US20060111240A1 - Herbicidal compositions for tolerant or resistant maize crops - Google Patents
Herbicidal compositions for tolerant or resistant maize crops Download PDFInfo
- Publication number
- US20060111240A1 US20060111240A1 US11/323,085 US32308505A US2006111240A1 US 20060111240 A1 US20060111240 A1 US 20060111240A1 US 32308505 A US32308505 A US 32308505A US 2006111240 A1 US2006111240 A1 US 2006111240A1
- Authority
- US
- United States
- Prior art keywords
- herbicides
- salts
- group
- esters
- glufosinate
- 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.)
- Abandoned
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 105
- 240000008042 Zea mays Species 0.000 title claims abstract description 71
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 title claims abstract description 63
- 235000002017 Zea mays subsp mays Nutrition 0.000 title claims abstract description 63
- 235000009973 maize Nutrition 0.000 title claims abstract description 63
- 239000000203 mixture Substances 0.000 title claims description 64
- 239000004009 herbicide Substances 0.000 claims abstract description 134
- 241000196324 Embryophyta Species 0.000 claims abstract description 112
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000005562 Glyphosate Substances 0.000 claims abstract description 19
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000005561 Glufosinate Substances 0.000 claims abstract description 16
- 229940097068 glyphosate Drugs 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims abstract description 11
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims description 53
- 101100377706 Escherichia phage T5 A2.2 gene Proteins 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 29
- 238000009472 formulation Methods 0.000 claims description 25
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical class CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 claims description 14
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 11
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 11
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 10
- 239000005504 Dicamba Substances 0.000 claims description 10
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 claims description 10
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 claims description 10
- 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 description 9
- MBFHUWCOCCICOK-UHFFFAOYSA-N 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(I)C=2)C(O)=O)=N1 MBFHUWCOCCICOK-UHFFFAOYSA-N 0.000 claims description 9
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims description 9
- 239000005606 Pyridate Substances 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 9
- 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 description 8
- 239000005489 Bromoxynil Substances 0.000 claims description 8
- 239000005568 Iodosulfuron Substances 0.000 claims description 8
- 239000005604 Prosulfuron Substances 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 8
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 claims description 8
- 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 description 8
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 claims description 7
- 239000005591 Pendimethalin Substances 0.000 claims description 7
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 7
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 6
- KFEFNHNXZQYTEW-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methylbenzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(C)=CC=C1C(O)=O KFEFNHNXZQYTEW-UHFFFAOYSA-N 0.000 claims description 6
- 239000005586 Nicosulfuron Substances 0.000 claims description 6
- 239000005621 Terbuthylazine Substances 0.000 claims description 6
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 6
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 6
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 6
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 6
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims description 6
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000005500 Clopyralid Substances 0.000 claims description 5
- 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 description 5
- 239000005571 Isoxaflutole Substances 0.000 claims description 5
- 239000005618 Sulcotrione Substances 0.000 claims description 5
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 claims description 5
- 229940088649 isoxaflutole Drugs 0.000 claims description 5
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 4
- 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 description 4
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 239000005566 Imazamox Substances 0.000 claims description 4
- 239000005981 Imazaquin Substances 0.000 claims description 4
- 239000005616 Rimsulfuron Substances 0.000 claims description 4
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 claims description 4
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims 4
- -1 sulfosate Chemical class 0.000 abstract description 18
- 230000009261 transgenic effect Effects 0.000 abstract description 17
- 239000003112 inhibitor Substances 0.000 abstract description 11
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 abstract description 8
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 abstract description 6
- 150000003851 azoles Chemical class 0.000 abstract description 4
- 241001233957 eudicotyledons Species 0.000 abstract description 4
- 102100029028 Protoporphyrinogen oxidase Human genes 0.000 abstract 2
- 239000013543 active substance Substances 0.000 description 81
- 239000005022 packaging material Substances 0.000 description 46
- 230000000694 effects Effects 0.000 description 31
- 239000000126 substance Substances 0.000 description 24
- 239000004495 emulsifiable concentrate Substances 0.000 description 20
- 239000002689 soil Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000004702 methyl esters Chemical class 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- 230000002195 synergetic effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000004562 water dispersible granule Substances 0.000 description 7
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 description 6
- 230000001276 controlling effect Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 6
- 238000010353 genetic engineering Methods 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 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 description 4
- 239000005531 Flufenacet Substances 0.000 description 4
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 4
- 241001148683 Zostera marina Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 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 description 4
- 238000002360 preparation method Methods 0.000 description 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 4
- LNGRZPZKVUBWQV-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LNGRZPZKVUBWQV-UHFFFAOYSA-N 0.000 description 3
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 3
- 108010000700 Acetolactate synthase Proteins 0.000 description 3
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 3
- LQQGJJNFZNFZJD-UHFFFAOYSA-N CC(=O)C(N)CCP(C)(=O)O Chemical compound CC(=O)C(N)CCP(C)(=O)O LQQGJJNFZNFZJD-UHFFFAOYSA-N 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 239000005574 MCPA Substances 0.000 description 3
- 239000005578 Mesotrione Substances 0.000 description 3
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 108091028043 Nucleic acid sequence Proteins 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 239000005600 Propaquizafop Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 3
- 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 description 3
- 238000012552 review Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 2
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 description 2
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005498 Clodinafop Substances 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 244000048459 Euphorbia cyathophora Species 0.000 description 2
- 239000005529 Florasulam Substances 0.000 description 2
- 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 description 2
- 241001101998 Galium Species 0.000 description 2
- LXKOADMMGWXPJQ-UHFFFAOYSA-N Halosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C(O)=O)C)=N1 LXKOADMMGWXPJQ-UHFFFAOYSA-N 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 239000005573 Linuron Substances 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 239000005582 Metosulam Substances 0.000 description 2
- 239000005583 Metribuzin Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 239000005609 Quizalofop-P Substances 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 239000005619 Sulfosulfuron Substances 0.000 description 2
- 239000005629 Tritosulfuron Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 description 2
- YIANBKOBVRMNPR-UHFFFAOYSA-N cloransulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(O)=O YIANBKOBVRMNPR-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004807 localization Effects 0.000 description 2
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010187 selection method Methods 0.000 description 2
- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 230000009105 vegetative growth Effects 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- ROBSGBGTWRRYSK-SNVBAGLBSA-N (2r)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C#N)C=C1F ROBSGBGTWRRYSK-SNVBAGLBSA-N 0.000 description 1
- MPPOHAUSNPTFAJ-SECBINFHSA-N (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-SECBINFHSA-N 0.000 description 1
- IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- 0 */N=C1\SC(=O)N2CCCCN12 Chemical compound */N=C1\SC(=O)N2CCCCN12 0.000 description 1
- GBJNDHJOGWZEJL-UHFFFAOYSA-N 1-tert-butyl-3-ethyl-6-methylsulfanyl-2,4-dihydro-1,3,5-triazine-2,4-diamine Chemical compound CCN1C(N)N=C(SC)N(C(C)(C)C)C1N GBJNDHJOGWZEJL-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- SILSDTWXNBZOGF-SUJSHMTESA-N 2-[(Z)-N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-5-(2-ethylsulfanylpropyl)-3-hydroxycyclohex-2-en-1-one Chemical compound CCSC(C)CC1CC(O)=C(\C(CC)=N/OC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-SUJSHMTESA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 description 1
- XZNDHOKXYLEQQP-UHFFFAOYSA-N 3-tert-butyl-6-chloro-1-ethyl-2,4-dihydro-1,3,5-triazine-2,4-diamine Chemical compound CCN1C(N)N(C(C)(C)C)C(N)N=C1Cl XZNDHOKXYLEQQP-UHFFFAOYSA-N 0.000 description 1
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 1
- DYPNIXKYIWLADH-UHFFFAOYSA-N 6-chloro-1,3-diethyl-2,4-dihydro-1,3,5-triazine-2,4-diamine Chemical compound CCN1C(N)N=C(Cl)N(CC)C1N DYPNIXKYIWLADH-UHFFFAOYSA-N 0.000 description 1
- QZVGFTJJMWMFFV-UHFFFAOYSA-N 6-chloro-1-ethyl-3-propan-2-yl-2,4-dihydro-1,3,5-triazine-2,4-diamine Chemical compound CCN1C(N)N(C(C)C)C(N)N=C1Cl QZVGFTJJMWMFFV-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 241000209136 Agropyron Species 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 108020005544 Antisense RNA Proteins 0.000 description 1
- 235000003826 Artemisia Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000611157 Brachiaria Species 0.000 description 1
- 241001041979 Brachiaria plantaginea Species 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 239000005492 Carfentrazone-ethyl Substances 0.000 description 1
- 244000277285 Cassia obtusifolia Species 0.000 description 1
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 239000005497 Clethodim Substances 0.000 description 1
- 241001478752 Commelina benghalensis Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 239000005513 Fenoxaprop-P Substances 0.000 description 1
- 239000005530 Fluazifop-P Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000005565 Haloxyfop-P Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 240000007171 Imperata cylindrica Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 239000005575 MCPB Substances 0.000 description 1
- 101150039283 MCPB gene Proteins 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 239000005584 Metsulfuron-methyl Substances 0.000 description 1
- CGXBSUKYFNWHOJ-UHFFFAOYSA-N N-phenyl-1H-triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1N(C=C2N1C=CC=N2)S(=O)(=O)NC1=CC=CC=C1 CGXBSUKYFNWHOJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000745991 Phalaris Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005605 Pyraflufen-ethyl Substances 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 1
- 241000722118 Thlaspi Species 0.000 description 1
- 239000005627 Triclopyr Substances 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 244000030166 artemisia Species 0.000 description 1
- 235000009052 artemisia Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 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 description 1
- 239000003184 complementary RNA Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- GGWHBJGBERXSLL-UHFFFAOYSA-N cycloxydim Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 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 description 1
- 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 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000004136 fatty acid synthesis Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- YUVKUEAFAVKILW-SECBINFHSA-N fluazifop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-SECBINFHSA-N 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 102000005396 glutamine synthetase Human genes 0.000 description 1
- 108020002326 glutamine synthetase Proteins 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- GOCUAJYOYBLQRH-MRVPVSSYSA-N haloxyfop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-MRVPVSSYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- WQKNPQJFTFBHEA-UHFFFAOYSA-N methyl 5-chloro-3-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-2-methyl-1h-pyrazole-5-carboxylate Chemical compound COC(=O)C1(Cl)NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1 WQKNPQJFTFBHEA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- JKPCICKVMMLZHW-UHFFFAOYSA-N oxetan-2-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2OCC2)=N1 JKPCICKVMMLZHW-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 230000032361 posttranscriptional gene silencing Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 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 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical class C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Definitions
- the invention is in the field of the crop protection products which can be employed against harmful plants in tolerant or resistant crops of maize and which comprise, as herbicidally active substances, a combination of two or more herbicides.
- tolerant or resistant maize varieties and maize lines adds novel active substances which per se are not selective in conventional maize varieties, to the conventional weed control system.
- the active substances are, for example, the known broad-spectrum herbicides such as glyphosate, sulfosate, glufosinate, bialaphos and imidazolinone herbicides [herbicides (A)], which can now be employed in the tolerant crops developed specifically for them.
- the efficacy of these herbicides against harmful plants in the tolerant crops is high, but depends—similarly to other herbicide treatments—on the nature of the herbicide employed, its application rate, the preparation in question, the harmful plants to be controlled, the climatic conditions, the soil conditions etc. Furthermore, the herbicides exhibit weak points (zero effect) against specific species of harmful plants. Another criterion is the duration of action, or the degradation rate of the herbicide. If appropriate, 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 loss of action against individual plants can only be compensated for to some extent by higher application rates of the herbicides, if at all.
- a lower application rate not only reduces the amount of an active substance required for application, but as a rule, also reduces the amount of formulation auxiliaries required. Both reduce the economic outlay and improve the eco-friendliness of the herbicide treatment.
- One possibility for improving the use profile of a herbicide may consist in combining the active substance with one or more other active substances which contribute the desired additional properties.
- the combined use of a plurality of active substances does not infrequently lead to phenomena of a physical and biological incompatibility, for example lacking stability of a coformulation, decomposition of an active substance or antagonism of the active substances.
- what is desired are combinations of active substances with a favorable profile of action, high stability and as synergistic an increased action as possible, which allows the application rate to be reduced in comparison with the individual application of the active substances to be combined.
- the invention therefore relates to the use of herbicide combinations for controlling harmful plants in maize crops, wherein the herbicide combination in question has a synergistically active content of
- “Structurally different herbicides from the abovementioned group (A)” in group (B0) only include herbicides which are covered by the definition of group (A), but which are not component (A) in the combination in question.
- the synergistic effects are observed when the active substances (A) and (B) are applied together, but can also be observed upon split application (splitting).
- Another possibility is to apply the herbicides or herbicide combinations in several portions (sequential application), for example after pre-emergence applications, followed by post-emergence applications or after early postemergence applications, followed by applications at medium or late post-emergence.
- Preferred is the simultaneous application of the active substances of the combination in question, if appropriate in several portions.
- a staggered application of the individual active substances of a combination is also possible and may be advantageous in individual cases.
- Other crop protection agents such as fungicides, insecticides, acaricides and the like, and/or different auxiliaries, adjuvants and/or fertilizer applications may also be integrated into this system application.
- the synergistic effects allow the application rates of the individual active substances to be reduced, a more potent action against the same species of harmful plant combined with the same application rate, the control of species to which the action has hitherto not extended (zero effect), an extended application period and/or a reduced number of required individual applications and—as a result for the user—economical and ecologically more advantageous weed control systems.
- the combinations of (A)+(B) according to the invention allow synergistically increased effects which far and unexpectedly exceed the effects which can be achieved with the individual active substances (A) and (B).
- DE-A-2856260 has already disclosed a few herbicide combinations with glufosinate or L-glufosinate and other herbicides such as alloxidim, linuron, MCPA, 2,4-D, dicamba, triclopyr, 2,4,5-T, MCPB and others.
- Some herbicide combinations with glufosinate or glyphosate and other herbicides from the sulfonylurea series such as metsulfuron-methyl, nicosulfuron, primisulfuron, rimsulfuron and the like have already been disclosed in WO-A-92/083 53 and EP-A 0 252 237.
- herbicide combinations which can be employed particularly advantageously in tolerant maize crops are provided.
- Formula (A1) encompasses all stereoisomers and their mixtures, in particular the racemate and the particular enantiomer which has a biological action, for example L-glufosinate and its salts.
- active substances of the formula (A1) are the following:
- the abovementioned herbicides (A1.1) to (A1.5) are absorbed via the green parts of the plants and are known as broad-range herbicides or total herbicides; they are inhibitors of the enzyme glutamine synthetase in plants; see “The Pesticide Manual” 11th Edition, British Crop Protection Council 1997, pp. 643-645 and 120-121. While they can be employed post-emergence for controlling broad-leaved weeds and grass weeds in plantation crops and on non-crop area and, using specific application techniques, also for the in-between-rows treatment of agricultural ground crops such as maize, cotton and the like, the importance of use as selective herbicides in resistant transgenic crops of plants is increasing.
- Glufosinate is usually employed in the form of a salt, preferably of the ammonium salt.
- bialaphos sodium also termed bilanafos-sodium
- active substance (A1) for example an application rate in the range of 20 to 800, preferably 20 to 600
- grams of active substance of glufosinate per hectare g of a.s./ha or g of a.i./ha
- Similar amounts preferably amounts which have been converted into moles per hectare, also apply to glufosinate-ammonium and bialafos, or bialafos-sodium.
- the combinations with the foliar-acting herbicides (A1) are expediently employed in maize crops which are resistant or tolerant to the compounds (A1).
- Some tolerant maize crops which have been generated by genetic engineering, are already known and are employed in practice; cf. the article in the journal “Zuckerrübe” [Sugarbeet], year 47 (1998), p. 217 et seq.; for the generation of transgenic plants which are resistant to glufosinate, cf. EP-A-0242246, EP-A-242236, EP-A-257542, EP-A-275957, EP-A-0513054).
- the single dose is in the range of 0.5-5 kg of a.s./ha.
- Glyphosate is similar to glufosinate with regard to certain applications, but, in contrast to the latter, it is an inhibitor of the enzyme 5-enolpyruvylshikimate-3-phosphate synthase in plants; see “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 646-649.
- application rates in the range of 20 to 1000, preferably 20 to 800, g of a.s. glyphosate are, as a rule, required per ha.
- tolerant plants generated by genetic engineering are known for compounds (A2) and have been introduced into practice; cf. “Zuckerrübe” year 47 (1998), p. 217 et seq.; cf. also WO 92/00377, EP-A-115673, EP-A409815.
