
nium
469 Glyphosate potassium - Saflufenacil
470 Glyphosate isopropylammo- - Saflufenacil
nium
471 Saflufenacil - Saflufenacil
472 Trifludimoxazin - Saflufenacil
473 Saflufenacil + trifludimoxazin - Saflufenacil
474 Dicamba - Saflufenacil
475 Dicamba ethanolamine salt - Saflufenacil
476 Dicamba diglycolamine salt - Saflufenacil
477 Dicamba potassium - Saflufenacil
478 Dicamba BAP MA salt - Saflufenacil
The treatment combinations 2.1 to 2.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium.
The treatment combinations 3.1 to 3.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium.
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 6.1 to 6.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and clethodim.
The treatment combinations 7.1 to 7.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and cycloxydim.
The treatment combinations 8.1 to 8.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and cycloxydim.
The treatment combinations 9.1 to 9.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and cycloxydim.
The treatment combinations 10.1 to 10.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and sethoxydim. The treatment combinations 1 1.1 to 1 1.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and sethoxydim.
The treatment combinations 12.1 to 12.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and sethoxydim.
The treatment combinations 13.1 to 13.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and tepraloxydim. The treatment combinations 14.1 to 14.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and tepraloxydim.
The treatment combinations 15.1 to 15.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and tepraloxydim.
The treatment combinations 16.1 to 16.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and fenoxaprop-P- ethyl.
The treatment combinations 17.1 to 17.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and fenoxaprop-P-ethyl.
The treatment combinations 18.1 to 18.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and fenoxaprop-P-ethyl.
The treatment combinations 19.1 to 19.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and haloxyfop-P- ethyl.
The treatment combinations 20.1 to 20.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and haloxyfop-P-ethyl.
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.
The treatment combinations 23.1 to 23.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate ammonium and quizalofop-P-tefuryl.
The treatment combinations 24.1 to 24.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate sodium and quizalo- fop- P-tefury I.
The treatment combinations 25.1 to 25.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate and quinclorac. The treatment combinations 26.1 to 26.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate ammonium and quinclorac.
The treatment combinations 27.1 to 27.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate sodium and quin- clorac.
The treatment combinations 28.1 to 28.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate and quinclorac di- methylamine salt.
The treatment combinations 29.1 to 29.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate ammonium and quinclorac dimethylamine salt.
The treatment combinations 30.1 to 30.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate sodium and quin- clorac dimethylamine salt.
The treatment combinations 31.1 to 31.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate, quinclorac and clethodim.
The treatment combinations 32.1 to 32.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate ammonium, quin- clorac and clethodim.
The treatment combinations 33.1 to 33.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate sodium, quinclorac and clethodim.
The treatment combinations 34.1 to 34.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate, quinclorac dime- thylamine salt and clethodim.
The treatment combinations 35.1 to 35.478 in which one of the trea ment combinations listed in the preceeding table is combined with post- emergence use of L-glu osinate ammonium, quin- clorac dimethylamine salt and clethodim.
The treatment combinations 36.1 to 36.478 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 clethodim.
The treatment combinations 37.1 to 37.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac and cy- cloxydim.
The treatment combinations 38.1 to 38.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quinclorac and cycloxydim.
The treatment combinations 39.1 to 39.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium, quinclorac and cycloxydim.
The treatment combinations 40.1 to 40.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac dime- thylammonium and cycloxydim.
The treatment combinations 41.1 to 41 .478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quinclorac dimethylammonium and cycloxydim.
The 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 43.1 to 43.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac and sethoxydim.
The treatment combinations 44.1 to 44.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quinclorac and sethoxydim.
The treatment combinations 45.1 to 45.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium, quinclorac and sethoxydim.
The treatment combinations 46.1 to 46.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac dimethylamine salt and sethoxydim.
The treatment combinations 47.1 to 47.478 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 sethoxydim.
The treatment combinations 48.1 to 48.478 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 sethoxydim.
The treatment combinations 49.1 to 49.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate, quinclorac and tepraloxydim.
The treatment combinations 50.1 to 50.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate ammonium, quin- clorac and tepraloxydim.
The treatment combinations 51.1 to 51.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate sodium, quinclorac and tepraloxydim.