- imidazolinone herbicides are examples of imidazolinone herbicides (A3).
- the herbicides inhibit the enzyme acetolactate synthase (ALS) and thus the protein synthesis in plants; they are both soil-acting and foliar-acting and, in some cases, show selectivities in crops; cf. “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 697-699 for (A3.1), pp. 701-703 for (A3.2), pp. 694-696 for (A3.3) and (A3.4), pp. 696-697 for (A3.5), pp. 699-701 for (A3.6) and pp. 5 and 6, reviewed as AC 263,222 (for A3.7).
- the application rates of the herbicides are usually between 0.001 and 2 kg of a.s./ha. In the combinations according to the invention, they are in the range of 10 to 200 g of a.s./ha.
- EP-A-0360750 describes the generation of ALS-inhibitor-tolerant plants by selection methods or genetic engineering methods.
- the herbicide tolerance of the plants is generated by means of an elevated ALS content in the plants.
- U.S. Pat. No. 5,198,599 describes sulfonylurea- and imidazolinone-tolerant plants which have been obtained by selection methods.
- PPO inhibitors (A4) are:
- azoles are known as inhibitors of the enzyme protoporphyrinogen oxidase (PPO) in plants; see “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 1048-1049 for (A4.1), pp. 191-193 for (A4.2), pp. 904-905 for (A4.3) and pp. 1126-1127 for (A4.4). Tolerant crops of plants have already been described. As a rule, the application rates of the azoles are in the range of 5 to 200 g of a.s./ha.
- the herbicides inhibit mitosis and thus the fatty acid synthesis in plants; in particular, they are foliar-acting and, in some cases, they exhibit selectivities in crops.
- the application rates of the herbicides are usually between 0.2 and 1 kg of a.s./ha.
- they are in the range of 10 to 1000 g of a.s./ha.
- the combinations with cyclohexanediones are expediently employed in maize crops which are resistant to the cyclohexanediones. Such tolerant crops are already known.
- heteroarylphenoxyphenoxypropionic acid herbicides (A6) are:
- the herbizides (A6) are known as inhibitors of fatty acid biosynthesis and are usually employed at application rates of 5-500 g of a.s./ha.
- the application rate in the combinations according to the invention may be even lower in some cases, for example 1 to 300 g of a.s./ha.
- the combinations with the herbicides (A6) are expediently employed in maize crops which are tolerant to the herbicides; for example, in practice, this is also the case in those crops which are tolerant to cyclohexanedione herbicides (A5).
- Examples of suitable components (B) are compounds of subgroups (B1) to (B4):
- the specification of the herbicides by the common name of the acid is also intended to encompass the salts and esters, preferably the commercially available salts and esters, in particular the current commercial form of the active substance.
- the application rates of the herbicides (B) may vary greatly from herbicide to herbicide. The following ranges are rules of thumb:
- (B1.14) 50-1000, preferably 100-600, in particular 200-500,
- (B3.12) 1-150 preferably 5-100, in particular 5-80.
- ratios of compounds (A) and (B) can be deduced from the abovementioned application rates for the individual substances, for example the following ratios are of particular interest:
- the compounds (A) may be meaningful to combine one or more of the compounds (A) with more than one compound (B), preferably from amongst classes (B1), (B2) and (B3).
- combinations according to the invention can be employed together with other active substances, for example from the group of the safeners, fungicides, insecticides and plant growth regulators, or from the group of the additives and formulation auxiliaries conventionally used in crop protection.
- Additives are, for example, fertilizers and colors.
- Preferred active substances (C) are those which show a safener effect on the maize crop, specifically safeners which, in combination with the herbicides (B) reduce or avoid phythotoxic side-effects of the herbicides in maize plants.
- herbicidal compositions have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful-plants.
- the active substances 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 substances are applied before sowing, pre-emergence or post-emergence. Postemergence application, or early post-sowing pre-emergence application, is preferred.
- examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without the enumeration being a restriction to certain species.
- Examples of weed species on which the herbicidal compositions act efficiently are, from amongst the monocots, Echinochloa spp., Setaria spp., Digitaria spp., Brachiaria spp., Panicum spp., Agropyron spp., wild cereal forms and Sorghum spp., but also Avena spp., Alopecurus spp., and Cynodon spp, Lolium spp., Phalaris spp., Poa spp., and Cyperus species and Imperata.
- the spectrum of action extends to species such as, for example, Chenopodium spp., Amaranthus spp., Solanum spp., Datura spp., Abutilon spp., Ipomoea spp., Polygonum spp., Xanthium spp., Stellaria spp., Kochia spp.
- Chrysanthemum spp. Matricaria spp., Veronica spp., Anthemis spp., Thlaspi spp., Galium spp., Lamium spp., Pharbitis spp., Sida spp., Sinapis spp., Cupsella spp., Cirsium spp., Convolvulus spp., Rumex and Artemisia.
- the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely.
- the herbicidal compositions according to the invention are distinguished by a more rapidly commencing and longer lasting herbicidal action.
- the rainfastness of the active substances in the combinations according to the invention is advantageous.
- a particular advantage is that the dosages of the compounds (A) and (B), which are used in the combinations and are effective, can be adjusted to such a low quantity that their soil action is optimal. This does not only allow them to be employed in sensitive crops in the first place, but groundwater contaminations are virtually avoided.
- the active-substance-combination according to the invention allows the application rate of the active substances required to be reduced considerably.
- the tolerant, or cross-tolerant, maize plants are damaged only to a minor extent, or not at all.
- compositions according to the invention have outstanding growth-regulatory properties on the maize plants. They engage in the plants' metabolism in a regulatory manner and can thus be employed for provoking directed effects on plant constituents. Moreover, they are also suitable for the general control and inhibition of undesired vegetative growth without simultaneously destroying the plants. An inhibition of vegetative growth is very important in a large number of monocotyledonous and dicotyledonous crops since lodging can thus be reduced, or prevented completely.
- the compositions can be employed for controlling harmful plants in known tolerant or cross-tolerant maize crops, or in tolerant or genetically engineered maize crops still to be developed.
- the transgenic plants are distinguished by particular, advantageous properties, in addition to resistances to the compositions according to the invention, for example, by resistances to plant diseases or pathogens of plant diseases such as particular insects or microorganisms such as fungi, bacteria or viruses.
- Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents.
- transgenic plants are known whose oil content is increased or whose quality is altered, for example where the harvested material has a different fatty acid composition.
- novel plants with altered properties can be generated with the aid of genetic engineering methods (see, for example, EP-A0221044, EP-A-0131624). For example, the following were described in several cases:
- nucleic acid molecules which allow mutagenesis or sequence changes by recombination of DNA sequences can be introduced in plasmids.
- the abovementioned standard methods allow base changes to be carried out, subsequences to be removed, or natural or synthetic sequences to be added.
- adaptors or linkers may be added to the fragments.
- the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
- DNA molecules which encompass the entire encoding sequence of a gene product inclusive of any flanking sequences which may be present are also possible.
- the protein synthesized can be localized in any desired compartment of the plant cell.
- sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11(1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
- the transgenic plant cells can be regenerated by known techniques to give rise to whole plants.
- the transgenic plants can be plants of any desired plant species, i.e. not only monocotyledonous, but also dicotyledonous, plants.
- the invention therefore also relates to a method of controlling undesired vegetation in tolerant maize crops, which comprises applying one or more herbicides of the type (A) and one or more herbicides of the type (B) to the harmful plants, parts of these plants, or the area under cultivation.
- the invention also relates to the novel combinations of compounds (A)+(B) and to herbicidal compositions comprising them.
- the active substance combinations according to the invention can exist not only as formulation mixes of the two components, if appropriate together with other active substances, additives and/or conventional formulation auxiliaries, which are then applied in the customary manner after dilution with water, but also as so-called tank mixes by jointly diluting the separately formulated, or partially separately formulated, components with water.
- Compounds (A) and (B) or their combinations can be formulated in different ways, depending on the biological and/or chemico-physical parameters which prevail.
- WP wettable powders
- EC emulsifiable concentrates
- SL aqueous solutions
- EW emulsions
- sprayable solutions or emulsions such as oil-in-water and water-in-oil emulsion
- the formulation auxiliaries required such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ.
- combinations with other pesticidally active substances such as other herbicides, fungicides or insecticides, and with safeners, fertilizers and/or growth regulators, may also be prepared, for example in the form of a readymix or a tank mix.
- Wettable powders are products which are uniformly dispersible in water and which, besides the active substance, also comprise ionic or non-ionic surfactants (wetters, dispersants), for example polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutyinaphthalenesulfonate or else sodium oleoylmethyltauride, in addition to a diluent or inert material.
- ionic or non-ionic surfactants for example polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, sodium lignosulfon
- Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatic or hydrocarbons with addition of one or more ionic or non-ionic surfactants (emulsifiers).
- organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatic or hydrocarbons with addition of one or more ionic or non-ionic surfactants (emulsifiers).
- emulsifiers which may be used are: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzene sulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.
- alkylarylsulfonic acids such as calcium dodecylbenzene sulfonate
- nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan
- Dusts are obtained by grinding the active substance with finely divided solid materials, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomateous earth.
- finely divided solid materials for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomateous earth.
- Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carriers such as sand, kaolites or granulated inert material with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances may also be granulated in the manner conventionally used for the production of fertilizer granules, if desired in a mixture with fertilizers. As a rule, water-dispersible granules are prepared by processes such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed mixers and extrusion without solid inert material.
- the agrochemical preparations comprise 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active substances of the types A and/or B, the following concentrations being customary, depending on the type of formulation:
- the active substance concentration in wettable powders is, for example, approximately 10 to 95% by weight, the remainder to 100% by weight being composed of customary formulation constituents.
- the active substance concentration may amount to, for example, 5 to 80% by weight.
- Formulations in the form of dusts comprise, in most cases, 5 to 20% by weight of active substance, sprayable solutions approximately 0.2 to 25% by weight of active substance.
- the active substance content depends partly on whether the active compound is present in liquid or solid form and on which granulation auxiliaries and fillers are being used. As a rule, the content amounts to between 10 and 90% by weight in the case of the water-dispersible granules.
- the abovementioned active substance formulations may comprise, if appropriate, the conventional adhesives, wetters, dispersants, emulsifiers, preservatives, antifreeze agents, solvents, fillers, colors, carriers, antifoams, evaporation inhibitors, pH regulators or viscosity regulators.
- glufosinate-ammonium (A1.2) and of its L-enantiomer can be improved by surfactants, preferably by wetters from the series of the alkyl polyglycol ether sulfates which contain, for example, 10 to 18 carbon atoms and which are used in the form of their alkali metal salts or ammonium salts, but also as the magnesium salt, such as sodium C 12 /C 14 -fatty alcohol diglycol ether sulfate (®Genapol LRO, Hoechst); see EP-A-0476555, EP-A-0048436, EP-A-0336151 or U.S. Pat. No. 4,400,196 and Proc. EWRS Symp.
- surfactants preferably by wetters from the series of the alkyl polyglycol ether sulfates which contain, for example, 10 to 18 carbon atoms and which are used in the form of their alkali metal salts or ammonium salts, but also as the magnesium salt, such as
- alkyl polyglycol ether sulfates are also suitable as penetrants and synergists for a series of other herbicides, inter alia also herbicides from the series of the imidazolinones; see EP-A-0502014.
- the formulations which are present in commercially available form, are optionally diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules.
- Preparations in the form of dusts, soil granules, granules for broadcasting and sprayable solutions are usually not diluted further prior to use with other inert substances.
- the active substances can be applied to the plants, parts of the plants, seeds of the plants or the area under cultivation (soil of a field), preferably to the green plants and parts of the plants and, if appropriate, additionally to the soil of the field.
- One possible use is the joint application of the active substances in the form of tank mixes, the concentrated formulations of the individual active substances, in optimal formulations, jointly being mixed with water in the tank and the resulting spray mixture being applied.
- a joint herbicidal formulation of the combination according to the invention of the active substances (A) and (B) has the advantage of being easier to apply since the quantities of the components are already presented in the correct ratio to each other. Moreover, the adjuvants in the formulation can be matched optimally to each other, while a tank mix of different formulations may lead to undesired combinations of adjuvants.
- compositions according to the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and dicotyledonous weeds.
- A, B denote the effect of the active substances A, or in %, for a or b g of a.s./ha; E denotes the expected value in % for a+b g a.s./ha.
- compositions according to the invention which are formulated as wettable powders or as emulsion concentrates are sprayed in various dosages on the green parts of the plants at an application rate of 600 to 800 l of water/ha (converted). After the test plants have remained in the greenhouse for about 3 to 4 weeks under optimal growth conditions, the effect of the products is scored visually by comparison with untreated controls. When applied post-emergence, too, the compositions according to the invention have a good herbicidal activity against a broad spectrum of economically important grass weeds and broad-leaved weeds.
- Transgenic maize plants with a resistance to one or more herbicides (A) together with typical weed plants were grown in the open on 2 ⁇ 5 m plots under natural field conditions; alternatively, weed infestation occurred naturally when the maize plants were grown.
- the treatment with the compositions according to the invention and, as control, separately by only applying the active substances of the components, was carried out under standard conditions with a plot sprayer at an application rate of 200-300 liters of water per hectare in parallel tests as can be seen from the scheme in Table 1, i.e. pre-sowing pre-emergence, post-sowing preemergence or post-emergence in the early, medium or late stage.
- Herbicidal effect in field trials with maize Dose 1) Herbicidal action 2) (%) Active in g of against substance(s) a.s./ha Mais LL
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
- The invention is in the field of the crop protection products which can be employed against harmful plants in tolerant or resistant crops of maize and which comprise, as herbicidally active substances, a combination of two or more herbicides.
- The introduction of tolerant or resistant maize varieties and maize lines, in particular transgenic maize varieties and maize lines, adds novel active substances which per se are not selective in conventional maize varieties, to the conventional weed control system. The active substances are, for example, the known broad-spectrum herbicides such as glyphosate, sulfosate, glufosinate, bialaphos and imidazolinone herbicides [herbicides (A)], which can now be employed in the tolerant crops developed specifically for them. The efficacy of these herbicides against harmful plants in the tolerant crops is high, but depends—similarly to other herbicide treatments—on the nature of the herbicide employed, its application rate, the preparation in question, the harmful plants to be controlled, the climatic conditions, the soil conditions etc. Furthermore, the herbicides exhibit weak points (zero effect) against specific species of harmful plants. Another criterion is the duration of action, or the degradation rate of the herbicide. If appropriate, 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 loss of action against individual plants can only be compensated for to some extent by higher application rates of the herbicides, if at all. Moreover, there is always a demand for methods to achieve the herbicidal effect with lower application rates of active substances. A lower application rate not only reduces the amount of an active substance required for application, but as a rule, also reduces the amount of formulation auxiliaries required. Both reduce the economic outlay and improve the eco-friendliness of the herbicide treatment.
- One possibility for improving the use profile of a herbicide may consist in combining the active substance with one or more other active substances which contribute the desired additional properties. However, the combined use of a plurality of active substances does not infrequently lead to phenomena of a physical and biological incompatibility, for example lacking stability of a coformulation, decomposition of an active substance or antagonism of the active substances. In contrast, what is desired are combinations of active substances with a favorable profile of action, high stability and as synergistic an increased action as possible, which allows the application rate to be reduced in comparison with the individual application of the active substances to be combined.
- Surprisingly, it has now been found that active substances from the group of the abovementioned broad-spectrum herbicides (A) in combination with other herbicides from group (A) and, if appropriate, specific herbicides (B) interact especially favorably when they are employed in the maize crops which are suitable for the selective use of the first-mentioned herbicides.
- The invention therefore relates to the use of herbicide combinations for controlling harmful plants in maize crops, wherein the herbicide combination in question has a synergistically active content of
- (A) a broad-spectrum herbicide from the group of the compounds consisting of
- (A1) compounds of the formula (A1),
- in which Z is a radical of the formula —OH or a peptide radical of the formula —NHCH(CH3)CONHCH(CH3)COOH or
- —NHCH(CH3)CONHCH[CH2CH(CH3)2]COOH, and their esters and salts, preferably glufosinate and its salts with acids and bases, in particular glufosinate-ammonium, L-glufosinate or its salts, bialaphos and its salts with acids and bases, and other phosphinothricin derivatives,
- (A2) compounds of the formula (A2) and their esters and salts,
- preferably glyphosate and its alkali metal salts or salts with amines, in particular glyphosate-isopropylammonium, and sulfosates,
- (A3) imidazolinones, preferably imazethapyr, imazapyr, imazamethabenz, imazamethabenz-methyl, imazaquin, imazamox, imazapic (AC 263,222) and their salts and
- (A4) herbicidal azoles from the protoporphyrinogen-oxidase inhibitors (PPO inhibitors), such as WC9717 (=CGA276854),
- (A5) cyclohexanedione herbicides and, if appropriate, also
- (A6) heteroaryloxyphenoxypropionic acid herbicides, and
- (A1) compounds of the formula (A1),
- (B) one or more herbicides from the group of the compounds which consists of
- (B0) one or more structurally different herbicides from the abovementioned group (A) and/or
- (B1) foliar- and soil-acting herbicides which are effective against monocotyledonous and dicotyledonous harmful plants, and/or
- (B2) herbicides which can be employed selectively in maize against dicots, and/or
- (B3) foliar- and soil-active herbicides which can be employed selectively in maize, predominantly against dicotyledonous harmful plants,
and the maize crops are tolerant to the herbicides (A) and (B) which form a constituent of the combination, if appropriate in the presence of safeners.