The treatment combinations 52.1 to 52.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate, quinclorac dime- thylamine salt and tepraloxydim.
The treatment combinations 53.1 to 53.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate ammonium, quin- clorac dimethylamine salt and tepraloxydim.
The treatment combinations 54.1 to 54.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate sodium, quinclorac dimethylamine salt and tepraloxydim.
The treatment combinations 55.1 to 55.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate, quinclorac and fenoxaprop-P-ethyl.
The treatment combinations 56.1 to 56.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate ammonium, quin- clorac and fenoxaprop-P-ethyl.
The treatment combinations 57.1 to 57.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate sodium, quinclorac and fenoxaprop-P-ethyl.
The treatment combinations 58.1 to 58.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate, quinclorac dime- thylamine salt and fenoxaprop-P-ethyl.
The treatment combinations 59.1 to 59.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate ammonium, quin- clorac dimethylamine salt and fenoxaprop-P-ethyl.
The treatment combinations 60.1 to 60.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate sodium, quinclorac dimethylamine salt and fenoxaprop-P-ethyl.
The treatment combinations 61.1 to 61.478 in which one of the trea ment combinations listed in the preceeding table is combined with post-emergence use of L-glu osinate, quinclorac and ha- loxyfop-P-ethyl.
The treatment combinations 62.1 to 62.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quin- clorac and haloxyfop-P-ethyl.
The treatment combinations 63.1 to 63.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium, quinclorac and haloxyfop-P-ethyl.
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.
The 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.
The 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.
The treatment combinations 67.1 to 67.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac and quizalofop-P-tefuryl.
The treatment combinations 68.1 to 68.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium, quinclorac and quizalofop-P-tefuryl.
The treatment combinations 69.1 to 69.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium, quinclorac and quizalofop-P-tefuryl.
The treatment combinations 70.1 to 70.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate, quinclorac dimethylamine salt and quizalofop-P-tefuryl.
The 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 treatment combinations 72.1 to 72.478 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 quizalofop-P-tefuryl.
The treatment combinations 73.1 to 73.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of imazamox.
The treatment combinations 74.1 to 74.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of imazamox ammonium.
The treatment combinations 75.1 to 75.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of imazapyr.
The treatment combinations 76.1 to 76.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of imazapyr isopropylammonium.
The treatment combinations 77.1 to 77.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of imazapyr and imazamox.
The treatment combinations 78.1 to 78.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of imazapyr isopropylammonium and imazamox ammonium.
The treatment combinations 79.1 to 79.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of tribenuron-methyl.
The treatment combinations 80.1 to 80.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of florasulam.
The treatment combinations 81.1 to 81.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of ethametsulfuron-methyl.
The treatment combinations 82.1 to 82.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of carfentrazone-ethyl.
The treatment combinations 83.1 to 83.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of saflufenacil.
The treatment combinations 84.1 to 84.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of trifludimoxazin.
The treatment combinations 85.1 to 85.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of sulfentrazone.
The treatment combinations 86.1 to 86.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of mesotrione.
The treatment combinations 87.1 to 87.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of topramezone.
The treatment combinations 88.1 to 88.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of tembotrione.
The treatment combinations 89.1 to 89.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of pyrasulfotole.
The treatment combinations 90.1 to 90.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of bicyclopyrone.
The treatment combinations 91.1 to 91.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of 2,4-D.
The treatment combinations 92.1 to 92.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of 2,4-D choline salt.
The treatment combinations 93.1 to 93.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of dicamba.
The treatment combinations 94.1 to 94.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of dicamba sodium.
The treatment combinations 95.1 to 95.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of dicamba ethanolamine salt. The treatment combinations 96.1 to 96.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of dicamba diglycolamine salt.
The treatment combinations 97.1 to 97.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of dicamba potassium.
The treatment combinations 98.1 to 98.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of dicamba BAPMA salt.
The treatment combinations 99.1 to 99.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of aminopyralid.
The treatment combinations 100.1 to 100.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of aminopyralid triisopropylamine salt.
The treatment combinations 101.1 to 101 .478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of clopyralid.
The treatment combinations 102.1 to 102.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of clopyralid ethanolamine salt. The treatment combinations 103.1 to 103.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of picloram.
The treatment combinations 104.1 to 104.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of picloram potassium.
The treatment combinations 105.1 to 105.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of fluroxypyr.
The treatment combinations 106.1 to 106.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of fluroxypyr 1 -methylheptyl ester. The treatment combinations 107.1 to 107.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate and 4-amino-3- chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (II-93).
The treatment combinations 108.1 to 108.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate ammonium and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (II-93).
The treatment combinations 109.1 to 109.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of L-glufosinate sodium and 4- amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (II-93).
The treatment combinations 1 10.1 to 1 10.478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of 4-amino-3-chloro-5-fluoro-6-(7- fluoro-1 H-indol-6-yl)-2-pyridinecarboxylic acid (II-93).
The treatment combinations 1 1 1.1 to 1 1 1 .478 in which one of the treatment combinations listed in the preceeding table is combined with post-emergence use of tolpyralate.
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.
While 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. As mentioned above, the inventive mixtures are suitable for controlling a large number of harmful plants in glufosinate tolerant canola
Thus, the term " glufosinate tolerant canola" as used herein 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. Typically, 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 Link™ Independence™), HCN28 (T45) (event code: ACS-BN008-2, gene: pat, e.g. commercially available as InVigor™ Canola), HCN92 (Topas 19/2 (event code: ACS-BN007-1 , gene: bar, e.g. commercially available as Liberty Link™ Innovator™), MS1 (B91 -4) (event code: ACS-BN004-7, gene: bar, e.g. commercially available as InVigor™ Canola), MS1 x RF1 (PGS1 ) (event code: ACS-BN004-7 x ACS-BN001 -4, gene: bar, e.g. commercially available as InVigor™ Canola), MS1 x RF2 (PGS2) (event code: ACS-BN004-7 x ACS-BN002-5, gene: bar, e.g. commercially available as InVigor™ Canola), MS1 x RF3 (event code: ACS-BN004-7 x ACS-BN003-6, gene: bar, e.g. commercially available as InVigor™ Canola), MS8 (event code: ACS-BN005-8, gene: bar, e.g. commercially available as InVigor™ Canola), MS8 x RF3 (event code: ACS-BN005-8 x ACS-BN003-6, gene: bar, e.g. commercially available as InVigor™ Canola), RF1 (B93-101 ) (event code: ACS-BN001 -4, gene: bar, e.g. commercially availa- ble as InVigor™ Canola), RF2 (B94-2) (event code: ACS-BN002-5, gene: bar, e.g. commercially available as InVigor™ Canola), RF3 (event code: ACS-BN003-6, gene: bar, e.g. commercially available as InVigor™ Canola), MS1 x MON88302 (event code: ACS-BN004-7 x MON- 88302-9, gene: bar, e.g. commercially available as InVigor™ x TruFlex™ Roundup Ready™
Canola), MS8 x MON88302 (event code: ACS-BN005-8 x MON-88302-9, gene: bar, e.g.
commercially available as InVigor™ x TruFlex™ Roundup Ready™ Canola), RF1 x MON88302 (event code: ACS-BN001 -4 x MON-88302-9, gene: bar, e.g. commercially available as InVigor™ x TruFlex™ Roundup Ready™ Canola), RF2 x MON88302 (event code: ACS-BN002-5 x MON-88302-9, gene: bar, e.g. commercially available as InVigor™ x TruFlex™ Roundup Ready™ Canola), HCN28 x MON88302 (event code: ACS-BN008-2 x MON-88302-9, gene: pat, e.g. commercially available as InVigor™ x TruFlex™ Roundup Ready™ Canola), HCN92 x MON88302 (event code: ACS-BN007-1 x MON-88302-9, gene: bar, e.g. commercially available as Liberty Link™ Innovator™ x TruFlex™ Roundup Ready™ Canola), HCR-1 (gene: pat), MON88302 x MS8 x RF3 (event code: MON-88302-9 x ACS-BN005-8 x ACS-BN003-6, gene: bar), MON88302 x RF3 (event code: MON-88302-9 x ACS-BN003-6, gene: bar), MS8 x RF3 x GT73 (RT73) (event code:, gene: bar), PHY14 (event code: ACS-BN005-8 x ACS-BN003-6 x MON-00073-7, gene: bar), PHY23 (gene: bar), PHY35 (gene: bar) and PHY36 (gene: bar) and 73496 x RF3 (event code: DP-073496-4 x ACS-BN003-6, gene: bar).