- “Structurally different herbicides from the abovementioned group (A)” in group (B0) only include herbicides which are covered by the definition of group (A), but which are not component (A) in the combination in question.
- In addition to the herbicide combinations according to the invention, other crop protection active substances and adjuvants and formulation auxiliaries conventionally used in crop protection may be used.
- The synergistic effects are observed when the active substances (A) and (B) are applied together, but can also be observed upon split application (splitting). Another possibility is to apply the herbicides or herbicide combinations in several portions (sequential application), for example after pre-emergence applications, followed by post-emergence applications or after early postemergence applications, followed by applications at medium or late post-emergence. Preferred is the simultaneous application of the active substances of the combination in question, if appropriate in several portions. However, a staggered application of the individual active substances of a combination is also possible and may be advantageous in individual cases. Other crop protection agents such as fungicides, insecticides, acaricides and the like, and/or different auxiliaries, adjuvants and/or fertilizer applications may also be integrated into this system application.
- The synergistic effects allow the application rates of the individual active substances to be reduced, a more potent action against the same species of harmful plant combined with the same application rate, the control of species to which the action has hitherto not extended (zero effect), an extended application period and/or a reduced number of required individual applications and—as a result for the user—economical and ecologically more advantageous weed control systems.
- For example, the combinations of (A)+(B) according to the invention allow synergistically increased effects which far and unexpectedly exceed the effects which can be achieved with the individual active substances (A) and (B).
- WO-A-98/09525 has already described a method of controlling weeds in transgenic crops which are resistant to phosphorus-containing herbicides such as glufosinate or glyphosate, herbicide combinations being employed which comprise glufosinate or glyphosate and at least one herbicide from the group consisting of prosulfuron, primisulfuron, dicamba, pyridate, dimethenamid, metolachlor, flumeturon, propaquizafop, atrazine, clodinafop, norflurazone, ametryn, terbuthylazine, simazine, prometryn, NOA-402989 (3-phenyl-4-hydroxy-6-chloropyridazine), a compound of the formula
in which R=4-chloro-2-fluoro-5-(methoxycarbonylmethylthio)phenyl (disclosed in U.S. Pat. No. 4,671,819), CGA276854=1-allyloxycarbonyl-1-methylethyl 2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoate (=WC9717, disclosed in U.S. Pat. No. 5,183,492) and 4-oxetanyl 2{N-[N-(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate (disclosed in EP-A-496701). Details on the obtainable effects, or effects which have been obtained, cannot be found in the publication WO-A-98/09525. There are no examples on synergistic effects or on carrying out the method in specific crops, nor are there specific combinations of two, three or more herbicides. - DE-A-2856260 has already disclosed a few herbicide combinations with glufosinate or L-glufosinate and other herbicides such as alloxidim, linuron, MCPA, 2,4-D, dicamba, triclopyr, 2,4,5-T, MCPB and others.
- Some herbicide combinations with glufosinate or glyphosate and other herbicides from the sulfonylurea series such as metsulfuron-methyl, nicosulfuron, primisulfuron, rimsulfuron and the like have already been disclosed in WO-A-92/083 53 and EP-A 0 252 237.
- However, the use of the combinations for controlling harmful plants has been shown in the publications only with reference to a few plants species or else with reference to no example.
- In our experiments, it has been found, surprisingly, that there exist large differences between the usefulness of the herbicide combinations mentioned in WO-A-98/09525 and in the other references and also of other novel herbicide combinations in crops of plants.
- According to the invention, herbicide combinations which can be employed particularly advantageously in tolerant maize crops are provided.
- The compounds of the formulae (A1) to (A5) are known or can be prepared analogously to known processes.
- Formula (A1) encompasses all stereoisomers and their mixtures, in particular the racemate and the particular enantiomer which has a biological action, for example L-glufosinate and its salts. Examples of active substances of the formula (A1) are the following:
- (A1.1) glufosinate in the narrow sense, i.e. D,L-2-amino-4-[hydroxy(methyl)phosphinyl]butanoic acid,
- (A1.2) glufosinate-monoammonium salt,
- (A1.3) L-glufosinate, L- or (2S)-2-amino-4-[hydroxy(methyl)phosphinyl]butanoic acid (=phosphinothricin),
- (A1.4) L-glufosinate monoammonium salt,
- (A1.5) bialaphos (or bilanafos), i.e. L-2-amino-4-[hydroxy-(methyl)phosphinyl]butanoyl-L-alanyl-L-alanine, in particular its sodium salt.
- The abovementioned herbicides (A1.1) to (A1.5) are absorbed via the green parts of the plants and are known as broad-range herbicides or total herbicides; they are inhibitors of the enzyme glutamine synthetase in plants; see “The Pesticide Manual” 11th Edition, British Crop Protection Council 1997, pp. 643-645 and 120-121. While they can be employed post-emergence for controlling broad-leaved weeds and grass weeds in plantation crops and on non-crop area and, using specific application techniques, also for the in-between-rows treatment of agricultural ground crops such as maize, cotton and the like, the importance of use as selective herbicides in resistant transgenic crops of plants is increasing.
- Glufosinate is usually employed in the form of a salt, preferably of the ammonium salt. The racemate of glufosinate, or glufosinate-ammonium, alone is usually applied at rates between 200 and 2000 g of a.s./ha (=g of a.i./ha=grams of active substance per hectare). At such rates, glufosinate is effective mainly when taken up via the green parts of the plants. However, since it is degraded microbially in the soil within a few days, it has no long-term action in the soil. The same also applies to the related active substance bialaphos sodium (also termed bilanafos-sodium); see “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 120-121. As a rule, markedly less active substance (A1), for example an application rate in the range of 20 to 800, preferably 20 to 600, grams of active substance of glufosinate per hectare (g of a.s./ha or g of a.i./ha) is required in the combinations according to the invention. Similar amounts, preferably amounts which have been converted into moles per hectare, also apply to glufosinate-ammonium and bialafos, or bialafos-sodium.
- The combinations with the foliar-acting herbicides (A1) are expediently employed in maize crops which are resistant or tolerant to the compounds (A1). Some tolerant maize crops which have been generated by genetic engineering, are already known and are employed in practice; cf. the article in the journal “Zuckerrübe” [Sugarbeet], year 47 (1998), p. 217 et seq.; for the generation of transgenic plants which are resistant to glufosinate, cf. EP-A-0242246, EP-A-242236, EP-A-257542, EP-A-275957, EP-A-0513054).
- Examples of compounds (A2) are
- (A2.1) glyphosate, i.e. N-(phosphonomethyl)glycine,
- (A2.2) glyphosate-monoisopropylammonium salt,
- (A2.3) glyphosate-sodium salt,
- (A2.4) sulfosate, i.e. N-(phosphonomethyl)glycine-trimesium salt=N-(phosphonomethyl)glycine-trimethylsulfoxonium salt.
- Glyphosate is usually employed in the form of a salt, preferably of the monoisopropylammonium salt or the trimethylsulfoxonium salt (=trimesium salt=sulfosate). Based on the free acid glyphosate, the single dose is in the range of 0.5-5 kg of a.s./ha. Glyphosate is similar to glufosinate with regard to certain applications, but, in contrast to the latter, it is an inhibitor of the enzyme 5-enolpyruvylshikimate-3-phosphate synthase in plants; see “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 646-649. In the combinations according to the invention, application rates in the range of 20 to 1000, preferably 20 to 800, g of a.s. glyphosate are, as a rule, required per ha.
- Also, tolerant plants generated by genetic engineering are known for compounds (A2) and have been introduced into practice; cf. “Zuckerrübe” year 47 (1998), p. 217 et seq.; cf. also WO 92/00377, EP-A-115673, EP-A409815.
- Examples of imidazolinone herbicides (A3) are
- (A3.1) imazapyr and its salts and esters,
- (A3.2) imazethapyr and its salts and esters,
- (A3.3) imazamethabenz and its salts and esters,
- (A3.4) imazamethabenz-methyl,
- (A3.5) imazamox and its salts and esters,
- (A3.6) imazaquin and its salts and esters, for example the ammonium salt,
- (A3.7) imazapic (AC 263,222) and its salts and esters, for example the ammonium salt.
- The herbicides inhibit the enzyme acetolactate synthase (ALS) and thus the protein synthesis in plants; they are both soil-acting and foliar-acting and, in some cases, show selectivities in crops; cf. “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 697-699 for (A3.1), pp. 701-703 for (A3.2), pp. 694-696 for (A3.3) and (A3.4), pp. 696-697 for (A3.5), pp. 699-701 for (A3.6) and pp. 5 and 6, reviewed as AC 263,222 (for A3.7). The application rates of the herbicides are usually between 0.001 and 2 kg of a.s./ha. In the combinations according to the invention, they are in the range of 10 to 200 g of a.s./ha.
- The combinations with imidazolinones are expediently employed in maize crops which are resistant to the imidazolinones. Such tolerant crops are already known. EP-A-0360750, for example, describes the generation of ALS-inhibitor-tolerant plants by selection methods or genetic engineering methods. The herbicide tolerance of the plants is generated by means of an elevated ALS content in the plants. U.S. Pat. No. 5,198,599 describes sulfonylurea- and imidazolinone-tolerant plants which have been obtained by selection methods.
- Examples of PPO inhibitors (A4) are:
- (A4.1) pyraflufen and its esters, such as pyraflufen-ethyl,
- (A4.2) carfentrazone and its esters, such as carfentrazone-ethyl,
- (A4.3) oxadiargyl
- (A4.4) sulfentrazone
- (A4.5) WC9717 or CGA276854=1-allyloxycarbonyl-1-methylethyl 2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoate (disclosed in U.S. Pat. No. 5,183,492).
- The abovementioned azoles are known as inhibitors of the enzyme protoporphyrinogen oxidase (PPO) in plants; see “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 pp. 1048-1049 for (A4.1), pp. 191-193 for (A4.2), pp. 904-905 for (A4.3) and pp. 1126-1127 for (A4.4). Tolerant crops of plants have already been described. As a rule, the application rates of the azoles are in the range of 5 to 200 g of a.s./ha.
- Some plants which are tolerant to PPO inhibitors are already known.
- Examples of cyclohexanedione herbicides (A5) are:
- (A5.1) sethoxydim (“The Pesticide Manual” 11th Ed., British Crop Protection Council 1997 (termed “PM” hereinbelow, pp 1101-1103), i.e. (E,Z)-2-(1-ethoxyiminobutyl)-5-[2-(ethylthio)propyl]-3-hydroxycyclohex-2-enone,
- (A5.2) cycloxydim (PM, pp. 290-291), i.e. 2-(1-ethoxyiminobutyl)-3-hydroxy-5-thian-3-ylcyclohex-2-enone,
- (A5.3) clethodim (PM, pp. 250-251), i.e. 2{(E)1-[(E)-3-chloroallyloxyimino]propyl}5-[-2(ethylthio)-propyl]-3-hydroxycyclohex-2-enone,
- (A5.4) “clefoxidim” or “BAS 625H” (see AG Chem New Compound Review, Vol. 17, 1999, pp. 26, edited by AGRANOVA) (=2-[1-2-(4-chlorophenoxy)propoxyimino)butyl]-3-oxo-5-thion-3-yl-cyclohex-1-enol),
- (A5.5) tralkoxidim (PM, pp. 1211-1212), i.e. 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-enone.
- The herbicides inhibit mitosis and thus the fatty acid synthesis in plants; in particular, they are foliar-acting and, in some cases, they exhibit selectivities in crops. The application rates of the herbicides are usually between 0.2 and 1 kg of a.s./ha. In the combinations according to the invention, they are in the range of 10 to 1000 g of a.s./ha. The combinations with cyclohexanediones are expediently employed in maize crops which are resistant to the cyclohexanediones. Such tolerant crops are already known.
- Examples of heteroarylphenoxyphenoxypropionic acid herbicides (A6) are:
- (A6.1) “fenoxaprop-P” and its esters, such as the ethyl ester “fenoxaprop-P-ethyl” (see PM, pp. 519-520) (=(R)-2-[4-(6-chlorobenzoxyzolyl-2-yloxy)-phenoxy]propionic acid and its ethyl ester), also in the use form of the racemate ufenoxapropn and its esters, such as the ethyl ester, and/or
- (A6.2) “quizalofop-P” and its esters, such as the ethyl or tefuryl ester (see PM, pp. 1089-1092) (=(R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionic acid or its ethyl ester or its tetrahydrofurfuryl ester), also in the form of the racemate “quizalofop” and its esters; cf. also as the specific ester “propaquizafop” (compound A6.3) and/or
- (A6.3) “propaquizafop” (PM, pp. 1021-1022), the 2-isopropylideneamino-oxyethyl ester of quizalofop-P, and/or
- (A6.4) “fluazifop-P” and its esters, such as the butyl ester (see PM, pp. 556-557) (=(R)-2-[4-(5-trifluoromethylpyrid-2-yloxy)-phenoxy]propionic acid or its butyl ester), also in the use form of the racemate “fluazifop” and its ester, and/or
- (A6.5) “haloxyfop-P” and its esters, such as the methyl ester (see PM, pp. 660-663) (=(R)-2-[4-(3-chloro-5-trifluoromethylpyrid-2-yl-oxy)phenoxy]propionic acid or its methyl ester), also in the use form of the racemate “haloxyfop” and its esters, such as the methyl or the etotyl ester and/or
- (A6.6) “cyhalofop” and its esters, such as the butyl ester (PM, pp. 297-298) (=(R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionic acid or its butyl ester and/or
- (A6.7) “clodinafop” and its esters, such as the propargyl ester (PM, pp. 251-252) (=(R)-2-[4-(5-chloro-3-fluoropyrid-2-yloxy)phenoxy]propionic acid or its propargyl ester).
- The herbizides (A6) are known as inhibitors of fatty acid biosynthesis and are usually employed at application rates of 5-500 g of a.s./ha. The application rate in the combinations according to the invention may be even lower in some cases, for example 1 to 300 g of a.s./ha. The combinations with the herbicides (A6) are expediently employed in maize crops which are tolerant to the herbicides; for example, in practice, this is also the case in those crops which are tolerant to cyclohexanedione herbicides (A5).
- Examples of suitable components (B) are compounds of subgroups (B1) to (B4):
- (B1) Herbicides which are not only foliar-acting, but also soil-acting, and which can be employed selectively in maize against grasses and dicots, for example the following compounds (of which the common name and the reference in “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997, abbreviated to “PM”), is given:
- (B1.1) cyanazine (PM, pp. 280-283), i.e. 2-(4-chloro-6-ethylamino-1,3,5-triazin-2-ylamino)-2-methylpropionitrile,
- (B1.2) atrazine (PM, pp. 55-57), i.e. N-ethyl-N′-isopropyl-6-chloro-2,4-diamino-1,3,5-triazine,
- (B1.3) terbuthylazine (PM, pp. 1168-1170), i.e. N-ethyl-N′-tert-butyl-6-chloro-2,4-diamino-1,3,5-triazine,
- (B1.4) acetochlor (PM, pp. 10-12), i.e. 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide,
- (B1.5) metolachlor (PM, pp. 833-834), i.e. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)-acetamide,
- (B1.6) alachlor (PM, pp. 23-24), i.e. 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide,
- (B1.7) terbutryn (PM, pp. 1170-1172), i.e. N-(1,1-dimethylethyl)-N′-ethyl-6-methylthio-2,4-diamino-1,3,5-triazine,
- (B1.8) benoxacor (PM, pp. 102-103), i.e. 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine,
- (B1.9) nicosulfuron (PM, pp. 877-879), i.e. 2-(4,6-dimethoxypyrimidin-2-yl)-3-(3-dimethylcarbamoyl-2-pyridylsulfonyl)urea,
- (B1.10) rimsulfuron (PM, pp. 1095-1097), i.e. 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pyridylsulfonyl)-urea,
- (B1.11) primisulfuron and its esters, such as the methyl ester (PM, pp. 997-999), i.e. 2-[4,6-bis(difluoromethoxy)pyrimidin-2-ylcarbamoylsulfamoyl]benzoic acid or its methyl ester,
- (B1.12) dimethenamid (PM, pp. 409-410), i.e. 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide,
- (B1.13) fluthiamide (BAY FOE 5043, flufenacet) (PM, pp. 82-83), i.e. 4′-fluoro-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetanilide,
- (B1.14) sulcotrione (PM, pp. 1124-1125), i.e. 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione,
- (B1.15) simazin (PM, pp. 1106-1108), i.e. 6-chloro-N,N′-diethyl-2,4-diamino-1,3,5-triazine,
- (B1.16) mesotrione, i.e. 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (ZA1296, cf. Weed Science Society of America (WSSA) in WSSA Abstracts 1999, Vol. 39, pages 65-66, numbers 130-132),
- (B1.17) penthoxamid, i.e. 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)acetamide (TKC-94, known from AG Chem New Compound, Review Vol. 17 (1999), EP-A-206 251),
and, if active substances from group (B1) are present as racemic mixtures, preferably also the particular active compounds in the form of the pure or enriched active isomer,
- (B2) herbicides which can be employed selectively in maize against dicots, for example the compounds
- (B2.1) pendimethalin (PM, pp. 937-939), i.e. N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine,
- (B2.2) pyridate (PM, pp. 1064-1066), i.e. 6-chloro-3-phenylpyridazin-4-yl S-octyl thiocarbonate,
- (B2.3) iodosulfuron (proposed common name) and, preferably, the methyl ester (cf. WO 96/41537), i.e. 4-iodo-2-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)benzoic acid or the methyl ester, disclosed in WO-A-92/13845,
- (B2.4) metosulam (PM, pp. 836-495), i.e. 2′,6′-dichloro-5,7-dimethoxy-3′-methyl-[1,2,4]triazolo[1,5a]pyrimidine-2-sulfonanilide,
- (B2.5) isoxaflutole (PM, pp. 737-739), i.e. (5-cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]-methanone,
- (B2.6) metribuzin (PM, pp. 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one,
- (B2.7) cloransulam and, preferably, the methyl ester (PM, p. 165), i.e. 3-chloro-2-(5-ethoxy-7-fluoro-[1,2,4]triazolo-[1,5-6]pyrimidin-2-ylsulfonamido)benzoic acid or its methyl ester,
- (B2.8) flumetsulam (PM, pp. 573-574), i.e. 2′,6′-dichloro-5-methyl-[1,2,4]triazolo[1,5a]pyrimidine-2-sulfonanilide and
- (B2.9) linuron (PM, pp. 751-753), i.e. 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea and
- (B2.10) florasulam, i.e. N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-1,2,4-triazolo[1,5C]-pyrimidine-2-sulfonamide (DE-570, cf. Zeitschrift Pfl. Krankh. PflSchutz, Special Issue XVI, 527-534 81998),
- (B2.11) isoxachlortole, i.e. (4-chloro-2-(methylsulfonyl)phenyl) 5-cyclopropyl-4-isoxazolyl ketone, EP-A-470856)
and, if abovementioned active substances from group (B2) exist as racemic mixtures, preferably also the particular active substance in the form of the pure or enriched effective isomer,
- (B3) herbicides which are foliar-acting and soil-acting and which can be employed selectively in maize, predominantly against dicotyledonous harmful plants, for example the compounds:
- (B3.1) bromoxynil (PM, pp. 149-151), i.e. 3,5-dibromo-4-hydroxybenzonitrile,
- (B3.2) dicamba (PM, pp. 356-357), i.e. 3,6-dichloro-o-anisic acid and its salts,
- (B3.3) 2,4-D (PM, pp. 323-327), i.e. 2,4-dichlorophenoxyacetic acid and its salts and esters,
- (B3.4) clopyralid (PM, pp. 260-263), i.e. 3,6-dichloro-2-pyridinecarboxylic acid and its salts and esters,
- (B3.5) prosulfuron (PM, pp. 1041-1043), i.e. 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea,
- (B3.6) thifensulfuron and its esters, preferably the methyl ester (PM, pp. 1188-1190), i.e. 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylic acid or its methyl ester,
- (B3.7) carfentrazone and its salts and esters, preferably the ethyl ester (PM, pp. 191-193), i.e. 2-chloro-3-[2-chloro-5-(difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)4-fluorophenyl]propionic acid and its ethyl ester,
- where combinations with compound (A4.2) according to the definition do not constitute herbicide combinations of different herbicide active substances A and B and are therefore excepted,
- (B3.8) Lab271272 (=tritosulfuron, CAS Reg. No. 142469-14-5; see AG Chem New Compound Review, Vol. 17, 1999, p. 24, edited by AGRANOVA), i.e. N-[[[4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl)amino]-carbonyl]-2-(trifluoromethyl)benzenesulfonamide), and
- (B3.9) MCPA (PM, pp. 767-769), i.e. (4-chloro-2-methylphenoxy)acetic acid, and its salts and esters,
- (B3.10) halosulfuron and its esters, such as the methyl ester (PM, p. 657-659), i.e. methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazolecarboxylate, also in its salt form,
- (B3.11) diflufenzopyr (BASF 654 00H) (PM, pp. 81-82), i.e. 2-{1-[4-(3,5-difluorophenyl)semi-carbazone]ethyl}nicotinic acid, and its salts,
- (B3.12) sulfosulfuron (PM, pp. 1130-1131), i.e. 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]-pyridin-3-ylsulfonyl)urea
- and, if abovementioned active substances from group (B3) exist as racemic mixtures, preferably also the particular active compound in the form of the pure or enriched effective isomer.
- In the case of active substances based on carboxylic acids or other active substances which form salts or esters, the specification of the herbicides by the common name of the acid is also intended to encompass the salts and esters, preferably the commercially available salts and esters, in particular the current commercial form of the active substance.
- The application rates of the herbicides (B) may vary greatly from herbicide to herbicide. The following ranges are rules of thumb:
- Compounds (B0): 1-3000 g a.s./ha, preferably 5-2000 g a.s./ha (cf. the information on the group of the compounds (A)),
- Compounds (B1): 0.1-5000 g a.s./ha, preferably 1-5000 g a.s./ha,
- Compounds (B2): 0.1-5000 g a.s./ha, preferably 1-3000 g a.s./ha
- Compounds (B3): 0.5-5000 g a.s./ha, preferably 1-3000 g a.s./ha
- The following specific application rates are preferred (in g of a.s./ha):
- (B1.1) to (B1.8) 100-5000 g, preferably 200-4000, in particular 300-3500,
- (B1.9) to (B1.11) 0.1-120, preferably 1-90,
- (B1.12) 50-5000, preferably 1004000, in particular 300-3500,
- (B1.13) 100-2000, preferably 200-1500, in particular 300-1200,
- (B1.14) 50-1000, preferably 100-600, in particular 200-500,
- (B1.15) 100-5000, preferably 200-4000, in particular 300-3500,
- (B1.16) 10-500, preferably 25-300, in particular 50-200,
- (B1.17) 5-1500, preferably 10-1000, in particular 20-800,
- (B2.1) 100-3000, preferably 200-2500, in particular 300-2000,
- (B2.2) 100-2500, preferably 200-2000, in particular 300-1500,
- (B2.3) 0.1-100, preferably 0.2-20, in particular 0.5-15,
- (B2.4) 1-200, preferably 5-150, in particular 10-100,
- (B2.5) 5-300, preferably 10-200, in particular 20-150,
- (B2.6) 10-1500, preferably 25-1000, in particular 50-800,
- (B2.7) 2-200, preferably 2.5-100, in particular 5-80,
- (B2.8) 5-500, preferably 10-300, in particular 20-200,
- (B2.9) 50-2500, preferably 100-2000, in particular 200-1000,
- (B2.10) 0.5-100, preferably 1-20, in particular 3-15,
- (B2.11) 5-300, preferably 10-200, in particular 20-150,
- (B3.1) 50-1000, preferably 100-600, in particular 200-500,
- (B3.2) 5-2500, preferably 10-2000, in particular 200-1500,
- (B3.3) 50-3000, preferably 100-2000, in particular 200-1500,
- (B3.4) 10-300, preferably 20-250, in particular 40-200,
- (B3.5) 1-100, preferably 2-70, in particular 5-50,
- (B3.6) 0.5-100, preferably 1-50, in particular 240,
- (B3.7) 1-250, preferably 5-120, in particular 10-100,
- (B3.8) 1-200, preferably 5-150, in particular 10-120,
- (B3.9) 50-3000, preferably 100-2000, in particular 200-1500,
- (B3.10) 1-200, preferably 5-150, in particular 10-50,
- (B3.11) 5-1000, preferably 10-500, in particular 20-80,
- (B3.12) 1-150, preferably 5-100, in particular 5-80.
- The ratios of compounds (A) and (B) can be deduced from the abovementioned application rates for the individual substances, for example the following ratios are of particular interest:
- (A):(B) in the range of 18,000:1 to 1:5000, preferably 2000:1 to 1:1000, in particular 200:1 to 1:100,
- (A):(B0) in the range of 1000:1 to 1:400, preferably 400:1 to 1:400, in particular 200:1 to 1:200,
- (A1):(B1) in the range of 1500:1 to 1:300, preferably 400:1 to 1:250, in particular 200:1 to 1:100,
- (A1):(B2) in the range of 10,000:1 to 1:300, preferably 1500:1 to 1:250, in particular 1000:1 to 1:100, particularly preferably 200:1 to 1:100,
- (A1):(B3) in the range of 2000:1 to 1:300, preferably 1500:1 to 1:250, in particular 200:1 to 1:100,
- (A2):(B1) in the range of 2500:1 to 1:100, preferably 2000:1 to 1:50, in particular 300:1 to 1:20,
- (A2):(B2) in the range of 18,000:1 to 1:100, preferably 2000:1 to 1:50, in particular 300:1 to 1:20,
- (A2):(B3) in the range of 3000:1 to 1:100, preferably 2000:1 to 1:50, in particular 300:1 to 1:20,
- (A3):(B1) in the range of 1000:1 to 1:1000, preferably 200:1 to 1:500, in particular 100:1 to 1:200,
- (A3):(B2) in the range of 5000:1 to 1:1000, preferably 800:1 to 1:500, in particular 200:1 to 1:500, particularly preferably 100:1 to 1:200,
- (A3):(B3) in the range of 500:1 to 1:800, preferably 200:1 to 1:500, in particular 100:1 to 1:200,
- (A4):(B1) in the range of 1000:1 to 1:5000, preferably 200:1 to 1:1000, in particular 100:1 to 1:250,
- (A4):(B2) in the range of 10,000:1 to 1:5000, preferably 2000:1 to 1:1000, in particular 1000:1 to 1:400, in particular 500:1 to 1:250,
- (A4):(B3) in the range of 1000:1 to 1:2000, preferably 200:1 to 1:1000, in particular 100:1 to 1:250,
- (A5):(B1) in the range of 1500:1 to 1:1000, preferably 1000:1 to 1:500, in particular 200:1 to 1:100,
- (A5):(B2) in the range of 10,000:1 to 1:2000, preferably 1000:1 to 1:500, in particular 200:1 to 1:100,
- (A5):(B3) in the range of 1500:1 to 1:1000, preferably 1000:1 to 1:500, in particular 200:1 to 1:100,
- (A6):(B1) in the range of 2000:1 to 1:2000, preferably 1000:1 to 1:1000, in particular 200:1 to 1:200,
- (A6):(B2) in the range of 5000:1 to 1:2000, preferably 2000:1 to 1:1000, in particular 200:1 to 1:100,
- (A6):(B3) in the range of 1000:1 to 1:1000, preferably 500:1 to 1:500, in particular 100:1 to 1:100.
- The use of the following combinations is of particular interest:
- (A1.1)+(B1.1), (A1.1)+(B1.2), (A1.1)+(B1.3), (A1.1)+(B1.4), (A1.1)+(B1.5), (A1.1)+(B1.6), (A1.1)+(B1.7), (A1.1)+(B1.8), (A1.1)+(B1.9), (A1.1)+(B1.10), (A1.1)+(B1.11), (A1.1)+(B1.12), (A1.1)+(B1.13), (A1.1)+(B1.14), (A1.1)+(B1.15), (A1.1)+(B1.16), (A1.1)+(B.17),
- (A1.2)+(B1.1), (A1.2)+(B1.2), (A1.2)+(B1.3), (A1.2)+(B1.4), (A1.2)+(B1.5), (A1.2)+(B1.6), (A1.2)+(B1.7), (A1.2)+(B1.8), (A1.2)+(B1.9), (A1.2)+(B1.10), (A1.2)+(B1.11), (A1.2)+(B1.12), (A1.2)+(B1.13), (A1.2)+(B1.14), (A1.2)+(B.1.15), (A1.2)+(B.1.16), (A1.2)+(B1.17),
- (A1.1)+(B2.1), (A1.1)+(B2.2), (A1.1)+(B2.3), (A1.1)+(B2.4), (A1.1)+(B2.5), (A1.1)+(B2.6), (A1.1)+(B2.7), (A1.1)+(B2.8), (A1.1)+(B2.9), (A1.1)+(B2.10), (A1.1)+(B2.11),
- (A1.2)+(B2.1), (A1.2)+(B2.2), (A1.2)+(B2.3), (A1.2)+(B2.4), (A1.2)+(B2.5), (A1.2)+(B2.6), (A1.2)+(B2.7), (A1.2)+(B2.8), (A1.2)+(B2.9),
- (A.1.2)+(B2.10), (A1.2)+(B2.11),
- (A1.1)+(B3.1), (A1.1)+(B3.2), (A1.1)+(B3.3), (A11.1)+(B3.4), (A1.1)+(B3.5), (A1.1)+(B3.6), (A1.1)+(B3.7), (A1.1)+(B3.8), (A1.1)+(B3.9), (A1.1)+(B3.10), (A1.1)+(B3.11), (A1.1)+(B3.12), (A1.1)+(B3.13),
- (A1.2)+(B3.1), (A1.2)+(B3.2), (A1.2)+(B3.3), (A1.2)+(B3.4), (A1.2)+(B3.5), (A1.2)+(B3.6), (A1.2)+(B3.7), (A1.2)+(B3.8), (A1.2)+(B3.9), (A.1.2)+(B3.10), (A1.2)+(B3.11), (A1.2)+(B3.12), (A1.2)+(B3.13),
- (A2.2)+(B1.1), (A2.2)+(B1.2), (A2.2)+(B1.3), (A2.2)+(B1.4), (A2.2)+(B1.5), (A2.2)+(B1.6), (A2.2)+(B1.7), (A2.2)+(B1.8), (A2.2)+(B1.9), (A2.2)+(B1.10), (A2.2)+(B1.11), (A2.2)+(B1.12), (A2.2)+(B1.13), (A2.2)+(B1.14), (A2.2)+(B1.15), (A2.2)+(B1.16), (A2.2)+(B1.17),
- (A2.2)+(B2.1), (A2.2)+(B2.2), (A2.2)+(B2.3), (A2.2)+(B2.4), (A2.2)+(B2.5), (A2.2)+(B2.6), (A2.2)+(B2.7), (A2.2)+(B2.8), (A2.2)+(B2.9), (A2.2)+(B2.10), (A2.2)+(B2.11),
- (A2.2)+(B3.1), (A2.2)+(B3.2), (A2.2)+(B3.3), (A2.2)+(B3.4), (A2.2)+(B3.5), (A2.2)+(B3.5), (A2.2)+(B3.6), (A2.2)+(B3.7), (A2.2)+(B3.8), (A2.2)+(B3.9), (A2.2)+(B3.10), (A2.2)+(B3.11), (A2.2)+(B3.12), (A2.2)+(B3.13).
- In the case of the combination of a compound (A) with one or more compounds (B0), this is, according to the definition, a combination of two or more compounds from group (A). Because of the broad-spectrum herbicides (A), the condition for such a combination is that the transgenic plants or mutants show cross-resistance to various herbicides (A). Such cross-resistances in transgenic plants have already been disclosed; cf. WO-A-98/20144.
- In individual cases, it may be meaningful to combine one or more of the compounds (A) with more than one compound (B), preferably from amongst classes (B1), (B2) and (B3).
- Moreover, the combinations according to the invention can be employed together with other active substances, for example from the group of the safeners, fungicides, insecticides and plant growth regulators, or from the group of the additives and formulation auxiliaries conventionally used in crop protection.