In other aspects, 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. isoxaflutole, mesotrione, tembotrione, topramezone, bicyclopyrone) or phytoene desaturase (PDS) inhibitors; 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), and "dens" (such as pinoxaden); or oxynil {i.e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Thus, 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, dicamba, AHAS inhibitors and PPO inhibitors; glyphosate, 2,4-D, AHAS inhibitors and PPO inhibitors; glyphosate, dicamba, glufosinate, AHAS inhibitors and PPO inhibitors; glyphosate, 2,4-D, glufosinate, AHAS inhibitors and PPO inhibitors; glyphosate, PPO inhibitors, AHAS inhibitors and HPPD inhibitors; glufosinate, HPPD inhibitors, AHAS inhibitors and PPO inhibitors; glyphosate, glufosinate, HPPD inhibitors, AHAS inhibitors and PPO inhibitors; glyphosate, dicamba, HPPD inhibitors, AHAS inhibitors and PPO inhibitors; glypho- sate, 2,4-D, HPPD inhibitors, AHAS inhibitors and PPO inhibitors; glyphosate, dicamba, glufosinate, HPPD inhibitors, AHAS inhibitors and PPO inhibitors; glyphosate, 2,4-D, glufosinate, HPPD inhibitors, AHAS inhibitors and PPO inhibitors; or to one of the aforementioned canola plants that are tolerant to further classes of herbicides such as ACCase inhibitors. These 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. In addition to these classes of inhibitors, 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.
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.
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.
In all treatments according to the methods of the present invention, 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.
In one embodiment, 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.
In general, 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.).
The examples which follow illustrate the invention without imposing any limitation. Biological examples
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):
When the observed combined control effect is greater than the expected (calculated) combined control effect (E), then the combined effect is synergistic.
The following tests demonstrate the control efficacy of compounds, mixtures or compositions of this invention on specific weeds. However, the weed control afforded by the compounds, mix- tures or compositions is not limited to these species. The analysis of synergism or antagonism between the mixtures or compositions was determined using Colby's equation.
Test method:
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. For the pre-emergence treatment, 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. For the post-emergence treatment, the 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. For this purpose, 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. Depending on the species, 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.
Products:
L-Glufosinate: 5 % EC formulation
Saflufenacil: 342 g/l SC formulation
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
Pyroxasulfone: 85 % WG formulation
Pethoxamid: 5 % EC 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
S-Metolachlor: 960 g/l EC formulation
Sulfentrazone: 480 g/l SC formulation
Weeds in the study:
EPPO Code Scientific Name
ABUTH Abutilon theophrasti
ECHCG Echinochloa crus-galli
AVE FA Avena fatua
SETVI Setaria viridis
COMBE Commelina benghalensis
KCHSC Kochia scoparia
CHEAL Chenopodium album
AVE FA Avena fatua
CYPIR Cyperus iria
ERICA Erigeron Canadensis, Conyza canadensis
Example 1 : Post emergence treatment with the mixture of L-glufosinate with saflufenacil
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 3: Post emergence treatment with the mixture of L-glufosinate with trifludimoxazin
Herbicidal activity against
Application rate in g ai/ha
ECHCG
L-Glufosinate Trifludimoxazin Found Calculated
400 — 65 —
— 0.25 10 —
400 0.25 75 69
200 — 0 —
— 0.25 10 —
200 0.25 33 10
Example 4: Post emergence treatment with the mixture of L-glufosinate with pyroxasulfone
Example 5: Post emergence treatment with the mixture of L-glufosinate with pethoxamid
Example 6: Post emergence treatment with the mixture of L-glufosinate with 2,4-D dime- thylammonium salt
Herbicidal activity against
Application rate in g ai/ha
AVE FA SETVI
2,4-D as dime¬
L-Glufosinate thyl-ammonium Found Calculated Found Calculated
salt
100 — 35 — 30 —
— 140 0 — 0 —
100 140 65 35 65 30
100 — 35 — 30 —
— 70 0 — 0 —
100 70 40 35 65 30
Example 7: Post emergence treatment with the mixture of L-glufosinate with dicamba dime- thylammonium salt