- Additives are, for example, fertilizers and colors.
- Preferred are herbicide combinations of one or more compounds (A) with one or more compounds from the group (B1) or (B2) or (B3).
- Also preferred are combinations of one or more compounds (A), for example (A1.2)+(A2.2), preferably of a compound (A), with one or more compounds (B) as shown in the scheme:
- (A)+(B1)+(B2), (A)+(B1)+(B3), (A)+(B2)+(B3).
- Combinations to which one or more other active substances of a different structure [active substances (C)] are added are also according to the invention, for example
- (A)+(B1)+(C), (A)+(B2)+(C) or (A)+(B3)+(C),
- (A)+(B1)+(B2)+(C) or (A)+(B1)+(B3)+(C) or (A)+(B2)+(B3)+(C).
- The preferred conditions illustrated hereinbelow also apply to combinations of the last-mentioned type with three or more active substances, in particular to two-way-combinations according to the invention, mainly when they contain the two-way-combinations according to the invention. Preferred active substances (C) are those which show a safener effect on the maize crop, specifically safeners which, in combination with the herbicides (B) reduce or avoid phythotoxic side-effects of the herbicides in maize plants.
- The use according to the invention of the combinations with one or more herbicides from the group (A), preferably (A1.2) or (A2.2), in particular (A1.2), and with one or more herbicides, preferably one herbicide, from the group mentioned hereinbelow is also of particular interest:
- (B1′) cyanazine, acetochlor, alachlor, terbutryn, benoxacor, fluthiamide, sulcotrione, mesotrione and penthoxamid or
- (B2′) pendimethalin, iodosulfuron, metosulam, isoxaflutole, metribuzin, cloransulam, flumetsulam and also florasulam and isoxachlortole or
- (B3′) bromoxynil, clopyralid, carfentrazone and Lab271272 and also halosulfuron, diflufenzopyr and sulfosulfuron, or
- herbicides of more than one of groups (B1′) to (B3′).
- Preferred are the combinations of the particular component (A) with one or more herbicides of group (B1′), (B2′) or (B3′).
- Also preferred are the combinations (A)+(B1′)+(B2′), (A)+(B1′)+(B3′) or (A)+(B2′)+(B3′).
- The combinations according to the invention (=herbicidal compositions) have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful-plants. The active substances 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 substances are applied before sowing, pre-emergence or post-emergence. Postemergence application, or early post-sowing pre-emergence application, is preferred.
- Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without the enumeration being a restriction to certain species. Examples of weed species on which the herbicidal compositions act efficiently are, from amongst the monocots, Echinochloa spp., Setaria spp., Digitaria spp., Brachiaria spp., Panicum spp., Agropyron spp., wild cereal forms and Sorghum spp., but also Avena spp., Alopecurus spp., and Cynodon spp, Lolium spp., Phalaris spp., Poa spp., and Cyperus species and Imperata.
- In the case of the dicotyledonous weed species, the spectrum of action extends to species such as, for example, Chenopodium spp., Amaranthus spp., Solanum spp., Datura spp., Abutilon spp., Ipomoea spp., Polygonum spp., Xanthium spp., Stellaria spp., Kochia spp. and Viola spp., but also Chrysanthemum spp., Matricaria spp., Veronica spp., Anthemis spp., Thlaspi spp., Galium spp., Lamium spp., Pharbitis spp., Sida spp., Sinapis spp., Cupsella spp., Cirsium spp., Convolvulus spp., Rumex and Artemisia.
- If the compounds according to the invention 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 substances 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 crop plants, is eliminated at a very early point in time and in a sustained manner.
- In comparison with the individual preparations, the herbicidal compositions according to the invention are distinguished by a more rapidly commencing and longer lasting herbicidal action. As a rule, the rainfastness of the active substances in the combinations according to the invention is advantageous. A particular advantage is that the dosages of the compounds (A) and (B), which are used in the combinations and are effective, can be adjusted to such a low quantity that their soil action is optimal. This does not only allow them to be employed in sensitive crops in the first place, but groundwater contaminations are virtually avoided. The active-substance-combination according to the invention allows the application rate of the active substances required to be reduced considerably.
- When herbicides of the type (A)+(B) 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 grass weeds 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 abovementioned properties and advantages are necessary under practical weed control conditions to keep agricultural crops 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 compounds according to the invention have an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, the tolerant, or cross-tolerant, maize plants are damaged only to a minor extent, or not at all.
- Moreover, some of the compositions according to the invention have outstanding growth-regulatory properties on the maize plants. They engage in the plants' metabolism in a regulatory manner and can thus be employed for provoking directed effects on plant constituents. Moreover, they are also suitable for the general control and inhibition of undesired vegetative growth without simultaneously destroying the plants. An inhibition of vegetative growth is very important in a large number of monocotyledonous and dicotyledonous crops since lodging can thus be reduced, or prevented completely.
- Owing to their herbicidal and plant-growth-regulatory properties, the compositions can be employed for controlling harmful plants in known tolerant or cross-tolerant maize crops, or in tolerant or genetically engineered maize crops still to be developed. As a rule, the transgenic plants are distinguished by particular, advantageous properties, in addition to resistances to the compositions according to the invention, for example, by resistances to plant diseases or pathogens of plant diseases such as particular insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants are known whose oil content is increased or whose quality is altered, for example where the harvested material has a different fatty acid composition.
- Conventional methods of generating novel plants which have modified properties in comparison to plants occurring to date consist, for example, in traditional breeding methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of genetic engineering methods (see, for example, EP-A0221044, EP-A-0131624). For example, the following were described in several cases:
-
- the modification, by genetic engineering, of crop plants with the aim of modifying the starch synthesized in the plant (for example WO 92/11376, WO 92/14827, WO 91/19806),
- transgenic crop plants which exhibit resistances to other herbicides, for example to sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659),
- transgenic crop plants with the capability of producing Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259),
- transgenic crop plants with a modified fatty acid composition (WO 91/13972).
A large number of techniques in molecular biology with the aid of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim 2nd Edition 1996 or Christou, “Trends in Plant Science” 1(1996) 423-431.
- To carry out such genetic engineering manipulations, nucleic acid molecules which allow mutagenesis or sequence changes by recombination of DNA sequences can be introduced in plasmids. For example, the abovementioned standard methods allow base changes to be carried out, subsequences to be removed, or natural or synthetic sequences to be added. To connect the DNA fragments to each other, adaptors or linkers may be added to the fragments.
- For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
- To this end, it is possible to use, on the one hand, DNA molecules which encompass the entire encoding sequence of a gene product inclusive of any flanking sequences which may be present, as well as DNA molecules which only encompass portions of the encoding sequence, it being necessary for these portions to be long enough to have an antisense effect on the cells. The use of DNA sequences which have a high degree of homology to the encoding sequences of a gene product, but are not completely identical to them, is also possible.
- When expressing nucleic acid molecules in plants, the protein synthesized can be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to link the encoding region with DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11(1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
- The transgenic plant cells can be regenerated by known techniques to give rise to whole plants. In principle, the transgenic plants can be plants of any desired plant species, i.e. not only monocotyledonous, but also dicotyledonous, plants.
- Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or the expression of heterologous (=foreign) genes or gene sequences.
- The invention therefore also relates to a method of controlling undesired vegetation in tolerant maize crops, which comprises applying one or more herbicides of the type (A) and one or more herbicides of the type (B) to the harmful plants, parts of these plants, or the area under cultivation.
- The invention also relates to the novel combinations of compounds (A)+(B) and to herbicidal compositions comprising them.
- The active substance combinations according to the invention can exist not only as formulation mixes of the two components, if appropriate together with other active substances, additives and/or conventional formulation auxiliaries, which are then applied in the customary manner after dilution with water, but also as so-called tank mixes by jointly diluting the separately formulated, or partially separately formulated, components with water.
- Compounds (A) and (B) or their combinations can be formulated in different ways, depending on the biological and/or chemico-physical parameters which prevail. The following are examples of general possibilities for formulations: wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, oil- or water-based dispersions, suspoemulsions, dusts (DP), seed-dressing materials, granules for soil application or for broadcasting, or water dispersible granules (WG), ULV formulations, microcapsules or waxes.
- The individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler “Chemische Technologie” [Chemical engineering], Volume 7, C. Hauser Verlag Munich, 4th Edition, 1986; van Valkenburg, “Pesticide Formulations”, Marcel Dekker N.Y., 1973; K. Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd. London.
- The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridegewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, “Grenzflachenaktive Athylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuchler, “Chemische Technologie”, Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.
- Based on these formulations, combinations with other pesticidally active substances, such as other herbicides, fungicides or insecticides, and with safeners, fertilizers and/or growth regulators, may also be prepared, for example in the form of a readymix or a tank mix.
- Wettable powders (sprayable powders) are products which are uniformly dispersible in water and which, besides the active substance, also comprise ionic or non-ionic surfactants (wetters, dispersants), for example polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutyinaphthalenesulfonate or else sodium oleoylmethyltauride, in addition to a diluent or inert material.
- Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatic or hydrocarbons with addition of one or more ionic or non-ionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzene sulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.
- Dusts are obtained by grinding the active substance with finely divided solid materials, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomateous earth.
- Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carriers such as sand, kaolites or granulated inert material with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances may also be granulated in the manner conventionally used for the production of fertilizer granules, if desired in a mixture with fertilizers. As a rule, water-dispersible granules are prepared by processes such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed mixers and extrusion without solid inert material.
- As a rule, the agrochemical preparations comprise 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active substances of the types A and/or B, the following concentrations being customary, depending on the type of formulation: The active substance concentration in wettable powders is, for example, approximately 10 to 95% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration may amount to, for example, 5 to 80% by weight.
- Formulations in the form of dusts comprise, in most cases, 5 to 20% by weight of active substance, sprayable solutions approximately 0.2 to 25% by weight of active substance.
- In the case of granules such as dispersible granules, the active substance content depends partly on whether the active compound is present in liquid or solid form and on which granulation auxiliaries and fillers are being used. As a rule, the content amounts to between 10 and 90% by weight in the case of the water-dispersible granules.
- In addition, the abovementioned active substance formulations may comprise, if appropriate, the conventional adhesives, wetters, dispersants, emulsifiers, preservatives, antifreeze agents, solvents, fillers, colors, carriers, antifoams, evaporation inhibitors, pH regulators or viscosity regulators.
- For example, it is known that the effect of glufosinate-ammonium (A1.2) and of its L-enantiomer can be improved by surfactants, preferably by wetters from the series of the alkyl polyglycol ether sulfates which contain, for example, 10 to 18 carbon atoms and which are used in the form of their alkali metal salts or ammonium salts, but also as the magnesium salt, such as sodium C12/C14-fatty alcohol diglycol ether sulfate (®Genapol LRO, Hoechst); see EP-A-0476555, EP-A-0048436, EP-A-0336151 or U.S. Pat. No. 4,400,196 and Proc. EWRS Symp. “Factors Affecting Herbicidal Activity and Selectivity”, 227-232 (1988). Moreover, it is known that alkyl polyglycol ether sulfates are also suitable as penetrants and synergists for a series of other herbicides, inter alia also herbicides from the series of the imidazolinones; see EP-A-0502014.
- For use, the formulations, which are present in commercially available form, are optionally diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for broadcasting and sprayable solutions are usually not diluted further prior to use with other inert substances.
- The active substances can be applied to the plants, parts of the plants, seeds of the plants or the area under cultivation (soil of a field), preferably to the green plants and parts of the plants and, if appropriate, additionally to the soil of the field.
- One possible use is the joint application of the active substances in the form of tank mixes, the concentrated formulations of the individual active substances, in optimal formulations, jointly being mixed with water in the tank and the resulting spray mixture being applied.
- A joint herbicidal formulation of the combination according to the invention of the active substances (A) and (B) has the advantage of being easier to apply since the quantities of the components are already presented in the correct ratio to each other. Moreover, the adjuvants in the formulation can be matched optimally to each other, while a tank mix of different formulations may lead to undesired combinations of adjuvants.
-
- a) A dust is obtained by mixing 10 parts by weight of an active substance/active substance mixture and 90 parts by weight of talc as inert material and comminuting the mixture in a hammer mill.
- b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of an active substance/active substance mixture, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetter and dispersant, and grinding the mixture in a pinned-disk mill.
- c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active substance/active substance mixture with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approx. 255 to 277° C.), and grinding the mixture in a ball mill to a fineness of below 5 microns.
- d) An emulsifiable concentrate is obtained from 15 parts by weight of an active substance/active substance mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.
- e) Water-dispersible granules are obtained by mixing
- 75 parts by weight of an active substance/active substance mixture,
- 10 parts by weight of calcium lignosulfonate,
- 5 parts by weight of sodium lauryl sulfate,
- 3 parts by weight of polyvinyl alcohol and
- 7 parts by weight of kaolin,
- grinding the mixture on a pinned-disk mill and granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- f) Water-dispersible granules are also obtained by homogenizing and precomminuting, on a colloid mill,
- 25 parts by weight of an active substance/active substance mixture,
- 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
- 2 parts by weight of sodium oleoylmethyltaurinate,
- 1 part by weight of polyvinyl alcohol,
- 17 parts by weight of calcium carbonate and
- 50 parts by weight of water,
- subsequently grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a single-substance model.
- 1. Pre-Emergence Effect on Weeds
- Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants are placed in sandy loam soil in plastic pots and covered with soil. The compositions which are formulated in the form of concentrated aqueous solutions, wettable powders or emulsion concentrates are then applied to the surface of the soil cover in the form of an aqueous solution, suspension or emulsion at an application rate of 600 to 800 of l water/ha (converted), in various dosages. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the weeds. After the test plants have emerged, the damage to the plants or the negative effect on the emergence is scored visually after a test period of 3 to 4 weeks by comparison with untreated controls. As shown by the test results, the compositions according to the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and dicotyledonous weeds.
- Frequently, effects of the combinations according to the invention are observed which exceed the formal total of the effects when applying the herbicides individually (=synergistic effect).
- If the data of the effects observed already exceed the formal total of the data of the experiments with individual applications, then they also exceed Colby's expected value, which is calculated by the formula which follows and which is also considered to be suggestive of synergism (cf. S. R. Colby; in Weeds 15 (1967) pp. 20 to 22):
E=A+B−(A·B/100) - A, B denote the effect of the active substances A, or in %, for a or b g of a.s./ha; E denotes the expected value in % for a+b g a.s./ha.
- At suitable low dosages, the observed data of the experiments show an effect of the combinations above Colby's expected values.
- 2. Post-Emergence Effect on Weeds
- Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy loam soil in cardboard pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants in the three-leaf stage are treated with the compositions according to the invention. The compositions according to the invention which are formulated as wettable powders or as emulsion concentrates are sprayed in various dosages on the green parts of the plants at an application rate of 600 to 800 l of water/ha (converted). After the test plants have remained in the greenhouse for about 3 to 4 weeks under optimal growth conditions, the effect of the products is scored visually by comparison with untreated controls. When applied post-emergence, too, the compositions according to the invention have a good herbicidal activity against a broad spectrum of economically important grass weeds and broad-leaved weeds.
- Frequently, effects of the combinations according to the invention are observed which exceed the formal total of the effects when applying the herbicides individually.
- At suitable low dosages, the observed data of the experiments show an effect of the combinations above Colby's expected values.
- (cf. score figures in Example 1).
- 3. Herbicidal Effect and Tolerance by Crop Plants (Field Trial)
- Transgenic maize plants with a resistance to one or more herbicides (A) together with typical weed plants were grown in the open on 2×5 m plots under natural field conditions; alternatively, weed infestation occurred naturally when the maize plants were grown. The treatment with the compositions according to the invention and, as control, separately by only applying the active substances of the components, was carried out under standard conditions with a plot sprayer at an application rate of 200-300 liters of water per hectare in parallel tests as can be seen from the scheme in Table 1, i.e. pre-sowing pre-emergence, post-sowing preemergence or post-emergence in the early, medium or late stage.
TABLE 1 Use scheme - examples Application Pre- of emergence Post- Post- Post- the active Pre- post- emergence emergence emergence substances sowing sowing 1-2-leaf 2-4-leaf 6-leaf combination (A) + (B) ″ (A) + (B) ″ (A) + (B) ″ (A) + (B) ″ (A) + (B) sequential (A) (B) ″ (A) (B) ″ (A) (B) ″ (A) (A) (B) ″ (A) (B) (B) ″ (A) (A) + (B) ″ (B) (A) ″ (B) (A) + (B) ″ (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) (A) + (B) ″ (A) + (B) (A) + (B) - 2, 4, 6 and 8 weeks after the application, the herbicidal activity of the active substances or active substance mixtures was scored visually with reference to the treated plots in comparison to untreated control plots. The damage to, and the development of, all aerial parts of the plants was recorded. Scoring was done on the basis of a percentage sale (100% action=all plants destroyed; 50% action=50% of the plants and green parts of the plants destroyed; 0% action=no recognizable effect=like control plot. The mean of the score values of in each case 4 plots was calculated.
- The comparison demonstrated that the herbicidal effect of the combinations according to the invention was usually higher, in some cases considerably higher, than the total of the effects of the individual herbicides (=EA). In essential periods of the period of scoring, the effects were greater than Colby's expected values (=EC) (cf. scoring in Example 1) and therefore suggest a synergism. In contrast, the maize plants were not damaged owing to the treatments with the herbicidal compositions, or were only damaged to a negligible extent.
- Other test results are compiled in the tables which follow.
- Abbreviations generally used in the tables:
- g of a.s./ha=gram of active substance (100% active substance) per hectare
- EA=Total of the herbicidal effects of the individual applications
- EC=Colby's expected value (cf. scoring in Table 1)
- “Mais LL”=®Liberty-Link-Mais, maize which is tolerant or resistant to glufosinate-ammonium,
TABLE 2 Herbicidal effect in field trials with maize Damage Herbicidal action2) Dose1) to (%) against Active in g of Mais LL3) Digitaria Panicum substance(s) a.s./ha in % sanguinalis dichotomiflorum (A1.2) 200 2 0 8 400 4 15 50 600 3 30 92 (B3.2) 300 0 88 0 (A1.2) + 200 + 300 3 94 75 (B3.2) (EA = 88) (EA = 8) 400 + 300 4 100 92 (EC = 89) (EA = 50)
Abbreviations for Table 2:
1)= Application in the 5-6-leaf stage
2)= Scoring 11 days after application
3)= ® Liberty-Link-Mais = maize which is resistant to glufosinate-ammonium,
(A1.2) = glufosinate-ammonium
(B3.2) = dicamba
-
TABLE 3 Herbicidal effect in field trials with maize Dose1) Active in g of Herbicidal action2) (%) against Damage to substance(s) a.s./ha AGRRE SETVI AMARE Mais LL in % (A1.2) 200 0 72 65 3 300 0 72 84 2 400 11 69 82 5 600 15 69 87 3 1000 74 74 85 4 (B1.2) 1500 26 53 3 0 (A1.2) + (B1.2) 200 + 1500 32 95 (EC = 89) 87 (EA = 68) 3 400 + 1500 68 97 (EC = 75) 88 (EA = 85) 4
Abbreviations for Table 3:
1)= Application in the 2-4-leaf stage
2)= Scoring 3 weeks after application
(A1.2) = glufosinate-ammonium
(B1.2) = atrazine
-
TABLE 4 Herbicidal effect in field trials with maize Dose1) Herbicidal action2) Damage Active in g of (%) against to Mais LL substance(s) a.s./ha EPHHL in % (A1.2) 600 55 0 300 45 0 (B1.16) 50 60 0 100 58 0 150 70 0 (A1.2) + (B1.16) 300 + 50 83 10 (EC = 78) 300 + 100 95 10 (EC = 77)
Abbreviations for Table 4:
1)= Application in the 4-leaf stage
2)= Scoring 6 weeks after application
(A1.2)= glufosinate-ammonium
(B1.16) = mesotrione
EPHHL = Euphorbia heterophylla
-
TABLE 5 Herbicidal effect in field trials with maize Dose1) Damage Herbicidal action2) Active in g of to Mais (%) against substance(s) a.s./ha LL in % Euphorbia heterophylla (A1.2) 400 0 60 200 0 50 100 0 37 (B1.14) 400 0 75 300 0 68 200 0 60 (A1.2) + (B1.14) 100 + 200 0 99 (EA = 97) 400 + 200 0 99 (EC = 84)
Abbreviations for Table 5:
1)= Application in the 6-leaf stage
2)= Scoring 44 days after application
(A1.2) = glufosinate-ammonium
(A1.14) = sulcotrione
-
TABLE 6 Herbicidal effect in field trials with maize Herbicidal action1) Dose1) (%) against Active in g of Fagopyron Lolium substance(s) a.s./ha esculentum multiflorum (A1.2) 500 55 78 330 20 15 200 10 0 (B2.3) 2.5 85 84 (A1.2) + (B2.3) 330 + 2.5 93 90 (EC = 88) (EC = 87)
Abbreviations for Table 6:
1)= Application in the 2- to 4-leaf stage
2)= Scoring 26 days after application
(A1.2) = glufosinate-ammonium
(B2.3) = iodosulfuron-methyl.
-
TABLE 7 Herbicidal effect in field trials with maize Herbicidal action2) Dose1) (%) against Active in g of Avena Portulaca substance(s) a.s./ha fatua oleracea (A1.2) 450 50 50 300 48 43 (B1.5) 1680 40 35 (A1.2) + (B1.5) 300 + 1680 98 (EA = 88) 95 (EA = 78) (B1.1) 2242 35 45 (A1.2) + (B1.1) 300 + 2242 86 (EA = 83) 93 (EA = 88) (B3.1) 360 10 25 (A1.2) + (B3.1) 300 + 360 63 (EA = 58) 65 (EA = 60)
Abbreviations for Table 7:
1)= Application in the 2- to 4-leaf stage
2)= Scoring 28 days after application
(A1.2) = glufosinate-ammonium
(B1.5) = metolachlor
(B3.1) = bromoxynil
-
TABLE 8 Herbicidal effect in field trials with maize Active Dose1) Herbicidal action2) (%) against substance(s) in g of a.s./ha Sorghum halepense (A1.2) 500 53 300 15 (B1.11) 20 93 10 62 (A1.2) + (B1.11) 300 + 10 78 (EA = 77)
Abbreviations for Table 8:
1)= Application in the 4-leaf stage
2)= Scoring 28 days after application
(A1.2) = glufosinate-ammonium
(B1.11) = primisulfuron-methyl
-
TABLE 9 Herbicidal effect in field trials with maize Dose1) Herbicidal action2) Active in g of (%) against substance(s) a.s./ha Cassia obtusifolia (A1.2) 400 60 (B2.1) 925 0 (A1.1) + (B2.1) 400 + 925 88 (EA = 60)
Abbreviations for Table 9:
1)= Application in the 3-leaf stage
2)= Scoring 21 days after application
(A1.2) = glufosinate-ammonium
(B2.1) = pendimethalin
-
TABLE 10 Herbicidal effect in field trials with maize Active Dose1) Herbicidal action2) (%) against substance(s) in g of a.s./ha Brachiaria plantaginea (A1.2) 600 70 300 45 150 5 (B1.5) 1500 70 (1.2) + (B1.5) 150 + 1500 95 (EA = 75)
Abbreviations for Table 10:
1)= Application in the 2-leaf stage
2)= Scoring 28 days after application
(A1.2) = glufosinate-ammonium
(B1.5) = metolachlor
-
TABLE 11 Herbicidal effect in field trials with maize Dose1) Herbicidal action2) (%) Active in g of against substance(s) a.s./ha Mais LL Commelina benghalensis (A1.2) 600 0 82 300 0 63 200 0 60.0 100 0 43 (A3.2) 100 0 73 (A1.2) + (A3.2)3) 100 + 100 0 92 (EA = 86) (B1.6) 1920 0 37 (A1.2) + (B1.6) 100 + 1920 0 83 (EA = 80)
Abbreviations for Table 11:
1)= Application in the 3-leaf stage
2)= Scoring 42 days after application
3)= Second active substance applied 10 days after the first active substance
(A1.2) = glufosinate-ammonium
(A3.2) = imazethapyr
(B1.6) = alachlor
-
TABLE 12 Herbicidal effect in field trials with maize Active Dose1) Herbicidal action2) (%) against substance(s) in g of a.s./ha Portulaca oleracea (A1.2) 500 60 250 35 (B3.1) 360 25 (A1.2) + (B3.1) 250 + 360 65 (EA = 60)
Abbreviations for Table 12:
1)= Application in the 6-leaf stage
2)= Scoring 26 days after application
(A1.2)= glufosinate-ammonium
(B3.1)= bromoxynil
-
TABLE 13 Herbicidal effect in field trials with maize Herbicidal action2) Active Dose1) (%) against substance(s) in g of a.s./ha Sinapis arvensis (A1.2) 350 75 230 45 (B3.6) 15 73 (A1.2) + (B3.6) 230 + 15 99 (EC = 85)
Abbreviations for Table 13:
1)= Application in the 4-to 5-leaf stage
2)= Scoring 28 days after application
(A1.2) = glufosinate-ammonium
(B3.6) = thifensulfuron-methyl
-
TABLE 14 Herbicidal effect in field trials with maize Dose1) Herbicidal action2) (%) Active in g of against substance(s) a.s./ha Mais LL Echinochloa crus-galli (A1.2) 400 8 68 200 0 35 (B2.8) 70 8 65 50 5 40 (A1.2) + (B2.8) 200 + 50 6 85 (EA = 75) (B3.4) 100 0 15 (A1.2) + (B3.4) 200 + 100 1 65 (EA = 50)
Abbreviations for Table 14:
1)= Application in the 3-leaf stage
2)= Scoring 21 days after application
(A1.2) = glufosinate-ammonium
(B3.4) = clopyralid
(B2.8) = flumetsulam
-
TABLE 15 Herbicidal effect in field trials with maize Herbicidal action2) Dose1) (%) against Active in g of Galium Fagopyrum substance(s) a.s/ha aparine esculentum (A1.2) 500 65 55 250 45 20 125 30 10 (B3.8) 60 85 78 30 65 60 15 45 30 (A1.2) + (B3.8) 250 + 15 85 (EC = 72) 65 (EA = 50) 125 + 30 83 (EC = 75) 75 (EA = 70)
Abbreviations for Table 15:
1)= Application in the 3-to 4-leaf stage
2)= Scoring 24 days after application
(A1.2) = glufosinate-ammonium
(B3.6) = tritosulfuron
-
TABLE 16 Herbicidal effect in field trials with maize Active Dose Herbicidal action3) (%) against substance(s) in g of a.s./ha Sorghum bicolor (B2.5)1) 100 75 50 40 25 20 (A1.2)2) 500 85 250 50 125 30 (B2.5)1) + (A1.2)2) 50 + 250 95 (EA = 90) 25 + 250 80 (EA = 70)
Abbreviations for Table 16:
1)= Pre-emergence application
2)= Application in the 4-leaf stage 18 days after the pre-emergence application of1)
3)= Scoring 46 days after pre-emergence application, or 28 days after post-emergence application
(B2.5) = isoxaflutole
(A1.2) = glufosinate-ammonium
-
TABLE 17 Herbicidal effect in field trials with maize Active Dose1) Herbicidal action2) (%) against substance(s) in g of a.s./ha Echinochloa crus-galli (A1.2) 500 74 250 45 125 25 (B1.13) 500 55 250 30 125 25 (A1.2) + (B1.13) 250 + 125 85 (EA = 55) 500 + 125 100 (EA = 98) 125 + 500 93 (EA = 80)
Abbreviations for Table 17:
1)= Application in the 3-leaf stage
2)= Scoring 28 days after application
(A1.2) = glufosinate-ammonium
(B1.13) = fluthiamide
-
TABLE 18 Herbicidal effect in field trials with maize Active Dose1) Herbicidal action2) (%) against substance(s) in g of a.s./ha Echinochloa crus-galli (A1.2) 500 78 250 65 125 45 (B1.4) 1500 45 750 40 375 10 (A1.2) + (B1.4) 125 + 750 93 (EA = 85) 125 + 1500 97 (EA = 90) 500 + 375 92 (EA = 88)
Abbreviations for Table 18:
1)= Application in the 3- to 4-leaf stage
2)= Scoring 42 days after application
(A1.2) = glufosinate-ammonium
(B1.4) = acetochlor
-
TABLE 19 Herbicidal effect in field trials with maize Active Dose1) Herbicidal action2) (%) against substance(s)0 in g of a.s./ha Lamium amplexicaule (A2.1) 600 90 400 75 (B2.3) 2.5 55 (A2.1) + (B2.3) 400 + 2.5 93 (EC = 88)
Abbreviations for Table 19:
1)= Application in the 1-leaf stage
2)= Scoring 17 days after application
(A1.2) = glyphosate-isopropylammonium
(B2.3) = iodosulfuron-methyl
-
TABLE 20 Herbicidal effect in field trials with maize Dose1) Active in g of Herbicidal action2) (%) against substance(s) a.s./ha Convolvulus arvensis (A1.2) 400 20 200 0 (B3.3) 500 20 (A1.2) + (B3.3) 400 + 500 50 (EA = 40) (B3.9) 500 60 (A1.2) + (B3.9) 200 + 500 75 (EA = 60) (B2.2) 900 40 (A1.2) + (B2.2) 200 + 900 73 (EA = 40) (B1.12) 900 30 (A1.2) + (B1.12) 200 + 900 65 (EA = 30)
Abbreviations for Table 20:
1)= Application in the 3- to 4-leaf stage
2)= Scoring 28 days after application
(A1.2) = glyphosate-isopropylammonium
(B3.3) = 2,4-D
(B3.9) = MCPA
(B2.2) = pyridate
(B1.12) = dimethenamide
Claims (21)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/323,085 US20060111240A1 (en) | 1998-08-13 | 2005-12-30 | Herbicidal compositions for tolerant or resistant maize crops |
US13/108,522 US8772199B2 (en) | 1998-08-13 | 2011-05-16 | Herbicidal compositions for tolerant or resistant maize crops |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19836737.6 | 1998-08-13 | ||
DE19836737A DE19836737A1 (en) | 1998-08-13 | 1998-08-13 | Use of a synergistic herbicide combination including a glufosinate- or glyphosate-type, imidazolinone, protoporphyrinogen oxidase inhibitory azole or cyclohexanedione herbicide to control weeds in maize |
DE19919993.0 | 1999-04-30 | ||
DE1999119993 DE19919993A1 (en) | 1999-04-30 | 1999-04-30 | Control of weeds in tolerant maize crops uses herbicidal combination containing glufosinate, glyphosate, imidazolinone, azole, cyclohexanedione or heteroaryloxyphenoxypropionic acid herbicide |
US09/370,373 US7012040B2 (en) | 1998-08-13 | 1999-08-10 | Herbicidal compositions for tolerant or resistant maize crops |
US11/323,085 US20060111240A1 (en) | 1998-08-13 | 2005-12-30 | Herbicidal compositions for tolerant or resistant maize crops |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/370,373 Division US7012040B2 (en) | 1998-08-13 | 1999-08-10 | Herbicidal compositions for tolerant or resistant maize crops |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/108,522 Continuation US8772199B2 (en) | 1998-08-13 | 2011-05-16 | Herbicidal compositions for tolerant or resistant maize crops |
Publications (1)
Publication Number | Publication Date |
---|---|
US20060111240A1 true US20060111240A1 (en) | 2006-05-25 |
Family
ID=26048135
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/370,373 Expired - Lifetime US7012040B2 (en) | 1998-08-13 | 1999-08-10 | Herbicidal compositions for tolerant or resistant maize crops |
US11/323,085 Abandoned US20060111240A1 (en) | 1998-08-13 | 2005-12-30 | Herbicidal compositions for tolerant or resistant maize crops |
US13/108,522 Expired - Fee Related US8772199B2 (en) | 1998-08-13 | 2011-05-16 | Herbicidal compositions for tolerant or resistant maize crops |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/370,373 Expired - Lifetime US7012040B2 (en) | 1998-08-13 | 1999-08-10 | Herbicidal compositions for tolerant or resistant maize crops |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/108,522 Expired - Fee Related US8772199B2 (en) | 1998-08-13 | 2011-05-16 | Herbicidal compositions for tolerant or resistant maize crops |
Country Status (21)
Country | Link |
---|---|
US (3) | US7012040B2 (en) |
EP (3) | EP2319316B1 (en) |
JP (1) | JP4523162B2 (en) |
CN (2) | CN1220436C (en) |
AR (2) | AR020161A1 (en) |
AU (1) | AU5732199A (en) |
BG (1) | BG65288B1 (en) |
BR (1) | BR9913638B1 (en) |
CA (4) | CA2783196C (en) |
CZ (1) | CZ305417B6 (en) |
DK (1) | DK1104243T3 (en) |
ES (1) | ES2405266T3 (en) |
HR (3) | HRP20010105B1 (en) |
HU (1) | HU230844B1 (en) |
IL (2) | IL141145A0 (en) |
PL (20) | PL214793B1 (en) |
PT (1) | PT1104243E (en) |
RS (1) | RS49988B (en) |
SK (1) | SK288503B6 (en) |
TR (1) | TR200100618T2 (en) |
WO (1) | WO2000008936A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110152096A1 (en) * | 2006-06-06 | 2011-06-23 | Feng Paul C C | Methods for weed control |
EP2454940A3 (en) * | 2006-10-25 | 2012-10-10 | Monsanto Technology LLC | Cropping systems for managing weeds |
US8420888B2 (en) | 2007-02-26 | 2013-04-16 | Monsanto Technology Llc | Chloroplast transit peptides for efficient targeting of DMO and uses thereof |