Example 8: Post emergence treatment with the mixture of L-glufosinate with bicyclopyrone
Herbicidal activity against
Application rate in g ai/ha
COMBE ECHCG
L-Glufosinate Bicyclopyrone Found Calculated Found Calculated
100 — 0 — 0 —
— 2 10 — 0 —
100 2 30 10 55 0
100 — 0 — 0 —
— 1 0 — 0 —
100 1 25 0 30 0
Example 9: Post emergence treatment with the mixture of L-glufosinate with dimethenamid-P
Example 10: Post emergence treatment with the mixture of L-glufosinate with S-metolachlor
Example 1 1 : Post emergence treatment with the mixture of L-glufosinate with sulfentrazone
Herbicidal activity against
Application rate in g ai/ha
ERICA
L-Glufosinate Sulfentrazone Found Calculated
75 — 90 —
— 2.5 0 —
75 2.5 100 90
75 — 90 —
— 1 .25 0 —
75 1 .25 100 90
Example 12: Post emergence treatment with the mixture of L-glufosinate with tembotrione
Example 13: Post emergence treatment with the mixture of L-glufosinate with bicyclopyrone
Example 14: Post emergence treatment with the mixture of L-glufosinate with topramezone
Herbicidal activity against
Application rate in g ai/ha
ECHCG
L-Glufosinate Topramezone Found Calculated
200 — 0 —
— 1 0 —
200 1 90 0
100 — 0 —
— 1 0 —
100 1 35 0
Claims (1)
- Use of a herbicidal mixture for controlling undesirable vegetation in canola, wherein the herbicidal mixture comprises1 ) L- glufosinate and its salts, and2) a herbicidal compound II selected from the group consisting of clethodim, cy- cloxydim, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazi- fop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, ha- loxyfop-P, haloxyfop-P-methyl, propaquizafop, quizalofop, quizalofop-ethyl, quizalo- fop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, tepraloxydim, ethametsulfuron, ethametsulfuron-methyl, tritosulfuron, imazamethabenz, imaza- methabenz-methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, tribenuron-methyl, florasulam, cyanazine, bromoxynil and its salts and esters, bentazone, bentazone-sodium, pyridate, carfentrazone, carfentrazone-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, pyraflufen-ethyl, flumioxazin, tiafenacil, picolinafen, clomazone, mesotrione, tembotrione, pyrasulfotole, bicyclopyrone, tolpyralate, fenquinotrione, ethalfluralin, pendimethalin, triallate, trifluralin, propyza- mide, carbetamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, amino- pyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, diflufenzopyr, diflufenzopyr- sodium, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dime- thylammonium, 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, topramezone, sethoxydim, pethoxamid, clopyralid, picloram, fluroxypyr, 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), II-85: 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N- (methylsulfonyl)-acetamide (CAS 2158276-22-1 ), II-86: 2-[[3-[[3-chloro-6-[3,6- dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid ethyl ester (CAS 2158274-56-5), 11-87: 2- [2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53- 2), II-88: 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)- pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid ethyl ester (CAS 2158274- 50-9), II-89: ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1 - yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), II-90: 2-[[3-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 11-91 : 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)- pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS2158274-96-3) and II-92: methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5- oxo-1 ,2,4-triazol-1 -yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate,wherein L-glufosinate comprises more than 70% by weight of the L-enantiomer.The use as claimed in claim 1 , wherein compound I in the herbicidal mixture is selected from the group consisting of L-glufosinate-ammonium or L-glufosinate-sodium as L- glufosinate salts and L-glufosinate as free acid.The use as claimed in claim 1 , wherein compound I in the herbicidal mixture is L- glufosinate-ammonium.The use as claimed in any of claims 1 to 3, wherein L-glufosinate in the herbicidal mixture comprises more than 80% by weight, preferably more than 90% by weight, even more preferably 95% by weight of the L-enantiomer.The use as claimed in any of claims 1 to 3, wherein compound II in the herbicidal mixture is 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, quizalo- fop-P-tefuryl, tepraloxydim, ethametsulfuron, ethametsulfuron-methyl, imazamox, imaza- mox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropylammonium, imazethapyr, imazethapyr