USRE44971E1 (en) | 2006-06-06 | 2014-06-24 | Monsanto Technology Llc | Method for selection of transformed cells |
US11219210B2 (en) | 2014-11-14 | 2022-01-11 | Fmc Corporation | Compositions and methods for controlling weeds in crops |
WO2024165545A1 (en) * | 2023-02-07 | 2024-08-15 | Upl Mauritius Limited | An herbicidal combination, composition and method of controlling weeds using the same |
WO2025061721A1 (en) * | 2023-09-21 | 2025-03-27 | Specialty Operations France | Herbicidal compositions comprising specific surfactants |
Families Citing this family (78)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL214793B1 (en) * | 1998-08-13 | 2013-09-30 | Bayer Cropscience Ag | Application of herbicide composition, method for controlling weeds and herbicide formulation |
DE19853827A1 (en) † | 1998-11-21 | 2000-05-25 | Aventis Cropscience Gmbh | Selective herbicidal composition for use in e.g. cereals, cotton or soya, comprises p-hydroxyphenyl pyruvate dioxygenase inhibiting benzoyl compound herbicide and safener, e.g. fenclorim or dicamba |
US6713433B2 (en) | 1999-08-11 | 2004-03-30 | Monsanto Technology, Llc | Coformulation of an oil-soluble herbicide and a water-soluble herbicide |
US6689719B2 (en) | 1999-08-11 | 2004-02-10 | Monsanto Technology Llc | Coformulation of carfentrazone-ethyl and glyphasate |
DE19950943A1 (en) | 1999-10-22 | 2001-05-17 | Aventis Cropscience Gmbh | Synergistic herbicidal compositions containing herbicides from the group of inhibitors of hydroxyphenylpyruvate dioxygenase |
EP1267621B1 (en) | 2000-03-27 | 2004-02-11 | Basf Aktiengesellschaft | Synergistic herbicidal methods and compositions |
AU2001253324A1 (en) * | 2000-04-13 | 2001-10-30 | Fmc Corporation | Safening crops from the phytotoxic effects of herbicidally active n-phosphonomethyl-glycines |
PL218885B1 (en) * | 2000-08-31 | 2015-02-27 | Basf Se | Herbicide mixtures |
US6593273B2 (en) | 2000-10-06 | 2003-07-15 | Monsanto Technology Llc | Method for reducing pest damage to corn by treating transgenic corn seeds with pesticide |
US6586365B2 (en) | 2000-10-06 | 2003-07-01 | Monsanto Technology, Llc | Method for reducing pest damage to corn by treating transgenic corn seeds with clothianidin pesticide |
US8080496B2 (en) | 2000-10-06 | 2011-12-20 | Syngenta Crop Protection, Inc. | Method for reducing pest damage to corn by treating transgenic corn seeds with thiamethoxam pesticide |
AR036580A1 (en) * | 2001-09-27 | 2004-09-15 | Syngenta Participations Ag | HERBICIDE COMPOSITION |
DE10160139A1 (en) * | 2001-12-07 | 2003-06-18 | Bayer Cropscience Gmbh | Synergistic herbicidal compositions containing certain herbicides from the group of benzoylcylohexanediones |
JP2003192511A (en) * | 2001-12-27 | 2003-07-09 | Hodogaya Agros Kk | Fine granules that control weeds that are stable against weather fluctuations |
JP2003192510A (en) * | 2001-12-27 | 2003-07-09 | Hodogaya Agros Kk | Mixed fine granules containing glyphosate |
US20070093390A1 (en) * | 2003-03-13 | 2007-04-26 | Basf Aktiengesellschaft | Synergistically acting herbicidal mixtures |
GB0314190D0 (en) * | 2003-06-18 | 2003-07-23 | Syngenta Participations Ag | Method of controlling weeds |
BR122014007725B1 (en) | 2004-03-10 | 2016-10-11 | Monsanto Technology Llc | method of killing or controlling weeds or unwanted plants comprising applying glyphosate aqueous herbicide concentrate composition |
MX2007013867A (en) * | 2005-05-05 | 2008-01-24 | Monsanto Technology Llc | Interaction of glyphosate with photosystem ii inhibitor herbicides as a selection tool for roundup ready events. |
US8754009B2 (en) | 2005-06-09 | 2014-06-17 | Bayer Cropscience Ag | Active compound combinations |
US8207092B2 (en) | 2006-10-16 | 2012-06-26 | Monsanto Technology Llc | Methods and compositions for improving plant health |
BRPI0717640A2 (en) * | 2006-10-16 | 2013-11-12 | Monsato Technology Llc | PROCESS AND COMPOSITIONS FOR INCREASING PLANT HEALTH |
JP5416354B2 (en) * | 2007-02-02 | 2014-02-12 | 石原産業株式会社 | Herbicidal composition containing a benzoylpyrazole compound |
BRPI0813961B8 (en) * | 2007-06-29 | 2022-06-28 | Dow Agrosciences Llc | METHOD FOR CONTROL OF GLYPHOSATE RESISTANT WEATHER |
EP2197272B1 (en) * | 2007-08-27 | 2011-09-28 | Syngenta Participations AG | Herbicidal composition and method of use thereof |
CN103025167A (en) | 2010-05-21 | 2013-04-03 | 拜耳知识产权有限责任公司 | Herbicidal agents for tolerant or resistant rice cultures |
CN103025166A (en) | 2010-05-21 | 2013-04-03 | 拜耳知识产权有限责任公司 | Herbicidal agents for tolerant or resistant grain cultures |
US20110287933A1 (en) * | 2010-05-21 | 2011-11-24 | Bayer Cropscience Ag | Herbicidal composition for tolerant or resistant oilseed rape crops |
BR112012029621A2 (en) | 2010-05-21 | 2015-09-22 | Bayer Ip Gmbh | herbicidal agents for tolerant or resistant maize crops |
WO2012025472A1 (en) * | 2010-08-24 | 2012-03-01 | Basf Se | Agrochemical mixtures for increasing the health of a plant |
EP2460404A1 (en) * | 2010-12-01 | 2012-06-06 | Basf Se | Compositions containing identical polyamine salts of mixed anionic pesticides |
CA3058987C (en) | 2011-10-26 | 2021-10-12 | Monsanto Technology Llc | Salts of carboxylic acid herbicides |
CN103371173A (en) * | 2012-04-21 | 2013-10-30 | 陕西韦尔奇作物保护有限公司 | Weeding composition containing glufosinate-ammonium and sulfonylurea |
CN103371174A (en) * | 2012-04-25 | 2013-10-30 | 陕西韦尔奇作物保护有限公司 | Weeding composition containing glufosinate-ammonium and amides |
CN103371176A (en) * | 2012-04-26 | 2013-10-30 | 陕西韦尔奇作物保护有限公司 | Glufosinate-ammonium-containing pesticide composition |
AR091268A1 (en) | 2012-06-04 | 2015-01-21 | Monsanto Technology Llc | WATER CONCENTRATED HERBICIDE COMPOSITIONS CONTAINING GLYPHOSATE SALTS AND DICAMBA SALTS |
CA2889666C (en) | 2012-11-05 | 2021-07-20 | Monsanto Technology Llc | Low volatility herbicidal compositions comprising an auxin herbicide and a monocarboxylic acid or monocarboxylate thereof |
EP2961276B1 (en) | 2013-02-27 | 2018-08-08 | Monsanto Technology LLC | Glyphosate and dicamba tank mixtures with improved volatility |
CN103319257A (en) * | 2013-06-29 | 2013-09-25 | 四川省乐山市福华通达农药科技有限公司 | Glyphosate, trace element and mesotrione granula and preparation method thereof |
AU2016208065B2 (en) * | 2015-01-15 | 2019-08-22 | Basf Se | Herbicidal combination comprising saflufenacil and glufosinate |
CN107427004B (en) | 2015-01-22 | 2021-06-08 | 巴斯夫农业公司 | Ternary herbicidal combinations comprising saflufenacil |
CA2985395C (en) | 2015-05-11 | 2024-03-12 | Bayer Cropscience Aktiengesellschaft | Herbicide combinations comprising l-glufosinate and indaziflam |
CN107835638B (en) | 2015-07-10 | 2024-12-31 | 巴斯夫农业公司 | Herbicidal composition comprising cyproconazole and acetochlor or pretilachlor |
WO2017009061A1 (en) | 2015-07-10 | 2017-01-19 | BASF Agro B.V. | Herbicidal composition comprising cinmethylin and saflufenacil |
WO2017009056A1 (en) | 2015-07-10 | 2017-01-19 | BASF Agro B.V. | Herbicidal composition comprising cinmethylin and dimethenamid |
US11219212B2 (en) | 2015-07-10 | 2022-01-11 | BASF Agro B.V. | Herbicidal composition comprising cinmethylin and imazamox |
US10980232B2 (en) | 2015-07-10 | 2021-04-20 | BASF Agro B.V. | Herbicidal composition comprising cinmethylin and pyroxasulfone |
PL3319434T3 (en) | 2015-07-10 | 2019-11-29 | Basf Agro Bv | Herbicidal composition comprising cinmethylin and pethoxamid |
KR20180027580A (en) | 2015-07-10 | 2018-03-14 | 바스프 아그로 비.브이. | Herbicide compositions comprising neomycinoline and certain quinolinecarboxylic acids |
US11219215B2 (en) | 2015-07-10 | 2022-01-11 | BASF Agro B.V. | Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase |
AU2016292569B2 (en) | 2015-07-10 | 2021-01-21 | BASF Agro B.V. | Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors |
CN106070313A (en) * | 2016-06-22 | 2016-11-09 | 南京华洲药业有限公司 | The Herbicidal combinations of a kind of Glufosinate-ammoniumpesticideng and triaziflam and application thereof |
CN105935060A (en) * | 2016-06-22 | 2016-09-14 | 南京华洲药业有限公司 | Herbicidal composition containing glufosinate-ammonium and prosulfuron and applications thereof |
CN105941469B (en) * | 2016-06-22 | 2019-02-12 | 南京华洲药业有限公司 | A kind of Herbicidal combinations and its application of Glufosinate-ammoniumpesticideng and ethoxyfen-ethyl |
CN105935059A (en) * | 2016-06-22 | 2016-09-14 | 南京华洲药业有限公司 | Herbicidal composition containing glufosinate-ammonium and flufenacet and applications thereof |
CN105994356A (en) * | 2016-06-22 | 2016-10-12 | 南京华洲药业有限公司 | Weeding composition containing glufosinate and halosulfuron-methyl and application of weeding composition |
CN106106508B (en) * | 2016-08-17 | 2018-07-13 | 四川利尔作物科学有限公司 | Herbicidal combinations and its application |
CN106508954A (en) * | 2016-12-12 | 2017-03-22 | 安徽常泰化工有限公司 | Cornfield herbicide composition |
CN106818786B (en) * | 2017-03-22 | 2020-03-13 | 山东潍坊润丰化工股份有限公司 | Herbicidal composition containing isoxaflutole and imazapic and application thereof |
MX2020000971A (en) | 2017-07-27 | 2020-07-13 | Basf Se | Use of herbicidal compositions based on l-glufosinate in tolerant field crops. |
EP3440939A1 (en) * | 2017-08-09 | 2019-02-13 | Basf Se | Herbicidal mixtures comprising l-glufosinate |
WO2019030103A1 (en) * | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate or its salt and at least one auxinic herbicide |
WO2019030101A1 (en) | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate or its salt and at least one bleacher herbicide |
BR122023021528A2 (en) | 2017-08-09 | 2024-03-05 | Basf Se | HERBICIDE MIXTURE, PESTICIDE COMPOSITION AND METHOD FOR CONTROLLING UNDESIRABLE VEGETATION |
CA3070179A1 (en) | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate and their use in soybean cultures |
WO2019030086A2 (en) * | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate and their use in canola cultures |
KR20200035125A (en) * | 2017-08-09 | 2020-04-01 | 바스프 에스이 | Herbicide mixture comprising L-glufosinate or a salt thereof and one or more VLCFA inhibitors |
WO2019030092A1 (en) * | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate or its salt and at least one photosynthesis inhibitor |
WO2019030091A2 (en) | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate and their use in cotton cultures |
WO2019030100A1 (en) | 2017-08-09 | 2019-02-14 | Basf Se | Herbicidal mixtures comprising l-glufosinate or its salt and at least one mitosis inhibitor |
AU2018389233B2 (en) * | 2017-12-22 | 2024-08-08 | Monsanto Technology Llc | Herbicidal mixtures |
CN108849882A (en) * | 2018-06-14 | 2018-11-23 | 四川利尔作物科学有限公司 | A kind of low temperature resistant 2 first of glufosinate-ammonium, 4 chlorine water agent |
CN108902171A (en) * | 2018-07-23 | 2018-11-30 | 安徽华星化工有限公司 | A kind of Herbicidal combinations of Glufosinate-ammoniumpesticideng and amides |
CA3130265A1 (en) | 2019-02-19 | 2020-08-27 | Gowan Company, L.L.C. | Stable liquid compositions and methods of using the same |
US10555528B1 (en) | 2019-03-20 | 2020-02-11 | Sumitomo Chemical Company, Limited | Herbicidal composition and method for controlling weeds |
US12262715B2 (en) | 2020-02-05 | 2025-04-01 | Basf Se | Herbicidal mixtures comprising L-glufosinate or its salt and at least one protoporphyrinogen-IX oxidase inhibitor |
CN113016816B (en) * | 2021-03-12 | 2022-03-01 | 淄博新农基作物科学有限公司 | Weeding composition containing isoxaflutole and metosulam |
CN115989818A (en) * | 2021-10-20 | 2023-04-21 | 江苏优士化学有限公司 | A kind of ternary compound pesticide composition containing glyphosate |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4265654A (en) * | 1977-12-28 | 1981-05-05 | Meiji Seika Kaisha Ltd. | Herbicidal compositions |
US4445927A (en) * | 1979-12-28 | 1984-05-01 | Nitrokemia Ipartelepek | Herbicidal compositions containing N-(phosphonomethyl)-glycine |
US5238904A (en) * | 1991-01-22 | 1993-08-24 | Hoechst Aktiengesellschaft | Liquid preparations of herbicide mixture based on glufosinate |
US5332714A (en) * | 1989-07-08 | 1994-07-26 | Hoechst Aktiengesellschaft | Defoamer for liquid wetting agents and low-foam liquid plant protection agents |
US5461019A (en) * | 1992-05-15 | 1995-10-24 | Hoechst Aktiengesellschaft | Synergistic herbicidal combinations, process for their preparation, and use of said compositions as herbicidal agents |
US5478798A (en) * | 1990-12-01 | 1995-12-26 | Basf Aktiengesellschaft | Herbicidal N-[(1,3,5-triazin-2-yl)-aminocarbonyl]-benzenesulfonamides |
US5506195A (en) * | 1994-11-01 | 1996-04-09 | Zeneca Limited | Selective 1,3-cyclohexanedione corn herbicide |
US5599769A (en) * | 1990-11-13 | 1997-02-04 | Hoechst Aktiengesellschaft | Synergistic herbicidal compositions comprising glyphosate or glufosinate in combination with a sulfonylurea herbicide |
US5739082A (en) * | 1990-02-02 | 1998-04-14 | Hoechst Schering Agrevo Gmbh | Method of improving the yield of herbicide-resistant crop plants |
US5990047A (en) * | 1995-06-08 | 1999-11-23 | Hoechst Schering Agrevo Gmbh | Herbicidal composition comprising 4-iodo-2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl]benzoi c esters |
US7012040B2 (en) * | 1998-08-13 | 2006-03-14 | Hoechst Schering Agrevo Gmbh | Herbicidal compositions for tolerant or resistant maize crops |
Family Cites Families (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3035554A1 (en) | 1980-09-20 | 1982-05-06 | Hoechst Ag, 6000 Frankfurt | HERBICIDAL AGENTS |
US4440562A (en) * | 1981-07-20 | 1984-04-03 | Monsanto Company | Herbicidal emulsions |
US5006158A (en) * | 1984-12-20 | 1991-04-09 | Ici Americas Inc. | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
US4535060A (en) | 1983-01-05 | 1985-08-13 | Calgene, Inc. | Inhibition resistant 5-enolpyruvyl-3-phosphoshikimate synthetase, production and use |
JPS60500438A (en) | 1983-01-17 | 1985-04-04 | モンサント カンパニ− | Plasmids for transforming plant cells |
ATE35888T1 (en) | 1983-03-28 | 1988-08-15 | Ciba Geigy Ag | N-PHENYLSULFONYL-N'-PYRIMIDINYL AND TRIAZINYL UREAS. |
BR8404834A (en) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | METHOD TO GENETICALLY MODIFY A PLANT CELL |
BR8600161A (en) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | CHEMICAL GENE, HYBRID, INTERMEDIATE PLASMIDIO VECTORS, PROCESS TO CONTROL INSECTS IN AGRICULTURE OR HORTICULTURE, INSECTICIDE COMPOSITION, PROCESS TO TRANSFORM PLANT CELLS TO EXPRESS A PLANTINIDE TOXIN, PRODUCED BY CULTURES, UNITED BY BACILLA |
JPS61293956A (en) | 1985-06-21 | 1986-12-24 | Tokuyama Soda Co Ltd | Chloroacetamide compound and its manufacturing method |
DE3686633T2 (en) | 1985-10-25 | 1993-04-15 | David Matthew Bisaro | PLANT VECTORS. |
ATE57390T1 (en) | 1986-03-11 | 1990-10-15 | Plant Genetic Systems Nv | PLANT CELLS OBTAINED BY GENOLOGICAL TECHNOLOGY AND RESISTANT TO GLUTAMINE SYNTHETASE INHIBITORS. |
DE3771135D1 (en) * | 1986-05-09 | 1991-08-08 | Hoechst Ag | HERBICIDAL AGENTS. |
ES2038631T3 (en) | 1986-08-23 | 1993-08-01 | Hoechst Aktiengesellschaft | PROCEDURE FOR OBTAINING A RESISTANCE GENE AGAINST PHOSPHINOTRICIN (PTC). |
IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
CN87100603A (en) | 1987-01-21 | 1988-08-10 | 昂科公司 | Vaccines against melanoma |
JPH02501922A (en) | 1987-10-28 | 1990-06-28 | ローヌ‐プーラン・アグロシミ | Herbicidal compositions based on glyphosate-type herbicides and phenoxybenzoic acid-type herbicides, and methods for treating unwanted plants using these compositions |
DE3809159A1 (en) | 1988-03-18 | 1989-09-28 | Hoechst Ag | LIQUID HERBICIDES |
EP0360750A3 (en) | 1988-09-22 | 1991-01-02 | Ciba-Geigy Ag | Novel herbicide tolerant plants |
DE3919036A1 (en) * | 1989-06-10 | 1990-12-13 | Hoechst Ag | LIQUID HERBICIDAL MIXTURE |
JP2811121B2 (en) | 1989-06-29 | 1998-10-15 | ノバルティス アクチエンゲゼルシャフト | Heterocyclic compounds |
US5310667A (en) | 1989-07-17 | 1994-05-10 | Monsanto Company | Glyphosate-tolerant 5-enolpyruvyl-3-phosphoshikimate synthases |
GB9017539D0 (en) | 1990-08-10 | 1990-09-26 | Rhone Poulenc Agriculture | New compositions of matter |
DE3938564A1 (en) | 1989-11-21 | 1991-05-23 | Hoechst Ag | HERBICIDAL AGENTS |
DE4327056A1 (en) * | 1993-08-12 | 1995-02-16 | Hoechst Schering Agrevo Gmbh | Process for increasing the yield of herbicide-resistant crops |
DE4003045A1 (en) | 1990-02-02 | 1991-08-08 | Hoechst Ag | VIRUS / HERBICIDE RESISTANCE GENES, METHOD FOR THEIR PRODUCTION AND THEIR USE |
ATE241007T1 (en) | 1990-03-16 | 2003-06-15 | Calgene Llc | DNAS CODING FOR PLANT DESATURASES AND THEIR APPLICATIONS |
US5198599A (en) | 1990-06-05 | 1993-03-30 | Idaho Resarch Foundation, Inc. | Sulfonylurea herbicide resistance in plants |
EP0536293B1 (en) | 1990-06-18 | 2002-01-30 | Monsanto Technology LLC | Increased starch content in plants |
CA2083948C (en) | 1990-06-25 | 2001-05-15 | Ganesh M. Kishore | Glyphosate tolerant plants |
DE4029304A1 (en) | 1990-09-15 | 1992-03-19 | Hoechst Ag | Synergistic herbicide mixts. - contain alkyl-polyglycol-ether! sulphate surfactant and a leaf-effective herbicide |
AU8848791A (en) | 1990-11-13 | 1992-06-11 | Hoechst Aktiengesellschaft | Synergistic herbicidal agent |
SE467358B (en) | 1990-12-21 | 1992-07-06 | Amylogene Hb | GENETIC CHANGE OF POTATISE BEFORE EDUCATION OF AMYLOPECT TYPE STARCH |
ES2084975T3 (en) | 1991-01-25 | 1996-05-16 | Ciba Geigy Ag | SULFONILUREAS AS HERBICIDES. |
ZA92970B (en) | 1991-02-12 | 1992-10-28 | Hoechst Ag | Arylsulfonylureas,processes for their preparation,and their use as herbicides and growth regulators |
DE4104782B4 (en) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Novel plasmids containing DNA sequences that cause changes in carbohydrate concentration and carbohydrate composition in plants, as well as plants and plant cells containing these plasmids |
US5538938A (en) † | 1994-10-14 | 1996-07-23 | Monsanto Company | Stable emulsion flowable formulation of a 2-chloroacetamide herbicide and an imidazolinone herbicide |
UA63884C2 (en) * | 1995-04-12 | 2004-02-16 | Singenta Participations Ag | Herbicidal composition and a method of controlling the emergence of undesirable plants |
US5656615A (en) | 1995-04-12 | 1997-08-12 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of cancers and viruses in mammals |
AP927A (en) * | 1996-03-29 | 2001-01-12 | Monsanto Europe Sa | New use of N-(phosphonomethyl) glycine and derivatives thereof. |
AU2475197A (en) † | 1996-06-11 | 1997-12-18 | American Cyanamid Company | Method to overcome the antagonistic interactions of herbicides |
JP3799669B2 (en) * | 1996-07-29 | 2006-07-19 | 日産化学工業株式会社 | Herbicidal composition |
US6586367B2 (en) * | 1996-09-05 | 2003-07-01 | Syngenta Crop Protection, Inc. | Process for the control of weeds |
AR008158A1 (en) | 1996-09-05 | 1999-12-09 | Syngenta Participations Ag | PROCESS FOR THE CONTROL OF BAD HERBS IN USEFUL PLANTS CROPS THAT ARE RESISTANT TO A PHOSPH-HERBICIDE AND A HERBICIDAL COMPOSITION FOR SUCH USE. |
BR9712695A (en) | 1996-11-07 | 1999-10-19 | Zeneca Ltd | Herbicide-tolerant plants |
-
1999
- 1999-08-10 PL PL393778A patent/PL214793B1/en unknown
- 1999-08-10 PL PL393779A patent/PL212314B1/en unknown
- 1999-08-10 PL PL397721A patent/PL217234B1/en unknown
- 1999-08-10 PL PL397731A patent/PL217914B1/en unknown
- 1999-08-10 EP EP10010490.0A patent/EP2319316B1/en not_active Revoked
- 1999-08-10 PL PL397727A patent/PL217236B1/en unknown
- 1999-08-10 CZ CZ2001-558A patent/CZ305417B6/en not_active IP Right Cessation
- 1999-08-10 PL PL397732A patent/PL215317B1/en unknown
- 1999-08-10 PL PL384057A patent/PL212684B1/en unknown
- 1999-08-10 PL PL397730A patent/PL215316B1/en unknown
- 1999-08-10 PL PL397726A patent/PL215314B1/en unknown
- 1999-08-10 CA CA2783196A patent/CA2783196C/en not_active Expired - Lifetime
- 1999-08-10 PL PL397734A patent/PL217242B1/en unknown
- 1999-08-10 WO PCT/EP1999/005796 patent/WO2000008936A1/en active Application Filing
- 1999-08-10 CA CA2783627A patent/CA2783627C/en not_active Expired - Lifetime
- 1999-08-10 BR BRPI9913638-4A patent/BR9913638B1/en not_active IP Right Cessation
- 1999-08-10 US US09/370,373 patent/US7012040B2/en not_active Expired - Lifetime
- 1999-08-10 HU HU0104049A patent/HU230844B1/en unknown
- 1999-08-10 PL PL397725A patent/PL215005B1/en unknown
- 1999-08-10 PL PL397733A patent/PL217240B1/en unknown
- 1999-08-10 CN CNB998096113A patent/CN1220436C/en not_active Expired - Lifetime
- 1999-08-10 PL PL397728A patent/PL215315B1/en unknown
- 1999-08-10 CA CA2872408A patent/CA2872408C/en not_active Expired - Lifetime
- 1999-08-10 PL PL403117A patent/PL218413B1/en unknown
- 1999-08-10 DK DK99944356.7T patent/DK1104243T3/en active
- 1999-08-10 PT PT99944356T patent/PT1104243E/en unknown
- 1999-08-10 SK SK211-2001A patent/SK288503B6/en not_active IP Right Cessation
- 1999-08-10 IL IL14114599A patent/IL141145A0/en active IP Right Grant
- 1999-08-10 EP EP99944356A patent/EP1104243B1/en not_active Expired - Lifetime
- 1999-08-10 RS YUP-110/01A patent/RS49988B/en unknown
- 1999-08-10 PL PL397729A patent/PL215008B1/en unknown
- 1999-08-10 AU AU57321/99A patent/AU5732199A/en not_active Abandoned
- 1999-08-10 CN CNA2005100039445A patent/CN1644052A/en active Pending
- 1999-08-10 PL PL397735A patent/PL217233B1/en unknown
- 1999-08-10 PL PL397722A patent/PL217232B1/en unknown
- 1999-08-10 PL PL397724A patent/PL217216B1/en unknown
- 1999-08-10 EP EP10010489.2A patent/EP2319315B2/en not_active Expired - Lifetime
- 1999-08-10 PL PL346136A patent/PL212110B1/en unknown
- 1999-08-10 PL PL397723A patent/PL217909B1/en unknown
- 1999-08-10 JP JP2000564450A patent/JP4523162B2/en not_active Expired - Lifetime
- 1999-08-10 CA CA2340013A patent/CA2340013C/en not_active Expired - Lifetime
- 1999-08-10 TR TR2001/00618T patent/TR200100618T2/en unknown
- 1999-08-10 ES ES99944356T patent/ES2405266T3/en not_active Expired - Lifetime
- 1999-08-11 AR ARP990104015A patent/AR020161A1/en not_active Application Discontinuation
-
2001
- 2001-01-28 IL IL141145A patent/IL141145A/en not_active IP Right Cessation
- 2001-02-08 BG BG105229A patent/BG65288B1/en unknown
- 2001-02-09 HR HRP20010105AA patent/HRP20010105B1/en not_active IP Right Cessation
-
2005
- 2005-12-30 US US11/323,085 patent/US20060111240A1/en not_active Abandoned
-
2007
- 2007-11-05 AR ARP070104917A patent/AR063563A2/en active IP Right Grant
-
2011
- 2011-05-16 US US13/108,522 patent/US8772199B2/en not_active Expired - Fee Related
-
2013
- 2013-11-08 HR HRP20131065AA patent/HRP20131065B1/en not_active IP Right Cessation
- 2013-11-08 HR HRP20131064AA patent/HRP20131064A2/en not_active Application Discontinuation
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4265654A (en) * | 1977-12-28 | 1981-05-05 | Meiji Seika Kaisha Ltd. | Herbicidal compositions |
US4445927A (en) * | 1979-12-28 | 1984-05-01 | Nitrokemia Ipartelepek | Herbicidal compositions containing N-(phosphonomethyl)-glycine |
US5332714A (en) * | 1989-07-08 | 1994-07-26 | Hoechst Aktiengesellschaft | Defoamer for liquid wetting agents and low-foam liquid plant protection agents |
US5739082A (en) * | 1990-02-02 | 1998-04-14 | Hoechst Schering Agrevo Gmbh | Method of improving the yield of herbicide-resistant crop plants |
US5599769A (en) * | 1990-11-13 | 1997-02-04 | Hoechst Aktiengesellschaft | Synergistic herbicidal compositions comprising glyphosate or glufosinate in combination with a sulfonylurea herbicide |
US5478798A (en) * | 1990-12-01 | 1995-12-26 | Basf Aktiengesellschaft | Herbicidal N-[(1,3,5-triazin-2-yl)-aminocarbonyl]-benzenesulfonamides |
US5238904A (en) * | 1991-01-22 | 1993-08-24 | Hoechst Aktiengesellschaft | Liquid preparations of herbicide mixture based on glufosinate |
US5461019A (en) * | 1992-05-15 | 1995-10-24 | Hoechst Aktiengesellschaft | Synergistic herbicidal combinations, process for their preparation, and use of said compositions as herbicidal agents |
US5506195A (en) * | 1994-11-01 | 1996-04-09 | Zeneca Limited | Selective 1,3-cyclohexanedione corn herbicide |
US5990047A (en) * | 1995-06-08 | 1999-11-23 | Hoechst Schering Agrevo Gmbh | Herbicidal composition comprising 4-iodo-2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl]benzoi c esters |
US7012040B2 (en) * | 1998-08-13 | 2006-03-14 | Hoechst Schering Agrevo Gmbh | Herbicidal compositions for tolerant or resistant maize crops |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110152096A1 (en) * | 2006-06-06 | 2011-06-23 | Feng Paul C C | Methods for weed control |
US8629328B2 (en) | 2006-06-06 | 2014-01-14 | Monsanto Technology Llc | Methods for weed control using plants transformed with dicamba monooxygenase |
USRE44971E1 (en) | 2006-06-06 | 2014-06-24 | Monsanto Technology Llc | Method for selection of transformed cells |
USRE45048E1 (en) | 2006-06-06 | 2014-07-22 | Monsanto Technology Llc | Methods for weed control using plants having dicamba-degrading enzymatic activity |
EP2454940A3 (en) * | 2006-10-25 | 2012-10-10 | Monsanto Technology LLC | Cropping systems for managing weeds |
US8420888B2 (en) | 2007-02-26 | 2013-04-16 | Monsanto Technology Llc | Chloroplast transit peptides for efficient targeting of DMO and uses thereof |
US8791325B2 (en) | 2007-02-26 | 2014-07-29 | Monsanto Technology Llc | Chloroplast transit peptides for efficient targeting of DMO and uses thereof |
US11219210B2 (en) | 2014-11-14 | 2022-01-11 | Fmc Corporation | Compositions and methods for controlling weeds in crops |
WO2024165545A1 (en) * | 2023-02-07 | 2024-08-15 | Upl Mauritius Limited | An herbicidal combination, composition and method of controlling weeds using the same |
WO2025061721A1 (en) * | 2023-09-21 | 2025-03-27 | Specialty Operations France | Herbicidal compositions comprising specific surfactants |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8772199B2 (en) | Herbicidal compositions for tolerant or resistant maize crops | |
US6723681B2 (en) | Herbicidal compositions for tolerant or resistant cereal crops | |
AU764834B2 (en) | Herbicides for tolerant or resistant cotton cultures | |
US7105470B1 (en) | Herbicidal compositions for tolerant or resistant soybean crops | |
AU764192B2 (en) | Herbicidal agents for tolerant or resistant rice crops | |
RU2251270C2 (en) | Herbicides for tolerant or resistant maize cultures and method for controlling of weeds | |
MXPA01001651A (en) | Herbicides for tolerant or resistant corn cultures |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: BAYER CROPSCIENCE AG, GERMANY Free format text: CHANGE OF NAME;ASSIGNOR:BAYER CROPSCIENCE GMBH;REEL/FRAME:021838/0869 Effective date: 20070413 Owner name: BAYER CROPSCIENCE GMBH, GERMANY Free format text: CHANGE OF NAME;ASSIGNOR:AVENTIS CROPSCIENCE GMBH;REEL/FRAME:021924/0762 Effective date: 20020605 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |
|
AS | Assignment |
Owner name: BAYER INTELLECTUAL PROPERTY GMBH, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BAYER CROPSCIENCE AG;REEL/FRAME:030857/0180 Effective date: 20130722 |