ammonium, cyanazine, bromoxynil and its salts and esters, pyr- idate, carfentrazone, carfentrazone-ethyl, saflufenacil, trifludimoxazin, clomazone, meso- trione, fenquinotrione, ethalfluralin, pendimethalin, trifluralin, propyzamide, carbetamide, acetochlor, alachlor, butachlor, dimethachlor, metazachlor, metolachlor, S-metolachlor, napropamide, napropamide-M, 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quin- merac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dime- thylammonium, topramezone, sethoxydim, pethoxamid, clopyralid and picloram; preferably wherein compound II is 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, bromoxynil and its salts and esters, carfentrazone, carfentrazone-ethyl, saflufenacil, trifludimoxazin, clomazone, fenquinotrione, ethalfluralin, pendimethalin, trifluralin, propyzamide, acetochlor, butachlor, dimethachlor, metazachlor, napropamide, napropamide-M, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, quinmerac, cinmethylin, dimethenamid, dimethenamid-P, quinclorac, quinclorac dimethylammonium, topramezone, sethoxydim, pethoxamid, clopyralid and picloram.The use as claimed in any of claims 1 to 4 wherein the compound II in the herbicidal mixture is selected from the group of imazapyr, tribenuron-methyl, florasulam; carfentrazone- ethyl, trifludimoxazin, sulfentrazone, pyraflufen-ethyl, tiafenacil, compounds II-83, II-84, lies, II-86, II-87, II-88, II-89, II-90, 11-91 , II-92; mesotrione, topramezone, bromoxynil, tem- botrione, pyrasulfotole, bicyclopyrone, tolpyralate; 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, flurox- ypyr, pendimethalin, ethalfluralin and triallate; preferably selected from the group 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; 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.The use as claimed in any of claims 1 to 6, wherein the compound II in the herbicidal mixture is selected from the group 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 and II-92.The use as claimed in any of claims 1 to 6, wherein the compound II in the herbicidal mixture is selected from the group of mesotrione, topramezone, bromoxynil, tembotrione, pyrasulfotole, bicyclopyrone and tolpyralate;preferably selected from the group of mesotrione, topramezone, tembotrione, pyrasulfotole, bicyclopyrone and tolpyralate.The use as claimed in any of claims 1 to 6, wherein the compound II in the herbicidal mixture is selected from the group of 4-amino-3-chloro-5-f!uoro-6-(7-fluoro-1 H-indol-6-yl)-2- pyridinecarboxylic acid (II-93; 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; preferably selected from the group of 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)- 2-pyridinecarboxylic acid (Π-93; CAS 628702-28-2) and its salts and esters; or preferably selected from the group of 2,4-D and its salts and esters, dicamba and its salts and esters; or preferably selected from the group of picloram and fluroxypyr.10. The use as claimed as claimed in any of claims 1 to 5, wherein the weight ratio of compound I to compound II is from 1000:1 to 1 :500;. preferably wherein the weight ratio of compound I to compound II is from 500:1 to 1 :250.1 1 . A pesticidal mixture, wherein the compounds I and II are as defined in any of claims 1 to 10.12. A pesticidal composition, comprising a liquid or solid carrier and a mixture as defined in any of claims 1 to 10.13. A method for controlling undesirable vegetation in glufosinate tolerant canola, whichmethod comprises applying a mixture as defined in claims 1 to 10 to the undesirable vegetation or the locus thereof or applying to the soil or water.14. The method as claimed in claim 13, wherein the glufosinate tolerant canola is a transgenic canola plant.15. The method as claimed in any of claims 13 to 14, wherein compounds I and II of the mixture as defined in any of claims 1 to 10 are applied simultaneously, that is jointly or separately, or in succession.
Applications Claiming Priority (3)
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EP17185466 | 2017-08-09 | ||
EP17185466.4 | 2017-08-09 | ||
PCT/EP2018/070928 WO2019030086A2 (en) | 2017-08-09 | 2018-08-02 | Herbicidal mixtures comprising l-glufosinate and their use in canola cultures |
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AU2018314499A1 AU2018314499A1 (en) | 2020-02-13 |
AU2018314499B2 true AU2018314499B2 (en) | 2024-06-13 |
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